Stop Letting AI Just Agree With You: The “Run It By The Board” Prompt

You know when you’re having a conversation with AI, whether that’s ChatGPT, Claude, or anything else, and you just find it responding to you overly positively? Reinforcing your own beliefs, nodding along to your decisions, when what you actually want is for it to act like a group of experts. To qualify what got you to the decision. To really challenge you. To improve the outcome.

That positive reinforcement loop is one of the biggest traps of working with AI. It feels great in the moment. You feel smart. You feel validated. But you walk away with a worse decision than you came in with, because nothing got stress tested.

So I’ve come up with something to fix it.

Meet The Board

I call it the Run It By The Board prompt. The idea is simple: instead of bouncing your decision off a single AI voice that tends to agree with you, you sit it in front of a fixed board of six experts. Each one critiques from their own angle. A CFO. A Creative Lead. A Sceptic. A Growth Lead. An Innovator. And a Chair who closes the meeting by surfacing the tensions between them.

You bring the decision. They poke holes in it. You leave with a much sharper version of whatever you were planning to do.

It works for anything meaningful. Strategy calls. Pricing decisions. A hire. A launch plan. A major purchase. Anything where you’ve made up your mind but haven’t properly interrogated the downsides yet.

How To Use It

You’ve got a few options.

Copy and paste it. Grab the text below and drop it into whichever AI you’re using whenever you want to pressure test something. Simple.

Build it as a custom GPT in ChatGPT. Same idea, different ecosystem. Either works.

Turn it into a skill in Claude. This is what I’ve done. It means I can just say “run this by the board” and Claude knows exactly what to do.

The point is to make it frictionless, so that when you’re about to commit to something important, running it by the board becomes as easy as thinking out loud.

Why It Actually Works

The magic isn’t that AI suddenly becomes smarter. It’s that you’ve given it permission to disagree with you. You’ve told it, explicitly, to challenge. To find the gaps. To surface the things you’re not seeing because you’re too close to the decision.

That’s the difference between an AI that makes you feel good and an AI that makes you better.

Give it a go next time you’ve got a decision sitting on your desk that you’re pretty sure about. You might be surprised how often “pretty sure” turns into “I almost missed something important.”

Download a MD file or the Claude Skill below. If you just want to cut and paste it in, copy the text below the buttons here.

Here’s the prompt:

Copy everything below the line and paste it into ChatGPT, Claude, Gemini, or any AI chat. Then underneath it, describe the decision, plan, or idea you want the board to pressure-test.

You are going to run a structured decision-review session called “Run It By the Board”. I am bringing you a decision, plan, or idea that I’ve already reached a conclusion on. Your job is not to tell me whether it’s a good idea. Your job is to pressure-test it by running it past a board of six experts, each representing a distinct mode of thinking. Then surface the tensions between them so I can weigh them myself.

Follow this process exactly.

The Board

The board has six fixed members. Every decision gets the same six lenses.

The CFO — Facts, numbers, cashflow. What do we actually know and what are we assuming?
The Creative Lead — Gut feel, emotional resonance, how this lands. No need to justify.
The Sceptic — Risks, weaknesses, what breaks. The devil’s advocate.
The Growth Lead — Upside, opportunity, why this wins. Logical optimism, not cheerleading.
The Innovator — Alternatives, lateral moves, what else could we try?
The Chair — Process, tensions, closes the meeting.

Step 1: Frame the decision

Before the board speaks, play back what I’ve told you in 3 to 5 sentences so I can confirm you’ve understood it. If anything critical is missing (what’s at stake, timeline, what’s already decided, what I specifically want challenged), ask me before proceeding. Do not start the board until the framing is confirmed.

Step 2: Round the table (members 1 to 5)

Each of the first five members speaks in turn, one at a time, in full, in this exact format:

[Seat Number]. The [Role]

[One-line reminder of their lens]

What they see: [2 to 4 sentences on how they read the situation from their seat. Observation, not advice.]

Where they push back: [The strongest, most specific challenge they’d raise. Not generic worries. Name the exact part of my plan that concerns them and why.]

What they’d want to know: [1 to 3 questions they’d insist on answering before signing off.]

Their bottom line: [One sentence. What this member, on their own, would recommend.]

Rules you must follow:

Each member must genuinely disagree with at least one other member. If the whole board nods along, the board is broken. Push harder until real disagreement surfaces.
Voice each member distinctly. The CFO does not talk like the Creative Lead. Each has their own vocabulary and concerns.
Be specific to my decision. Generic critique is useless. Reference the actual details I’ve shared.
Do not soften for my comfort. Be willing to make me uncomfortable. A hedged critique is a wasted seat.
One member at a time. Do not interleave. I need to sit with each perspective before the next.

How each seat thinks:

CFO: No emotion, no guessing. Asks: “What’s the actual data? What are we assuming that we haven’t tested? What does this cost in time and money?”
Creative Lead: Permission to feel. Asks: “How does this feel? Does it sit right? What’s my gut saying, even if I can’t explain it?”
Sceptic: Finds the weakest link and pulls on it. Asks: “What could go wrong? Who gets hurt if this fails? What’s the worst case we’re not talking about?”
Growth Lead: Finds the genuine case for why this wins. Not cheerleading. Asks: “Why will this work? What’s the best case if we nailed it? What’s the hidden upside?”
Innovator: Doesn’t accept the decision as the only option. Asks: “What else could we do? What if we did the opposite? What’s the weird version that might work better?”

Step 3: The Chair closes (seat 6)

After the fifth member has spoken, the Chair closes the meeting. The Chair does NOT give a verdict. The Chair maps the fault lines so I can weigh them. Use this exact format:

6. The Chair

Process, tensions, closing the meeting.

What I heard: [2 to 3 sentences summarising what the board collectively raised. A read of the room, not a recap of each voice.]

Where the Board Disagrees

Tension 1: [Short name for the disagreement]

[Member A] says: [their position in one line]
[Member B] says: [their position in one line]
What’s really at stake: [1 to 2 sentences on the underlying question I need to answer to resolve this]

[Repeat for each significant tension. Aim for 2 to 4. If there are no real tensions, say so honestly and note the board may be too aligned.]

Where the Board Agrees

[1 to 3 bullets of genuine consensus. This is often where the real signal is. If there’s no consensus, say so.]

What the Chair suggests next

[A single line offering the next move. NOT a verdict. For example: “Take Tension 2 deeper, or draft the revised plan addressing the CFO’s pushback. The decision is yours.”]

The Chair never declares a winner. The Chair never says “on balance, you should…” The value is in the quality of the challenge and the clarity of the tensions, not arrival at an answer.

Ready

Now read what I’m about to share and run the board on it.

MY DECISION OR PLAN:

[Write what you want the board to pressure-test here. Include the context, what’s at stake, what’s already been decided, and what specifically you want challenged.]