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It’s Issue 1️⃣ 0️⃣ 0️⃣. The version of me who hit publish on Issue 1️⃣ wouldn’t recognize half of what I think now. And honestly that feels like the right thing to write about.

So instead of a milestone roundup, here’s a letter about what I got wrong, what’s changed, and what I believe now after almost 4️⃣ years and hundreds of conversations with Chiefs of Staff.

I assumed Chiefs of Staff would show up for the tactics 📋

Templates, frameworks, the board prep example you could steal on Monday. That’s how I described the role to myself when I was doing it, so I built for the version of me who wanted ROI by Friday.

What actually pulled people in was belonging 👩🏾‍🤝‍👨🏼

The most common reaction I get from members isn’t “I learned something new.” It’s “I didn’t know other people felt this way.” The tactical stuff is the doorway. The reason they stay is that this is the first room they’ve been in where everyone gets it without explanation.

I should have seen this coming. The role itself is structurally lonely. You sit between layers, you hold information you can’t share inside your own company, and your peers are scattered across orgs that have no idea what you actually do.

Of course the answer is other Chiefs of Staff. I just thought the answer would look more like a course.

I started a newsletter expecting to teach. I ended up building a mirror 🪞

There are also a few things I believed that weren’t necessarily wrong, but that have definitely evolved after working with so many Chiefs of Staff over the years.

🧑‍💼 Leadership rooms aren’t where answers get handed down. I used to think being a Chief of Staff meant getting a backstage pass to certainty. The first time I sat in those rooms and watched smart people argue their way through gray areas with incomplete data, it reframed the job for me. The Chief of Staff isn’t there to transcribe the answer. The Chief of Staff is part of how the answer gets made.

👣 The “18–24 month stepping stone” framing isn’t right. I bought it when I started writing. I don’t anymore. I’ve watched too many people build careers as a Chief of Staff—staying with a Principal for years, moving CoS-to-CoS, becoming the operator a company can’t function without. It’s a path, not a launchpad.

🤖 You can’t be a great Chief of Staff in 2️⃣ 0️⃣ 2️⃣ 6️⃣ without being fluent in AI. When I was in seat at Hugging Face, AI literacy wasn’t on any job description, despite the company itself being AI native. Now it’s on almost all of them. The Chief of Staff is becoming the person who decides what gets automated, what stays human, and how the org adapts to both.

The turning point that crystallized everything was our first NYC Summit 🍎

5️⃣ 0️⃣ Chiefs of Staff in one room, no screens between them. I’d been telling people for years that peer-to-peer was where the real value lived. Watching it happen in person was the first time I fully believed my own pitch ✨

Every once in a while a member says it back to me in a way that makes it land harder than I ever could. Gina Ruscio dropped this in our wins channel after signing her Chief of Staff offer at a Series A:

“I found this opportunity through the Ask a Chief of Staff job postings and tailored my resume with the peer resume review workshop — this is easily the fastest value I have ever seen in a professional network.”

That’s the thing. The community isn’t a place to learn the role. It’s the shortest path between a Chief of Staff and the next chapter of their career.

After 1️⃣ 0️⃣ 0️⃣ issues, hundreds of conversations, and 4️⃣ 0️⃣➕ placements, Ask a Chief of Staff isn’t just a community anymore. It’s an aggregation of what hundreds of Chiefs of Staff have figured out the hard way. Newer members get to inherit that.

That compounding effect is the thing I didn’t see coming, and the thing I most want to protect 🫂

Curious to see what’s behind the curtain? 👀

Our Ask a Chief of Staff paid community is now open for a 3️⃣ 0️⃣-day free trial. Full Slack access, workshops, mentors, the works. I built this room for exactly the Chief of Staff reading this email because I know this role can be isolating. But it doesn’t have to be. Come see for yourself if these are your people 👇

Start Your Free Trial

From the outside, Ask a Chief of Staff looks like a newsletter, a community, and a recruiting arm. From the inside, it’s a small team running a tight ship: monthly reporting, an onboarding sequence built to reduce 90-day attrition, an event cadence we don’t break. Most of that is invisible because it works.

I learned to run an org as a Chief of Staff, and I built this one without the operational debt I’ve watched other founders dig out of. That part isn’t glamorous, but it’s the part that lets everything else compound.

The loneliness is the hardest part, honestly. I often refer to the Chief of Staff role as an island of one 🏝️

I built a community for Chiefs of Staff specifically because the role is isolating, and then I underestimated how isolating founding would be. Different shape, same problem. You hold the whole picture, you make calls with incomplete data, you can’t fully offload it to anyone. It’s the same job I left, just from a different chair.

The other hard part is the lack of a playbook. I assumed my Chief of Staff toolkit (operating cadences, decision frameworks, prioritization) would mostly carry over. It does, up to a point. Running a business means making a hundred small decisions a week with no senior person to escalate to. There’s no “right” version of this, and I’m still getting used to that.

⚠️ The part nobody warned me about: when Ask a Chief of Staff is going well, it’s invisible. When something cracks, it lands on me. That’s the Chief of Staff dynamic, too. I accidentally built a business with the exact emotional weight of the role it’s for.

I’ve talked to hundreds of Chiefs of Staff and gained an enormous amount of perspective that I simply didn’t have when I started. Here’s the short version of what I wish someone had told me before I took the role:

1️⃣ The job is whatever your Principal needs it to be. And that will change. There’s no one-size-fits-all description. Some days you’re running board prep. Some days you’re resolving team conflict. Some days you’re reworking the hiring plan. Your calendar is a reflection of their chaos. Expect it.

2️⃣ The job will break you if you don’t set boundaries. You’ll be pulled into everything. That doesn’t mean you need to own everything. Clarify your role early. Be honest about your capacity. Otherwise you become a dumping ground for “miscellaneous leadership tasks.”

3️⃣ You’ll question your impact. Often. This is a behind-the-scenes role. You’re rarely the decision-maker. You don’t always get credit. You are the glue, the amplifier, the friction remover. It matters even when it’s invisible.

4️⃣ This role runs on emotional range. It’s 30% strategic thinking, 70% relationship management. If you can’t handle egos, resolve tension, and build trust across functions, the strategy won’t land.

5️⃣ Your Principal is figuring it out, too. Even if they’ve been a CEO for 10 years, they’re still carrying doubt. Still making bets. Still human. The sooner you realize you’re both figuring it out together, the more effective (and connected) you’ll be.

6️⃣ Find other Chiefs of Staff. This job is too ambiguous, too emotionally intense, and too high-stakes to navigate solo. Whether it’s a community, a mentor, or a DM group, find your people.

7️⃣ Write stuff down and document everything. The operating cadence. The decision criteria. The takeaways from that “quick sync.” It doesn’t need to be fancy. If you’re the memory of the org, make sure you have one.

BONUS: I tapped community members to weigh in on this exact theme earlier this year. If you missed that issue about what 🔟 Chiefs of Staff would tell their former selves, check it out here.

You may have already noticed this in the first half of 2️⃣ 0️⃣ 2️⃣ 6️⃣ , but I’m committed to hosting even more in-person events and AI programming to better support our community.

Ask a Chief of Staff started as a Slack community and a newsletter. Our NYC Summit earlier this year convinced me the highest-leverage version of this is in person.

🏙 We’re heading to Boston, Miami, San Francisco, and beyond this year, with more cities on the runway. If you’re a Chief of Staff in one of those cities, please join us. I’d love to meet you! 💜

🤖 The other thing is AI. The role is changing faster than any other I write about, and I want Ask a Chief of Staff to be the place where Chiefs of Staff figure out what it means to operate as a “Chief of Agents.” That shows up in workshops, content, and maybe an industry survey later this year.

If you’re new here, or if you’ve been reading for a while but never said hi: you’re not making it up. The role really is this strange, this ambiguous, this lonely, but also this important.

The single thing I want you to take from this letter is the same thing this community has given me: a room full of people who get it without explanation. Find them. By DM, by mentor, by community, by whatever channel works for you. Don’t do this job alone. It’s not built for that.

Thank you for being here for 1️⃣ 0️⃣ 0️⃣ issues! For replying to my emails. For showing up to workshops at 7am your time. For trusting me with the questions you can’t post on LinkedIn. Ask a Chief of Staff doesn’t exist without you, and I mean that literally.

Here’s to 1️⃣ 0️⃣ 0️⃣ more! 💜

Clara

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