Executive career coaching

How to choose an executive coach

The market is unregulated, the credentials mean very little, and the sales process is usually more polished than the service. Here is how to test it in one conversation.

Seven questions

  • Who have you worked with at my level, in my function? Coaching a VP of Engineering and coaching a CFO are different jobs. Vague answers about "senior leaders" mean the answer is nobody.
  • What will exist at the end that does not exist now? Artefacts, not feelings. A positioning statement, a target list, a set of rehearsed conversations.
  • What do you not do? Anyone who claims to do everything — clarity, access, introductions, interview prep, negotiation — is describing a brochure rather than a practice.
  • Do you make introductions, and to whom specifically? Many imply a network. Ask for the shape of it: which sectors, which seniority, how many in the last year.
  • How many clients do you have right now? Thirty concurrent clients is a content business with a call attached.
  • What happens if it is not working at week six? A good answer involves changing approach or stopping. A bad one involves more sessions.
  • Can I speak to someone you worked with who did not get the outcome they wanted? The reaction to this question tells you more than the answer does.

Answers that should end it

"I have a proven system"

Senior searches are idiosyncratic. A system sold identically to everyone is a curriculum, and you are paying a premium for a course.

A guaranteed outcome

Nobody can guarantee a senior placement. Anyone offering one is either misleading you or has not thought about who actually makes the decision.

Urgency in the sale

Cohort closing, price rising, two places left. An advisor who manufactures pressure in the sale will not be a calm presence when your search stalls in month four.

Nothing you did not want to hear

If a first conversation about your career contains no uncomfortable observation, they are selling rather than assessing.

On credentials

Coaching certifications demonstrate that someone completed a coaching course. They do not demonstrate that the person understands how a board fills a chief-level seat. Weight operating experience and relevant placements far above letters after a name.

The cheapest useful test

Ask them to describe, specifically, what they would have you do in your first two weeks. Anyone who has done this work will answer in concrete detail and the plan will sound like effort. Anyone who has not will answer in stages with names like Discovery.

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See it against your own companies

A short call, your target list, and an honest answer about whether this fits how you are running your search.