The best coach in the world is still the wrong coach for half your leaders.
I understand why companies do what they do next. They find a coach or a firm they trust, someone who delivered real results for one or two people at the top, and the instinct is completely reasonable: let's scale this. One method, one style, one firm, rolled out across the whole leadership team.
It rarely works the way anyone hoped.
Development is a relationship before it's a methodology
And relationships run on fit, not on credentials or reputation. I've watched this play out too many times to think it's a coincidence.
Take two people on the same leadership team. An introverted engineer who's brilliant technically but processes everything internally before speaking, and a hard-charging sales leader who thinks out loud, in real time, mid-sentence.
These two people do not need the same coach. They may not even need the same kind of conversation. The engineer might need someone patient, someone who creates space and lets an answer surface slowly over several sessions rather than forcing it in the first one. The sales leader might need someone who pushes hard, fast and directly, because slow and gentle will just read as a waste of time.
Put the wrong coach in front of either of them, even a genuinely excellent coach, and the whole engagement stalls. Not because the coach lacks skill. Because the chemistry isn't there, and coaching without chemistry is just an expensive calendar hold.
"Fame within an industry doesn't predict fit with an individual person."
I've seen "the best coach" on a given firm's roster fall completely flat with someone who simply needed a different kind of presence in the room. Meanwhile, someone else on that roster who never gets the marquee assignments turns out to be exactly what a particular leader needed.
What a real matching process accounts for
Most matching in practice comes down to availability. Someone has capacity this quarter, so they get the engagement. That isn't a process, it's a rota.
A matching process worth the name accounts for at least four things.
The developmental need, stated specifically. "Executive presence" is not a need, it's a category. A leader who avoids conflict with a peer, a leader who can't delegate, and a leader who is technically superb but loses the room in a board setting all get filed under executive presence, and all need different people across the table.
Working style, on both sides. Pace, directness, how much silence a person can tolerate, whether they arrive at insight by talking or by thinking first. This is the dimension most often skipped, and the one that most often kills an engagement by session three.
Context the coach has actually operated in. Not industry trivia, but whether they have been close enough to the kind of pressure this leader is under to recognise it quickly. A first-time founder scaling past a hundred people and a divisional head inside a regulated multinational are living different problems.
A real chemistry check, with a real exit. Two or three conversations with different coaches before committing, and a stated, blame-free way to change coach after the first month. Most programmes technically allow a switch and culturally make it impossible — nobody wants to be the leader who "didn't get on with" their coach. If changing coach requires an act of courage, your matching process has a defect.
Where fit stops being the answer
I want to be careful not to overstate this, because "fit" can become an excuse.
Fit is not the same as comfort. The point of a good match is not that the leader enjoys every session. Some of the most valuable coaching relationships are ones the leader finds genuinely uncomfortable, because the coach is willing to say the thing everyone else in that person's life has decided not to say. A leader who has cycled through three coaches because none of them "felt right" may not have a matching problem. They may have a coachability problem, and that's a different conversation — usually one for their manager rather than their coach.
The distinction is worth holding onto: a good match creates enough trust to make discomfort productive. It does not remove the discomfort.
The question worth sitting with
If you're responsible for a coaching programme at your company: how were your coaches actually matched to your people?
Was there a real process, something that accounted for personality, communication style and what each leader actually needs to grow? Or did everyone just get assigned whoever was available that quarter?