Your first 90 days as a Chief of Staff

In your first weeks, everyone is pleased to see you and nobody is sure what you're for. The leadership team is waiting to find out whether you speak for the boss, report on them, or do the work they've been avoiding. Some new Chiefs of Staff go quiet for a month and surface to find the role defined as whatever nobody else wanted; others start fixing things on day two and spend month two repairing relationships.

[SCOTT: one line on your own first weeks at Spring, e.g. what you did first or what you'd change?] This is the plan I'd follow if I started on Monday. New to the role itself? Start with our Chief of Staff handbook. If you're the executive hiring, see how to hire a Chief of Staff for your side of the first 90 days.

What should you do in your first 90 days as a Chief of Staff?

Split the 90 days into three jobs: learn the business and your principal (days 1 to 30), take ownership of part of how the company runs (31 to 60), and prove the role with one piece of strategic work (61 to 90). Each month ends with a written check-in with your principal, so the two of you define the role on purpose.

Work in phases because a Chief of Staff's authority is borrowed. With no team or budget, you run on your principal's trust and the leadership team's willingness to answer your messages, and both take weeks to build. The phases map to the four core responsibilities: month one is seeing how priorities, the rhythm, communication and projects work today, month two is taking over part of the operating rhythm, and month three is shaping priorities with strategic work.

My take: treat the first 90 days as the start of a two-to-three-year tour. Probation asks "will they keep me?" The more useful question is "what will this role be by month 24, and what do I need to set up now so it gets there?"

The checklist below is the full plan; each phase is explained in the sections that follow. This week, put three dates in your principal's calendar: day 30, day 60 and day 90, thirty minutes each, titled "Chief of Staff check-in".

# My first 90 days: Chief of Staff to [principal]

Start date: [date]  ·  Check-ins booked: day 30 [date], day 60 [date], day 90 [date]

## Before day one
- [ ] 30 minutes with [principal]: what to take off their plate first, what failure looks like, who to meet first
- [ ] Access: calendar, leadership docs, metrics, board decks, current plan or OKRs
- [ ] Weekly 1:1 booked (45 to 60 min, for strategy; status goes in the written update)
- [ ] My one-page user manual written

## Weeks 1 to 2
- [ ] First real task taken over: [task]
- [ ] Listening tour: first 10 conversations booked
- [ ] Learn how [principal] likes to receive information (Slack, email, docs, verbal)
- [ ] Weekly update to [principal] started: decisions / what moved / what's coming / 1:1 topic

## Days 1 to 30: learn
- [ ] Listening tour done ([n] people), notes in one place
- [ ] Stakeholder map: who influences what, who needs what
- [ ] Four core responsibilities mapped: priorities / rhythm / communication / projects
- [ ] One small useful thing done for each leader
- [ ] One-page mandate drafted (week 3); agreed with [principal] (week 4)
- [ ] Day-30 memo sent; check-in held

## Days 31 to 60: own
- [ ] Running [meeting or process] end to end: agenda, pre-reads, decision log, follow-ups
- [ ] Mandate shared with the leadership team
- [ ] One metric I own: [metric], reported weekly
- [ ] Day-60 check-in held

## Days 61 to 90: prove
- [ ] Strategic project: [project], tied to [principal's top priority], result by [date]
- [ ] One dead initiative proposed for stopping, with its owner's agreement
- [ ] Keep / hand off / stop list agreed, with owners for every hand-off
- [ ] Day-90 review sent and held: what changed, next two quarters, expected tour length, next role

## Signals I'm on track
- Leaders bring me problems without being asked
- The meeting I run happens without [principal] chasing it
- [principal] sends me to a meeting in their place
- I can say in one sentence what the role changed

What should you do before day one?

Before you start, get three things: a 30-minute conversation with your principal about what they need first, access to the documents that show how the company runs, and a weekly 1:1 on the calendar. Then write a one-page user manual about how you work.

Ask your principal three questions. What's the one thing you most want off your plate in my first month? What would make you say in six months that this hire was a mistake? Who on the leadership team should I meet first, and who will be most skeptical of this role? The first answer is your first real task, the second is what your principal fears, and the third is where your hardest relationship will be.

Kyle Hagge did a version of this when he became Chief of Staff to Morning Brew's incoming COO: they agreed a short list together of events, the data and research team, and support for B2B sales. As he put it on our podcast, every piece of your work should ladder up to a company goal, or you'll struggle to explain your value later.

Access usually means the principal's calendar, the leadership team's shared documents, the metrics your principal checks, the last two board decks and the current plan or OKRs. If your principal hesitates on any of these, note it for day 30. Your user manual covers your hours, how you prefer to receive requests, how you give and want feedback, and what you're bad at; swap it with your principal's in week one.

What should you do in your first week as a Chief of Staff?

In your first week, do two things that pull in opposite directions. Take one real task off your principal's plate, ideally the one they named before you started. And start a listening tour without changing anything else.

In week one, take over the one task your principal named before you started, and change nothing else yet.

The fast part is about proof. Ana Flávia Silva was put on a partner call on her second day at Section and told the relationship was hers from then on. She ran the follow-up and started a partnership plan that week, and her principal later said that taking real work off her plate in the first 72 hours set Ana up to make a big impact.

The slow part is everything else. Marlen Heske, Chief of Staff at Enpal, warned on our podcast against spotting a problem on day one and solving it by day three. Change too early and you'll often be fixing something that was done that way for a reason you haven't heard yet.

Start the listening tour

A listening tour is a set of short one-to-one conversations with the people who matter to your principal's agenda, all asked the same few questions. Juhi Kabra, former Chief of Staff at Redesign Health, who now leads sessions in our Launchpad program, suggests that at a company of 150 people or fewer you try to meet nearly everyone over your first six weeks, 20 or 30 minutes each. I'd start with the leadership team. At a bigger company, cover your principal's direct reports, their direct reports, and the people everyone says to talk to.

That unofficial org chart is the tour's second output: who influences decisions, who people go to when they need something done, and who will quietly block a change they weren't consulted on. Write it as a simple stakeholder map with each person's priorities, what they need from your principal and how they like to communicate.

Learn how your principal likes to receive information too. Kyle Hagge sent his COO a Slack message long enough to scroll, and the reply made clear that long updates belong in email. Watch what your principal reads, skims and ignores, and match it.

# Listening tour kit

## The invite (send 2 to 3 days ahead)
Hi [name], I've just started as Chief of Staff to [principal]. I'm spending my first few weeks listening before I change anything. Could I have 25 minutes with you this week or next? I'll ask everyone the same four questions so I can see the full picture:

1. What are you and your team trying to get done this quarter?
2. What's getting in the way, and what's stuck waiting on a decision?
3. What do you wish [principal] knew, or heard more often?
4. If you were me, what would you work on first?

Nothing you say will be quoted back with your name on it.

## In the meeting
- 30-second intro, then listen. Aim to talk less than a fifth of the time
- Same four questions, in the same order
- Close with: "Who else should I talk to?" and "Is there anything you'd like me to take off your plate?"
- Write up notes the same day, in one place only you can see

## Your notes, per person
- Name, role, team
- Their top priority this quarter
- Blockers and decisions they're waiting on
- What they think the principal doesn't hear
- What they'd fix first
- How they like to communicate
- One small thing you can do for them

## The read-out (by day 30, to your principal first)
1. What I heard: the 3 to 5 themes that came up most, with how many people raised each
2. Where people disagree with each other, or with the stated plan
3. Decisions people are waiting on, and who they're waiting on
4. Work nobody owns
5. What I recommend we do about it, and what I'd take on myself
6. What I'd share with the leadership team, and what stays between us

Days 1 to 30: how do you learn the job without disappearing?

In your first month, map the four core responsibilities in your principal's world, deliver your first real task, do one small useful thing for each leader, and finish with a written day-30 memo to your principal. Learning is the main job, but it has to produce something your principal can read.

The risk in month one is invisibility, and the answer is small, visible help. Juhi Kabra's advice is to list every leader and find one small thing to do for each, even taking notes and sending the follow-ups. Her test: every executive should see you as an ally, including the ones you don't report to.

Map the four core responsibilities

As the tour runs, sort what you hear. Priorities and decisions: does the leadership team agree on what matters this quarter? Rhythm: which meetings and planning cycles exist, and which ones produce decisions? Communication: what does your principal not hear, and what does the organization not hear from them? Projects: which cross-team projects have no clear owner?

One of the four is usually much weaker than the others, and that's where your role will earn its keep. In a fast-growing startup it's often rhythm, because the meetings that worked at 30 people stopped working at 120. At a larger company it's more often communication, because bad news takes three layers to reach the top.

Play the tour back

Lu Borko ran a listening tour on joining Manychat as Chief of Staff and took no direct action on it; it became a read for the CEO and COO on where the company stood. Her reflection on our podcast is that next time she'd start with an angle, something specific to investigate, so the tour drove outcomes too. Either way, someone besides you has to read the result. Twenty-five people just told a new person what's broken, and if nothing comes of it, they conclude you were collecting information for the boss.

Here's an illustrated read-out from a 150-person company, after 22 conversations. It fits on one page and leads with themes, each with a count and a proposal.

1. "Priorities: 15 of 22 people named a different top priority for this quarter. Most named the one their own leader talks about most. I propose we publish the three company priorities in one place before the next planning cycle."
2. "Rhythm: the Monday leadership meeting was mentioned 11 times, mostly as a status round where decisions get reopened afterwards. I propose I take it over from week 5, with a decision log."
3. "Projects: the partner integration came up 9 times. Sales and product each think the other owns it. I propose one owner and a date, decided at our day-30 check-in."
4. "What I'm not proposing yet: anything on hiring or org design. I heard concerns, but not enough to recommend a change."

Themes carry counts, and quotes stay anonymous unless the person agreed to be named.

Judgment calls on the play-back

The hardest call is a theme about your principal. If eight people say decisions wait on the CEO, it goes in the read-out, delivered privately first and phrased as a pattern in the company. Your principal will learn from how you handle it whether you'll tell them hard things later.

The second call is who sees it. A principal who has never had a Chief of Staff should see it alone first. One who runs an open leadership team may want it presented to the room. When unsure, share the themes with the leadership team and keep the counts and principal-specific points for the 1:1. Within two weeks, send each person you met one line on what's happening with the theme they raised; if people stop telling you things in month two, someone thinks you broke a confidence.

Write the day-30 memo

End the month with a one-page memo, sent a day before your day-30 check-in, with your draft mandate attached. It covers what you've learned, the weakest responsibility, what you've taken on, what you propose to own next, and the decisions you need in writing, so the check-in can be spent on direction.

This week, open a document called "Day-30 memo" and add one line after every listening-tour conversation. By day 28 you'll have most of it written.

# Day 30: what I've learned and what I propose

To: [principal]  ·  From: [you]  ·  For our check-in on [date]

## What I've done
- Met [number] people across [teams]
- Took over: [first real task and its status]
- Small things done for leaders: [one line each]

## What I've learned (top themes)
1. [theme]: raised by [n] of [n] people. What it means for us: [one line]
2. [theme]: ...
3. [theme]: ...

## The weakest of the four
[Priorities / rhythm / communication / projects]: [two sentences on why, with one example]

## My draft mandate (one page, attached): what I propose to own from day 31
- [the meeting, process or project]
- [what success looks like by day 60]

## What I won't take on (and who should)
- [item]: [owner]

## Decisions I need from you
1. [decision], by [date]
2. [decision], by [date]

## What I'd like to discuss
- [one open question about direction, or about how we work together]

# Day 30: what I've learned and what I propose

To: Maria (CEO) · From: Sam · For our check-in on March 27

## What I've done
- Met 22 people across all seven teams
- Took over: the Q2 hiring plan; final numbers go to finance on April 3
- Small things done for leaders: a new forecast template for the VP of Sales; notes and follow-ups from the product offsite

## What I've learned (top themes)
1. Priorities: 15 of 22 people named a different top priority for the quarter. What it means for us: teams work toward their own leader's goal.
2. Rhythm: the Monday meeting came up 11 times, mostly as a status round where decisions get reopened. What it means for us: most decisions take two meetings.
3. Projects: the partner integration came up 9 times; sales and product each think the other owns it. What it means for us: our largest Q2 deal depends on it.

## The weakest of the four
Rhythm. The Monday meeting runs 90 minutes with no decision log, and the pricing change was decided twice in February.

## My draft mandate (one page, attached): what I propose to own from day 31
- The Monday leadership meeting: agenda, pre-reads, decision log, follow-ups
- By day 60: the meeting runs in 60 minutes, and fewer than 1 in 10 decisions are reopened

## What I won't take on (and who should)
- Office move: Head of People
- Vendor renewals: finance

## Decisions I need from you
1. One owner for the partner integration, by our check-in
2. OK to publish the three company priorities in one place, by April 1

## What I'd like to discuss
- How you'd like me to raise themes about you that come up in the tour

Days 31 to 60: how do you take ownership as a new Chief of Staff?

In month two, take over one part of the operating rhythm end to end, usually the leadership team meeting, and pick one metric you'll own. Your mandate should already be agreed: draft it in week 3, agree it in week 4. By day 60, people should know what you own.

The operating rhythm is the right first thing to own because it's visible, cross-functional and nobody else wants it. It's also what employers ask for most: operating cadence (OKRs, KPIs and operating rhythm) appears in 61% of the more than 1,800 Chief of Staff job postings in the Chief of Staff Network's 2026 Pathways Report, more than any other responsibility.

Own one meeting, properly

Pick one recurring meeting and run it properly for a month. Send the agenda two days ahead, with the decisions needed listed above the topics. Ask for pre-reads by a fixed time, keep a decision log visible to everyone, and send owners and dates within an hour. Our meetings guide has templates for each, and the Chief of Staff operating rhythm guide covers the wider system.

Before you change anything, talk to whoever ran the meeting before you, often the COO, a senior leader or your principal's EA. They lose something when you take it over, and they know which parts work. Keep their best habits and credit them in your first agenda.

Here's what the change can look like, as an illustration: a Monday leadership meeting at a 120-person company, nine leaders, 90 minutes, each giving an update in turn.

Which meeting to own, and how it goes wrong

Pick the meeting where the leadership team feels the pain most, as long as your principal doesn't love running it. Some CEOs treat the leadership meeting as theirs. If that's your principal, own the monthly metrics review or the planning check-in, and support the leadership meeting with the agenda and decision log.

Around week three, pre-reads stop arriving on time; send a reminder the day before and start the meeting with the pre-read anyway. Around week four, a leader reopens a logged decision with your principal privately; ask your principal to send it back to the meeting, once, in public. When someone says the old meeting was more useful, ask what they miss and keep that part. In a remote team, lean harder on the pre-read and the decision log, because the hallway becomes a direct message you'll never see.

Alongside the meeting, own one metric your principal watches that nobody owns today, such as time to a hiring decision or on-time board materials. Report it in your weekly update. It turns "the Chief of Staff helps" into something you can point to at day 90.

Agree the mandate and keep the weekly update going

If nobody wrote your role down, draft the mandate yourself in week 3, send it with your day-30 memo, and agree it in week 4. Without one, the role fills with travel, hiring logistics and the vendor nobody wants to call. With one, you can say no without it sounding personal: "That's not on my list. Shall we ask [principal] whether it should be?" Our guide to writing a Chief of Staff mandate has the one-page template and a four-week process.

From week two, send your principal a weekly update the day before your 1:1: decisions you need (each with your recommendation), what moved, what's coming, and one 1:1 topic. Ask for the decisions in writing before you meet, so the 1:1 has room for what's coming. My take: write the mandate yourself and let your principal edit it. Principals usually respond well to a draft they can mark up.

Days 61 to 90: how do you prove the Chief of Staff role is working?

In month three, deliver one piece of strategic work tied to your principal's top priority, decide what you'll stop doing, and run a day-90 review with your principal that agrees the next two quarters. By day 90, your principal should be able to say what the role changed, in one sentence.

Pick a project your principal cares about, that crosses at least two teams, and that can show a result inside six weeks: a pricing review, the next planning cycle, a reorganization proposal, a new board reporting pack. If your day-30 memo named the weakest of the four responsibilities, your project should sit inside it. Add one thing to stop: most companies carry an initiative everyone privately thinks is dead, and a short case to end it, with the owner's agreement, is often the most valuable work a new Chief of Staff can do.

Choosing the project: a worked example

Use three tests: your principal raises it unprompted, it crosses two teams, and it can show a result in six weeks. Then a fourth that new Chiefs of Staff forget: does someone already own it who will feel you took it? Here's an illustration from a Series B company after the day-30 memo.

1. A pricing review. The CEO mentions it weekly, and it touches sales, product and finance. But the VP of Sales considers pricing his, and six weeks is too short for a real answer. Skip it, or offer to run the analysis for him.
2. A new board reporting pack. The CEO mentions it before every board meeting, and finance and three functional leads feed it. Nobody owns it today, and the next board meeting is seven weeks away. It passes all four tests.
3. Ending a stalled internal tool project. Everyone privately thinks it's dead, but its sponsor is the CTO. That's the stop item, and it goes forward as a short case the CTO agrees to before the CEO sees it.

She picks the board pack as the build and the tool as the stop. At a seed or Series A company, pick a four-week project instead. At a large company, co-own the project with the leader whose org it sits in and let them present the result. If your principal is a functional leader, pick a project inside their function that moves a company goal.

Decide what you'll stop doing

By day 90, list the work you've picked up that belongs to another team, and agree a handoff date for each item.

List everything you do in a typical week, mark each item keep, hand off or stop, and name an owner for everything you hand off. Then agree the list with your principal. Tristan Lim, one of our podcast hosts, wrote about the conversation every Chief of Staff needs to have with themselves: what you want from the role, separate from what the company needs from you.

This week, write your keep, hand off, stop list. It takes 20 minutes and you'll be surprised what's on it.

Run the day-90 review

Send a short written review a day ahead, then meet. Cover what changed because of the role, the rhythm, what you've stopped or handed off, the strategic project, the metric you own, and goals for the next two quarters. Then raise the question most Chiefs of Staff leave for year two: how long is this tour likely to be, and what comes next for you?

Raise it now, because the tour is short. The median completed Chief of Staff stint is 20 months, and the middle half run 12 to 30 months, according to our 2026 Pathways Report (more than 2,100 moves). Those who leave inside a year are the least likely to step up, and my read is that many of those early exits start with a role nobody defined.

Staying pays when there's a path: 61% of Chiefs of Staff step up when they stay at the same company, against 48% when they leave, and about 8% of completed stints end with a bigger Chief of Staff title in the same company. The day-90 review is where you invite your principal to start thinking about your next role.

# Day 90: review of the Chief of Staff role

To: [principal]  ·  From: [you]  ·  For our review on [date]

## What changed because of the role
- [one line each, with evidence]

## The rhythm
- What I run: [meeting or process]. What's better: [one line]. What isn't yet: [one line]

## Stopped or handed off
- [item]: [new owner or stopped]

## Strategic project
- [project]: result, and what's next

## The metric I own
- [metric]: where it was on day 30, where it is now, target next quarter

## Next two quarters
1. [goal]
2. [goal]

## The role and me
- Expected length of this tour: [your view]
- What I'd like to be doing in 12 to 24 months, and what you'd need to see from me to support it

# Day 90: review of the Chief of Staff role

To: Maria (CEO) · From: Sam · For our review on June 26

## What changed because of the role
- The Monday meeting runs in 60 minutes; 2 of 31 logged decisions reopened since April
- The partner integration has one owner, the VP of Product, and shipped on May 30

## The rhythm
- What I run: the Monday leadership meeting. What's better: decisions stick and follow-ups go out within the hour. What isn't yet: about half the pre-reads arrive late

## Stopped or handed off
- Internal reporting tool: stopped, with the CTO's agreement
- Hiring logistics: handed to the recruiting coordinator

## Strategic project
- New board reporting pack: used at the June board meeting. From Q3, finance owns the numbers and I own the narrative

## The metric I own
- Board materials on time: 2 days late on day 30, 3 days early in June, target 5 days early in Q3

## Next two quarters
1. Run the H2 planning cycle and close it by August 14
2. Take over the monthly metrics review from finance

## The role and me
- Expected length of this tour: two to three years
- In 12 to 24 months I'd like to lead operations. To support it, you'd need to see me close H2 planning on time without you chasing it

Share a version with the leadership team as well: what you run, what you've stopped, and what's next. It keeps the role visible beyond your principal.

What are the most common traps in a Chief of Staff's first 90 days?

The common traps are becoming the person who catches everything nobody else owns, being told off for overstepping and then for not owning enough, letting your 1:1 turn into a weekly fire drill, being useful but invisible, and running yourself into the ground. Most come from a role nobody defined clearly enough, early enough.

Our older post on the chief of stuff argues that breadth is the job; breadth with no written edges turns into a pile of other teams' favors. The second trap can happen in the same week, because your principal hasn't said where the line is. Ask once, "When someone brings me something outside my list, do you want me to own it, route it, or ask you?", and write the answer into your mandate.

When two leaders pull you in opposite directions

Don't pick a side in the hallway. Write both positions down, check each leader agrees you've described theirs fairly, and bring them to your principal with your recommendation and the trade-off. Leaders will also test whether you'll carry gossip upward; decline politely and consistently.

If your principal is another executive

Only 44% of Chief of Staff postings that name a principal say CEO, founder or president, according to the Chief of Staff Network's 2026 Pathways Report (more than 700 postings that name a principal). If you support a CTO, COO or business unit leader, add your principal's peers to the listening tour early, and tie your mandate to company goals as well as your principal's, so the role is easy to defend.

If your principal has never had a Chief of Staff, or you're replacing one

A principal new to the role means you define it yourself: make the pre-start conversation longer and treat the week 3 mandate draft as the most important document of the quarter. If your principal won't have that conversation at all, take it seriously. If you're the second Chief of Staff in the seat, read your predecessor's notes and ask what they'd stop doing, then run your own tour and agree your own mandate.

If you're remote, run the tour on video with the same four questions and send the read-out in writing. One in-person week with the leadership team in month one does more for trust than a quarter of video calls.

How do you know your first 90 days as a Chief of Staff worked?

Your first 90 days worked if leaders bring you problems without being asked, the part of the rhythm you own runs without your principal chasing it, and your principal sends you to at least one meeting in their place. If you can say in one sentence what the role changed, and your principal would say the same sentence, you're on track.

Hours worked and tasks closed tell you little, because every new Chief of Staff is busy. Look for trust and reach: is your principal spending less time on what you took over, are fewer decisions reopened after the leadership meeting, and does bad news reach your principal faster? The sharpest test is whether your principal would send you to a strategy meeting they can't attend. If the answer at day 90 is no, ask what they'd need to see, and put it in your goals.

To build your own plan, fill in your details and paste the prompt below into the AI assistant you use.

I'm starting (or just started) as a Chief of Staff. Help me build a practical 90-day plan.

My context:
- Company: [stage, size, industry, remote or in person]
- My principal: [title], has had a Chief of Staff before: [yes/no]
- What my principal wants off their plate first: [answer]
- Biggest problems I've heard so far: [list]
- My background and strengths: [list]
- Days into the role: [number]

Use this structure:
1. Before day one and week one: the first real task to take over, and who to meet first
2. Days 1 to 30: listening tour plan (who, in what order, 4 questions), and how to map the four core responsibilities
   (priorities and decisions, operating rhythm, communication, cross-functional projects) for my company
3. Days 31 to 60: which meeting or process I should own first and why, one metric to own, and how to agree my mandate
4. Days 61 to 90: one strategic project tied to my principal's top priority, and what I should stop doing
5. The 5 signals that will tell me at day 90 whether it's working

Be specific to my context. Push back if anything in my plan sounds like scope creep or busywork.

If the signals are mostly missing, go back to the mandate. Our guide to Chief of Staff skills has a self-assessment you can run with your principal. Then plan the next quarter the same way: one part of the rhythm to improve, one strategic project, one thing to stop, and the day-180 check-in booked before you leave the day-90 review.