Productly Speaking: Real Stories for Product Managers

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...

What really happens when sales and product have to sit in the same room and agree on what matters?

In this episode, Karl talks with Richard Cawkill about the lived reality of working at the messy, often misunderstood intersection of sales and product. Richard shares what it feels like to carry a number, build long‑term relationships with customers, and still genuinely care about protecting the integrity of the product. From two‑year...

What if the biggest risk to your product isn’t what you build, but how you talk about it?

In this episode, Karl sits down with Austin Fuller to unpack the very human tension between product and product marketing, and why getting that relationship wrong often shows up much later, in churn, confusion, or missed expectations. Austin shares what he’s learned from years of listening closely to customers and prospects, includi...

Have you ever ended a workday exhausted, knowing you were busy all day, but unsure what actually moved forward?

In this episode, Karl sits down with Keith Allen Johns to talk about the invisible weight product managers carry and why the stress of the role so often shows up at work and at home. Keith shares his own journey from climbing to the C‑suite to realizing that something still felt off, and how that search for “what&rsq...

What happens when two product people stop chasing perfection and start talking honestly about the job?

In this episode, Karl is joined by Evie Brockwell and Michael Palmer for a wide-ranging, refreshingly human conversation about what product work really feels like day to day. Michael shares the excitement and pressure of stepping into BBC iPlayer, including the surreal experience of watching real people sit on a couch in a mock liv...