Board Prep

/em:board-prep — Board Meeting Preparation

Command: /em:board-prep <agenda>

Prepare for the adversarial version of your board, not the friendly one. Every hard question they'll ask. Every number you need cold. The narrative that acknowledges weakness without losing the room.

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The Reality of Board Meetings

Your board members have seen 50+ companies. They've watched founders flinch at their own numbers, spin bad news as "learning opportunities," and present sanitized decks that hide what's actually happening.

They know when you're not being straight with them. The question isn't whether they'll ask the hard questions — it's whether you're ready for them.

The best board meetings aren't the ones where everything looks good. They're the ones where the CEO demonstrates they see reality clearly, have a plan, and can execute under pressure.

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The Preparation Framework

Phase 1: Numbers Cold

Before the meeting, every number in your deck should live in your head, not just the slide.

The numbers you must know without looking:

• Current MRR / ARR and month-over-month growth rate
• Burn rate (monthly) and runway (months at current burn)
• Headcount by department
• CAC and LTV by channel / segment
• Net Revenue Retention
• Pipeline: value, conversion rate, average sales cycle
• Churn: rate, top reasons, top churned accounts
• Gross margin (product), net margin (company)
• Key hiring positions open and time-to-fill

Stress test yourself: Can you answer "what's your burn?" without hesitation? "What's your churn rate by segment?" If you pause, you don't know it.

Phase 2: Anticipate the Hard Questions

For every item on the agenda, generate the adversarial version of the question.

Standard adversarial questions by topic:

Revenue performance:

• "You missed revenue by 20% this quarter. What specifically failed?"
• "Is this a pipeline problem, a conversion problem, or a capacity problem?"
• "If you missed because of one big deal, how dependent is your model on individual deals?"
• "When do you project recovery and what are the leading indicators you're right?"

Runway / burn:

• "At current burn you have N months. What's your plan if the next round takes 9 months?"
• "What would you cut first if you had to extend runway by 6 months today?"
• "Is there a scenario where you don't raise another round?"

Product / roadmap:

• "You shipped X. What did customers actually do with it?"
• "What did you kill this quarter and why?"
• "Where are you behind on roadmap? What's slipping?"

Team:

• "Who's at risk of leaving? How would that affect execution?"
• "You've had 3 VP-level hires not work out. What pattern do you see?"
• "Is the team the right team for this stage?"

Competition:

• "Competitor Y just raised $50M. How does that change your position?"
• "If they copy your best feature in 90 days, what's your moat?"

Phase 3: Build the Narrative

The board meeting isn't a status update. It's a leadership demonstration.

The structure that works:

1. Where we are (honest) — Current state of business, the real number, not the smoothed one
2. What we learned — What the data is telling us that we didn't know 90 days ago
3. What we got wrong — Name it directly. Don't make them ask.
4. What we're doing about it — Specific, dated, owned actions
5. What we need from this room — Concrete ask. Not "support" — specific introductions, decisions, resources.

The rule on bad news: Never let the board be surprised. If a quarter went badly, they should know before the deck. A 5-sentence email 3 days before: "Revenue came in at $X vs $Y target. Here's what happened, here's what I'm doing, here's what I need from you."