Bottom line: Assign Claude three competing roles and have them debate your strategy. The disagreement is the point.
Why Single-Voice Feedback Fails
When you ask an LLM for feedback on a plan, it tends to give you something polished and slightly too agreeable. Not because it’s wrong, but because helpfulness defaults to validation. That’s fine for editing. It’s a problem when you need real critique.
One voice means one set of blind spots.
Think about what happens when you ask “What are the weaknesses in this plan?” The model scans the plan, finds a few surface-level concerns, wraps them in diplomatic language, and sends back something that feels balanced but doesn’t actually hurt. It’s the equivalent of asking your most agreeable colleague for honest feedback. They’ll say something. It just won’t be the thing you needed to hear.
The model isn’t trying to flatter you. It’s optimizing for a helpful response. And a single helpful responder with no counterpoint and no stakes almost always drifts toward encouragement. You need structure that forces conflict, not just asks for it.
The Boardroom Technique
The fix is simple. Instead of one voice, assign a panel. A Growth CMO who wants to scale fast. A Skeptical CFO who wants to cut waste. A Head of Product who wants to ship the right thing. Give them a strategy and have them debate it in two rounds.
The tension between those roles is the whole point. A CFO won’t let a growth plan slide without asking what it costs. A Head of Product will push back on both. That friction surfaces assumptions you didn’t know you were making.
Here’s a concrete example. Say you’re planning to double your ad spend next quarter to accelerate subscriber growth. The Growth CMO loves it. The CFO immediately asks what your current CAC is, whether the new subscribers are monetizing, and what the payback window looks like. The Head of Product flags that your onboarding flow hasn’t been touched in six months and that you’re about to pour money into a leaky bucket. Suddenly you have three real problems to solve before you spend a dollar, not a green light and a good feeling.
That’s the kind of output that changes what you do next. A single “here are some considerations” response rarely does.
The Base Prompt
Act as a panel: A Growth CMO, a Skeptical CFO, and a Head of Product. Conduct a 2-round debate on [Strategy] to find the flaw.
The panel is flexible. Swap in Legal, Engineering, and Sales for a product decision. Use Investor, Customer, and Operator for a pitch. The structure holds across contexts.
You can also weight the roles toward your actual risk. If you’re worried about execution, lean on Engineering. If you’re walking into a board meeting, put an Investor in the room. The panel should reflect the real critics you’ll face, not just generic archetypes. The more specific the roles, the sharper the debate.
📋 Use Cases
- Testing a go-to-market plan before the real meeting
- Stress-testing a pricing decision across departments
- Running a pre-mortem on a launch before it ships
- Getting unstuck when a call feels obvious but something still seems off
- Pressure-testing a hiring plan before you’ve committed headcount
- Checking whether your positioning holds up under investor scrutiny before a raise
Why It Works
Most prompts give the model a single job. This one gives it three competing jobs and a conflict to resolve. That pressure forces Claude to steelman and attack the same idea from different angles, which is closer to how real decisions actually get made.
When you assign three roles with genuinely different incentives, the model can’t default to one coherent perspective. The CFO is structurally required to push back on what the CMO proposes. The Head of Product is structurally required to ask whether any of this is even the right problem. The roles create friction by design, and that friction is what produces useful output.
There’s also a second-order benefit. After you run this prompt, you know which objections are coming before you walk into the room. You can decide which ones to address in the plan itself and which ones to handle live. That’s not just feedback. That’s rehearsal.
Prompt of the Day
Act as a panel: A Growth CMO, a Skeptical CFO, and a Head of Product. Conduct a 2-round debate on [your strategy] to find the flaw. Round 1: Each role makes their strongest case. Round 2: Each role responds to the others and names the biggest risk they see. End with a ranked list of the top 3 unresolved tensions in the strategy.
Try It
Run your next strategy through the boardroom before you take it into a real one. If three competing voices can’t punch a hole in it, you’re probably ready.
And if they do find a hole, that’s the best possible outcome. You found it before someone else did.
The ‘Boardroom’ Multi-Expert Debate.
by u/Significant-Strike40 in PromptEngineering