353. What I Got Wrong About Leadership

I didn’t learn the leadership lessons I teach because I was always good at them. I learned them because I was a lousy leader for a long time.

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I screwed up a lot of things throughout my career.
I still do.

If you’ve been reading this newsletter, you know that I tend to talk about leadership behaviors like they’re the easiest things in the world to do.

As if accountability, empowerment, and communication are just a matter of knowing the right framework and - poof - you’re perfect.

I talk as if I’ve lived a life of leadership perfection.

I haven’t.
Far from it.

Let me be straight-up with you:

I didn’t learn the leadership lessons I teach because I was always good at them.

I learned them because I was a lousy leader for a long time.

I started three companies and, miraculously, they each were acquired by public conglomerates. I worked as an executive leader at those companies until starting my next venture.

Sounds like I knew what I was doing, right?
Wrong.
Very wrong.

For most of my career I waged war against my Imposter Syndrome. It felt like I was leading wrong, but I didn’t know how to do it right.

I needed a mentor - a coach - someone who understood me. Someone who had been through the same things before.

I never found one, so I taught myself.

I built my own systems. I learned how to quiet those voices inside my head. And, eventually, I learned how to help others do the same.

That’s what I do now.

My goal is pretty simple:

I don’t want you to make the same mistakes I did.
I don’t want you to live with that same sense of disappointment for as long as I did.
I don’t want you to be the person I was.

I’ve already been that version of me.
I know how to avoid it.

⸻

Wisdom doesn’t come from doing things right the first time. It comes from doing it wrong enough times to finally notice there is a different door with a different solution.

What I’ve listed below are a whole bunch of things that I screwed up as a leader in my career.
Keep in mind, this isn’t the full list of my errors. It’s just a partial one.
Also, this isn’t meant to be a confession.
It’s just context for how I’ve learned how to avoid the pitfalls of poor leadership.

Here are some of the leadership behaviors that held me back:

⸻

I talked more than I listened.

I thought the more I talked, the more leader-like I appeared. I believed my job was to have strong opinions and convince others of their value. As it turns out, the more I talked, the more it shut down conversation until there was nothing left but silence.

I confused being right with being smart.

I could win the argument and still lose the room. It took me a long time to realize that being correct doesn’t create a committed team. It just creates compliance. And compliance never turns into motivation.

I didn’t hold people accountable and blamed them for the outcome.

I’d got frustrated when things didn’t meet my expectations… only to realize later those expectations mostly lived in my head. I assumed everybody knew what they had to do and when they needed to get it done. Then I punished people - sometimes subtly, sometimes overtly - for missing the target that was never actually defined.

I hired for skillset and ignored mindset.

I hired people who could do the work, but I ignored their ability to work well with others. I told myself their skillset mattered more than fit. I learned the hard way that culture is always more important than competence.

I avoided hard conversations and called it being “nice.”

I thought I was protecting relationships. What I was really doing was avoiding uncomfortable situations. Inevitably, the small issues would swell into big ones and derail my time and my company.

I didn’t delegate and convinced myself it was “efficency”.

I could do it faster. I could do it better. I used all the excuses to justify my controlling behavior. In the end, I just made myself the bottleneck.

I treated urgency like it was oxygen

Everything felt important. Everything felt immediate. I created constant pressure and didn’t realize how demoralizing it was for the people around me.

⸻

Most leadership mistakes are easy to justify. They don’t feel like mistakes until somebody tells you there’s a much better way.

I wasn’t malicious in what I did.
I wasn’t incompetent.
I was busy. I had nobody to guide me. And I was chasing a version of success that always felt just out of reach.

You may feel the same.

Leadership is nuanced. It’s in the words you utter while passing in the hall. In the tone of your Slack message. It’s in what you say - or don’t say - when everything inside you wants to stay quiet.

That’s how most of this works.

Leadership rarely breaks all at once. It erodes in small, subtle ways until you’re left wondering what the hell went wrong.

Why didn’t you get promoted?
Why did your best employees leave?
How come you keep missing your target goals?

What changed for me wasn’t some overnight transformation or sudden mastery.

I didn’t “fix” myself.
I just started becoming aware of the alarms and noticing them sooner.

I began paying attention to the moments where I felt defensive. Or rushed. Or unsure.

I learned to shut up when I felt the urge to be right. I learned to stop giving answers and start asking questions. I learned that sometimes a little discomfort is actually what is needed to create a comfortable culture.

I still screw these things up.
Just not as often.
And not without noticing it.

So here I am, committing to share with you not just what I learned, but how and why I learned it.

Because if it weren’t for those failures, we’d never succeed at all.

If this resonates with you and you want to talk with somebody who’s felt the same frustrations your feeling - and found the way out - let’s chat.

Why don’t we start by you letting me know what part of this message resonated with you.

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