Why top entrepreneurs (and VCs) invest in executive coaching - Part 1

"The team who sees reality best, wins." -- Jack Welch

Welcome entrepreneurs. I’m so glad you’re here.

After 10 days away from the computer, either in the Smokey Mountains or at home building snowmen with my kids, I’m ready to jump back in with both feet.

After years and years of “fearlessly” leading the charge like Alexander, sword in hand, “inspirational” anecdotes flying, it’s refreshing and centering to finally find my work in the deep stuff. The messy, human stuff, that at the end of the day underpins all our accomplishments, and the very reasons those accomplishments matter so much. I’m grateful to find my work in meeting some truly remarkable entrepreneurs in the gap between who they are and who they want to be. And, dear reader, I’m grateful to meet you in a frontier conversation about the future of entrepreneurship, whose outcome is yet in doubt.

Thus realigned to the work that is truly inspirational and important to me in 2021, let’s fucking do it.


Coaching is becoming an unfair advantage for top entrepreneurs. What is coaching, anyway?

I remember when I first hired a coach, while I was running VNN. It felt like something I had to hide. Like I was admitting I needed help, like I couldn’t do the job on my own. But over time I got over that and finally began to open up, and thus begun what has been the most transformational leadership journey of my life.

This was more than five years ago. And while there’s still that hurdle to initially hiring a coach for many people, it’s since become much more normalized.

Companies (and, increasingly VC funds) recognize the force multiplying effect of a coach dedicated to a high potential founder, and are increasingly investing in helping their leadership level-up. See this, this, this, this and this for what founders think, and this, this and this for the VC perspective.

But many people I talk to still don’t quite get it. What is coaching? What does it mean to have a coach, and what should I expect? And why has it become such a critical tool for top entrepreneurs?

Well, there’s no way I can do the discipline of coaching in its entirety justice in one post — most coaches I talk to say you have to experience it to understand it — but I’m going to begin to eat the elephant of defining executive coaching for entrepreneurs today.

For the first bite, let’s dive into how a trained coach helps entrepreneurs better see reality, and make better decisions, particularly in sensitive, high-pressure situations.

Leaders cannot see what’s right in front of them (the best ones admit it)

It’s nice to think that the way we see the world is the way the world is, but in reality the world we see is refracted and distorted through various lenses and filters in our consciousness. What’s at play here is your reticular activating system (RAS), which is the part of your brain responsible for you seeing your Volkswagen everywhere the moment you buy a new car. As a result, we don’t see reality — we see the part of reality our brain is conditioned to see, and miss the rest. (I wrote about how you can leverage this system to become happier, here.)

Skeptics, take a look at this image, depicting a rotating mask. Because our brains are so conditioned to see faces as convex entities, our brain automatically transforms the concave mask (when it’s facing away from you) into a convex face. This is how our brain distorts reality to fit into our mental model of what reality “should” look like:

The issue is that we’re mostly unaware of the specific mental models our brain’s using, so we go around thinking what we’re seeing is actually reality, not knowing which parts we’re over-indexing and which important parts of reality we’re completely blind to. (If you want to really dive into the science of it all, you could start from the experimentally unavoidable fact that there is no such thing as objective “reality,” but maybe that’s another post).

Either way, blind spots are a leader’s primary challenge to making good decisions, and to their own ability to grow over time. Successful leaders intentionally augment their limited perspective with those of others, to ensure they’re solving for the version of reality that most closely resembles actual reality. This means that effective leaders are constantly soliciting feedback from their teams, investors, and customers (the understanding that we must solicit alternative perspectives to help us see what’s right in front of us is the foundation of the Lean Startup movement, which is so effective it’s become the de facto “way” to build a company).

The best leaders understand that their perspective, as correct as it seems, is incomplete, and intentionally use their teams (both their leadership team & employees, as well as their investors and their family) to help them develop a more comprehensive view of reality.

“The team that sees reality the best wins.” — Jack Welch

But what about the sensitive stuff?

All that’s well and good, but, As Jackie Vullinghs from Airtree VC explains, “as your company grows, there are fewer and fewer people you can be (100%) honest with.” Said a different way, there are more and more situations in which the trusted people around you either don’t have sufficient context to help you see reality, or they do, but are conflicted.

For example:

  • When you know you need to level up as a leader to scale your company, but you aren’t sure where to start and don’t want to broadcast your weaknesses to your board.

  • When you receive a financing or acquisition offer which puts you in a great position but saddles some investors with a loss.

  • When you think your co-founder might not be up to the task of scaling the company, but you don’t want to let the genie out of the bottle before you’re sure.

  • When members of your leadership team aren’t working well together, but when confronted insist that they are.

  • When your instinct is your company culture has become a problem, but you’re still hitting numbers so you can’t be sure you aren’t imagining things.

I could go on.

It’s also worth noting that these are also usually the most high-stakes, mission-critical situations. So at the very time when you most need a comprehensive view of reality, when it’s your own performance or a critical company issue, you’re on your own.

This is why they say “it’s lonely at the top.” As true as that is, accepting leadership-myopia as an inevitable outcome of that reality is a mistake that less and less leaders are making.

So how does executive coaching help me better see reality?

Trained in psychology (and sometimes with a business background), an executive coach is an objective professional who creates a safe, confidential, and growth-oriented space for leaders to see, and overcome, their blind spots, and develop into the leader, and person, they want to be. Coaches are accountable exclusively to you (over and above your team, investors and even your company).

Through your relationship, a coach helps you develop an understanding of your own operating system — the way you think, your consistent blind spots, how you make decisions, what drives you, how your fears get in the way — and through that process helps you see reality more clearly. Seeing reality more clearly helps you make better decisions in critical situations, and helps you identify and overcome persistent blind spots or limiting beliefs holding you back from achieving your long term potential.

“I never cease to be amazed at the power of the coaching process to draw out the skills or talent that was previously hidden within an individual, and which invariably finds a way to solve a problem previously thought unsolvable.”

— John Russell — Managing Director, Harley Davidson

Jack Welch said, “the team that sees reality the best wins.” He didn’t say the person. Recognizing that they don’t have to do everything alone, top entrepreneurs across the country are hiring coaches, and then leveraging their augmented view of reality to win their markets, and reach their potential as leaders and human beings.

Yes, it’s lonely at the top for entrepreneurs and leaders. But it doesn’t have to be.


Six ways we unknowingly make bad decisions

On the topic of seeing your blind spots, the Harvard Business Review published a list of six of the top decision making traps for executives, and how to avoid them. These are good examples of the ways our unexamined minds, not the situations in which we find ourselves, can often be the culprit of bad decisions.

Check out “The Anchoring Trap,” from the article:

How would you answer these two questions?

Is the population of Turkey greater than 35 million?

What’s your best estimate of Turkey’s population?

If you’re like most people, the figure of 35 million cited in the first question (a figure we chose arbitrarily) influenced your answer to the second question. Over the years, we’ve posed those questions to many groups of people. In half the cases, we used 35 million in the first question; in the other half, we used 100 million. Without fail, the answers to the second question increase by many millions when the larger figure is used in the first question. 


The Waking Up app continues to expand my meditation practice

My meditation practice started with Headspace about 10 years ago, then evolved into studying Shikantaza (just sitting) under Abbot Sokuzan of the Sukokuji monastery. This type of choiceless awareness was incredibly helpful in processing the intense emotions of early 2020 in such a way that they flowed through me and completed rather than becoming stuck. But I now find myself broadening my practice to include more teachers, guided in large part by the frankly amazing breadth of content on the Waking Up app.

My first foray through a course on the app was Douglas Harding’s the Headless Way, which triggered some pretty dramatic experiences of consciousness for me and whetted my appetite for more. From there, I’ve started to dive into Loch Kelly’s Effortless Mindfulness content, and have found that to be a tremendous addition as well. Kelly experientially introduces the listener to what embodied consciousness (what he calls “heart consciousness”) feels like through structured “glimpses,” which I’ve found to be a quite useful, especially for those of us who spend a lot of time stuck in our heads (raises hand).

I don’t think it will replace my Shikantaza practice, but while I continue to go deep into choiceless awareness I’m also enjoying the breadth of learning from multiple teachers. I’m learning that breadth and depth complement one another in meditation.


A hopeful look at what 2021 might have in store, from a VC’s perspective

Your guess is as good as mine when it comes to what 2021 has in store for us. Laura and I stopped planning more than a month out in about May of last year. But even subject to inevitable wide swings, I like Fred Wilson’s take on what is coming in 2021:

  • COVID ends in the developed world in Q2, 2021

  • People mass socialize like their lives depend on it in H2, 2021

  • But we all still want to work/exercise/shop/etc from home

  • We will begin to address the economy and racial equity, but the climate crisis “will be to this century what the two world wars were to the previous one.” Also, “Climate will be to this decade what cloud was to the last one.”

  • Everyone migrates away from SF & NY to second tier cities (Grand Rapids is nice, I can vouch).

  • Government spending to deal with all this will open up a massive opportunity for crypto.

He says all these takes are obvious. But so was my trip to Machu Pichu in April, 2020, which has yet to be rescheduled. We’ll see.


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There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.

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