How to vet your CEO coach

The specifics I myself look for when hiring a coach, and how I tell who's "got it"

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Hiring a coach can be among the highest leverage decisions you can make as a CEO. But hiring the wrong coach can be as catastrophic as a bad executive hire. 

I’ve found myself recently in the enviable position of getting to vet many wonderful coaches as Inside-Out Leadership’s talent pool grows. While the way I vet for coaches may not be for everyone, ultimately I am looking for the type of coach that I would want to work with, both now, and in my past as a CEO of a high growth company. 

So here’s how I’d suggest thinking about finding the right CEO coach, for those looking.

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How to Vet your CEO Coach

Coaching is about change. All engagements with a coach should help to drive tangible change in your business or life, but not all changes work the same. This is why the distinction between technical vs adaptive change is so important to understanding and vetting coaches. 

I’ve written extensively about this distinction before, but in summary: 

• To some of you, the instructions “delegate more effectively” would be technical. As in, once you receive the instructions, assuming you were motivated, you’d be successful in implementing them. You might ask for a bit of info on the types of delegation, or at what level to delegate each task – clarifying questions – but afterward you could implement and succeed at delegating without much trouble. 

• To others, the same instructions would be adaptive. As in, when you receive the instructions, even if you get them alongside techniques and strategies, you would attempt to implement them but would fail. Not because the techniques were incorrect, but because something about the way you approached them or implemented them was incompatible with a successful result. 

The process of making a technical change is usually a matter of ensuring you have the right information, context, and motivation. Whereas the process of making an adaptive change is more involved, often necessitating a repatterning of the emotional learnings that drive much of your subconscious behavior. 

On the path to getting where you’re going as a leader, you’ll run into many technical goals, and a few really meaningful, challenging adaptive ones. So it’s important to find a coach who can support you in both. 

Vetting for technical support

The primary way to vet whether someone can support you on the technical side of scaling a company is whether or not they’ve done it themselves. You don’t truly know the specific type of quiet confidence needed for a fundraise, or the nuance of resolving cofounder conflict, or the inner rewiring needed to scale a company unless you yourself have gone through those crucibles. This is why so many former athletes become coaches at the sport they used to play – they know what great looks like, and they’ve lived and breathed the process of getting there. 

But just like not all former sports superstars can coach, not all CEOs who have scaled companies make great guides. There’s a reason you don’t see Michael Jordan or Magic Johnson coaching NBA teams: they were too naturally talented. Excelling at the game came naturally to them, so while they were outstanding performers, they’re not much use when the game doesn’t come as naturally to someone else. The best basketball coaches were typically journeymen as players, who had to work harder than everyone else to maximize mediocre natural gifts (shout out Steve Kerr and Dan Campbell). They understand not only what great looks like but also the messy process of getting there as a normal human.

Accordingly, what you’re really looking for as far as technical skills is someone who was successful in scaling a company in the same role as the client (CEO works with CEO, etc) but who had to work particularly hard for their success. War stories about how badly things went, or how difficult the journey was, and how they adapted their approach to eventually find success, are all good signs here. 

Vetting for adaptive support

Vetting for adaptive support is harder, mostly because if a coach has founded, funded, scaled, and sold a company, you can expect that they are technically adept. Whereas there is no external metric that can give you the same confidence as to a person’s capacity to support in adaptive change. 

One way to assess these skills is to ask if the coach has any formal training in adaptive change. Formal certifications in transformational coaching, NLP, IFS, memory reconsolidation, mindfulness/Buddhism, psychedelic integration, and the like are indicators that the person has at least been exposed to the process of supporting adaptive change. 

However, having gone through many training processes like these myself, I can also attest to the fact that graduating from a coaching training program doesn’t always mean you can do this work. I’ve met many folks who have completed training programs who I would not want to coach me. And many of the best coaches I’ve worked with have no formal training. 

Another aspect is experience—if they’ve been successfully coaching for years, they must be doing something right. Again, this number can be helpful, but I’ve also met very experienced coaches who have lost touch with the cutting edge of the industry, so again, it’s not a given that experienced coaches are more adept. 

At the end of the day, the only way I’ve found to truly vet a coach’s ability to support a client in adaptive change is to have a conversation with them. During this conversation, bring them something persistent about your personality or beliefs you want to change, and see how they work with it. Do they stay talking about it? Or can they guide you on a journey to actually interacting with the issue, and then shifting your relationship with it in the moment? You’ll know you found the right fit for adaptive change when that thing that has been a limitation of your personality for the longest time feels slightly different after talking with them. Yes, the best adaptive coaches can drive a surprising amount of internal change in a person in a single session.

What if I have to choose? 

If you’re looking for a personal therapist, you don’t need someone who’s scaled a company. And if you’re looking for an advisor to weigh in on your strategy, you don’t need someone who can help you change your psychology. 

But if you’re looking to level up as a leader, the meat of that work is in the interplay between your psychology and the psychology of your company. So having a single person who can see and work skillfully with both your psychology and that of your company is key. In my experience having one person who can navigate the interactions between both levels is 10x more effective than finding separate experts in each and trying to combine them yourself. 

In other words, if you think you have to choose, I encourage you to keep looking. 

So now that we’ve covered the hard skills that I look for in a great coach, it’s time to discuss the equally important, soft skills: presence and fit. 

Vetting for presence

By presence, I mean a person’s residing fully and completely in the present moment. Unguarded, open, and receptive to what the moment brings, without agenda, the need to protect themselves, or steer anything. Someone who is completely, 100% comfortable in their own skin, who knows themselves well enough (both the light and the shadow) that they can clear themselves of their own patterns in the moment, in support of letting yours have center stage.

Presence is a vitally important attribute in a coach because the nature of coaching involves working with your triggers, well-established behavior patterns, and fear. It’s complex enough to navigate those topics in your own psyche. It’s all but impossible if you’re also navigating the same within your coach’s psyche. 

Presence is harder to vet for from a LinkedIn bio, but it is usually pretty noticeable when meeting a person in real life or even over Zoom. Most people have a ton going on in their minds. They’re distracted, buzzing, and driven by an agenda. They talk a lot. You get a sense that they want you to know how smart they are, how capable. They sell you, maybe. Everyone is so busy with their internal agenda in this way that when you do meet someone who is simply here, without agenda, it stands out like a sore thumb. 

And, what you’ll find in being around a person like that, is you find yourself naturally expanding into the conversation, becoming more present and sharing more deeply of yourself, simply because of the contact with their presence.

That experience is what you’re looking for. The coaching relationship asks you to go to places you otherwise wouldn’t. This type of deep presence is what enables that. 

Vetting for fit

And, finally, when evaluating the right coach for you, fit really matters. 

Your coach will likely become one of the closest relationships you have. One in which you are open to a greater degree than any other relationship in your life. One in which you will be vulnerable, make mistakes, be uncertain, and confront all of the habits and mental patterns that have created your life. A great coach can help you navigate all those things. But YOUR coach will make you feel naturally comfortable and at home in doing so. 

Do you want a cheerleader? Or a drill sergeant? An empath or a nerd? Great coaches come in all shapes and sizes, each of whom you will relate with differently. 

There’s only one way to evaluate fit that I know of, and that’s to talk to a number of coaches and gauge fit with each in comparison. 

Conclusion

There are four key criteria to consider in vetting for the right executive coach for you:

1. Technical skills

2. Adaptive skills

3. Presence 

4. Fit

Looking at their backgrounds makes it relatively simple to weed out many coaches based on criteria number one. And to a limited degree, you can weed out some based on number two as well (at least those who have no training or for whom you have no reference). But to truly vet for numbers two through four, you need to talk to someone in person. 

If I were hiring a coach today, I would seek out three to five coaches who have the appropriate technical skills, and who likely have the relevant adaptive skills, based on their training or on a warm reference. And I would then schedule back-to-back calls with each of them, bringing a thorny, adaptive issue to the table each time. I’d go into each call with the intention of being fully present and getting the most out of each one as a client. And then, afterward, I’d review each call and gauge which fit the latter three criteria the best. 

While it’s harder to empirically validate a coach’s skills than say a CRO or CTO, there are enormous, evident differences between coaches along each of the preceding four vectors. 

Hiring a coach can be one of the highest leverage decisions you can make as a CEO. The bar for hiring a coach should be as high or higher than if you were hiring someone to your executive team.

And, if you’re looking for a coach, I’ve pre-vetted all the coaches at Inside-Out based on their technical skills, adaptive skills, and presence. Simply reply to this email if you’d like to explore fit. 

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Executive Coaching for Entrepreneurs

I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency built by entrepreneurs, for entrepreneurs.

Through a unique combination of deep executive coaching and strategic execution support, Inside-Out has supported entrepreneurs leading some of the fastest growing companies in the world to develop into world-class leaders, and build high-performance, low-drama companies.

We coach leaders how we want to be coached:

• Focused on the person, not the role.

• Focused on results, without the fluff.

To learn more about working with I-O,  click here.