WEEK 4 · THINK BIGGER · 10 min

The Brief Only You Get

Your job is to see what's changing before the room does. So build the brief a great chief of staff would hand you.

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Not your to-do list. The questions you're sitting with — about market, talent, product, capital, positioning. The ones that matter for the next 90 days.

Sources can be Substacks, podcasts, newsletters, analyst feeds, a competitor's blog — whatever you'd actually read if you had two uninterrupted hours.

COPY THIS PROMPT

Here are my three biggest strategic questions right now:

1. [question 1]
2. [question 2]
3. [question 3]

Here's my calendar this week:
[paste calendar or describe the key meetings]

Here are 2–3 sources I trust:
[paste links or names]

Give me a one-page brief on what moved in my world this week, organized around these three questions. For each question:
- The one or two developments that matter most
- Why they matter for my specific situation
- What I should think about before my meetings this week

Then add a section titled "Flagged: don't get caught not knowing this." Two or three items I'd be embarrassed not to know in my next meeting. Be blunt about what's still uncertain.

Sample output · Your weekly brief

Your Weekly Brief

Prepared for you · 4 min read

Question 1

Pricing strategy heading into Q3

•A direct comp announced tiered pricing this week; their old flat plan is now gone — your sales team will be asked about it.

•Two analysts published "fair price" frameworks for your category. One puts you 12% under, one puts you 8% over.

Question 2

Senior ops hire

•Three peer companies posted similar roles in the last 10 days. Talent supply is tightening fast.

•One referral candidate just left their seat. ~2–3 week window before they're picked up.

Question 3

Customer retention narrative

•New industry benchmark dropped: median net retention in your segment is now 108%. You'll be asked this on the next board call.

•Two of your top accounts cited the same friction in support tickets this month. Worth a direct call.

⚑ Flagged — don't get caught not knowing this

The category median NRR moved to 108% this quarter. If you quote 105% on the board call Thursday, expect pushback.

That gap is the entire point. The brief isn't to tell you you're informed — it's to surface the things you would have missed.

TODAY'S INSIGHT

The leaders who see around corners aren't smarter. They've just built a system that brings them the brief before the room walks in.

COMING NEXT

Continue to Day 18: Think On Paper →