Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Manage a Boss Who Is Never Wrong
Transcript
- Lucas: So I want to start with a number: four hundred thousand dollars. Luna: That's a big number. What's it attached to? Lucas: It's the value of a deal that a VP of Sales at a mid-size SaaS company let die last quarter. The deal was essentially closed — the client had verbally committed, legal had signed off — but at the last minute, the client asked for a minor scope change that would have shifted the delivery timeline by about two weeks. Luna: Okay, that sounds like a normal negotiation. Why did the deal die? Lucas: Because the VP had told the client, quote, 'We never adjust scope mid-contract.' Which wasn't true — the company had done it three times that quarter alone. The account executive pointed this out privately, and the VP's response was: 'I said what I said. If you push back again, you're insubordinate.' The client walked. Luna: So the VP would rather lose four hundred thousand dollars than admit they were wrong. That's the 'never wrong' boss in action. Lucas: Exactly. And I think this is one of the most corrosive dynamics in any workplace — a boss who treats being corrected as a personal attack. Today we're going to talk about how to manage that person without getting fired, and also when you need to accept that you can't. Luna: Before we go further — let's be clear about who this boss is. Because I think there's a difference between a boss who's confident and decisive and a boss who is pathologically never wrong. How do you distinguish? Lucas: Great question. A confident boss says, 'I think this is the right call. Convince me otherwise.' A never-wrong boss says, 'This is the call. Do not question it.' The key difference is openness to information. The never-wrong boss treats every fact that contradicts them as a threat. Luna: And often that fragility comes from a place of insecurity. I've read research that suggests managers who are the least competent are actually the most likely to overestimate their abilities and resist feedback. Lucas: That's the Dunning-Kruger effect, and yes, it plays a role. But I think there's a more specific dynamic at play in these cases: the boss has built their identity around being the authority, and any crack in that facade feels like career death. So they double down. Luna: Which is exhausting for everyone below them. So what do you actually do? The classic advice is to pick your battles, but that feels like a cop-out. Lucas: It's not a cop-out — it's triage. But I want to offer a more specific technique. I call it 'strategic self-correction.' Luna: Okay, I'm listening. What does that look like in practice? Lucas: So let's go back to that SaaS VP. The account executive could have said: 'You know, I initially agreed with your position that we shouldn't adjust scope — I was wrong. Looking at it again, I think there's a way to make this work that actually protects our process. Here's what I'd suggest.' Luna: So you're taking the blame for the disagreement, even though the VP was the one who made the mistake. Lucas: Exactly. You're giving the boss a way to reverse course without having to say 'I was wrong.' You're saying 'I was wrong' instead. And then you offer a solution that lets them claim it as their idea or their permission. Luna: That feels manipulative. And also — doesn't it just reinforce the behavior? You're teaching the boss that if they refuse to admit mistakes, someone else will clean it up. Lucas: That's the trade-off. And you're right — it's a short-term survival tactic, not a long-term fix. But sometimes you need to save a four-hundred-thousand-dollar deal, and you can't fix the boss's psychology in that moment. Luna: I want to come back to that tension. But first — I know we don't run ads on this show, and I think that's worth saying out loud. If this kind of concrete, no-fluff career advice has helped you navigate a tough situation, you can support the show at buy me a coffee dot com slash fexingo. It's how we stay independent and ad-free. Lucas: Yeah, and we mean it — no sponsors, no product pitches, just the conversation. If you find value in that, the link is buy me a coffee dot com slash fexingo. Now, back to the tension Luna just raised. Luna: Right. So strategic self-correction might save the deal, but at what cost to your own credibility and the team's morale? Lucas: It's a real cost. And I think the key is to use it sparingly — only for high-stakes situations where the outcome matters more than the principle. For smaller disagreements, sometimes it's better to let the boss be wrong and let the consequences teach the lesson. Luna: But what if the consequences never land on the boss? If the VP loses a deal, they might blame the team, not themselves. Lucas: That's a real risk. And that's where documentation becomes your friend. Not in a gotcha way, but in a 'let's learn from this' way. If you can frame a post-mortem around data — 'here's what happened with this deal, here's where the friction points were' — you can let the numbers speak without pointing fingers. Luna: But the never-wrong boss is also good at spinning data. They'll say 'the client was unreasonable' or 'the timing was off.' Lucas: They will. So you need to be strategic about when you escalate. If you have a peer who also reports to this boss, you can build a coalition. If three people independently observe the same pattern, it's harder for the boss to dismiss it as one person's attitude. Luna: That's risky too. If the boss finds out you're talking to colleagues, that can backfire. Lucas: Absolutely. So you have to be careful. This isn't about organizing a mutiny — it's about building a culture of psychological safety among peers so you can check each other's reality. 'Hey, did you hear the VP say that? Did that seem off to you?' That's not insubordination, that's sense-making. Luna: Okay, so we have short-term tactics: strategic self-correction for high stakes, letting small things go, documentation, peer reality checks. But what about the longer term? Can a never-wrong boss change? Lucas: I think they can, but only if they want to. And usually that requires a shock to the system — like a major failure that can't be spun, or feedback from someone above them. If the boss's own manager is a never-wrong type, then the whole organization might be toxic and you're better off leaving. Luna: That's the hard truth. Sometimes the best career move is to recognize that you can't fix the boss, and you need to find a healthier environment. Lucas: Yeah. And I think the sign that it's time to go is when the cost of managing up starts outweighing the value of the work itself. If you're spending more energy on protecting the boss's ego than on doing your actual job, that's not sustainable. Luna: So the question becomes: are you managing up, or are you propping up someone who shouldn't be leading? Lucas: That's the question. And I'd say if you've been using strategic self-correction for more than six months with no change, you're probably propping up. At that point, start planning your exit. Luna: But before you leave, is there any last-ditch effort? Like a direct conversation where you say, 'I notice you have a hard time admitting when you're wrong'? Lucas: I would not recommend that unless you have an incredibly strong relationship and a lot of trust. Most never-wrong bosses will interpret that as a declaration of war. A better approach is to ask for feedback on your own work and then model the behavior you want to see. 'Hey, I realized I made a mistake on X. Here's what I learned.' Sometimes that can create a small opening. Luna: Modeling vulnerability. That's a good point. It might not work, but it at least gives the boss a chance to reciprocate without feeling cornered. Lucas: Exactly. And if they don't, you have your answer. You can leave knowing you tried. Luna: So to wrap up: the never-wrong boss is one of the hardest types to manage because they treat every correction as a threat. Your toolkit is strategic self-correction, documentation, peer reality checks, and modeling vulnerability. And if none of that moves the needle, it might be time to move on. Lucas: And remember that four-hundred-thousand-dollar deal? The account executive who lived through that story actually left the company two months later. The VP is still there, still never wrong. But the AE is now at a company where their voice matters. Sometimes that's the win. Luna: Worth remembering. Thanks, Lucas.