A guide for founders choosing a coach: five things to look for, drawn from more than 1,600 coach interviews and the way the best founders pick theirs.
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Choosing a coach is hard and it matters. This person will guide you through high-stakes decisions and sensitive problems as the company scales, and the cost of bad advice is enormous. Coaches take time to get up to speed, so picking the right one first time is worth the effort. How to do that isn't obvious.
Over the past eight years we've interviewed more than 1,600 executive coaches and performance psychologists. Our coaches have supported the founders of Instagram, LinkedIn, Brex, Lattice, Tonal, VizAI and OpenSea, among others. Five things to look for, from watching the best founders do it.
Before committing, experience what working with them feels like. Take an introduction call and come with a real, pressing challenge: something top of mind that you actually want to solve. Treat it as a trial run.
The right coach leaves you clearer, more confident and holding a perspective you didn't have, not just heard. If the session feels generic or theoretical, or you leave more confused than you arrived, that's your answer.
It's tempting to pick a coach on shared experience, industry or temperament. It's human nature to choose people like us. Chemistry matters, but it isn't enough. The right coach isn't the one who shares your background. It's the one who challenges your assumptions and shows you your blind spots.
A strong coaching relationship isn't always comfortable. The best coaches hold you accountable, challenge your beliefs and make sure you don't settle into patterns that no longer serve you.
If a coach is easy to work with, you may not be getting the value you need. Growth requires discomfort. The right coach pushes you past your comfort zone and into the harder decisions.
Coaching isn't about good conversation. It's about results. Experienced coaches have a track record with high-performing leaders and companies, and they bring insight that applies to your problems.
Look for experience relevant to your stage, industry and leadership needs. Have they scaled companies like yours? Do they have results with founders hitting the roadblocks you're hitting?
You want to see progress, so understand how a coach works before you commit. How do they define success? How do they measure growth and track it over time? A great coach has a clear, structured approach, and will set expectations for what the process looks like and what outcomes you can expect.
Choosing a coach is an investment in your leadership and your company. The right one will challenge you, expand your thinking and accelerate your progress.
