217: Read This Before You Hire an Executive / Founder Coach

So you're thinking about whether coaching might be right for you. Here's my advice on what to consider before you decide to hire someone.

What Do You Want Out of Coaching?

There are ultimately 3 really valuable things the right coach can provide:

1. Clarity—figuring out what's next for your business / professional aspirations. Where do you want to go? A great coach can help you articulate an ambitious vision that is authentically aligned with your values, strengths, and the kind of life you want to live.
2. Conviction—developing the belief in your ability to execute on that ambitious vision. Sometimes we have setbacks or periods of struggle or rejection that can make us doubt ourselves. A great coach can help you rebuild your confidence through both internal work and guiding you towards actions and pursuits that will prove to yourself and others that you've got what it takes.
3. Momentum—making faster and more effective progress towards your ambitious vision. Even when you know where you want to go and believe you can get there, it can still be a slog. A great coach can help you navigate pitfalls and provide guidance, resources, and tactical help in achieving better outcomes.

What Kind of Qualities Should You Seek in a Coach?

So you know what you want out of a potential coach. You start looking for coaches who might fit the bill and ask around friends and colleagues for rec's. What are you looking for as you make a short list and set up intro calls?

1. Experience and judgement—you want to find a coach who has a lot of context and perspective in the areas of your aspirations. That can come from direct experience—having started or led companies, or indirect—having interviewed, researched, or written extensively about entrepreneurship / executive leadership. Do they have the necessary depth to provide you good counsel?
2. Sense of kinship—one of the most important factors in a successful coaching engagement is the sense of connection or alliance between coach and client. Do you relate to this person? Can you trust and be open and vulnerable with them? Do you respect and like them enough to go through difficult experiences with them and accept their feedback and ideas?
3. A generative spirit—coaching is like improv. You and your coach will be exploring, creating, and discovering new things in every session. So you should feel like this person awakens things for you. They give you new information, ask interesting questions, provides insights on your challenges and gives you new perspectives on your problems.

How Does Coaching Differ from Therapy?

In August 2024, the New York Times published a piece called "How ‘Coaching’ Became Silicon Valley’s Hack for Therapy" which explored the growing popularity of executive coaching for startup founders and tech executives.

Sensational title aside, the piece actually does a pretty fair job of looking at how coaching differs from therapy including:

• Therapy is a state-regulated occupation which comes with a number of restrictions on how therapists can and cannot work with clients (meeting when you're not in the same state, revealing much about themselves, or talking to anyone else in the client's life)
• Coaching is a free market title—anyone can call themselves a coach and the way coaches operate is much more open-ended (you can work with your friend's coach, your coach can meet when you're on the road, coaches can share much more about themselves)
• Traditional therapy often focuses on past traumas, fixing what’s ”wrong” with you, and will likely require a psychiatric diagnosis to be covered by insurance, and often take weeks, months, even years to make progress
• Coaching is more future and goal oriented, focused on building on your strengths, is widely accepted as a valid business expense by investors and boards, and can often generate more immediate progress or results

In my experience, it’s not really a competition. There's a place for both.

I've found that my clients who have done or are doing therapy alongside coaching are more in tune with their own feelings, can go deeper into the motivations for why they made certain decisions, and are less defensive when I push them on things. Basically they're more emotionally intelligent, which makes them more able to embrace a new perspective or confront a limiting belief and thus move more quickly.

Just like how both strength & conditioning work and mobility / PT work can be helpful in improving an athlete's performance—therapy and coaching can work together.

My Founder Coaching Hot Takes

Lastly, let me share a few more contrarian takes on coaching. I'm not going to say these are definitively true but they form part of my perspective on coaching.

• Coaching is not a magic bullet. If you have little experience in a field or lack a big network or have not developed strong technical or business skills, you cannot not expect any coach to radically change that overnight.
• Most influencer coaches are better at creating content than actually helping their clients succeed (I promise not to remove this take even after I hit 100k+ followers)
• The idea that coaching isn't regulated profession and therefore dangerous is as silly as saying that management is not a regulated profession and therefore dangerous. In the end, you have to use your own judgement.
• No matter how close you are to your investors, they don't have the time, aptitude or incentive to truly care about your best interests first and foremost.
• As a coach, I care more about your personal growth than your business success.
• Your company will almost certainly not be the next Airbnb, OpenAI, or Tesla. And yet entrepreneurship can be an incredibly fulfilling, rewarding, and meaningful experience.
• Most entrepreneurs are outliers in some major way—neurodivergent (dyslexic, ADHD, ASD, etc), have huge chip on their shoulder, or are just wildly ambitious and deeply dissatisfied with their currently reality.

Working with Me

If you still think coaching is right for you and what I shared resonated, I'd invite you to explore my actual coaching page where you can learn more about my approach, read testimonials from past clients, and book an intro vision mapping session.