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 you have a boss who is never wrong. Every suggestion, every correction, every piece of data that contradicts their position — it's met with a wall. Maybe they say 'you're not seeing the big picture' or they just stare at you until you back down. Luna: Oh, I've had that. It's exhausting. You stop bringing things up because you know it's going nowhere. Lucas: Right. And that's the real cost — not just the bad decisions that stand, but the good ideas that never get a hearing. A 2019 study from Harvard Business School looked at overconfidence in executives and found that managers who score high on overconfidence metrics are significantly more likely to reject contradictory information, even when it's clearly correct. One of the co-authors, Don Moore, told me the key driver is what they call 'social image preservation' — the fear that admitting a mistake will permanently damage their authority. Luna: So it's not really about the data for them. It's about status. That makes it harder to argue against, because you can't logic someone out of a position they didn't logic themselves into. Lucas: Exactly. And I want to dig into a concrete case today because the theoretical stuff only gets you so far. Back in 2022 I spoke with a supply chain analyst at a mid-sized logistics firm — let's call it 'National Freight Partners' — who was dealing with a COO who had championed a routing algorithm that was... not great. The algorithm was increasing fuel costs by about 18 percent versus the industry benchmark. The analyst built a spreadsheet showing $200,000 in extra costs per month. Luna: That's $2.4 million a year. I can't imagine they ignored that. Lucas: They did. The COO said the analyst was 'cherry-picking routes' and dismissed the whole thing. So the analyst tried a different approach. Instead of presenting the data as a challenge, he framed it as 'I'm trying to understand how the algorithm achieves cost savings, can you walk me through it?' That lowered the defensiveness just enough to get the COO to look at the data together. But that still took three more months and a consultant's report — which the COO accepted because it came from an outside expert. Luna: Classic. The same data, but coming from a third party suddenly becomes credible. That's a tactic I've used — bringing in an industry benchmark or a published study rather than your own analysis. Lucas: It works because it bypasses the personal threat. And the analyst eventually got the algorithm changed, but not before the company burned through an extra $1.2 million in fuel costs over six months. That's the real-world cost of a 'never wrong' boss. So let's talk about the playbook for dealing with this — what works, what doesn't, and when you should consider leaving. Luna: Start with what doesn't work. Confrontation in a meeting, especially public correction, is probably at the top of the list. Lucas: Yeah, that's the nuclear option and it almost never ends well. The boss doubles down because backing down in front of others is the worst-case scenario for their image. So rule one: never correct them in a group setting. Save it for a one-on-one, and even then, frame it as curiosity. Say 'help me understand your thinking here' rather than 'I think you're wrong.' The goal is to make the correction feel like their idea. Luna: That's the classic 'managing up' move. But what about when the boss is so entrenched that even the gentle approach fails? The National Freight example took six months. Lucas: Then you escalate. But escalate strategically. The next step is to use a third-party authority — an industry report, a consultant, a benchmark from a trade group. If your boss respects certain sources, bring that source into the conversation. 'I was reading the latest Gartner supply chain survey and it says the average fuel efficiency for our fleet type is X. We're at Y. Do you think there's something unique about our operations that explains the gap?' Now you're not making a claim, you're asking a question that the data answers. Luna: That's smart. And if that still doesn't work, you might need to document everything. There's a fine line between persistence and insubordination, and if you ever need to go to HR, you'll want a clear pattern of the boss ignoring reasonable evidence. Lucas: Speaking of documentation — one listener wrote in with a tactic I thought was clever. They kept a running 'decision log' in a shared document that the whole team could see — not as a weapon, but as a neutral record. It listed the proposed action, the data behind it, the boss's decision, and the outcome. Over time, it became hard for the boss to deny that certain patterns were emerging. The log itself was just facts. It forced accountability without direct confrontation. Luna: I like that. It's passive but powerful. And it also protects you if things go south — you have a paper trail showing you flagged the issue. But let's talk about the darker side. What about the boss who is not just overconfident but actively retaliatory? Lucas: That changes the calculus entirely. If you suspect retaliation, you need to protect yourself first. Don't be the lone voice of dissent. Find allies — other people who see the same problem. A group raising an issue is much harder to dismiss or punish than an individual. And if you can get your concerns in writing through proper channels — like a formal risk assessment or an ethics hotline — that creates institutional recognition. Luna: At some point though, you have to ask yourself: is this worth it? If the boss is never wrong and the culture backs them up, you might be fighting a losing battle. Lucas: That's the hardest question. I think you need to set a threshold: 'How much bad decision-making can I tolerate before it affects my career or my sanity?' For some people, the answer is zero and they start looking. For others, it's about learning to work around the boss while protecting their own reputation. But if you're constantly being blamed for the boss's mistakes, that's a red flag that no amount of managing up can fix. Luna: And that's where the 'malicious compliance' trap comes in. Some people think 'I'll just do exactly what the boss says, even if it's wrong, and let them fail.' But that rarely works out well for the employee. You end up looking like you went along with a bad plan. Lucas: Malicious compliance is a revenge fantasy, not a strategy. In practice, it damages your credibility and your relationships. The better approach is to state your objection once, clearly, in writing, and then follow the boss's direction while noting the risks. That way you've discharged your responsibility without insubordination. If the decision fails, you have the record, and you didn't sabotage anything. Luna: I want to circle back to something you said about framing. You mentioned using curiosity as a tool. Can you give a specific script? Lucas: Sure. Let's say your boss insists on a marketing budget allocation that you think is too heavy on print ads. Instead of saying 'Print is dead, we should put that money into digital,' you say: 'I'm trying to understand how print fits into our overall strategy. In the past, our digital campaigns have had a 3x higher conversion rate. Is there something about this campaign that makes print more effective here?' You're not saying they're wrong. You're asking for the logic. If they have a good answer, you learn something. If they don't, you've planted a seed. Luna: And if they get defensive anyway? Lucas: Then you know you're dealing with someone who is not open to evidence at all. That's valuable information. You can then decide whether to work around them — by going to their boss, or by building a coalition — or to leave. But don't keep banging your head against the wall. The cost-benefit changes once you've confirmed the boss is unreachable. Luna: I think that's a really important takeaway. Not every boss can be managed. Sometimes the best management move is to exit. Lucas: Listen, if this episode has helped you think through a career decision or given you a tactic to try, we want to say something. This show has always been ad-free, and that's possible because of listeners who choose to support us. If you've gotten value from it, you can head to buy me a coffee dot com slash fexingo. It's a simple way to keep the lights on and keep these episodes free for everyone. Luna: Yeah, it really does make a difference. Even a small contribution adds up. And we appreciate every single person who has taken the time to do that. Lucas: Back to the tactics. Another powerful one is what I call 'the pre-mortem.' Before a major decision, ask the team to imagine it's six months later and the decision has failed. What went wrong? This technique, popularized by psychologist Gary Klein, forces people to articulate risks without feeling like they're criticizing the boss's plan. It's a way to surface objections in a hypothetical, low-threat frame. Luna: I've used that! It works especially well when the boss is the one leading the decision, because they feel like they're being proactive rather than defensive. You say 'Let's stress-test this decision by imagining worst-case scenarios.' And suddenly everyone can speak freely. Lucas: Right. And the best part is, the boss often ends up adopting the suggestions because they came out of their own 'what-if' exercise. They own the fix. That's the ideal outcome — the boss improves the decision and feels good about it. Luna: Let's talk about the emotional toll. Dealing with a never-wrong boss is draining. You start second-guessing yourself. You wonder if maybe you are the problem. Lucas: That's a real risk. And it's why you need external validation — mentors, peers, professional networks. If everyone else in your life tells you you're reasonable, but your boss makes you feel crazy, the problem is probably your boss, not you. I'd recommend keeping a 'reality check' file — just a private document where you note down situations where the boss dismissed valid data. Over time, it'll remind you that your perception is accurate. Luna: And if you can, get a therapist or a career coach. Seriously. That's not a luxury — it's maintenance. Because this kind of environment can erode your confidence long-term. Lucas: To wrap up, I want to leave you with one concrete action. This week, identify one area where you and your boss disagree on facts. Instead of arguing, gather a third-party source — an industry average, a consultant report, a published study — and present it as a question: 'I saw this data and I'm trying to reconcile it with our approach. Can you help me understand?' See what happens. If the boss engages, you've made progress. If they stonewall, you have your answer. Luna: And that answer might be: time to update the resume. Because life's too short to work for someone who can't admit they're wrong. Lucas: That's the bottom line. Thanks for listening, and we'll be back next week with another episode.