Your leadership team probably needs a coach if the same problems keep surviving your attempts to fix them. Smart teams solve solvable problems. When a pattern outlasts two reorgs, three offsites, and a leadership book club, something inside the team is protecting it, and inside jobs are hard to see from inside.
Full disclosure: I do this work for a living, so weigh my answer accordingly. I'll try to earn the trust back by telling you when coaching is the wrong call, because it often is, and taking those engagements anyway is how this industry got its reputation.
What are the signs a leadership team needs a coach?
The biggest one is recurrence. The conflict between Sales and Ops that you resolved in 2024 is back, wearing a different costume. The strategy that everyone committed to is quietly dying again, stalled at the same stage as the last two. When a problem keeps coming back after competent people address it, the visible problem usually has a bodyguard, some dynamic in the team nobody can name from the inside.
The second sign: you've become the translator. Your CFO tells you what she really thinks of the expansion plan. Your COO tells you what he really thinks of the CFO. Neither says any of it in the meeting, so you spend your week carrying messages between adults, lightly editing for diplomacy.
The third is quieter and most CEOs miss it in themselves: you've stopped bringing your real problems to your own team. Somewhere along the way you concluded the room couldn't handle them, so the big questions live in your head and your spouse's evenings. Your most expensive meeting has become a status update.
When is coaching the wrong answer?
More often than coaches admit.
If you already know two people on the team need to exit, that's a decision, and you should make it. I've watched CEOs hire a coach as a way to delay a firing they'd already decided on, hoping six months of facilitated conversation would make it unnecessary or at least make it someone else's idea. It does neither. It costs a fee and a year.
If the strategy is the problem, fix the strategy. A team that's aligned, honest, and rowing hard in the wrong direction needs a different conversation than the one I sell.
And if you want the team fixed but don't intend to be in the room, save your money. The CEO is part of every executive team pattern, every time, no exceptions in my files. A coach working around the CEO is doing theater.
What does a team coach actually do?
The useful version of this work happens inside your real meetings, with your real decisions on the table. Offsite exercises have their place, but the job is mostly sitting in the room where the team actually operates and naming what the team has agreed not to notice.
A moment from a client engagement, because the work is easier to show than describe. The leadership team had just politely approved a plan. Nods all around. I asked the COO one question: "What would you say about this plan if your CEO weren't in the room?" Long pause. Then she answered honestly, and the real meeting started, the one they'd been not-having for a year. That question only worked because weeks of trust-building came first; cold, it would have gotten a polite deflection. The truth-telling it opened is what let the team eventually own the plan rather than comply with it. A good coach is essentially a mechanic for that progression, finding which link is missing and building it in the right order, and the Six Shifts is the diagram I work from.
What a coach can't do: want it more than you do, substitute for decisions you're avoiding, or change a team that's only in the room because attendance was mandatory.
Where this leaves you
Run a simple cost estimate before deciding anything. Take the pattern that keeps recurring and put a number on it: the initiative it stalled, the executive who left because of it, the quarters of drift. CEOs who do this honestly usually land somewhere uncomfortable, because team dysfunction compounds quietly. Against that number, the decision about getting help gets a lot less abstract.
Then, whatever you decide about a coach, have the conversation with your team that you've been having about them. That one's free, and it's diagnostic: how the room handles it will tell you most of what you need to know.