Empowering Chiefs of Staff to excel together

The Chief of Staff role runs through one relationship: the one with your principal. Seven patterns from the operators who built that partnership well and turned the title into a real strategic seat.

The Chief of Staff is the CEO's secret weapon in the AI age, but most in the title aren't yet strategic partners. When to stay, grow in place, or go.

Most strategic plans don't fail because they're wrong, they fail in the handoff from leadership to the rest of the org. The piece walks through the four places that handoff usually breaks: the reasoning gets diluted as it passes down through summaries and slides, ownership gets assigned after the plan is already built instead of before, nobody's actually responsible for keeping the plan current month to month, and even a solid plan loses out to whatever's loudest that week if it's not deliberately repeated. The fix for all four is roughly the same: treat the cascade as an ongoing conversation rather than a one-time handoff, bring second-line owners in early, share the reasoning not just the conclusion, and keep saying it.

A Chief of Staff built an AI version of his own job — daily briefings at 6am, automated 1:1 meeting prep, and an agent loop that progresses tasks while he sleeps. A walkthrough of how "Peter," an AI chief of staff built with Claude, runs a working day.

What do Chiefs of Staff do after the role? Tristan Lim maps five career paths — from fractional work to building your own thing — and what they all have in common.