If you’ve been following me here for a while, you know that I’ve been writing framework deep dives on The Good Boss every Monday for the past 2+ years.
Consider this: on your typical Monday morning, you read the framework post, maybe even download the worksheet. The framework stays fresh in your mind for the next few hours.
Fast forward to Tuesday afternoon - your week is in full swing, and you have a dozen emails, back-to-back meetings, and three escalations waiting for your attention.
On Wednesday at 4.30 pm you meet Lisa, your top-performing team member, for a regular 1:1 meeting. Lisa tells you that she’s thinking about leaving the company. Your heart rate goes up, and every framework you’ve ever read goes out the door.
Does that sound like you?
Well, it definitely sounds a lot like me. I’ve written about Conway’s Law, the Ladder of Inference, the Abilene Paradox, and dozens of others here for years. I still have moments where I walk out of a meeting and think, “I knew exactly what to do there. I just didn’t do it.”
That gap between knowing and doing is the real problem that most leaders face. Reading fills your head, but it doesn’t build the reflex.
So for the last several months, I’ve been building something to close that gap. And today, I’m excited to reveal it to you! 🧡
It’s called Kyoshi.
What Kyoshi is
Kyoshi is a systems-first leadership coach.
It’s built on the Leadership OS, it knows what you’re dealing with this week, and it helps you to work out a solution like a real coach would.
The word “Kyoshi” comes from Japanese for a ‘master teacher’, someone who has put in the reps and now helps others put in theirs. That’s the energy I wanted with Kyoshi - more “coach”, less “guru”.
And in case you’re curious about the logo - I designed that, too, with intention.
The logo is an open ring with the opening facing up, and it stays open for a reason. I hope you’ll agree with me that leadership is never “finished”, and the best leaders I know stay optimistic and keep going.
That’s what the logo is supposed to symbolize.
Kyoshi Waitlist is Open! 🔥
Kyoshi will be launching soon, and the waitlist is now open at kyoshi.ai/waitlist. Join now and be the first to get access at launch week!
What Kyoshi isn’t
Okay, now let’s address the elephant in the room…
At this point you’re probably screaming: Isn’t Kyoshi yet another AI chatbot?
After all, you can already ask a general AI tool like ChatGPT or Claude for leadership advice. So, what’s different?
Here’s the thing:
We’ve all tried asking those generic AI clients for leadership advice. Granted, they spit out a nice and tidy list of ten tips that would fit any manager at any company. The advice also makes us feel good about yourself, and who doesn’t like that?
But here’s the problem: those tools are great at giving you general advice, but really poor at providing anything actionable.
It’s like asking a stranger at a bus stop for marriage advice. You’ll likely get a polite, confident reply, when they have no idea who you are, or how you can act on it.
Kyoshi is built on the foundation of the Leadership OS, the system I’ve been designed and have been writing about here for years.
The Leadership OS has four layers: Leading Self, Leading Others, Leading Results, and Strategic Leadership. Each layer has skills, and skills have associated frameworks.
Here’s my fundamental premise:
Great leadership isn’t something you’re born with. It’s something you can learn, master, and apply, and the entire system of the Leadership OS and now, Kyoshi, is built on that principle.
And one more thing makes Kyoshi different - it helps you to manage and solve what I call situations.
A situation is the symptom you’re seeing this week in your leadership role, e.g. “my team agrees in meetings and then does nothing.” As you can imagine, the same symptom can come from very different root causes. Maybe it’s the Abilene Paradox. Maybe it’s unclear ownership. Or, maybe your team just doesn’t trust you yet.
Kyoshi helps you figure out which one it is before it hands you a framework or a path forward.
Most advice starts with the answer. Good coaching starts with the diagnosis.
The Three Rooms
Kyoshi is organized around three “rooms” or stages if you will, depending on what you’re looking for right now:
📚 Learn - the Library - where you go to learn and master the fundamentals of leadership
💪 Practice - the Gym - where you go to build your leadership muscle by trying a skill or framework in a safe environment
🔧 Apply - the Field - where you put your learning to solve a real situation you’re facing right now
The library makes you informed. The gym makes you ready. The field is where it actually counts.
Next, let’s look at the three rooms in a bit more detail.
📚 Learn - The Library
The library is where the skills and frameworks come alive, organized by the Leadership OS so you can see how they connect.
Here’s a quick preview of the library (or the Learn section):
You can explore the library in a number of ways:
⚙️ The System: You can learn about the Leadership OS, how the four layers are interrelated, and how the system works under the hood. This forms your foundational understanding of leadership.
🧠 The Skills: You can explore the set of essential skills you need to develop as a leader, and how they are linked to the Leadership OS and the layers. You can even ask Kyoshi questions related to a skill, or how to develop that skill.
🛠️ The Frameworks: If you’re looking to understand a specific framework, say the Situational Leadership or Radical Candor, you can read how it works, and how it relates to the skills and layers as part of the Leadership OS. You can also browse through the list of all frameworks.
📍 The Mind-map: This is for the visual explorers like me :) You can walk into the library and explore the entire system at a glance with the interactive mind map, just like you would when walking into a great bookstore! (I did that recently at the Powell’s bookstore in Portland - what a treat!)
🧪 Quizzes: You can also test your understanding of the frameworks with quizzes - this ensures that you’re not just consuming, but also actually learning and retaining.
💪 Practice - The Gym
You don’t get better at hard conversations by “reading” about them. You get better by having them.
In the gym, you rehearse the conversation before you face it for real: it could be the performance review, the pushback from your executive leader, or the engineer on your team who wants a promotion that you can’t yet give.
And because this is not a real situation, you get to try it without the fear of failure, and get to build your muscle and confidence.
Here’s a quick preview of the gym (or Practice section):
In Kyoshi, you have access to:
🎭 Role Plays: Kyoshi can play the role of your boss, your team member, your customer, or any stakeholder. And the real value is after the conversation, when Kyoshi will debrief and provide you with feedback to help you improve and get better.
🎬 Scenarios: You are presented with a realistic scenario (from a list of several options), and get to be the decision owner. As you go through the scenario, you get to experience the outcomes of your decisions. Like in most things leadership, there are no right answers, just tradeoffs. At the end of the simulation, Kyoshi provides you with feedback so you can get better at handling them when you face them for real.
🎯 Drills: You get to practice a framework of your choice (among 100+ in the library) in a realistic situation to experience what it feels like in action. This helps you to build your muscle memory and really practice the application of the framework, beyond just reading about it.
🔖 Worksheets: You can generate worksheets for a framework of your choice any time, on-demand, for online or offline use. Download the PDF and print it out to take to a real situation if you like, or just run through the worksheet in a test scenario if that’s what you want.
🔧 Apply - The Field
The field is where the rubber hits the road, so to speak.
Kyoshi isn’t just for learning and practicing. The real payoff is in the actual application of that learning to real, live situations you’re facing in your leadership role this week.
The field is where Kyoshi helps you turn your knowledge and skills into actual application to real, live situations you are facing in your leadership role. Kyoshi coaches you through it, asks the questions a good coach would ask, and helps you leave with a decision instead of a vague plan.
You can create new situations directly, or Kyoshi can also prompt you to create a situation mid-conversation to help you track it.
Here’s a quick preview of the field (or Apply section):
Here are some of the things you can do in the field:
✅ Track commitments: As Kyoshi learns about the situation through conversation with you, it can infer the underlying commitments. This could include a scheduled meeting with your boss next Tuesday at 3 pm, or a call you need to make to a customer this Friday at 10 am. Kyoshi will proactively monitor these commitments as they emerge through your conversations, and help you stay on track.
📎 Generate Artifacts: Kyoshi can help you generate various artifacts, depending on the situation and context. These could include talking points, discussion summaries, downloadable PDFs, etc. You can also attach your own documents to a situation to provide Kyoshi more context beyond just the conversation, and Kyoshi will keep all of those organized and accessible for you.
🙌🏼 Prepare: Kyoshi helps you prepare for that big meeting or that high-stakes moment. Let’s say you have an important meeting coming up with your VP next week. You can create a new situation in Kyoshi, and it will help you prepare for it, including the talking points, the slides or artifacts, etc. You can even run a role-play or a scenario to practice before the meeting to get a “feel” for it.
What Kyoshi won’t do
I know many of you reading this are engineering managers, and you’ve seen enough AI hype (for good or for bad depending on how you see it!)
So, let me be clear about what Kyoshi won’t do…
Kyoshi won’t make decisions for you. It helps you think, consider, but you still own the decision.
Kyoshi won’t replace your manager, your mentor, or a human coach. It’s there for the 80% of moments when none of them are available, which, if your week looks like mine, is most of them.
Kyoshi won’t flatter you (yeah - we’ve had enough of that fake humility with ChatGPT and Claude). If the root cause of your problem looks like you, it will say so, but kindly.
🔥 The waitlist is now open!
A small group of you has been using Kyoshi in a private beta for the last couple of weeks. The feedback has been great, and is already helping to shape the product.
Some initial feedback I’ve received from the beta users:
“I love the Practice section, especially the role plays and scenarios where you have to think through a situation and respond.”
— Kyoshi beta user
“I used it on one real scenario. It was a useful discussion partner and gave me one point to think about that I hadn’t considered. Good enough that I’ll try it on something else.”
— Kyoshi beta user
“I tried it to help move forward on a potential sale. Impressed so far.”
— Kyoshi beta user
Now it’s your turn. The waitlist is open now at kyoshi.ai/waitlist.
So go ahead and sign up for the waitlist. Kyoshi will be launching soon, and early members will be offered a founding-member plan during launch week that you don’t want to miss out on!
One last thing
I started The Good Boss because I had bad bosses and good bosses, and the difference came down to what they did on an ordinary weekday when things got hard.
This newsletter gives you the ideas, and Kyoshi is where you practice them and make them real.
I hope you’re as excited about Kyoshi as I am, and I look forward to seeing you work with Kyoshi by your side, and skyrocket your impact as a leader!
Don’t forget to join the waitlist to be the first to get access to Kyoshi!
👉🏻 Join the Kyoshi waitlist → kyoshi.ai/waitlist
❤️ Help spread the word!
If the idea behind Kyoshi resonated with you, please like and share this post with other managers who can benefit from it, including your boss :) If you have any feedback, please drop your comment below. Thank you!
