Corporate Underpants

Corporate Underpants

Uncomfortable truths, hidden dynamics, and the messy underbelly of corporate life—welcome to Corporate Underpants, the podcast that pulls back the curtain on the challenges holding back great teams and ideas. Whether you’re a product manager, designer, or leader, this series is your guide to navigating office politics, aligning stakeholders, and tackling the organizational hurdles that stand between you and making a real impact.

Episodes

July 30, 2025 56 mins
Information architect and UX strategist Andy Fitzgerald joined me to talk about what happens when content systems reflect silos instead of shared understanding. We unpacked how messy navigation, broken taxonomies, and unclear content flows often reveal misalignment inside the org—not just design problems on the screen. We also talked about:
  • Using architecture to surface conflict
  • Why navigation is a trust signal
  • The difference ...
Mark as Played
Why do so many UX researchers end up doing the wrong work for the wrong reasons? In this episode of Corporate Underpants Live, I talk with Bill Albert—author of Measuring the User Experience and founding director of Bentley’s Design and Usability Center—about the sneaky ways research gets misused, the traps UX teams fall into, and how to start being strategic before you’re invited to be. We cover:
  • How research becomes a perfo...
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David Bland, co-author of *Testing Business Ideas*, joins Tamara Adlin for a candid conversation about what *actually* holds teams back from testing well, building great products, and aligning around a strategy that works. Spoiler: the biggest barriers aren’t lack of data—they’re misalignment, culture, and invisible power dynamics.

This episode digs into the difference between performing strategy and actually having one, why VC cu...

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Ever felt like the goals are fuzzy, the execs are fighting, and your roadmap is just a wish list? You're not alone. In this episode of Corporate Underpants Live, I talk with Bruce McCarthy, co-author of Aligned, about what really derails progress in product, UX, and leadership—and how to build alignment even when it feels impossible.  We cover:  💥 Why tornadoes = political power struggles  ⚠️ What to do when execs don’t agree (or ...

Mark as Played
Information architect and UX strategist Andy Fitzgerald joined me to talk about what happens when content systems reflect silos instead of shared understanding. We unpacked how messy navigation, broken taxonomies, and unclear content flows often reveal misalignment inside the org—not just design problems on the screen. We also talked about:
  • Using architecture to surface conflict
  • Why navigation is a trust signal
  • The difference ...
Mark as Played
Why do so many UX researchers end up doing the wrong work for the wrong reasons? In this episode of Corporate Underpants Live, I talk with Bill Albert—author of Measuring the User Experience and founding director of Bentley’s Design and Usability Center—about the sneaky ways research gets misused, the traps UX teams fall into, and how to start being strategic before you’re invited to be. We cover:
  • How research becomes a perfo...
Mark as Played

David Bland, co-author of *Testing Business Ideas*, joins Tamara Adlin for a candid conversation about what *actually* holds teams back from testing well, building great products, and aligning around a strategy that works. Spoiler: the biggest barriers aren’t lack of data—they’re misalignment, culture, and invisible power dynamics. This episode digs into the difference between performing strategy and actually having one, why VC cu...

Mark as Played

Ever felt like the goals are fuzzy, the execs are fighting, and your roadmap is just a wish list? You're not alone. In this episode of Corporate Underpants Live, I talk with Bruce McCarthy, co-author of Aligned, about what really derails progress in product, UX, and leadership—and how to build alignment even when it feels impossible. We cover: 💥 Why tornadoes = political power struggles ⚠️ What to do when execs don’t agree (or ...

Mark as Played
What if the real reason your product failed wasn’t the team or the timeline—but that you were solving the wrong puzzle entirely? In this episode, I talk with Mike Neff, a seasoned product design leader, about what happened when he joined a company headed for IPO—and discovered that everything he thought he knew about success, alignment, and leadership was just one small piece of a much bigger picture. We cover:
  • Why “doing ever...
Mark as Played
What if the real reason your product failed wasn’t the team or the timeline—but that you were solving the wrong puzzle entirely? In this episode, I talk with Mike Neff, a seasoned product design leader, about what happened when he joined a company headed for IPO—and discovered that everything he thought he knew about success, alignment, and leadership was just one small piece of a much bigger picture. We cover:
  • Why “doing ever...
Mark as Played
I quiz Melissa Appel, the co-author of 'Aligned,' on the intricacies of corporate misalignment and its impact on developing and launching successful digital products. We discuss the importance of stakeholder alignment, how to tackle internal politics, and various strategies to address misalignments effectively. Melissa shares insights from her work as a coach for product leaders and her extensive experience in product management. W...
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I quiz Melissa Appel, the co-author of 'Aligned,' on the intricacies of corporate misalignment and its impact on developing and launching successful digital products. We discuss the importance of stakeholder alignment, how to tackle internal politics, and various strategies to address misalignments effectively. Melissa shares insights from her work as a coach for product leaders and her extensive experience in product management. ...
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Oh. My. God. You guys. Jared Spool is on Corporate Underpants. 🎉

In this episode, I sit down with the Jared Spool to talk about UX, product, and—of course—the corporate messes that make our jobs way harder than they need to be. We kick things off by diving into the early, wild days of UX (back when “user experience” wasn’t even a thing), and Jared shares hilarious and infuriating stories about fighting for better design before any...

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Oh. My. God. You guys. Jared Spool is on Corporate Underpants. 🎉

In this episode, I sit down with the Jared Spool to talk about UX, product, and—of course—the corporate messes that make our jobs way harder than they need to be. We kick things off by diving into the early, wild days of UX (back when “user experience” wasn’t even a thing), and Jared shares hilarious and infuriating stories about fighting for better design before any...

Mark as Played

In this episode of Corporate Underpants, I sit down with Adam to dig into the messy world of early-stage alignment in higher ed and non-tech-first organizations. Spoiler: It’s nothing like working at a tech company.

Adam shares war stories from two major web strategy projects—one that went off the rails thanks to (surprise, surprise) misalignment, and another that actually worked (because alignment wasn’t an afterthought). We talk ...

Mark as Played

In this episode of Corporate Underpants, I sit down with Adam to dig into the messy world of early-stage alignment in higher ed and non-tech-first organizations. Spoiler: It’s nothing like working at a tech company.

Adam shares war stories from two major web strategy projects—one that went off the rails thanks to (surprise, surprise) misalignment, and another that actually worked (because alignment wasn’t an afterthought). We talk ...

Mark as Played
This is a great 2-parter, people. The first part is all about how uniquely challenging Higher Ed and other non-tech-first orgs for website strategist and product people. Adam shares his experiences working in higher education and other sectors, where unique and complex Governance structures, diverse stakeholder groups, and entrenched institutional politics create substantial obstacles. You'll hear about how the first big project he...
Mark as Played
This is a great 2-parter, people. The first part is all about how uniquely challenging Higher Ed and other non-tech-first orgs for website strategist and product people. Adam shares his experiences working in higher education and other sectors, where unique and complex Governance structures, diverse stakeholder groups, and entrenched institutional politics create substantial obstacles. You'll hear about how the first big project he...
Mark as Played

In this episode of Corporate Underpants, host Tamara Adlin delves into the complex relationship between politics and product success with guest Jillian Hudson, a seasoned UX researcher and strategist. Through Jillian’s story, we learn about the unexpected challenges she faced when hired for a role that didn't match the initial promise, working under a manager who was often absent and dealing with a company in chaos prioritizing sto...

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Jeff Verona recounts the chaos caused by hidden misalignments and untested assumptions that ultimately derailed an initiative to streamline loan officer workflows. Woven into Jeff's tale are seven actionable "gems" that can help you spot and fix the kind of problems that left his team reeling.
Mark as Played

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