How to brief your CEO

It's 8:52. Your principal has a 9:00 with the head of sales about a pricing change, and they're reading on their phone in the back of a car. They'll give your brief about ninety seconds.

In those ninety seconds they need to know what the meeting is for, what you think they should do, and who is likely to push back. If your brief opens with three paragraphs of background, they'll walk in with the background and none of the rest. This is part of our Chief of Staff handbook; the note you send before your 1:1 has its own guide, on the weekly update.

What is a briefing memo, and what does a principal need from one?

A briefing memo is a short written note that prepares your principal (the executive you work for) for a meeting, a decision or a conversation. What they need from it is speed: the point, your view and the risks, readable in a minute or two.

The format changes with the job the brief has to do. These are the five you'll use most, counting the verbal brief.

The lengths are our recommendation, based on how principals read: in gaps between meetings, on a phone, often minutes before they need the information.

Employers ask for this directly. In the Chief of Staff Network's 2026 Pathways Report, 46% of the more than 1,800 Chief of Staff job postings we analyzed ask for executive communication and content, 37% for a thought partner on decisions, and 33% for board and investor work. Briefing sits inside two of the four core responsibilities: communication, and priorities and decisions.

If your principal has an executive assistant, agree the split once: they own logistics and the calendar, you own the substance. The brief is often the only artifact of your judgment your principal sees before a meeting, and one that contains a view they hadn't considered gets every later brief read.

This week, check the first two lines of the last three briefs you wrote. If neither contains the ask or your recommendation, rewrite the openings before you send the next one.

What goes in a meeting brief?

A meeting brief has six parts, in this order: the ask, your recommendation, the context, who's in the room, the risks and what happens after. Keep that order even when the brief is three lines long, because your principal may stop reading at any line.

# Brief: [meeting name] · [date, time, length]

**The ask:** What you need to get from this meeting, in one sentence.

**My recommendation:** The position I suggest you take, and the main reason, in two lines.

**Context (3 to 5 lines):**
- What changed since you last discussed this (with numbers and dates)
- What's already been decided
- What's still open

**Who's in the room**
- [Name, role]: what they want, where they stand, what they'll push on
- [Name, role]: ...

**Risks:** What could go wrong in the room. Anything sensitive, I'll tell you in person.

**Questions to ask:** 2 or 3.

**If it goes sideways:** Your fallback position.

**After the meeting:** Follow-ups with owners and dates. I'll send the summary to [names] by [time].

**Appendix:** Links to the deck, data and prior decisions.

# Brief: Q4 pricing with Dana and Sam · Tue, 2:00, 45 min

**The ask:** Agree a pricing change Dana's team will sell.

**My recommendation:** Approve the 8% list increase with a 90-day cap on discounts. It protects margin without stalling her pipeline.

**Context:**
- Discounts averaged 14% last quarter, up from 9%
- Two of the five largest deals closed at the discount ceiling
- Finance wants the increase live by January 1

**Who's in the room**
- Dana, VP Sales: wants pricing settled this quarter so her team can set targets; will push for a longer discount window
- Sam, Finance: supports the increase; will resist any cap above 90 days

**Risks:** Dana agrees in the room and her managers keep discounting.

**Questions to ask:**
1. Which open deals would the cap touch?
2. What would make 90 days workable for your managers?

**If it goes sideways:** A 60-day trial with a check-in on the discount rate.

**After the meeting:** I'll send the summary to Dana and Sam by 5pm.

Start with the ask, in one sentence. "Agree a pricing change with Dana that sales will actually sell" is an ask. "Pricing discussion with Dana" is a calendar title.

Then your recommendation, the part new Chiefs of Staff leave out most often because they worry about overstepping. Your principal can disagree with a recommendation in two seconds, and if you don't have a view yet, write that and say what would give you one. I'd rather read a recommendation I disagree with than a page of balanced context.

The filled example above uses made-up numbers. A weak version of the same brief would open: "Background: Q3 pricing review. Sales has raised concerns about discounting since the July change." Your principal would finish that line still guessing what you want from the meeting.

Context, people and risks

Context comes third, in three to five lines: what changed since your principal last thought about this, with numbers and dates. Anything longer goes into the appendix.

Who's in the room is the section that makes a Chief of Staff's brief different from one an assistant would write: one line per person on what they want, where they stand and what they'll push on. You know this because you talk to people your principal doesn't have time to talk to. Risks are what could go wrong in the room, with the fallback if it does.

The pricing brief in the example comes in under 200 words, and every line changes what your principal says or tells them what to watch for.

Where briefs go wrong

The hardest case is disagreeing with a position your principal has already taken. Write your recommendation anyway, say plainly that it differs, and give the one fact that would change their mind. If they've heard the argument and decided, a brief that repeats it reads as lobbying; help their position land, and take the disagreement to your next 1:1.

The other is briefing every meeting the same way. When your principal is a guest in someone else's meeting, the ask is usually what they should say or support, and the people section matters more than the context. For an investor or customer meeting, the people lines come from your CRM, past notes and the account owner, so say where each came from.

Over a quarter, your principal starts asking "what's the ask?" before meetings that don't have one, and people start briefing you. Once the head of sales knows your principal walks in with a one-line read on where she stands, she'll call you the day before to make sure it's accurate. Write the template down, so whoever covers for you produces the same shape.

Put the ask and your recommendation in the first two lines of every brief, before any background.

How do you write a decision memo?

A decision memo asks your principal to make one decision, by a date, and recommends which way to go. It lays out the options honestly, names the trade-offs, says who has been consulted and describes what happens once the decision is made.

Write the decision as a question at the top: "Do we move the enterprise launch from March to May?" If you can't phrase it as one question, you have two memos.

# Decision memo: [the decision, as one question]

Decision owner: [name] · Decide by: [date] · Prepared by: [you]

## Recommendation
[Option] because [the one reason that matters most].

Confidence: high / medium / low, and what would change it.

## Why now
What happens if we wait, and what it costs.

## Options
| Option | What we get | What it costs | Main risk | Who it affects |
| --- | --- | --- | --- | --- |
| A | | | | |
| B | | | | |
| Do nothing | | | | |

## Trade-offs
What we give up with the recommended option, in plain words.

## Who has been consulted
- [Name, team]: supports / has concerns / opposes. What would change their view.

## After the decision
- First three actions, with owners and dates
- How we'll know it worked
- Review date

# Decision memo: Do we move the enterprise launch from March to May?

Decision owner: CEO · Decide by: Jan 20 · Prepared by: Chief of Staff

## Recommendation
Move the launch to May, because two of the three security features enterprise buyers asked for won't pass testing by March.

Confidence: medium. A clean test result on February 1 would change it.

## Why now
Sales has announced March to three prospects. Every week we wait makes the call to them harder.

## Options
| Option | What we get | What it costs | Main risk | Who it affects |
| --- | --- | --- | --- | --- |
| March as planned, without the features (do nothing) | The date sales announced | Rework after launch | First enterprise deals stall in security review | Sales, three prospects |
| May with all three features (recommended) | The product we promised | A quarter of enterprise pipeline | Prospects buy elsewhere while they wait | Sales, finance plan |
| March for a few design partners | Momentum and early feedback | Engineering time nobody has budgeted | A small team carries launch support | Engineering, customer success |

## Trade-offs
We give up a quarter of enterprise pipeline to ship something that passes a buyer's security review the first time.

## Who has been consulted
- Head of sales: opposes, because she announced March to three prospects. She'd accept May if we tell them ourselves this month.
- Head of engineering: supports May.
- CFO: has concerns about the pipeline gap and wants the revenue plan updated before the board meeting.

## After the decision
- CEO and head of sales call the three prospects by Jan 31
- CFO updates the revenue plan by Feb 7, in time for the board pre-read
- Head of engineering shares the Feb 1 test results with the leadership team
- It worked if all three prospects are still in the pipeline on March 31
- Review date: Feb 3

Write every option, including the one you don't recommend, well enough that its strongest supporter would agree you represented it fairly. A memo that stacks the deck gets found out in the meeting, by the person whose option you undersold.

The consulted section is where your political work shows: each person whose team the decision affects, their view and what would change their mind. Your principal sees the resistance before the room does, and can settle it in advance where the mandate gives them that call. After a few memos, leaders start lobbying you before you write, so describe every view the way its holder would.

Close with the first three actions, owners, dates and a review date; decisions without one tend to get relitigated by whoever lost. Send it two to three days ahead, because less than a day forces a decision on instinct. If your principal decides in the room, send it anyway, because it becomes the record of why the launch moved.

What the launch example shows

The launch memo above uses invented details. Read its consulted section first: the head of sales opposes the move and has named what it would take for her to accept it. Your principal now knows the real decision includes a call to three prospects and a revised revenue plan, before anyone walks into the meeting.

Judgment calls on a memo

Medium confidence is an honest answer, and more useful than a firm recommendation you'd back away from under questioning. If the evidence can't support a recommendation yet, recommend "not yet", name the date the evidence arrives, and say what waiting costs.

If the call belongs to another leader under your principal's decision rights, the memo goes to that leader with a copy to your principal. A memo that pulls a decision up to the CEO teaches the leadership team to escalate everything.

For a remote team, or a decision that doesn't need a meeting, send the memo with a comment deadline, collect objections in the document, and have the decision owner record the outcome at the top. Before you send any memo, run it past someone who reads the way your principal does, or use the prompt below to play that reader.

Act as my principal, [role], reading this decision memo in three minutes between meetings. Here is the memo: [paste].

1. In one sentence, what do you think I'm asking you to decide? If that differs from the decision I state, say so.
2. What is the first question you'd ask me?
3. Which option looks under-argued, and what evidence is missing?
4. Who is affected by this decision and not mentioned in the memo?
5. What would make you say "not yet"?
6. Rewrite my recommendation in 40 words or fewer, keeping my position.

Don't add facts. Where the memo needs data I haven't provided, say what's missing.

When do you send a pre-read, and how is it different from a brief?

A pre-read prepares a whole meeting, so everyone arrives with the same facts. A brief prepares only your principal, and adds what you'd never put in a shared document: your recommendation, who will push back and the outcome your principal wants.

Some leadership teams open meetings with ten minutes of silent reading. Most don't, and half the room skims the pre-read on the way in, so put the question for the room in the first line, keep it under five minutes and state the read time at the top. Our guide to the operating rhythm covers standard pre-reads for each recurring forum, and the meetings guide covers agendas and notes.

Whoever writes the pre-read shapes the decision, and leaders notice. I'd show every draft to the people whose work it covers, even when the deadline is tight. It costs a day, and it saves you a meeting that opens with someone disputing your numbers.

# Pre-read: [topic] · for [meeting], [date]

Read time: 5 minutes. Please read before the meeting; we'll start with questions.

## The question for this meeting
One sentence. What we need to decide or agree.

## Background (max 5 bullets)
- ...

## The data
One chart or table, with its source and date.

## Options (if we're deciding)
1. ...
2. ...

## Questions for discussion
1. ...
2. ...

## What happens next
Who owns the follow-up, and when the outcome will be shared.

What goes in a CEO daily briefing or weekly digest?

A CEO daily briefing gives your principal the day on one screen: the three things that matter today, the decisions waiting on them, what changed since yesterday and one thing to watch this week. Send it at the same time every day, before their first meeting.

Once your principal trusts that anything important will be in it, they stop scanning email and chat to find out what changed. Leave out one decision that was waiting on them, and the next morning they're back to scanning. Each line points to an action: "Board deck v2 is in your folder; I need your comments on slides 4 and 9 by Thursday" is a digest line, and "Board deck progressing" teaches your principal to skim.

The digest lists today's meetings with the one-line ask for each and links to the full briefs. On Fridays, the weekly update replaces it. Other leaders will ask to be on it; keep it for your principal, because a digest for six readers becomes a status report. I'd start with three days a week and go daily when your principal asks for it on the days it doesn't arrive.

# [Day, date] · Daily briefing for [principal]

**Three things that matter today**
1. [Item, with the decision or action it needs]
2. ...
3. ...

**Waiting on you**
- [Decision or approval] · needed by [date/time] · my recommendation: [one line]

**Today's meetings**
- [Time] [Meeting]: the ask in one line · [link to brief]

**What changed since yesterday**
- [Fact, with number and source]

**One thing to watch this week**
- [Risk or open question, and when you'll know more]

How do you brief on people and politics without putting it in writing?

Write down what people want and where they stand. Say out loud anything about their performance, their motives or their relationships, because a written brief can be forwarded, screenshotted or left open on a shared screen.

"Dana wants pricing decided this quarter so her team can set targets" is useful and fair to Dana. "Dana is worried about her number and will dig in" is a read you give your principal in the car or on a call.

The harder question is how you get honest information in the first place. Nick Greif, who was Chief of Staff to a Los Angeles City Council member before becoming Chief of Staff at InStride, told us on our podcast that he borrowed a rule from the press.

That let him raise issues with his principal without anyone knowing where they came from. The first time a confidence shows up in a brief with a name attached, people stop telling you things, and your briefs get worse.

How the three tiers work in practice

In his first year Nick met every VP and every director one to one and explained the rule in each meeting. Off the record was the default, on background meant he could pass the point on without a name, and on the record meant the person was happy to be named. As he put it, once you divulge a name, "it's over. You can't get that trust back."

The tiers map onto a brief. On-the-record views go in the people section with a name: "Dana wants pricing settled this quarter." Background goes in without one: "Two regional managers expect the cap to cost them deals." Off the record stays out of the document and shapes what you say in the car.

I'd add one exception when you explain the rule, up front: anything involving harassment, fraud or someone's safety goes to the people who have to handle it, whatever tier it was told in.

Where it gets harder

Small teams break anonymity: if a team has four people, "someone on the team" names them, so raise a pattern and keep the detail for the person who can act on it. In remote companies more arrives in direct messages, which screenshot as easily as a brief, so move anything sensitive to a call.

In the first months people test the rule with small things. If nothing comes back to them, the real problems start arriving, often weeks before they'd reach your principal any other way. Agree early that "someone who asked not to be named" is an acceptable answer when your principal asks who said it.

[SCOTT: how you briefed the CEO before a board or investor meeting at Spring, and what you kept out of writing?]

Your principal will repeat parts of your brief in the meeting, sometimes word for word, which is why you check every number twice. One wrong figure repeated by a CEO in front of the board costs more trust than a month of good briefs builds. Communication is one of the eight competencies in our Leveling Framework, and our guide to Chief of Staff skills covers stakeholder management.

How do you change a brief for a different principal?

Ask your principal how they like to read, then watch whether the answer is true. Some read every word of a two-page memo at night, others read the first line on a phone, and many say they want detail and then read the headline.

Rachel Peck, who was Chief of Staff to the founders of Harry's before founding Metronome (she also leads sessions in our Launchpad program), described in her episode on saying it well how long it took to write for two founders at once: a lot of time together, a lot of drafts and plenty of trial and error. Expect the first month of briefs to be calibration, which is one reason our first 90 days guide puts a written note to your principal in week four.

Track which sections of your briefs your principal reads, and cut the ones they skip.

Watch which briefs get a reply and which part the reply is about, which questions your principal asks that the brief already answered, and whether they forward your brief. Then adjust and say so: "I've moved the people section to the top, since that's what you ask about." When your principal changes, start again, and write down how each principal liked to be briefed for whoever comes next. Our post on strategic communication covers writing for different audiences.

How do you get your principal to actually read your briefs?

Send them at the same time and in the same place, keep them shorter than your principal expects, and if they still don't land, find out whether your principal is a listener. Some principals take in a ninety-second verbal brief better than any document.

Pick one home for briefs, whichever your principal already checks: a shared document, a calendar invite or a message thread. If a brief is late, say so in the first line. Keep the main brief to one screen; the appendix is for the meeting where your principal is challenged on a number and needs it in thirty seconds.

When your principal still isn't reading, ask: "Would a two-minute verbal version on the way in work better?" For a listener, the written brief becomes your preparation and the verbal brief the delivery. When a meeting lands with ten minutes' notice, text the ask, your recommendation and one risk.

How can AI help you draft briefs, and what has to stay yours?

AI is useful for the first draft and for pressure-testing: turning raw notes into the brief structure, summarizing long documents into context lines, and predicting the questions a reader will ask. The recommendation, the read on people and the decision about what to leave out stay with you.

In the Chief of Staff Network's AI Readiness Diagnostic, 90% of the 1,200+ senior leaders who took it had drafted internal communications with AI and 70% had used it for board decks or executive briefings, as we reported in our post on becoming Chief of AI.

Ana Flávia Silva, Chief of Staff at Section, described two practices worth copying in her episode on using AI to be more effective. Her team keeps a shared AI project loaded with the company's templates, so a new brief starts from the right structure. She was also building an agent to run the board deck through several models and draft the questions board members are likely to ask; for now she does that question prep herself.

Question prep is the part to automate first, because AI covers the obvious questions and leaves you time for the ones only you would think of. Use only tools your company has approved, check what they do with transcripts and customer data, and keep personal reads on people out of AI tools entirely. Our meetings guide covers recording consent, our guide to AI for Chiefs of Staff covers approved tools, and our AI setup guide covers connecting AI to your calendar and documents.

You're helping me, a Chief of Staff, write a meeting brief for my principal, [name, role].

How my principal reads: [e.g. on their phone between meetings; wants the ask first; skips long context].
The meeting: [name, attendees with roles, date, length, goal].
My raw notes: [paste notes, email summaries, numbers].

Write the brief in this structure:
1. The ask (one sentence)
2. My recommendation (two lines). If my notes don't state one, write [MY RECOMMENDATION] and never invent one.
3. Context: 3 to 5 lines, using only numbers and dates from my notes
4. Who's in the room: one line each on what they want and where they stand, only from my notes
5. Risks
6. 2 or 3 questions to ask
7. Follow-ups with owners

Rules: under 250 words. Use no information that isn't in my notes. Mark anything uncertain with [CHECK]. Leave out anything about a person's performance, health or personal life.

After the brief, list the three things a busy reader is most likely to misread, and how to fix each.

No tool knows that your principal and the head of sales had a difficult conversation last week, or that the CFO agreed to the plan in the hallway yesterday. That's the part of the brief your principal values most, so let a tool draft and spend your time on the lines only you could write.