The Chief of Staff 30-60-90 day plan you can actually work from
An interactive first-90-days plan for a new Chief of Staff or exec-ops hire. Check items off as you go, write your own context into the fields, and print a clean copy for the review with your principal. Your progress saves in your browser. Free, no signup.
What this plan gives you
Most 30-60-90 templates are an empty grid with three columns. This one is filled in for the specific job of being a Chief of Staff: the listening tour, the principal, the first system you ship, and the readout that ends the quarter. It's a live checklist with roughly fifty items and eight fields for your own notes, a progress bar so you can see how far through you are, and a print button that turns the whole thing into a clean document you can hand to your principal.
Everything you check and everything you type is stored in your own browser only. Nothing is sent anywhere, and there's no account. If you clear your browser data or switch devices, the plan resets, so print or copy it out when it matters.
The four phases
- Before day one. Groundwork you can do with offer-signed access: the last two quarters of board decks, the leadership team's notes, the org chart, and the five to eight people your principal wants you to meet first. One field to capture, verbatim, what your principal says success looks like at 90 days.
- Days 1 to 30, listen and stabilize. Week-by-week focus, a listening tour of twelve to twenty conversations using the same five questions with everyone so patterns surface, five questions to answer about your principal, and three artifacts to produce: a stakeholder map, a map of the meeting and decision cadence, and a 30-day readout.
- Days 31 to 60, build and prove. Pick one system to ship, not four. The tool gives you four candidates (fix the leadership meeting, stand up a decision log, install a weekly priorities brief, or build a clean view of company goals), a field to name your choice, a week-by-week build-pilot-adjust-deliver rhythm, and the watch-outs that sink new operators.
- Days 61 to 90, own and scale. Formalize your remit in writing, harden the system so it survives without you babysitting it, run one full cycle end to end, and deliver a five-part 90-day readout.
How to use it
Each phase has an alignment field at the top. Fill it in with your principal, not alone: what the two of you agree this phase has to produce. That single habit is what separates a plan that gets you promoted from a plan that gets ignored, because the failure mode in this role isn't laziness, it's working hard on the wrong thing.
Then use the milestones at the end of each phase as an honest gate. If you can't check "your principal has handed you at least one recurring responsibility" by day 30, don't roll straight into building a system. Go back and find out why.
The plan is a default, not a prescription. A Chief of Staff at a twenty-person seed startup and a Chief of Staff to a public-company CEO will spend their first month very differently. Delete what doesn't apply. What generalizes is the shape: listen before you change anything, ship one visible thing, then formalize what you own.
Questions people ask
What should a Chief of Staff do in the first 30 days?
Listen, map, and take one or two low-risk things off your principal's plate. Concretely: run twelve to twenty stakeholder conversations with the same core questions, learn how decisions actually get made rather than how the org chart says they do, and finish with a written 30-day readout that names what you heard and the two or three problems worth solving. Resist the urge to change anything structural in month one.
What is a 30-60-90 day plan for a Chief of Staff?
Three phases with different jobs. Days 1 to 30 are for understanding the organization and building trust. Days 31 to 60 are for shipping one system that makes something visibly better. Days 61 to 90 are for formalizing your remit and setting up how the next quarter runs. The mistake most new Chiefs of Staff make is compressing all three into month one.
What should I build first as a new Chief of Staff?
One thing, visible enough to matter and small enough to finish. The four that most reliably work: fixing the leadership team meeting, standing up a decision log or single source of truth, installing a weekly priorities brief that flows up to your principal, or building a clean current view of company goals. Read the decision log guide before you pick.
What questions should I ask on the listening tour?
Use the same five with everyone, so you can spot patterns instead of collecting anecdotes. What's working that we should protect. What's the most frustrating recurring problem. Where do decisions get stuck. What does the principal do that helps you most, and what gets in your way. If you had my role, what would you fix first.
Does my progress save?
In your browser, yes. Your checks and notes are written to that browser's local storage and will still be there next time you open the page on the same device. They are not sent to us or stored on a server. Use the print button to keep a permanent copy.
Keep going
The written deep-dive behind this plan, plus the two skills that decide whether month two lands: running the leadership meeting and moving work without formal authority.