The Exec Ops Brief

Your First 90 Days plan.

A working 30/60/90 plan for a new Chief of Staff. Check items off as you go, capture your own context in the fields, and print a clean copy for your week-one review with your principal. Your progress saves in this browser.

PREP

Before day one

If you have any offer-signed access

Groundwork

Read the last two quarters of board decks, all-hands decks, and any strategy or planning docs. Read the last three months of the leadership team's meeting notes, if they exist. Skim the org chart. Note who reports to your principal and who the informal power holders are. Ask your principal for a list of the 5 to 8 people you should meet first, and why. Ask your principal: "What does success in this role look like to you at 90 days?" Write the answer down verbatim.

Principal's stated 90-day success

DAYS 1-30

Listen, map, and stabilize

Phase 1

Phase goalUnderstand how the organization actually operates, build relationships, and take one or two low-risk things off your principal's plate.

Principal alignment (confirm in week 1)

Focus by week

Week 1Onboarding logistics, access, and your principal's operating rhythm. Sit in on every meeting you can as an observer. Week 2Listening tour begins. Start the stakeholder interviews. Week 3Continue interviews. Begin mapping the meeting and decision cadence. Week 4Synthesize. Deliver your "first 30 days" readout to your principal.

Listening tour (aim for 12 to 20 conversations)

Use the same core questions with everyone so you can spot patterns.

What is working well right now that we should protect?
What is the most frustrating recurring problem you deal with?
Where do decisions get stuck?
What does your principal do that helps you most? What gets in your way?
If you had my role, what is the first thing you would fix?

Track each conversation in your own doc: person, role, date, top theme, follow-up owed.

Understand your principal

How do they prefer to receive information: written brief, live conversation, or a mix? What are their non-negotiables and pet peeves? What are they avoiding right now that they know they should deal with? How do they want to be interrupted in an emergency? What decisions do they want to keep, and what are they willing to delegate to you?

Artifacts to produce by day 30

A written stakeholder map with themes and tensions. A current-state map of the leadership meeting and decision cadence. A short "first 30 days" readout: what you heard, three problems worth solving, and what you propose next.

Day 30 milestones

You can describe how the top-level operating cadence works without looking it up. Your principal has handed you at least one recurring responsibility. You have named the two or three problems to focus on next, and your principal agrees.

DAYS 31-60

Build and prove

Phase 2

Phase goalPut your first system in place and show early, concrete value. Pick something visible enough to matter and small enough to finish.

Principal alignment (confirm at day 30)

Choose your first build (don't attempt all)

Fix the leadership team meeting: agenda, pre-reads, decisions captured, follow-ups tracked. Stand up a decision log or single source of truth. Install a weekly priorities brief that flows up to your principal. Create a clean, current view of the top company goals and their status.

My first build

Weekly focus

Week 5Design the system. Write down what "good" looks like and who it serves. Week 6Pilot it with the leadership team or your principal. Gather reactions. Week 7Adjust based on real use. Remove anything that added friction without value. Week 8Deliver your "first 60 days" readout with evidence the system is working.

Watch-outs

Don't reorganize things people rely on without explaining why.
Don't confuse activity with progress. One system that sticks beats five that people quietly ignore.
Keep your principal informed before the leadership team hears about a change, not after.

Day 60 milestones

One system you built is in active use, not just designed. At least one leadership team member has told you, unprompted, that something got easier. You are trusted to run at least one meeting or process on your principal's behalf.

DAYS 61-90

Own and scale

Phase 3

Phase goalMove from proving yourself to running a defined part of the operating system. Set up how the next quarter will work and where you fit.

Principal alignment (confirm at day 60)

Focus

Formalize your remit. Write down what you own, what you support, and what stays with your principal. Extend or harden the system you built so it survives without you babysitting it. Take ownership of one full cycle, for example run the quarterly planning prep end to end. Identify the next two problems worth solving in the coming quarter.

Weekly focus

Week 9Draft your remit doc. Review it with your principal. Week 10Lead a full process cycle without your principal in the driver's seat. Week 11Document the systems you built so they are transferable. Week 12Deliver your 90-day readout and propose your priorities for the next quarter.

The 90-day readout (deliver to your principal)

What I learned about how we operate.
What I built and the evidence it is working.
Where I now own the work, and where I still support.
The two or three things I recommend we tackle next quarter.
What I need from you to be more effective.

Day 90 milestones

Your remit is written down and agreed. A leadership process runs on you without your principal stepping in. Your principal can point to specific things that improved because you were there. You and your principal agree on the priorities for the next 90 days.

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