Corporate Underpants

E7 AUDIO Mike Neff on Puzzle Perspective and Decoding Leadership Behavior

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 everything right” isn’t enough
• How to spot invisible misalignment before it wrecks your roadmap
• Using design tools to align stakeholders (not just users)
• What to ask when nothing makes sense
• Why puzzle perspective is a leadership superpower

If you're a designer, PM, or exec trying to make a real impact in a complex org—this one’s for you.

E7 VIDEO Mike Neff on Puzzle Perspective, Leadership Blind Spots, and Asking the Right Questions

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 everything right” isn’t enough
• How to spot invisible misalignment before it wrecks your roadmap
• Using design tools to align stakeholders (not just users)
• What to ask when nothing makes sense
• Why puzzle perspective is a leadership superpower

If you're a designer, PM, or exec trying to make a real impact in a complex org—this one’s for you.

E6 AUDIO Melissa Appel on the Magical Powers of Alignment

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. We also delve into practical tools like alignment personas and stakeholder canvases, and offer advice for those looking to make impactful changes within their organizations.

 

02:06 Meet Melissa Appel!

03:18 Meeting Bruce & Writing Aligned

06:04 "Us Vs. Them" Mentality

07:38 Mining for conflict (even when you have clear goals)

09:27 Seniority means becoming a stakeholder manager

10:53 Underpants Story: A 'delivery' problem was actually a 'culture' problem.

16:06 Melissa's two-pronged approach: quick fixes plus longer-term culture shifts

19:35 Find champions by figuring out individuals' goals

20:40 The bad apples & two kinds of assholes

25:19 Glossaries: the unsung heroes of alignment

27:36 Being brave enough to say "let me get this straight..."

30:58 How to tweak the language you use to get results

33:14 How Alignment Personas fit with Aligned the Book

39:42 Get Melissas & Bruce's Free Stakeholder Canvas

45:07 Politics vs Alignment vs Agreement vs Acceptance

49:02 How Melissa builds roadmaps

50:50 Melissa's Pre-Quit Checklist For Changing Jobs

S1E6 VIDEO Melissa Appel on the Magical Powers of Alignment

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. We also delve into practical tools like alignment personas and stakeholder canvases, and offer advice for those looking to make impactful changes within their organizations.

 

02:06 Meet Melissa Appel!

03:18 Meeting Bruce & Writing Aligned

06:04 "Us Vs. Them" Mentality

07:38 Mining for conflict (even when you have clear goals)

09:27 Seniority means becoming a stakeholder manager

10:53 Underpants Story: A 'delivery' problem was actually a 'culture' problem.

16:06 Melissa's two-pronged approach: quick fixes plus longer-term culture shifts

19:35 Find champions by figuring out individuals' goals

20:40 The bad apples & two kinds of assholes

25:19 Glossaries: the unsung heroes of alignment

27:36 Being brave enough to say "let me get this straight..."

30:58 How to tweak the language you use to get results

33:14 How Alignment Personas fit with Aligned the Book

39:42 Get Melissas & Bruce's Free Stakeholder Canvas

45:07 Politics vs Alignment vs Agreement vs Acceptance

49:02 How Melissa builds roadmaps

50:50 Melissa's Pre-Quit Checklist For Changing Jobs

 

E5 VIDEO: A Lively Debate About Things We (Mostly) Agree On with Jared Spool

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 anyone knew why it mattered.

Then we get into the real stuff:
⚡ Why proving UX’s value is still an uphill battle (and what to do about it)
⚡ How business metrics—not just usability—can make UX indispensable
⚡ How to stop waiting for a seat at the table and make leadership pay attention

Jared also casually drops the fact that he accidentally invented voicemail (oops), helped define the way we use keyboards, and somehow made usability testing sound fun. If you’ve ever had to fight for UX, justify your work, or convince execs to stop launching terrible products, you need this episode.

04:24 Jared's Early Badassery: The 70's and 80's

07:15 The Era of "Computer Operators"

09:49 The First Word Processors in the Era Before UX

13:27 Jared Accidentally Invents Voicemail

17:06 Getting People To Think About "Users"

18:23 Early 2000's: The First Research Into "What Makes A Good Website?"

21:05 The Trick: What Does Great UX Mean To Your Team or Org?

23:40 De mocratization vs. Delegation

25:14 The First Usability Lab

30:39 Jared's Work Today: How To Get A Seat At The Table

31:26 We Know How To Design Things. So Why Are Things Still Poorly Designed?

32:31 The 2010s' Boom: 6,221 Days Without Becoming a Bank

36:12 Our Snobbishness About "The Bottom LIne"

38:28 The Face Weasel

38:58 How To Become Hyper-Valuable To Mount Olumpus

41:59 Tamara And Jared Argue Over Job Titles

43:12 How To Become Powerful In An Organization

46:49 Leaders Of Awesomeness Helps You Become Undeniably Valuable

48:30 Pro-tip: Metrics Aren't "Numbers." They're "Measuring Change."

49:22 Shifting from Tactical Research to Strategic Research

E5 AUDIO: A Lively Debate About Things We (Mostly) Agree On with Jared Spool

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 anyone knew why it mattered.

Then we get into the real stuff:
⚡ Why proving UX’s value is still an uphill battle (and what to do about it)
⚡ How business metrics—not just usability—can make UX indispensable
⚡ How to stop waiting for a seat at the table and make leadership pay attention

Jared also casually drops the fact that he accidentally invented voicemail (oops), helped define the way we use keyboards, and somehow made usability testing sound fun. If you’ve ever had to fight for UX, justify your work, or convince execs to stop launching terrible products, you need this episode.

04:24 Jared's Early Badassery: The 70's and 80's

07:15 The Era of "Computer Operators"

09:49 The First Word Processors in the Era Before UX

13:27 Jared Accidentally Invents Voicemail

17:06 Getting People To Think About "Users"

18:23 Early 2000's: The First Research Into "What Makes A Good Website?"

21:05 The Trick: What Does Great UX Mean To Your Team or Org?

23:40 De mocratization vs. Delegation

25:14 The First Usability Lab

30:39 Jared's Work Today: How To Get A Seat At The Table

31:26 We Know How To Design Things. So Why Are Things Still Poorly Designed?

32:31 The 2010s' Boom: 6,221 Days Without Becoming a Bank

36:12 Our Snobbishness About "The Bottom LIne"

38:28 The Face Weasel

38:58 How To Become Hyper-Valuable To Mount Olumpus

41:59 Tamara And Jared Argue Over Job Titles

43:12 How To Become Powerful In An Organization

46:49 Leaders Of Awesomeness Helps You Become Undeniably Valuable

48:30 Pro-tip: Metrics Aren't "Numbers." They're "Measuring Change."

49:22 Shifting from Tactical Research to Strategic Research

E4 Part 2 AUDIO: Alignment in Higher Ed: A Tale of Two Projects

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 about why clarity on business goals is everything, how to get stakeholders on board early, and why adaptability is your secret weapon when dealing with large, bureaucratic orgs.

If you’ve ever been stuck in a project with 40 stakeholders, changing priorities, and no clear direction—this one's for you.

Timestamps:

00:00 Corporate Underpants Live S1E4 – Managing 40 Stakeholders
01:45 Welcome!
04:27 Starting the next project with alignment
06:35 Asking for four days, getting four hours
07:53 What’s the actual goal here?
09:07 Overview of The Five Conversations
10:13 Adam’s zero-resistance feedback hack
12:47 Yes, you CAN meet hundreds of user needs
16:33 “Doing personas” whether they think they are or not
17:13 Why personas have a bad rap
18:56 Higher ed stakeholders actually talk to users—so their assumptions aren’t just “assumptions”
19:45 What about bias?
21:08 Proto personas, presumptive personas, alignment personas, archetypes… what’s the difference?
22:26 If your team hates personas, just don’t call them personas
23:03 HYPOTHESIS!
27:32 Everyone freaks out about stereotypes…
29:28  People have a hard time working together—this helps fix that
30:35 Four hours later, we had clear goals!
32:53 The result? Three months, under budget… and thank-you notes.
34:46 "Where’s the big red button?"
36:12 The Lifeboat
37:14 This work requires political capital
39:24 Start small!
41:11 The politics are always the hard part
51:47 Why agencies should bake alignment into their projects
52:08 Word choice makes a difference
53:37 Why goals never exist
58:22 Tech people need to adjust when working with nonprofits
59:43 Not everything can be fixed
01:05:07 Final thoughts

E4 Part 2 VIDEO Alignment in Higher Ed: A Tale of Two Projects with Adam Staffa

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 about why clarity on business goals is everything, how to get stakeholders on board early, and why adaptability is your secret weapon when dealing with large, bureaucratic orgs.

If you’ve ever been stuck in a project with 40 stakeholders, changing priorities, and no clear direction—this one's for you.

Timestamps:

00:00 Corporate Underpants Live S1E4 – Managing 40 Stakeholders
01:45 Welcome!
04:27 Starting the next project with alignment
06:35 Asking for four days, getting four hours
07:53 What’s the actual goal here?
09:07 Overview of The Five Conversations
10:13 Adam’s zero-resistance feedback hack
12:47 Yes, you CAN meet hundreds of user needs
16:33 “Doing personas” whether they think they are or not
17:13 Why personas have a bad rap
18:56 Higher ed stakeholders actually talk to users—so their assumptions aren’t just “assumptions”
19:45 What about bias?
21:08 Proto personas, presumptive personas, alignment personas, archetypes… what’s the difference?
22:26 If your team hates personas, just don’t call them personas
23:03 HYPOTHESIS!
27:32 Everyone freaks out about stereotypes…
29:28  People have a hard time working together—this helps fix that
30:35 Four hours later, we had clear goals!
32:53 The result? Three months, under budget… and thank-you notes.
34:46 "Where’s the big red button?"
36:12 The Lifeboat
37:14 This work requires political capital
39:24 Start small!
41:11 The politics are always the hard part
51:47 Why agencies should bake alignment into their projects
52:08 Word choice makes a difference
53:37 Why goals never exist
58:22 Tech people need to adjust when working with nonprofits
59:43 Not everything can be fixed
01:05:07 Final thoughts

E4 Part 1 AUDIO Navigating the Complexities of Digital Projects in Non-Tech Orgs with Adam Staffa

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 did was chaos due to misalignment. In part 2, you'll hear about the magic of stakeholder Alignment, alignment Personas, and clear goals! Hint: the second project came in early and under budget.

Have YOU ever gotten hate mail after launching? Adam has.
Have YOU ever turned that hate mail into thank-you notes within months? Adam has.

 

00:27 Welcome!  

05:14 We're going to start talking about the solution to underpants!

08:02 Introducing Adam Staffa

10:45 Stakeholders and Governance in Higher Ed Projects

11:46 Stakeholders in Higher Ed, and Understanding Governance

19:53 #The Value of Being One Step Behind

23:44 In higher ed, the pipeline is YEARS.

25:18 The Scale of Content is Mind-Boggling

26:47 A Story of Educational Underpants

32:38 No matter how successful a project is, if everyone doesn't think it was successful, it wasn't.

33:04 Stakeholders were popping up everywhere!

35:05 Endless Meetings = Jenga

36:29 How the  project  ended

E4 Part 1 VIDEO Navigating the Complexities of Digital Projects in Non-Tech Orgs with Adam Staffa

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 did was chaos due to misalignment. In part 2, you'll hear about the magic of stakeholder Alignment, alignment Personas, and clear goals! Hint: the second project came in early and under budget.

Have YOU ever gotten hate mail after launching? Adam has.
Have YOU ever turned that hate mail into thank-you notes within months? Adam has.

 

00:27 Welcome!  

05:14 We're going to start talking about the solution to underpants!

08:02 Introducing Adam Staffa

10:45 Stakeholders and Governance in HIgher Ed Projects

11:46 Stakeholders in Higher Ed, and Understanding Governance

19:53 #The Value of Being One Step Behind

23:44 In higher ed, the pipeline is YEARS.

25:18 The Scale of Content is Mind-Boggling

26:47 A Story of Educational Underpants

32:38 No matter how successful a project is, if everyone doesn't think it was successful, it wasn't.

33:04 Stakeholders were popping up everywhere!

35:05 Endless Meetings = Jenga

36:29 How the  project  ended

E3: A True Story of UX Democratization Gone Wrong (and a Solution!)

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 stock prices over UX maturity. Jillian shares how she built strong internal relationships by understanding the true needs of her stakeholders, organizing educational sessions, and advocating UX despite internal resistance and misalignment. Her narrative offers valuable insights for UX professionals on how to navigate organizational politics to achieve product success. 00:00 Corporate Underpants Live_ Episode 3_ A True Story of UX Democratization Go 03:40 Introducing Jillian! 05:44 What is UX Strategy? 06:16 Pisces Vesica 07:16 Diving int the story: Jillian got the job 09:02 No France for you! 11:24 And then they laid off most of the team. 12:30 Turns out, it was all about the stock price. 14:49 Jillian invited everyone to see her work - and found a fan! 18:05 How to build a UX Champion: "How can I help you?" 19:25 Discovering a whole team of "Systems Coaches" built to satisfy research cravings 21:28 "UX Democratization" in the wild 23:16 They were powerful, but they weren't trained. 26:07 If you can't beat 'em, train 'em: launching "UX Snacks" internally 28:12 Seeing results: building bridges with the system coaches 30:42 New thoughts on "UX Maturity" 33:50 Turning the UX lens on your own teams and company 36:32 Building more champions 38:43 Attract UX Champions with research bait 39:17 Networking skills are key 44:40 Lessons were learned.

E2: A True Story of One Sentence That Killed A Project

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.

E1: Are you ready to stop complaining about your org? With guest Scott Berkun

Are your Corporate Underpants showing? In this first episode of Corporate Underpants, we dive into the messy realities of workplace politics and uncover what it really takes to gain influence and grow as a product manager or designer. Learn from Scott’s journey as he reflects on the cultural biases that shape UX and product teams, why rigor isn’t always the answer, and how to align with decision-makers to drive meaningful impact. What’s Inside: Why some UX pros feel stuck while product managers rise. The truth about navigating workplace politics and egos. How to turn constraints into career growth opportunities.

💡 Take Action: If you’ve ever felt frustrated by the disconnect between your vision and your organization’s reality, this series is for you.

🔔 Subscribe for raw, actionable insights on mastering the underbelly of corporate life.