Five Things I Learned in My First Year as Chief of Staff

Nothing, truly nothing, gives me more joy than crossing tasks off a to-do list. I’ve excelled at this my entire career. From simple tasks like sending emails to giant initiatives that require multi-phase implementation, I’ve honed execution and operationalization into a superpower.

For my first three years at Ascend.io, a startup building an agentic data engineering platform, I wore a lot of hats: people operations, marketing, sales, customer success, and sometimes, even product. Not sequentially. Simultaneously. I was building the team culture and the outbound pipeline in the same week, writing the onboarding program and the campaign brief in the same afternoon. That breadth was its own education, and I’m grateful for every chaotic, overextended minute of it.

But when I stepped into the Chief of Staff role, something shifted. There were parts of the job I’d been doing for years without the title. And there were parts I hadn’t touched — finding a voice in our leadership team, being a real participant in strategic conversations, holding the thread between where we were and where we were trying to go. The title changed, and then, gradually, so did I.

A year in, here’s what I’ve learned.

1. I didn’t just use AI this year. I learned to lead it.

I was already using AI before I became a Chief of Staff. Coming from the nonprofit world, I’ve always had to stretch every resource as far as it will go. Leveraging tools that let me do more with less is a deeply held value of mine. What changed this year was how I related to them.

Somewhere in the middle of planning a two-day virtual bootcamp for thousands of registrants, building an outbound pipeline from scratch, producing technical content, running a company-wide hackathon, and handling the scope of employee experience — I stopped thinking of AI as a tool I was operating and started thinking of it as a team I was leading.

That reframe changed everything. When you manage an agentic system the way you’d manage a team (with clear context sharing, defined roles, a feedback loop, and explicit expectations), the output is different. Better. More useful. And the “relationship” becomes something you can actually build on. The project the system collaborates on develops a deeper understanding of patterns that work and documents paths to success that exponentially improve results over time.

I’m not claiming AI replaced human collaboration or that it’s without limits. But I will say this: for the first time in my career, I felt like the ceiling on what I could accomplish wasn’t set by how many people were on my team.

2. The to-do list is a trap.

I hate to admit it. But it’s true for me.

I am, at my core, an achiever. I have been since I was a kid doing ballet and soccer and choir and reading thirty books over the summer between second and third grade. Checking things off feels good. It has always felt good. And in most operational roles, being someone who gets things done is the whole job.

But the Chief of Staff role asked something different of me, and it took me longer than I’d like to admit to hear the ask.

The immediate gratification of clearing a to-do list can become its own form of avoidance. When you’re moving fast and producing a lot, it’s easy to tell yourself you’re being effective — and miss the fact that you’re not spending nearly enough time asking where are we actually going and is this the best path to get there?

Creating space to think - not just about what needs to happen this week, but about direction, long-term trajectory, and whether the strategy underneath the tactics is sound - is harder than it sounds when your inbox is full, your calendar is packed, and you’re on your sixth Diet Coke of the day. But it is the work. The rest is just logistics.

I had to build that muscle deliberately. I still have to protect that space like it’s sacred, because it is.

3. I said yes to everything. I’d do it again.

In the past year, I have executed two two-day developer bootcamps, built a dozen data pipelines from scratch, written seven technical blog posts, designed 15 live hands-on workshops and webinars, collaborated with countless partners and customers, experimented with 20+ AI SDR outbound sequences, produced four company hackathons and three in-person offsites, managed speaker logistics across tens of events, built pricing calculators, and developed sales pitches. Among other things.

Most of them I had never done before. And many I wasn’t really sure how to get started on.

I said yes anyway. Every time.

Here’s what I learned: breadth is how you build range. Every time I said yes to something I had never done, I either discovered I was capable of more than I thought — or I discovered exactly where my edges are, which is equally valuable. Either way, I came out of it more confident than I went in.

Is it always sustainable? No. There were weeks (or months) this year that were genuinely WAY too much. But the accumulated confidence of having figured out hard things I’d never tried before is not something I would trade. It compounds. The things I accomplished because I was willing to try gave me more and more capacity to attempt bigger and harder things.

If you’re early in your career and you’re wondering whether to raise your hand for the thing outside your lane, definitely raise your hand. I have never regretted it.

4. Strategy requires curiosity, not answers.

I used to think being strategic meant having the right framework, the right analysis, the right answer ready to present. I was wrong about that.

The most strategically valuable thing I did this year was ask questions — often questions that felt almost too basic to ask out loud. Why are we doing it this way? What problem are we actually solving? Who is this for, and do they know it exists? What would we do if this didn’t work?

Good questions create more forward motion than confident answers. They surface assumptions. They reveal the places where a team has quietly gotten out of alignment. They invite the kind of thinking that produces something genuinely better than what was already on the table.

I don’t think I’m naturally patient enough to sit in questions — I want to move, to solve, to cross things off (see lesson two). But I’ve learned that the pause before the answer is often where the actual strategy lives.

Curiosity is not a soft skill. It is the work.

5. Ambiguity is either fog or open road.

The Chief of Staff role is, at its core, a role you define as you go. There is no universal playbook, no standard org chart position, no agreed-upon set of KPIs that tells you whether you’re doing it right. What the role means depends entirely on the company, the CEO, and the moment you’re in.

That ambiguity can feel like fog — disorienting, isolating, impossible to navigate. Or it can feel like open road.

What I’ve learned is that the difference isn’t the ambiguity itself. It’s what you do with it.

The job of a Chief of Staff is to create clarity — not just for yourself, but for everyone around you. To take the swirling mass of competing priorities, half-formed strategies, and unspoken tensions and turn them into something the team can actually move toward. When you do that well, clarity becomes momentum. People move faster. Decisions get easier. The whole organization benefits from having someone who is willing to name the thing nobody has named yet and build the structure that lets everyone else get on with their work.

That is not a support function. That is leadership.

I am still learning what that looks like at every new stage of growth. I suspect I will be for a while. But I’ve stopped waiting for someone to hand me the map. The terrain keeps changing anyway.