When execution stops being hard, what becomes visible? For Razy Shah, it was a three-hour meeting with a restaurateur who had no budget. He went in planning to spend an hour. He left energized but uncertain. Years later, that meeting turned into a six-figure contract. This isn't a story about networking strategy or playing the long game. It's about what we choose when nothing is forcing our hand. As AI takes over more execution, the space between what we can do and what we should do gets wider. Razy runs a digital marketing agency that lost its first client to ChatGPT in May 2023. He's spent the years since asking what matters when the craft becomes cheap. This conversation is about judgment, restraint, human connection, and the moments that don't look important until much later.

About the Guest:

Razy Shah is the co-founder of a digital marketing agency he's been running for over a decade, working with small businesses, startups, and large companies across Southeast Asia.

Quotable Moments:

"The hardest thing to choose is restraint. Making sure that even though the AI has written my LinkedIn post, I put in the time, the care to look through it, to improve it further."

"We are all very fixated on the short term outcome. We don't think of the longer term potential benefits. You're just very short term, very outcome driven, not so much long term thinking and relationship driven."

"Across all of these countries, the top thing that people cited was human connection. That's the only thing that we can do in the age of AI. We have to go out there more, meet people, connect, provide value."

Resources Mentioned:

• KPMG and University of Melbourne study on trust in AI-generated content (48,000 people across 47 countries) - Trust, attitudes and use of artificial intelligence: A global study 2025
• Nuremberg Institute for Market Decisions study on AI-generated ads and trust - Consumer attitudes toward AI-generated marketing content | NIM
• Kapwing study on AI slop channels on YouTube - AI Slop Report: The Global Rise of Low-Quality AI Videos
• Will Smith eating pasta AI video comparisons - Will Smith Eating Spaghetti test - Wikipedia

Listen and Connect:

If you've ever said yes to something that didn't make sense on paper, or found yourself wondering what still matters when the work gets easier, this one's for you. Subscribe to Productly Speaking wherever you listen, and if this episode landed, share it with someone who's trying to figure out what good work looks like right now.

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 dinner table question changed his relationship with his daughter, and why the impulse to solve instead of listen might be costing you more than you realize. This isn't about communication frameworks or active listening checklists. It's about what actually happens when people feel unheard, and the surprisingly simple shifts that turn surface interactions into conversations that build trust, clarity, and better work.

Quotable Moments:

"When you talk, you're only repeating what you already know. But when you listen, you actually may learn something."

"The number one reason clients leave is never because of performance. It's because they feel that they were not listened to."

"Listen more and say less. Because that's really where it comes down to."

About the Guest:

Stan Slovin works with leaders and teams in high-stakes environments where listening isn't optional. He's the author of a book on better listening and has seen firsthand what happens when the people doing the work feel like their voices don't matter.

Call-to-Action:

Next time someone on your team starts talking, try this: don't solve, don't respond, don't finish their sentence. Just ask them to tell you more. You might be surprised by what you've been missing. If this episode landed for you, share it with a PM who needs the reminder that listening is still the most underrated skill we have.

Resources:

• "Good to Great" by Jim Collins (referenced in the episode regarding the concept that great leaders are great listeners) - Good to Great: Why Some Companies Make the Leap...and Others Don't by Jim Collins | The StoryGraph
• "Better Listening" by Stan Slovin: https://www.betterlisteningbook.com/

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 they asked all the wrong questions, and why AI is creating the pressure test that product people have been both asking for and dreading. We talk about the gap between learning something in a training room and actually applying it when the stakes are real, the discomfort of embracing ambiguity when moving from project to product thinking, and what happens when teams suddenly have time for strategic work but aren't sure they can deliver it.

This is transformation fatigue, methodology dependency, and the messy truth about change, told by someone who helps teams navigate it every day.

Guest

Alex Adamopolous II leads product development at Emerge and has spent years helping organizations navigate the human side of transformation. He specializes in work-based learning and building product capabilities in teams transitioning from project-based to product-led thinking.

Quotable Moments

"We were more obsessed with the shiny object, the idea of an app that could help people manage their wardrobe. Today, looking back, we would have killed the idea sooner if we had recognized those product management challenges more up front."

"Transformation fatigue honestly looks like exhaustion with the same initiatives or what appears to be the same initiatives being instituted by leadership over and over again."

"Just because AI can get things done at the speed of light doesn't mean that all of our human experience is immediately invalidated. We have to remain critical thinkers in the way that we use AI."

"It's now a pressure test. Are we capable of that strategic work that we always wanted more time for? And interestingly enough, I think this is an opportunity rather than a negative."

Resources

Emergn Reports and Research:

• Overcoming Transformation Fatigue (white paper by Emerge): Make overcoming transformation fatigue your unfair competitive advantage
• Global Intelligent Delusion Report (2025) - Emergn Survey Report: The Global Intelligent Delusion

Tools and Products Mentioned:

• Praxis - Work-based learning platform by Emerge featuring Stella, an AI assistant for product management work - Praxis by Emergn - Emergn
• Vibe coding tools (referenced in rapid prototyping discussion)

Key Concepts Discussed:

• Work-based learning vs. traditional training
• Five types of transformation fatigue: long wait for value, new change same as old change, methodology dependency, buzzwords that lose impact, and skills/talent retention
• Project to product transformation
• AI-assisted software development and learning

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 into the messy reality of validating your riskiest assumptions first instead of the comfortable ones, why having a confident CEO armed with ChatGPT can be dangerous, and the three pillars every startup must stand on before writing a single line of code. If you've ever felt the pull to just keep building because stopping feels too painful, this one's for you.

Guest

Richard Abi Chahla helps subject matter experts and founders use AI to accelerate product discovery and validation. He has been building startups since 2011 and now uses AI to compress market research from weeks into days, but only after learning the hard way what happens when you skip the uncomfortable questions.

Quotable Moments

"If it's going to fail, let it fail in the research phase or let it fail in the validation phase. It's better than it failing whenever you have poured a lot of development money on it."

"I am not smarter than you. I just tried more times than you've done. I just failed more times than you have tried."

"The issue that I've done early on was that I was trying to avoid the riskiest assumption. I was trying to postpone it because I want to hear the good things."

Resources Mentioned

• Lean Startup Methodology - The framework Richard relies on for validating assumptions through empathy, validation, ideation, prototyping, and building phases
• Claude (Anthropic) - AI model Richard uses for research and analysis with large context windows
• ChatGPT (OpenAI) - Used for prompt engineering and market research
• Lovable - No-code/low-code tool for rapid prototyping
• Replit - Platform for building and testing prototypes quickly
• Cursor - AI-assisted code editor
• GitHub Copilot - AI coding assistant
• Function Health - Referenced as the type of platform a client wanted to replicate
• Supabase - Backend solution for quick validation
• Firebase - Backend platform for rapid prototyping

Call to Action

If you've learned something the hard way in product, or you're currently staring down a risky assumption you'd rather not validate, we want to hear from you. Share your story, your question, or just say hello at productly.fm. And if this episode resonated, please share it with another product person who might need to hear it. We're all figuring this out together.

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 entering tech in the late 90s as a young woman with no roadmap, learning early that preparation wasn’t about impressing people. It was about survival. She shares what it felt like to be underestimated in public, to carry the weight of always being “ready,” and to unlearn the belief that strength means having it all together. 

They dig into the moments product leaders know well but rarely talk about. The pause before responding when someone comes at you hard. The risk of saying “I don’t know” in a room that expects certainty. The quiet judgment call between speaking up and staying silent, and how either choice will be interpreted. 

This conversation isn’t about getting it right. It’s about keeping your integrity when the incentives pull you in other directions. About doing your homework, telling the truth kindly, and choosing honesty even when it complicates things. 

If you’ve ever wondered whether being thoughtful is read as weakness, or whether slowing down might actually move things forward, this episode will feel uncomfortably familiar in the best possible way. 

Quotable Moments 

• “You’re affecting people in ways you’ll never fully understand.” 
• “Being kind doesn’t mean avoiding hard conversations. It means protecting people’s dignity while having them.” 
• “You don’t have to prove your worth by carrying things silently. Your voice is part of your strength.” 

About the Guest 

Reese Gifford is a product and technology leader with a career spanning cloud, security, open source, and global platforms. She has led work at the intersection of innovation and real-world impact, and brings a deeply human perspective shaped by decades of learning, unlearning, and showing up with care. 

Resources Mentioned 

• The Wandering Inn by pirateaba 
• https://wanderinginn.com 
• Outfox: The Becoming of Slate Stormheart by Reese Gifford and her son 
• Mentioned in the episode as Reese’s debut science fiction novel co-authored with her son. Availability discussed verbally on the show. 

Call to Action 

If this episode felt familiar in that quiet, uncomfortable way, you’re not alone. Share it with someone who’s trying to do good work without losing themselves in the process. Subscribe wherever you listen, and pass it along the old-fashioned way. Real stories still travel best by word of mouth. 

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 loops that only surface after months of digging. He talks about the small, painfully human moments that happen when people cling to the old way because it feels safer, and the surprising clarity that shows up once you stop trying to control what can’t be controlled. 

There is a moment in this conversation where Rick describes two teams who once competed against each other suddenly being told they’re on the same side. The awkwardness, the reluctance, the gradual warmth that followed. If you've ever walked into a room where no one quite trusts the situation yet, this one will land close to home. 

And then there’s his simple, grounding ritual: stepping outside, clearing his head, and coming back to the problem with a little less fear and a lot more perspective. It’s the kind of habit product people rarely talk about but quietly rely on. 

This episode is for anyone who has ever looked at change and thought, “I know this is supposed to make sense eventually… but right now it just feels like loss.” 

Quotable Moments 

• “Change isn’t something you lose. It’s something you learn how to move through.” 
• “Data is gold dust. Reducing uncertainty is the whole job.” 
• “Once you get past that initial fear, the whole team shifts into a different gear.” 

About the Guest 

Rick Lewis is a product leader who has navigated startups, acquisitions, global teams and more than his share of thorny restructures. Formerly VP of Commercial Products at Element, he now works on AI solutions at Element Materials Technology. He brings a calm, grounded way of working that only comes from years spent facing ambiguity head on. 

Call to Action 

If Rick’s stories helped you feel a little less alone in the chaos of product work, stick around. Subscribe, share the episode with someone who’s grappling with change of their own, or reach out if you’ve got a story that deserves some daylight. Product work is rarely tidy, but it goes down easier when we learn from each other. 

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” taped around the room like a horror‑movie timeline and had to help the organization face the truth about impossibility. And the moment she realized she was about to pass along the very harm she was receiving from an overwhelmed manager and had to ask herself, “What kind of leader do I want to be?” 

What follows is an honest, funny, and surprisingly comforting look at how balance, empathy, humor, and human limits shape the work we do. Katie talks openly about burnout, unreasonable expectations, why saying no is an act of care, and how creativity survives only when we give ourselves actual space to think. 

If you’ve ever felt stretched thin or stuck between competing demands, this one might feel a little too real in the best possible way. 

Quotable Moments 

• “Stressed‑out, burned‑out people in back‑to‑back meetings all day do not have aha moments.” 
• “You can’t compare a release candidate to the car you drive off the lot. You compare it to the first prototype that probably didn’t even start.” 
• “Once a team learns to expect failure, you’ve lost the project. Getting that horse back in the stable is nearly impossible.” 

About the Guest 

Katie Tamblin is a seasoned data and software advisor with more than twenty years leading product, data science, technology, and marketing teams. She’s also the author of The Lean-Agile Dilemma and someone who has lived through more than a few “how did we get here” product moments. 

Call to Action 

If this episode made you feel a little more normal in the chaos of product work, you’re in good company. Subscribe, share it with a teammate who’s quietly drowning under too many priorities, or pass it along to the person who needs to hear that saying no is not a moral failing. Real product stories travel best person to person, usually over a much‑needed cup of coffee. 

Resources Mentioned 

• Dr. Todd Rose – Collective Illusions 
• Mentioned in Katie’s discussion about conformity, belonging, and self‑silencing. 
• Collective Illusions — Todd Rose
• Katie Tamblin’s book – The Lean-Agile Dilemma 
• Discussed in relation to balance, team culture, and the difficulty of saying no. 
• Katie Tamblin | Lean-Agile Dilemma

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 poured his whole identity into began losing steam and what it meant to walk away from a dream with no backup plan except “maybe I should get a computer job.” He talks about the moment he first saw a command execute on a remote machine, a tiny spark of wonder that would eventually pull him into NASA, startups, and finally product management. 

Along the way we explore the late‑in‑life discovery that helped him make sense of all those turns, the surprising lessons buried in punk‑rock logistics, and the hard‑won understanding that you don’t need to be a superhero to make a difference. Sometimes your 3 percent of influence is enough. 

This is an episode about reinvention, humility, agency, and finding meaning in the mess. 

A warm, honest conversation for anyone who’s ever looked at their path and thought: 

“How did I end up here… and does it all matter?” 

 Spoiler: it does. And Scott tells us why. 

Quotable Moments 

• “A song is a product led growth thing. You can’t really force somebody to listen to it.” 
• “You might only have control over three percent of the problem, but if that three percent is impactful, then do it.” 
• “There’s not really a way to hack your way to better. You just learn what you learn.” 

About the Guest 

Scott McCarty is the Global Senior Principal Product Manager for Red Hat Enterprise Linux. His path from punk‑rock basements to enterprise software leadership is shaped by curiosity, resilience, and a willingness to step into the unknown. After roles in sysadmin work, NASA, startups, sales, and product marketing, he found his home in product management, where he helps guide one of the most widely used Linux platforms in the world. 

Call to Action 

If Scott’s story rings true to your own winding journey in product work, share this episode with someone who might need that same bit of encouragement today. Subscribe and leave a quick review so more real product stories can find the people who need them. And if you’ve got a messy path or hard‑earned lesson of your own, reach out. Productly Speaking is where stories like yours finally get their space. 

Resources Mentioned 

• Ikigai (concept overview) 
• https://en.wikipedia.org/wiki/Ikigai  
• Red Hat Enterprise Linux (product page) 
• https://www.redhat.com/en/technologies/linux-platforms/enterprise-linux  
• Podman (official site) 
• https://podman.io/  
• Podman Desktop (official site) 
• https://podman-desktop.io/  
• CNCF project listing for Podman Desktop 
• https://www.cncf.io/projects/podman-desktop/  
• NASA (homepage) 
• https://www.nasa.gov/  
• American Greetings 
• https://www.americangreetings.com/  
• Telnet (protocol overview) 
• https://en.wikipedia.org/wiki/Telnet  
• The Power of the Powerless by Václav Havel (StoryGraph) 
• https://app.thestorygraph.com/books/4a76f11a-8ad8-4f9e-976c-3e5e28d1766d  
• Scott’s writing 
• Educated Confusion: http://educatedconfusion.com/  
• Crunchtools: https://crunchtools.com/about/  
• Red Bull Rampage (event page) 
• https://www.redbull.com/int-en/events/red-bull-rampage  

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.

This season features conversations with Scott McCarty, Katie Tamblin, and Rick Lewis, and closes with a conversation about values, integrity, and authenticity in leadership with Reese Gifford.

I slowed the show down this season, reworking the sound and flow to make space for more honest, reflective conversations, the kind you usually only have after the meeting ends.

No frameworks.

No polished PM stories.

Just real people talking about what actually happened and what it taught them.

Season 5 launches April 14th, with new episodes released weekly.

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 the moment she realized AI was not a mysterious genius but also definitely not “just matrix math,” either.

Along the way, she tells a surprisingly relatable story about learning to solve a Rubik’s Cube, and why that experience changed how she thinks about intelligence, perception, and expectation‑setting with stakeholders. They also dig into the emotional side of AI adoption, including the fear of being made redundant, the discomfort around privacy and environmental impact, and the quiet tension PMs feel when bold visions collide with very incremental progress.

This is a grounded, honest conversation about hype, disillusionment, and what it takes to keep building thoughtfully when everyone else wants miracles. If you have ever felt caught between excitement and skepticism, or responsible for translating big promises into something real, this one will hit close to home.

Productly Speaking: where product management gets real.

Key Quotes: 

• “Not understanding the problem is a huge one… especially in the AI space.” 
• “AI isn’t thinking. It’s predicting the next word.” 
• “Bring back engineers being lazy! What is the minimum we can do to solve this problem?” 
• “Nobody achieves anything significant alone.” 

Resources & References: 

• Gartner Hype Cycle: https://www.gartner.com/en/research/methodologies/gartner-hype-cycle  
• Freytag’s Pyramid: https://writers.com/freytags-pyramid  
• Tools mentioned:  
• GitHub Copilot: https://github.com/features/copilot  
• Lovable: https://lovable.dev/  
• V0: https://v0.app/  
• Cursor: https://cursor.com/  

Connect with Dina Atia: 

https://www.linkedin.com/in/dinaatia/  

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 is real, the workload never quite matches the capacity, and the fear hums in the background more often than anyone likes to admit.

They also dig into a surprisingly emotional story about “dogfooding” your own product. Jake reflects on the moment he stepped away from a product he had lived inside for years and started using the market leader instead. What he discovered was uncomfortable, eye‑opening, and deeply human. Features he once dismissed as nice to have suddenly became things he felt he could not live without. It forced him to confront how easy it is to lose empathy when familiarity turns into tunnel vision.

This conversation is about curiosity, humility, and the emotional attachments users form that never show up neatly in a backlog. If you have ever felt stretched too thin, questioned your own assumptions, or realized a little too late that users care about things you overlooked, this episode will feel uncomfortably familiar, in the best possible way.

Key Quotes 

• “We as product managers… should probably be trying to use where we can our own products that we're building… But when I started using our biggest competitor… I suddenly realized a lot of things that I had probably just missed.” 
• “When they spoke to me about features, it was very easy for me to dismiss those as nice-to-haves… When actually, I quickly realized once I started using them that I got a very strong emotional attachment to them.” 
• “If the decision is made, communicated, and explained, it can be a pretty mediocre decision because it’s still better than a decision that hasn’t been made, communicated, or explained.” 

Resources Mentioned 

• Inspired — Marty Cagan (https://app.thestorygraph.com/books/dec05575-b75f-4127-b00f-0b44af6f1724) 
• Crossing the Chasm — Geoffrey Moore (https://app.thestorygraph.com/books/db6bfb5d-0747-4576-a487-47989e928167)  
• Jake’s website: https://jakebowen-bate.co.uk/  
• Jake on LinkedIn: https://www.linkedin.com/in/jakebowenbate/  

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 everything she knew about building new products simply did not apply to replacing systems that people depended on every single day.

She tells a vivid replatforming horror story where a team got all the way to the brink of launch, only to discover that almost none of the real data actually worked in the new system. What followed was not a quick fix, but an 18‑month delay, a lot of stress, and some very uncomfortable conversations. Along the way, she explains why customers will never happily “move into a tent” while you rebuild their house, no matter how optimistic the plan sounded on a slide.

This is an honest, empathetic conversation about pressure, misalignment, investor expectations, and the emotional toll of trying to modernize systems without breaking trust. If you have ever felt stuck between how product work is supposed to look and how it actually feels inside a big organization, this episode will make you feel very seen.

Featured Quote: 

"Lean and Agile were designed for building software for the first time that no one’s using yet. Chunky corporates are managing decades of existing products and data—that’s a completely different beast." – Katie Tamblin 

What You’ll Learn in This Episode: 

• Why lean and agile principles break down in large organizations 
• The MVP myth in replatforming (and Katie’s “tent in the garden” analogy) 
• How data migration becomes the biggest gremlin in product transformations 
• The illusion of agility and why sprints don’t guarantee success 
• Practical advice for PMs in startups vs. complex enterprises 

Resources & Links: 

• Katie’s Book: The Lean Agile Dilemma (https://link.springer.com/book/10.1007/979-8-8688-0321-5) 
• Katie’s Website: www.katietamblin.com 
• Subscribe to Productly Speaking: www.productlyspeaking.com 

 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 he learned the consequences the painful way, more than once.

They also revisit a moment when a product seemed completely dead on arrival. While working on an internal chatbot platform with almost zero adoption, Lee chose an uncomfortable path and reshaped how the product showed up for its users. That shift did not come from clever ideas, but from paying attention to how people actually worked and what they needed help with, even when it conflicted with how the product was “supposed” to be used.

Along the way, the conversation touches on humility, messy communication, navigating difficult personalities, and why product management is ultimately about people, not artifacts. If you have ever felt the weight of unclear expectations, second-guessed a decision after making it, or wondered how much of this job is really about human relationships, this episode will feel like a knowing nod rather than a lecture.

Key Quotes: 

• “A product manager’s job is to move her product forward to best serve the interests of its users and the business. Inside the organization, she represents the product.” 
• “You don’t get paid to manage chaos. You get paid for the skills you bring while facing a chaotic situation.” 
• “Product management is about people—the people who use your product, the folks you work with, the men and women you report to. If you want to excel, double down on all the ways you work with and value people.” 
• “You can build your own market, but then some advancement’s going to come in where all of a sudden that’s no longer a need what you service. If you don’t stay ahead and reinvent yourself over and over, you find yourself in a bad spot.” 

Resources & Links: 

• Lee Fischman on LinkedIn: https://www.linkedin.com/in/lee-fischman/  
• Lee’s Book: How to Excel at Digital Product Management (https://www.amazon.com/Excel-Digital-Product-Management-comprehensive/dp/B0DPVNX178/) 
• Lee’s Medium: https://medium.com/@lee.fischman  

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 and help you think differently about success and failure! Subscribe so that you don't miss an episode!

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 “just move everything over by a month.” It was not a tooling problem. It was a human one.

That realization led to a rethink of what roadmaps are actually for and a format that gave teams permission to be honest about uncertainty without losing credibility. Janna reflects on the tension of showing direction without false precision, the pressure to make promises you cannot keep, and the relief that comes when stakeholders finally see a roadmap as a conversation instead of a contract.

This is a warm, candid conversation about trust, expectation‑setting, and why product work so often feels like balancing honesty with survival. If you have ever felt anxious presenting a roadmap, exhausted by shifting dates, or quietly blamed yourself for things slipping, this episode will feel like a breath of fresh air.

Key Quotes

• “Roadmapping is a strategic communication exercise—not a delivery promise.”
• “If everything on your roadmap has a date, you’re not doing product management—you’re doing project delivery.”
• “AI won’t replace product managers, but it will replace the grunt work.”
• “Good product management isn’t just done by a product manager sitting in the corner… it’s their job to surround themselves with people in the team and ask really good questions and be transparent about the direction of the product.”

Learn More

• ProdPad
• Mind the Product

Connect with Janna

LinkedIn - https://www.linkedin.com/in/jannabastow/

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 the very human tension between keeping Firefox open and free while still figuring out how to keep the lights on.

She tells candid stories about moments where product decisions sparked community backlash, including the pushback around Firefox accounts and monetization efforts that made sense for the business but felt uncomfortable for users who believed everything should remain untouched. These were not abstract tradeoffs. They were emotional, public, and deeply personal conversations about trust, privacy, and sustainability.

This is an honest look at product management without a clear chain of command, where influence matters more than authority and where doing the “right” thing rarely pleases everyone. If you have ever struggled to balance ideals with reality, or felt the weight of decisions that affect people far beyond your org chart, this conversation will stay with you.

Key Quotes:

• “Open source has gone from a niche grassroots movement to the foundation of modern software development.”
• “Product management in open source is harder—your stakeholder base is vast and deeply involved.”
• “The community has a massive influence… decisions have to be driven from a consensus of multiple stakeholders, including external contributors.”

Advice for Aspiring Open Source PMs:

• Embrace the complexity of community-driven development.
• Communicate clearly with both internal teams and external contributors.
• Understand that prioritization decisions require diplomacy and transparency.

Connect with Reese:

LinkedIn: https://www.linkedin.com/in/marissaponikvar/

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 deciding someone had to fix it. No role, no playbook, just curiosity and a willingness to tinker until something worked.

Ali also tells the deeply personal story behind his book, Make Pigs Fly, and why it was written to be read in stolen moments of quiet. As an immigrant learning English through short, memorable phrases, he explains how storytelling and simple language became survival tools long before they became professional skills. Along the way, he reflects on burnout, learning to say no, telling bad jokes that no one laughs at, and why confidence is built by failing in public and coming back anyway.

This is a warm, honest conversation about blue‑collar product work, the courage to ask “dumb” questions, and why the best PMs are builders at heart. If you have ever felt like you did not belong, struggled to be understood, or wondered whether you were doing product “the right way,” this episode is a reminder that showing up, trying, and caring still counts for a lot.

About the Book

• Title: Make Pigs Fly: Product Manager’s Bathroom Book
• Where to Buy:
• Ali’s Website
• Amazon
• IngramSpark

Key Quotes

• “I didn’t stumble into product management—I tripped, fell, and landed face-first into it.”
• “You don’t need to speak louder—you just need to translate better.”
• “Good PMs ship features. Great PMs ship belief.”
• “You have to be fearless. You have to be hungry. That’s how you grow.”

Connect with Ali

LinkedIn: https://www.linkedin.com/in/arakhimov/

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 survives when the rules change every week. That experience, it turns out, translated surprisingly well into product work.

She also reflects on discovering the PM role for the first time through a Microsoft program led by two women who helped her see that big‑picture thinking, empathy, and curiosity mattered just as much as technical depth. From volunteering in healthcare to working on Azure Linux with teammates spread across the world, Flora talks candidly about learning where she adds the most value and how customer impact became her guiding motivation.

The conversation digs into the lived reality of working on truly distributed teams, where video calls are the office, hallway conversations have to be intentional, and showing up on camera can make the difference between connection and isolation. Flora also shares how AI tools have quietly changed her day‑to‑day work, not by replacing judgment, but by helping her stay present, ask better questions, and move faster without burning out.

This is a thoughtful, grounded episode about finding your way into product, building trust at a distance, and learning that the skills you pick up in unexpected places often matter more than the ones you think you’re missing.

Key Quotes

• “I think that empathy and creative problem solving and satisfying customer needs are all deeply transferable skills.”
• “I found it very valuable to spend the first few minutes of my one-on-ones with my fully remote colleagues, just chatting and catching up and not jumping straight into work.”
• “Even if some team members are physically in person in a conference room together, I really appreciate when everyone still joins the Teams call individually and turns on their camera.”

Resources Mentioned

• Cracking the PM Interview by Gayle Laakmann McDowell & Jackie Bavaro
• Cloud Native Computing Foundation (CNCF) for open source contributions
• Microsoft Teams, GitHub Copilot, and other AI productivity tools

Connect with Flora

LinkedIn – Flora Taagen -- https://www.linkedin.com/in/florataagen/

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. It wasn’t until much later, sitting in a tiny meeting room with a manager and a PM, that the pieces finally clicked.

Adil reflects on coming from customer support, spending his days on the phone with real users, hearing frustrations firsthand, and mentally sketching how he would fix things if the product were his. That experience shaped how he thinks about saying no, telling better stories, and carrying responsibility once you’re no longer allowed to quietly promise “we’ll add it to the backlog.”

The conversation also weaves through Adil’s time in government and the private sector, including a moment helping his mum renew her passport online that crystallized what good digital services can feel like when they actually work. Along the way, he talks candidly about mentoring aspiring PMs, breaking down buzzwords into plain language, and why real product work looks nothing like the polished posts you see online.

This is a warm, grounded episode about learning product by doing it, caring deeply about users, and discovering that the most valuable skills often come from places that don’t look like “product” at all.

Resources Mentioned

• GOV.UK Design System
• UK Government Digital Service (GDS)
• GDS Service Standard
• GDS Product Management Capability Framework

Key Quotes

• “Product management for me is about solving those problems in the right way and also making sure that we're building really good user experiences.”
• “I come across people that I mentor, that I teach or just have normal conversations with who aspire to break into product… and don’t realize they’re already doing product-style thinking.”
• “Being able to tell good stories as a product manager and being able to tell a narrative… it’s very, very important.”

Connect with Adil

Interested in Adil’s bootcamp or mentorship?

Reach out to him on LinkedIn - https://www.linkedin.com/in/adilh1/

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 from excitement to fear. What once felt creative and energizing turned into pressure, scarcity, and constant mental noise, all while juggling a new baby and very little sleep.

He reflects candidly on the moment he realized most of his stress wasn’t coming from what was actually happening, but from the stories he was telling himself about the future. From there, Kevin describes how learning mental performance tools normally reserved for elite athletes changed how he handled uncertainty, setbacks, and the constant weight of leadership.

The conversation explores what it feels like to live in fight‑or‑flight at work, why negativity can take over even when things look “successful” from the outside, and how small shifts in awareness can help you get back to doing your best work instead of just surviving the day. If you’ve ever felt stuck in your own head, exhausted by the pressure to perform, or worried that burnout is becoming your default state, this episode will feel uncomfortably familiar in the best possible way.

Quotes: 

"The vast majority of our stress is perceived stress. If you're, you know, on a bench press or something trying to put up your max weight, that's going to be real stress in the moment. But the vast majority of our stress is fear of the future, rumination on the past."  

"In order to be able to get into flow state, you have to be able to recognize what pulls you out of flow state."  

Guest Information: 

• Kevin Bailey: Founder and CEO of DreamFuel Coaching 
• Website: https://www.dreamfuel.com/ 
• LinkedIn: Kevin Bailey 
• Podcast: The DreamFuel Show 

Call to Action: 

• Visit DreamFuel's website to learn more about their coaching services. 
• Connect with Kevin Bailey on LinkedIn for insights on mental performance. 
• Subscribe to The DreamFuel Show for more discussions on mental health and performance.