That’s certainly how I felt when I stepped into Corporate America. 

I wasn’t fresh out of college when I got my “corporate job,” in fact, I'd spent four years ironworking (construction) while writing and acting on the side. My "desk job" was supposed to be my way out.  

But I was signing away more than I realized.

And pretty quickly, I hated it. 

Director was supposed to be awesome. Delegation. Responsibility. Power. In reality, I felt like a pressed panini. 

The skills that got you promoted are not the skills that make you good at the job.

I got promoted because I was a strong individual contributor. I could write. I could execute. I could deliver under pressure.

But leadership required a completely different toolkit:

It took failing (hard), to realize I needed to change.

One of my reports—someone I'd come up with as a BDR—requested a one-on-one. And honestly, we'd been butting heads.

He was a volume workhorse. He LOVED cold calls. He’d spend 8 hours a day dialing if he could. I usually took a more personalized strategic approach. I was more like a prospecting sniper. 

So naturally, we had completely different ideas for how things needed to be accomplished. Since I had gotten promoted, I thought my ideas were obviously the best. I mean, they worked for me, right? Shouldn’t he just trust me? Trust the process?

In the one-on-one he expressed that he felt like he was taking steps backwards since I became the leader. He felt like I didn’t really see him and his talents.

And he was right. I was so focused on what worked for me when I was in his role, I didn’t stop and think about what made him extraordinary. I didn’t create a structure that centered his “X-factor.”

Leadership is not a quality, it's a skillset. And like any other, it needs to be learned.

It's why bad leaders are so bad. They don't just affect their own work—they affect everyone around them. Bad leaders create bad teams. Bad teams create bad products. Bad products create bad companies.

And like me when I stepped into my first leadership role: a lot of times bad leaders were once amazing individual contributors.

But when they faced the music, they stopped growing. They doubled down on bad habits and old ways. Instead of expanding their skillset, they relied on their old tricks.

I almost became one of them.

Tough words for me to say then, but now they’re some of my favorites. I told my colleague (who was probably on his wits end with me) this. By starting with acknowledging that, we forged a real partnership.

I reshaped our strategy around what he did well. And suddenly… we were surpassing our numbers. He was actually doing better than I did when I was in his role.

To this day, he’s one of my favorite colleagues I ever had. We still talk all the time. And there’s still a piece of me that feels so stupid I didn’t wake up and try and grow sooner. 

I see this pattern constantly now as a consultant. Founders who are brilliant strategists but can't delegate. Directors who are incredible executors but can't coach. VPs who can sell a vision but can't have a hard conversation.

And frankly, I have a lot of empathy for them. Leadership feels like the mama bird pushing the baby out of the nest. Hopefully they learn to start flapping their wings and if not…

Splat. 

“I’m slowly learning to delegate tasks to other team members. I’m learning to have a lot of trust in people and try to empower others. And I’m hearing more appreciation and openness from team members.”

It’s vulnerable being in a learning mindset. Change is painful, especially when you’ve been rewarded for who you were, even if it’s not serving who you are now. 

The climb isn't the problem. It's climbing without learning new skills along the way. 

Every week, we share lessons like this—stories from the trenches of leadership, the mistakes we made, and the frameworks that actually work. For founders, new leaders, and anyone who realizes being good at your job doesn't automatically make you good at leading others.

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