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.
4 THINGS I HAD TO UNLEARN
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.
1. Don’t rebuild the organization you left.
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?
Increasingly, the answer is no.
I spent years building specialized expertise: shaping executive narratives, building thought-leadership platforms, and preparing leaders for high-stakes moments. At a startup, I’m experimenting with capturing that context in how we work, so others can use and adapt it.
The goal is to help expertise travel.
2. Don’t just make the old job faster. Redesign it.
Using AI to speed up one task is useful, but I’m more interested in what happens when teams start reimagining the work itself.
The questions I return to are simple. What context can we teach the system? Where is human judgment most important? How can someone use expertise that once lived in another person’s head?
I have a marketing team member who wanted to grow into communications. I started mentoring her on preparing executives for podcasts and speaking opportunities, and on building their social platforms. Instead of just teaching the skills, I shared how I train our brand and executive voices, so she could adapt them herself.
She went from learning to mapping out a full thought-leadership campaign on her own. After launch, an executive raved about her partnership. Soon she was building platforms for two more leaders, and bringing me ideas she’d dreamed up.
Democratizing expertise creates more builders. I’m learning to coach differently, giving others the context, tools, and confidence to build on what I know.
AI’s bigger opening is helping more people benefit from what each of us knows.
3. Speed is how fast you get it right.
Startup culture prizes speed. AI has sharpened that. Everyone expects instant answers. Recently I tested an AI workflow where the output took a few minutes. “It’s thinking,” the team said. The result was much closer to what I wanted than the usual instant response. I’d rather wait a few minutes than spend an hour prompting and rewriting.
The goal is getting it right, faster. And getting it right still requires people. That’s worth sitting with, because the pressure pulls the other way. When our team at Typeface surveyed 500+ marketing leaders, 62% admitted they’re already trading away quality, and 61% said the same about authenticity, to get cited by AI. Everyone is racing to be found. The first things to slip are the human signals that made a brand worth finding.
Being found is only the beginning. The advantage goes to brands that stay unmistakably themselves, whether they’re engaging a person or an AI agent. Human creativity is the differentiator that can’t be copied.
4. Being a strong leader doesn’t mean being in every room.
Back to Paris. I’d done the work, built the narrative, run the prep, developed the relationship. Something still went wrong, and the CEO was great.
My job was to help make sure he didn’t need me. I think about this with my team now. Sometimes an opportunity I would have owned before is better given to someone else. Sometimes expertise is more valuable when you teach it, or build it into a workflow others can use.
Scaling yourself is about creating impact in rooms you’re not in.
EXPERIENCE SHOULD GIVE YOU CONFIDENCE AND CURIOSITY
I left a Fortune 500 company for a startup expecting to be scrappy. Instead, I started questioning what we build with.
The way we work can be one thing. Context is another. The expertise of one person, captured and shared well, can serve many.
Maybe the most important one is our willingness to learn. AI is changing fast enough that none of us gets to be an expert forever. Our careers have given us judgment, pattern recognition, relationships, storytelling, and the ability to recognize great work. We also need a beginner’s mind to question the systems we’ve built around those skills.
Going first doesn’t mean adopting every new tool or discarding everything that came before. It means being willing to put your own assumptions on the table. Experience can be knowing what you’re willing to leave behind.
Courtney Brigham is senior director for communications and brand at Typeface.