One on one prep

1:1 prep

A good 1:1 is about the other person, picks up exactly where the last one left off, and ends with clear commitments on both sides. This kit keeps one notes file per person and builds a one-screen prep from it.

Files

One file per person in one-on-ones/, named by role or first name, for example one-on-ones/head-of-marketing.md. Newest entry at the top under the header. Format (see examples/head-of-marketing.md):

# 1:1 notes: Head of Marketing

Cadence: weekly, Tuesdays, 30 minutes
Goals this quarter: 1) ... 2) ... 3) ...

## 2026-10-28
- Mood: ...
- They own: <task> by <date>.
- I owe: <task>.
- Career: ...

If no file exists, ask for: their role, cadence, their top three goals this quarter, and anything open from the last conversation. Create the file.

Prep steps

1. Read the file. Focus on the last two entries and the quarter goals.
2. List open commitments, both ways. Every "They own" and "I owe" line not marked done. Put overdue ones first with the date. Lead with what the user owes; showing up having done your part sets the tone.
3. Ask what changed this week if the user has not said: wins, fires, metrics, anything from the ELT brief or team updates that touches this person. One question, then move on with what you have.

4. Pick three questions, specific to this person, at most one about status. Good shapes:

   • Progress on a goal: "Webinar launch is in two weeks. What would make you nervous about it?"
   • Blockers: "What is slowing you down that I could remove?"
   • Growth: tie back to the last Career line. "You wanted board exposure. Want to own the marketing slide this quarter?"
   • Feedback for the user: "What is one thing I could do differently for you?"
5. Flag patterns across entries, gently: the same blocker three weeks running, mood trending down, a goal with no progress for a month. Suggest how to raise it, never a diagnosis.
6. Show the prep (format below). Keep it to one screen.

After the 1:1

When the user shares what happened, add a dated entry at the top: mood in a few words, key points, They own: and I owe: lines with dates, and any Career note. Mark finished commitments from earlier entries (done 2026-11-04). Read the new entry back in two lines.

Output format

## 1:1 prep: Head of Marketing, Tue 2026-11-04

**You owe them:** intro to a peer COO (from 10-28), approve the $5k budget move (from 10-28)
**They owe you:** webinar speaker list (due 10-31, overdue), Q1 plan outline (due 11-07)
**Since last time:** <two lines>

**Ask:**
1. ...
2. ...
3. ...

**Watch:** <one pattern, if any>

Guardrails

• These notes are private to the user. Keep them in one-on-ones/, and never copy them into team-wide docs, briefs, or channels.
• Write facts and what was said, not judgments about character. No guesses about health, family, or personal life.
• For performance concerns, compensation, or anything that may need HR, suggest the user talk to their HR partner, and note only the facts and dates.
• Never send messages to the person on the user's behalf.

1:1 prep

Builds a one-screen prep for your next 1:1 from your running notes on that person: what you owe them, what they owe you, what changed, and three questions worth asking. After the meeting, it files your notes so next week starts where this one ended.

Who it is for

Founders, COOs, and managers with several direct reports who want every 1:1 to feel prepared without spending 20 minutes on each.

Example

Input: examples/head-of-marketing.md, a running notes file with entries from the last two 1:1s.

Ask: "Prep my 1:1 with the Head of Marketing."

Output:

## 1:1 prep: Head of Marketing, Tue 2026-11-04

**You owe them:** intro to a peer COO who ran a webinar program, approve the $5k budget move
**They owe you:** webinar speaker list (due 10-31, overdue), Q1 plan outline (due 11-07)

**Ask:**
1. Webinar launch is close. What would make you nervous about it?
2. Content lead finals were last week. Who are you leaning toward, and why?
3. You wanted board exposure. Want to own the marketing slide this quarter?

**Watch:** "stretched" two weeks running. Ask what you could take off their plate.

What it can access

• Reads and writes notes files in one-on-ones/ (and reads the sample in examples/).
• No scripts, no network, no API keys. Works in Claude Code, Codex, and Cursor.

Setup

None. Create one-on-ones/ or let the kit create a file the first time you prep for someone.