Where AI Actually Creates Leverage for Chiefs of Staff

Beyond task automation and into decision clarity

There’s a lot of conversation right now about how Chiefs of Staff should be using AI. Most of it focuses on productivity — drafting emails faster, summarizing notes, organizing documents. Those things can be useful, but they’re not where the real leverage lives in this role.

Chiefs of Staff sit in a very specific place inside an organization. We see information before it’s fully formed. We understand how different teams interpret the same issue. We often know where friction is likely to appear before a decision is even made.

That’s where AI can actually help — not by doing the work for us, but by helping us structure thinking before leadership walks into the room.

When I use AI in this role, it’s rarely about writing something from scratch. It’s much more about pressure-testing ideas. If a decision is being framed one way, I’ll often ask the system to surface counterarguments or alternative interpretations. Sometimes it will point out gaps that weren’t obvious at first. Other times it simply helps organize a messy set of inputs into something clearer.

That clarity matters more than speed.

Another place AI can be helpful is when comparing options. Many executive decisions involve tradeoffs that are scattered across emails, documents, conversations, and meeting notes. AI can help lay those out side-by-side so the implications are easier to see. It doesn’t decide which direction is right, but it can make the structure of the decision more visible.

The same is true for preparation. Chiefs of Staff spend a lot of time thinking about what might happen in the next meeting, the next board session, or the next leadership conversation. AI can help generate possible questions, identify areas that might trigger debate, or highlight assumptions that haven’t been tested yet.

None of that replaces judgment. It simply strengthens preparation.

Another interesting dynamic right now is how quickly the Chief of Staff role itself is growing. As organizations become more complex and the pace of decision-making accelerates, executives increasingly rely on someone who can synthesize information, connect signals across teams, and help shape decisions before they become public commitments. AI is actually amplifying that need, not replacing it. The more information organizations generate — and the faster it moves — the more valuable it becomes to have a trusted operator who can interpret that information, pressure-test it, and translate it into clear choices for leadership. AI can help process inputs, but it still takes human judgment to understand what matters, what’s missing, and how a decision will land inside the organization.

This is where the conversation around AI sometimes goes off track. The tool can sound confident, and it can generate polished language very quickly. But confidence isn’t the same thing as context. AI doesn’t know the personalities in the room, the history behind a decision, or the organizational dynamics that shape how something will land.

Chiefs of Staff do.

That’s why the goal isn’t to let AI drive the work. The goal is to use it as a thinking partner — something that helps you see the landscape more clearly before decisions move forward.

Used that way, AI doesn’t change the role of a Chief of Staff. If anything, it reinforces it. The value of the role has always been judgment, anticipation, and the ability to translate complexity into something leadership can act on.

AI just gives us another way to sharpen those instincts.

In many ways, AI doesn’t diminish the role of the Chief of Staff. It makes the role even more essential.