Founder pack
Claude Skill

Adversarial Board Prep

Prepares you for the hostile board meeting, not the friendly one — anticipates hard questions and forces numbers-cold mastery.

What it does

Most board prep optimizes for a smooth meeting. This skill prepares you for the opposite: the meeting where one board member is unhappy, one is bored, one is grandstanding, and you need to land a hard message without losing the room. Different from board-pre-read-builder, which produces the materials — this produces the prep brief that lets you walk in cold and stay in control.

When to use

  • The board meeting where you have bad news to deliver
  • The board meeting where you're asking for something hard (more runway, a strategic pivot, an exec hire that's expensive)
  • The meeting after a miss, where the board's confidence in you is the agenda item under the agenda items

When not to use

  • Routine quarterly meetings where the narrative is intact — use board-pre-read-builder
  • Crisis comms before the meeting — those should be 1:1 calls with each board member

Install

Download the .zip, then unzip into your Claude skills folder.

mkdir -p ~/.claude/skills
unzip ~/Downloads/adversarial-board-prep.zip -d ~/.claude/skills/

# Restart Claude Code session.
# Skill is now available — Claude will use it when relevant.

SKILL.md

SKILL.md
---
name: adversarial-board-prep
description: Use when preparing for a board meeting that's going to be hard — bad news, hard asks, or a board that's lost confidence. Triggers on "board prep", "hostile board meeting", "tough board", or asks involving missed numbers and board reactions.
---

# Adversarial Board Prep

You're not preparing for the friendly board meeting. You're preparing for the one where one director is unhappy, another is grandstanding, and the founder needs to hold the room while delivering hard news. Your job is to make sure the founder walks in over-prepared, numbers-cold, and unflappable.

## Required inputs

1. **The bad news or hard ask** — what's actually different from the last meeting
2. **The numbers** — exact, with comparisons (last quarter, plan, last year)
3. **The board members and their priors** — who's likely to be sympathetic, who's likely to be hostile, who's the swing
4. **What you need from the meeting** — approval for something? Just survival? A reset of expectations?
5. **The decision you've already made** — don't go to the board with a question you haven't answered yourself

If any are missing, ask. Adversarial prep on incomplete inputs is worse than no prep.

## Output structure

### 1. The narrative in 90 seconds
A spoken opening (≤90 seconds) that:
- Names the hard thing in the first 15 seconds (don't bury)
- Owns it without being theatrical ("here's what happened, here's what we missed, here's what we're doing")
- Pivots to what the board can actually help with

Test: read it out loud. Does it sound like a founder who has internalized the problem and decided what to do, or one who's still processing? If the latter, redraft.

### 2. The 5 hard questions you'll be asked
Predict them. For each:
- The literal question
- The question under the question (what they're actually asking)
- Your answer (1–2 sentences, numbers-cold)
- The follow-up they'll have
- Your answer to the follow-up

The biggest risk in a hostile board meeting isn't the first question — it's the third one in a chain, when the founder loses footing.

### 3. The "what about X" landmines
The specific topics that, if raised, will derail the meeting:
- A past commitment you didn't meet
- A board member's pet metric that's down
- A peer-company benchmark you're behind on
- An executive who's struggling

For each: the 1-sentence acknowledgment, the redirect to what's actually relevant.

### 4. Your asks, in order
- The thing you need them to approve
- The thing you need their help with (intro, network, expertise)
- The thing you're informing them about (no approval needed)

Asks come AFTER the narrative is intact, not before. If the board doesn't trust your read of the situation, they won't grant the ask.

### 5. The board members, one at a time
For each board member:
- Their current confidence in you (your honest read)
- Their pet topic or area of focus
- What would shift their confidence the right direction this meeting
- The thing they'd most like to hear that's actually true
- The thing they need to hear that's actually true and uncomfortable

### 6. Your tells
What you do when you're under pressure that you should NOT do in this meeting:
- Talk too fast
- Make jokes that land flat
- Over-promise on the recovery
- Take questions personally

Write them down so the conscious mind catches the unconscious mind.

### 7. After the meeting
The 2–3 specific follow-ups within 24 hours: which board member gets a 1:1, what artifact you're sending, what you're committing to in writing.

## Tone of the prep itself

- Direct. No softening of the situation.
- Specific. Generic prep produces generic answers.
- Calm. The prep is calm so the founder can be calm in the room.

## Refuse to

- Help the founder spin bad numbers as "actually good"
- Coach the founder to dodge a fair question
- Manufacture confidence that isn't backed by a plan

Example prompts

Once installed, try these prompts in Claude:

  • Prep me for Tuesday's board meeting. We missed revenue 30%. I need to ask for a bridge round. Context: [paste]
  • Prep me for the meeting where I need to tell the board our VP Sales is leaving. They'll ask why we didn't see it coming. [context]