Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Manage a Boss Who Undermines You to Senior Leadership
Transcript
- Lucas: We've talked on this show about bosses who take credit, bosses who micromanage, bosses who rewrite your work. But there's a particularly sneaky version that's harder to catch and even harder to fight back against. Luna: The boss who undermines you behind closed doors to people above their pay grade. I've seen that one up close. Lucas: Exactly. In your one-on-one, your boss is all smiles. In the executive meeting you don't attend, they're questioning your judgment, your competence, your readiness for the next level. And you only find out when a senior leader gives you that look — the one that says 'I've heard things.' Luna: That's brutal. And it's hard to defend against because the damage is already done by the time you know about it. Lucas: Let's anchor this with a real story. A marketing director at a Fortune 500 company — I'll call her Priya — was running a global rebranding project. Her VP would tell her directly that she was doing a great job. Luna: Typical. And behind the scenes? Lucas: The VP was telling the CMO and the CEO that Priya was 'struggling with stakeholder alignment' and that the rebrand timeline was slipping because of 'poor project management.' Neither of those things was true. Priya was hitting every milestone. Luna: So how did she find out? Usually it's through a well-meaning colleague who was in the room. Lucas: Exactly right. Another VP — a peer of her boss — pulled her aside after a meeting and said, 'Hey, I just want to give you a heads up. In the exec review, your boss said you're a bottleneck. I think that's unfair, but I wanted you to know.' Luna: That's a gift. An honest ally. But most people don't have that. Lucas: True. So the first step is to make sure you do have that ally — or to cultivate one. Priya started having informal coffee chats with two other senior leaders in adjacent functions. Not to complain about her boss, but to share what she was working on. Luna: So she's building her own narrative before the boss can poison the well. Lucas: Right. She wasn't defensive — she was proactive. She'd say, 'Here's the rebrand timeline, here's where we're on track, here's one challenge we solved last month.' Just normal update stuff. But now three people in the C-suite had her version of reality. Luna: And that changes the math. When the boss says something negative, the senior leader has competing data from the source herself. Lucas: Exactly. But what if you don't have access to those senior leaders? That's the second step. Priya started using email as a documentation weapon — not in a passive-aggressive cc everyone way, but she began sending weekly one-paragraph status updates to her boss, with a clear list of accomplishments and next steps. Luna: And she kept a copy. So if her boss claimed a project was slipping, she had a record showing it was on time. Lucas: Bingo. And she did it in a way that looked helpful, not suspicious. 'Just wanted to make sure you have everything for the exec meeting.' After a few weeks, her boss couldn't claim she was behind without contradicting the written record. Luna: That's smart. But what about the more personal stuff — like when the boss questions your judgment or your interpersonal skills? That's harder to document. Lucas: Much harder. That's where the third step comes in: you have to force the issue into a formal setting. If you suspect your boss is questioning your competence, request a 360-degree feedback process or a skip-level meeting. Luna: A skip-level with your boss's boss. That can backfire if your boss sees it as going around them. Lucas: It can. So you frame it as development. 'I'm working on my executive presence and I'd love feedback from senior leaders on how to grow.' That's hard for a boss to block without looking insecure. And in that meeting, you can subtly demonstrate your competence without ever mentioning your boss. Luna: So you're letting your work speak for itself in a room where your boss isn't present. Lucas: Exactly. And if the senior leader brings up something your boss said, you handle it with curiosity, not defensiveness. 'That's interesting — I wasn't aware of that concern. Can you tell me more about what you heard?' That buys you information without looking like you're attacking your boss. Luna: You're basically using the same technique a PR person would use to manage a reputation crisis. Lucas: It's exactly reputation management. You're not trying to change your boss — you can't control them. You're trying to control the information environment around you. Luna: And if that doesn't work? If the boss keeps undermining you and your reputation keeps taking hits? Lucas: Then you have to ask whether this is a pattern of constructive dismissal. In many jurisdictions, if your boss's actions make it impossible for you to do your job or damage your professional standing enough that you feel forced to resign, that can be a legal claim. Luna: But that's a nuclear option. And it requires documentation. Lucas: Massive documentation. Dates, times, what was said, who was present, how it affected your work. And ideally, you've already tried to address it through HR or a formal complaint. But look — if you're at the point where you're documenting for a potential legal case, the relationship is probably beyond repair. Luna: And that's a hard truth. Sometimes the only winning move is to leave. Lucas: Before you leave, though, you want to have your reputation intact. That means you should have already been building those relationships with senior leaders, getting your wins on the record, and making sure your next employer hears your version, not your boss's. Luna: You know, a lot of this comes down to that uncomfortable task of promoting yourself without looking like you're self-promoting. And that's a skill most of us aren't taught. Lucas: It's a skill that separates people who get stuck from people who move up. And on that note — speaking of skills that make a real difference in a career — this is a good moment to mention something. Luna: What's that? Lucas: If this podcast has helped you navigate a tricky workplace situation, or you've used one of our strategies to protect your reputation, and you'd like to see us keep making episodes ad-free, the simplest way to support us is at buy me a coffee dot com slash fexingo. No pressure at all — just a way for listeners who find value here to chip in. Luna: Yeah, I think a lot of people don't realize how much work goes into researching these concrete examples. For every episode, Lucas and I dig through real cases, talk to HR professionals, employment lawyers. That listener support keeps it all running. Lucas: Exactly. And it keeps the show free for everyone. So, back to the question of when to stay and when to go. Let me give you a framework for that decision. Luna: Good. Because that's the million-dollar question. Lucas: I call it the three strikes rule for reputation damage. Strike one: you hear from a reliable source that your boss undermined you once. That's a warning. You start the proactive relationship building and documentation. Luna: Strike two? Lucas: You hear it again, or you see concrete evidence — a project you led gets reassigned, a promotion you were in line for goes to someone else, a senior leader starts treating you differently. At that point, you escalate. You request that skip-level meeting, you document everything, and you start a quiet job search. Luna: And strike three is when the damage becomes public or permanent. Lucas: Right. You're passed over for a role, your performance review includes criticism that you know came from your boss's misrepresentation, or you're put on a performance improvement plan based on false claims. At that point, the system is working against you, and you need to leave. Luna: And leave with your documentation intact, your references arranged, and your story straight. Lucas: Exactly. The worst outcome is leaving in a cloud of suspicion, where your boss's narrative follows you. That's why you start building your counter-narrative early, before you even know you need it. Luna: One thing I'd add: if you're in a position where you have a good relationship with someone in HR, it's worth having an off-the-record conversation about the dynamic. HR's job is to protect the company, but if your boss is creating legal exposure through constructive dismissal, they might intervene. Lucas: That's a good point. HR is not your friend, but they are risk-averse. If you can frame the issue as a risk to the company — 'My boss's behavior is creating a hostile environment that could lead to a lawsuit' — they might act. But tread carefully. Luna: So let's leave listeners with a concrete checklist. Three things to do this week if you suspect your boss is undermining you. Lucas: Number one: start a running document of your accomplishments and positive feedback. Date it. Store it outside your work email. Number two: schedule an informal coffee or virtual chat with one senior leader you don't report to, and share something you're proud of. Luna: And number three: pay attention to those little signals. A change in how senior leaders look at you, a shift in meeting invitations, a project that goes to someone else. Don't ignore them. Lucas: Most people wait until the damage is done. The people who survive and thrive in difficult boss situations are the ones who act before they know for sure. That's the difference.