Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Manage a Boss Who Fails Upward
Transcript
- Lucas: There's a special kind of frustration that comes when your boss is objectively bad at their job — and keeps getting promoted anyway. Luna: Oh, the 'failed upward' phenomenon. It's one of the most demoralising things in corporate life. Lucas: Exactly. And it's not just perception — there's data on this. A 2023 study from the University of British Columbia found that incompetent managers are actually more likely to be promoted than competent ones in certain environments. The key variable was something called 'overconfidence signaling'. Luna: So the worse they are, the more confidently they project, and senior leaders mistake that for ability. Lucas: Right. The study specifically showed that managers who performed poorly in their current role were perceived as more leader-like if they displayed high confidence — meaning they got endorsements for promotion despite evidence they couldn't do the job. Luna: That tracks with something I saw at a previous company. A director in our regional office missed every quarterly target for two years straight — and then got moved to a global role with a bigger team. Lucas: Classic case. And the people underneath that director? They had to figure out how to do their jobs while absorbing the fallout. So today, I want to talk about what you actually do when you're reporting to someone who failed upward. Not how to fix them — because you probably can't — but how to protect your own career trajectory. Luna: That's the practical question. Because the natural instinct is to either try to expose the incompetence or just check out. And both can hurt you. Lucas: Let's start with why this happens structurally. The Peter Principle is the old idea that people rise to their level of incompetence. But the newer research suggests something more insidious: organisations actually have incentives to promote bad managers upward. Because if you're performing poorly at your current level, moving you up gets you out of the way of the team that's struggling under you. Luna: It's like musical chairs with promotions. And the people left standing are the ones who have to deal with the next failed-upward boss. Lucas: Exactly. So first strategy: decouple your reputation from your boss's performance. If your boss is constantly messing up, the natural worry is that you'll be tarred by association. But you can build a separate track record — especially by building relationships with stakeholders two levels above you. Luna: You mean skip-level meetings, that kind of thing? Lucas: Yes. If you can establish a direct line — even just a quarterly fifteen-minute check-in — with your boss's boss, you create a channel where your work is visible independent of your boss's failures. The key is to frame it as professional development, not as going over their head. Something like, 'I want to understand how my work aligns with broader department goals.' Luna: That's smart. And it also gives you a sense of whether the people above your boss actually see the incompetence, or if they're completely blind. Lucas: Right. Because sometimes they do see it — they just don't care. They're using your boss as a buffer. And in that case, your strategy has to shift. Luna: What's the second move? Lucas: Document, but don't weaponise. A lot of people under a failed-upward boss start keeping a file of every mistake, every missed deadline, every contradictory instruction. That's useful for your own clarity — but if you use it to try to get your boss fired, you risk looking like the problem. Luna: Especially if leadership has already decided to keep promoting them. You become the person who 'couldn't work with' a manager that everyone else seems fine with. Lucas: Exactly. So document for your own protection. If your boss blames you for something that was their error, you have evidence. But the goal is to use that information defensively, not offensively. If you're ever pulled into an HR conversation, you have receipts — but you're not the one initiating the conversation. Luna: That's a hard discipline. Because the urge to expose them is strong. Lucas: It is. But the data shows that whistleblowers within a company — especially about a superior's incompetence — rarely come out ahead. A study by the Ethics Resource Center found that over sixty percent of internal whistleblowers experienced retaliation, even when their claims were validated. Luna: So the third strategy is probably the hardest: knowing when to leave. Lucas: Yes. And I think the threshold is: has your boss's failure started to materially damage your own career prospects? If you've been passed over for a promotion you deserved, if your projects keep getting killed because of your boss's poor decisions, if your professional reputation outside the company is starting to take a hit — then it's time to go. Luna: There's a cost to staying too long under a failed-upward boss. You start to absorb some of the failure culture, even if you're doing good work. Lucas: Let's take a real example. A friend of mine — let's call him Mark — worked at a mid-sized logistics firm. His boss, a VP of operations, had been promoted three times in four years despite missing every key performance indicator. Mark realised that staying would mean his own career stalled. So he spent six months quietly networking internally and externally, and when he found a lateral move to a different division, he took it. Two years later, that boss was eventually let go — but Mark had already built a new track record elsewhere in the company. Luna: He got out without burning a bridge. That's the ideal. But the internal move isn't always possible. Lucas: If it's not, then external. And I think one of the most underused tactics is to frame your exit around growth — not around your boss's failure. 'I'm looking for a role with more strategic scope' or 'I want to work in a different industry vertical.' You don't mention the incompetent boss. That way, your reference from the company — even from that boss — won't be poisoned. Luna: That's the long game. And it takes patience. But I think a lot of people under a failed-upward boss feel like they have to act immediately, or they get consumed by the frustration. Lucas: If today's conversation resonated with you — if you've been nodding along because you're dealing with this right now — I want to mention something. The reason we can do deep dives like this without ads, without sponsors, without any of that noise, is because of listener support. People who find value in what we do and want to keep it accessible for everyone. If that's you, you can toss a few dollars in the virtual jar at buy me a coffee dot com slash fexingo. That's buy me a coffee dot com slash fexingo. No pressure at all — just a way to keep these conversations going. Luna: And honestly, even a small contribution helps us keep the lights on and the content independent. We really appreciate it. Lucas: Okay, back to the failed-upward boss. One more tactic I want to cover: the 'strategic alignment' approach. Luna: What does that look like in practice? Lucas: You basically accept that your boss is going to keep getting promoted — at least for now — and you position yourself as the person who makes them look less bad. I know that sounds like you're enabling them, but hear me out. Luna: I'm listening. Lucas: If you're the one who quietly corrects the error before it reaches the boss's boss, or who translates your boss's vague directives into actual deliverables, you become indispensable. And indispensable people have leverage. You can ask for things — a title bump, a budget for a project you want to run, a flexible schedule. Your boss will say yes because they need you. Luna: So you're essentially managing up in a way that serves your own interests, not just covering for them. Lucas: Exactly. There's a great HBR piece from 2021 that called this 'managing the incompetence overhead.' You're not carrying their entire load — you're just making sure their worst failures don't become visible. In return, you get a quiet currency that you can spend on your own growth. Luna: But there's a risk there, too. If they get promoted again, you might be stuck doing the same work for a new boss who's just as bad. Lucas: That's real. So you need a time limit. Give yourself six to nine months of this approach, and then reassess. If you've gotten what you need — a promotion, a transfer, a skill that makes you more marketable — great. If not, it's time to execute the exit plan. Luna: I think one thing that often goes unmentioned is the emotional toll. Working under someone who fails upward is deeply unfair. It can make you cynical. Lucas: It is unfair. And I don't want to sugarcoat it. The research on 'perceived injustice' in the workplace shows that it's one of the strongest predictors of burnout and disengagement. So you also need a personal coping strategy — something outside work that reminds you of your own competence. A side project, a professional community, even just a trusted mentor who validates what you're seeing. Luna: Because otherwise, you start to doubt yourself. 'Maybe my boss actually is good and I'm the problem.' Lucas: And that's exactly what the system wants you to think. The failed-upward boss often relies on gaslighting — 'I got promoted, so I must be doing something right, and you're just not seeing the big picture.' Luna: So having an external reference point is crucial. Someone who can say, 'No, the numbers didn't improve, and that's not your fault.' Lucas: Exactly. And that external reference can also help you with the final step: knowing when to stop managing up and start managing out. Luna: Managing out — meaning leaving the company entirely? Lucas: Yes. Or at least leaving that reporting line. And the sign is when your boss's failure becomes so visible that it threatens to take you down with it. If your boss is about to be fired, and you're closely associated, your internal reputation might not survive the transition. Better to be gone before the axe falls. Luna: So you want to leave while you still have a good story to tell. Lucas: Exactly. You don't want to be the person who was on the sinking ship. You want to be the person who saw the iceberg and took a lifeboat to a better vessel. Luna: I think that's the core message: you can't control whether your boss fails upward. But you can control your response. And the worst response is to stay silent and suffer. Lucas: The failed-upward boss is a feature of many organisations, not a bug. The question is whether you let it define your career or whether you navigate around it. And I hope today's episode gave you a few concrete ways to do the latter. Luna: Same here. And if you've got a story about a failed-upward boss you've dealt with, we'd love to hear it. You can reach us through the show's website. Lucas: That's a wrap for this episode. We'll be back on Thursday with another difficult boss deep dive.