The Chief of Staff Role is About to Change Forever
Paul Graham recently tweeted about asking ChatGPT a question that stuck with me. I’m paraphrasing, but he was essentially asking:
“What’s the obvious-yet-radical shift AI will bring that we’ll only recognize in hindsight?”
It’s a sharp way to think about change. Not just what’s happening now, but what will feel obvious later—when we look back and say, of course that was going to happen.
I keep coming back to Chiefs of Staff. Not in the “AI is replacing this role” kind of way, but in the “this role is evolving, and most people won’t see it coming” way.
Right now, Chiefs of Staff are the glue that holds leadership teams together. They smooth out communication gaps, make sure strategies don’t go off the rails, and keep a company’s priorities in sync. It’s a role built on handling complexity—coordinating across teams, keeping executives aligned, and making sure nothing critical slips through the cracks.
And a lot of that work is deeply operational. Chiefs of Staff take meeting notes, pull together summaries, track decisions, compile reports, and chase down action items.
That’s the part that’s about to shift.
AI is Taking Over the Operational Load
It’s already happening. AI can now take meeting notes, generate summaries, analyze data, and even draft strategic briefs. Over time, these tools will only get better. The routine, logistical side of the Chief of Staff job—the part that keeps things moving but isn’t necessarily high-value—isn’t going to need a human in the same way it does now.
And if your value as a Chief of Staff comes from keeping leadership organized, scheduling follow-ups, and making sure things don’t fall through the cracks, that’s a problem. Because AI can do that too. Faster, cheaper, and with fewer mistakes.
That doesn’t mean the role is disappearing. But it does mean it’s changing.
The Real Value of a Chief of Staff Was Never Just Operations
The best Chiefs of Staff already know this. Their real value has never been about keeping the trains running. It’s been about knowing which tracks the company should even be on.
AI can process information, but it can’t understand the subtle dynamics of a leadership team. It doesn’t notice when two executives are saying the same thing but meaning completely different things. It doesn’t pick up on the quiet shift in priorities that no one’s said out loud yet. It doesn’t know when to push back on an idea that sounds good in theory but won’t work in practice.
That’s where the shift is happening. The most valuable Chiefs of Staff aren’t the ones who execute someone else’s plan efficiently. They’re the ones who help shape the plan in the first place.
How to Make Sure You Stay on the Right Side of This Shift
If AI is eating the operational side of the job, then the question is: what’s left?
A lot, if you lean into the right things.
First, get comfortable challenging leadership. AI can summarize a meeting, but it can’t say, “I think we’re focusing on the wrong thing here.” It can’t tell a CEO when they’re overcommitting or flag when a conversation needs to happen before it turns into a bigger problem. The best Chiefs of Staff know when to step in, ask the hard questions, and make sure leadership isn’t just making decisions but making the right ones.
Second, become the person who connects the dots. AI is great at delivering insights, but it has no judgment. It can tell you what happened, but it can’t tell you why it matters. Someone still needs to step back and see how everything fits together—how different teams, projects, and priorities align (or don’t). That’s where a great Chief of Staff thrives.
Third, shift from being the person who keeps things running to the person who ensures the right things happen. That means not just executing leadership’s ideas, but shaping what gets prioritized in the first place. It means spotting problems before they become crises. It means keeping leadership honest about what actually matters, not just what sounds important in the moment.
The Future Chief of Staff is a Strategic Partner, Not an Operator
The shift is happening whether people realize it or not.
Some will try to hold onto the operational side of the job because it’s tangible, because it feels productive, because it’s what the role has always been.
But the Chiefs of Staff who embrace the change—the ones who step up as strategic enablers instead of executive assistants—will be more valuable than ever.
AI won’t replace great Chiefs of Staff. It will expose the ones who were relying too much on process over judgment.
The work is changing. The only question is whether you’re changing with it.
