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What I Wish I Knew Before Becoming Chief of Staff
Everything I wish someone told me before I became Chief of Staff.
Hi! Welcome to another issue of Force Multipliers, your weekly briefing from Regina Gerbeaux, where Silicon Valley's behind-the-scenes operators get battle-tested frameworks for their toughest challenges, from putting out chaotic fires to managing strong personalities.
Dear Regina,
Is there anything you wish you had known when you started your first Chief of Staff role?
I’m just stepping into mine, and already learning that I default to working around others instead of pushing back and advocating for the right outcomes - especially when I’m trying to build something from scratch. I also got great advice recently to track my work and reflect on what I enjoy (or don’t), but I’d love to hear your personal take.
What are the common pitfalls? Anything you’d go back and do differently?
- CoS, working in a small B2B SaaS startup
Dear Operator,
There are a lot of ways to learn in a CoS role - but the most expensive way is learning everything in hindsight.
Let me spare you. If I could go back and give myself a debrief before I stepped into my first Chief of Staff role, here’s everything I would say…
The Basics of Being a Chief of Staff
Step 1: Get crystal clear on your Zone of Genius 💡
I know this phrase gets tossed around a lot, but I want you to actually sit with it. Your Zone of Genius isn’t just what you’re good at. It’s what you’re great at AND energized by.
Over the years, here’s what I’ve seen most high-achievers miss:
👉 They over-rotate on excellence. They say yes to all the things they’re great at - even if those things drain them. Why? Because they’ve been rewarded for it. Because people keep asking. And they technically can do it, so why not do it?
Slowly, they build careers around being the best cleanup crew a company could ask for.
But that doesn’t lead to growth - it leads to exhaustion and a whole ton of resentment.
Your first job in this role isn’t to be everything to everyone. It’s to do a full inventory of:
What gives you energy vs. what burns you out
What you would choose to master, even if no one was watching
What feels like flow, rather than just function
This will help you decide where to double down and where to start saying no. It will shape the kind of projects you lead, the kind of leaders you align with, and ultimately, the kind of roles that open up for you.
If you’re not careful, your Zone of Excellence will seduce you into staying average at things you’re too tired to care about.
When you distract yourself with other busywork, you never give your body and brain time to recognize that it is, in fact, not in any physical danger (and, as a result, does not have to have the reactive brain working overtime.)
This is why I recommend spending time simply feeling your emotions, without judging them. One of my favorite meditation teachers, Jeff Warren, calls this equanimity. It means observing without judging, or trying to change it.
🤎 ACTION:
Journal and name your Zone of Genius, and Zone of Excellence. Talk to your manager about it. Start architecting your role around it - not the other way around.
Step 2: Have a North Star - even if it’s a blurry one ⭐️
You don’t need a 10-year plan. But you do need a compass.
When I started as Chief of Staff, I treated it like an open field: a place to try everything, get exposure, and build range. And that was fine for a while.
But eventually, a lack of direction became a liability. I didn’t know which projects to prioritize. I couldn’t clearly advocate for my growth. And I definitely didn’t know what I wanted my next job to be.
If you don’t have a North Star, you end up playing support roles in other people’s stories, while your own story goes undeveloped.
Here’s what I recommend:
Ask yourself: “What would I want my role to look like in 2 years?” Not title - work. What would I be building? Leading? Solving?
Choose a functional direction. (Finance? People? Strategy?) You can always pivot. But you need something to pattern-match against.
Start stitching your current projects to that direction. Be vocal about it. Ask for projects that align with that trajectory.
One of my coachees knew she wanted to be a CPO one day, so she prioritized building comp bands, running performance reviews, and facilitating org design work. Guess who’s now Head of People at a Series D startup?
You don’t drift into those kinds of roles. You build your way toward them - piece by piece, conversation by conversation.
Step 3: Stop being the workaround 💡
Above, the OP said something in your note that hit me:
“I default to working around others instead of pushing back and fighting for what’s important.”
This is very common for operators, especially ones who are emotionally intelligent and conflict-avoidant. You think, “I’ll just get it done quietly. It’s easier that way.”
But over time, you start building departments that aren’t designed to thrive. Instead, they make stability the main objective at all costs.
When you do this, you set up your departments for failure, because they have no clue how much you’re doing and where you’re plugging in the holes. And the moment you step away because of an illness or burnout, everything falls apart. You can, and should, prevent this!
So here’s the shift:
When something feels misaligned, speak up - even if it slows things down.
When you’re building new systems or departments, ask: “What will make this sustainable without me needing to plug the holes?”
Stop assuming it’s your job to be everyone’s bridge. Sometimes the better move is to let the bridge collapse - and rebuild something better with the right people at the table.
And yes, this will feel uncomfortable. You will feel like “the difficult one.” But if you’re clear, kind, and grounded in the success of the business - it won’t be seen as antagonistic. It’ll be seen as leadership.
Step 4: Track your work and your emotions 💡
Everyone says: track your time. And you should!
But even more important than logging hours is logging how each project made you feel.
Was it:
Energizing or draining?
Clear or ambiguous?
Autonomously driven or painfully collaborative?
Tactical or strategic?
This kind of reflection is where you spot patterns. It’s where you discover, “I hate managing projects without clear scope,” or “I actually love working with the eng team more than I expected.”
You don’t want to get to the end of your CoS tour and say, “I did a lot of stuff.”
You want to say, “Here’s what I loved, here’s where I grew, and here’s what I want more of next.”
Keep a running doc. Review it monthly. Use it in your 1:1s. You are your own best data source.
Last thing I’ll say…
CoS is a launchpad, but only if you build the rocket.

It’s so easy to get swallowed up in being indispensable, in plugging holes, in staying in motion. But motion isn’t the same as progress.
So:
Know your Zone of Genius
Point toward your North Star
Push back when it matters
Track your growth as you go
And give yourself the grace to evolve along the way. You don’t need to have it all figured out today. You just need to stay awake to what matters.
Always here cheering you on,

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About Regina Gerbeaux
![]() | Regina Gerbeaux was the first Chief of Staff to an executive coach who worked with Silicon Valley’s most successful entrepreneurs, including Brian Armstrong (Coinbase), Naval Ravikant (AngelList), Sam Altman (OpenAI / Y Combinator), and Alexandr Wang (Scale). |
Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.
Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.
She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.
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