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 [insert URL for the transcript of this episode.]

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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.

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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.

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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.

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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.

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Every entrepreneur dreams of scaling their business, but what happens when business growth stalls? You've hit a revenue ceiling, your team is expanding, and suddenly, the systems that once brought success seem to be working against you. Matt Pohl, founder and CEO of The ReWild Group, faced this exact challenge—taking his own plateaued business from $1 million to $4 million in three years after discovering a framework that fundamentally changed how he viewed organizational complexity.

In this deep-dive interview, Matt shares the revolutionary concept of organizational rewilding, explaining why employee count, not revenue, is the true driver of complexity and growth stages. Discover the hidden barriers most business owners overlook, the critical difference between being owner-centric and enterprise-centric, and the "missing gray wolves" you need to reintroduce into your company's ecosystem to thrive through chaos and competition. If you're struggling to sustain momentum, or just want to make growth easier, Matt's roadmap is the essential guide to lightening your entrepreneurial backpack.

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/matt-pohl/.

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In an ideal world, every manager would be a mentor, motivator, and model of leadership. But for too many professionals, the reality is far messier. If you’ve ever had to deal with bad bosses—the micromanagers, the emotionally unavailable, or the toxic cheerleaders—you know the profound toll it takes on your mental health and career trajectory.

In this deep-dive discussion, we sit down with Mita Mallick, best-selling author of The Devil Emails at Midnight, to unpack the pervasive problem of bad management. Mita shares her personal journey through 13 different types of awful leadership, revealing why these figures are tolerated, how they are made (not born), and the concrete strategies you need to manage up or know when it’s time to craft your exit plan. Plus, learn the surprising bad boss behavior that flies under the radar but can be the most detrimental to your team. Ready to reclaim control of your work life? Keep listening.

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/mita-mallick/.

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In this time of ever-evolving technology, every working professional will encounter AI in some shape or form. As we go deeper into the age of AI, what is the role of such tools in shaping the future of work and the entire economy? J.R. Lowry talks all about it with Dr. Joerg Storm, IT executive and publisher of the Digital Storm AI newsletter. They discuss why AI is a career-critical tool, the uniqueness of adaptive AI projects, and the technological paradigm shifts to look forward to in the next several years. Dr. Joerg also explains why AI practitioners should remain philosophical and ethical despite their deep immersion in technology to navigate the challenges of bias and trust.

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/dr-joerg-storm.

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