AI for your role

AI for Chief of Staff

Run the office of the principal with less grunt work and sharper output.

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The shift

How AI is changing the Chief of Staff role

AI now handles the document-heavy parts of the role: drafting board decks, summarizing long status reports, and turning messy meeting notes into clear action lists. It can pull together updates from multiple teams into one briefing and flag what the principal actually needs to decide. The result is more time for the judgment calls and relationship work that only you can do.

What AI can take off your plate

  • Transcribing meetings and producing action lists with owners and dates
  • Drafting first versions of briefings, board slides, and recurring updates
  • Summarizing long packets, contracts, and reports down to decisions and risks
  • Rolling up status from multiple teams into one consistent format
  • Cleaning up and reformatting your rough notes into shareable documents

What stays distinctly human

  • Reading the room and managing relationships with the executive team
  • Deciding what the principal actually needs to see versus what can wait
  • Handling sensitive personnel, conflict, and confidentiality matters
  • Making judgment calls when teams disagree and the data is incomplete
  • Building trust so leaders tell you the real status, not the safe one
Tools

Five AI tools for Chief of Staffs

ChatGPT
A Chief of Staff drafts executive briefings, rewrites a CEO email in the right tone, and turns rough notes into a structured agenda.
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Otter.ai
Records and transcribes leadership meetings so you get searchable notes and a list of decisions without typing during the conversation.
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Notion AI
Summarizes project pages, generates status rollups across team docs, and keeps the operating cadence wiki current.
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Microsoft Copilot
Pulls answers from your Outlook, Teams, and SharePoint to draft updates and catch you up on threads you missed.
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Claude
Reads long documents like board packets, contracts, or strategy memos and gives you a faithful summary with the open questions called out.
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Prompts

Five prompts to try today

Paste these into Claude or ChatGPT and replace the bracketed parts with your own details.

1. Weekly leadership briefing
You are my briefing assistant. Turn the following raw updates from team leads into a one-page brief for [executive name]. Group by [Sales, Product, Operations]. For each, give 2 lines of status, any decision needed, and any risk. End with a 'needs your attention this week' list of no more than 5 items. Updates: [paste updates]
2. Meeting follow-up
Here are my notes from a meeting with [attendees] on [topic]. Produce: 1) a 3-sentence summary, 2) a decisions list, 3) an action table with owner, task, and due date, 4) any unresolved questions. Keep owners exactly as named in the notes. Notes: [paste notes]
3. Board deck outline
Build a board meeting deck outline for [company] covering Q[X]. Include sections for company metrics, financials, strategic priorities, risks, and asks of the board. For each section list the 2-3 slides needed and the key message per slide. Our top themes this quarter are [theme 1, theme 2, theme 3].
4. Tone match an exec email
Rewrite the draft below so it sounds like [executive name], whose style is [direct, warm, brief]. Keep it under [150] words, keep all facts, and make the ask clear in the first two sentences. Draft: [paste draft]
5. Conflicting updates check
Compare these status reports from different teams and tell me where they disagree, duplicate effort, or depend on each other. List each issue with the teams involved and a suggested question I should ask. Reports: [paste reports]
The playbook

Every AI play for Chief of Staff

Your full AI playbook for your role — updated every week. Tap any card for a step-by-step walkthrough and examples.

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A day in your inbox

This is the kind of brief a Chief of Staff gets, every weekday morning.
Monday morning
✦ Personalized for: Chief of Staff
Your PlaybookFirst drafts
Turn a blank page into a solid first draft

The move that gets you past the hardest part of any task — starting. Works for an email, a plan, a report, a tricky reply. Free, no login.

ChatGPT  FREE  a free AI assistant that drafts, rewrites, and thinks through problems with you

1

Go to chatgpt.com (the free tier is fine) and describe what you need in plain words. Give it the goal, the audience, and any facts it should use:

I need to write [what]. It's for [who], and the goal is [what you want them to do or understand]. Here are the key points: [paste your rough notes]. Draft it in a clear, direct tone. Ask me anything that's missing first.
2

It drafts. Now make it yours — push back in the same chat:

Make it shorter and less formal. Cut anything that sounds generic. Keep the part about [X].

You go from staring at nothing to editing a real draft in two minutes. Editing is always easier than starting.

Your role, all in one place
  
Tools, prompts & tricks
Your full library, one tap away.
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Your playbook
Every entry, building each week.
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How AI is changing your role
Where your work is heading.
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