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I Recently Became Chief of Staff. Here Is What I Have Figured Out So Far.

August 2026

I started as Chief of Staff recently. I am still figuring out what the role actually means, which I am told is a completely normal experience for anyone who has ever held it. Every person I have spoken to who has done this job has described some version of the same first few weeks: a lot of observation, a lot of listening, and a slightly uncomfortable feeling that you should be doing more than you are.

Chief of Staff is one of those titles that means something different at every company that has one. I have explained mine about fifteen times already and given a slightly different answer each time, which is either a sign that I am still calibrating or that the role genuinely is whatever you make it. Possibly both.

Team collaborating at a strategy session
Recently started in the role. Still figuring it out. Writing about it anyway.

What I knew going in was that the core of the work is synthesis: making sense of what is happening across the organisation and making sure the right people have the right context to make good decisions. Research, communication, tracking, preparing, following up. I knew that part intellectually. What I did not anticipate was how much of the job would be about slowing down before speeding up. About resisting the instinct to fix things immediately and instead asking whether the thing actually needs fixing, and if so, by whom.

What makes 2026 different from the version of this role that existed a few years ago is AI. Not in a dramatic, overnight way. In the quieter way that any significant capability shift reshapes work gradually and then suddenly all at once.

45%of work activities could be automated with current AI, freeing time for higher-order workMcKinsey Global Institute, 2024
3 to 4xfaster output on knowledge work tasks with effective AI useHarvard Business School and BCG Study, 2023
40%of a typical CoS week historically spent on mechanical synthesis and communication tasksChief of Staff Association, 2024

The mechanical work of a Chief of Staff role, producing briefing documents, competitive analyses, meeting summaries, stakeholder updates, can now be done in a fraction of the time it used to take. I produce a first draft in the time it used to take to open the right documents. The research phase of a brief that once took a day takes an hour. None of this is perfect, and all of it requires judgment and editing. But the compression is real, and it changes the shape of the job.

What fills the space is interesting. The mechanical layer shrinks and what replaces it is the work that does not compress: being in rooms, reading dynamics, building relationships, making judgment calls on things that do not have a clean answer. I think this is the real story of what AI does to knowledge work. Not replacement. Compression of the mechanical, elevation of the human.

"The person who refuses to use AI in a role like this is competing against someone with three extra hours a day for the parts that actually require a person."

Something I keep coming back to, early in the role

Early in the role, I am not sure I am getting this right yet. The honest version is that I am still in the stage of watching, building context, and trying to understand what useful actually looks like in this specific environment. What I do know is that the job is evolving, that it is going to keep evolving, and that figuring out how to stay useful in that environment is itself a significant part of the work.

The noise is louder than ever. Figuring out which of it is signal is still entirely human.

Sources

  • McKinsey Global Institute: The Future of Work After COVID-19 (updated 2024)
  • Harvard Business School and BCG: Navigating the Jagged Technological Frontier (2023)
  • Chief of Staff Association: 2024 State of the Role Report
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