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Productly Speaking: Real Stories for Product Managers

Productly Speaking: Real Stories for Product Managers

Product Management Stories by Productly Speaking 33 episodes Latest May 5, 2026

Productly Speaking is a product management podcast featuring product managers and builders telling real product stories. We dive into the human side of product work, exploring lessons learned, challenges faced, and how people actually approach product strategy in the real world.

Episodes

S5E4: Authenticity Over 'Fake It': Lessons in Leadership and Life with Reese Gifford May 5, 2026 2123 At some point in your career, you have to decide who you’re going to be when things are uncomfortable. In this episode of Productly Speaking, returning guest Reese Gifford joins Karl Abbott to talk about authenticity and humility, not as polished leadership traits, but as choices made under pressure. The kind that cost you something in the moment and only make sense later. Reese reflects on enteri
S5E3: Navigating the Complexity of Product Leadership with Rick Lewis Apr 28, 2026 2233 What if the moment everything tilts sideways at work could actually make you better at your job? In this episode, Rick Lewis sits down to talk about the messy middle of change, the kind that knocks the wind out of a team long before it becomes one of those polished “growth stories.” Rick brings stories from big reorganizations, mergers that paired frenemies into one team, and the kind of customer
S5E2: Finding Balance in Product Management with Katie Tamblin Apr 21, 2026 2976 Ever had one of those weeks where the roadmap is bursting at the seams, everyone wants one more thing, and you can practically feel your balance slipping through your fingers? This conversation with Katie Tamblin goes right into that moment. Katie shares the kind of stories product people don’t usually admit out loud. There’s the time she walked into a team with seventy‑two product “priorities” ta
S5E1: From Punk Rock to Product Management with Scott McCarty Apr 14, 2026 2717 Ever wonder how a punk‑rock kid hauling amps through Midwest basements ends up helping steer one of the world’s most widely used pieces of enterprise software? Yeah… us too. In this episode, Scott McCarty invites us into the winding, deeply human story behind his career — a life that didn’t unfold in straight lines so much as heartfelt pivots. Scott shares what it felt like when the band he’d pour
Season 5 Trailer: The Human Side of Product Management Mar 31, 2026 151 Product management gets talked about like it’s all clarity, confidence, and momentum. But most of the time, it’s not.Season 5 of Productly Speaking explores the human side of product work — authenticity, balance, uncertainty, and values.These are conversations about what product management actually feels like when things are unclear, when the roadmap breaks, or when the rules everyone repeats stop
S4E4: AI, Product Failure, and the Skills PMs Need for What’s Next with Dina Atia Feb 10, 2026 1976 AI is supposed to feel magical. So why does it so often leave product teams confused, overpromised, or quietly disappointed?In this episode, Karl sits down with Dina Atia, a PM working on AI products at Microsoft, to talk about what it is actually like to build in the middle of the hype. Dina shares candid stories from the trenches, like watching teams chase “cool” AI ideas that never quite map to
S4E3: Beyond Dogfooding: Balancing Complexity and Market Insight with Jake Bowen-Bate Feb 3, 2026 1996 What if the thing you are closest to is actually what is blinding you?In this episode, Karl talks with Jake Bowen-Bate about the quiet, human challenges of building products in fast‑moving environments. Jake shares what it really feels like to work in places where you are building the plane, flying it, and still figuring out how the controls work, all while knowing the money might literally run ou
S4E2: Why Lean and Agile Struggle in Chunky Corporates with Katie Tamblin Jan 27, 2026 2406 What happens when all the advice you followed turns out to be wrong for the job in front of you?In this episode, Karl talks with Katie Tamblin about the lived reality of building products inside what she calls “chunky corporates” and why so many well‑intentioned product efforts quietly fall apart there. Katie shares hard‑earned stories from decades inside large organizations, including the moment
S4E1: From Failure to Breakthrough: The Product Manager’s Journey with Lee Fischman Jan 20, 2026 2223  Have you ever realized a mistake only after you hit send?In this episode, Karl sits down with Lee Fischman to talk about the very human side of product work, the part that rarely makes it into neat success stories. Lee shares lessons shaped by decades of building products across wildly different industries, including the hard-earned habit of letting every message sit before responding. Not becaus
Season 4 Introduction Jan 13, 2026 99 Welcome to Season 4 of Productly Speaking! In this short kickoff episode, host Karl Abbott introduces the theme for the season:Why do products fail and what can we learn from those failures?We’ll explore the hidden risks, organizational dynamics, and human factors that shape product success or lead to disaster.If you’re a product manager, founder, or anyone building products, this season will chal
S3E5: The Truth About Roadmaps: Why Dates Don't Deliver with Janna Bastow Aug 12, 2025 2141 Have you ever put something on a roadmap knowing, deep down, it probably was not going to happen on that date?In this episode, Karl talks with Janna Bastow about the uncomfortable truth behind most roadmaps and the moment she realized they were quietly training teams to overpromise. Janna shares the story of building her first roadmap tool and the surprising pattern that emerged when almost every
S3E4: Open Source, Real Business: Lessons from Mozilla and Microsoft with Reese Gifford Aug 5, 2025 1696 What happens when the people building your product do not work for your company, and still feel deep ownership over every decision?In this episode, Karl talks with Reese Gifford about the lived reality of building products in open source, where community passion can be both your greatest strength and your hardest constraint. Reese shares what it was like stepping into Mozilla, falling in love with

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