How to Choose an Executive Coach
A lot of people are calling themselves coaches right now. With such a crowded field, I understand why that feels like a mess from where you're standing.
You're about to hand someone the most important challenges that are keeping you up at night. Maybe it’s the decision you can't make, the conversation you're avoiding, or the doubt you haven't shared with your team. It may feel like there's no good way to check whether someone is the right coach for you.
So, here's how I'd evaluate an executive coach and find your best match.
Talk to at least two other coaches before you decide, myself included. Fit matters more than anything on a website. If someone else feels right, go with them.
Here are the five questions I'd ask.
1. Have you ever sat in my chair?
Ask what they've actually run, built, or been responsible for. Not what they've studied. Helping someone through a big decision is different when you know what that decision truly feels like at 2 a.m.
My answer: I spent 20+ years in the design world as a creative director, design professor, and entrepreneur. I've run two product businesses, co-own restaurants, and I'm now building a software company. I've stood at plenty of important crossroads of my own. That doesn't make me the right coach for you, but it does mean I know the ground.
Watch out for: A coach who goes vague when you ask about their own experience, or who leads with certificates instead of experience.
2. Who do you work with, and who don't you work with?
A good coach can tell you in a sentence. "Everyone" is a bad sign.
My answer: I work with founders, entrepreneurs, and leaders at a turning point. That may be stepping into a bigger role, growing a business, or getting ready to sell or leave one. I'm a good fit for thoughtful, introverted, and sensitive leaders. I'm not your person if you want interview prep, a rigid framework, or someone who stays on the surface. My style is intuitive and direct, and some people find that too much.
Watch out for: Guaranteed outcomes, or a method that's the same for every client.
One more thing
Many people may hesitate before hiring a coach, especially when it's their own money. It is a big investment in both time and money, so that pause makes sense. A good coach can hear that and stay curious about it, not defensive.
Here's how I'd think about the cost:
Put it next to what a rough first year in a new role would cost you.
Or a rushed decision about selling a business.
Then ask who you'd trust to help you through it.
If you want to chat, book a fit call below and bring these five questions. Then go talk to two other coaches and see who feels like the right coach for you.
3. What will you tell me that the people around me can't?
Your team has something to protect. So does your board. Your family loves you. A friend will cheer you on. What's hard to find is someone with nothing riding on your answer who will clearly say what you've been glossing over.
My answer: I'll tell you what I'm noticing. I start gently, and then I ask the question that goes straight to it. Sometimes it's what you're avoiding. Sometimes it's the strength that got you here, now getting in your way. On our first call, before we ever talk about price, I'll give you one honest observation. Then you can feel how I work before you decide anything.
Watch out for: A discovery call where you only feel validated. If you hang up feeling great but you haven't learned anything, notice that.
4. What are your credentials, and what do they mean?
Credentials aren't everything, but they should be real and easy to check. Ask who certified them and at what level.
My answer: I'm an ICF Professional Certified Coach and a Co-Active Certified Coach who trained at Co-Active Training Institute. I've been coaching for 10 years and working in the design field for 20+ years. Take a look at my résumé here. I’m also happy to provide references to past clients.
Watch out for: Titles you can't verify, or a credential that's the main reason to hire them.
5. What does the work actually look like?
Ask how often you'll meet, what happens in between, and how you'll both know it's working.
My answer: My typical coaching package is 6 months of support, with twelve coaching sessions every two weeks and support in between. I go through every detail on a fit call, and we decide together if it's right or customize to match your situation. I never want you to feel pushed on that call. You’ll know it’s working because you will be reaching your goals with more peace and clarity than you can picture right now. Your behavior will shift, folks close to you will take notice, and important decisions become easier to make.
Watch out for: Fuzzy deliverables, pressure to decide on the spot, or no way to tell whether it helped.