A friend recently asked me to review a management training program he’s developing. The core idea is a management dojo. New managers would practice difficult conversations, delegation, accountability discussions, and other leadership situations before they must perform them in an actual business situation.
My first reaction was positive. Most first-time managers have never actually practiced management. They were promoted because they were good engineers, product managers, clinicians, or project leaders. Then one day they are expected to manage people. It at first seemed to be a perfectly reasonable assumption that practice would help.
The more I thought about it, though, the more I kept coming back to my own management career. Looking back, most of the coaching that mattered was not about building skills. It was about developing judgment.
More information wasn’t the problem
One thing that struck me is how much easier it has become to learn certain management mechanics. When I started managing people, finding good guidance was harder. Today there are books, podcasts, YouTube videos, and online courses that can explain how to run a one-on-one, deliver feedback, conduct a performance review, or delegate work. With AI, a chatbot can now walk a new manager through scripted, difficult conversations in real time nearly as well as a lot of paid external coaches can. The general mechanics are increasingly available and affordable to anyone willing to spend a few hours learning.
All that said, even general-purpose coaching from an outsider isn’t as specific as the narrow set of lessons the company itself has learned. I made this argument a few months ago in a previous post (“The Point of a Playbook”) about how AI with access to the general Internet can produce something confident and well-argued without ever considering what the company itself has learned. External coaching, whether led by consultants or AI chatbots, faces a similar problem.
If management time and training dollars are limited, where should organizations invest them? My instinct is that they should focus on the things that remain difficult to learn alone and are specific to the business. I believe the focus should be in tackling judgment problems rather than skill problems.
Delegation was rarely about delegation
One example that came to mind was customer engagement. For years I would tell product managers to go talk to customers. It sounded like a simple delegation decision. Assign responsibility, provide some direction, and let them learn. Over time I realized that talking to customers is itself a learned skill. The best customer support professionals do it differently than the best salespeople. The best salespeople do it differently than the best product managers. They ask different questions. They listen for different signals. They know how to separate symptoms from causes. They know how to handle objections without becoming defensive.
Years ago, product management usually meant spending real time in front of customers, at trade shows, on sales calls, and in support escalations. I could usually assume that an experienced product manager had picked up some of those skills through that kind of direct exposure. That assumption became less reliable over time. Many product managers today spend years operating primarily as product owners within agile organizations, which can involve very time-consuming tasks that are internally facing, including “grooming the backlog” in the bug database and coordinating development work. Some have surprisingly little experience with outward-facing activities, such as direct customer conversations.
The challenge was never figuring out how to delegate customer engagement. The challenge was deciding whether this person was ready for that responsibility. That was a judgment call.
Performance issues are often diagnosis issues
I saw something similar with performance management. Most management training focuses on the conversation.
How do I deliver difficult feedback?
How do I hold someone accountable?
How do I conduct a performance discussion?
Those are useful skills, but they were rarely the hardest part of the problem.
I spent much of my career working on initiatives that depended on multiple organizations moving in the same direction. When goals were missed, there was often no obvious explanation. Sometimes another team failed to align. Sometimes priorities shifted. Sometimes management had not removed obstacles. Sometimes the employee was not advocating effectively. Sometimes the employee simply was not performing.
From a distance, all those situations looked remarkably similar. I can think of several cases where product plans drifted for months because organizations could not align around a direction. Eventually I concluded that the product manager closest to the issue needed to create that alignment and wasn’t doing so. In those situations, I ended up making difficult personnel decisions.
I also saw this from the other side, where the problem wasn’t with a specific product but with the business direction itself. I recently wrote about my experience at Latitude Communications (“How My First Three Jobs Wore on Me”), where we could see WebEx going after a different buyer than the one we were selling to. We understood where things were heading. We just didn’t have it in us as a team to walk away from the model we had already built and proven. That gap, between understanding a problem and being able to act on it, is its own story, and it’s a harder one than a generic skills-based coaching program can drill into.
In these cases, the hard part was not conducting any performance discussion. The hard part was figuring out what problems we were looking at.
The coaching I remember most
The best coaching I received followed a similar pattern. Very little of it was tactical. Most of it was about helping me see a situation differently.
One lesson that stuck with me involved competing initiatives. Early in my career, my instinct was often to block projects that threatened something my team was trying to accomplish. I viewed them as obstacles that needed to be removed.
Several experienced leaders taught me a different approach. It is often easier to redirect than to block. Large organizations always contain competing priorities. Trying to stop them outright often creates more resistance than it solves. Finding ways to steer them away from conflict is frequently more effective.
The lesson was not the tactic itself. The lesson was learning when a situation called for redirection instead of confrontation. Once again, that was a judgment problem.
The curriculum was never the product
Prior to reviewing the latest version of my friend’s management training pitch, I told him a second-hand story about the Pro Club in Redmond and its partnership with Microsoft on an employee weight loss program. I had a couple of friends that went through it. To me, the curriculum, which included aerobic, strength, and core training, wasn’t what made it work. Any gym has those curriculum elements. What fascinated me was the accountability structure the partnership created with the attention of the trainers (including having trainers actually design, observe, and evaluate the workouts) and the financial incentives (reimbursements) associated with achieving milestones. The Pro Club understood the mechanics of management that worked with the Microsoft employee base. The curriculum that could be easily replicated across many gyms was the commodity. The value-add was in the judgment and ability to apply company-specific knowledge to differentiate itself.
I think a lot of the leadership coaching business runs on a different skill than the one it’s selling. The most successful coaches are often just the most likeable people and the ones that clients feel understood by. In some sense, this is closer to therapy than it is to business judgment. If clients walk out of sessions feeling better, they might mistake that feeling for having been helped strategically. These aren’t the same thing. Judgment is hard to package and hard to prove. Rapport, on the other hand, sells itself right away.
When I coach executives myself (see “Executive Coaching with a Retiree”), I default to interview-based 360-degree assessments instead of surveys. A survey can provide metrics, but it can’t expose what to do about it. Interviews are slower and more expensive to run, but my experience is that this is where the judgment problems show up. I hear specific stories from people who work closely with the executive, and not just some number on a Likert scale.
What should management training optimize for?
This is where I find myself wrestling with the dojo concept. In martial arts, a dojo can train students on a fixed set of katas until they are reflexive. It can train students on known forms for competition that earn points. Management, in general, doesn’t work that way because there’s no fixed kata to figure out whether a plan drifted because of politics, shifting priorities, or a manager that wasn’t doing their job. The hard part wasn’t executing known moves well but rather recognizing the move a situation calls for.
Even when practice includes live, improvised roleplay rather than a fixed script, the exercise is only as good as the judgment behind whoever built the scenarios and reacts in the room. That judgment usually comes from having lived through the specific situations being practiced. A program built to work across many companies and industries has a harder time embedding that kind of judgment than one built inside a single business, no matter how adaptive the roleplay itself is.
Of course, I think the dojo probably works somewhat for teaching certain skills. New managers might benefit some from practicing feedback conversations, delegation discussions, conflict resolution, and accountability. Repetition can build confidence and competence.
Where the money should actually go
What I am less certain about is whether skills practice like this is the highest-value use of management attention and budget.
Apprenticeship doesn’t need to work the same way for everyone. The mechanics, especially now that AI can teach them cheaply and at scale, can reach every manager. The harder kind of development, close observation from someone experienced, has to be concentrated somewhere. My instinct is that it belongs at the specific moments where a judgment call actually has weight, not spread evenly across a training calendar.
The management lessons that changed my career were rarely about what to say. They were about how to interpret a situation. They were about understanding root causes, recognizing patterns, identifying tradeoffs, and knowing which problem needed to be solved. Those lessons were difficult to learn from books. They were difficult to learn from videos. They usually came from experienced leaders helping me think through messy situations where the answers were not obvious. It was also observing seasoned managers navigating business situations.
That makes me wonder whether the highest-return form of management development looks less like training and more like apprenticeship. In my own style, I liked sitting in the open cubes with my teams so we could have visibility into each other’s work. Of course, this only works at a certain scale. More than one CEO or HR department has eventually banished me back into an office. Still, even at Barracuda, our CEO once moved a new hire executive into my office, and we shared it for months before he was ultimately asked to replace one of my peers. I didn’t think of it at the time as a program at all. Looking back, it wasn’t a dojo. It was something closer to watching the judgment behind a decision happen in real time, which is exactly the part no dojo can teach.
Note on this post: This piece originated as feedback I put together for a friend. I used AI to help reframe my thoughts objectively, focusing on sharing my perspective without sounding too prescriptive. At his suggestion over beers, I’m posting this to Substack “as-is” with some light edits. While my recent posts have been hand-written, I wanted to preserve the original format of this particular piece.
Neat article! I did a riff off it by discussing how parents can mentor their children in leading and following. It's over at Wholesome Tips and links back here: https://wholesometips.substack.com/p/lead-follow