#121 - From Seller to Coach: Gail Behun’s Playbook for Building Better Managers

Most companies take their best sellers and promote them into management, expecting them to magically know how to coach a team. It rarely works that way. Gail Behun, who leads frontline manager enablement at Zoom across 300 managers globally, learned that lesson firsthand when she made the leap from seller to manager and realized she had no template for what good looked like. In this conversation, Gail breaks down how she builds manager capability without overwhelming people who are already stretched thin, why the best enablement comes from managers themselves rather than top-down programs, and how she uses AI, including a custom "Gail Voice" bot, to scale her impact and communicate in a way that actually lands with CROs. If you've ever wondered how to make enablement stick beyond the training session, this one's for you.

When your people complete the mandated AI training but nothing changes, you don't have a tool problem; you have a culture problem. As Director of L&D at Publicis Sapient, Ian Stevens watched mandates and endless emails fail to drive the engagement, adoption, or completions they needed. The breakthrough came when they stopped teaching tools and started building mindsets. Ian reveals their secret weapon, the AI Caravan: 60-minute demos fueled by beer and pizza that brought record numbers into the office voluntarily. He explains why people need to evolve from writers to editors, why adaptability and judgment matter more than technical skills, and how widening the guardrails unlocked momentum. Most importantly, Ian shows how transformation happens with people, not to them. If you're tired of the "hurry up and wait" approach to AI adoption, this episode reveals how to build a culture where experimentation beats prescription every time.

What happens when the context you're preparing leaders for no longer exists by the time they get there? After seven years as Chief Learning Officer at Citibank building talent systems, Cameron Hedrick sees the cracks in how we predict potential.In this conversation, Cameron reveals why mastery beats potential when everything is constantly emerging, why humans excel at inference with small data while AI needs millions of data points, and how self-knowing becomes the foundation for navigating what's next. He introduces his Prompt to Polymath framework, mapping our journey from basic augmentation to a world where your digital twin pre-flights conversations while you orchestrate outcomes across humans, agents, and proxies. From hiring people with scars to narrating learning in motion, Cameron shares why machines may calculate faster, but they don't rise stronger from failure and why that distinction matters more than ever. If you're still running quarterly talent reviews in static nine-boxes, this conversation will fundamentally challenge how you think about developing capability that endures.HIGH POTENTIAL (for what?!)New MIT Sloan research suggests that AI is more likely to complement, not replace, human workers | MIT Sloan

What happens when AI agents become your direct reports? Becky Karsh, VP of Talent and Growth at F5, believes we're approaching a fundamental shift: individual contributors won't just complete tasks, they'll manage multiple AI agents to achieve outcomes. In this episode, Becky reveals why delegation, work design, and crystal-clear communication are becoming essential IC skills, not nice-to-have manager competencies. She explains why "if you do something more than once, that should be an agent" and makes the case that the future belongs to ICs who think like architects, not just builders. From T-shaped careers to bringing your own OKRs to development programs, Becky maps out the new playbook for IC success. If you're wondering whether AI will replace your job, Becky has a different question: are you ready to manage the AI that will amplify your impact?

Is your team resisting AI adoption? Are they struggling to see how AI could actually help their work? Rebecca Scales discovered the real barrier isn't reluctance to learn - it's self-efficacy, people's belief that they can actually use these tools effectively. As Director of Capability Development at Procore Technologies, she watched initial AI training fail because pressing "enroll" meant admitting you don't know something, a psychological barrier especially high for engineers. But Rebecca cracked the code with an unconventional approach that turned resistance into remarkable engagement: 6,000 training sessions in just four months. In this episode, Rebecca reveals her data-driven methodology, the psychological gateway that made formal training feel less threatening, and why one engineer went from saying "no" to becoming her biggest champion.If you're leading an AI initiative and wondering why adoption is slower than expected, this episode will show you what you're missing.

Have you ever sat at your desk, physically present but mentally checked out, your stomach in knots, calling in "sick" when you're really just depleted, feeling like you're giving 110% while running on empty? Ryan Giordano knows that feeling intimately, and his journey from the breaking point of burnout to teaching emotional intelligence at Fleetio reveals a radical truth: we massively underestimate how much control we have over our own experience. Ryan shares why 50% of what happens to us is actually happening inside our heads, introduces the "window metaphor" that transforms how you see reality, and explains why reframing isn't just positive thinking - it's a practical tool that could save your career.Ryan shows how emotional intelligence becomes the antidote when you're always "on" but never okay. If work feels like it's happening TO you rather than WITH you, this conversation is for you.

What happens when your company faces multiple massive changes all at once? Allyson Carr knows exactly what that feels like. As Global HR Chief at Cyber Reason, navigating six months of hyper-change, she reveals why people understand change but struggle with the transition, and why there's a physical toll to transformation that most leaders completely miss. Allyson shares her battle-tested approach: why she hires for human skills over technical expertise at the executive level and why trying to make employees love "the company" is a losing game. In this episode, Allyson shares how to build trust when everything else is in flux. If you're leading through chaos and wondering why your team seems exhausted even when they understand the strategy, this conversation is for you.

What if your next dream job came from a LinkedIn DM instead of a job application? Rachel Bolton landed her role as Director of Global Enterprise Leadership Development at Stanley Black & Decker when a leader reached out after discovering her through her consistent LinkedIn presence. In this episode, Rachel explores the intersection of authentic personal branding and professional growth, revealing how she maintains a vibrant online presence while juggling a demanding L&D role and raising two young children. She shares her philosophy on converting passive profile views into meaningful connections, the importance of bringing your whole self to both digital content and facilitation, and why perfectionism is the enemy of progress when building your professional brand. Tune in to discover how consistency, authenticity, and strategic visibility can transform not just your LinkedIn presence but your entire career trajectory.

What if the best career move you ever make is the one you didn’t plan for?In this episode, we follow the unexpected journey of Bozena Pajak, who found her way to Duolingo, not through a clear-cut plan, but by following her curiosity. You’ll hear how an interdisciplinary background became her superpower, shaping how millions of people learn languages today. But this story goes beyond career twists; it’s about how we learn, why we stay engaged, and what actually makes learning stick.From the science of implicit learning to the art of balancing structure with exploration, this conversation unpacks the hidden forces behind Duolingo’s success. You’ll hear what it really takes to build something effective and addictive and how AI might just personalize learning in ways we’re only beginning to imagine.Whether you’re a designer, educator, team leader, or lifelong learner, this episode will leave you thinking differently about motivation, collaboration, and the future of learning itself.Tune in for a story that proves passion, feedback, and a little serendipity can take you further than any plan ever could.

What does a Hollywood screenwriter know about learning design? Turns out, quite a lot. In this episode, Andrew Barry sits down with Lindsey Caplan, founder of The Gathering Effect, whose background in organizational psychology and TV writing gives her a unique lens on how to craft transformative learning experiences. Lindsey unpacks her go-to framework centered on motivation, structure, and storytelling, reveals the biggest mistakes L&D teams make, and introduces her two-by-two matrix for creating content that’s not just informative, but engaging and scalable. This is a masterclass for anyone serious about designing learning that actually moves people.Listen now to transform the way you think about training.