What if everything we've been taught about goal-setting is fundamentally wrong for the work we actually do today? In today’s episode, Radhika Dutt, author of Radical Product Thinking, makes the case that traditional goal-setting methodologies are solving a 1940s problem and aren’t helping organizations deliver their best work anymore - and haven’t been for decades.

What worked for repetitive assembly line tasks simply doesn't translate to today's creative problem-solving environment.

The research is clear: goal-setting excels when there's one right way to do something (like crunches at the gym), but fails spectacularly when applied to strategic puzzles with multiple possible solutions. Instead of targets that create what Radhika calls "soul-sucking" work environments, she proposes thinking in terms of puzzles and experiments—shifting from "Did we hit the number?" to "What did we learn and what will we try next?"

We explore Radhika’s proprietary framework which replaces the red/yellow/green status updates of traditional goal tracking with meaningful conversations about actual progress and learning. This approach emphasizes psychological safety, where teams can share both successes and failures without fear of retribution—because in puzzle-solving, failures are data, not deficiencies.

Radhika also introduces us to "product diseases"—the common ailments that plague organizations including Pivotitis, Obsessive Sales Disorder, and Hero Syndrome. These diseases often emerge from misaligned goal-setting practices that prioritize metrics over meaningful progress.

For managers caught in OKR-obsessed organizations, Radhika offers practical advice on introducing puzzle-thinking gradually, starting with your own team and slowly shifting organizational conversations from targets to learning. The key is creating psychological safety where messengers aren't shot for bringing bad news, and where "How well did it work?" becomes as important as "Did we achieve it?"

Resources & Links

Radhika's Website

Her books: Radical Product Thinking: The New Mindset for Innovating Smarter and the upcoming book on Goals and OKRs

Radhika Dutt on LinkedIn - Share your OLA experiences for potential inclusion in her upcoming book

Download Radhika's free toolkit

Get Tosca's book - NSFW: A good manager's guide to better feeling work in a toxic culture