Productly Speaking: Real Stories for Product Managers

Have you ever walked out of a meeting convinced everyone was aligned, only to discover weeks later that half the team heard something completely different? Stan Slovin has spent years working with leaders who thought they were listening, until the silence, the turnover, and the failed projects proved otherwise. In this conversation, we dig into the small tells that reveal when someone has stopped hearing you, the moment a CEO's din...

Have you ever sat through yet another transformation announcement and quietly thought, "here we go again"? Alex Adamopolous II has lived through enough of those moments to know the truth: organizations don't struggle with new processes. They struggle with the humans trying to figure them out.

In this conversation, Alex shares what 45% of workers won't tell you in surveys about burnout, the wardrobe app startup that failed because th...

What happens when you spend eight months building something impressive, only to discover the people who promised to use it actually don't want it? Richard Abi Chahla knows that moment. The deflation. The walk back to the team. The hard conversation about wasted months and sweat equity. In this conversation, Richard shares what he learned from that 2016 failure and how he now uses AI not to build faster, but to learn faster. We dig ...

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...

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 feedback...

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 produc...

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...

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 making sense.

Thi...

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 real human needs, and ...

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 out if you get it wrong. The pressure...

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 she realized that every...

 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 because it sounds wise, but because ...

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 challenge your assumptions ...

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 product manager came back asking to...

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 the mission, and then navigating t...

What if being a great product manager had less to do with sounding smart and more to do with getting your hands dirty?

In this episode, Karl talks with Ali Rakhimov about a product career that started far away from tech titles, roadmaps, or polished decks. Ali shares how he quite literally tripped into product work while trying to solve real problems in K–12 schools, like watching student cash disappear at the front office and...

What if your path into product management started behind a coffee counter, in the middle of a global pandemic?

In this episode, Karl talks with Flora Taagen about a journey into product management that looks nothing like a straight line. Flora shares how she went from studying computer science to serving coffee during COVID, where suddenly “making coffee” also meant rethinking safety, budgets, and how a small business su...

What if you were already doing product work years before you ever heard the job title?

In this episode, Karl talks with Adil Hussain about a path into product management that started with a teenage side project and quietly grew into a career. Adil shares how, at just 14, he and a co‑founder were building websites, talking to users, and figuring out what people actually needed, without realizing they were doing product work at all. I...

What happens when the thing you worked so hard to build starts quietly working against you?

In this episode, Karl talks with Kevin Bailey about the hidden cost of high‑growth success and what burnout really looks like when it sneaks up on you. Kevin shares the story of building a bootstrapped startup with two friends in his twenties, watching it explode from a team of three to over a hundred people, and suddenly feeling the shift fr...