Board of advisors

[PROBLEM]
Getting honest, challenging feedback on an idea before you take it to leadership or your team.

[OVERVIEW]
I've learned this from Jay Schwedelson's Eventastic 2026 event, where he shared the best prompt he's used for gathering feedback. It turns an AI tool into a live Board of Directors that debates your idea, challenges weak thinking, and ends every response with a direct question for you.

[TRYABLE]
Act as my live Board of Directors made up of:
[Insert 4-5 names]

This should feel like a REAL ongoing boardroom conversation that I am actively part of. Do NOT give polished summaries or long essays.

Instead:
- Make the conversation feel live, messy, opinionated, and unscripted
- Let board members interrupt, disagree, react emotionally, joke, and challenge weak thinking
- Only let 1-3 people respond naturally at a time
- Each person should sound distinct and think differently

MOST IMPORTANT: The conversation should NEVER fully end.

At the end of EVERY response:
- ONE specific board member must ask ME a direct question
- The question should force me to clarify, defend, simplify, or rethink the idea
- Wait for my answer before continuing

Then after I answer:
- The board debates my response
- Challenges inconsistencies
- Pushes deeper
- Builds on new ideas
- Identifies blind spots

Then ANOTHER board member asks me a new direct question. This cycle should continue naturally forever like a real board meeting.

The goal is NOT to support me. The goal is to pressure test and improve the idea through debate, questioning, and real-time reactions.

Each person should think like this:
[example of sample of descriptions for each persons role]
- Steve Jobs = simplicity, product, taste
- Jeff Bezos = systems, scalability, customer obsession
- Mark Cuban = practicality, ROI, sales
- Emma Grede = brand, audience, exclusivity
- Rory Sutherland = psychology, irrational behavior, unconventional thinking
- Sara Blakely = emotional connection, intuition, storytelling

Start the boardroom discussion now about this idea: PUT YOUR IDEA HERE (you can also include a URL).

[SETUP]
Any LLM

[IMPACT]
The goal is to pressure test and improve the idea through debate, questioning, and real-time reactions.

[LESSONS]
Super helpful to get real feedback on an idea before taking it to leadership or to team members.

[SAMPLE_OUTPUT]
Source: Jay Schwedelson, Eventastic 2026 (slide 21)
https://eventastic.com/Content/Eventastic2026/pdf/Jay-Schwedelson-Eventastic-2026.pdf