Corporate Underpants

S1E7 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.

S1E6 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
 

S1E5 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

S1E5 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

S1E4 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 Stakeholders01:45 Welcome!04:27 Starting the next project with alignment06:35 Asking for four days, getting four hours07:53 What’s the actual goal here?09:07 Overview of The Five Conversations10:13 Adam’s zero-resistance feedback hack12:47 Yes, you CAN meet hundreds of user needs16:33 “Doing personas” whether they think they are or not17:13 Why personas have a bad rap18:56 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 personas23:03 HYPOTHESIS!27:32 Everyone freaks out about stereotypes…29:28  People have a hard time working together—this helps fix that30:35 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 Lifeboat37:14 This work requires political capital39:24 Start small!41:11 The politics are always the hard part51:47 Why agencies should bake alignment into their projects52:08 Word choice makes a difference53:37 Why goals never exist58:22 Tech people need to adjust when working with nonprofits59:43 Not everything can be fixed01:05:07 Final thoughts

S1E4 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 Stakeholders01:45 Welcome!04:27 Starting the next project with alignment06:35 Asking for four days, getting four hours07:53 What’s the actual goal here?09:07 Overview of The Five Conversations10:13 Adam’s zero-resistance feedback hack12:47 Yes, you CAN meet hundreds of user needs16:33 “Doing personas” whether they think they are or not17:13 Why personas have a bad rap18:56 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 personas23:03 HYPOTHESIS!27:32 Everyone freaks out about stereotypes…29:28  People have a hard time working together—this helps fix that30:35 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 Lifeboat37:14 This work requires political capital39:24 Start small!41:11 The politics are always the hard part51:47 Why agencies should bake alignment into their projects52:08 Word choice makes a difference53:37 Why goals never exist58:22 Tech people need to adjust when working with nonprofits59:43 Not everything can be fixed01:05:07 Final thoughts

S1E4 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