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Four ways to determine if a coach is a good fit for you


Here are four questions you can ask a professional coach when you are first evaluating whether they are a good fit for working with you.

How would you describe your coaching style?

Are they more supportive/encouraging or challenging/forward? Focused on identifying deeper root causes or prompting you to take action? Interested in social/contextual dynamics or helping you discover why you behave how you do?

What results can I anticipate from coaching with you?

Don’t hesitate to press for examples of what most coachees walk away with, or what, specifically, is different about them by the end of the engagement. What will they relentlessly commit to offering you?

How do you move people through blocks they’re having?

This will give you a better sense for what techniques they’re likely to use when things get tough and you risk defaulting to how you’ve always done things. Again, probe for concrete examples (or throw them an obstacle you’re currently grappling with and ask how they might approach leading you beyond it).

Bring a specific example of a blocker / issue

You may be struggling with something specific at the moment, which you can bring up in this initial session. Ask your coach to briefly coach you through it, so you can experience their style and approach. This will also let you have a comparison of how different coaches you’re interviewing approach the same issue.


As part of my amplify and reduce goals for April, I’m working on interviewing coaches to work with. In my initial chats so far, I found that the last example was the most insightful. After evaluating two coaches, there was a distinctly different feeling between the two in how they approached a specific example that I offered.

Note that even if you are not doing formal coaching and are just considering whether to get help from a friend or professional acquaintance, you can use a variation of these questions.

These are useful but don’t get too hung up on analyzing, the best thing to do is to start getting coached and see what works for you where you are at now. Everyone needs a coach.

🗒 Portions of this content came from my professional coaching program that I am doing at Automattic.
I do work there and you can too. 😃

Comments welcome!

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