Your solution is in your past

In 2018, right around our Series A, I hit a wall. On paper, things were going well. We had just raised money, we had a team, and we had momentum. Underneath, I was in the middle of some of the hardest co-founder tension I’d ever experienced. I remember thinking, with a clarity that surprised me, that something had to change. Either I had to step away, or I had to look at the one common factor in every frustrating meeting, and that was me. I was part of the problem. I was disengaging. I was stuck.

I’d spent years being good at the visible parts of the job: the product, the strategy, the pitch. What I hadn’t done was look at what I was bringing into the room with me. That’s where coaching started for me. My first sessions weren’t really about the business at all. They were about my patterns, how I show up under pressure, and what I do when things get hard.

You can only take your organization as far as you take yourself

I’ve said this line, “You can only take your organization as far as you take yourself,” enough times that it could sound like a cliché. It’s also in our book. It’s also the most consistently true thing I’ve learned in two decades of building companies and now coaching the people who build them.

The culture of a company is a reflection of its leaders, and that includes the parts of us we’d rather not look at. The conflict I avoid, you’ll find avoided across my team. The feedback I can’t give becomes the feedback no one gives. The fear I haven’t named quietly drives decisions I’d describe as strategic.

An organization can’t grow past the edge of its leader’s self-awareness. At some point, the work on the business becomes work on the person running it.

Shadow work, or what’s under the waterline

Shadow work is the name for looking at the parts of ourselves we’ve learned to push out of view: the reactions we’re embarrassed by, the stories we tell ourselves, the wounds that still steer us. In leadership, the shadow shows up as the same argument happening again with a different person, the feedback we are reluctant to share, or the decision we keep circling and can’t make.

For me, the place to start was the disengagement I mentioned earlier. I was frustrated by what was happening between me and my cofounder, and I was also actively pulling away. Looking at my own part meant asking a harder question: what do I do when things get difficult, and how does that affect the people trying to work with me?

It isn’t comfortable, and it isn’t meant to be. But what we leave in the dark doesn’t go away. It runs the show from behind the curtain.

“Your solution is in your past”

This is the idea from The Origin of a Leader that I keep coming back to. I used to believe that if I could just find the right framework or the right strategy, I could think my way out of whatever I was stuck in. What I’ve learned is that the thing I was wrestling with wasn’t new. It was an old pattern showing up in a new setting, and no amount of looking forward could resolve it until I looked back.

The patterns that make us hard to work with, or that keep us stuck, often have roots in earlier experiences. A particular way of operating may once have made sense, even kept us safe. Those same strategies, carried into adulthood and into the CEO seat, can become the very thing holding the company back.

That’s why I’ve come to believe that an origin story isn’t a branding exercise or a founder bio. It’s the map. If you want to understand why you lead the way you do, you have to go back and look.

One of the first things my coach asked me to do was list the pivotal moments of my life. Not the milestones on my LinkedIn, but the moments that shaped me. It was a business coaching intake form, and it asked me about my past before it asked a single question about my company. At the time that surprised me. Now it makes perfect sense.

Coaching, therapy, and the line between

I’ll be honest that this is an area where Mathias and I come at things a little differently, and we get into it in the episode. Coaching isn’t therapy. We spend most of our time in the present and looking forward, asking what you’re going to do about it. Mathias’s own coach once steered him away from digging into his childhood, and he’s the first to say that was the right call for him.

But I’d argue the two aren’t opposites. You don’t have to live in the past to learn from it. Understanding where a pattern came from gives you the choice to do something different with it. As Mathias put it, the more useful question is always, “Now that I know, what do I do with that?”

One question to sit with: where are you having the same frustrating experience with different people, and what might you be bringing into it?

Come listen

In our latest episode of The Intentional Organization podcast, Mathias and I pull back the curtain on what actually happens inside a coaching session. We talk about what brought each of us to coaching (for me, co-founder tension after the Series A, and for him, suddenly being the sole CEO with no idea what the job was), the awkward homework, rehearsing hard conversations, and the questions that have stuck with us for years.

If you’ve been wondering whether coaching is worth it, or if you’re sitting in a hard moment of your own, I hope it helps. Listen to Inside a Coaching Session.