It's Time to Find Your Chief of Staff.
Every CEO I talk to right now is doing the job of three people, and calling it "management."
The hospital CEO in rural Kansas is triaging a staffing crisis before 6am and drafting a board deck at 9 pm. The startup founder sitting on a $1B valuation still opens their own inbox. And the solopreneur who built a $1M-a-year business alone? She's still answering every DM personally, because there's no one else to hand it to.
Here's my end-of-month, no-mitigating-language opinion: all three of you need a Chief of Staff.
What a Chief of Staff Actually Is
A Chief of Staff is the person who translates your intention into execution. They don't run the org chart — they run you: your calendar, your priorities, your follow-through, your reputation in every room you can't personally be in.
They make decision points. They own action items. They do not set strategy — that's still your job. Their job is making sure your strategy actually happens, on time, without seventeen people needing a meeting to confirm what you already decided three weeks ago.
A Role Older Than Your Org Chart
This isn't a Silicon Valley invention. The Chief of Staff has been quietly running the show since Napoleon appointed Louis-Alexandre Berthier to the job in the early 1800s — the first officer whose entire mandate was managing information flow and execution for one very busy commander.
Louis-Alexandre Berthier- Born 1753, Versailles, Kingdom of France | Died 1815 (aged 61) Bamberg, Kingdom of Bavaria
By the late 1800s, Prussian, British, and French militaries had formalized the role, with strategists like Helmuth von Moltke the Elder turning "chief of staff" into a real profession rather than a favor for a friend.
The title crossed into politics next. H.R. Haldeman under Nixon, James Baker under Reagan, Leon Panetta under Clinton, Rahm Emanuel and Denis McDonough under Obama, Dick Cheney under Ford — every modern White House Chief of Staff has done the same job: control access, manage the agenda, and tell the most powerful person in the room the truth nobody else will (Institute of Politics, Harvard).
And in January 2025, Susie Wiles became President Trump's chief of staff — and the first woman in American history to hold the job, after decades running campaigns and political operations from behind the scenes in Florida.
Two centuries after Berthier, the job description is basically unchanged: know everything, say little publicly, and make the person you serve better at their job.
Corporate America caught up too. Before she ran Facebook's operations, Sheryl Sandberg was Chief of Staff to Larry Summers at the U.S. Treasury Department — a training ground for exactly the skill set every CEO wants sitting next to them today
What the Role Looks Like Today
Strip away the history and here's the job description I'd actually write:
They speak for you in the room you can't be in — and the room trusts what they say.
They convert decisions into action items, not into slide decks about the decision.
They do not guide strategy. That's still on you. They guide what happens after strategy.
They give you back hours — the ones currently being eaten by status meetings, inbox triage, and people who "just need five minutes."
And when someone decides they'd like to monopolize your time, your attention, or your emotional bandwidth with drama that isn't actually urgent — your Chief of Staff is the cold water on that fire. Every time.
The Part Nobody Puts in the Job Description
A great Chief of Staff has an unfiltered opinion and no mitigating communication style. They will not say words to make you feel better about bad choices. They can disagree with you, bristle at you and still keep their job.
They'll tell you the meeting was a waste of everyone's time.
They'll tell you the hire isn't working. They'll tell you what the board is thinking before your board does.
And the best ones have something closer to a sixth sense than a skill: they can read the breadcrumbs in your tone, your gait, your intention, and your attention — and know something's off before you've said a word about it. That's not administrative support. That's a strategic instrument, and it's rare.
7 Ways to Find Your Chief of Staff (and Actually Use Them)
Promote from within. Your sharpest operator already speaks your shorthand. Use them on one high-stakes project first — not your entire calendar — and watch how they handle ambiguity.
Recruit from consulting or banking backgrounds. These are people trained to walk into chaos and build a framework by Thursday. Use them on your messiest, most undefined problem — that's where they earn their keep.
Run a real, retained search. Don't let this be a democratic hire from within. If you don't have the bandwidth to run a broken hiring process on top of running your company, that's a search firm's job, not yours.
Look at the best assistant or manager nobody's promoted yet. Half the time, someone in your org is already doing 60% of this job unofficially. Give them the title, authority and tools to match the work.
Go fractional first. If you're the $1M solopreneur reading this thinking "I'm not ready for a full-time hire" — you're right, and you don't have to be. Start with 10 hours a week aimed at your worst bottleneck. It could be your spouse who is only on the outer rim of the organization but still in the know, or a top-tier remote professional you can leverage as you grow.
Interview with scenarios, not resumes. Don't ask what they did. Ask what they'd do: "The board meeting is in six hours and the numbers just changed. Walk me through your next thirty minutes." Watch how they think.
Check references for candor, not likability. Ask their last boss: "Tell me about a time they told you something you didn't want to hear." If the answer is a long pause, keep looking.
Utilizing the hire: once you have one, use them for decisions and action — not validation. Give them real authority to do great work on your behalf to see your organization scale, the drama drop, and the real results happen.
