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

The Good Boss by Gaurav Jain

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

• 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

• The Company That Raised $1.75 Billion and Still Couldn’t Ask One Question

• Understanding the Premortem Technique

• Why This Works (The Psychology of Hindsight, in Advance)

• Why This Matters for Leaders

• Putting the Premortem into Practice

• The Failure Memo

• How This Plays Out in Real Teams

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

The Company That Raised $1.75 Billion and Still Couldn’t Ask One Question

Just a few years ago, in April 2020, a streaming app called “Quibi” was launched with much fanfare. I remember reading about it in the news at the time - that they had spent close to $1 billion of its $1.75 billion raised by the third quarter of that year.

This startup had a top team, seasoned executives, and a clear, simple idea: short, premium videos meant to be watched on your phone, when you’re in line, on the train, or between meetings. (source: NBC News)

Six months later, I remember seeing the news: it shut down.

Apparently, they had raised nearly $2 billion in funding, but failed to gain subscribers, and the founders shut the business down.

Here’s the part that bothered me when I first read this: the two biggest reasons it failed weren’t “hidden”.

• The whole idea depended on watching videos in short bursts while on the move. And as we all know, in 2020, the world faced the COVID-19 pandemic, and during that time, nobody was commuting anywhere. At least, I wasn’t.

• It also had a design flaw: I’m sure you’ll agree that most people usually watch something while doing something else, and Quibi’s mobile-only format didn’t let anyone do that.

While we can argue that the pandemic may have been hard to ‘predict’, it wasn’t the first pandemic the world faced, and certainly may have been sitting on someone’s mind as a possibility to call out. Also, it’s hard to believe the design assumption didn’t raise any concerns among their top-class design team.

Both of those were the kind of thing someone in the room almost certainly thought, and probably didn’t say. (source: MediumIndieWire)

That moment has a name. It’s called a “premortem”, and that’s what we will talk about in this issue.

Understanding the Premortem Technique

The premortem was introduced by cognitive psychologist Gary Klein, who published the idea in a 2007 Harvard Business Review piece.

Klein had spent years studying how professionals such as firefighters, ICU nurses, and military commanders made high-stakes decisions under pressure, and he noticed something peculiar:

Standard risk assessment usually happens before a decision, when nothing is settled, and everyone is still speculating. Klein’s insight was to move the exercise to a different dimension.

Here’s what he suggested:

That one shift changes everything about the quality of the answers.

• Traditional risk assessment produces a list of hedged possibilities: “there’s some risk the timeline might slip” or “we should probably keep an eye on adoption.”

• A premortem produces something closer to a confident explanation: “The timeline slipped because we never accounted for the compliance review, and by the time we caught it, we were already three weeks behind and cutting testing to compensate.”

Klein also observed that once a plan is already underway, raising doubts starts to feel like disloyalty, like you’re the one person who “didn’t get on board”. It feels riskier to raise doubts or concerns once things are “in flight”. I certainly have felt that way when wanting to raise concerns about a project that’s 80% done.

The beauty of the premortem technique is that it removes that cost. The discomfort of opposition disappears because what’s being asked for is a story, not real opposition.

Why This Works: The Psychology of Hindsight, in Advance

If you think about it, premortem isn’t just a nicer way of asking the same question. It fundamentally changes what people are psychologically willing to say.

• The traditional “What could go wrong” calls for hedging, because you’re speculating about a future nobody wants to be blamed for jinxing.

• “It already failed, tell me why” invites something closer to confident hindsight.

It also gives the skeptical person in the room permission to say what they were already thinking. They don’t need to be cautious of being called out as the “pessimistic” one. After all, they’re not objecting to the plan, they’re just answering the prompt they were given.

On a lighter note: this whole exercise reminds me a little of Final Destination (one of my favorite movie series). In the movie, someone sees the disaster coming in vivid detail before it happens. The only difference is, in this version, you’re actually allowed to change the outcome! :)

Why This Matters for Leaders

As leaders, we make decisions that impact the business, the teams, and the culture. And many times those decisions can be misguided or simply wrong.

The confidence tax

The more senior, well-funded, or publicly committed a plan is, the more expensive or risky it becomes for any one person to raise a doubt about it.

By the time the plan reaches higher up the chain, it’s often been pre-sold internally, which means the leadership isn’t evaluating it anymore… they’re just validating it.

Silence gets mistaken for agreement

When a leader asks the team “any concerns?” after presenting a plan, silence usually means buy-in.

But the reality could obviously be very different. Your team could be doing the math on whether raising a concern is worth the cost. After all, who wants to miss their chance at a big raise or that much-awaited promotion?

Hindsight is honest; foresight is polite

If you ask your team what went wrong with last year’s failed initiative, I guarantee that you will get sharp, specific, occasionally brutal answers.

But if you ask them what might go wrong with this year’s new one, you’ll most likely get hedged, generic ones.

Smart teams fail for ordinary reasons

It’s tempting to treat high-profile failures, such as the Quibi case we discussed earlier, as “complicated”.

In reality, usually, they’re not.

Quibi didn’t fail because of some crazy market dynamic. It failed because a core assumption they made (“people will make dedicated time for short videos on their phones”) turned out to be wrong, and nobody stress-tested that assumption before it was too late.

Putting the Premortem into Practice

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

Use this worksheet to:

• Turn vague concerns about a plan into specific, actionable risks

• Call out doubts your team is too polite to say out loud

• Catch untested assumptions before they become expensive mistakes

• Assign real ownership to risks instead of just naming them

How to download the worksheet

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

• 👉🏻 Upgrade 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 Failure Memo

Here’s the working version of the technique, built for a real team meeting, and you can run it in about thirty minutes.

Read more

I’ve re-read it a few times since, and realized again and again that I’d missed the point entirely.

Jim Collins and his research team studied companies that went from average performance to sustained market dominance, and asked a simple question: what did the good-to-great companies do that others didn’t?

In this issue, I’m sharing with you some of my key takeaways from this book, especially as they relate to modern leaders.

Ready? Let’s go!

Level 5 Leadership

Imagine two executives get assigned to run the same struggling division.

• Oscar, the first executive, takes the stage at the all-hands, thanks the board for “believing in his vision,” and spends the first month restructuring the org chart around himself.

• Grace, the second executive, spends her first month in back-to-back 1:1s with her new team, mostly asking questions and understanding the root causes. And when the team hits their big win, she stands up in front of all and says, “This was the team’s effort, not mine.”

Eighteen months later, Oscar’s division is still waiting for him to make every decision. Grace’s division doesn’t need her in the room to make a good one.

I’ve managed this wrong in both directions.

Early in my career, I confused humility with softness. I under-claimed decisions that were genuinely mine to own, which just made me look unsure. The fix wasn’t more ego, but getting comfortable taking the hard calls and giving away the credit for the good outcomes, on purpose, every time.

Level 5 isn’t about being modest as a leader. It’s about redirecting your ambition and drive at the mission, not at your ego.

First Who, Then What

Here’s a mistake I made for years: I’d get budget approval for a new role, and immediately start writing the job description - the “what.” Collins would tell you that’s backwards.

Wei, an engineering manager, ran a platform team that was drowning in tech debt. Instead of hiring a “senior backend engineer with 5+ years in distributed systems,” he hired Mei - someone with less specialized experience but a track record of making every team she joined sharper. He decided he would figure out what she’d actually work on after she joined.

Compare that to Diego, another engineering manager, who spent three months writing the perfect job spec for a role, hired exactly to that spec, and then watched the company strategy shift a few months later… leaving him with the right skills for a job that no longer existed.

Strategy and priorities change. The quality of the people sitting next to you is what actually determines whether you survive the turn when it arrives.

This is uncomfortable advice in a world of exact job ladders and leveling guides.

But the best hiring decisions I’ve made were never about matching a checklist. They were about whether I’d want this person on the team no matter what the team ends up doing.

Confront the Brutal Facts (Without Losing Faith)

Two managers at a large tech company get the same brutal news: the flagship product they’ve spent two quarters on is being cut.

• Fatima calls an all-hands and says, “This is a huge win for the team. We learned so much, and I’m confident the next thing will be even bigger.” Her words are positive, but her team isn’t exactly moved by them. After the news, many of them start updating their resumes, because everyone in the room knows BS when they hear it.

• Tariq calls his team together and says, “We built the wrong thing. Here’s exactly why, here’s what I missed, and here’s what we’re doing next.” His team is broken for a week, but they’re also grateful for the honesty. Slowly, they rebuild trust, because Tariq just proved he’ll tell them the truth even when it’s ugly.

The leaders who confronted reality without losing faith outlasted the leaders who did one but not the other. In fact, blind optimism has killed as many people as despair has.

At work, this means creating a climate where the truth is heard, not managed or softened. If your team only tells you good news, you’ve trained them to lie to you, and you’ll find out the brutal facts exactly when it’s too late to act on them.

The Hedgehog Concept

Nina and Aisha are engineering managers at a mid-scale company.

• Nina’s team said “yes” to everything: a client integration nobody else wanted, an internal tool three other teams were also half-building, and a side project that “might be big.” A year later, they’d shipped a lot and mattered very little.

• Aisha’s team, one floor down, said “no” to almost everything that didn’t fit their expertise or passion. A year later, her team had shipped very little and mattered a lot.

Collins calls the discipline behind Aisha’s choices the Hedgehog Concept, named for the old parable of the fox, who knows many things, and the hedgehog, who knows one big thing and does it supremely well.

For a manager, this is the difference between a roadmap that’s a wish list and a roadmap that’s a bet. Most teams don’t fail due to a lack of ideas, but due to refusing to say no to good ideas that aren’t the “right” idea.

I recent wrote a dedicated piece on the Hedgehog Concept, and how you can apply this concept as a leader in your own team and role. Check it out below.

Culture of Discipline

In a financial tech company, two teams both claim to value “ownership.”

• Leo’s team has a “values” poster on the wiki and a rule for every process: approval chains, sign-off meetings, a manager checking every ticket before it moves.

• Sarah’s team has almost no rules, but everyone on it independently makes the call Sarah would have made, because they’ve internalized why the standard exists, not just what it is.

This one reframed something for me.

I used to think adding more processes was the right move whenever something went wrong. Half the time, it was actually a signal that I hadn’t hired, trained, or trusted the right people to make the call without me.

Technology Accelerators, Not Saviors

This is one many of us are facing first-hand these days with the emergence of AI.

In a large tech company, two teams get access to the same new AI coding tool - Claude Code.

• Tom’s team treats the tool as the strategy. “AI-first” becomes the whole plan in and of itself. After a few months, nobody in the team can explain what specifically got better, only that “everyone uses the tool now”.

• Devi’s team already had brutal clarity on their bottleneck in the SDLC process. Their code review turnaround was killing their velocity, and they used the AI tool to attack that one problem directly. They automated code reviews, added specs to make sure their best practices were followed, and ensured that the quality bar remained high and consistent. In just a month, they noticed that their cycle time actually improved by 2x.

I watch this pattern constantly right now with AI tooling specifically. The teams getting real leverage aren’t the ones with the most tools enabled. They’re the ones who knew exactly what was broken before they picked one up.

If this format resonates with you - a book, broken down into what you can actually as a manager - hit reply and tell me. It’s still new, and it shapes whether I keep doing these.

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The Flywheel, Not the Doom Loop

I’ve seen this one play out many times, and I’m personally guilty of it too.

Consider two equally smart, capable managers - Chris and Mona - both working at a large tech company. When AI and AI tools started gaining popularity, both Chris and Mona knew this wasn’t something they could ignore. It was a big shift in technology, and they need to stay ahead of it.

• Chris wanted the turnaround for his team to feel dramatic. So he called and all hands with his team and announced a new mission and even a new name for the team. He called them “AI Trailblazers”. Great name and definitely inspirational, but fast forward three months, there wasn’t much of a shift in the actual product or processes the team was working on. So what did Chris do? He announced a different new mission. Eventually, his team learned to wait him out instead of believing him.

• Mona, while equally excited about AI, never made any big announcement in her team all hands. She decided to go slow and steady - one small shift at a time. She started with AI tool adoption, followed by experimentation sprints, and integrating them into their workflows. She made the small, boring, compounding decisions that nobody outside the team would have noticed individually. A few months later, her team’s ability to leverage AI, and deliver real value to their customers, had skyrocketed. People up the chain, and in other teams, started asking what her “big strategic move” had been. There wasn’t one.

What Mona had adopted was what Collins calls the Flywheel: enough consistent, disciplined pushes in a single direction that builds momentum towards something bigger and more valuable. From the outside, this can look like a breakthrough.

What Chris was doing was the opposite - the Doom Loop. He was jumping from initiative to initiative, program to program, leader to leader, never staying still long enough for any single push to compound.

If you’re waiting for the one big swing that turns your team around, here’s the bad news: it’s probably not coming. The good news is that you don’t need it to.

Putting It Together

The way I see it, the seven ideas we discussed from Good to Great build on each other in roughly three layers.

1. Level 5 Leadership and First Who, Then What are about who’s in the room and who’s steering.

2. Confront the Brutal Facts and the Hedgehog Concept are about seeing clearly what matters for you and the organization.

3. Culture of Discipline, Technology Accelerators, and the Flywheel are about execution - turning clarity into years of compounding, boring momentum.

Found this summary useful? Do reply to this email or drop a comment so I know what’s resonating and what’s not. Also, if you want me to write about any specific book of your interest from a leadership lens, let me know.

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The Good Boss by Gaurav Jain

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

• The Email That Ruined my Afternoon

• The Ladder of Inference

• The Six Rungs

• How This Shows Up for Managers

• Putting the Ladder Into Practice

• The Rung Check Technique

• How This Plays Out in Real Teams

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

The Email That Ruined my Afternoon

A few years ago, I was putting together a proposal for a new project I felt strongly about. It was genuinely excited about it and put in real effort into building the case: why it mattered and the data to back it up.

I made sure that I was thorough enough so there was nothing left to poke holes in.

Finally, that Wednesday afternoon, after reviewing it a few times, I attached the deck to an email to my manager, and hit send, full of anticipation.

My manager’s reply came back within the hour: “Let’s discuss.”

That was it. No “great idea,” no “let’s talk logistics,” not even a question mark. Just two words and a full stop.

I spent the rest of that afternoon dismantling my own proposal in my head.

• Maybe the data wasn’t as strong as I thought.

• Maybe he saw a flaw I’d missed.

• Maybe this was the polite version of “no.”

I then started rehearsing how I’d defend it when I do get to ‘discuss’ it with him.

The next morning, he pulled me for a quick chat in the office kitchen, and it turned out to be nothing like what I was preparing for. He said he loved the idea, and just wanted five minutes to talk through timing before he took it to his boss.

That was the entire “discussion.”

The email didn’t ruin my afternoon. The version of it I wrote in my head did.

The Ladder of Inference

Here’s the strange part: nothing about the situation actually changed between “Let’s discuss” landing in my inbox and the conversation the next morning with my boss.

The facts didn’t change, but only my reading of them had changed, from two neutral words into an entire verdict about my idea.

That gap has a name.

It’s called the Ladder of Inference, developed by organizational psychologist Chris Argyris and later popularized by Peter Senge in The Fifth Discipline.

In my case, I didn’t react to my manager’s words “Let’s discuss.” I reacted to a belief about what those two words meant that I had constructed in about ninety seconds.

The Six Rungs

Here’s what climbing the ladder actually looks like, rung by rung, using my own email as the example:

1. Observable Data. What actually happened? If there were a CCTV camera, what would it have captured? My manager typed “Let’s discuss.” That’s all that happened.

2. Selected Data. What data was selected (i.e., filtered)? I noticed the message was short and lacked enthusiasm. I didn’t notice that he’d replied within the hour, which likely meant he’d actually read the whole thing closely.

3. Interpreted Meaning. What’s the meaning you attach to what you selected? In my case, “No enthusiasm” became “he found a problem with it.”

4. Assumptions. What assumptions did you make? We generally fill gaps with beliefs we already hold. I already carried a quiet worry that my proposal was more ambitious than practical, so the gap got filled with that.

5. Conclusions. What was the conclusion? The assumptions harden into a verdict: “He’s going to say no, or water it down.”

6. Beliefs. What is the belief based on the conclusion? The verdict became a standing belief for the rest of the afternoon that this idea was probably dead on arrival.

7. Action. What action was taken? I acted on the belief: rehearsing my defense, bracing for pushback, without ever thinking twice.

The climb takes seconds. Coming back down takes a conscious decision to look again.

How This Shows Up for Managers

I’ve seen the Ladder of Inference show up in many forms for managers.

• In feedback conversations. A flat tone in a review is inferred as resistance when it’s often just fatigue or nerves.

• In cross-team friction. “They’re blocking us on purpose” is almost always an assumption based on a minor observation, usually a missed Slack message or a different set of priorities.

• In remote and async work. Less context means less real data to select from, which means faster climbs to the wrong inferences. A delayed reply, a short message, a camera-off call - they all get filled in with whatever story is easiest to tell.

Putting the Ladder Into Practice

For the rest of this article, we will focus our attention on putting The Ladder of Inference into practice in your own team or organization. As we do that, don’t forget to download The Ladder of Inference Worksheet.

Use this worksheet to:

• Pause before a tense 1:1, when a tone or short reply feels bigger than it probably is.

• Slow down on a cold-sounding message, like a flat Slack reply, email, or delayed response.

• Catch a snap judgment before it shapes a promotion call or performance read.

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 Rung Check Technique

Here’s a simple technique I like to use: before you act on a conclusion, find the rung where you left the facts.

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The title and cover told me it was a communication skills manual, the kind of thing HR hands you in a binder you never open again.

Then I hit the chapter on the “Path to Action” and had to put the book down for a minute, because it described, almost exactly, a conversation I’d botched with a direct report just a few months earlier.

It wasn’t the words I said, but the thinking that led me to say them. That’s the thing about Crucial Conversations by Joseph Grenny et al.

This is the second post in the book-summary format I started with The 7 Habits last week. Same idea: I’m not recapping the book, I’m translating it into what you can actually use the next time a conversation at work gets tense. If you like this format, I’d love to know if there are any books you would recommend I read and distill like this.

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When a Conversation Turns “Crucial”

Imagine two managers, Diego and Hannah, get blindsided in the same way: a peer of theirs - Martin - takes credit for their team’s work in front of the leadership group.

• Diego, the first manager, feels his face go hot, says nothing in the room, and spends the next three days building a case in his head. He replays the moment dozens of times, drafts the email he’ll never send, and convinces himself that Martin “always does this.” By the end of the week, he’s cold in every meeting they’re both in, and nobody knows why.

• Hannah, the other manager, feels the same heat as Diego. But she does something Diego didn’t: she tells herself that this is now a crucial conversation. She recognizes the high stakes, the differing opinions about what actually happened, and the real emotion in the room. She doesn’t say anything in the meeting either, just like Diego, but she books fifteen minutes with Martin that same afternoon, before the story in her head has time to harden into a verdict.

You can’t wing a crucial conversation the way you’d wing a status update.

Start with Heart

Here’s a scenario every manager has lived: a 1:1 conversation with someone underperforming, where you walk in already right.

Marcus, a manager at a tech company, has been dreading this one for two weeks. He walks into the 1:1 with Pooja, having mentally rehearsed exactly how he’ll prove that her performance gap is real, with key numbers loaded and ready to spill out, and ready to win the argument. Fifteen minutes in the 1:1, Pooja is defensive, and the meeting is unidirectional. At the end, Marcus leaves the meeting thinking “I said everything I meant to say” as if that’s the win condition, even though it left Pooja feeling misunderstood and miserable.

Elena, another manager at the same company but a different division, has a similar conversation the following week with her direct report, Chris. Before she walks in, she asks herself the question the book calls Start with Heart: what do I actually want here for myself, for Chris, and what do I not want? She realizes that what she really wants is for Chris to actually improve, not for herself to be “right”. That reframes the entire 30 minutes of the 1:1 that follows.

Learn to Look

The book has a phrase for the two ways crucial conversations go wrong, and once you learn it, you start seeing it everywhere:

• People turn to silence, or

• People resort to violence.

Tom, an Engineering Director at a fast-growing startup, is in a planning meeting where the roadmap he built gets quietly gutted by a VP two levels up. What does Tim do? He nods, says “makes sense,” and goes silent for the rest of the meeting with no pushback, no questions, nothing. Everyone reads this as agreement, but it’s actually withdrawal.

Renu, another Director at the same company, is in a different meeting with the same VP, and her proposal is torn apart by the VP. What does Renu do? She doesn’t go quiet. Instead, she goes sharp: she starts pulling up her “backup slides” with hard data and numbers, stacking her arguments, and waits for the VP to respond to them. She maintains eye contact, and stays visibly engaged and alert. Everyone reads this as confidence.

Master My Stories

This is the section that stopped me cold the first time I read it, because it names something I do constantly and rarely catch myself doing.

Ben, an engineer on a scrum team, notices Farah, his peer, hasn’t responded to his Slack message in four hours. By hour two, he’s decided she’s ignoring him on purpose. By hour three, he’s decided this is part of a pattern: she doesn’t respect his time. By hour four, he’s cold with her in the team standup, and she has no idea why, because she was in back-to-back interviews all afternoon.

The trap is that steps two and three happen so fast that you experience them as just facts. Ben didn’t feel like he was making up a story. He felt like he was just reacting to reality.

Make It Safe

Every manager has a version of this (myself included): a conversation where the content of what you’re saying is completely reasonable, but somehow the other person shuts down anyway.

Leo, an engineering manager, tells Kelly, an engineer on his team, that a client complaint came in about a missed deadline. He does this calmly and factually, with nothing accusatory in his wording. Kelly, however, immediately becomes defensive, starts explaining, and then goes quiet mid-sentence and disengages for the rest of the conversation. When Leo leaves the meeting, he wonders, “I didn’t even say anything harsh… why did that go so badly?”

Vikram, another engineering manager, has almost the same conversation with his own report, Pat, a month later. Before he gets to the complaint, however, he opens with something the book calls Mutual Purpose: a quick, genuine signal that she’s on this person’s side, not against them: “I want to figure this out together, not build a case against you.” The message is still hard, but the reaction is very different because the safety was established before the content landed.

Once safety is restored, you can say almost anything. Without it, even a gentle sentence feels like an attack.

STATE Your Path

Delivering hard feedback is where most managers either go too soft to matter or too hard to land.

• Aisha, a marketing manager, needs to tell a peer that his part of a joint project is consistently late, and it’s making her look bad to their shared stakeholder. She opens with three minutes of cushioning: “this might be nothing, I’m probably overthinking it, feel free to ignore this”, and, unsurprisingly, by the time she gets to the actual point, it’s so buried the peer doesn’t register it as a real issue. Nothing changes.

• Chris, another marketing manager, has a similar conversation with his peer. He uses what the book calls STATE: he (s)hares the facts first (not the story): “the last three deliverables came in after the agreed date”. Then, he (t)ells the story he’s drawn from those facts: “I’m starting to worry this will affect how the stakeholder sees the whole project”. Then, he (a)sks for the other person’s view, and (t)alks with genuine concern to invite pushback rather than shut it down. The message lands as direct but not as an attack, because the facts came before the judgment.

Move to Action

The most common failure mode in leadership isn’t a bad conversation. It’s a good conversation that goes nowhere, because nobody closed the loop. Sound familiar?

Nadia, an engineering manager, runs a retrospective session with her team. There’s good energy in the room, real insight popping up, and everyone agreeing to a plan to fix the handoff process between two teams. However, two weeks later, nothing has changed because the meeting ended with a vague “let’s all be better about this” with no owner, date, or follow-up.

Oscar, also an engineering manager, runs a similar retro the following sprint with his team. The discussion is productive, just like with Nadia, but he ends it the way the book insists every crucial conversation should end: who does what, by when, and how will we follow up.

If this format of book insights for modern leaders resonates with you, please hit reply and tell me. I would love your feedback and suggestions.

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Putting It Together

The ideas from Crucial Conversations stack into three simpler questions you can actually hold in your head:

1. Before the conversation: is this actually crucial (high stakes, differing views, real emotion), and what do I really want here? That’s Learn to Look and Start with Heart, your prep work, done before you walk in.

2. During the conversation: am I noticing when I or the other person shift toward silence or violence, am I checking my story against the facts, and is this still safe for both of us? That’s Learn to Look again, Master My Stories, and Make It Safe, your real-time diagnostics.

3. Delivering the message: say the hard thing using STATE, and don’t leave without a decision. That’s the closing pair of STATE Your Path and Move to Action.

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The Good Boss by Gaurav Jain

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

• The Escalation That Wasn’t Really Ours to Fix

• Understanding The Eisenhower Matrix

• Why Urgent Always Wins (Unless You Interrupt It)

• Putting the Matrix Into Practice: The Worksheet

• A Simple Habit: The Friday Filter

• How This Plays Out in Real Teams

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

The Escalation That Wasn’t Really Ours to Fix

A few years back, we’d just wrapped annual planning. The roadmap was locked, the team was in full execution swing, and everyone knew what they were building and why.

Then, mid-Q2, my VP dropped a note: a customer escalation needed a look. The customer had emailed our CEO directly, not once, but twice, and was loud about it. I got on a couple of calls to understand the actual concern.

They were convinced one of our existing platform features was “buggy.” In reality, it wasn’t our bug at all - it was a Windows-side issue.

But the CEO and VP were watching, and the noise was real, even if the root cause wasn’t. So we made the call: pause the roadmap, pull one of our teams off planned work, and build a “fix”.

To be honest, I wasn’t fully on board in the moment. But the pressure was real, the audience was senior, and I went along with it anyway.

It worked, in the narrow sense that the customer went quiet. Phew! But we’d spent real engineering time solving a problem that was never actually ours, at the direct cost of the plan we’d just spent weeks building.

Looking back, I regretted how easily “the CEO is watching” overrode “this isn’t actually our bug”, and how long it took me to even ask that second question.

Urgent had a sponsor, Important didn’t, and that’s usually all it takes.

Understanding The Eisenhower Matrix

The Eisenhower Matrix is named after Dwight D. Eisenhower, who is said to have said:

Stephen Covey later popularized it as a 2x2 tool in The 7 Habits of Highly Effective People. I talked about this in my previous post, in case you want to check it out.

In plain terms, every task sits somewhere on two axes:

• How urgent it is

• How important it is.

When you cross those, you get a 2x2 grid:

• Urgent + Important: Do. The outage, the exec escalation, the thing with a deadline today, and real consequences if you miss it.

• Important, not Urgent: Schedule. The roadmap, the coaching conversation, the strategy work. Nothing bad happens today if you skip it. Something bad happens in six months if you keep skipping it.

• Urgent, not Important: Delegate. Most meetings. Most “quick” requests. Loud, but low-stakes if handled by someone other than you.

• Neither: Delete. The stuff that survives purely on habit, the recurring sync nobody remembers agreeing to, the report nobody reads.

Two of these boxes look almost identical from the inside of a busy week: Do and Delegate both feel urgent, same adrenaline, same “I need to handle this now” pull. The only real difference is whether it actually requires you specifically, right now, or whether it just landed on you because you were “reachable”.

The other confusion runs the other way: Schedule and Delete both feel optional in the moment, because neither is shouting at you today. But they’re not the same box at all.

Delete is genuinely low-value - these are things that can disappear and nothing will change. Schedule is often your highest-value work, strategically important, except it has no deadline attached yet.

Why Urgent Always Wins (Unless You Interrupt It)

Now let’s be real: urgency has its own gravity. A ping, a Slack message, an exec asking “any update?”… all of it produces a small, immediate hit of relief when you respond. I got the same hit when my VP pinged me regarding the customer escalation I mentioned earlier.

So, by default, your attention drifts, quadrant by quadrant, toward whatever is the loudest, not whatever matters most. If you leave this unmanaged and going on auto-pilot, your entire week can get consumed by Do and Delegate, with Schedule permanently postponed to “some future date that will never arrive”.

Why this matters for managers specifically: your team inherits your ratio. If you’re always in fire-drill mode, they learn that’s what gets rewarded, such as speed of response over quality of thinking.

Putting the Matrix Into Practice: The Worksheet

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

Use this worksheet to:

• Separate what needs you now from what just feels urgent

• Catch the important work you keep deferring

• Turn good intentions into a calendar block

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.

A Simple Habit: The Friday Filter

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I first read it in my twenties, and at that time, the ideas felt abstract as I was just getting started with my first job at a tech company as a software engineer.

I’ve re-read it a few times since, and I picked it up again last month, mostly out of nostalgia. This time, I expected to skim it and drop it back on the shelf.

But as I started going through the pages, I found myself dog-earing pages, because the ideas started jumping out at me. I realized that many of the ideas I now teach as “modern” leadership frameworks and strategies were captured by Convey in this classic.

So I decided to try a different format this week: I’m going to deep-dive into the key ideas from the book through the lens of modern leaders, with a focus on the frameworks and strategies that still hold up.

Here’s what I pulled out, habit by habit.

Habit #1. Be Proactive

Imagine two engineering managers, Martin and Grace, get the same bad news: the roadmap just got cut by 30%.

• Martin spends the day venting in Slack about “leadership”, about “the business,” about how nobody tells engineering anything.

• Grace spends ten minutes annoyed, then asks: “Okay, given this, what’s still in my control?” She re-scopes the quarter by the end of the day.

Both are allowed to be upset, but only one of them is being proactive.

Martin isn’t wrong to be frustrated. He’s just spending his only leverage, his response, on something that changes nothing.

👉🏻 The habit isn’t “stay positive.” It’s: control what’s yours, and stop performing outrage over what isn’t.

Habit #2. Begin with the End in Mind

Most managers I work with can tell me, in detail, what’s broken about their team right now. Almost none of them can tell me what “great” looks like six months from now.

That’s backwards.

I’ve started asking managers one blunt question: “If this team were working perfectly a year from now, what would be different?” The answer is almost always more useful than any retro they’ve ever run, because it forces them to stop diagnosing and start designing.

👉🏻 You can’t build toward an outcome you’ve never actually described.

Habit #3. Put First Things First

Here’s the trap: “important” work and “urgent” work can look deceptively similar.

• Leo runs his week from his inbox. The loudest email or Slack message wins his attention. He’s exhausted by Friday and can’t tell you what he actually accomplished by the end of the week.

• Sarah, on the other hand, blocks 90 minutes every morning before opening the Inbox or Slack. She focuses on the one or two things that matter most that week, urgent or not.

Most of your actual leverage lives in quadrant two: important, but not urgent. Nobody’s forcing you into it. You have to choose it, daily, or it never happens.

👉🏻 Your calendar isn’t a record of your priorities. It’s a record of what you decide is important, whether you do it intentionally or not.

Habit #4. Think Win-Win

Early in my career, I believed in the zero-sum game: if my team got a new project, if I pushed back on a peer’s ask, I “won.”

Covey calls this win-lose thinking, and it quietly wrecks more working relationships than any single bad decision does.

I’ve watched two people negotiate the same headcount freeze.

• Richa fought to protect her team’s number at the expense of a peer’s team, and won a bitter ally for the rest of the year.

• Malcolm proposed a split neither had asked for, one that let both teams hit their real goals. Guess who built longer-lasting trust and rapport with their team and peers?

👉🏻 Win-lose in the workplace can feel like winning in the moment, but it’s actually just borrowing against next month or quarter.

Habit #5. Seek First to Understand, Then to Be Understood

Most feedback conversations fail before a word is said, because the manager walks in already knowing what they’re going to say.

Covey’s fifth habit is uncomfortable because it asks you to do the opposite:

I try this test now in hard conversations: could I explain their side back to them well enough that they’d say “yes, that’s exactly it”? Most of the time, the answer is no, and once I actually get to that understanding, half of what I planned to say originally turns out to be unnecessary.

👉🏻 You’re not persuasive because you talk well. You’re persuasive because you understood first.

Habit #6. Synergize

“Synergy” has become a buzzword and gets thrown around so loosely in corporate life that it’s become a punchline.

I remember several years ago working with two user experience designers who used to clash constantly on a product decision. One wanted speed, while the other wanted polish.

Their manager stopped mediating between the two positions and instead asked: “What would a version look like that neither of you has proposed yet?” Within twenty minutes they’d built something better than either original pitch.

👉🏻 Synergy isn’t compromise, because compromise implies both sides lose a little. Synergy means the disagreement itself produced something neither side had.

Habit #7. Sharpen the Saw

The seventh habit is the one every burned-out manager skips first and needs most: renewal.

Many managers I work with only notice the physical dimension, and only once it’s already failing. They clock that they’re not sleeping, not the three months before that when they stopped reading anything longer than a Slack message, stopped seeing friends outside of work, and started wearing “busy” like a personality trait instead of a warning sign.

I know the mental and social dimensions personally, because I ignored both for almost two years, telling myself the team needed me too much for me to step back. What actually happened: my patience shortened, and my judgment got worse. And that’s exactly when the team needed me more, not less, because I was operating at maybe 60%.

👉🏻 You don’t get credit for the saw that never gets sharpened. You just cut slower, with more effort, and call it “dedication”.

Putting it together

Covey’s seven habits build in order:

• Habits 1–3 are about mastering yourself (Be Proactive, Begin with the End in Mind, Put First Things First).

• Habits 4–6 are about working with others (Win-Win, Understand First, Synergize).

• Habit 7 renews all six.

Effectiveness, in leadership or in general, was never about “doing more”. Covey’s whole argument, 35 years on, is still just this: know what matters, and stop pretending you don’t.

If this book-review format is one you’d want more of, tell me in the comments or hit reply. And if it was useful, a restack helps more managers find this. ❤️

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The Good Boss by Gaurav Jain

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

• The Rollout Nobody Followed

• How the ADKAR Model Works

• Why This Matters for Leaders

• Putting ADKAR Into Practice: Worksheet & Mind-map

• The One Question: Which Stage Are We Stuck On?

• How This Plays Out in Real Teams

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

The Rollout Nobody Followed

A few months ago, I watched a fellow engineering manager roll out spec-driven development (SDD) across her team. SDD is the practice of writing a detailed spec before any AI-assisted coding begins, so the LLM has a clear contract to build against instead of a vague prompt.

She did the due diligence of sharing this new approach with her team in a team meeting. She explained why the old “just prompt and iterate” habit was producing inconsistent, hard-to-review code, and SDD was the way to go. In the meeting, her team was very receptive, and they seemed to be bought in.

Three weeks later, however, half the team was still skipping specs and prompting directly.

I remember her telling me over coffee that she thought her team was just resistant to the change. She thought that engineers didn’t want the extra upfront step, and were comfortable with direct prompting. So she sent another reminder to the team on their team Slack channel, and restated the ‘why’. But still, not much changed after that.

Eventually, she got what was missing. Her team wasn’t resisting the change - in fact, they agreed the new process made sense. They just didn’t know exactly how to write a good spec: what level of detail to include, how to scope it, what “done” looked like for a spec versus for code. Nobody had ever walked them through it.

She’d explained the why, but she never covered the how.

They weren’t resisting. They were stuck.

How the ADKAR Model Works

ADKAR was developed by Jeff Hiatt, founder of the research firm Prosci, in the early 2000s, based on Prosci’s studies of how individuals actually experience organizational change. He later expanded it in his 2006 book ADKAR: A Model for Change in Business, Government and Our Community.

The model breaks any successful change down into five sequential building blocks:

• Awareness — understanding why the change is happening

• Desire — wanting to support and participate in it

• Knowledge — understanding how to change

• Ability — having the skill to actually do it

• Reinforcement — sustaining the change so it doesn’t quietly reverse

The key insight isn’t the five words themselves, it’s the order.

You can’t build Desire without Awareness. You can’t build Ability without Knowledge. A team can be fully aware of a change, genuinely want it, and still fail simply because nobody built their skill to execute it.

Most change efforts don’t fail because people are against the change. They fail because leaders manage the first step and assume the rest will follow on its own.

Why This Matters for Leaders

Most managers are fluent in exactly one step of ADKAR: Awareness. We’re comfortable with the announcement: the all-hands, the Slack post, the deck explaining the “why.” What we’re far less comfortable with is everything after it.

The “I told them why, so they should want to” gap. Awareness and Desire are not the same thing. A team can fully understand why a change is happening and still not want to be the one to make it happen, especially if the change adds short-term friction to their workload with no visible upside for them personally.

The skills-vs-tools confusion. Knowledge and Ability get treated as interchangeable, but they’re not. Knowledge is understanding the new process in theory. Ability is doing it under real conditions: mid-sprint, under deadline pressure, with muscle memory that hasn’t formed yet. A single training session builds Knowledge, but it rarely builds Ability.

The “it seems to have stuck” trap. Reinforcement gets skipped entirely because, by the time you’d revisit it, the change looks like it’s working. Old habits don’t disappear the moment a new process launches. They fade slowly, and they come back the moment nobody’s watching.

Putting ADKAR Into Practice

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

Use this worksheet to:

• Pinpoint exactly which stage a stalled change is stuck on, instead of guessing at “resistance”

• Plan the right next action for that specific stage

• Prepare a rollout so every stage gets deliberate attention, not just the parts that come naturally

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 One Question: Which Stage Are We Stuck On?

When a change effort stalls, most leaders ask “why aren’t they doing this?” That question is too broad to act on. It invites vague answers like “resistance” or “culture,” and neither one tells you what to actually do next.

Read more

There’s a “scoreboard” in every organization. Not the Jira dashboards or the AI Tokens dashboards that you might be thinking.

This scoreboard doesn’t show up in your performance review. It’s not in any “handbook” or part of any HR onboarding.

But it shapes who gets promoted, who gets bypassed, and who wonders why nothing seems to move in their favor despite doing excellent work.

For years, I kept my head down and trusted that results would speak for themselves. But to my dismay, they didn’t, and it was frustrating for me.

To be clear, this article isn’t about “playing dirty”. It’s about learning to read the scoreboard, and playing smarter.

Here are 9 rules that changed how I navigate office politics.

1. Understand That the Scoreboard Is Real

Imagine two managers, both high performers on paper.

Priya delivers results quarter after quarter, but rarely speaks in cross-functional meetings. She does the work, writes the recap, and moves on. Rajan, same level, same output, but he consistently frames his team’s wins in terms the VP cares about. He shows up to the optional strategy session. He even sends a short “here’s what we learned” note after every milestone.

At year-end, Rajan gets the stretch assignment, while Priya gets feedback that she “needs to raise her visibility.”

The first step is accepting that the scoreboard exists, and that ignoring it doesn’t make you any better than or above others.

It just means you’re losing without knowing the score.

2. Know Who Actually Holds the Power

Every org has two structures: the one on the official org chart, and the one that actually runs things.

The org chart tells you who has the title, and who reports to whom. The real structure tells you whose opinion moves decisions, whose pushback kills proposals, and whose endorsement opens doors.

I’ve seen junior people with enormous “informal” influence, the one everyone trusts to read the room, the one the CEO always calls before a tough call. And I’ve seen senior leaders who have the title and none of the pull or weight you’d expect from them.

Mapping informal power is one of the most underrated skills in leadership. You need to look for:

• Who gets listened to when they speak, even without formal authority?

• Whose silence in a meeting signals something?

• Who do people go to for advice before a big meeting?

My suggestion: Draw this out on a piece of paper. Yes, I’m serious, and you also need to keep it updated as people move around. This is your real power chart.

3. Protect Your Reputation Like a Balance Sheet

In the corporate world, I believe that your reputation is a balance sheet. Every interaction adds or withdraws:

• You deliver on time: deposit.

• You overpromise and miss: withdrawal.

• You give someone else credit publicly: deposit.

• You take credit for shared work: withdrawal, and a big one.

One bad moment of taking credit, of talking behind someone’s back, of being unreliable when it mattered, and it takes a long time to undo.

The leaders who navigate politics well are almost always the ones people describe as “reliable” and “straight.”

You can’t build influence on a foundation people don’t trust.

4. Build Relationships Before You Need Them

Most people reach out to their relationships when they need something. It could be a favor, a decision, or a referral.

But that’s not relationship-building - that’s transacting.

Consider two directors going into a reorg.

Marcus spent years developing relationships across the org because he was genuinely curious about what other teams were working on. He grabbed coffee, shared articles, asked questions that weren’t about him. And guess what: when the reorg hit, three different leaders advocated for his team to stay intact.

Natasha went into the reorg with strong results and no internal network. Predictably, her team got scattered.

I’m always reminded of the age-old saying: The time to build the roof is when the sun is shining.

Build the relationships during the quiet stretches, when there’s nothing at stake. That’s when they become real.

5. Manage Up Without Becoming a Sycophant

There’s a fine line between managing up effectively and becoming the manager who just tells the boss what they want to hear, i.e., a sycophant.

The sycophant agrees with everything and optimizes for approval. This may work in the short term, but I’ve seen such managers eventually lose credibility with peers and eventually with the leader too, because leaders with good judgment eventually notice.

I know it isn’t easy, but here’s the formula that I’ve found to work well:

• Share frequent, short updates.

• Frame your work in terms of what they care about.

• Raise problems early, with options (don’t be seen as a complainer)

And when you disagree, say so directly, once, clearly, and then commit to whatever direction is chosen.

6. Choose Your Battles Like a Chess Player

Not every hill is worth dying on.

I’ve watched talented leaders spend enormous political capital fighting battles that didn’t need to be fought: a process they disagreed with, an organizational decision they couldn’t change, a colleague’s behavior that, in the grand scheme, didn’t matter.

I’ve been in that situation too, and I know it’s not easy in the moment.

But here’s the reality: every fight costs something, even when you win. You should spend that capital on the things that genuinely require your voice.

Here’s the 3-Question Test I use before entering any political battle:

1. Does this align with what I actually care about?

2. Do I have a realistic chance of changing the outcome?

3. Is the cost of winning worth it?

If the answer to any of these is no, you should just step back. Save your energy for the fight that actually matters.

7. Credit Is Currency — Spend It Generously

One of the fastest ways to build political capital is to give it away.

I know that sounds counterintuitive, so hear me out…

When you publicly recognize someone else’s contribution, like in a meeting, in an email to leadership, in a Slack message, you signal something important: you’re not threatened by other people’s wins.

And that signal is heard by everyone in their subconscious.

Imagine two senior managers presenting the same team project to leadership.

• Anika says: “We pulled this off because of Leo’s insistence on simplifying the approach early. That call saved us three weeks.”

• David presents the same project: “I identified a key risk early and restructured the delivery plan.”

Leo remembers Anika forever, and the VP or senior leader notices who is building their team, and who is trying to collect credit.

Credit generosity is one of the highest-return political moves you can make, and it costs you nothing.

8. Read the Room Before the Meeting

The biggest political mistakes don’t happen in the meeting, they happen before.

Senior leaders call this “socializing an idea.” It sounds political, and frankly, it is.

Before any significant decision, proposal, or change request, talk to the key stakeholders individually first.

You’re doing this to listen, and to understand what they care about, where they might push back, and what framing will land. By the time you’re in the room, the room should already mostly agree.

They were pre-wired before the meeting started.

Pre-wiring sounds like extra work, and may feel manipulative. But it’s actually the thing that removes rework, misalignment, and the slow death of a good idea by a thousand objections.

If you walk into a meeting to get alignment, you’re already behind. Walk in to confirm it.

9. Stay Clean When Things Get Dirty

Office politics turns toxic when people start using it as a weapon: gossiping, undermining, taking sides in conflicts that don’t involve them, etc.

This is where I’ve seen smart leaders make career-ending mistakes. They think they’re playing the game well, but end up paying for it in the longer run.

When someone gossips to you about a colleague, don’t engage. When there’s an opportunity to take a shortcut that involves stepping on someone else, don’t do it.

The people who navigate politics well over the long run are the ones everyone trusts to play it straight.

Office politics isn’t dirty in and of itself. It’s up to you to play it well, with integrity.

Final Thoughts

The invisible scoreboard keeps running whether you pay attention to it or not.

The leaders who advance aren’t usually the ones who played the dirtiest. They’re the ones who understood how influence actually moves through relationships built in advance, through credit given generously, through reputation protected carefully, and through battles chosen wisely.

You don’t have to love politics to get good at it. You just have to stop pretending the scoreboard doesn’t exist.

In short: Learn the rules, play the long game, and stay clean.

💬 What’s the most important office politics lesson you’ve learned? Drop it in the comments.

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The Good Boss by Gaurav Jain

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

• The Deck That Almost Fooled Everyone

• The AI Confidence Trap Explained

• How AI Is Pulling Confidence and Competence Apart (The Three Shifts)

• Why This Matters for Leaders

• The One Shift: Assess the Thinking, Not the Output

• How This Plays Out in Real Teams

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

The Deck That Almost Fooled Everyone

A few days ago, our VP dropped a message in Slack asking for numbers to substantiate a new initiative we were considering.

Within an hour, our PM had responded with a polished deck. The deck had lots of data, just like what was asked: clean charts, lots of data points, and a compelling narrative.

I’ll be honest: my first reaction was impressed. The argument it made was convincing, but something inside me couldn’t settle just yet.

A few of the numbers didn’t quite match my intuition about what the data should look like. So I asked the PM a simple question: had he verified these numbers with the data engineering team?

Apparently, he hadn’t.

I took the figures to my data engineers, and what they found was an eye-opener. Data was being used to support interpretations it didn’t actually support. Numbers were cited without the context that would have completely changed their meaning. A few of the figures were just wrong.

What struck me most wasn’t that the PM had cut corners: he was responding quickly to a senior ask, which is exactly what you’d want someone to do. What struck me was how convincing the output was. If I hadn’t pushed, that deck might have sailed straight into a VP conversation and shaped a real decision. Nobody in the room would have known the foundation was shaky.

This is the risk that keeps me up a little more than it used to.

AI can produce a polished, confident, well-structured argument for almost anything, including things that aren’t true. And in a world where that capability is available to everyone on your team, the leaders who don’t learn to look past the polish are going to get burned.

This is what I’ve come to call the AI Confidence Trap.

The AI Confidence Trap Explained

The AI Confidence Trap is what happens when AI-generated polish creates the appearance of competence that isn’t fully there, and leaders and even individuals themselves mistake that appearance for the real thing.

To be clear, in most cases, the person using AI isn’t trying to deceive anyone. They’re doing what any sensible professional does: using the best available tools to produce the best possible output.

For most of professional history, the quality of someone’s written output was a reasonable proxy for the quality of their thinking.

• A well-written document usually meant a well-thought mind had produced it.

• A clear, confident recommendation usually meant someone had done the work to arrive at it.

• A detailed thesis usually meant the student or researcher had spent months on extensive research.

• A striking piece of visual art usually meant someone had spent years developing a craft.

Today, AI has broken that relationship.

• Now, a well-reasoned document might mean a well-reasoned mind… or it might mean a capable prompter and a powerful language model.

• A confident, comprehensive analysis might reflect deep expertise… or it might reflect a good template and fifteen minutes.

• A striking piece of visual art might mean years of developed craft… or it might mean a well-written prompt and a image generation tool.

The problem is: from the outside, these can look identical.

And this creates a new leadership challenge, which is the heart of the AI Confidence Trap:

How do you assess judgment, develop capability, and make good decisions about people when the primary signal you’ve historically relied on (output quality) is no longer reliably telling you what you think it is?

How AI Is Pulling Confidence and Competence Apart (The Three Shifts)

The AI Confidence Trap shows up differently depending on where you look. Here are the three places it’s most likely to be affecting your team right now.

Read more

• The Confusion at the Heart of the Anxiety

• Why Scarcity Makes You More Valuable, Not Less

• What Becomes More Important, Not Less

• The Leaders Who Should Actually Be Worried

• What This Means for You

There’s a story going around, and you’ve probably heard it, and even told yourself a version of it.

Let’s face it: AI is getting smarter every day. AI tools are now writing the reports, summarizing the meetings, and even making recommendations to help you make decisions.

Slowly, the things that used to make a leader valuable are getting automated.

I want to push back on this, because I think the story is exactly backward.

The best leaders aren’t going to matter less in the AI era. They’re going to matter more than they ever have.

And the leaders who are anxious about this moment are usually the ones who were never really leading in the first place: they were managing, and calling it leadership.

Let me explain why.

The Confusion at the Heart of the Anxiety

Most of the fear about AI and leadership comes from a single confusion: mistaking management for leadership.

Let’s me clear that up:

• Management is the visible work. Think status updates, resource allocation, performance tracking, reporting, etc. It’s necessary and valuable, and, let’s be honest, a huge amount of it can now be done faster and better with the help of AI tools.

• Leadership is completely different. It’s the less visible work, such as building trust, making a hard call when the data is incomplete, and sitting with a team member in their worst week and making them feel like they still matter.

This is good news, not bad news, but only if you’ve actually been leading, not just managing.

Why Scarcity Makes You More Valuable, Not Less

Here’s a simple economic truth: value follows scarcity.

For the last few decades, “good management” has been relatively abundant. Most competent professionals, with enough training, could learn to run a status meeting, build a project plan, or analyze a dataset.

They still matter, but they’re more abundant and cheap.

Meanwhile, the deeply human skills: emotional intelligence, judgment under uncertainty, the ability to build trust, the courage to have a hard conversation, were always rare. They were just masked by how much time and attention management work was consuming.

Strip away the management noise, and what’s left is the real leadership signal. And in a world flooded with AI-generated output, the leader who can offer genuine human judgment, presence, and trust becomes not just valuable, but essential.

What Becomes More Important, Not Less

So what skills are more important now with AI taking over more of the management layer?

• Judgment. AI can give you ten well-reasoned options, but it can’t tell you which one is right for your specific team, your specific culture, and your specific moment in time. That call of weighing the human factors, the context, becomes more valuable precisely because there’s more information and less clarity.

• Trust. As more of the processes become automated and abstracted behind AI-powered dashboards, the leaders who can build genuine human trust become more valuable to the organization. Trust is now becoming one of the scarcest currencies in the workplace.

• Genuine connection. The more interactions get automated and run by AI-powered bots, the more people crave the real conversations. Imagine trying to solve a high-stakes issue over coffee with a colleague vs staring at the screen while chatting with a small chat window.

Check out my other post where I discuss these skills in a more detail:

The Leaders Who Should Actually Be Worried

All that being said, I won’t pretend everyone is safe. Some leaders should genuinely be worried.

These are leaders whose entire value proposition was built on the management layer.

• The ones who were really good at running the process, but never built real relationships.

• The ones who could produce the report, but never built the trust.

• The ones who confused being busy with being valuable.

I know that’s an uncomfortable truth, but I also think it’s an opportunity.

If you’ve been investing in the deeply human side of leadership all along, even when it felt less “productive”… congratulations! You’re about to be in the most valuable position you’ve ever been in.

What This Means for You

If you’re feeling anxious about AI and your role as a leader, here’s the reframe.

• Don’t ask: “What can AI now do that I used to do?”

• Ask instead: “Now that AI can handle the management layer, what does that free me up to actually focus on?”

Leadership was always the real job. Now, AI is just making it impossible to hide behind anything else.

💬 Do you find this reframe energizing or anxiety-inducing? Let me know in the comments.

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The Good Boss by Gaurav Jain

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

• The Manager Who Changed Everything (By Doing Nothing New)

• What the Hawthorne Effect Really Is

• How Observation Changes Behavior (The Three Layers)

• Why This Matters for Leaders

• The One Shift: From Watching to Trusting

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

The Manager Who Changed Everything (By Doing Nothing New)

A while back, I inherited a team that had a reputation for being disengaged.

The deliverables were late, and there were issues with the quality of the features being released. The previous manager had tried adding more structure, like more check-ins, more reporting, more visibility into who was doing what. But apparently, none of that helped.

I didn’t overhaul the process, but simply started being there, whether in meetings, working sessions, etc. My intent wasn’t to inspect or interrogate, but to ask questions, and just be present in the day-to-day.

Within a few weeks, I observed a change: the work quality picked up, and so did the energy in the team meetings. And I found myself wondering: was this me, or was something else going on?

The honest answer was: it wasn’t really me.

This is called the Hawthorne Effect.

What the Hawthorne Effect Really Is

The Hawthorne Effect traces back to a series of experiments conducted in the 1920s and 1930s at the Hawthorne Works, a Western Electric factory near Chicago.

Researchers set out to study whether changes in physical working conditions, such as lighting levels, break schedules, working hours, etc. affected worker productivity.

What they found surprised them.

Productivity improved almost regardless of what change they made. Whether you changed the lighting to brighter or dimmer, or changed the breaks to longer or shorter, the output still went up. The results were consistently positive, no matter the direction of the change.

The Hawthorne Effect, in its simplest form, is this: people change their behavior when they know they are being watched.

I do want to note that subsequent researchers have debated the original findings and their interpretation, and the data from those studies was messier than the clean narrative suggests.

But the core behavioral insight has helped up over the decades of organizational research and real-world leadership experience: attention shapes behavior. And once you understand that, you start seeing it everywhere.

How Observation Changes Behavior (The Three Layers)

The Hawthorne Effect isn’t a single thing. It shows up in three distinct ways in a leadership context, and each one has different implications.

Read more

• The Cover That’s About to Disappear

• Why This Has Been Hiding in Plain Sight

• The Crisis Isn’t AI. It’s What AI Reveals.

• How to Make Sure You’re on the Right Side of This

• My Honest Take: The Bottom Line

For years, there’s been a silent problem in leadership that nobody wants to talk about:

Remember the “leaders” who would run long meetings, track metrics, and respond to emails and Slack at impressive speeds? These leaders look busy, and sound competent.

But I’m sure you’ll agree with me that many of these managers were actually really poor leaders. So, what was really happening, you might ask?

AI is about to change that, or should I say, is already changing that.

The Cover That’s About to Disappear

Here’s what I mean by “cover.”

For decades, the “busywork” of management has provided a kind of camouflage. If you were constantly in meetings, constantly writing decks, constantly responding to emails and Slack, you looked like a leader.

Nobody had the tools, or frankly, the desire, to decouple “doing a lot of management tasks” from “actually leading people well.” The two got bundled together, and most organizations never bothered to unbundle them.

That bundle is falling apart. With AI tools, you can easily draft the report, summarize the meeting, build the project plan, and analyze the data.

What’s more: it’s often faster and more thorough than a manager who used to spend hours on it. I’ve come to rely on and trust these tools with every passing day, as I’m sure you have, too.

Why This Has Been Hiding in Plain Sight

Mind you, this isn’t a new problem. In fact, it’s an old problem that’s now impossible to ignore.

In your own experience, have you noticed…

• The manager who’s everywhere, yet adds little to no value to the organization.

• The leader who’s always “slammed” but whose team feels lost and directionless.

• The person who’s exceptional at producing the appearance of progress, but whose team’s actual trust, growth, and morale have been eroding the entire time.

As I said, this isn’t new.

We’ve all noticed the managers who are busy but not leading, who’re visible but not making an impact. We’ve just never had a clean way to prove it.

Today, AI is breaking that illusion because it’s about to produce the same outputs with minimal or no leadership behind it at all.

The Crisis Isn’t AI. It’s What AI Reveals.

To be clear, the “crisis” I’m talking about isn’t that AI is going to take away leadership roles.

I’m sure this is going to get uncomfortable in many, if not most, organizations.

Some leaders will discover, in a fairly public way, that they don’t have much left once their task list is automated and managed by AI tools. Some teams are going to realize that the person who looked like their ‘leader’ for years was mostly just... busy.

And some leaders, the ones who were doing the real work all along, the trust-building, the coaching, the hard conversations, the steady presence in difficult moments, are finally going to get seen for what they were actually contributing. Maybe even for the first time.

This is the real crisis:

Maybe it’s not even a crisis. It’s a relief.

How to Make Sure You’re on the Right Side of This

If this is making you uneasy, here are a few places to start:

• Audit your week. How much of what you did this week was task execution versus genuine leadership (e.g., coaching, hard conversations, trust-building, judgment calls)?

• Find the conversation you’ve been avoiding. If there’s a hard conversation sitting on your to-do list, that’s a clear signal of where you need to pay attention.

• Stop hiding behind “busy”. If your calendar is full but your team’s trust, growth, and morale are low or stagnant, you need to clean up your calendar and schedule your real priorities as a leader.

I don’t mean to scare you, but here’s me taking the action of sharing what needs to be shared with you:

My Honest Take: The Bottom Line

For years, “busyness” was a reasonable proxy for leadership impact, because we had no better way to measure it.

With AI, that proxy is disappearing, and what’s left is the only thing that ever actually mattered: whether you made the people around you better.

Some leaders have nothing to worry about, as they’ve been doing the real work all along, often without much recognition for it. Others, on the other hand, have a choice to make, and honestly, not much time left to make it.

💬 Be honest: which one are you? What are you doing differently as a leader with AI? Let me know in the comments below.

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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

The Good Boss by Gaurav Jain

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

• The Problem With “Smart” Leaders

• What Occam’s Razor Really Means

• How Complexity Creeps In (The Razor in Action)

• Why This Matters for Leaders

• The Razor Audit: Cut Before You Add

• How This Plays Out in Real Teams

• Common Pitfalls (and How to Avoid Them)

• Final Thoughts

The Problem With “Smart” Leaders

A few years into my leadership career, I noticed something uncomfortable about myself.

Every time a problem came up, my instinct was to add something.

• A new process to fix the coordination issue.

• A new framework to improve how we made decisions.

• A new meeting to make sure everyone was aligned.

• A new wiki or document to capture everything we’d agreed on.

And I remember clearly - I could justify every one of them at the time.

Simple things had become unnecessarily complicated. I realized that my team, the very people this was supposed to ‘help’, was now spending more time managing the process than actually doing the work.

I thought I was solving problems, but in reality, I was actually creating them.

They think that if something is too simple, it’s probably not right. There’s a centuries-old principle that cuts right through this.

It’s called Occam’s Razor.

What Occam’s Razor Really Means

Occam’s Razor is a principle attributed to the 14th-century philosopher and friar William of Ockham.

The original idea, roughly translated, is this:

In plain terms: when in doubt, go with the simpler explanation.

Simple is not always correct, but complexity has a cost: it has more assumptions, more moving parts, more things that can go wrong. The simpler explanation is usually easier to test, communicate, and act on.

And more often than not, it turns out to be right.

Scientists and philosophers have used Occam’s Razor for centuries as a guide for building theories and solving problems. But I’ve come to realize that the principle translates really well to leadership, because leaders face a version of this challenge every single day.

• Every time something goes wrong on your team, you have a choice: find the simplest explanation and address it directly, or reach for something more elaborate or complex.

• Every time you design a process, you have a choice: keep it lean and simple, or keep adding until it feels comprehensive.

• Every time you communicate a decision, you have a choice: say it plainly in simple words, or fill it with context and business jargon to add more ‘weight’ to it.

How Complexity Creeps In (The Razor in Action)

Here’s the thing about complexity: it rarely arrives all at once. It accumulates slowly, one reasonable-looking decision at a time.

Read more

Let’s be honest about what’s happening.

AI is already writing your meeting summaries, drafting your performance reviews, and generating your project plans.

And let’s face it: it’s doing most of that pretty well.

And here’s what I have noticed: most leaders respond to this moment in one of two ways. They either panic, or they are curious and go deeper into the very things AI can never touch.

Why These Skills Get Neglected

Before we get to the five skills, let’s address the elephant in the room.

These aren’t “new” skills. They’ve been around for ages.

So why do most leaders neglect them?

Here’s my take: that’s because they don’t produce immediate, visible output.

• You can’t put “built trust with my team this week” in a status update.

• You can’t quantify the coaching conversation that changed someone’s trajectory.

• You can’t screenshot the moment a team felt genuinely safe to speak up.

And in a world that rewards visible productivity, the less visible work of real leadership gets pushed to the back of the queue.

Let’s talk about what that looks like.

1. Presence

I once had a manager who would check his phone every few minutes during our one-on-ones.

He was a great task master: he never missed a deadline, never dropped a deliverable. He never even skipped a meeting.

And yet, no one on the team felt seen by him.

Today, AI can schedule your one-on-ones, prep your talking points, and summarize the conversation afterward.

But it can’t be there.

• It can’t notice the pause before someone answers.

• It can’t sense the energy shift when someone is struggling.

• It can’t sit with discomfort without rushing to fill it.

Great leaders are fully present.

Most leaders I talk to either overlook or completely neglect this because presence is slow and time-consuming. You can’t scale or automate it. You can’t run it as a batch process.

💡The practice: In your next one-on-one, put your phone in your bag, close your laptop, and give the person your full, undivided attention. Just do that, and see what happens.

2. Courage

Here is something most leaders learn the hard way: the conversation you keep avoiding is usually the one that needs to happen most.

Today, AI can draft your feedback. It can suggest the right words, the right tone, the right structure. It can give you the full script, ready to go. But it can’t step into the emotional weight of a conversation with someone whose career, confidence, or sense of self might be impacted by what you say.

That requires courage, and courage can’t be automated.

I’ve seen leaders who were excellent at managing around difficult conversations: restructuring teams instead of addressing individuals, rewriting job descriptions instead of having performance discussions, going quiet instead of saying the hard thing.

In the short term, it looked like kindness. In the long term, it was the opposite.

💡 The practice: Identify one conversation you’ve been avoiding, and schedule it this week. You’ll feel uncomfortable, but that’s a sign that that conversation is important and needs to happen.

3. Sensing

When you look back at things, the data tells you what happened, but it almost never tells you why.

I once had a team that, on paper, looked like a high-performing team. We were delivering on track, and our engagement scores were also quite decent. We didn’t face many major customer incidents either.

But when I went into team meetings, I could sense the interactions that were polite but guarded.

I decided to identify what was going on, so I started having more informal conversations. What I found was the team was living in a culture of ‘quiet fear’ - they had learned that raising issues or problems was riskier than just hiding them.

This is one of the most underrated leadership skills: the ability to sense:

• To notice what people aren’t saying.

• To detect the early signals of disengagement or fear

• To mine for conflicts before they become crises.

💡 The practice: After your next team meeting, ask yourself: “What wasn’t said in that room? What was the energy telling me that the words didn’t?” Make that a regular habit.

4. Growing Other Leaders

Have you noticed this pattern: A high-performing leader gets promoted, but their team stays the same. The organization gets one better leader but loses the development engine that was making everyone around that leader better.

Real leadership development isn’t a program or a process. It’s a practice.

• It’s asking the right questions in the right moment.

• It’s holding someone to their potential even when they’ve forgotten what it is.

• It’s knowing when to challenge and when to support.

Today, AI can generate coaching questions, recommend development resources, and even simulate a feedback conversation.

And here’s why most leaders neglect it: developing others is slow, ambiguous, and the results are often invisible until much later. It’s far easier to just do things yourself.

💡 The practice: Pick one person on your team whose potential isn’t yet being fully realized. Make their growth a deliberate focus for the next 90 days.

5. Emotional Regulation

The world today is more complex and chaotic than ever. Markets are shifting, strategies are pivoting, reorgs and layoffs are happening.

Calm is contagious, and so is fear.

Today, AI can give you scenarios to consider. It can model probabilities at the detail level, and it can draft your communication plan for difficult announcements.

But it can’t provide the steady presence with signals your team is looking for in times of uncertainty. It can’t absorb the anxiety in a room and return it as confidence and calm.

The only challenge: it doesn’t have a ‘metric’, and it doesn’t show up in performance reviews. But it is also one of the few things your team notices, every single time.

💡 The practice: The next time you’re in a high-pressure situation, pause before you react. Take a deep breath and ask yourself: “What does my team need from me right now — information, or steadiness?” Likely, it’s the latter.

The Honest Summary

These five skills share a few things in common.

• They are slow.

• They are difficult to measure.

• They produce no immediate “output”.

And they are exactly what will make you irreplaceable in an era when everything measurable and outputtable is increasingly being handled by AI.

💬 Which of these five skills do you most need to develop? Let me know in the comments.

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The Good Boss by Gaurav Jain

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