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If you’re a product manager, founder, executive, or even an individual contributor navigating OKRs, AI, and innovation pressure, this episode of Career Sessions, Career Lessons offers a practical reframing of how great products and meaningful work actually get built. Host JR Lowry sits down with Radhika Dutt (https://rdutt.com/), author of Radical Product Thinking (https://www.amazon.com/Radical-Produc..., to unpack why traditional goals, OKRs, and performance targets often do more harm than good in modern product organizations. Drawing from her experience as an MIT-trained engineer, startup founder, and product leader across industries, Radhika introduces an alternative: puzzle setting and puzzle solving. Rather than optimizing for short-term metrics, she says that the most successful teams spend more time in the problem space asking better questions, learning faster, and adapting intelligently. Together, JR and Radhika explore: ● Why OKRs and targets could kill curiosity and innovation ● The difference between optimizing numbers and solving the right problem ● How “puzzle-driven” teams outperform “goal-driven” teams ● The dangers of AI-driven “product slop” and what humans must do better than machines ● Leadership lessons on delegation, critical thinking, and psychological safety ● AI’s impact on recruiting and culture Chapters: [00:00] - Hookline [01:16] - Introduction To Radhika Dutt & Radical Product Thinking [04:13] - The Inevitability Of Mistakes In Entrepreneurship & Reflection As Learning [06:00] - The Value Of Not Knowing & Asking The Right Questions (The Puzzle Approach) [08:50] - The Backfire Of Traditional Goals (OKRs) & The "Leaders Are The Last To Know" Concept [14:24] - The Puzzle Setting & Solving Framework (Signal Maritime Example) [23:51] - Puzzle Setting & Solving As A Defense Against AI & Product Slop [31:17] - Bringing Puzzle Setting Into Your Work Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at [insert URL for the transcript of this episode.]