Why OKRs Fail: Radhika Dutt on Puzzle-Driven Product Strategy, AI, and Building Better Products

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, author of Radical Product Thinking, 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
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 https://pathwise.io/podcasts/radhika-dutt/.
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