Toolkit

What documents should a new Chief of Staff set up first?

A new Chief of Staff needs four documents in the first month: the mandate, the leadership meeting agenda, the decision log and the weekly update to their principal. The rest arrive when the work does.

Build in the order your principal will feel it. The leadership meeting and the decision log come first, because the meeting is where the most people see your work at once. The weekly update comes next, because it is your channel to your principal. Then write briefs for your principal's two biggest meetings, draft the calendar rules and start a context file. Draft your mandate in week 3 and agree it in week 4, so you know which documents are yours.

Keep a template only for a document you write more than once a month. Hold each one to three tests: it repeats at least monthly, someone other than you reads it, and it changes a decision or a conversation. A document that fails the last test is a report, so send it less often or stop. The four-week toolkit setup plan ends with one Friday question: which document did nobody open this week?

What do employers expect a Chief of Staff to run day to day?

Employers mostly expect a Chief of Staff to run the operating rhythm and executive communication. In the Chief of Staff Network's Pathways Report, which analyzed more than 1,800 Chief of Staff job postings, 61% ask for the operating cadence, OKRs or KPIs, and 46% ask for executive communications. Next come strategy and annual planning (43%), cross-functional initiatives (41%), a thought partner on decisions (37%) and board and investor work (33%). Gatekeeping executive time appears in 20%.

Each ask is a recurring job that needs a document with an owner and a day of the week. The operating cadence needs a leadership meeting agenda, a decision log and a weekly scorecard. Executive communication needs briefs, a weekly update and a voice file for writing in your principal's name. Board work needs a deck calendar, a pre-read process and a list of the questions each director is likely to ask. Thought-partner work mostly happens in your 1:1, and its documents are the brief, with your recommendation first, and the decision log.

Some work is bigger than the postings suggest. Only 17% name leadership team management outright, yet running the leadership meeting also sits behind the 61% figure.

How does a Chief of Staff's toolkit change with company size?

The core documents stay the same as a company grows, but the number you run and the tools that hold them change. In a company under 50 people, three documents usually cover it: a shared priority list, the decision log and the weekly update. With no IT team, we'd use docs, one shared sheet, chat and one AI assistant, and write down which tool holds what. A founding team under 30 can run a 45-minute leadership meeting with no metrics section.

From 50 to 500 people, teams pick their own trackers and information splits. Use the tracker most leaders already open, and add company-wide search before another tracker. At 500 people and up, what the leadership meeting tells the company becomes a cascade note each leader takes to their own staff meeting.

In a large company you inherit a reporting stack, and most of your first quarter goes to merging and retiring documents. IT approves every tool, so work inside the approved list and request one tool a quarter. In a remote team, writing replaces hallway updates, so treat the weekly update and decision log as required. The toolkit overview has the full table.

How do a Chief of Staff's weekly documents fit together?

A Chief of Staff's weekly documents are built around the leadership meeting. Before it, collect agenda requests by a set day, build the draft with your principal, chase pre-reads 48 hours out, and send the final agenda and pre-reads 24 hours before. Written updates go out ahead too, so the meeting goes to two or three decisions and the issues that need the whole room. It ends with a read-back of each decision, its owner and its date. Our leadership meeting guide has the agenda.

After the meeting, send the decision log within an hour. Log decisions made elsewhere, in direct messages or on calls, within 24 hours. Your weekly update goes to your principal at the same time every week. On Friday, right after that update, spend about 20 minutes on the context file, decision log and commitments list. Add two lines to your stakeholder notes after each conversation and review the whole map once a month.

The board runs on a slower loop. A short monthly investor update keeps directors current between meetings and makes the next board pre-read much faster to write.

What does a Chief of Staff own, and what stays with the CEO?

The Chief of Staff owns the system around the work, and the principal keeps the relationships and the words they sign. The split holds across the daily work:

• Leadership meeting: the CEO chairs. You own the agenda, the pre-reads, the record of decisions and the follow-ups.
• Communications: you run the calendar of messages, the drafts, the cascade and the follow-up. Your principal approves everything they sign, and nothing goes out in their name that they haven't read.
• Board: the CEO owns the relationship with each director. You own the board calendar, the four-week work-back plan, the pre-read, the CEO's question prep and follow-ups within 48 hours.
• Calendar: you set the rules for your principal's time. An executive assistant, if there is one, schedules inside them.

Your judgment still goes on paper. Lead each brief with your recommendation, and give one in every research memo. When a decision belongs to another leader, send the memo to that leader with a copy to your principal, because a memo that pulls a decision up to the CEO teaches the leadership team to escalate everything. Your mandate says which documents are yours and which belong to someone else.

Where does AI help a Chief of Staff most, and where does it fall short?

AI helps a Chief of Staff most with drafts and first passes, while the recommendation and the final check stay with you. Use is already common: 90% of respondents to the Chief of Staff Network's AI Readiness Diagnostic have drafted internal communications with AI, and 70% have used it for board decks or executive briefings. Deeper use is rare. Only 12.5% of the 1,200+ senior leaders in the diagnostic connect AI to their other tools.

Good uses across the toolkit include drafts in your principal's voice from a file of their real writing, a board question bank that argues against the plan from each director's seat, deep research as the first pass of reading, meeting summaries with action items, and a weekly calendar look-ahead against a time budget. Deep research reports contain errors, so open the source behind every number you keep. A meeting summary that records a decision nobody made does more damage than no notes.

Start with one assistant your company approves, set up with your principal's context file. Security, compliance and ethics were the most common AI concern in the Chief of Staff Network's Chief of AI Report, at about 41% of responses.

What should a Chief of Staff keep out of writing and out of AI tools?

A Chief of Staff should keep candid reads on people out of writing and out of AI tools. Write down decisions, commitments, priorities and facts about who owns what. Keep who's struggling, who's leaving or who doesn't trust whom out of shared files, meeting recordings and AI prompts. The test from our context management guide: if you wouldn't read the line aloud to the person it's about, it doesn't go in. In a brief, write what people want and where they stand, and say anything about their performance, motives or relationships out loud.

If your leadership team uses an approved notetaker, agree topics that are never recorded: people decisions and performance, compensation, health or personal matters, legal matters and disputes, and anything under NDA or not yet public, such as deals and board matters. Board meetings get no notetaker at all, because counsel owns the record, and board packs go only into tools approved for confidential data.

The cost of a slip is your access. If people learn that a candid comment ended up in a shared summary, they stop being candid in front of you.