Founder 1:1 Prep

---
name: founder-1-1-prep
description: Use when prepping for founder 1:1s with direct reports. Triggers on "prep my 1:1", "1:1 with my report", "questions for VP X", "what should I ask in 1:1".
---

# Founder 1:1 Prep

Founder 1:1s with execs and senior reports are the highest-leverage 30 minutes in the company — and the most commonly wasted. They drift to status because that's what's easy, while the actual high-value conversations (the ones the report is avoiding, or the ones the founder is avoiding) never happen.

This skill builds prep that surfaces the conversations you should be having, not the ones you'll naturally have.

## Required inputs

For each report:

1. **Their role and tenure** — VP Eng (2 years), Head of Marketing (2 weeks), etc.
2. **Recent context** — what they shipped, missed, are working on
3. **Current state read** — energized / stretched / stuck / quiet
4. **Last 1:1 takeaways** — what was unresolved
5. **Decisions YOU need to land** with them this 1:1
6. **What you've been avoiding** with this person, if anything

If the answer to "current state" is "I don't know" — that's the prep work. The 1:1 should be largely about finding out.

## Output structure (per report)

```
# 1:1 Prep: [Report name, role]

## Read on this person right now
2-3 sentences. Where's their head. What are they probably avoiding.

## Their topics they'll likely raise
- Anticipate 2-3 things they'll bring up

## My questions (3-5, specific to this person)
- Order from broad to specific
- Each one has a "what to listen for" note

## What I need to land this 1:1
- Decisions I need their input on
- Feedback I owe them
- Things I'm avoiding that I should bring up

## Watch-fors
- Signals that things are off (avoidance, energy drop, escalation patterns)
- The thing this person tends to NOT say
```

## Question patterns (rotate, don't ask same questions every time)

### State check
- "What's your energy at right now, 1-10?"
- "What's been most frustrating this week?"
- "What's the biggest thing on your plate I might not have full context on?"

### Working relationships
- "Where is your team's ability to execute getting blocked?"
- "Who on the leadership team are you not getting enough from?"
- "Where do you wish I were more involved? Less involved?"

### Career / growth
- "What part of your role has felt most energizing this month?"
- "What part has felt off?"
- "What would make this the role you stay in for 3 more years?"

### Their team
- "Who on your team are you most worried about right now?"
- "Who's exceeding expectations I should know about?"
- "What hire would have the biggest impact next quarter?"

### Strategy / company-level
- "What are we doing as a company that you wouldn't be doing if it were your call?"
- "What's the dumbest thing in our process right now?"
- "Where do you think we're underinvested?"

## Listen for (what to watch in their answers)

- **Avoidance patterns**: same person/issue keeps surfacing but never gets resolved
- **Energy mismatch**: their words say "fine" but tone says otherwise
- **Concrete-to-abstract drift**: when they shift from specifics to generic statements, that's where the discomfort lives
- **What they DON'T mention**: a head of sales not bringing up their pipeline at all is a signal

## Owe-them list

Track per-person what you owe:
- Feedback you've meant to give
- Decisions you've been deferring
- Resources / hires / approvals they're waiting on
- Context from leadership / board they don't have

If you walk out of a 1:1 still owing them something, you delayed your own work.

## Anti-patterns

- Asking the same 3 questions every week — they'll start prepping rehearsed answers
- "How are things going?" — opening question that produces nothing
- Letting status fill the 30 minutes — async the status, save the live time for the harder conversations
- Avoiding the hard topic for 6 weeks in a row — the longer you wait, the harder it gets
- Treating all reports the same — VP Eng, Head of Marketing, and Head of Sales need different conversations
- Rushing the close — last 5 minutes is where the real thing often surfaces; build in space

## Tone

- Curious, not interrogating
- Specific to this person — not template questions
- Honest about your own state — if you're stretched, say so; reports model your transparency

## Output format

For each report: a 1/2-page prep card. Print or open before the 1:1. End each card with the **1 thing I must NOT leave this meeting without addressing** — bolded.