For most of my corporate career, if an executive had a major speaking engagement in another country, someone from communications was getting on the plane. Often, that someone was me.

So when I moved to a startup and our CEO was invited to deliver a main-stage keynote in Paris, every instinct I’d built over more than a decade inside a Fortune 500 company told me what came next. Except this time, I didn’t get on the plane.

I worked closely on the narrative, the talk track, the slides, and coordinated with the conference team, right down to making sure his notes would appear on a downstage monitor. Then I sent him to Paris without me.

The talk was one of the strongest I’ve seen him deliver. Two years later, our team still references it and shares it with customers.

And that downstage monitor I’d carefully planned for? It wasn’t there. Something had gotten lost in translation. Fortunately, he didn’t need it.

That moment captured something I’ve been learning as a leader: Becoming better can mean unlearning what doing the job well looked like.

The fundamentals I built over my career—storytelling, judgment, creativity, customer understanding, and trust—matter even more now. But some of the scaffolding around those fundamentals was built for another era. Here’s what I unlearned since.

A startup gives you a blank canvas. That sounds freeing, until a major launch, when you notice every role that doesn’t exist. The instinct is to fill the boxes.

But I keep asking myself: If we were inventing this workflow today, would we build it the same way?

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