Aperture

The Career Path

Before You Say Yes: Negotiating the Chief of Staff Role

The CoS role fails more often from bad setup than bad execution. Five things to nail down with your principal before you start, and how long to stay.

Five questions to settle up front

Get these answered explicitly, ideally in writing, before day one.

  • Scope: which of the four buckets (cadence, projects, communication, decision support) is the priority in the first six months?
  • Authority: what can you decide, what can you speak to on the principal's behalf, and what is off limits?
  • Access: are you in the room for leadership meetings, board prep, and sensitive personnel topics?
  • Success criteria: what will be visibly better in six months if you are doing the job well?
  • Exit path: what does the role graduate into, and roughly when?

The tenure question

Most healthy CoS tenures run 18 to 36 months. Shorter, and you never compound trust; longer without a scope change, and the role can plateau. Agree early that the role is a chapter, not a destination, and revisit the exit conversation every six months.

Common failure modes to pre-empt

The role breaks when the principal delegates accountability without authority, when the leadership team sees the CoS as a spy, or when the job silently becomes an EA role. Naming these risks in the first month, openly, is the cheapest insurance available.

Put this into practice

Aperture is an AI Chief of Staff workspace: capture notes and threads, get action items and a daily brief automatically.

More on the career path

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