The 'Make the Other Mistake' Strategy
by Mike Krieger • Chief Product Officer (CPO) at Anthropic at Anthropic
Co-founder and former CTO of Instagram. Currently leading product at Anthropic (makers of Claude), where he oversees the development of AI models and products like Claude and Artifacts.
🎙️ Episode Context
Mike Krieger discusses the radical shift in software development at Anthropic, where 90% of code is now written by AI. He explores how product management evolves when engineering barriers vanish, the strategic importance of MCP (Model Context Protocol), and how to compete as a 'challenger' brand against OpenAI. He also shares lessons from shutting down his news app, Artifact, and advice for AI founders on avoiding being crushed by foundational models.
Problem It Solves
Overcoming AI models' tendency to be sycophantic, agreeable, or generic when acting as a strategic thought partner.
Framework Overview
To get high-quality strategic critique from an AI, you must explicitly push it to the opposite extreme of its training. If it's too nice, ask it to be brutal. If it's too shallow, force it to 'think hard' about reasoning before answering.
🧠 Framework Structure
Roast the Strategy: Explicitly instru...
Request Reasoning: Ask the model to '...
Meta-Prompting: Use the model to writ...
When to Use
When using LLMs for high-level product strategy, critiques, or decision-making support where honesty matters more than politeness.
Common Mistakes
Using standard polite prompts like 'What could be better?', which yields anodyne/generic feedback.
Real World Example
Mike uses Claude as his primary strategy partner. Instead of asking for feedback, he asks Claude to 'roast' his product strategy for the second half of the year, leading to novel angles he hadn't considered.
With Claude sometimes I'm like, 'Be brutal, Claude, roast me. Tell me what's wrong with this strategy.'... make the other mistake.
— Mike Krieger