Why OKRs Fail: Radhika Dutt on Puzzle-Driven Product Strategy, AI, and Building Better Products
2/16/2026 | 34 mins.
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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How Curiosity Shaped My Career Journey, With Ryan Hawk
2/09/2026 | 47 mins.
The journey from individual contributor to effective manager is often called the most significant transition of a career—a shift not just in responsibilities, but in identity. Yet, the foundations of great leadership often start with a more personal, foundational practice: curiosity and continuous self-improvement. In this deep-dive interview, we sit down with leadership expert and podcast host, Ryan Hawk of The Learning Leader Show, to unpack his best-selling book, Welcome to Management, and the surprising lessons he's gathered from interviewing hundreds of the world’s most successful leaders. Ryan shares the critical mindset shifts every new manager needs to make, why leading yourself is the necessary first step, and how embracing a learning leader mindset—fueled by relentless curiosity—was the unexpected catalyst that propelled his own professional journey from cold-calling sales rep to full-time entrepreneur and author.
If you're looking to master the art of management, cultivate psychological safety in your team, or simply unlock the compounding power of daily personal growth, you won't want to miss these powerful insights on how curiosity shapes success.
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/ryan-hawk.
Become a PathWise member today! Join at https://pathwise.io/join-now/
How To Boost Your Executive Presence And Visibility, With Katy McFee
2/02/2026 | 42 mins.
The term executive presence shows up constantly in professional feedback—but what does it actually mean? For many ambitious professionals, especially women, this vague phrase becomes a frustrating barrier that leaves them overlooked and unsure how to advance. Today, we unpack executive presence with former tech executive and executive coach Katy McFee. She shares how she bridged the gap from director to VP—and how she now helps women do it faster. Inside, you’ll learn why “head-down hard work” stops paying off at senior levels, how to push back on vague feedback and get clarity, and Katy’s practical advice for building authentic visibility through mindset, skills, and habits. If you’re ready to stop feeling stuck and start showing up as a confident, influential leader, keep reading.
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/katy-mcfee.
Become a PathWise member today! Join at https://pathwise.io/join-now/
How To Go From Surviving To Thriving, With Jon Rosemberg
1/26/2026 | 47 mins.
If we are forever in survival mode, unlocking and unleashing our full potential would be impossible. Jon Rosemberg, Co-Founder Of Anther, reveals what it takes to achieve your thriving mode. He joins J.R. Lowry to talk about his newest book A Guide To Thriving, as well as what it takes to feel a greater sense of control over the things happening in your life. Jon delves into the idea of giving yourself agency to make the most of your human experience and experience profound self-transformation. Find out how to escape the constant struggle of survival mode and get into thriving mode that leads to fulfillment.
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/jon-rosemberg.
Become a PathWise member today! Join at https://pathwise.io/join-now/
How To Master Your Intentions And Lead With Purpose And Power, With Bianca D'Alessio
1/20/2026 | 47 mins.
If you learn how to live with intention, you can lead with purpose and manifest all of your goals in life. This is exactly what Bianca D'Alessio did, which led to her becoming the number one real estate broker in New York City. She joins J.R. Lowry to share all about her journey centered on authenticity, leading with lasting impact, and discovering gratitude even in her biggest failures. Bianca also talks about her new book, Mastering Intentions, wherein she breaks down daily practices to amplify your own power. Discover how to manage your narrative, be comfortable with vulnerability, and unlock resilience both in business and in life.
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/bianca-dalessio.
Become a PathWise member today! Join at https://pathwise.io/join-now/
Each of us has a unique career story to tell. For the lucky few, their career trajectories are like rockets heading for the stars, with no turning back. More typically, our career paths are more like a game of Chutes and Ladders, with advances and setbacks along the way. On this podcast, guests from a range of industries and backgrounds share their career journeys and the lessons they've learned. Hear from C-level executives, leading academics, entrepreneurs, mid-level leaders, ex-military members, leadership coaches and other career experts, non-profit workers, and gig economy participants. Each guest shares their unique story and career insights to inform and inspire your own path. Career Sessions is part of PathWise.io. Whether you’re just a few years out of school or well into your professional life, PathWise helps you live the career you deserve. PathWise provides comprehensive career and professional development coaching, content, courses, and community, backed by a group of leading coaches and career management experts. Career Sessions’ host, James (J.R.) Lowry, has had multiple careers of his own and learned countless lessons along the way. A Duke engineer by background, he spent the early part of his career as an officer in the US Air Force . From there, J.R. earned an MBA from Harvard Business School to accelerate his transition into the private sector. Following grad school, he spent over a decade with the consulting firm, McKinsey and Company, working with clients across a range of industries and business situations. He then made a second career shift into financial services, spending time at Fidelity Investments and State Street Bank. Most recently, he joined Janus Henderson Investments as their Chief Operating Officer. Multiple leadership development programs honed his skills, advanced his career, and fueled his desire to help others with their professions. He hosts this podcast in a personal capacity, and any views expressed are his own and not those of his current or any former employer.