AI as a Contrarian Thought Partner

Mark Miller
Jul 11
2 min read

Stop asking AI to agree with you. Start asking it to prove you wrong.

Here's what most people do wrong with AI: they use it like a cheerleader. "Help me brainstorm ideas that build on this concept." "What are some ways to improve my strategy?" It feels productive, but you're just getting smarter versions of your existing thoughts.

Berkeley researchers spent 40 years proving something counterintuitive: groups that argue produce 42% more breakthrough ideas than groups that get along. The catch? It has to be real disagreement, not someone playing devil's advocate for show. When people know you're just "being contrarian," they tune you out.

Through trial and error in daily work at Canva, CJ has learned how to get AI to genuinely push back on design decisions instead of just agreeing with everything. CJ will share the specific approaches that work—and the ones that don't—along with examples of how this plays out when making choices in creative work at all levels.

Three Key Takeaways: Contrarian AI Partner

The authenticity trick: Why "play devil's advocate" prompts fail and what to ask instead to get real intellectual pushback
Calibration matters: How to adjust AI challenge intensity based on whether you're a beginner or expert (get this wrong and it backfires)
The push-pull sequence: When to seek AI validation versus when to invite disagreement for maximum creative output

CJ's session, "AI as a Contrarian Thought Partner, will be streamed globally from Sydney, Australia September 16-17, 2025 as part of The Artificial UnIntelligence Conference.

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About CJ Jones

CJ is the Head of Design for Generative AI at Canva. She and her team build sustainable and useful AI experiences for Canva's hundreds of millions of users across the world. Their recent launches include Canva AI, a conversational assistant that creates designs, images, docs and code.

Previously, she worked on transport and food delivery at Grab, NLP research at the Allen Institute for AI, and marketplace design at Rover. She also writes on Substack about recalibrating success and priorities as a high-achiever, and advises founders through their startup journeys.

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