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The Power of Awkward Meetings

13 min

Finding Clarity, Camaraderie, and Progress

Golden Hook & Introduction

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Michelle: Okay Mark, I'm going to say the title of a business book, and you give me your brutally honest, one-sentence roast. Ready? Do Better Work. Mark: (Without missing a beat) Sounds like something my passive-aggressive boss would leave on my desk with a sticky note that just says "FYI." Michelle: That is painfully accurate. And I think most people would have that exact reaction. But what’s fascinating about Do Better Work: Finding Clarity, Camaraderie, and Progress by Max Yoder is that it was written by the CEO for his own team. It started as an internal guidebook at his software company, Lessonly, before it ever became a public book. Mark: Oh, so it’s not just theory. It’s been battle-tested in the wild. This isn't some consultant in an ivory tower. Michelle: Exactly. It's all about the real, messy, human stuff that happens day-to-day. And it’s become this quietly influential text in leadership circles, not because it won a bunch of fancy awards, but because readers find it so disarmingly simple and practical. It’s built on two core pillars: Camaraderie and Clarity. Mark: Camaraderie and Clarity. Okay, that sounds nice, but also a bit like a corporate poster. What does that actually mean in practice? Michelle: Well, that's the whole journey. Yoder argues that to get either of them, you have to go through some discomfort. And that’s where we’ll start. With the idea that the strongest teams aren't the ones that are always in harmony. They're the ones that have learned how to handle the tension.

The Antifragile Team: Building Camaraderie Through Conflict

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Mark: I’m already nervous. You’re saying a good team is supposed to have more tension? My entire career has been about avoiding awkward meetings and trying to keep the peace. Michelle: I think that’s most people’s experience! We see conflict as a sign of dysfunction. But Yoder reframes it completely. He pulls from this concept of 'antifragility,' which argues that some things don't just resist stress, they get stronger from it. Think about your muscles. Lifting weights is a form of acute stress, and the muscle repairs itself to be stronger than before. Mark: Okay, I get the gym analogy. But my team relationships don't feel like a bicep. They feel more like a wine glass. One wrong move and the whole thing shatters. Michelle: That’s because we treat them like they're fragile! Yoder’s point is that by avoiding every difficult conversation, by repressing every frustration, we create this chronic, low-grade stress that makes the relationship brittle. The alternative is to introduce small, manageable moments of acute stress—like being vulnerable or having a tough conversation—that actually build resilience. It makes the relationship antifragile. Mark: That sounds great in a book, but what does it look like in reality? I can’t just walk into my Monday morning meeting and announce all my deepest insecurities. Michelle: You don't have to. The book is full of these small, powerful stories. There's one that perfectly illustrates this. Yoder was at a summit with about twenty other software CEOs. The facilitator asks everyone to go around and share a professional highlight and a challenge from the past year. Mark: Let me guess. Everyone gave the standard, polished, humble-brag answers. "Our biggest challenge was just too much growth!" Michelle: You nailed it. For the first fourteen CEOs, it was exactly that. Guarded, professional, safe. Then it’s the fifteenth CEO’s turn, a guy named Sam. And instead of talking about revenue goals or market uncertainty, he just gets real. He says the last year had been incredibly hard for him personally, that things had "gotten pretty bad," and it had seriously affected his ability to lead. He even mentioned that cognitive therapy was what helped him get back on his feet. Mark: Whoa. In a room full of CEOs? That takes guts. I can just imagine the silence in that room. Michelle: There was a moment of it. But then something incredible happened. The five CEOs who spoke after Sam? Every single one of them dropped the corporate mask and shared their own personal struggles. And it didn't stop there. A few of the CEOs who had already given their "safe" answers asked if they could have a do-over. They wanted to share again, but this time, honestly. Mark: That's amazing. So one person's vulnerability basically gave everyone else permission to be human. Michelle: It was contagious. It changed the entire dynamic of the room from posturing to connecting. And that’s the core of Yoder’s argument. Vulnerability isn't a weakness; it's an invitation. It’s the catalyst for genuine camaraderie. It can be as simple as a leader saying, "I don't know the answer to that. What do you all think?" That one sentence can be more powerful than a hundred confident directives. Mark: I see the power in that story, I really do. But I also hear from a lot of readers and critics who say this isn't exactly a new idea. The whole vulnerability-as-strength concept has been a huge part of the cultural conversation for years, thanks to researchers like Brené Brown. What makes Yoder’s take feel different or more useful? Michelle: That’s a fair point, and it’s a common critique of the book—that it’s a great refresher but not groundbreaking. But I think Yoder’s contribution is in its radical practicality. He’s not focused on grand emotional confessions. He’s focused on tiny, repeatable behaviors. He talks about the "lone hero" myth, this idea we get from movies that a leader has to be a stoic genius who has it all figured out. Mark: The John Wayne or Steve Jobs archetype. Never apologize, never be wrong. Michelle: Exactly. And Yoder says the real heroes are the ones who can say, "I made a mistake," or "Can you explain that to me again? I'm not following." Or even just celebrating when someone else does something well. He’s taking this big, scary idea of 'vulnerability' and breaking it down into daily, five-second actions that anyone can take, which is probably why it worked so well as an internal guide at his own company. It's less about a philosophy and more about a playbook. Mark: A playbook for being a little more human at work. Okay, I can get behind that. It’s about building that trust, that camaraderie, so you can actually get things done together. Michelle: Exactly. So if vulnerability and difficult conversations build the trust to work together, the next piece is about building the process to work smart. And it starts with a principle Yoder learned from a soul-crushing failure.

The War on Waste: The Courage to Share Early

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Mark: A soul-crushing failure? Now you’re speaking my language. I learn more from disasters than successes. Michelle: Well, you’ll love this. Yoder introduces this idea he calls the "Duds vs. Gold" principle. He says every piece of work we do either ends up as a 'dud'—unused, unappreciated, basically a waste of time—or 'gold'—used, valued, and perfectly aligned with what was needed. Mark: And we’ve all produced our fair share of duds. I’m an expert dud-maker. Michelle: (Laughs) We all are. And Yoder argues that the primary reason we create duds is because we fall for another myth: "Leaders know the answer." We think we need to go away into a cave, perfect something, and then present our brilliant, finished work to the world. Mark: The grand reveal. Michelle: The grand reveal. And this is where his own story comes in. His first company was a software startup called Quipol. He was 22, full of vision, and he and his small team spent nine months—nine months!—working in a vacuum, perfecting every little detail of the software. They were convinced they knew exactly what the users wanted. Mark: Oh, I can feel where this is going, and it’s giving me anxiety. Michelle: They finally launch. He sends out the big "Quipol is here!" email. And minutes later, the first reply comes in. It says, "Congrats on the launch, but why doesn’t it do X?" And 'X' was this incredibly sensible feature that Yoder had never even considered. Mark: For nine months, he never thought of it. Ouch. Michelle: And that feedback kept coming. User after user pointed out obvious flaws or better ways of doing things. The feedback was gold, but it was too late. He had spent his entire development budget building the wrong thing. The company never recovered. It shut down in less than two years. He calls it a 'sloppy start' that was impossible to come back from. Mark: That is absolutely brutal. But I’ve lived that Quipol story on a smaller scale. I’ve spent three hours perfecting a single PowerPoint slide—massaging the font, aligning the graphics—only to show it to my boss and have her say, "You know, I don't think this slide adds to the presentation." And just like that, three hours of my life, up in smoke. It's the worst feeling. Michelle: It is! And Yoder’s solution is so simple, yet so hard to do. He says we need to replace the myth "Leaders know the answer" with a new one: "Leaders learn the answer." And the way you learn is by sharing before you're ready. Mark: That’s the title of the chapter, right? "Share Before You’re Ready." It’s terrifying. Sharing something that's half-baked or just plain bad feels like you're advertising your own incompetence. Michelle: It feels that way, but Yoder uses this brilliant analogy. He says, "Be like a sculptor." A smart sculptor doesn't carve a statue out of a massive block of marble and only ask for feedback when it's done. They make small, cheap models out of clay first. When the material is still wet and pliable, they show it to people. If someone says, "I think the chin needs more dimension," it's easy to fix. You just pinch the clay. Mark: But if you wait until the statue is cast in bronze… Michelle: Exactly. If you wait until it’s 'bronzed,' that feedback is useless. You can't change it. The project is a dud. He says we need to get feedback in the 'clay stages' of our work—when it's just an outline, a rough draft, a messy sketch on a whiteboard. Mark: Okay, that makes a lot of sense. But practically, how do you do it? How do you get over that fear of judgment? Michelle: He lays out a simple three-step process. First, spend no more than 30 to 60 minutes creating a very rough version—an outline, a wireframe, a few paragraphs. Second, get feedback from one or more trusted reviewers. And this is key: he says to pick people who will actually benefit from the project, who will challenge your ideas, and who have the time to help. A mix of veterans, newbies, superiors, and subordinates is ideal. Mark: So you're not just showing it to your work-bestie who will tell you it's great. Michelle: Definitely not. You need honest eyes. And the third step is to use that feedback to improve the project's direction and then repeat the cycle. He admits the process is simple, but mustering the courage to do it is the hardest part. You have to be vulnerable enough to show your messy work. Mark: Which brings us right back to the first topic. The two ideas are completely linked. You need the camaraderie and trust from being vulnerable to have the psychological safety to share your work before it's ready. Michelle: It's a virtuous cycle. And it all comes down to fighting what he calls the 'curse of knowledge'—the cognitive bias where, once you know something, it's hard to imagine not knowing it. You assume everyone has the same context you do. Sharing early forces you to confront that curse. Mark: That makes sense. But what happens if you get feedback you just don't agree with? Or the feedback is just... bad? You can't act on everything. Michelle: He addresses that directly. He says a "voice is not a vote." Especially for managers, it's important to hear people out, but you retain the final decision. The key is transparency. If you decide not to take someone's feedback, you should explain your rationale. It shows you respected their input enough to consider it seriously, which maintains that antifragile trust we were talking about. It’s about making sure what’s getting done actually matches what’s needed.

Synthesis & Takeaways

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Mark: So, when you put these two big ideas together—building that antifragile trust through vulnerability and fighting waste by sharing early—it seems like the core message of the whole book is that 'better work' is fundamentally about choosing to be uncomfortable. Michelle: I think that’s the perfect synthesis. It’s about choosing the acute, productive discomfort of a difficult conversation or sharing a rough draft, over the chronic, toxic discomfort of simmering resentment and wasted work. Yoder has this great metaphor of a 'scale of merit.' He says every action we take at work either tips the scale left, toward a setback, or right, toward progress. Mark: And things like pointing fingers or ignoring an issue tip it left. While keeping an agreement or, as we've discussed, being vulnerable, tips it right. Michelle: Exactly. And the whole book is a guide to behaviors that consistently tip the scale toward progress. It’s not about a massive, overnight transformation. It’s about small, intentional choices. Mark: And it's not about being perfect, either. I remember a line from the introduction that really stuck with me. Yoder says to approach this "1% at a time, with self-compassion." It’s about the direction, not the speed. You’re going to mess up, you’re going to fall back into old habits, and that’s okay. The goal is just to keep trying. Michelle: It’s such a humane approach to improvement. It’s not a hustle-culture manifesto. It’s a guide to being a more effective and collaborative human being, who also happens to have a job. It really makes you wonder, in our own work, what's one small, uncomfortable conversation or one half-finished idea we could share this week to tip that scale? Mark: That's a powerful question. And I think it's one our listeners can take with them. We'd love to hear your thoughts on this. Find us on our socials and share one small way you're planning to 'do better work' after hearing this. Let's get the conversation started. Michelle: I love that. Because as Yoder says in the end, our influence boils down to what we do and what we celebrate. This is Aibrary, signing off.

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