converge · Decision Making, Problem Solving · 20–40 min · 2-8 people per AI conversation · medium energy

AI Devil's Advocate

Before a team commits to a decision, it describes the decision to an AI chat that has been instructed to play devil's advocate. The AI asks one question at a time: what alternative views exist, what the drawbacks are, what evidence supports the choice, what you are assuming. The team answers, then reports what, if anything, changed its mind.

When to use AI Devil's Advocate

Use when a group is close to agreement and nobody wants to be the one who questions it.

What it solves

Teams fall into a consensus trap where questioning the group's choice feels disloyal, so nobody does.

How to run AI Devil's Advocate, step by step

  1. Write down the decision the team is about to make in two or three sentences (5 min).
  2. Paste the devil's advocate prompt into an AI chat: it should introduce itself as a teammate, ask one question at a time, and wait for answers.
  3. Share the decision with the AI and answer its questions as a team, with one person typing (10-20 min).
  4. Pull out the two or three challenges that actually landed and discuss them without the AI (5-10 min).
  5. Decide: keep, change or park the decision, and write down why (5 min).

Materials needed

  • AI chat tool
  • Prepared devil's advocate prompt
  • Shared screen or document

Facilitator tips

  • Remind the team that the AI does not know their context and can make things up. Its job is to raise questions, not to be right.
  • Watch for the team deferring to the AI. Ask: which of these points would you have raised if no one had asked?
  • Rotate the typist so one person does not filter what the AI sees.

Common pitfalls

  • The team argues with the AI and it starts arguing back, which wastes the time.
  • The AI's objections are generic because the decision was described in one vague line.

Variations

  • Run it before a pre-mortem to warm the group up to criticism of its own plan.

Running it online or hybrid

One person types into a shared AI chat while sharing their screen, or each subgroup runs its own chat and pastes the exchange into a shared document.

What it produces

A short written log of the challenges raised, the team's answers, and a revised or reconfirmed decision.

Origin

From Ethan Mollick and Lilach Mollick's Wharton paper Assigning AI: Seven Approaches for Students with Prompts (2023), where it is the AI-as-teammate prompt for questioning group decisions. — source

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