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War-game a hard decision with Claude

Hey, it's Cindy 🌱 This guide gives you the one framing plus the exact prompts to make Claude war-game your decision before you commit.
btw the waitlist for AI System Club is now open! If you're keen on using AI to automate your content, video editing, job search, business or build AI agents, feel free to sign up (only if you want to hehe). Ps. the waitlist gets first dibs:)
the theory

The 70-year-old idea behind it

The prisoner's dilemma is a simple setup: two players, each choosing to cooperate or betray, where betraying looks smart in the short run but wrecks you both if you both do it. In 1980, political scientist Robert Axelrod ran two computer tournaments where scientists submitted strategies to play the game 200 times in a row against each other.

The winner of both was the simplest program entered: tit-for-tat, submitted by Anatol Rapoport. It cooperates on move one, then just copies whatever the other player did last round. The greedy "betray first" strategies racked up quick points and then collapsed, because everyone learned to punish them.

Axelrod found the winning strategies shared four traits, and these are the ones worth stealing for real decisions:

🕊️ Nice never defect first, don't start the fight.
🛡️ Retaliatory respond if they betray, so you can't be exploited.
🤝 Forgiving go back to cooperating fast once they do, don't hold a grudge.
🔍 Clear be predictable enough that the other side can safely cooperate with you.

Source for the tournament and the four properties: Axelrod's tournaments, PLOS One review and the Axelrod-Python tournament docs.


why it matters

Why this matters for a business decision

The trap in almost every hard call is that you model it as a one-off. "Should I undercut them on price?" feels like a single move, so the aggressive answer looks free. But business is repeated: the same competitor, client, or partner is still there next quarter, and they remember what you did. The one-time win quietly costs you the relationship, the trust, or the price floor for years.

Claude is genuinely good at this because it can hold every branch open at once, name the second and third move you can't see yet, and stay unemotional while you're the one with skin in the game. It is not predicting the future. It is forcing you to look past move one.


copy this

The exact prompt to run

Paste this into Claude (works in Claude.ai or the Claude app), then fill in your real numbers. The more honest your payoffs, the sharper the answer.

🧩 the war-game prompt
I'm stuck on a real business decision and I want you to war-game it using game theory, specifically the repeated prisoner's dilemma.

The decision: [describe it in one line, e.g. "do I undercut competitor X on price or hold my rate"].

The players: me and [the other party].

The payoffs as I see them:
- If we both cooperate (both hold): [what happens]
- If we both defect (both undercut / race to the bottom): [what happens]
- If I defect and they cooperate: [what I gain, what they lose]
- If I cooperate and they defect: [what I lose]

Important: model this as a REPEATED game, not a one-off, because I'll be dealing with this party again. Walk me through: (1) what the naive one-off move would be and why it's a trap, (2) how the game changes when it repeats, (3) the strategy that compounds in my favour over many rounds, and (4) the exact first move you'd recommend and what signal it sends. Point out where a "win once" move quietly costs me the relationship.
If you don't know your exact payoffs, that's fine. Tell Claude the rough shape ("holding keeps my margin but risks looking expensive; undercutting wins the deal but starts a price war") and it'll help you fill the grid in.

go further

3 bonus prompts to run next

Same decision, different angles. Run whichever fits.

1 · play the other side
Now play the other side. You are [the competitor / partner]. Given my likely move, what's your best response, and your response to that? Run three rounds of move and counter-move so I can see where this actually lands, not just round one.
2 · flip the assumption
Re-run the analysis but change one assumption: what if this is the LAST time I'll ever deal with this party (a true one-off)? Show me how the right move flips, so I understand exactly how much the "we'll meet again" part is driving my decision.
3 · stress-test it
Stress-test your own recommendation. Argue the strongest case AGAINST the move you just told me to make. What would have to be true for the opposite choice to be right, and what's the cheapest thing I could do to find that out before I commit?

pick your level

How to get the most out of it

🌱 If you're newer to this don't overthink the payoff numbers. Even rough words ("a lot", "a little", "I lose the client") give Claude enough to map the branches. The value is seeing move two and three, not building a perfect spreadsheet.
⚡ If you want to go deeper ask Claude to name the actual strategy it's recommending (tit-for-tat, grim trigger, generous tit-for-tat) and explain the tradeoff. "Generous" tit-for-tat forgives the occasional betrayal to avoid a death spiral of retaliation, which is often the smarter real-world play when signals are noisy.

the honest bit

When not to lean on this

Game theory sharpens decisions where another party reacts to you. It's the wrong tool for a purely internal call (which feature to build, how to spend your morning) where there's no opponent responding. And treat the output as a thinking aid, not a verdict: the model is only as good as the payoffs you feed it, so if the answer surprises you, check whether your assumptions were honest before you act on it.
the waitlist is now open

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btw this list gets first dibs
the moment doors open :)