Peer group coaching · A working proposal
The honest secret of every great peer group is that the members coach each other. That is not the argument against a coach — it is the argument for one. Peer-to-peer only compounds when someone builds the container: levels the room, designs the sessions, processes the real issues, and follows each member out of the meeting and back into their company.
Every stalled peer group I’ve seen was full of impressive, generous people. The failure is never the members. It’s the missing structure around them.
WhatsApp threads and ad-hoc calls feel like community, and for a while they are. But nothing gets processed, nothing compounds, and the member who most needs the room is precisely the one who goes quiet in the thread.
Past six or seven, a meeting becomes a round of updates. Meet every other month at that size and each member is genuinely worked on for minutes per year. The thing everyone joined for — being coached by peers — structurally cannot happen.
Wins get shared. The hard thing stays in the parking lot. Without someone licensed to name what is actually on the table, a peer group of impressive people becomes a dinner club: excellent company, nothing changes.
Scheduling, preparation, follow-through, the annual trip — someone has to own the machinery. When it’s everyone’s side project, cadence slips, and a group that slips twice rarely meets a third time.
You can hire competent basic facilitation for about $5,000 — I know several people who’d do it well, and if a smoothly run meeting is all your group needs, that is the right purchase. But a facilitator makes the meeting go well. A coach makes the members go further.
Facilitator ·Runs the agenda and keeps time. The meeting goes well.
Coach ·Designs the session, reads the room, and abandons the agenda the moment the real issue surfaces — then processes it, all the way down.
Facilitator ·Brings a process, not a point of view.
Coach ·Brings frameworks, leveling, and issue processing built over a decade of running executive peer groups — and the judgment to know which one this moment needs.
Facilitator ·Sends the calendar invite.
Coach ·Coordination, preparation, follow-ups on every commitment made in the room, 1:1 sessions where the group surfaces something personal, and introductions across a wide operator network.
Facilitator ·Out of scope.
Coach ·A working operator and builder. In the age of AI especially, your coach should be someone who can jump in, get tactical, and has shipped with these tools — not someone describing them secondhand.
Facilitator ·About $5,000 a year.
Coach ·$10,000 per member per year — priced against what a stalled year costs a CEO.
Leading a group of high-powered CEOs and founders is not for the faint of heart. It requires expertise, empathy, coaching, and world-class facilitation — and most of the work happens where no one sees it, between the meetings.
A group of twelve to fifteen doesn’t need a bigger meeting. It needs a better structure.
The full group is split into small peer groups using my leveling strategy for CEOs, so every conversation happens between genuine peers — same altitude, same class of problem. In a group of five, everyone gets the table, every session.
I coach all of the groups. Patterns travel: what one room is struggling with, another has solved, and I’m the connective tissue between them — including the introductions that should happen and otherwise wouldn’t.
The whole community convenes once or twice a year, anchored by a two-day destination gathering. The small groups do the work; the large group keeps the bond.
The best thing in the room is each other — my job is to make that true more often, not to be the show. I build the container, level the room, and coach members to coach each other better.
A fair question, and one every member should ask. Here is the answer, in full.
per member, per year — or $1,000 a month to start.
No venue markups · no content licensing fees
For comparison: one good executive conference costs more, lasts three days, and nobody there knows your company. This is a room that knows your numbers, your team, and your patterns — meeting all year, led by someone accountable for what it produces.
Whether your group already exists and needs a structure, or you’re four CEOs away from having one — the first conversation costs nothing and usually settles the question.