Consider this: on your typical Monday morning, you read the framework post, maybe even download the worksheet. The framework stays fresh in your mind for the next few hours.

Fast forward to Tuesday afternoon - your week is in full swing, and you have a dozen emails, back-to-back meetings, and three escalations waiting for your attention.

On Wednesday at 4.30 pm you meet Lisa, your top-performing team member, for a regular 1:1 meeting. Lisa tells you that she’s thinking about leaving the company. Your heart rate goes up, and every framework you’ve ever read goes out the door.

Does that sound like you?

Well, it definitely sounds a lot like me. I’ve written about Conway’s Law, the Ladder of Inference, the Abilene Paradox, and dozens of others here for years. I still have moments where I walk out of a meeting and think, “I knew exactly what to do there. I just didn’t do it.”

So for the last several months, I’ve been building something to close that gap. And today, I’m excited to reveal it to you! 🧡

It’s called Kyoshi.

What Kyoshi is

Kyoshi is a systems-first leadership coach.

It’s built on the Leadership OS, it knows what you’re dealing with this week, and it helps you to work out a solution like a real coach would.

The word “Kyoshi” comes from Japanese for a ‘master teacher’, someone who has put in the reps and now helps others put in theirs. That’s the energy I wanted with Kyoshi - more “coach”, less “guru”.

And in case you’re curious about the logo - I designed that, too, with intention.

The logo is an open ring with the opening facing up, and it stays open for a reason. I hope you’ll agree with me that leadership is never “finished”, and the best leaders I know stay optimistic and keep going.

That’s what the logo is supposed to symbolize.

What Kyoshi isn’t

Okay, now let’s address the elephant in the room…

At this point you’re probably screaming: Isn’t Kyoshi yet another AI chatbot?

After all, you can already ask a general AI tool like ChatGPT or Claude for leadership advice. So, what’s different?

Here’s the thing:

We’ve all tried asking those generic AI clients for leadership advice. Granted, they spit out a nice and tidy list of ten tips that would fit any manager at any company. The advice also makes us feel good about yourself, and who doesn’t like that?

But here’s the problem: those tools are great at giving you general advice, but really poor at providing anything actionable.

It’s like asking a stranger at a bus stop for marriage advice. You’ll likely get a polite, confident reply, when they have no idea who you are, or how you can act on it.

The Leadership OS has four layers: Leading Self, Leading Others, Leading Results, and Strategic Leadership. Each layer has skills, and skills have associated frameworks.

Here’s my fundamental premise:

And one more thing makes Kyoshi different - it helps you to manage and solve what I call situations.

A situation is the symptom you’re seeing this week in your leadership role, e.g. “my team agrees in meetings and then does nothing.” As you can imagine, the same symptom can come from very different root causes. Maybe it’s the Abilene Paradox. Maybe it’s unclear ownership. Or, maybe your team just doesn’t trust you yet.

Most advice starts with the answer. Good coaching starts with the diagnosis.

The Three Rooms

Kyoshi is organized around three “rooms” or stages if you will, depending on what you’re looking for right now:

• 📚 Learn - the Library - where you go to learn and master the fundamentals of leadership

• 💪 Practice - the Gym - where you go to build your leadership muscle by trying a skill or framework in a safe environment

• 🔧 Apply - the Field - where you put your learning to solve a real situation you’re facing right now

Next, let’s look at the three rooms in a bit more detail.

📚 Learn - The Library

The library is where the skills and frameworks come alive, organized by the Leadership OS so you can see how they connect.

Here’s a quick preview of the library (or the Learn section):

You can explore the library in a number of ways:

• ⚙️ The System: You can learn about the Leadership OS, how the four layers are interrelated, and how the system works under the hood. This forms your foundational understanding of leadership.

• 🧠 The Skills: You can explore the set of essential skills you need to develop as a leader, and how they are linked to the Leadership OS and the layers. You can even ask Kyoshi questions related to a skill, or how to develop that skill.

• 🛠️ The Frameworks: If you’re looking to understand a specific framework, say the Situational Leadership or Radical Candor, you can read how it works, and how it relates to the skills and layers as part of the Leadership OS. You can also browse through the list of all frameworks.

• 📍 The Mind-map: This is for the visual explorers like me :) You can walk into the library and explore the entire system at a glance with the interactive mind map, just like you would when walking into a great bookstore! (I did that recently at the Powell’s bookstore in Portland - what a treat!)

• 🧪 Quizzes: You can also test your understanding of the frameworks with quizzes - this ensures that you’re not just consuming, but also actually learning and retaining.

💪 Practice - The Gym

You don’t get better at hard conversations by “reading” about them. You get better by having them.

In the gym, you rehearse the conversation before you face it for real: it could be the performance review, the pushback from your executive leader, or the engineer on your team who wants a promotion that you can’t yet give.

And because this is not a real situation, you get to try it without the fear of failure, and get to build your muscle and confidence.

Here’s a quick preview of the gym (or Practice section):

In Kyoshi, you have access to:

• 🎭 Role Plays: Kyoshi can play the role of your boss, your team member, your customer, or any stakeholder. And the real value is after the conversation, when Kyoshi will debrief and provide you with feedback to help you improve and get better.

• 🎬 Scenarios: You are presented with a realistic scenario (from a list of several options), and get to be the decision owner. As you go through the scenario, you get to experience the outcomes of your decisions. Like in most things leadership, there are no right answers, just tradeoffs. At the end of the simulation, Kyoshi provides you with feedback so you can get better at handling them when you face them for real.

• 🎯 Drills: You get to practice a framework of your choice (among 100+ in the library) in a realistic situation to experience what it feels like in action. This helps you to build your muscle memory and really practice the application of the framework, beyond just reading about it.

• 🔖 Worksheets: You can generate worksheets for a framework of your choice any time, on-demand, for online or offline use. Download the PDF and print it out to take to a real situation if you like, or just run through the worksheet in a test scenario if that’s what you want.

🔧 Apply - The Field

The field is where the rubber hits the road, so to speak.

The field is where Kyoshi helps you turn your knowledge and skills into actual application to real, live situations you are facing in your leadership role. Kyoshi coaches you through it, asks the questions a good coach would ask, and helps you leave with a decision instead of a vague plan.

You can create new situations directly, or Kyoshi can also prompt you to create a situation mid-conversation to help you track it.

Here’s a quick preview of the field (or Apply section):

Here are some of the things you can do in the field:

• ✅ Track commitments: As Kyoshi learns about the situation through conversation with you, it can infer the underlying commitments. This could include a scheduled meeting with your boss next Tuesday at 3 pm, or a call you need to make to a customer this Friday at 10 am. Kyoshi will proactively monitor these commitments as they emerge through your conversations, and help you stay on track.

• 📎 Generate Artifacts: Kyoshi can help you generate various artifacts, depending on the situation and context. These could include talking points, discussion summaries, downloadable PDFs, etc. You can also attach your own documents to a situation to provide Kyoshi more context beyond just the conversation, and Kyoshi will keep all of those organized and accessible for you.

• 🙌🏼 Prepare: Kyoshi helps you prepare for that big meeting or that high-stakes moment. Let’s say you have an important meeting coming up with your VP next week. You can create a new situation in Kyoshi, and it will help you prepare for it, including the talking points, the slides or artifacts, etc. You can even run a role-play or a scenario to practice before the meeting to get a “feel” for it.

What Kyoshi won’t do

I know many of you reading this are engineering managers, and you’ve seen enough AI hype (for good or for bad depending on how you see it!)

So, let me be clear about what Kyoshi won’t do…

Kyoshi won’t make decisions for you. It helps you think, consider, but you still own the decision.

Kyoshi won’t replace your manager, your mentor, or a human coach. It’s there for the 80% of moments when none of them are available, which, if your week looks like mine, is most of them.

Kyoshi won’t flatter you (yeah - we’ve had enough of that fake humility with ChatGPT and Claude). If the root cause of your problem looks like you, it will say so, but kindly.

🔥 The waitlist is now open!

A small group of you has been using Kyoshi in a private beta for the last couple of weeks. The feedback has been great, and is already helping to shape the product.

Some initial feedback I’ve received from the beta users:

Now it’s your turn. The waitlist is open now at kyoshi.ai/waitlist.

So go ahead and sign up for the waitlist. Kyoshi will be launching soon, and early members will be offered a founding-member plan during launch week that you don’t want to miss out on!

Join the Kyoshi waitlist now →

One last thing

I started The Good Boss because I had bad bosses and good bosses, and the difference came down to what they did on an ordinary weekday when things got hard.

This newsletter gives you the ideas, and Kyoshi is where you practice them and make them real.

I hope you’re as excited about Kyoshi as I am, and I look forward to seeing you work with Kyoshi by your side, and skyrocket your impact as a leader!

Don’t forget to join the waitlist to be the first to get access to Kyoshi!

👉🏻 Join the Kyoshi waitlist → kyoshi.ai/waitlist

❤️ Help spread the word!

If the idea behind Kyoshi resonated with you, please like and share this post with other managers who can benefit from it, including your boss :) If you have any feedback, please drop your comment below. Thank you!

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The Good Boss by Gaurav Jain

👋 Let’s connect: YouTube · Skool · LinkedIn · Substack

When I finally went into the Associate Certified Coach (ACC) training program, I remember doing my first recorded practice session, and later playing it back.

I counted asking exactly eight questions in 30 minutes. And guess what - six of those questions were nothing but advice with a question mark at the end.

Something like: “Have you thought about talking to the PM first?”

That’s what coach trainers call a leading question, which is a big no-no for real coaches.

At the end of that session, I went back and looked at my own work calendar. I had seven 1:1s a week, every week, and most of them followed the same script. I asked my team member what they worked on, what the blockers were, and what I would do.

Since getting formally certified and having coached several managers and leaders as part of my training and at work, I kept leaning on one simple structure to break that habit.

It’s called T-GROW, and, quite honestly, this simple framework turned the most wasted 30 minutes of my week into the most impactful. In this post, I will share how this model works, and how you can leverage it with your teams to turn your 1:1s from status updates to real coaching conversations.

Here’s what we will cover:

• From Tennis Courts to Team Meetings

• The T-GROW Coaching Model

• Why Managers Need a Structure

• Applying T-GROW in Your Next 1:1

• The Flipped 1:1

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

Ready? Let’s dive in.

📣 Introducing: Kyoshi

If you’ve been following me here for a bit, you’re probably familiar with the Leadership OS: the system of skills and frameworks behind great leadership.

For the past several months, I’ve been turning that system into an AI-powered app for leaders like you and me, and I’m excited to say that it’s almost ready to launch! 🚀

Kyoshi is a system-first leadership coach, powered by the Leadership OS, available whenever you need it. Use it to learn the skills, practice the drills, and actually apply your learning to real situations you face every day as a leader.

And yes, it coaches you the way this post describes following the TGROW model: questions first, advice second.

Stay tuned for the full reveal on Friday. 🔥

From Tennis Courts to Team Meetings

T-GROW actually started as GROW back in the 1980s in the UK. It was originally developed by Graham Alexander, Alan Fine and Sir John Whitmore.

Whitmore made it famous in his 1992 book Coaching for Performance, which is still a popular book amongst the coaching and executive leadership fraternity today.

And like with many things, the root of the GROW framework lies in sports.

Whitmore drew a lot of inspiration from Timothy Gallwey’s The Inner Game of Tennis, another great book, in which Gallwey argued that players improve faster when a coach helps them notice what’s happening (and take ownership) rather than when the coach tells them what to fix.

So where did the ‘T’ come from? Great question.

Myles Downey, a coach who ran the School of Coaching in London, added Topic at the front in his book Effective Modern Coaching. His point was that you can’t set a good goal for a conversation until you know what the conversation is actually about.

And that’s how the T-GROW model came to be.

The T-GROW Coaching Model

T-GROW has five specific stages, and should be run in that order. Let’s look at each of the stages.

T: Topic. The topic is simply what the person wants to talk about, or what’s on their mind. If you’re going into a coaching conversation as a coach, you can ask something like “What’s the topic you would like to discuss today?”. This sets the frame and context for the coaching conversation.

G: Goal. The goal tries to identify what they want to walk away with from this conversation. Another way to put it is: what tangible outcomes do they want to achieve by the end of this conversation so they know it was time well spent. As a coach, a question you can ask is: “By the end of our 30 minutes, what would be useful for you?”

R: Reality. The reality is where the details lie - what’s actually going on, the facts of the matter, what they’ve tried, and what they observed, etc. It’s the current state of affairs. This is where you would want to spend the majority of the conversation, as you want to make sure you get to the bottom of the issue, not just the surface level.

O: Options. The options are the possible things or actions they can take to address the issue. Your job is to get them to generate at least 2-3 options, and avoid suggesting options even if you are an expert in that field.

W: Way Forward. This is the final step where you help them figure out which option they would go with, and what the next step would be. This step helps to ground the entire discussion and end with a concrete committment that is actionable.

Why Managers Need a Structure

I know what you might be wondering: why do managers need a coaching framework? Aren’t coaching frameworks for professional coaches?

It’s a good question, so let me try to address it.

A fundamental principle of coaching, as you would be able to tell by now, is to encourage the person to identify the solutions on their own rather than handing out answers or suggestions.

Coaching is not the same as mentoring or consulting. Refer to my other post where I discuss the distinction between the four leadership support roles:

In fact, I would argue that managers and leaders need the structured coaching frameowrk more so than professional coaches.

Why? Because a profesional coach typically has one big advantage over you. They are typically not from the same domain or industry and so they tyipcally don’t know the answer. They don’t know your codebase, your stakeholders, or your org’s history. So, they have nothing to offer, and no temptation to resist.

On the other hand, as a manager, you do have all the context. You probably know the codebase better than your team member, or the stakeholders, or the domain. So, you have that urge to offer solutions, to mentor rather than coach, and that’s what makes coaching your team members hard.

When you hand over the answers to your team, they carry a hidden cost, which compounds over time. If you consistently do this, your team eventually can’t decide anythign without you in the room, and then you will wonder why you are suddently the bottleneck.

T-GROW works because it gives you guardrails for the moment you most want to jump in. You can still be the expert, but you need to hold your expertise untl the person has done their own thinking first. In my experience coaching leaders and individual contributors, most of the time, they get to an answer as good as mine. Sometimes even better, because they know details I don’t.

Applying T-GROW in Your Next 1:1

For the rest of this article, we will focus our attention on putting the T-GROW coaching model into practice in your own team. As we do that, don’t forget to download the T-GROW Coaching Worksheet.

Use this worksheet to:

• Prepare for your next 1:1 in 10 minutes

• Plan your coaching questions for each T-GROW stage

• Hold back advice until your team member has done their own thinking

• Spot where you still rush to give answers

• Turn every 1:1 into a clear commitment and follow-up

How to download the worksheet

This worksheet is part of the Worksheets Collection, available to all paid subscribers to The Good Boss.

• 👉🏻 Upgrade to paid now and get instant access to the entire collection, including this worksheet.

• If you prefer the standalone worksheet, you can purchase it from here.

The Flipped 1:1

So, here’s a simple technique I use to apply the T-GROW model to a 1:1. I call it the Flipped 1:1.

Read more

He was always calm, composed, and polite, and always sported a smile on his face.

I never heard him raise his voice above a gentle whisper. He never yelled, never sent passive-aggressive emails, nor did he ever lose his cool in meetings.

And yet, after every 1-on-1, I would walk away feeling like something was off. On the surface, everything seemed to be “just fine”, but it always felt like something was brewing. Team members, including me, didn’t “speak up”. Nothing was ever said directly.

It took me months to realize what was happening.

That experience made me rethink what toxicity looks like.

We’re wired to spot the loud leaders, the screamers, the micromanagers, the ego-driven tyrants. But some of the most destructive leaders don’t raise their voice. They just smile. And that smile becomes a shield, or should I say, a weapon, for behaviors and a culture that rots the team from the inside.

It reminded me of how I feel watching horror movies.

The Evil Dead, a movie I grew up watching, is pure horror: blood, gore, jump scares. It’s loud, wild, and every time I watch it, I walk out shaken but I quickly move on.

Gone Girl, a psychological thriller, isn’t exactly gory or loud. It’s calm, clinical, and gets under my skin and stays with me for days, if not weeks.

Needless to say, spotting such toxic leaders isn’t easy. They could be hiding in plain sight, and playing their game without you noticing it.

In today’s post, we will explore seven subtle signs you might be dealing with a toxic leader who hides behind a smile.

1. They’re Always ‘Nice’ but Never Honest

In meetings, they’re generous with compliments like: “You’ve been doing amazing work,” or “Great job, Gaurav!”

But behind closed doors, they tell others you’re not quite ready for the next level. That you’re not “strategic enough” or “still need to develop.”

The public praise feels good, but the recognition never materializes. Eventually, you realize you’re just being played or misdirected.

In contrast, real leaders give consistent, transparent feedback. They don’t flatter you to your face while quietly blocking your progress. They use radical candor to share direct, honest feedback that help you grow.

Looking for some inspiration? Check out:

2. They Avoid Conflict but Use Silence as a Weapon

They avoid conflict and stay miles away from confrontation. Avoidance and silence are their biggest weapons.

When they have underperformers in the team, or an obvious team conflict that needs to be addressed, they just close their eyes or look the other way, “hoping” it will resolve itself.

“Time is the greatest healer,” they justify to themselves.

With this inaction, nothing ever gets resolved, and problems continue to fester. But because there’s no yelling or confrontation, it feels like nothing’s wrong. Even when people eventually leave, it happens slowly, and is seen as ‘normal’ attrition.

Effective leaders, on the other hand, build psychological safety by encouraging difficult conversations and modeling honest reflection. They don’t avoid discomfort. They manage through it.

Looking for some inspiration? Check out:

3. They Stay Calm During Setbacks but Shift Blame Subtly

When things go wrong, they smile and say, “No worries, we’ll figure it out.”

You assume it’s all good, until you notice your responsibilities getting pulled away, or you’re being left out of critical decisions. You later learn they’ve been sharing a different version of events with others, one where your name is associated with the failure.

They are masters at shifting blame, silently and methodically. Their calm demeanor masks a strategic deflection of blame.

Strong leaders, in contrast, take responsibility when things go sideways. They protect their team in the tough moments, and they share credit in the good ones.

Looking for some inspiration? Check out:

4. They Preach Teamwork but Only Reward Loyalty

They talk about collaboration and “being one team.” But look closely, and you’ll notice that they’re only really listening to a few voices.

These are usually the ones who agree with them. Who are their ‘yes men’.

The people who push back or offer different perspectives get the subtle nods and the fake smiles. And they get quietly booted out of key meetings. They get fewer opportunities and less visibility.

Teamwork becomes a code word for conformity.

Great leaders promote transparency and reward contribution, not compliance. They give space for their teams to grow, to innovate, and to explore new ideas. They adopt the multiplier mindset.

Looking for some inspiration? Check out:

5. They Say ‘My Door Is Always Open’ but Keep You in the Dark

They pride themselves on being approachable. “Anytime you want to talk, just come by.” They put the burden of approaching them on you.

For those courageous enough to approach them, they don’t really open up. “We’re figuring it out,” or “We’ll share more soon.” are their standard responses.

Meanwhile, major decisions are being made without you, and the context is never shared. And somehow, you’re always a step behind.

The most painful part is this: you’re not shut out directly, you’re just never fully let in.

For great leaders, on the other hand, being open means more than being available. It means being transparent, honest, and even vulnerable. Share what you know, and admit what you don’t know. Create clarity, not confusion.

Looking for some inspiration? Check out:

6. They Appear Calm but Leave a Trail of Chaos

They rarely panic or escalate. They seem to have it together.

But their teams are constantly in motion. Priorities change every week, deadlines move without warning, and feedback is vague or contradictory. And no one really knows what the end goal, or the vision, is.

Their calm exterior hides a lack of vision and direction. The mess is just more elegantly presented.

In contrast, great leaders set the vision for their teams, and build focus through clear goal setting and accountability. They don’t just sit back and watch - they rally their teams around the vision.

Looking for some inspiration? Check out:

7. They Delegate Risk but Never Responsibility

They encourage bold thinking. “Go for it,” they say. “I’ve got your back.”
But when things go sideways, that support vanishes.

They distance themselves just enough to stay clean. Suddenly, your name is on the decision. Your judgment is being questioned.

Worst of all, they smile through it all, claiming it’s just part of the “learning process.”

Great leaders don’t just delegate work. They share ownership. They take real risks with you, not just let you take the fall.

Looking for some inspiration? Check out:

Final Thought: Smiles Can Be Weapons Too

Not every toxic leader looks like a villain. Some smile like they’re your biggest fan.

They praise, they nod their heads, and they never raise their voice.

But like in Gone Girl, it’s not the yelling that hurts you. It’s the quiet manipulation, the psychological games, and the version of the story that gets told when you’re not in the room.

And by the time you realize what’s happening, the damage is already done, and you’re left doubting yourself.

I’ve been there, and done that, and my heart still shudders when I remember those moments.

❤️ Found this helpful?

If you found this post helpful, please like and share it with other managers who can benefit from it, including your boss :) If you have any feedback, please drop your comment below - it helps me keep improving the content. Thank you!

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The Good Boss by Gaurav Jain

👋 Let’s connect: YouTube · Skool · LinkedIn · Substack

One of his team members, Matthew - a senior engineer, was frustrated for lack of growth and was thinking about leaving. The manager saw Matthew as a high performer, and didn’t want to risk losing him, so he wanted to promote him.

It seemed like a simple fix, and I approved it.

But the “fix” didn’t last long.

A few weeks later, two other engineers on the same team came to the manager asking for a promotion. One of them had actually been doing the next level work for longer than Matthew, and was resentful for not being picked for the promotion.

Within a month, the team had three people who felt that they deserved a promotion, and the manager was spending 90% of his 1:1s negotiating instead of actually coaching them.

The manager had made a reasonable call that seemed right in the moment, and let’s face it - we all do this from time to time. But he didn’t realize the cascading impact of that.

In this post, we will discuss Second-Order Thinking, which is a powerful model that can help you avoid such situations. Here’s what we will cover:

• Where Second-Order Thinking Comes From

• How It Works: Following the Chain

• Why Managers Get Hit Hardest

• Applying Second-Order Thinking in Practice

• The Ripple Check

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

Where Second-Order Thinking Comes From

The idea of second-order thinking is likely quite old, but most people attribute the idea to Howard Marks, the co-founder of Oaktree Capital.

In his investor memos, and later in his 2011 book The Most Important Thing, Marks described what he called “second-level thinking.”

His example was around investing in stocks:

Here’s another example, closer to our everyday lives.

I’m from Singapore, and it’s a popular tourist destination for its many attractions, including Universal Studios Singapore (USS).

A few years ago, if a local resident wanted to visit Universal Studios, they would typically book a Monday or Tuesday because weekends are super busy with tourists.

But over time, the tourists themselves picked up on this, and started booking their visits on Mondays and Tuesdays, and guess what - now Mondays have become one of the busiest days… who would’ve thought!

How It Works: Following the Chain

Here’s a simple frame to understand how this works:

• First-order thinking asks “What happens next?”

• Second-order thinking keeps going and asks “And then what?”

Remember the decision my manager made about promoting Matthew? That was a first-order decision.

Second-order effects are the ones that follow from the first. In my experience, they share three traits:

1. They show up later. Maybe weeks or even months after the decision, long after you’ve moved on. Similar to what we noticed weeks after promoting Matthew.

2. They land on other people. These are typically your peers, your teams, or people who weren’t even involved in the original decision.

3. They often push the opposite way from the first-order effect. Just like we saw with Matthew’s case, fixing it for one person created frustration for others.

Here’s another example that I’ve seen play out: A team misses a deadline, so the manager adds a daily status check-in. Here’s how this plays out:

• First-order effect: the check-in creates more visibility, and the next deadline looks more “in control”.

• Second-order effect: senior engineers who are now pulled into the daily status meeting end up losing 30-60 mins per day. They start feeling micromanaged, and worse - they stop raising real issues or risks in the meeting because they notice that th eupdates are starting to become a performance.

• Third-order effect: the next deadline slips anyway.

In a nutshell: the first-order effect seemed reasonable, but the second and higher order effects told a different story.

Why Managers Get Hit Hardest

As we discussed, this effect is not just limited to leadership or team situations, but I’ve seen it hit managers hardest because of two reasons:

• First, your team or stakeholders adapt. Every exception you grant, every miss you ignore, and every person you promote tells your team what actually works here. And guess what - they learn and adapt to that quickly.

• Second, it’s hard to know the higher order impacts due to timing. Typically, first-order results show up in the current moment - today or this week. But second-order effects show up much later - maybe after a few weeks or months - and by the time you may have moved on, or the team has moved on, and nobody even realizes by the time the effect becomes visible.

One more thing I’ve seen: the higher you are in the leadership hierarchy, the less you’re likely to see of the second order effect because you’re further apart from the team.

Applying Second-Order Thinking in Practice

For the rest of this article, we will focus our attention on putting the Second-order Thinking model into practice in your own organization. As we do that, don’t forget to download the Second-Order Thinking Worksheet.

Use this worksheet to:

• Catch ripples before they spread

• Spot who else feels decisions

• Avoid precedents you’ll regret

How to download the worksheet

This worksheet is part of the Worksheets Collection, available to all paid subscribers to The Good Boss.

• 👉🏻 Upgrade to paid now and get instant access to the entire collection, including this worksheet.

• If you prefer the standalone worksheet, you can purchase it from here.

The Ripple Check

Here’s a simple check you can run in less than 10 minutes before you commit to anything that’s hard to undo. I call it the Ripple Check.

Read more

For many years in my leadership career, I was the second kind.

I felt like an impostor. Every night after a long day’s work, my mind would go on this ‘reflection spiral’ of “I should have said this in that meeting”, or “I should have pushed back on that decision”, or “I should have handled that 1:1 differently”. etc. etc.

At that time, I was convinced that I wasn’t doing enough, and that I needed to get better.

Chances are, you’ve felt the same at some point as well.

It took me a long time (and a lot of wasted evenings, I should say!) to figure out what was actually going on. When I finally looked at what I was doing, turned out I was doing most of the right things.

Here’s what I’ve learned after 20+ years of leading teams: the signs that you’re doing well as a manager don’t always look “good” in the moment. In fact, some of them feel like failures.

In this post, I’ll share seven signs that you’re a better manager than you think.

1. You Worry About Whether You’re Any Good at This

This is the one that kept me up at night.

Imagine this: you finish a long, productive day at work, but instead of switching off and relaxing, you start “replaying” the day in your mind.

You remember the comment you made in the staff meeting, or the feedback you shared with your team member that you “softened too much”, or the decision you made that you thought was “too fast”.

In reality, here’s what’s happening.

You’re worrying about your actions actually means that you care about getting things right, you care about your team.

Managers who don’t care about their team don’t lose sleep over what they said in a 1:1. See the irony?

There’s actually a well-known pattern behind this:

So, when you doubt yourself, it often indicates that you have actually climbed high enough to see the whole mountain.

👉🏻 Try this: Instead of asking yourself if you’re a good manager, ask yourself what steps you need to take to make things better for your team.

For a deeper-dive, here are a couple of frameworks:

2. Your Team Brings You Bad News Early

Think about the last time a project failed or a conflict was brewing in your team. When did you hear about it?

If you heard about it weeks before it became a bigger issue, I would say - give yourself some credit.

An early warning to you actually means that your team feels safe enough to tell you the truth.

👉🏻 Try this: The next time someone brings you bad news, thank them for it first. Don’t jump into the analysis or solutions. How you react to bad news will decide if you’ll be the first to hear it the next time round.

Want to know how to build that safety? Check out this framework:

3. People Disagree With You in the Meeting, Not After It

Imagine this: you propose a plan in your team meeting, and one of your engineers says something like “I’m not sure about that…”

How would you feel? Many managers may get annoyed, or even feel a little ‘exposed’. I would, too.

But in reality, if your team is arguing with you in the room, it means that they feel safe.

In fact, I would actually worry if your team is nodding along in the meetings, and then complaining to you in the hallway conversation.

👉🏻 Try this: Before you make a decision, ask your team of any objections or concerns. Don’t assume that everyone agrees to it. The first person to speak up will likely open the door for others.

Looking for some inspiration?

4. Things Run Fine When You’re on Leave

Let’s say you come back from a two-week vacation - what do you expect to see? Maybe a bunch of fires to put out, a number of escalations to handle, and not to mention the pile of emails and Slack messages to respond to.

Right?

Instead, what you actually see is quite different: the releases went out as planned, the customer escalations got handled, and the weekly review happened just fine without you.

How do you feel when you see this? I’m guessing that part of you is relieved, but another part of you is feeling a bit… unnecessary :)

If your team can run without you, that’s a clear sign that you’ve built a great team.

👉🏻 Try this: Pick one recurring meeting you currently run and hand it to someone on your team for the next month. See what happens.

Here’s my own story from a recent vacation:

5. Someone You Managed Outgrew You

Consider this: you hired and coached a manager under you, and he is now a Director in a large company. You let a high performer leave your company for a bigger job, because you thought it was right for them.

If any of that has happened to you, it’s one of the best signs that you are a great manager.

When you lose a strong person on your team to another team or company, let’s face it - you can feel disheartened or gutted. But what if that person sends you a note later thanking you for the mentorship and supporting their path?

👉🏻 Try this: In your next 1:1, ask your team member about what their future aspirations are in 2-3 years, not what they’re working on today. And be honest with them about whether their current path can get them there.

Check out these frameworks for some inspiration:

6. You’ve Changed Your Mind in Front of Your Team

Have you ever said to your team something like “you know what, I was wrong about that?”

If you did, did it feel like you were giving up a little bit of your authority, or your respect?

But in reality, the opposite of that happens.

👉🏻 Try this: The next time you feel the urge to defend your position, stop and ask yourself if you’re doing it because of facts, or just ego.

Check this framework out for more:

7. You Notice When Someone Is “Off” Before They Say Anything

Do you notice when someone on your team starts giving shorter replies on Slack than usual. Or they have their camera off on Zoom for the entire week. Or they’re just more silent than usual in the team meetings?

Many managers are so “busy” that they never notice any of that.

But if you actually pick up on those things, you’ve built a skill that most managers never do.

You’re actually paying attention to the people, not just their work.

👉🏻 Try this: When you notice a small change in behavior of a team member, don’t make assumptions. Just send them a private message or bring it up in your 1:1, and give them the space to talk.

A great framework to check out:

Conclusion: The Feeling Lags the Results

If you’ve been doubting yourself, go back through this list and count how many of these signs you see on your own team.

Here’s the irony: good management rarely feels “good” while you’re doing it. The feeling always shows up later in the results.

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The Good Boss by Gaurav Jain

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The meeting ran for more than an hour.

For most of the meeting, he told me how well I was doing. He appreciated the ownership I had taken on a project despite being a new manager. He even mentioned how I had grown compared to just six months ago.

Somewhere in the middle of the meeting, for about two minutes, he mentioned one thing I needed to work on - that he wanted me to pay more attention to the customer feedback.

Then, he went right back to the good stuff, and he wrapped up by telling me he was glad to have me on the team.

The entire meeting sounded like music to my ears, and I remember walking out of the room feeling happy, thinking that I had nailed it.

A few months later, at my formal review, my manager handed me the compensation letter. I remember reading it and feeling my stomach drop.

I had received a “meets expectations” rating, and an average increment. Nothing close to what I had expected based on the check-in feedback just a few months ago.

It took me weeks to shake off the sleepless nights because I never saw this coming.

When I asked my manager about this, he thought I was “overreacting” because he had shared the feedback with me about the need to pay more attention to our customer’s feedback, and that was a critical part of my role.

As I reflected on this, I realized that this was two minutes of feedback buried in fifty-eight minutes of praise, which is why I had failed to register it at all. To me, it was like the optional footnotes in the margins of a book - the kind nobody pays attention to.

That’s the real problem with the Feedback Sandwich, the framework we will deep-dive into in this post. We will discuss how you can effectively use this framework to deliver feedback without losing the essence of the message.

Here’s what we will cover:

• Why Everyone Loves to Hate This One

• How the Feedback Sandwich Works

• Applying the Feedback Sandwich in Practice

• The Weighted Sandwich

• How This Shows Up In Real Situations

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

Why Everyone Loves to Hate This One

Chances are, you’ve heard about this framework, even if you don’t recognize the name.

If you ask a group of managers about the feedback sandwich, there’s a good chance some of them will roll their eyes.

The common complaint I hear when I speak with managers about it, is that it’s too “soft”, and it encourages the managers to avoid saying the hard thing directly. Or, it trains the person receiving the feedback to tune out the praise because they know the “but” is coming…

Here’s my take: I think the structure of the framework itself isn’t really the problem. Going back to what my manager did, he used the sandwich, yes, but his sandwich was almost entirely bread.

And who likes a sandwich that is mostly bread? :)

How the Feedback Sandwich Works

At its core, the feedback sandwich has three “moves” or “steps”:

• Warm up: Open your conversation with something specific and true about what the person is doing well.

• Deliver feedback: Name the issue that you’re concerned about, clearly, with an example.

• Cool down: Close by reinforcing that you believe they can act on it.

If you read those steps carefully, you’ll notice that the framework doesn’t mention that you should say the good stuff more than the constructive stuff.

Also, the third step isn’t about randomly praising the individual - it’s about reinforcing your support and belief, as you want to make sure they can succeed in the feedback that you have just delivered.

I think that makes this the most critical step of the framework, because if this is not done correctly, you can end up diluting the feedback completely (like my manager did).

Applying the Feedback Sandwich in Practice

Now that we know how the model works, let’s focus our attention on putting the feedback sandwich into practice in your own organization. As we do that, don’t forget to download the Feedback Sandwich Worksheet.

Use this worksheet to:

• Plan the conversation ahead of time

• Confirm the message actually landed

• Commit to a concrete follow-up

How to download the worksheet

This worksheet is part of the Worksheets Collection, available to all paid subscribers to The Good Boss.

• 👉🏻 Upgrade to paid now and get instant access to the entire collection, including this worksheet.

• If you prefer the standalone worksheet, you can purchase it from here.

Next, let’s discuss a simple technique I use, called The Weighted Sandwich, to apply this framework when you’re giving feedback to someone on your team.

The Weighted Sandwich

Read more

A few minutes into the meeting, the temperature in the room started rising. It was obvious that the project was falling apart with slipping deadlines, and tempers started to run short. I noticed that my team leads were looking at me to “jump in” and “fix” the issues being discussed.

Instead, I stayed quiet for almost twenty minutes. I just listened, asked one question, and then let the team work it out.

I know this may seem strange and counterintuitive, and you may think I was being plain rude or ignorant of my team’s challenges.

Let me explain.

I was not being rude or ignorant. In fact, I believe I did the hardest thing a manager can do, which is: do nothing, on purpose.

Let’s face it: the corporate world has built a picture of what “good leadership” looks like: quick answers, fast decisions, visible hustle, and so on.

But having led teams for 20+ years, here’s my honest take: some of the most valuable things you do as a manager are invisible.

They don’t look like “leadership”. In fact, they look like doing nothing at all.

Here are six of them.

1. You let silence sit in a meeting

Let’s say you’re hosting a product review meeting with your team, and a stakeholder from another division asks a hard question.

Your instinct as the manager is usually to “fill the gap”.

Maybe you throw in a quick suggestion, or name a team member to “chime in”, or even throw in a quick joke.

Anything to fill the gap.

Here’s what you should do: resist that temptation.

Wait for ten seconds, maybe twenty.

I know it will feel like forever, but more often than not, someone who was working through the problem will eventually speak up. Maybe it’s your team lead, maybe it’s the more junior person on your team.

But when they do speak up unprompted by you, they will likely have the sharpest, most authentic answer.

Suggested frameworks:

2. You don’t answer the question you’re asked

Let’s say your team lead catches you in the hallway on a busy Wednesday afternoon, and asks: “Should we push the release or keep the date?”

How would you respond?

Most managers would make the obvious move - to just give them the answer.

Here’s what you should do.

Instead of just making the decision for them, throw it back at him: “What would you do, and why?”

I can bet that more likely than not, he already knows the answer. He just wants the assurance, or the permission, or maybe just the “cover”.

Suggested frameworks:

3. You let a mistake finish happening

Let’s say you observe one of your engineers build a solution that you know won’t work. You’ve seen it fail a few times when you were an engineer.

So, you’re tempted to “jump in” and rescue him, rigth?

Don’t do that.

Instead, let him build it, ship it, and fail exactly the way you know he will.

You may think I’m crazy to say that, but hear me out.

When you do that, you’re not “neglecting” him. On the contrary, you’re teaching him how to fish, not just handing him the fish.

Suggested frameworks:

4. You skip the meeting you were invited to

You probably get invited to a gazillion meetings by your team members, by default, because “you’re the manager”.

Maybe as “optional”, if that’s a culture in your team.

And once you have your calendar fills up with all those meetings, you feel the obligation to show up in those meetings.

Again, you’re the “manager”, so your team must need you in the meeting, right?

Wrong.

Here’s what you should do: show up to a fraction of them. And you don’t do this because you’re “too busy”, but because, let’s face it, your mere presence changes what happens in the meeting.

When you’re in the meeting, your team tends to defer to you. They look at you after any big question.

They wait to see what you think before they say what they think.

Suggested frameworks:

5. You don’t touch the document

Let’s say you have a new manager on your team, and he puts together a deck that he’ll be presenting to the stakeholders next week.

As you review the deck, you find three things that you would have written differently. So, what do you do?

Most managers would get tempted to “fix the deck” themselves. After all, they know exactly what to fix and how to fix it.

Resist the temptation to do that.

Instead, just leave a single comment for the new manager to review and update in his terms.

When you rewrite someone else’s work in your own voice, it may feel like “helping”. But in reality, it mostly just teaches them to stop trying, since whatever they produce gets overwritten anyway.

Suggested frameworks:

6. You don’t have a take on everything

Let’s say you’re in a leadership team discussion about a reorg.

The most logical thing for you to do is to “jump into the debate”. Right?

But you decide to stay out of it. You do this not once, but twice.

And you don’t do that because “you don’t care”, but because you can see that the other two managers arguing actually have it covered.

You know that inserting a third opinion into the mix would just give everyone an excuse to continue the argument, instead of converging on a decision.

Suggested frameworks:

Conclusion

The six things we looked at may feel like it’s about being “passive”.

But they’re the exact opposite.

They’re really about restraint, and we all know that restraint takes more discipline than action does.

It’s easy to “jump in”, to fill the silence or rewrite a paragraph. That’s what most managers do.

But it takes discipline and, frankly, trust in your team to sit on your hands instead.

The best leadership I’ve ever seen through my 20+ years as a manager didn’t look like what we have come to expect of leadership.

Instead, it looked like a manager doing nothing, at exactly the right moment, on purpose.

If this resonated with you, hit the ❤️ and consider a restack, it helps this reach more managers who need it. And if you want the frameworks behind posts like this one, check out The Ultimate Leadership Toolkit.

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The Good Boss by Gaurav Jain

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Almost every week, he would tell me some version of “I’m the only one fighting for the team.”

He said this in our 1:1s, in the hallway on the way to get coffee, and at times even in our team meetings.

Yup, that felt awkward.

To be fair, from his perspective, when he said that, he was trying to show how much he “cared.”

But from the team’s perspective, it was a completely different story.

Every problem we raised to him quickly turned into his problem, and then somehow, into his personal mission.

I remember once raising an issue related to team burnout with him, and a few weeks later, I heard him talk about how burnt out he felt. Woot!

As you can imagine, eventually the team stopped raising any problems to him. After all, who likes their problems turned into a drama?

At that time, I wasn’t sure why he did that. I tried to convince myself that he was just a “different personality type”.

It took me years and a fair amount of leadership research to realize what was actually happening.

In this post, I’m going to deep-dive into the Karpman Drama Triangle. We will discuss how it works and how it shows up for leaders (including why it did for my boss).

Here’s what we will cover:

• The Origin of the Drama Triangle

• The Three Roles

• Why This Matters for Leaders

• Applying the Karpman Drama Triangle in Practice

• The Corner Check Technique

• How This Shows Up in Real Situations

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

The Origin of the Drama Triangle

The Drama Triangle was originally introduced by psychiatrist Stephen Karpman in 1968.

Whenever I research frameworks, I love the “origin story” behind them.

Interestingly, Karpman wasn’t studying office politics or leadership philosophies. Not at all.

He was actually studying fairy tales and stage drama. Karpman noticed that basically every story - whether Little Red Riding Hood, soap operas, or even your family’s Thanksgiving dinner - features the same three characters, or ‘roles’, showing up over and over again.

That’s what he called the Drama Triangle, which later became popular as the Karpman Drama Triangle.

Next, let’s look at how the triangle actually works.

The Three Roles

The Karpman Drama Triangle has three ‘roles’:

• The Victim. This is the person who keeps pulling the “victim card”. They keep saying “poor me, nobody helps me… this always happens to me.” I bet you know many so-called ‘victims’ in your own life as well. In most cases, the ‘victim’ feels stuck and powerless, even in situations where he has more control than he wants to admit.

• The Persecutor. This is the critic, or the one who sets impossible standards, and then points out how “everyone is failing to meet them.” Sometimes this is a harsh boss or the task master (I’ve seen plenty of those through my career), and sometimes it’s the boss who holds “high standards” and then holds a gun on his team to meet them.

• The Rescuer. This is the one who pops in to ‘fix things’ (think Spiderman!) like it’s their problem. But in most cases, the rescuer tries to rescue a situation that doesn’t need rescuing at all. He tries to help people who didn’t really ask for help. Remember my boss from earlier - he was the rescuer for our team.

Why This Matters for Leaders

We all know the typical management advice: have the hard conversation, set the expectations, and move on.

Simple? Not quite.

In the last 20+ years leading teams, I’ve seen countless managers who follow that advice, but it leads them nowhere.

Here’s one scenario I’ve seen play out a lot:

• You rescue your team by lowering the bar

• They feel like victim of your low expectations

• You get frustrated with that, and become the persecutor.

• The team gets frustrated, disengaged, and burnt out.

Rise and repeat.

The value of learning this framework is to become more self-aware and team-aware. You want to be able to detect when you’re playing one of those roles of the drama triangle, and how you get out of that trap.

Applying the Karpman Drama Triangle in Practice

For the rest of this article, we will focus our attention on putting the Karpman Drama Triangle into practice in your own team and organization.

As we do that, don’t forget to download the Karpman Drama Triangle Worksheet.

Use this worksheet to:

• Catch which corner of the triangle you’re standing in, before you speak from it

• Spot the specific conversation where you keep replaying Victim, Persecutor, or Rescuer

• Build a habit of noticing the pattern in the moment, not three days later in the shower

How to download the worksheet

This worksheet is part of the Worksheets Collection, available to all paid subscribers to The Good Boss.

• 👉🏻 Upgrade to paid now and get instant access to the entire collection, including this worksheet.

• If you prefer the standalone worksheet, you can purchase it from here.

The Corner Check Technique

Read more

But the secret to great leadership is not the shiny ideas. It’s the boring stuff.

I know what you’re thinking… how can boring stuff be any good?

Please, hear me out.

I’m talking about the routines that are so dull that they’re easy to skip. The practices that feel too simple to matter.

And yet, these are the very habits that matter in the long run.

I’ve tried every new app, read every trendy book, but none of it stuck. What stuck were these 7 habits, and they changed how I lead.

Here’s your chance: make them yours, and watch your leadership compound over time.

Ready? Let’s go.

1. Write Down Your Top 3 Priorities. Every. Single. Day.

Most leaders I talk to wake up and dive into Slack, email, or meetings.

Yup, I used to do that, too.

That’s not you leading. That’s your calendar leading you.

Instead, before the chaos of the day takes over, ask yourself:

What three things matter most today?

These might look like:

• Block time to prepare for Friday’s executive presentation and avoid scrambling last minute.

• Have a 1:1 conversation with a team member who’s been disengaged lately.

• Carve out 90 minutes to think through the org redesign and sketch out the options.

Write them down on a sticky note, a journal, or your Notes app. I do this on my morning walk using my Notion app.

This habit forces you to pause and filter. It brings clarity. It stops you from reacting all day.

Looking for some inspiration? Check out:

2. Block Time to Think

If your calendar has zero time for thinking, you’re not leading.

You’re just going through the motions.

Block 30 minutes a week to sit quietly with a notebook and a pen. Keep your phone in a room at the other end of your house.

Notebook and pen. Really?

Yes, I know it sounds boring, but trust me, it’s powerful as hell.

Ask yourself and write down:

• What’s going well?

• What’s not?

• What am I avoiding?

• What needs to change?

These questions sound simple, but they let you zoom out and actually uncover what you might be missing all along.

In fact, many of the big strategic moves I have made started as ideas on this very list.

Looking for some inspiration? Check out:

3. Ask the Same 3 Questions in Every 1-on-1

I know what you’re thinking… are you kidding me?

No, I’m not. I’m dead serious.

You don’t need a fresh agenda for every 1-on-1. You just need rhythm.

Try these three questions every single time:

1. What’s working?

2. What’s frustrating?

3. What do you need from me?

Trust me: if you ask them regularly, while being fully present and alert, I guarantee you - magic will happen!

• Your team will open up

• Small issues will surface early before they explode

• You will uncover blockers you didn’t know ever existed

Most importantly, you will build genuine trust with your team.

Looking for some inspiration? Check out:

4. End Every Meeting With Clear Action Items

I hear many managers swear by 15-minute meetings.

I’m not against short meetings, but here’s my take:

You don’t need to make meetings shorter. What you really need is to make meetings count.

I’ve been to countless meetings that were a complete waste of everyone’s time because they failed to ask a simple question at the end:

Two minutes of clarity can save 10 hours of confusion, missed expectations, and worst of all… passive-aggressive follow-ups.

Here’s what this looks like in real teams:

• After a discussion on your platform strategy: “Sara to draft the first version of the deck by Wednesday, and Mike to get the 3 stakeholders' inputs by Friday.”

• After a planning meeting: “Each team lead to review their resourcing and send revised plans by EOD Thursday.”

• After a leadership alignment call: “Jane owns the final decision on pricing. Everyone else to send input by tomorrow noon. Final call by Friday.”

Even if the discussion is fuzzy, the next step should be sharp.

Looking for some inspiration? Check out:

5. Send One Thank-You Note Every Week

I’m not talking about adding hearts all over your Slack threads. That you should avoid for sure.

But true gratitude isn’t cringe. It’s human, and it’s real.

Send a simple note: a slack message, a quick shoutout in a team meeting, or a simple pat on the back. Do this every week to someone who has demonstrated what ‘good’ looks like.

And most importantly, it needs to be real, tangible, and honest.

It might seem boring to you, but if you do this consistently, your simple message will have a larger impact than you can ever imagine, and it will remind the team that you notice and you care.

Here’s what this habit might look like in action:

• You DM an engineer: “The way you stayed calm during that customer escalation was masterful. Thanks for having our back.”

• You post in a public Slack channel: “Shoutout to the Ops team for pulling off the migration with zero downtime - it saved our customers countless wasted hours.”

• You send an email to someone’s manager: “Just wanted to let you know that Leo has been incredibly responsive and thoughtful in every discussion. I genuinely feel that he is a real asset to this project.”

These moments take 90 seconds, but their impact could last for days or even weeks.

Looking for some inspiration? Check out:

6. Audit Your Week Like a CEO

No, you don’t need to be a CEO to do this.

Every Friday afternoon, pull up your calendar for the week that’s ending, and ask yourself:

• What drained me?

• What energized me?

• What should I drop next week?

Now, take those insights and run them through the Eisenhower Matrix (see deep-dive link below):

• Urgent & Important → Do it

• Important & Not Urgent → Schedule it

• Urgent & Not Important → Delegate it

• Not Urgent & Not Important → Delete it

A boring habit, but this combo of reflection + prioritization to plan your calendar for next week can supercharge your impact as a leader.

Looking for some inspiration? Check out:

7. Read One Leadership Idea or Article Every Week

Not ten, not five.

Just one.

It could be:

• One chapter from a leadership book.

• One long-form article or substack post that makes you pause.

• One new idea or insight related to leadership

Do this weekly and, in a year, you’ll have digested 50+ new perspectives.

This is how learning compounds, one week at a time.

Remember: I’m not asking you to read 10 books in a week and then go on a book diet for months.

That’s how you grow.

Shameless plug: if you’re looking for one powerful read a week, subscribe to The Good Boss. I share practical leadership insights straight from the trenches.

Looking for some inspiration? Check out:

Conclusion: Leadership Isn’t Glamorous. It’s Repetitive

By now, I hope you’ll agree with me on this one.

Leadership is not built in moments of brilliance.

It’s built in repetition, day in and day out, of boringly simple habits.

These habits may be boring, but they’re powerful, and they will compound over time.

❤️ Found this helpful?

If you found this post helpful, please like and share it with other managers who can benefit from it, including your boss :) If you have any feedback, please drop your comment below - it helps me keep improving the content. Thank you!

Share

Subscribe to The Good Boss to get actionable strategies every Monday & Thursday, plus my ‘20 Essential Leadership Tools’ guide free when you sign up

💬 Join the conversations

Join The Good Boss community if you’re tired of leadership content that sounds good but doesn’t work when you’re actually in the room.

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The Good Boss by Gaurav Jain

👋 Let’s connect: YouTube · Skool · LinkedIn · Substack

I scheduled a team meeting to showcase the plan to my team. I remember being confident and hyped up about the whole strategy, and I thought the presentation would sail through.

But ten minutes into the meeting, one of the engineers on the team (who had, incidentally, just joined fresh out of college a few weeks ago) asked a question that I still remember word for word:

Confident as I was feeling at the time, I gave him the most predictable answer. I told him that we’re doing this for scalability and long-term maintanability of our platform.

On hearing my answer, I could notice that he didn’t fully get the logic, but he nodded slightly, and we moved on with the meeting.

Later that evening, I went back to my notes to find the real reason. Turned out, it was not about scalablity after all, but cost. If we continued with the old platform, we would run out of our infrastructure budget within a few months. Scalability was never a problem at all.

Since then, I’ve caught myself explaining something that I didn’t fully understand myself.

In this post, we will unpack the Feynman Technique, how it works, and how you can use it to catch the gaps in your thinking before you share them with your team and stakeholders.

Here’s what we will cover:

• Where the Feynman Technique Comes From

• The Four Steps

• Why This Is a Management Problem

• Applying the Feynman Technique in Practice

• The Plain-English Pass

• How This Plays Out in Real Teams

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

Where the Feynman Technique Comes From

The Feynman Technique is named after Richard Feynman, the Nobel Prize-winning physicist from the United States known for his many works in the areas of physics and quantum mechanics.

I had heard his name during my science classes back in school, and then again recently in the context of ‘learning’ styles.

The interesting fact that most people don’t know is that Feynman didn’t actually prescribe or create the Feynman Technique himself. The technique evolved out of the way he actually studied and worked.

From his young years, Feynman didn’t believe in “rote memorization”, which was actually the standard way of ‘teaching’ back in the early 1900s in schools (and is in fact still true today in many schools around the world).

He thought that just repeating a formula or a definition back over and over again without actually understanding it was a complete waste of his time.

So, in college, he kept notebooks where he rewrote and recaptured entire lectures from basic principles instead of copying them down word for word. That habit is also where his reputation as “The Great Explainer” came from.

He could take some of the hardest ideas in physics and break them down into plain language anyone could follow.

The Four Steps

The technique itself has four steps:

1. Pick the topic. It could be a decision, a plan, or a team strategy.

2. Explain it simply. Teach it as if you’re talking to someone who is brand new to the topic (like I would do to the new engineer on my team in the situation I shared at the beginning)

3. Find the gaps. Notice when you get stuck. For example, when you find yourself dropping a buzzword like “strategic alignment” or “synergy” that should be a signal to you that you’re now entering the edge of your own understanding of this topic, and that’s the gap.

4. Go back and fill the gaps. Go back to digging into the gaps, the data and the sources, and then explain it again (go back to Step 2).

Why This Is a Management Problem

Feynman used this technique to learn and teach physics.

And as a manager, you can use it to find out if you actually understand the strategy that you’re being paid to lead in your role.

Why is this important? Here are a few reasons:

• Jargon rarely helps clarify anything. I hope you’ll agree with me on this one, that most jargon and buzzwords are really there to cover gaps and hide from the real issue. “Aligning on strategic priorities” may sound like a plan, but when you dig deeper into the mechanics, more often than not, you’ll find that nobody has actually agreed on what to do first.

• The clarity of your thinking is directly proportional to the quality of your team’s execution. Think about this: if you explain something to your team in a fuzzy manner, do you really expect them to execute clearly? If your decisions aren’t crystal clear, do you really expect them to move forward without running into “wait, what did you actually mean by that” hurdles?

Applying the Feynman Technique in Practice

For the rest of this article, we will focus our attention on putting the Feynman Technique into practice in your own leadership role. As we do that, don’t forget to download the Feynman Technique Worksheet.

Use this worksheet to:

• Run any decision through the four steps before you present it to anyone else

• Spot exactly which phrase or claim is hiding a gap, instead of guessing at “communication issues”

• Build a plain-language version of your explanation you can actually reuse with your team

How to download the worksheet

This worksheet is part of the Worksheets Collection, available to all paid subscribers to The Good Boss.

• 👉🏻 Upgrade to paid now and get instant access to the entire collection, including this worksheet.

• If you prefer the standalone worksheet, you can purchase it from here.

Next, let's understand the simple technique you can use with your team to move from fuzzy to clear.

The Plain-English Pass

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I felt the same way every time I got promoted through my career - from an engineer to a manager to a director.

But in this piece I’m going to argue that promotions actually take something away from you, and for good reason.

And if you don’t let it go on purpose, it will take you down with it.

Here’s what I mean.

The promotion is sold as an addition, when it’s actually a subtraction.

Nobody promotes you and asks you to stop doing what you did before, right?

Recall the last time you got promoted at work.

Your manager congratulated you on the new responsibilities, the new title, and then likely left you to “figure things out” on your own.

Correct?

Let’s say that you were a software engineer who was technically strong and could solve the hardest problems thrown at you. And because of that, you got promoted to a “manager.”

Then, in this new role, you suddenly had a team to manage, a release to deliver, and you naturally stuck to your traditional “strengths”… which was to continue solving everything for the team.

And when you did that, here’s what happened: you ended up depriving your team members of the growth and learning opportunities, instead of creating more of them.

As another example, let’s say that you were an excellent manager and led your team from the front, and knew every detail of the org. So, naturally, you got promoted to director. Now, when you were trying to be “rigorous” and “in-touch” like you always were before, your teams thought that you didn’t trust them anymore.

That’s the subtraction I’m talking about.

The subtraction happened because you kept doing the job that got you the promotion, but didn’t realize that the new position actually needed something completely different.

And you know what’s the hardest part? This is really hard to detect, because your behavior typcially shows up as a “virtue”.

You tell yourself that “I care about quality”, or “I want to stay close to the work”, or “I hold the bar high”, etc. and those sound like great virtues to stick with, but they’re also the same things that are actually holding you back.

The higher you go, the harder it gets to see

When you’re junior in the corporate ladder - say, a software engineer, or an entry-level analyst - you usually get direct feedback. In your feedback conversation, your manager tells you “Gaurav, you need to delegate more,” and you start working on it right away.

But as you climb up the corporate ladder, things start to change rapidly.

Your colleagues, your stakeholders, your team members - they all start “managing up” instead of just talking to you. And before you know it, the honest feedback starts to dry up.

Your calendar gets filled up with meetings with people who are either telling you what you want to hear, or whose actual job is to keep you comfortable. Chiefs of Staff were supposed to keep their bosses honest and accountable, but I’ve seen that role degenerate into “filtering what the boss wants to hear”.

Here’s the trap:

I’ve been in meetings where our VP made a decision that most of us in the room knew was just wrong, but nobody said so. And it wasn’t because the people in the room were cowards, but because the last couple of times they pushed back, they didn’t get the response from the VP that they expected. So… they “adapted”.

And here’s the scary part: this trap compounds.

When you get less feedback, you become more certain and confident that “you’re right”. If you’ve ever seen a leader with a team that organizes itself around “not upsetting him”, that’s the trap, and it’s compounding in action.

The telltale signs

So, how can you tell if you’ve fallen into this trap?

The biggest sign is this:

A few examples:

• The new software manager who just can’t stop writing code himself (I used to be this!)

• The senior manager who reviews every presentation deck before it is sent out.

• The director who has to be in every decision made by the team

As discussed earlier, the justification for their behavior is tied to a virtue that’s, let’s fact it, hard to question.

They call it “high standards” or “being thorough” or “caring about the work”.

And there’s a second, more subtle sign:

A manager once told me that her team was “not taking ownership”.

She used to review and literally rewrite every plan that her leads put together. In her own eyes, she was “being thorough,” but in her team’s eyes she had never actually handed over any ownership to them at all.

That’s the telltale sign.

A quick checklist for you

So how do you find out which one is still running you?

Go ahead and pick up a pen and paper and spend 10-15 minutes answering them with honesty:

• What is the one thing on your team that you still refuse to hand off, no matter how good the reason sounds?

• If someone else did that thing and did it worse for a while, how does that make you feel, and why?

• What would you have to stop believing about yourself for that to be fine?

• Name the person (or persons) on your team whose growth is capped right now because you haven’t let this go.

• If you got promoted again tomorrow, what would you keep doing out of habit that the new role wouldn’t actually need?

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But a few months into the project, somehow both the teams find themselves building workarounds instead of finishing their side of the work that was agreed on properly.

Why did they do that? Because each team assumed that the other team would get delayed, or have bugs, or (most commonly) just change their spec without telling the other.

In fact, I’ve seen a similar scenario play out multiple times during my career having worked on cross-team and cross-divisional initiatives and projects. In most such cases, the teams weren’t “lying” or “lazy”. Not at all. In fact, they were extremely passionate about their work, and every decision they made seemed rational in isolation. But when you looked at the project holistically, it ended up shipping much later than originally planned, and that too with a ‘patched-up’ integration that in the end neither of the teams was proud of.

Most teams call this a communication problem, or a trust problem, but what’s really running it under the hood is the Prisoner’s Dilemma.

In this post, we will unpack what this phenomenon is all about, how it works, and how you can learn to counter it as a leader.

Here’s what we will cover:

• Understanding the Prisoner’s Dilemma

• How This Shows Up in Leadership

• Why this matters for leaders

• Applying the Prisoner’s Dilemma in Practice

• The Payoff Reset

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

Understanding the Prisoner’s Dilemma

I first came across this term during my MBA in the microeconomics class, and you may have heard of it in a similar context.

The Prisoner’s Dilemma was originally coined by Game Theory researchers at the RAND Corporation in the 1950s, in the context of the nuclear strategy during the Cold War.

Here’s how the original setup works:

• Two prisoners who are arrested together are held in separate rooms so they can’t talk to each other or coordinate.

• Each of them is given the same deal: either betray the other or stay silent and “hope” the other one stays silent and doesn’t betray you.

There are the possible outcomes:

• Both stay silent. If both stay silent (i.e., they cooperate), both get a lighter sentence because the prosecution can’t prove much without an actual confession. This is the best combined outcome for the two of them together. But here’s the catch: it only works, if each of them is able to ‘trust’ that the other one won’t betray him/her (i.e., defect), but since they’re in separate rooms and can’t actually talk to each other, neither of them can actually know that for sure.

• One betrays, one stays silent. When one of them stays silent, while the other betrays, the betrayer walks free, and here’s the pinch: the one who stayed silent takes the maximum sentence alone. Obviously, this worst case scenario is playing int he minds of hte prisoners as they make a decision. It is what makes betrayal a tempting option even if they don’t like it, because they don’t want to be the one left having to serve the maximum sentence alone. This outcome can happen in two ways, depending on who stays silent and who betrays.

• Both betray. When both of the priosoners betray the other, each of them get a moderate sentence, which is worse than if they had both stayed silent, but still better than the maximum sentence of hte worst case scenario above. If you think about this carefully, this might feel like the most rational option by default because betraying kind of protects you from the ‘maximum’ sentence.

Here’s an interesting challenge poster which shows just how broadly applicable this is, just for your curiousity:

How This Shows Up in Leadership

Now, let’s look at how the Prisoner’s Dilemma shows up in leadership. Here’s how you map it:

• Betraying becomes protecting my team’s plan (vs the shared plan)

• Staying silent becomes committing to the shared plan that was agreed upon with the other team

Consider ths scenario: A new project requires two engineering teams to work on different parts of the project. Paul’s team is building the front-end of the software, whle Melina’s team is build the backend services and APIs. The front-end layer calls the backend APIs, and both teams discuss and agree on a shared plan that includes the specific interfaces and the specs, so that they can work independently and still stick to the overall timelines.

If you run the same four scenarios through this scenario, here’s what you’ll get:

• Both teams cooperate: Paul’s team builds the front-end based on what was agreed, and Melina’s team builds the backend APIs to the agreed spec on time. This is the best combined outcome, but the one that only works if both sides are confident that the other will also stick to the spec and plan.

• Paul cooperates, while Melina defects: Paul’s team builds the front-end as per the plan and trusts the interface completely, but Melina’s team changes the spec mid-quarter without telling Paul. Paul’s team did everything right, but because of this unexpected shift, still gets burned.

• Melina cooperates, while Paul defects: in this case Melina’s team builds the back-end APIs as per the originally agreed spec, but Paul’s team made some assumptions and build a different front-end that is not compliant to the spec without informing Melina. In this case, Melina’s team burns when they discover the change.

• Both teams defect: both the teams build workarounds and diverge from the original spec, and when they finally meet, they find their implementations poles apart. This is the worst outcome because it requires the maximum rework.

Why this matters for leaders

Let’s now talk about why this matters, and importantly, what you can do about this as a leader.

While the payoff matrix we just saw may look like it’s “fixed” for the teams that are in the situation, it is actually not the same for a leader who is sitting above both teams in the hierarchy, or a stakeholder who is talking to both teams.

As a leader who has visibility into both teams, and power to influence their goals and priorities, you can change how often the teams meet and coordinate. You can also set processes that catch defections or silos that lead to them in the first place.

You can bring the teams together, outside of just the project alignment, so they get to know each other as humans first, which can help them to form the trust they need to start cooperating on such projects.

In Game theory, there are two types of games involved:

• One-shot games are harder to fix as they only involves “one” shot at the coordination or project. This is where the rational choice is typically deflection.

• Repeated games are those where the same teams work together again, and cooperation becomes the more rational choice, and it also becomes easier to build trust over time.

So, you might be wondering, what are some things you can do as a manager in such cases? Here are a couple of strategies that I’ve seen work well:

• Pay attention to the dynamics in the team - how they commit, how they coordinate with other teams, do they follow the agreed specs and terms, etc. Don’t just assume that ‘motivating’ the team will be enough for them to build trust with each other.

• Create a culture of visibility and transparency. For example, something as basic as a shared weekly sync meeting where both teams look at a dashboard of the project together could be enough to reduce the uncertainty, and discourage the teams from ‘assuming’ things about what the other team is doing.

Applying the Prisoner’s Dilemma in Practice

For the rest of this article, we will focus our attention on putting the Prisoner’s Dilemma into practice in your own leadership role. As we do that, don’t forget to download the Prisoner’s Dilemma Worksheet.

Use this worksheet to:

• Spot when your teams are stuck in a defect-defect situation

• Map what’s actually at stake in each outcome

• Turn a vague “trust issue” into a specific fix

How to download the worksheet

This worksheet is part of the Worksheets Collection, available to all paid subscribers to The Good Boss.

• 👉🏻 Upgrade to paid now and get instant access to the entire collection, including this worksheet.

• If you prefer the standalone worksheet, you can purchase it from here.

Next, let’s discuss a technique you can use right away if you notice your teams defecting against each other.

The Payoff Reset

Read more

As we looked at the slides, I remember seeing a lot of ‘reds’, and my team members were sharing the ‘path to green’. One of them suggesetd that we pause and redirect our resources somewhere else, while another was trying to push harder on the existing plan.

At that point, I remember thinking that my job wasn’t to pick a “winner” out of all the opinions, but to see what perhaps none of them were seeing yet.

That was the moment I understood what ‘strategic’ thinking actually means for a leader. Many managers think that strategic leadership is about “having a vision” and then driving towards that vision, but that’s a very narrow way of looking at it.

Here’s my take on strategic leadership:

Here are the six skills that I think are critical for any strategic leader, and how you can start building them today.

1. Pattern Recognition

Millie, an engineering manager I coached, once told me that two of her best team members had suddenly started missing deadlines. She noticed that they were also calling in sick more than usual.

Her first instinct was to treat each case separately: a coaching conversation with one, a direct Slack message to the other.

During our conversation, I asked her what she thought the two team members had in common.

As she thought about it, she said that both of them had been buried in the same painful legacy migration for the past six months. And as she said that, she relalized that the missed deadlines or sick days were likely not two isolated issues, but linked o the same underlying problem.

For example, a product manager at an established software company sees how youngsters are nowadays hooked to AI tools and ChatGPT (including his own teenage daughter), and uses that as a signal that is worth watching for rather than just noise that he can ignore. After all, these same people will soon become his company’s future customers.

Strategic leaders connect dots early, while everyone else is still looking at each incident individually.

How to develop pattern recognition:

• Ask “why” before jumping at a solution. You can use the 5 Whys framework (deep-dive link below) for a structured approach to arriving at the root cause or issue.

• Set aside time each month or quarter to look at your team’s or industry’s data, trends, etc. I like to do this every quarter with my leadership team.

• The Ladder of Inference is the clearest framework I’ve found for catching yourself jumping from a single observation straight to a conclusion. Deep-dive link below.

2. Systems Analysis

Early on as an engineering manager, I used to think of “my team” as its own little island. We designed and wrote code, we shipped features, and what happened in sales or marketing or finance was someone else’s business.

Many years later, I realized how narrow I was thinking. My team once worked on a new mobile app feature and published it to the App Store. We were really proud of it because it was really nicely designed and a lot of effort went into it.

But within a few days of the release, we were faced with the brutal truth: our customers didn’t really want this. The analytics told us that very few of our customers ever used that feature. It wasn’t their fault, it was ours: nobody on my team had talked to the people closest to the customer or what they were really looking for.

When you pull on one strand in that hypothetical web, you will notice how they’re interconnected. A seemingly innocent engineering capability you build can turn out to be connected to something sitting in a completely different division on the other side of your company.

How to develop systems analysis:

• Before you make a decision, take a step back and think of the spider’s web I referred to above. Ask what else it might be touching outside your own team’s boundary.

• Conway’s Law captures this really well: the systems you build end up mirroring the way your organization communicates. So, if your teams don’t talk to each other, your products won’t either. (deep-dive link to Conway’s Law below).

3. Mental Agility

Kat, an engineering manager leading an ecommerce portal, once led the launch of a new onboarding flow for their customers. She, along with her team, were confident about the success of this new flow, but when they looked at the analytics from the first few days, they were telling a different story.

As passionate as she was, Kat resisted the temptation to defend her team or to ignore what she was seeing. Instead, she pulled the analytics, lookaed at the drop-off data, and worked with her team to change course ASAP.

I’ve been leading teams for 20+ years, and I can say this with confidence: Nothing goes exactly as planned… projects fail, customers get angry, your most loyal team members leave… and the market shifts under you without any notice.

The leaders who stay strategic are the ones who treat an unexpected result as new information, not a verdict on their own or their team’s competence.

How to develop mental agility:

• Use the Premortem framework: imagine the project has already failed, then work backward to find out why. Deep-dive link below, if you want to try it out.

• Use the Inversion Principle, another framework I really like because it forces us to think differently about a situation, from a different angle. Deep-dive link below.

4. Structured Problem-Solving

I once observed a director, Matthew, who had acquired a completely new org that came with a “low morale” label attached ot it.

A typical manager could have guessed at a “fix” and perhaps rolled out a pizza party. Matthew didn’t do that. He took some time to get to know the new team, collect feedback, even reviewed attrition data by team, and mapped where the drop in morale actually started.

He soon discovered that the morale issue was tied to one team, under one specific manager. It wasn’t an org-wide issue, and while nobody would say no to free food 😅, a pizza party would have missed the issue completely.

How to develop structured problem-solving:

• Use First-principles Thinking, a structured framework to dig deeper and identify the underlying components of a problem (deep-dive link below).

• Try the Double-Diamond technique, another powerful framework to identify the exact problem you need to be solving (deep-dive link below).

5. Visioning

Many years ago, there was a major reorg across our company, which involved flattening of the hierarchy across the org.

I remember seeing two different managers handle the same reorg in very different ways:

• One manager was transactional, and explained it to his team as a “cost-cutting exercise.”

• The other manager explained the reorg as the first step toward a team that could finally ship without three layers of approval.

As you can imagine, they got completely different levels of energy from the respective team.

How to develop visioning:

• Use the Golden Circle, an excellent frameworked first coined by Simon Sinek, and focus on defining the Why before you get to the What and the How. Deep-dive link below.

• Set BHAGs, another powerful way to set bold, ambitious gols for your team that inspire and motivate them. Deep-dive link below.

6. Political Savvy

For most of my career, I used to hate politics. I thought good work should speak for itself and anyone who was trying to build relationships instead of output was just wasting his or her time.

Then, soon enough, I saw seemingly less capable people get promoted right in front of my eyes, and strong proposals get rejected by executives without any obvious reasoning. That’s when I realized the importance of relationships in building influence in the workplace.

I don’t want to deny that there is indeed a “dark side” to politics, but I’m not talking about that here. I’m talking about the side of politics that is a necessary skill for any strategic leader.

How to develop political savvy:

• Build relationships before you need them, not in the moment. If you want the full map of how office politics actually works, I wrote a detailed post on that in The Hidden Rulebook of Corporate Politics (link below).

• Recognize the realities of being a middle manager, including the secrets, regrets and guilty pleasures that come with it (deep-dive link below).

My Take

You’ve probably noticed this by now: none of the six skills I talked about in this post show up on your resume, or your LinkedIn profile.

You don’t put “pattern recognition” or “political savvy” on a job posting for a manager.

Yet, I would argue that these skills are more important than any technical or soft skill you may have been trained on.

If you agree with that, do give this post a like and subscribe to The Good Boss for more such content.

Subscribe to The Good Boss to get actionable strategies every Monday & Thursday, plus my ‘20 Essential Leadership Tools’ guide free when you sign up

💬 Join the conversations

Join The Good Boss community if you’re tired of leadership content that sounds good but doesn’t work when you’re actually in the room.

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The Good Boss by Gaurav Jain

👋 Let’s connect: YouTube · Skool · LinkedIn · Substack

It wasn’t the first time he had managed a reorg. In fact, it was his third time, and he had actually developed a 3-step ‘playbook’ that he was planning to execute this time:

• Have a clear checklist of tasks

• Assign owners for each task

• Set a two-week deadline for the alignment

This playbook had worked very well the last time when he had restructured his own team, and the entire change was completed in less than two weeks.

That wasn’t to be this time, though. This time, it took him six weeks to even notice that the plan wasn’t working. He later reflected that he was probably trying to solve this problem with a solution that was meant for a different kind of problem.

In this post, we will deep-dive into the Cynefin Framework, which is a powerful technique you can use to close that gap between the problem you think you’re solving and the problem you’re actually in.

I also have a whole chapter on this framework in my book, The Leader’s Playbook. If you’re interested, feel free to explore the book here.

Here’s what we will cover:

• Where Cynefin Came From

• The Four Domains

• Why Cynefin Matters for Leaders

• Applying Cynefin in Practice

• The Domain Check Technique

• Three Scenarios and how Cynefin plays out in them

• Common Pitfalls (and How to Avoid Them)

• Recommended Resources

• Final Thoughts

Ready to dive in? Let’s go!

Where Cynefin Came From

Cynefin was developed by Dave Snowden in the late 1990s while he was working at IBM. The name comes from a Welsh word roughly meaning “habitat” or “place of belonging”.

The core idea behind the framework is that the right response to a problem depends entirely on the habitat that problem lives in, not on how confident or experienced you are.

The Four Domains

Cynefin sorts problems into four domains, and the whole framework stems from one idea: each domain represents a different way of thinking, not just a different level of effort.

• Clear. In this domain, the cause and the effect are obvious and known. There’s also a well-known “best practice”, and you just need to apply it. It could be as simple as an onboarding documentation, or a standardized deployment process, or in current AI times, a spec file that runs the SDD (spec-driven development) workflow.

• Complicated. In this domain, the cause and the effect exist, but you don’t see them easily. You need a certain level of expertise to see them. Also, there isn’t one obvious answer, but there is a knowable range of good answers, and an expert can find one. Examples could be a complex architectural decision, or a legal question.

• Complex. In this domain, the cause and the effect are only obvious later, in hindsight. You don’t have an expert who can tell you the right answer up front, because the system itself changes as you act on it. Examples of problems in this domain are people-related, such as team morale, cross-org dynamics, or the reorg example that I shared at the beginning of this post.

• Chaotic. In this domain, there is no time to figure out the cause and the effect at all. You are time-pressured, and you don’t have the time to analyze it. Examples of problems in this domain could be a production outage, a safety incident, or a PR crisis.

Why Cynefin Matters for Leaders

I’m sure you’ve heard this many times from leadership gurus: if you want to be a good leader, you should be decisive, collaborative, and trust your gut.

However, Cynefin says that all of that advice is situational, and may not work in all situations.

For example:

• A leader who is great in a crisis situation because he is fast, decisive, and directive, may be a poor leader if thrown into a Complex people problem because there the agility and decisiveness will likely backfire.

• On the other hand, a leader who is careful and builds buy-in before every move, can literally freeze if thrown into a Chaotic situation because he doesn’t have the time to ask anyone what they think.

Have you noticed how the same manager can look like he’s doing a brilliant job with one problem, while being completely clueless with another problem? Or maybe found yourself in that situation?

That’s exactly why Cynefin matters for leaders, because it encourages us to act based on the situation or the domain, not just out of our expertise.

Applying Cynefin in Practice

So, how do you apply this framework in practice in your own leadership role?

I’ve put together a Cynefin Framework worksheet which walks you through step-by-step in applying this in your role.

Use this worksheet to:

• Diagnose which of the four Cynefin domains a real problem actually falls into

• Force a fast, honest gut-check (via the Domain Check)

• Commit to one concrete action, with a specific day and time, instead of a vague intention

How to download the worksheet

This worksheet is part of the Worksheets Collection, available to all paid subscribers to The Good Boss.

• 👉🏻 Upgrade to paid now and get instant access to the entire collection, including this worksheet.

• If you prefer the standalone worksheet, you can purchase it from here.

The Domain Check Technique

Here’s the technique I actually use, and I’m calling it the Domain Check. It takes about two minutes, and I run it before any decision that feels bigger than a routine one.

Read more

Most of the time those shortcuts are useful, but sometimes they’re not, and they can cost you a good hire or a high-impact decision.

The biggest challenge I find is that these shortcuts “feel like” judgment, so we rarely catch them in the moment. We just call them “instinct” or a “gut call”, and move on.

Here are fifteen of these cognitive biases that I’ve seen in 20+ years leading teams, and how you can avoid them.

Cognitive Trap #1: The Ostrich Effect

When things start going wrong, some leaders bury their head in the sand and hope the problem sorts itself out. That is the ostrich effect.

How this might be sabotaging your leadership

Let’s face it: avoiding a problem does not make it disappear. In fact, I would argue that it makes it more expensive.

Ironically, the ostrich effect keeps you from dealing with the things that actually need you even more:

• A conflict brewing between two engineers on your team

• A project that has slipped three times, yet you’re not paying attention

• A budget conversation with your boss that you keep pushing to next quarter

By the time you finally face the situation, the damage is already done, and is much bigger than it needed to be.

I have fallen for this as well. Early on in my career as an engineering manager, one of my team members was clearly not delivering against what was expected out of his role. And what did I do? I told myself that “he was probably going through a rough patch” and that “he would pull out of it”.

Obviously, he didn’t, and his performance got worse to the point that it impacted the rest of the team as they had to pick up his work. Two other team members started to feel the pressure, and what was supposed to be one conversation turned into three conversations.

Avoiding the trap

• Face issues head-on: The moment you notice a problem, deal with it there and then. My thumb rule is: early problems are small problems.

• Create a feedback culture in your team: Check in regularly with your team, your projects, and your metrics so you’re aware of the issues early on rather than discovering them later when they’ve grown into bigger ones.

• Get comfortable with hard conversations: Hard conversations are your job, not an add-on. If you avoid them, or delay them, you will lose trust and credibilty of your team. Period.

Frameworks to apply:

Cognitive Trap #2: Bandwagon Effect

You align your behaviour with what the majority of people around you are doing, not necessarily with what you truly want to do. This is the bandwagon effect.

How the bandwagon effect impacts your leadership

When you fall for the bandwagon effect, you’re following the trends without making your own judgment of what you actually want or need. If you run towards what is popular without checking whether it fits in your situation, you will likely miss better options and end up solving a problem your team never had in the first place.

I have seen this play out many times across companies, and now especially with AI. You watch a few viral posts on YouTube or X about a new AI tool, maybe three companies you admire acrtually adopt it, and suddenly you are rolling it out in your team too. Nobody asked whether the thing it fixes is actually broken on your team.

Three ways to avoid the trap

• Evaluate on the merit: Judge ideas on their merits and their fit for your situation, not their “popularity” or “virality”.

• Encourage critical thinking: Build a culture where people are expected to question popular opinion. First Principles Thinking is a strong approach here (see deep-dive link below).

• Encourage innovation and out-of-the-box thinking: Maybe the approach nobody is talking about is the one that fits your problem and your team needs to work on.

Frameworks to apply:

Cognitive Trap #3: Confirmation Bias

You go looking for information that supports what you already believe, and ignore anything that doesn’t. This is confirmation bias.

Impact of the confirmation bias

When you are falling for confirmation bias, you are not seeing the full picture. What you’re actually doing is collecting support for a conclusion you already reached in your mind. And this doesn’t stay hidden - your team sees it in your hiring decisions, promotion decisions, and every decision where you decided early and later selectively validated that decision.

Let’s say you have a pet project going, and you are convinced that it is going to be a great success. When your team presents the project status, you read the “green” status report closely, acknowledge and praise the team, and just skim past the ‘reds’ that were sitting a few slides later. That’s confirmation bias in action.

Here’s how you can avoid it

• Go looking for the opposite: Think of this as the reverse confirmation bias. Before you decide, make yourself find the case against your position. Look for the devil’s advocate on your team (there’s usually one in every team) and have a healthy conversation with them.

• Build psychological safety: Your team members and stakeholders will only tell you the thing you do not want to hear if it is safe to do that.

• Use inversion: Instead of asking how it will succeed, ask how it would fail. That flip is the Inversion Principle - deep-dive link below.

Frameworks to apply:

Cognitive Trap #4: Anchoring Bias

Think about the last big decision you made. Whatever number or idea you heard first probably influenced everything that came after. That is anchoring bias.

How anchoring impacts your leadership

Anchoring is very common in pricing pages or marketing campaigns. When you anchor yourself, you skew your decision towards a starting point or number that may have nothing to do with the decision at all.

I’ve seen this play out many times: Someone gives you a rough estimate for a project in a hallway conversation, off the top of his head. A few weeks later that estimate (or should I say, guesstimate) has found itself in the formal plan, and in a deck that you’re presenting to the VP, and nobody can remember that it started as a guess in the first place.

How to avoid it

• Don’t rush your decision: Take time to gather other perspectives, and then decide. System 2 thinking is the right mode here (see my deep-dive link below).

• Reframe the decision: Look for the alternatives and get a broader view.

• Get a second opinion: Bring in someone who was not in the room when the first number was dropped. This will likely remove the effect of the bias.

Frameworks to apply:

Cognitive Trap #5: Sunk Cost Fallacy

You have put time, money, and effort into something, so you keep going even though it’s clearly not working. That is the sunk cost fallacy.

The “cost” of sunk cost on your leadership

As a manager, part of your job is to know when to pull the plug. The sunk cost fallacy makes you hesitate at exactly that moment, and when you fall for it, you make the wrong decision.

I remember once a manager had her team work for eight months on a new product, and very few customers adopted or provided any feedback. The manager decided to continue to add more features to it for another quarter, because killing it felt like a failure. And what happened to it? They ended up killing it anyway later, with twelve months gone instead of eight.

Two ways to avoid the trap

• Focus on future value: Ask yourself what the best decision is from here on, and ignore what is already spent. The Impact-Effort matrix helps you sort this out (see deep-dive link below).

• Set clear “exit points”: Before you start, identify what would make you stop. Exit criteria written in advance are much easier to follow than exiting under pressure later on.

Frameworks to apply:

Cognitive Trap #6: Availability Heuristic

The availability heuristic is the shortcut where you judge a situation by whatever examples come to your mind first. In leadership, that means you overvalue things because they were recent, dramatic, or just easy to remember.

How this can sabotage your leadership

This bias plays out by diverting your attention to what is vivid from what is important.

Let’s say a vocal member of your team meets you in a 1:1 in the morning, and complains about something that catches your attention. That complaint sticks in your head, and when you go to your team meeting in the afternoon, you’re suddenly responding to everyone with that frame, as if that is a widespread issue.

Ways of dealing with the bias

• Use data, not anecdotes: Look for the actual numbers and hard evidence before you decide how big something is.

• Review long-term trends: Zoom out over quarters, not weeks. Most “big issues” will likely drop out of your view once you look at the bigger picture.

Frameworks to apply:

Cognitive Trap #7: Endowment Effect

You value things more highly simply because they are yours. This is the endowment effect.

The subtle ways this can impact your leadership

In a nutshell, the endowment effect makes you defensive about your own work. This comes from basic human nature: if you are attached to a process because you designed it, you will have a tendency to resist a better version someone else proposes.

I’ve also seen this show up with people and relationships. When a manager is closer to a particular individual on the team (maybe because of their tenure, or because they’re a high performer), he may have a tendency to overlook bad behavior by that person, while have a very different response to another person they’re not as close to.

Ways you can avoid it

• Get outside input: Ask stakeholders who have no stake in the thing you built for a more honest, unbiased opinion.

• Be open to change: Make it normal for your team to improve on your work in front of you - this tells your team that you’re not emotionally attached to your work and they shouldn’t be either.

Frameworks to apply:

Cognitive Trap #8: Groupthink

You have a strong, high-performing team, but somehow everyone in the room agrees with everyone else. That is called groupthink.

How groupthink sabotages your leadership

Groupthink, by its very nature, suppresses the counterargument or the opposing views from even showing up in your meetings.

The tell-tale signs of groupthink are:

• Instead of pressure-testing each other, everyone falls into agreement quickly.

• Nobody calls out the risks or challenges.

• Nobody shares “better” options

Let’s say you are in a planning meeting and propose an approach based on your point of view. Three people in the meeting agree to your proposal, and nobody else questions it because they think it will slow things down or make them feel awkward. Your approach may well be fine, but you will never know because nobody checked.

Two ways to avoid the trap

• Encourage disagreement: Say out loud that disagreement is expected, and remember to reward it when it happens.

• Assign a devil’s advocate: Give one person the job of playing the devil’s advocate and question the popular approach.

Frameworks to apply:

Cognitive Trap #9: Halo Effect

Someone in your team impresses you once, and after that everything they do looks “good”. This is the halo effect.

How the halo effect shows up in leadership

The halo effect is very common in leadership, and in the corporate environment, this is generally called favoritism.

Let’s say someone on your team ran a difficult migration successfully two years ago, and since then that person has been your “go-to person” for everything. Good so far, but when that same person misses a deadline today, you tend to overlook it, but if someone else on the team does the same, you mark it in their performance notes. That’s the impact of the halo effect.

How you can deal with the trap

• Focus on current behaviours: Assess people on what they are doing on the current project, not on a highlight from two years ago.

• Separate likeable from effective: Some people are indeed easy to work with, but that doesn’t make them effective for the job.

Frameworks to apply:

Cognitive Trap #10: Recency Bias

Recency bias is the tendency to put more weight on what just happened compared to everything that happened before it.

Impact of the recency bias

In a nutshell, the recency bias makes the last two weeks “stand in” for the whole year.

I remember once, one of my team members delivered well above expectations for nine months of the year, and then he had a bad sprint in October. When I started the annual performance calibration process in November, his sprint performance was overshadowing everything else he had delivered in the year, and I had to work really hard not to let that happen.

A couple of ways to deal with it

• Look at long-term trends: Zoom out and look at the longer-term picture. Mind Boxing is a framework I built to help balance short-term reaction against longer-term thinking (deep-dive link below).

• Set review checkpoints: I like to do quarterly reviews so it provides regular points of assessment vs a single check at the end of the year.

Frameworks to apply:

Cognitive Trap #11: The Dunning-Kruger Effect

We have all met someone who is completely confident about himself in an area where he actually knows very little. That is the Dunning-Kruger effect.

The dunning-kruger effect in action

Dunning-Kruger is one of those suble traps that hides your own gaps from you. You make calls on false confidence and never uncover your blind spots.

And if you don’t pay attention to it, it can also distort how you assess your team members. You may end up promoting those who are confident, even when they’re less impactful than others.

Ways to handle the bias

• Know your blind spots: Map your gaps by asking for feedback from those who work with you. The Johari Window is an excellent framework to identify those blind spots (deep-dive link below).

• Promote based on impact and results, not confidence or visibility: Confidence is not the same as competence. Learn to dig deeper to tell the difference before you make any promotion decision. Deep-dive into the Dunning-Kruger trap below.

Frameworks to apply:

Cognitive Trap #12: Projection Bias

You assume other people think and feel the way you do, even when they don’t. That is projection bias.

Projection bias in action

Projection bias plays out in very suble ways, and that’s why I think it’s also quite dangerous.

When you fall for the projection bias, you assume that you already know what someone wants, so you never ask, and then end up making decisions that weren’t needed or correct in the first place.

How you can avoid it

• Listen actively: Check in with people about what they want, not just what they are working on. Your team member working on a project doesn’t automatically imply that they like working on that project.

• Ask for feedback: Test your assumptions against what others tell you, not just what you assumed to be true.

Frameworks to apply:

Cognitive Trap #13: Self-Serving Bias

You credit your successes to your own skill and blame your failures on circumstances. This is the self-serving bias.

How self-serving impacts your role as a leader

Self-serving bias, by its very nature, breaks your ability to accurately assess yourself. And when you can’t assess yourself, you can’t improve.

In leadership, it looks like this: when a project is successful, you talk about the decisions you made, the teams you coached, the impact you had on the project, etc. But when it gets delayed, you suddenly turn your attention to external factors, and start talking about the market, the timeline, and the dependency on the “other team” that led to the delays.

And when you do this, your team notices this pattern much faster than you think. It teaches them that credit flows up and blame flows down.

Avoiding the self-serving bias

• Have a servant leadership mindset: Look at your role as serving your team, not owning your team by applying the Servant Leadership mindset. Check out the deep-dive link to this framework below.

• Ask for honest feedback: Make it easy for people to tell you where you got it wrong on a regular basis.

Frameworks to apply:

Cognitive Trap #14: Illusion of Control

You overestimate how much of the outcome you actually control. This is the illusion of control.

I wrote about this in Confessions of a Middle Manager: Secrets, Regrets and Guilty Pleasures (linked below), where the gap between how much control managers think they have and how much they really have is the whole story.

How middle managers can get trapped

The illusion of control, in effect, produces risky decisions, and you end up making plans that have little or no contingency.

If you believe you can fully control your team’s output and results, you may not pay attention to the brewing tension between team members, the issues with the CI pipeline, or even the lack of engagement in the team. And all those things will likely result in a decline in your team’s output and results eventually.

Avoiding the illusion

• Acknowledge what you can’t control: Name the factors you can’t control, then plan around them instead of ignoring them.

• Manage risk deliberately: Have a real approach to spotting and mitigating risk. The Animal Risk Matrix lays out a structured approach to manage risk (deep-dive link below).

Frameworks to apply:

Cognitive Trap #15: Hindsight Bias

Once you know how something turned out, it starts to feel like it was always going to turn out that way. This is hindsight bias.

When you get trapped in hindsight

Hindsight bias makes you judge your or others’ past decisions more critically than they deserve.

For example, when a project fails, it may look obvious in hindsight. And you may conclude that you “should have seen it coming earlier”. But you’re ignoring the fact that back then you didn’t have all the information you have now. When you judge an old decision with new information, it actually doesn’t help you to decide better next time.

How you can avoid it

• Document decisions: Write down what you knew and what you assumed at the time, not now.

• Use the Premortem Technique: A structured way to assess risk on a project before it happens is the Premortem Technique, which I discuss in a deep-dive (link below).

Frameworks to apply:

In Summary: Avoiding the Cognitive Traps

Here’s the full list of cognitive traps we reviewed in this post, for your quick reference:

1. The Ostrich Effect: you avoid the problem because facing it is uncomfortable, and it gets bigger while you wait.

2. Bandwagon Effect: you adopt what is popular without checking whether it’s really needed.

3. Confirmation Bias: you collect proof for the conclusion you already reached in your mind.

4. Anchoring Bias: the first number you hear pulls every number after it, subconsciously.

5. Sunk Cost Fallacy: you keep investing resources and energy because of what you already spent, not because of what you will get from here on.

6. Availability Heuristic: the most memorable example wins, even when it is not the most common one.

7. Endowment Effect: you overvalue the process, the idea, or the person because it is yours, not because it’s truly valuable.

8. Groupthink: everyone agrees fast, and the argument or opposing views that could have improved the decision never happen.

9. Halo Effect: one strong impression by a person changes and influences how you judge everything else that person does.

10. Recency Bias: what you see happen in the last two weeks influences how you think of the entire year that just passed.

11. The Dunning-Kruger Effect: you are most confident in the areas where you know the least.

12. Projection Bias: you assume your team wants what you want, so you never ask.

13. Self-Serving Bias: you take credit for the wins, and attribute the losses to the circumstances or external factors.

14. Illusion of Control: you build a plan assuming you have full control over things you actually don’t.

15. Hindsight Bias: once you know the outcome, it feels like it was always obvious.

💬 Which of the traps above have you found yourself or your team fall for most often? Drop it in the comments below!

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I wasn’t feeling quite convinced about that approach, and so I asked a couple of clarifying questions, and then just said “okay, let’s take it offline,” and moved on. I thought I was being reasonable in how I handled it.

A few days later, in a meeting with another engineer who was part of that meeting, he told me that the team had read that meeting as me “killing” the idea.

Frankly, I was shocked to hear that.

That’s the part of emotional intelligence we don’t talk about.

In 20+ years leading teams, I’ve seen so many leaders equate emotional intelligence with being nicer to people. I used to think the same, until I realized that being emotionally intelligent is not about being nice, but about being accurate.

• Accurate about what you’re feeling.

• And, accurate about what the other person is feeling.

Then, and only then, would you truly be “emotionally intelligent”.

In this issue, I’m going to deep-dive into the EQ Framework, the model behind emotional intelligence, and how you can use it as a leader. Here’s what we will cover:

• The Origins of Emotional Intelligence

• How the EQ Framework works

• Why This Matters for Leaders

• Applying the EQ Framework

• The Four-Corner Check Technique

• What This Looks Like in Practice

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

The Origins of Emotional Intelligence

The term “emotional intelligence” was introduced by two psychologists, Peter Salovey and John Mayer, in their 1990 paper.

Then, in 1995, Daniel Goleman wrote a book called Emotional Intelligence, which arguably made it popular among the leadership community in general. You’ve probably read or heard about this book, too.

The framework has evolved since it was last published, and the part that I find most interesting for leaders is the 2x2 matrix - the EQ Framework - that we will talk about in this issue.

Goleman claimed that at senior levels, EQ predicts leadership effectiveness better than IQ or technical depth. So what is the difference between EQ and IQ? I think the following toon sums it up nicely:

How the EQ Framework works

The EQ framework is built around two axes:

• Who: Are you working on yourself, or on other people? Self or Social.

• What. Are you noticing something, or acting on it? Recognition or Regulation.

It involves leaders being aware of the four quadrants:

• Self-awareness (Self × Recognition): catching your own emotions as they happen, not in the car on the way home after the fact. Think emotional self-awareness, honest self-assessment, and self-confidence.

• Social awareness (Social × Recognition): reading the room and the person in front of you, not just hearing them. Think empathy and organisational awareness.

• Self-management (Self × Regulation): doing something useful with what you noticed. Think self-control and adapting to situations.

• Relationship management (Social × Regulation): acting on what you read in others. Think influencing others, developing your team and others around you.

Why This Matters for Leaders

Emotional intelligence applies to everyone, not just leaders, but I think the stakes are much higher for leaders. Here’s why.

Your mood gets louder when you’re the boss.

Let’s say on a particular day, you’re feeling mildly annoyed, maybe a 3 out of 10. If one of your team members is mildly annoyed with you, you would barely notice (unless you’re super sensitive, of course!)

But remember that you are the person who writes their performance review, who decides their promotion, and what project they work on. So your “3” feels more like an “8” to them.

• The sigh you didn’t know you made after their comment in the meeting.

• The one-word reply you dropped to their long Slack message.

• The Zoom camera you kept off, while they had theirs on.

To you, none of it was a big deal, because you know it wasn’t about “them”.

Your team copies you.

As a manager, you’re not just managing your own reactions. You’re setting the tone for everyone in your team.

Whatever you do with pressure, how you handle conflict, how you set the standards… your team learns to do the same.

• If you stay steady when a launch goes wrong, your team will stay steady.

• If you get stressed and short-tempered, likely they will do the same with each other.

Your “read” on your team turns into decisions.

Again, rememer that as a manager, you decide who in your team is ready for more, who is struggling, and who to put on a hard project.

And how do you decide all that? A big part of it has to do with how you read your team members.

If you get that read wrong, you will make poor decisions that may impact someone’s career, financial situation, or worse, their self-confidence and sense of worth.

The real cost is silence.

The real cost of not being emotionally aware is much bigger, in my view.

Every small reaction you have, however minute you might think it was, teaches your team about what is safe to bring to you.

If your replies are sharp, or you ignore them completely, they will learn to stop telling you things early. They will probably wait until they’re sure it's worth bringing it up to you. Maybe they will wait until they have a ‘solution’, not just the ‘problem’.

So even without you noticing, you stop hearing the real issues when you should.

This is why I think EQ is not “soft”. It’s actually what powers your team’s operations - how they think, how they work, and how they communicate.

So in that sense, EQ directly impacts your bottom line - your results, your KPIs and your customer satisfaction.

Applying the EQ Framework

For the rest of this article, we will focus our attention on putting the EQ framework into practice in your own organization. As we do that, don’t forget to download the EQ Framework Worksheet.

Use this worksheet to:

• Name what you’re feeling in one specific word

• Rate all four quadrants against real moments, not self-image

• Find your weak link, and fix it upstream

• Run the Four-Corner Check Technique on a live situation

How to download the worksheet

This worksheet is part of the Worksheets Collection, available to all paid subscribers to The Good Boss.

• 👉🏻 Upgrade to paid now and get instant access to the entire collection, including this worksheet.

• If you prefer the standalone worksheet, you can purchase it from here.

The Four-Corner Check Technique

Here’s the technique I use, and it takes under a minute.

Read more

As I walked up to him after the panel ended, I noticed his lanyard. It said “Head of Strategic Initiatives and Transformation.” It was quite a mouthful with 6 words, and I asked him what he actually did.

He smiled and said he was responsible for “stakeholder alignment, cross-functional orchestration, and strategic enablement.”

After trying to decipher that for a few seconds, I asked again, more directly this time: “What exactly are you responsible for?”

At that point, he froze. His polish, which he’d been carrying for the past 1+ hour, suddenly disappeared. He looked over my shoulder, mumbled something about needing to find someone, and suddenly walked off.

As I was driving back home from the fair, I reflected on what happened.

I realized that he wasn’t the only one. I’ve spent 20+ years in tech leadership, and I have observed that the leader’s job has been split into two parts: the identity and the work.

So how can you know if you are doing the same? Here are 8 signs I’ve seen again and again to watch out for.

Sign 1: Your title takes longer to say than your job does

Just look at any org chart in a large company, and you’re likely to find a small army of “Heads of Transformation,” “Directors of Enablement,” and “Leads of Innovation.”

If you ask three different people what any of them actually own, you’re likely to get three different answers, or a long pause (like the one I got at the career fair).

Truth be told: I am guilty of this myself. Several years ago during a reorg which was meant to flatten our hierarchy, I created a number of new titles: Tech Lead, Program Lead, Functional Owner, and a few more.

I remember feeling “empowered” for a few months, but soon enough, I realized the mistake. The sprint planning meeting now had three “leads” in the room, and none of them wanted to own the roadmap.

Permission lets you speak in the meeting, but real power is something you build by making decisions and living with the outcome of those decisions.

👉🏼 Takeaway: If you can’t say what you’re accountable for in one sentence, your title is doing the work your job should be doing.

Sign 2: You’re closer to the VP than you are to the work

Throughout my career, I’ve noticed people with fairly ordinary jobs who carry themselves like executives. And they do this purely because they report to someone senior.

In such cases, it seems that their proximity to power becomes its own badge, and it has almost nothing to do with what they actually deliver.

So how can you tell such people apart? Just ask them what they delivered this quarter, not who they had lunch with. If the answer is fuzzy, you can be sure that their “seniority” is borrowed, not real.

👉🏼 Takeaway: Sitting near power isn’t the same as creating value. The former gets noticed, but the latter is what gets results.

Sign 3: You have three buzzwords for your job and zero outcomes

I’m sure you’ve heard these a gazillion times, in broadcast emails from leadership after a re-org, merger, or in promotion announcements.

• “Driving transformation.”

• “Enabling alignment.”

• “Accelerating outcomes.”

All those words sound polished, but they’re equally vague, and they’re intentionally built to sound important without saying anything.

So why do so many people fill their vocabulary with buzzwords? Because making decisions is risky, and one of the risks is becoming unpopular. So they decide to hide behind buzzwords and vague language.

👉🏼 Takeaway: It’s easier to sound important than to do something that might be risky. Buzzwords are how you hide behind the risk.

Sign 4: Your meetings settle nothing, and everyone’s relieved about it

I remember observing two people on the team spend two weeks debating whether a button in our product UI should sit in the “top-right” or the “bottom-left”.

Both of them had strong opinions, but neither had real ownership. And guess what - the feature got scrapped eventually.

When I thought about it later, I realized that the real issue wasn’t even the button. The real issue was fear - nobody wanted to make the call and risk being “wrong”, so the team “performed collaboration” instead of making a decision.

👉🏼 Takeaway: A meeting that ends with “let’s take this offline” for the fourth time isn’t “collaboration”. It’s two people avoiding a decision that needs to be made.

Sign 5: You’ve hired more people to manage communication than to build the thing

At one point in my career, I realized we had more people coordinating between teams than people actually shipping the product.

From one angle, it may have looked like “structure” - organized and process-oriented. But in reality, it was just confusion and chaos.

Again, I’m guilty of creating some of those roles myself. I thought that bringing them in would bring some structure and order in how we work as a team. But what we ended up building was nothing but a maze that we weren’t able to find our way out of.

👉🏼 Takeaway: If your coordination layer is growing faster than your output, you’re not managing complexity. You’re manufacturing it.

Sign 6: You end the day exhausted and can’t point to what you actually did

There were several times in my career where I would log off every evening completely drained and exhausted. I would have gone through 10+ meetings, “enabled”, “facilitated”, “reviewed” all day, and yet couldn’t name a single thing I had actually accomplished on that day.

Through the day, I would discuss decisions, but wouldn’t make any.

👉🏼 Takeaway: Motion isn’t the same as movement. You can be busy all day and still have nothing to show for it by dinner.

Sign 7: “Busy” is your proof that you’re leading

You’ll recall what happened in 2020, when the COVID-19 pandemic swept the planet.

When offices shut down and people started working from home, a lot of people found out that their full-time job took three or four hours to actually do. The rest of the day went to “signaling”: green dots on Slack, back-to-back calls on Zoom, status updates on email, etc.

But who are we to blame? We built this ourselves:

• We schedule the meetings.

• We ask for the updates.

• We reward the person who’s always visible over the one who’s just doing the work.

👉🏼 Takeaway: A packed calendar makes you visible, but it doesn’t prove that you’re valuable.

Sign 8: Your best people have stopped pushing back

It always amuses me when a manager thinks he is one step ahead of his team.

Your team isn’t a bunch of kids. They’re grown-up people, and they know exactly when a meeting is just theater. They notice when “momentum” and “alignment” are just code words for your lack of courage to actually decide.

The brutal reality is that, at first they play along, but then they stop playing.

Leaders who “perform” confidence usually think they’re building trust, but they’re doing quite the opposite. The moment your team senses you’re performing instead of deciding, they lose trust in you, and eventually, respect in you.

👉🏼 Takeaway: If your best team members are silent, it may not mean “engagement”. They might just be giving up on you.

The good news

Okay, time for some good news :)

For years, this performance worked because the “props” were expensive.

• Preparing a polished deck took hours.

• Building an elaborate dashboard took days.

• Coordinating a meeting took real effort.

So working on them made it look like “real” work.

But today, AI has taken all that away. PowerPoint decks that used to take days now take minutes, and reports that used to justify an entire role can be spit out of a single ChatGPT or Claude.ai prompt.

What is left today is the part AI can’t do: judgment, courage, clarity, and owning the outcome when it goes wrong.

And those are exactly the things real leadership is all about. That’s the good news.

My honest take

I find that the hard part is the unlearning of old habits.

I still catch myself doing it from time to time: Spitting out buzzwords to sound “strategic”, waiting for “alignment” before I decide, and so on.

Real leadership is actually simpler than that, and frankly more uncomfortable (and who said leadership was easy?)

💬 So, which of these 8 signs hit closest to home for you? Let me know in the comments. 👇

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If you found this post helpful, please like and share it with other managers who can benefit from it, including your boss :) If you have any feedback, please drop your comment below - it helps me keep improving the content. Thank you!

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The Good Boss by Gaurav Jain

👋 Let’s connect: YouTube · Skool · LinkedIn · Substack

As the meeting was coming to a close, one of the team members floated the idea that “we should ship it two weeks ahead, in 6 weeks”, and a couple of others supported that with “sure”. I watched everyone around the room, and didn’t see any disagreements, so I piled on with “let’s try it”. And that was it. The decision was made, and the meeting was over.

Over the next few days after that decision, in separate 1:1s, three different people on my team told me that they weren’t quite sure about the timeline. All of them were in the meeting, but not one of them had said a word in the room. Each one told me a similar story.

What was interesting for me was that none of them “lied” in the meeting, or got pressured by someone else’s loud voice. Each of them privately assumed that they were the only one with a different opinion, so they chose to keep quiet.

And that’s how a team of smart, honest people ends up committing to a plan that, individually, none of them wanted.

This was an example of the Abilene Paradox in action.

In this issue:

• Understanding the Abilene Paradox

• How the Abilene Paradox Works

• How This Is Different From Groupthink

• Applying the Abilene Paradox in Practice

• The Reluctance Check

• The Reluctance Check in Action

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

Understanding the Abilene Paradox

The Abilene Paradox was introduced by management expert Jerry Harvey, who told a story about his own family, as illustrated below:

On a hot afternoon in 1974 in Coleman, Texas, a family member suggested an idea: let’s drive to Abilene for dinner. The rest of the family members agreed, and they went ahead with the 50-mile-long drive to Abilene.

The drive turned out to be hot, dusty, and the meal was nothing more than mediocre. On the drive back, when the family started discussing how horrible this idea was, it came out that nobody had actually wanted to go. Each person assumed the others were excited about it, so they went along wanting not to be the spoil-sport.

How the Abilene Paradox Works

The Abilene Paradox breaks down into three steps, and they happen almost at the same time:

1. Private doubt. Someone in the group has a real hesitation about the idea on the table. It’s not a strong objection, just a “hmm, not sure about this.”

2. A wrong read on the room. That same person looks around, sees everyone else looking calm or nodding along, and concludes that they’re the only one who feels this way. What’s actually happening is that everyone else is making the same wrong read, at the same time, about each other.

3. A rational choice to stay quiet. Given that they believe that they’re the only one in doubt, they decide not to raise any concerns, and stay quiet. After all, why be the one person who blocks something everyone else clearly wants? So they say yes, the next person does the same calculation and says yes, and before you know it, the group arrives at a decision that nobody actually agrees with.

The most subtle, and dangerous, part of the Abilene Paradox is this: nobody in the room is being dishonest or spineless. Each person is making a reasonable decision based on the wrong assumption about what everyone else believes.

How This Is Different From Groupthink

I’ve seen managers confuse the Abilene Paradox with Groupthink, which is another common trap, so I want to draw the distinction.

• Groupthink is what happens when a group actively suppresses real dissent to protect harmony. Someone in the room has a real, strong objection. They can point to exactly why they disagree, but they choose not to raise it because they’re afraid of the repercussions. There is real disagreement in the room, but it’s just being held back by pressure, or a desire to avoid conflict. The fix for groupthink is mostly about psychological safety: making it safe for people to voice their objection.

• The Abilene Paradox is different because nobody is holding anything back out of “fear” or a lack of psychological safety. Each person holds a doubt, but it’s not a strong objection. It’s not “I disagree, but I’m scared to say so.” (That’s groupthink) It’s closer to “I have a nagging feeling, but everyone else looks fine, so it’s probably just me.” The fix in this case is making everyone’s private hesitation visible to everyone else at the same time, before the group locks in on the wrong direction.

This is what makes the Abilene Paradox dangerous. A team can have excellent psychological safety, yet still run into the trap of the paradox.

Applying the Abilene Paradox in Practice

For the rest of this article, we will focus our attention on putting the Abilene Paradox into practice in your own organization. As we do that, don’t forget to download the Abilene Paradox worksheet.

Use this worksheet to:

• Turn a fast, easy “yes” into a real check instead of an assumption

• Surface the one hesitation everyone is privately holding but not saying

How to download the worksheet

This worksheet is part of the Worksheets Collection, available to all paid subscribers to The Good Boss.

• 👉🏻 Upgrade to paid now and get instant access to the entire collection, including this worksheet.

• If you prefer the standalone worksheet, you can purchase it from here.

The Reluctance Check

Here’s a simple technique that you can apply to counter the Abilene Paradox in your team:

Read more

The only difference is that nobody bothers to write them down in a management training.

At least, I never had these handed down to me. I learnt them through observation over several years leading teams and driving results. I’m sure you have seen them, too.

In this issue, I’ll share the nine that changed how I lead. I’ve written full deep dives in this newsletter for most of them, linked below if you want to go deeper.

1. Goodhart’s Law

“When a measure becomes a target, it stops being a good measure.”

Elena was an engineering manager at a mid-size fintech startup. Her org started tracking “story points completed per sprint” as the main measure of the team's health. Within a few weeks of this new process, the story point estimates started going up across every team. It was the same work, just larger numbers.

Elena later told me she didn’t notice it happening until she compared velocity numbers across two quarters, and realized that her team wasn’t actually shipping faster. Instead, they had just learned to game the numbers.

Key takeaway: Measure outcomes that are hard to game, or a combination of measures that together represent the key goals such as shipped features, customer impact, or retention. Don’t measure proxies or vanity metrics that are easy to game.

Read the full deep-dive on Goodhart’s Law and how to counter it below ⬇️

2. Parkinson’s Law

“Work expands to fill the time available for its completion.”

Marcus ran a platform team at a large tech company. He gave his team three weeks to migrate a legacy service. Three weeks later, it was done… right on schedule, with no surprises.

Then a security issue was reported by a high-profile customer, and it forced the same migration onto a different team, with four days’ notice instead of three weeks.

The team completed the migration and shipped in four days.

Marcus told me that was the moment he stopped trusting his own estimates. The work wasn’t actually three weeks of work. It was more like 3-4 days of work with three weeks of padding built in, because that’s how much time was available.

Key takeaway: Give a task less time and watch how much of the original estimate was actually just slack. Tight deadlines are often just honest, not unreasonable.

Read the full deep-dive on Parkinson’s Law below ⬇️

3. The Pareto Principle

“Roughly 80% of your results come from 20% of your efforts.”

Noor managed a product team at a growth-stage startup and once tracked every meeting on her calendar for a month. Then, she rated each meeting with the actual impact of it on the roadmap. Out of around forty meetings on her list, she counted six that had actually been impactful towards their goals.

The other thirty-four of them, like status updates, quick-syncs, check-ins, etc. felt productive in the moment, but they didn’t really help move the team forward. Most of them could have been done asynchronously on Slack.

That’s the Pareto Principle (or 80/20 rule) in action. After this realization, started asking, before accepting any recurring meeting, whether it was the 20% or the 80%.

Key takeaway: Rank your last ten decisions or projects by actual impact, not effort. You’ll almost always find two or three that mattered enormously and a long list that didn’t.

Read the full deep-dive on the Pareto Principle below ⬇️

4. Brooks’s Law

“Adding people to a late software project makes it later.”

Diego was leading a project that had slipped two sprints behind schedule. His director’s instinct was to pull two engineers off another team to help catch up. Diego pushed back, but got overruled, and the two engineers were added to the team to help out.

Two weeks later, the project was further behind than before the new engineers joined. These new engineers needed onboarding, getting accustomed to the new team’s ways of working, and just getting to know everyone. The existing team ended up spending a lot of their time explaining the context and background, and less on writing code. What looked like more hands turned into more meetings.

Key takeaway: Before adding headcount to a late project, ask whether you’re solving a capacity problem or a coordination problem.

5. Conway’s Law

“Organizations design systems that mirror their own communication structure.”

Wei led the backend team at a software company that had just split into two independent teams, one owning checkout, one owning fulfillment. These teams had separate meetings, separate processes, and separate communication channels.

When the product was shipped, customers noticed the checkout flow felt like a different product from the fulfillment tracking, when really the experience should have been seamless and cohesive.

Wei fixed it by bringing the two teams together by merging the standups, and integrating the communication channels. He didn’t even touch the architecture - it automatically adapted to the new change.

Key takeaway: Don’t ship your org chart. Organize your teams based on the capability or experience you intend to deliver to your customers, not the other way around.

Read the full deep-dive on Conway’s Law below ⬇️

6. The Peter Principle

“People rise to the level of their incompetence.”

Fatima was the strongest individual contributor on her team. She was the engineer everyone went to with the hardest bugs or issues. For her manager, the natural next step was to promote her into management.

Six months later, after being promoted to manager, she told me she missed writing code and that she wasn’t sure she was actually good at the new job yet.

The mistake was one that most, if not all, managers make: they assume that the only reward for being excellent at one thing is to hand them a different thing.

Key takeaway: Promotions should be a bet on a different skill set, not a reward for the old one.

Read the full deep-dive on the Peter Principle below ⬇️

7. Amara’s Law

“We tend to overestimate the effect of a technology in the short run and underestimate the effect in the long run.”

Owen’s team adopted Claude Code as the AI coding assistant as soon as it launched to the public. From there on, the expectations on what this tool could do were sky-high. In fact, some people on the team thought it would replace half their headcount by the end of the quarter.

A year later, Owen told me that the tool had completely changed how the whole team worked, by changing what junior engineers spent their first six months learning. Nobody was talking about it as a big deal anymore. It just was how the team worked now.

Key takeaway: Don’t panic when a new tool falls short of the hype in month one, and don’t get complacent just because it stopped being exciting. The real impact usually shows up later than everyone expects.

Read the full deep-dive on Amara’s Law below ⬇️

8. The Dunning-Kruger Effect

“People with low ability tend to overestimate their competence, while people with high ability tend to underestimate theirs.”

Ravi was about to promote an engineer, Liz, on his team based mostly on how she showed up in meetings (confident, decisive, always ready with an answer). Meanwhile, his strongest coder, Mark, who actually shipped the hardest features, sat in the same room, somewhat reluctant to speak up.

Ravi told me he almost made the call to promote Liz, but he stopped and asked a harder question: was he rewarding the person who sounded most sure (Liz), or the person who was actually best at the job (Mark)?

Key takeaway: Don’t promote or reward the loudest voice in the room by default. Confidence is easy to see. Competence is harder to notice, but is actually what you need to look for.

Read the full deep-dive on the Dunning-Kruger Effect below ⬇️

9. The Bannister Effect

“Once one person proves a limit was never real, everyone behind them moves faster.”

Simone managed a cross-functional team where junior engineers never pushed back on senior leads, even when they’d clearly spotted a real problem. It wasn’t a rule or culture code written anywhere. It was just how the team had always worked.

One sprint, a new hire, Tanuja, flagged a flaw in a senior engineer’s rollout plan in front of the whole team. Simone made a point of thanking him publicly, right there in the meeting, and said the team needed more of exactly that kind of thinking.

Simone told me that one moment did something magical in the team. Within a month, two more junior engineers raised concerns they would normally have kept to themselves. Nobody told them to… the mental barrier they previously had was no longer there because they had seen that this was possible in the team.

Key takeaway: Your team’s beliefs change when they see something happen, not when they hear you ask for it. Go first, do it visibly, and celebrate the next person who follows.

Read the full deep-dive on the Bannister Effect below ⬇️

In Summary

In this article, we discussed the nine laws that have changed how I lead.

1. Goodhart’s Law: When you turn a measure into a target, people optimize for the measure, not the outcome it was supposed to represent.

2. Parkinson’s Law: Work expands to fill however much time you give it. Less time doesn’t mean less gets done — it just means less padding.

3. The Pareto Principle: Most of your results come from a small slice of your effort. The skill is finding which slice is actually doing the work.

4. Brooks’s Law: Adding people to a late project usually makes it later, not faster, because new people need ramping up before they add any speed.

5. Conway’s Law: Whatever you build ends up looking like the way your teams talk to each other. Product seams usually trace back to communication seams.

6. The Peter Principle: People get promoted based on their last job, not their next one, so eventually everyone lands somewhere that stretches past what made them great.

7. Amara’s Law: We overestimate what new tech will do in the short term and underestimate what it’ll do over the long term. The hype fades before the real impact shows up.

8. The Dunning-Kruger Effect: People with low ability tend to overestimate themselves, and people with high ability tend to underestimate themselves. Confidence and competence rarely line up.

9. The Bannister Effect: Once one person breaks a mental barrier and everyone watches it happen, the barrier stops holding anyone else back either.

💬 Let me know in the comments: which of these laws have you seen show up in your team most often?

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• The Rollout Nobody Noticed

• Understanding Amara’s Law

• The Two Mistakes

• Applying Amara’s Law in Practice

• The Two-Horizon Check

• How This Plays Out in Real Teams

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

The Rollout Nobody Noticed

In 2024, I introduced GitHub Copilot, one of the first popular AI coding tools, to my team.

I’ll be honest - initially, I was skeptical, and so was my team. Some of the engineers tried it for a week and went back to typing code by hand. I remember one of them telling me, half-joking, referring to it as a “fancy autocomplete”.

Initially, the adoption was slow, and I started feeling like I had pushed the team toward something that wasn’t really helping.

Then, a few months later, I introduced Cursor, and later, Claude Code. By this time, the quality of the code and the reliability of these tools had dramatically improved. I saw adoption picking up, slowly at the beginning, and fast later.

Fast forward to today, and my entire team is using Claude Code or Cursor for pretty much all their engineering work, including coding, testing, documentation, and even full spec-driven development workflows.

I’ve noticed this pattern before. Whenever I introduce something new to the team, such as a tool, a workflow, a process, it tends to go the same way, almost every time.

Turns out, there’s a name for this phenomenon, Amara’s Law, which is exactly what we will discuss in this post. We will discuss how it works and how you can leverage it as a manager.

Ready to dive in? Let’s go!

Understanding Amara’s Law

Amara’s Law was introduced by Roy Amara, who was a researcher at the Institute for the Future.

Roy’s idea was simple:

In plain terms: the hype and the reality move at different speeds, and they cross at a point almost nobody is watching for.

When a new technology is introduced, expectations are high at first. I remember feeling the same when I first got my hands on an iPod (for those of you old enough to remember that!) in the 2000s. I thought I could carry my whole music collection everywhere and never touch a CD again!

Then, as I started using my brand new iPod, I faced the reality behind the hype. My iPod skipped exactly when I didn’t want it to, and the battery died too quickly for my tolerance. I remember thinking that I should just switch back to the good old Sony Walkman.

But behind the scenes, the tech kept getting better. I upgraded to the next generation of iPods over the course of the following years. The storage was bigger, synching got faster, and the battery life improved. Most people, including myself, had already stopped paying attention by then. And then one day, nobody was talking about it anymore - we just had our whole music library in our pocket.

The iPod wasn’t a gadget anymore. It was just how you listened to music.

Two years ago, I’d say my team was somewhere between those two points with AI tools… past the hype phase, but still in the trough. If you’re driving AI adoption in your team right now, you’re probably in that same spot.

The Two Mistakes

I’ve found that most leaders make one of two mistakes when something new comes up, like a new technology or a new capability.

• The Hype Mistake. This is when you are overexcited about something, too soon. For example, if you’re excited about the impact of AI, you tell your VP that AI will cut delivery time in half by next quarter. But when actually executed, it doesn’t happen. Now every claim you make is seen with more skepticism.

• The Dismissal Mistake. This is when you’re over-cautious or skeptical. For example, if you’re skeptical about AI and see it as a ‘fancy autocomplete’, you decide just to sit it out and not introduce it into your team. Then, a few months in, it gets a lot better and hard to ignore.

I’m sure you’ve noticed that both of these mistakes are nothing but two sides of the same coin.

Applying Amara’s Law in Practice

For the rest of this article, we will focus our attention on putting Amara’s Law into practice in your own organization. As we do that, don’t forget to download Amara’s Law Worksheet.

Use this worksheet to:

• Decide whether a stalled tool or change effort is actually failing, or just in the trough before it takes off

• Catch yourself before you promise a timeline you can’t back up

• Get honest about whether your team’s pushback is about today’s version or an old, weaker one

How to download the worksheet

This worksheet is part of the Worksheets Collection, available to all paid subscribers to The Good Boss.

• 👉🏻 Upgrade to paid now and get instant access to the entire collection, including this worksheet.

• If you prefer the standalone worksheet, you can purchase it from here.

The Two-Horizon Check

Use this simple technique to catch yourself making the Hype or Dismissal mistake, and to move towards the more practical decision whenever you see something new.

Read more