How to Choose an Executive Coach Who Knows Your Stage

Choose an executive coach who understands founders at your stage, has real coaching skill, and has frameworks built for the outcome you want. Gene Hammett, founder of Core Elevation, says that the best coaches know the problems you face better than you do because they’ve taken many founders through the same transition.

I’m Gene, and I’m a buyer too. I’ve hired my own coaches for sales, for marketing, for speaking, and even for coaching itself, so here is how to choose an executive coach from someone who still writes those checks.

Match the Coach to Your Stage and Your Goal

Most founders start the search with the wrong question. They ask, “Who’s a good coach?”

The better question is, “Who’s good at the exact shift I need to make next?” I call that “stage fit,” and in my experience it decides more coaching engagements than price, location, or a polished website ever will.

Write Down the Shift You Need First

Before you talk to a single coach, grab a pen and a legal pad and give yourself five minutes. Write down the one thing that has to be different in your company a year from now, in plain words.

“I want to be a better leader” is too vague to hire against. “I want my leadership team running the weekly numbers meeting without me in the room” is a shift a coach can say yes or no to.

You might be thinking you’ll figure out the goal with the coach. Some of that is fair, and a good coach will sharpen it, but you still need a starting point so you can tell which coaches are built for it. Once you’ve picked someone, my guide on how to set strong coaching goals will help you sharpen it together.

Find Someone Who Understands Founders

Here’s the line I give every founder who asks me about this: “If you are a founder and a CEO, you want someone who understands founders and CEOs.”

A coach who has only worked inside big corporations can be excellent at what they do. But a founder goes through identity shifts that a corporate executive rarely faces, and a corporate-only coach often doesn’t see them coming.

I lived the firefighter row for years in my first business. I was proud of being the guy who could fix anything (a little too proud, if I’m honest), and I felt the tightness in my chest every time my phone lit up, because I knew the next fire was mine to put out.

On Growth Think Tank, I’ve sat across from more than 1,200 people who run fast-growth companies, and in hundreds of those conversations the same stage problems keep coming up. So look hard at who the coach has worked with.

“You should be looking at people who understand where you are and know the problems you’re facing better than you do, because they’ve been through it so many times.”

Ron Dod, co-founder of Visiture, said, “Gene definitely helped me transition from those moments and really helped me grow as an individual.” Ron did the work, and he gets the credit. My job was to know the transition he was in and walk it with him.

Hire a Specialist for Each Domain

“Every coach should be focusing on specific aspects of coaching.” When a coach tells you they help everyone with everything, keep looking.

I have followed that rule as a buyer for years. I picked each of my coaches for one domain and for the stage I was in, and every one of them provided some level of transformation.

Still deciding whether to hire anyone at all? Read my answer on whether executive coaching is worth it first, then come back here and narrow the field.

Weigh Pattern Experience Over a Matching Resume

A coach does not have to have done everything you’re doing. I’ve coached founders through raising money, and I’ve never raised money myself.

What carries across is coaching skill and pattern experience. Ask how many founders the coach has taken through your specific transition, and listen for whether they can tell you how that transition usually goes wrong.

The same goes for your industry. A 50-person software company and a 50-person construction firm often stall for the same reasons: the founder is still the bottleneck, the managers wait for answers, and the culture leans on one person.

So when a coach says they’ve never worked in your industry, do not stop there. Ask whether they’ve worked with companies your size, at your stage, with your kind of problem.

Check Coaching Skill and Credentials Without Overrating Them

Coaching is a crowded field. The 2025 ICF Global Coaching Study counted a record 122,974 coach practitioners around the world.

In that same study, 73 percent of coaches said their clients and the companies that hire them expect a certification or credential. Certification is not required to coach anyone, but it shows a coach takes the craft seriously.

My own business collapsed in 2010, when I lost more than $3 million in one day, and I rebuilt my working life around coaching founders. I earned my coaching certification from Newfield Network in 2011, and I still learn something from every client I work with.

Here’s the split I want you to see. A credential is proof of training, and coaching skill is what happens in the room.

Coaching skill shows up in the first conversation. Notice how well the coach listens, and whether their questions make you think harder than you planned to.

Know the Difference Between Motivational and Transformational Coaching

Two very different products get sold under the same word. I’ll be honest about where I stand.

“Motivational coaching is the essence of someone trying to be your cheerleader, pump you up, and get you to believe in yourself. There is value to that, but the work I do is deeper.”

In other words, a pep talk lasts until the next fire lands on your desk on Monday morning. Transformational coaching changes the way you lead, so the change holds long after the session ends.

So which one are you shopping for? What if the coach who makes you feel great on the first call is the wrong one?

My stance with every client is simple: “I want you to motivate yourself.” My job is to show you the path and the tools, then hold you to the walk.

Look for Frameworks Built for the Outcome You Want

Every coach I’ve hired had a way of working I could see. That’s why I tell founders to find a coach whose frameworks, tools, and programs are built for the promise they want.

Here’s a quick test. Ask the coach to sketch their path for a founder like you, start to finish, in five minutes.

A real framework usually gives you four things:

• ●A starting point. A clear way to measure where you are today, before any coaching starts.
• ●A sequence. The steps you’ll take, in order, and why that order matters at your stage.
• ●Tools. Things you use between sessions, so the work keeps moving when the coach isn’t in the room.
• ●A way to see progress. Signs you can point to that the shift is actually happening.

At Core Elevation, the founder work starts with CEO Foundation. We look at four areas of your leadership: where your time goes, how you give your people real authority, the way you communicate, and the identity shift from operator to CEO.

You do not need my framework. You need one that fits the outcome you want, and a coach who can explain it in plain English.

Choose a Coach Who Will Challenge You

“A lot of people are surrounded by people that are yes men, and they’re not challenging them.” Founders feel this more than most, since nearly everyone around them reports to them.

The gap at the top is real. A 2013 Stanford Graduate School of Business survey found that nearly two-thirds of CEOs got no coaching or leadership advice from anyone outside their company, even though almost every one of them said they enjoyed getting it.

Test the Chemistry Both Ways

You’ve heard “find a coach you click with” a hundred times. But are you testing whether that click comes with a push?

Chemistry matters, and it sits right next to stage fit and coaching skill on your list. “If chemistry is off, you feel like the person’s not going to challenge you, or the person’s too hard for you, then find someone else.”

Chemistry can go wrong in two directions. A coach can feel too soft to push you, or too hard for where you are right now, and either one is a good reason to keep looking.

Listen for the Question You Have Been Avoiding

On a good first call, the coach asks the one question you’ve been dodging. You’ll feel a little uncomfortable, maybe a little exposed.

Good. That feeling is a sign the coach sees something.

A coach who agrees with everything you say is one more voice in the room telling you you’re right. You already have plenty of those.

Ask These Questions on the Discovery Call

Bring the same short list to every discovery call, and ask each coach the same questions. Then lay the answers side by side.

Too busy for three discovery calls? You will spend months with whoever you pick, so a few hours now is the cheapest part of the whole decision.

If you’re weighing a whole firm against one coach, my guide to comparing executive coaching firms covers the questions that apply to firms.

Expect a Good Coach to Interview You Too

A strong coach checks whether you’re coachable before taking you on. Here are the three questions I ask every founder on a discovery call:

1. 1“How important is this to you right now on a scale of 1 to 10?”
2. 2“How committed, given everything that’s going on, are you to the transformation yourself?”
3. 3“How do you know you’re coachable?”

I ask, “How do you know you’re coachable?” and then I wait (the pause tells me a lot).

How would you answer that last one today?

At Core Elevation, the Clarity and Courage audit starts with an intake form of 20 to 25 questions that takes 20 to 30 minutes. The form measures where the founder is in numbers and in their own words, including what’s really happening in the culture.

A coach who takes anyone with a credit card is not screening for fit. When a coach asks you hard questions before you’ve paid a dollar, you’re getting a preview of how the coaching will feel.

Check the Track Record Through Client Stories

Read what clients say in their own words, with their names and companies attached. Our client stories on the results page show what that should look like.

Podcast conversations help too. On the Growth Think Tank podcast, you can hear how I think for a full episode at a time, long before you ever book a call.

As you read and listen, ask yourself one question. Do these stories describe a company like yours, at a stage like yours, with a problem like yours?

Score Every Coach on the Same Five Criteria

Once you’ve talked to two or three coaches, score each one against the same list. A simple scorecard keeps the decision from coming down to who was most charming on the call.

When one coach clearly wins, commit and go all in. If what you want is a leadership team that runs without you, see how our executive coaching for founders works.

Frequently Asked Questions

These are the questions founders ask me most when they’re choosing a coach.

Pick the Coach Who Knows Where You Are Headed

I started by telling you I’m a buyer too. From that seat, my rule is simple: hire the specialist who knows your stage and will tell you the truth, even when you don’t want to hear it.

So what is the one shift you wrote on that legal pad?

Which coach on your list has walked other founders through it?

Will that coach tell you the truth?

Hiring me is optional, and I mean that. If you’re ready to stop being the bottleneck, though, I would love to show you the path.

Lead with courage.