The Myth of the Great CEO

I’m a coach to CEOs and leaders to support them on their journey back to aliveness. Last week a client of mine asked what she could do to be a better CEO or leader. And whether I had any tips for her or things she could do. She heard that the best leaders and CEOs get up early and are really focused on self-care and on the business.

I paused, looked at her mischievously and said that I think that’s entirely the wrong question. And that on top of that, I think that there is no such thing as a great CEO or leader. The only thing that does exist in my experience is a powerful and alive human that loves what they are doing and that happens to run a business. And then other people look at them and say “this person is a great CEO!”. Unfortunately, often we get it all twisted and turned upside down when we try to start at that label and reverse engineer from there.

Whenever we start at the conceptual description of a role, it’s a dead end. Whether you try to be a great CEO, a great mother, father, girlfriend, employee, marketing manager or what have you. Even if we succeed, it always leads to disappointment and resentment. That is because when we try to fit into a pre-conceived role, we make ourselves fit into something that is just a mental concept, like that of a CEO. It has little to do with who we are as powerful humans.

Instead, I exclusively coach around bringing every conversation back to the human level. Meaning to ask in different shapes and forms: What makes you come alive? How do you feel powerful and playful? This is where greatness in hindsight comes from.

So instead of asking yourself “What makes a great leader?” or “What makes a great CEO?”, I want to give you 3 better questions for greatness in hindsight and aliveness today:

What’s stopping you from doing what’s right in front of you?

We can get lost in hypotheticals of “what makes a great leader!” easily, but often, that’s just an excuse for focusing on what’s right in front of you. If you take a second to pause at this moment, I’m sure there’s something right there, right in front of you that you’d love to do. But! That you’re also scared of. And maybe it’s a completely simple and obvious thing – in fact, it often is. Here’s a list of things I’ve heard about from CEOs just in the last couple of weeks of coaching sessions:

• Have an honest conversation with a director in the company
• Buy a piece of equipment for the factory
• Take a week of vacation
• Start writing a book
• Let yourself feel dejected

These are not big things. But each of these things, if repeated daily and with attention, is what will turn into greatness over time and have other people say “this person is a great leader!”. But even more importantly, it is what makes us feel alive and excited and we get to work with the simple, scary, obvious thing right in front of us. And I’m much more interested in aliveness than in greatness. 

What are you feeling most unsure and insecure about?

I had a client who was the CEO of a popular tech platform. He was an engineer by trade, yet almost every session he told me that the biggest opportunity he saw for his business was to focus more on marketing and sales. And yet, most of the actions he took were focused on building yet better tech and AI features for the business.

When I pointed that out, he vulnerably confessed that he feels so safe and savvy when it came to engineering, yet so stupid and inexperienced when it came to marketing and sales. To me, that was a massive success, since when we find where our insecurity lies, and we allow ourselves to explore it, that’s when we truly uncover our potential for growth and the next steps. The area where we feel masterful already is often one where we’ve explored much of our potential also.

The places in your life that you are drawn to, but feel timid, insecure, and unsure about are often the ones where the most growth waits for us.

Which parts of your life do you feel most insecure about, that you put off often, but also know that it’s something you deeply value? Then begin with giving those parts a tiny bit more oxygen and attention and see what next steps naturally unfold.

Who do you care most about?

A bit over 10 years ago, I was a startup founder standing on top of a hill in San Francisco, 20 years old, fresh off the plane from Europe, wide-eyed and excited for my upcoming adventure. Over the following 6 or so years, I went down the rabbit hole of startup life. I faced the deep struggle of startup fundraising that almost put me out on the street homeless. I had to leave the US because of Visa troubles, traveled around the world, had to fire a co-founder, and through all the ups and downs eventually managed to build a business that’s doing north of $20m in revenue today.

When people ask me, what is the one thing I regret not having on my startup journey, I say this: I wish I had a coach. A trusted, grounded, emotionally intuitive person who knows what he’s talking about and has experienced what I have. I often felt deeply alone, miserable, burnt out, elated, excited and so much more. Yet, I wished I’d had a safe place to bring all this to.

On my journey since building that business, eventually moving to live in a Buddhist monastery for close to two years, training as a trauma therapist to learn the skills of deep emotional presencing, I made that my calling. To be that person to the startup founders, leaders, CEOs and creators of the world. To support them and be their coach as they go through life. Nothing has been more fulfilling for me than this. And when I’m in a rut where I wonder “How can I be a great coach?”, I know that that’s not the right question. And instead, a better one I like is to think about how can I support the people I care most about more or better. This is where I see action, potential, fun and excitement.

I’m guessing that the same is true for you. With the business you’re in or the life you have, what are the kinds of people you care about the most and that you want to support? 

This question can bring us into the here and now very quickly: People that are cold in the wintertime? Children dying of cancer? Leaders that want more confidence? Men that want to have more empathy? When you take out a piece of paper and write that question at the top, you might be surprised by what kinds of answers you come up with. And you might also be surprised at how quickly you have an idea of what to do next, now that you wrote that down. 

What is your next, one, tiny step?

I get sucked into attaching myself to big ideas without ever making progress, just like the next person. I’ve been renting the apartment I’m living in for over a year. Although I always thought of this as the most amazing place to ever live in, I barely furnished it in that time. One thing I’ve been dreaming about was to have lots and lots of plants. And yet nothing happened. Then a friend of mine gifted me a plant the size of a drinking cup, I’ve posted a picture of it below.

And from there, suddenly and magically, I felt empowered and encouraged to take more tiny steps, like that one tiny plant to furnish my apartment. Although I have a long way to go, it already feels much more homey and comfortable than before.

It can feel ridiculous to think about taking tiny steps when you’re already a big-shot CEO or when you’re wanting to become one, one day. And yet, I know no better tool at times than to take a step so ridiculously small in the direction that you want to go and to see what happens next. Usually, all the other steps flow from there.

With the big dream you have in front of you, what’s one tiny step, that’s almost ridiculous, that you can take today?

Takeaways

These questions and stories above are designed to help you do one thing only: to move from the hypothetical, abstract and unhelpfully analytical into the concrete, the here and now. This is where your power lies in my experience. And it is when true change and transformation can begin.

At the root of it all to me is the question: How can I come alive as a human and live into my truth? 

If you really do want to play it big, focus on that last question more than anything, and naturally, all greatness you ever longed for, as a CEO or otherwise leader and human will naturally follow. There are no great CEOs, only people that have come alive.