I’ve been Chief of Staff to the CEO at Pearl for nearly three years. I definitely don’t know everything but I’ve learned a lot. And with Pearl now hiring my successor, I wanted to share some lessons I picked up along the way.
There’s plenty of great content out there on the Chief of Staff role, including a recent article from a16z on how to hire one. This piece is simply about my personal observations: a practical view from inside the job.
1. Work in person with your CEO
Speed and trust are everything in this job and proximity is what unlocks both. Two minute conversations between meetings, early morning check-ins, debriefs at end of day. Those moments matter. You ramp faster, understand more, and eliminate friction.
2. Learn how your CEO’s brain works
Learn how they think, how they make decisions, and what they care about. Over time, you’ll be able to operate on their behalf because you’ll know their instincts.
3. Over communicate and be transparent
This relationship depends on trust. Close loops quickly, state facts clearly, and make it easy for your CEO to know what’s happening without them having to hunt for answers.
4. Be reachable
The job is high bandwidth and high velocity. Unless you’re sleeping, you should be reachable. It doesn’t mean you have no personal life but you need to be good at juggling. Responsiveness keeps things moving and helps your CEO make real-time decisions.
5. Be the sounding board, not the yes person
Your CEO does not need another person agreeing with them. They need someone who will push back thoughtfully, ask hard questions, and pressure test ideas.
6. Stay obsessively organised
You don’t need to memorise every detail, but you need systems that allow you to find what you need quickly. Trackers, notes, documents, follow ups. All of it matters. People should feel like you always have the full picture, because you do.
7. Never forget anything and always close the loop
Your CEO must trust that you will not drop anything. If someone asks for something, reply. If you commit to something, deliver. Reliability is key.
8. Embrace the variability
The job changes every hour. In one day you might interview a potential new hire, welcome a new joiner, present to the Board, host a CEO dinner, run the all-hands meeting, streamline a workflow, finalise the annual plan, plan a client roadshow, and review pulse check results. You have to enjoy switching contexts constantly.
9. Embrace ambiguity
Similarly, there is no neat job description. The role expands and contracts constantly based on the company’s needs. Instead of resisting that fluidity, lean into it.
10. Make time for people and be appreciative
You are a proxy for the CEO and leadership so people need to be able to come to you with concerns, ideas, or context. Meet new hires early and understand what matters across the company. And be genuinely appreciative. You will ask a lot of those around you and their time and effort are never guaranteed. Don’t take that for granted.
11. Invest in the external ecosystem early
You’ll work closely with investors, partners, and clients across fundraising, events, board meetings, and everything in between. Being known and knowing them makes everything easier and more effective. It also makes your work a lot more fun.
12. Bring the energy
Your tone becomes the company’s tone. Show up with good energy and start each day with optimism. People feel it even when you think they won’t.
13. No job is too small or too big
If something needs to get done and no one is doing it, take it. Some moments require shaping strategy. Others require jumping in on a small task that would otherwise slow people down. Nothing is beneath you.
14. Find your people
Find the people you trust and hold onto them. You will rely on them more than you expect. And tap into the broader Chief of Staff community. Every Chief of Staff, regardless of industry, deals with similar challenges.
15. Enjoy the immense privilege of the role
You get a front-row seat to how the company really works, how decisions are made, and how leaders think. You have influence without authority and visibility without ego. It is a remarkable job that shapes your career fast and leaves a lasting mark.
I am grateful for every minute of it and excited for the next person to take the baton.
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