My EA years taught me how to execute. The Chief of Staff seat taught me how to think strategically: to see the whole company, choose what matters, and turn a CEO's vision into a plan people can run. That's the bridge that got me to COO.
This week I've been writing about my path. On Monday, the gap between having the COO title and having the COO job. On Wednesday, how my years as an EA were really my operations training.
Today is the middle of the story, and in some ways the most important part.
As an EA, I was great at making things happen. As a Chief of Staff, I had to learn something different: deciding what should happen in the first place.
From doing the work to choosing the work
An EA's job is execution. The plan exists, and you make it run. You're measured on whether nothing gets dropped.
A Chief of Staff sits one level up. You're in the leadership meetings. You see every team's priorities at once, and you see where they collide. Suddenly the question isn't "how do we get this done?" It's "should we be doing this at all, and what matters more?"
That shift was uncomfortable at first. Execution has a clear finish line. Strategy doesn't. But it's where I learned to think like an operator.
Five strategic habits I built as Chief of Staff
1. Start with the why.
Before planning anything, ask what problem it actually solves. A lot of work exists because nobody stopped to ask. The Chief of Staff seat is one of the few places where asking "why are we doing this?" is part of the job.
2. Pick the few things.
Every company has more good ideas than it can run. I learned to help the CEO choose three priorities instead of ten, and to protect them. Saying no to good work so the important work gets done is strategy in its simplest form.
3. Connect the dots across teams.
From the Chief of Staff seat you see how a decision in one team lands in another. Sales promises something, delivery has to build it, finance has to fund it. Learning to see those ripple effects before they happen is what separates a plan from a strategy.
4. Turn vision into a rhythm.
CEOs think in big ideas. Teams need owners, dates and a weekly cadence. A big part of my job was translating one into the other: the leadership meeting, the priorities list, the follow-up. A vision nobody can run isn't a strategy yet.
5. Think a quarter ahead.
Day to day, it's easy to live in this week. The Chief of Staff seat taught me to look one quarter out: what's coming, what will break, what needs to start now so it's ready then.
How it carried into the COO seat
When I became a COO, the strategic habits came with me. What changed was that I could act on them in my own name.
As a Chief of Staff, I could see what mattered and help the CEO decide. As a COO, I could decide, build the plan and own the result. The EA years gave me execution. The Chief of Staff years gave me strategy. The COO seat is where the two come together.
And it's a muscle I'm using more than ever now. When AI can take on a whole category of work, you can't just ask how to do the same thing faster. You have to step back and ask what you'd do differently. That's a Chief of Staff question, and every operator is being asked it right now.
If you're a Chief of Staff right now
The strategic part of your job is the part that will carry you furthest. Protect it. If your days fill up with coordination and follow-up, block time every week to step back and ask the bigger questions: what matters most this quarter, what's stuck, and what should we stop doing.
If you're a founder
Give your Chief of Staff a real seat in strategy, not just in the follow-up. Bring them in while the decisions are being shaped. They see the whole company from a place nobody else does, and that view is worth the most before the decision, not after.
The bridge
I didn't go straight from executing to owning. I needed the years in between, learning to see the whole board.
If you're a founder who needs someone to turn your vision into a plan your team can run, let's talk.
