Quick 5-Person Advisory Board

What You Get

Five distinct expert perspectives on any business question. Like having a board meeting without the board.

The Prompt

I need a 5-person advisory board to help me think through a business decision.

My business: [what you do]
The decision or question: [what you're trying to figure out]
Context: [relevant background — revenue, team size, timeline, constraints]

Create 5 advisors with different perspectives:

1. THE OPERATOR — Someone who's built and scaled a similar business. Focused on execution and systems.
2. THE STRATEGIST — A big-picture thinker. Focused on positioning, market dynamics, and long-term plays.
3. THE CUSTOMER — An ideal customer. Focused on what they actually want and would pay for.
4. THE SKEPTIC — A critical thinker. Pokes holes, asks hard questions, flags risks.
5. THE CREATIVE — An unconventional thinker. Brings ideas from outside the industry.

For each advisor:
- Give them a name and one-line bio
- Have them give their honest take on my question (3-5 sentences)
- Have them ask me one follow-up question

End with a SYNTHESIS section that identifies:
- Where the advisors agree
- Where they disagree
- The top 3 things I should think about before deciding

How to Use the Board

This works best as a conversation. After the initial round:

I want to go deeper with [advisor name]. My answer to their question is: [your answer]. Have them respond and push my thinking further.

Or run a debate:

The Operator and the Skeptic disagree on [topic]. Have them debate it. 3 rounds each. Keep it specific to my situation.

When to Use This

• Before a big pricing change
• When deciding whether to launch a new offer
• Before hiring or making a major investment
• When you’re stuck between two directions
• Quarterly planning sessions

Tips

• The more context you give, the better the advice. Include numbers. Include what you’ve already tried.
• Swap out advisor roles to match your question. Building a product? Add “The Engineer.” Raising money? Add “The Investor.”
• Save the synthesis section. Come back to it after a week. Distance gives clarity.
• This doesn’t replace real advisors. But it’s a great way to stress-test your thinking before you talk to them.

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