Most executive coaching happens one person at a time, behind closed doors, and it is one of the most expensive ways to develop a group of managers I know of.
It is also, in most cases, not the fastest way to build better leaders. Group coaching usually is.
This is not the popular opinion in a market that loves the word “personalized.” But I have run enough coaching sessions with six to ten managers in a room, working through real problems together, to say this plainly: managers learn leadership faster from watching each other struggle with real problems than from a private conversation where they never see how anyone else handles the same situation.
Here is why. A manager who is quietly struggling with a poor-performing employee often assumes they are the only one facing it badly. Put them in a room with nine other managers, and within twenty minutes they discover that half the group is wrestling with a version of the same problem. That alone changes the conversation from “what is wrong with me” to “what is the actual pattern here, and how do we fix it.”
Group coaching also does something one-on-one advice cannot: it lets a manager practice explaining their own problem out loud, clearly, in front of peers who will ask direct questions. That is a leadership skill in itself. A manager who can articulate a messy real-world problem in two sentences, to a room that will push back if the explanation is vague, is building the exact communication muscle they need with their own team.
The structure matters more than the personalities in the room. I use a simple sequence: situation, problem, cause, options, action. Each manager brings one real issue — a difficult employee, a missed deadline, a delegation that went wrong, a conflicting priority. The group works through it using that structure, out loud, together. Nobody leaves with generic advice. Everybody leaves having watched a real problem get solved in front of them, which they can now apply to their own version of it.
Run this every two weeks, forty-five to sixty minutes, six to ten managers per group, and something compounds over a few months that individual coaching almost never produces: a group of managers who trust each other enough to ask for help before a small problem becomes a large one. That trust does not come from a private coaching relationship. It comes from watching your peers be honest about their struggles in a room where nobody got punished for it.
Companies often assume private coaching is more valuable because it is more expensive and feels more exclusive. In practice, for developing an entire layer of management at once, it is usually the slower, costlier option. Group coaching, structured well, builds both the individual skill and the peer network a manager will actually lean on after the program ends.
If this sounds like your team, send me a message. I’d like to hear about it.
If your managers are each quietly solving the same three or four problems alone, what would change if they finally solved them together?
Suggested next reading
- The Universities That Teach Students How to Work Will Win the Next Enrollment Race — https://jordanimutan.com/2026/08/14/the-universities-that-teach-students-how-to-work-will-win-the-next-enrollment-race/
- Stop Sending Managers to Training They Will Forget by Friday — https://jordanimutan.com/2026/08/12/stop-sending-managers-to-training-they-will-forget-by-friday/
- 92% of CHROs Expect Greater AI Integration. The Research Says the Human Variable Is What Determines Whether It Works. — https://jordanimutan.com/2026/08/07/92-of-chros-expect-greater-ai-integration-the-research-says-the-human-variable-is-what-determines-whether-it-works/
- 73% of Employees Say Lack of Trust Is the #1 Driver of Workplace Conflict. The Manager Creates It or Destroys It Daily. — https://jordanimutan.com/2026/08/05/73-of-employees-say-lack-of-trust-is-the-1-driver-of-workplace-conflict-the-manager-creates-it-or-destroys-it-daily/
- Leadership Development Is CHROs’ #1 Priority for the Second Year Running. The Method Still Isn’t Working. — https://jordanimutan.com/2026/07/31/leadership-development-is-chros-1-priority-for-the-second-year-running-the-method-still-isnt-working/
Most leadership training is forgotten after the seminar. 