ARTICLE
People often ask how I became a Chief of Staff and then a COO, as if there were a map. There wasn't. I earned certifications for a career I never took, almost settled into a role I'd outgrown, and needed someone to push me over the ledge. Here's what that taught me about how careers in operations actually work.
Someone asked me recently how I got into the Chief of Staff and COO seat. What were my first steps? How did I get my foot in the door?
It's a fair question, and I think people expect a clean answer. Step one, step two, step three.
My honest answer is that it was never a plan.
Where I actually started
I started as an executive assistant. A high-level one, and I was good at it. I was also restless. I wanted more scope, more ownership, more of a say in how the work got done, not just how it got scheduled.
For years I tried to move into bigger roles and kept bumping into the same wall. People saw the EA title before they saw the work. Eventually I almost made peace with it. I had nearly decided I was a career EA.
The path I was sure about
Somewhere in there, I was certain I'd figured out my next step. I earned a project management certification. Then a product management certification. I was going to be a project manager, or move into product. It made sense on paper. I was already managing timelines, stakeholders and deliverables every day.
And where did I end up? Chief of Staff. Then COO.
I don't regret those certifications for a second. Everything I learned in them shows up in my work today. But they taught me something I didn't expect: the step that looks obvious from where you're standing often isn't the one you take.
The push
What changed my path was a mentor.
He introduced me into my next role with one condition. I couldn't take it as an EA. If I was going to do the job, it had to be a leadership role. So I stepped in as Chief of Staff.
I wouldn't have done that on my own. I needed someone to push me over the ledge.
A few years later I realized that to get done what the company needed, I had to stop borrowing my authority and start carrying my own. That's when the title became COO. The work barely changed. The way I walked into a room did.
Operations opens more doors than people think
Here's what I wish someone had told me earlier.
When you're in an operational role, it's easy to assume the next step is obvious. EA to Chief of Staff. Operations manager to director. One rung at a time.
But operations is one of the most flexible foundations there is. The people I know who started where I did have gone in every direction: Chief of Staff, COO, program management, product operations, people operations, compliance, business operations, fractional work, and even founding their own companies.
That's the great thing about operations. You learn how a business actually runs, and that knowledge travels.
What I'd tell anyone trying to find their path
1. Find mentors who matter.
Not just people who cheer you on. Find the ones who get it and can walk you through your options objectively. Sometimes people chase a role that just isn't the right fit, and a good mentor will tell you that before you spend two years finding out.
2. Don't assume the next step is the obvious one.
It's easy to think Chief of Staff is the natural next step from EA, or that project management is the natural next step from coordinating projects. Sometimes it is. Often there are several good paths, and the right one depends on what you love doing, not just what you're already doing.
3. Raise your hand for the messy work nobody owns.
The cross-functional project that touches every team. The process nobody wants to fix. That's where operations leaders get built, and it's where people start to see you differently.
4. Let your learning count, even if the path changes.
My certifications didn't lead where I expected, but they made me better at the job I have. Nothing you learn is wasted. It just shows up somewhere different.
5. Let someone push you.
If someone you trust tells you you're ready for more, believe them. I almost didn't.
6. Network, especially online.
Talking about my work publicly has opened more doors than I ever expected. The way things are going, the conversations you have online matter more than ever.
The path is yours
I didn't plan my way into the COO seat. I grew into it, one turn at a time, with a lot of help along the way.
If you're somewhere in the middle of your own path and it doesn't look like the map you expected, that's not a problem. That might be the point.
If you're a founder looking for an operator who's run the function from the ground up, let's talk.
