Convincing Leaders to Stay With Discomfort

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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