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This episode challenges goal-driven thinking in an AI-enabled world through a conversation with Radhika Dutt. The discussion explores why OKRs and vanity metrics often fail, especially when AI accelerates optimisation without understanding. The core insight is a shift from goal setting to puzzle setting. By framing problems clearly, staying in the discomfort, and learning through small experiments, teams can build products that create long-term value. Practical examples show how this mindset helped recover stalled growth, improve trust, and reduce churn while keeping humans central to AI-driven decisions.

👉 Full Show Notes
https://www.microsoftinnovationpodcast.com/799

🎙️ What you’ll learn

Why AI makes weak metrics and OKRs more dangerous, not more effective
How to shift from goal setting to puzzle setting in product and AI work
A practical framework for defining problems before jumping to solutions
How to measure learning and narrative, not just numbers
How puzzle solving supports sustainable innovation and growth

✅ Highlights

“We measured success by the logos of companies on our website.”
“Are we all just doomed to learn from trial and error?”
“Everything that we humans can do in terms of optimizing numbers, AI can do it even better.”
“What is the puzzle is the question we should have been asking.”
“The more intimacy was gamified, the more it created a toxic dating environment.”
“You kind of need to stay with the discomfort.”
“Don’t just spit out numbers at me.”
“They hated magic and they did not trust technology.”
“This approach was more like putting your ears on the tracks.”
“It is the biggest illusion that OKRs work.”

🧰 Mentioned

Radical Product Thinking
https://www.radicalproduct.com/
OKRs (Objectives and Key Results)
https://www.atlassian.com/agile/agile-at-scale/okr
Puzzle setting and puzzle solving framework
https://www.radicalproduct.com/toolkit/
Design thinking
https://www.interaction-design.org/literature/topics/design-thinking
Toyota 5 Whys
https://www.learnleansigma.com/guides/5-whys/

✅Keywords
artificial intelligence, ai innovation, okrs, product thinking, puzzle setting, metrics, innovation culture, design thinking, product strategy, ai metrics, business transformation, experimentation

Microsoft 365 Copilot Adoption is a Microsoft Press book for leaders and consultants. It shows how to identify high-value use cases, set guardrails, enable champions, and measure impact, so Copilot sticks. Practical frameworks, checklists, and metrics you can use this month. Get the book: https://bit.ly/CopilotAdoption

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Thanks for listening 🚀 - Mark Smith

Stop Chasing OKRs: Solve the Real Business Puzzle