That time when an expert is brought in to build something complicated only to be questioned every step of the way by people who didn’t understand what they were doing…

I’m doing great. Thanks for having me.

We’ve conquered modern technology.

Perfect. I’m excited to share this one because it’s the kind of client horror story that fundamentally changed how I work. I’ve been doing client work for about 25 years, and over time all these experiences pushed me toward focusing almost entirely on early-stage alignment. This story comes from my work in the early blockchain space around 2017–2018. I was brought into a company through an investor recommendation, which meant I arrived with instant credibility: “She knows what she’s doing. Listen to her. She’ll help you build a better product faster.” That should have made things easier. It didn’t. Let’s call the company “Terrible Inc.” They were building tooling around smart contracts—essentially documents that contain code. Think of it like a document with embedded software. The whole idea was to help developers collaborate on these documents more easily. From the start, I did what I always do: I asked very basic, very hard questions. Who is this for? What problem are you solving? How will you know if this is successful? One thing I’ve learned is that when I’m confused, that’s a signal. If I don’t understand it, others won’t either. So instead of assuming I’m the problem, I lean into that confusion. They wanted to do everything all at once. I was trying to slow them down so they could actually speed up.

Exactly. And once you’ve lived deeply in a field—like I have with personas and UX—you reach a point where it’s not ego-threatening to say, “I don’t understand your question,” or “Can you clarify that?” Impostor syndrome dies accidentally when you actually know your craft. I came up through user experience and human-computer interaction. At its core, UX is translation—between business, technology, and users. If I can’t translate something into language a user understands, that’s not a me problem. That’s the problem. You also learn little verbal tricks. You can say, “I’m confused, and if I’m confused, others might be too.” Or, “Help me simplify this so I can explain it to users.” You’re appealing to their ego while forcing clarity.

Exactly. Vocabulary is another huge issue. People use the same words and mean totally different things. I once worked with founders who realized—after two days—that they didn’t even agree on what “institutional investor” meant. That was the entire problem. Anyway, back to Terrible Inc. This was peak blockchain hype. You said “blockchain” and investors threw money at you, just like AI today. These were young founders who had maybe shipped one product before, certainly never built a company—but now they were being told they were geniuses, with millions of dollars validating that belief before they’d built anything. That kind of early validation makes people completely closed to advice.

Absolutely. Everyone was rushing to be first, which we know is usually how you don’t win. Facebook wasn’t first. Neither was Google. I walked in with 15 years of successful consulting behind me, and I got knocked off my high horse fast. At one point, I said, “What are you working on right now?” They said the smart contract document itself. So I stripped everything down—black, white, and blue—no fancy UI. Just logic. One problem at a time. It worked beautifully. They loved it. I thought, “Great, now they trust me.” Immediately after, they said, “Next sprint, we want you to design the entire navigation system.” I said, “There isn’t a system yet.” They said, “Just take a stab at it.” I said no. Then they said, “We’ll just copy Google Drive’s UI.” That was the moment. I tried explaining that Google Docs doesn’t have software running inside documents the way their product did. You can’t just copy it. Their response was, “You’re frustrating us. You’re slowing us down.” They told me they’d just add another button to fix it. At that point, I realized I was dealing with a level of misunderstanding I hadn’t seen since the early 2000s. I tried to make myself more “usable” to them, but the more I tried, the more condescending, misogynistic, and ageist the comments became. Eventually, they said, “You don’t understand blockchain.”

Exactly. I hit a point of rage—not because I was arrogant, but because it was so illogical. I finally realized I was being asked to break the laws of physics. I told them, “I physically cannot give you what you’re asking for.” And I got fired. Or rather, “We don’t think we can work together anymore.” I agreed completely. That experience taught me something crucial: some founders you have to say no to before you even start. I call them “pre-disastered founders.” Like in The World According to Garp —the house that already had a plane crash into it. Unless founders have already failed hard, they won’t tolerate someone who slows them down to speed them up.

I watch how they listen. I let them pitch, because they’re stuck in pitch mode. Then I ask, “What’s worrying you?” If they can admit fear or uncertainty, we might work. If they say, “We’re super clear, we just need you to draw it,” I’m out. People tell you who they are if you let them. I also take jokes seriously. When people joke about their flaws, that’s often the truest signal of who they are.

I’ve also learned to be careful with teasing. A sharp brain and sharp tongue can hurt people, even if you think you’re joking. Not everyone has the ability to contextualize it later.

Exactly. It’s about puzzle perspective—understanding the board someone else is playing on. That applies to founders, teams, clients, everything. And that’s why alignment is now the center of my work. If someone is obsessed with the “hippopotamus on the homepage,” that’s not always a battle worth fighting.

Thank you so much. This was a lot of fun.

My podcast is called Corporate Underpants . It’s about the invisible forces—politics, personalities, misalignment—that derail products. If that sounds interesting, I’d love for you to listen.