Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Handle a Boss Who Holds Grudges
Transcript
- Lucas: You have a disagreement with your boss — maybe you pushed back on a deadline, questioned a decision, or pointed out a flaw in their logic. A few days later, the issue seems resolved. But weeks pass and every conversation carries a chill. They bring up your past mistake in unrelated meetings. They assign you less visible work, exclude you from key emails, and you're pretty sure you're still in the doghouse. Luna: That lingering tension — where you can't quite get back to neutral — is what we're talking about today. The boss who holds a grudge. Lucas: Right. And it's different from a boss who's simply disappointed or setting a boundary. A grudge is personal. It's emotional. And it's surprisingly common in workplaces where power dynamics make it hard for both sides to truly clear the air. Luna: I've definitely felt that. You think the conversation is over, but the boss acts like it's still happening. So what's going on psychologically? Lucas: Organizational psychologist Ben Dattner has written about this. He calls it 'status threat.' When a subordinate questions a boss, it can feel like a challenge to their authority — especially if the boss is insecure. The grudge becomes a way to reassert dominance, to punish the person who made them feel vulnerable. Luna: So it's not really about the original issue. It's about ego and control. Lucas: Exactly. And that's important because it reframes how you respond. If you treat it as a factual dispute that just needs more explanation, you'll keep banging your head against the wall. The real work is emotional repair. Luna: Let's get concrete. Do you have a case study? Lucas: I do. A marketing manager I'll call Jenna — mid-size agency, about 200 employees. She's on a team of six reporting to a creative director named Paul. Paul is known as a brilliant strategist but thin-skinned. Jenna openly disagreed with him in a team meeting about the timeline for a major campaign launch, citing data from a similar project that had failed under a tight schedule. Paul conceded the point in the moment, but from that day forward, he stopped looping her into strategy discussions, reassigned her lead role on the campaign to a junior, and started making passive-aggressive comments in reviews about her 'lack of team alignment.' Luna: That's textbook grudge behavior. And six months later, she was still dealing with it? Lucas: Six months. Jenna tried everything — over-delivering on her work, apologizing again, avoiding conflict. Nothing changed. Paul would say 'water under the bridge' but his actions said otherwise. Luna: So what actually works in a situation like that? Because 'just do good work' clearly isn't enough. Lucas: The research — and coaches I've spoken to — point to a few strategies. The first is to distinguish between a grudge and a pattern of retaliation. If the behavior includes demotion, exclusion from opportunities, or negative performance reviews that don't match your actual contributions, it may cross into retaliation. That's a legal risk and you should document everything. Luna: Right. But if it's more subtle — the cold shoulder, the snide remarks — you probably need to try a reset conversation. Lucas: Yes. And the reset conversation is different from another apology. You're not re-litigating the original issue. You're acknowledging the relational rupture directly. Something like: 'I get the sense that our disagreement a few months ago is still affecting how we work together. I'd like to understand what you need from me to move forward.' Luna: That's hard to say. It requires vulnerability. But it also puts the ball in their court — they have to either admit there's a problem or lie and say everything's fine. Lucas: Right. And if they say everything's fine but the behavior continues, you've learned something important: this is not a grudge you can resolve one-on-one. Then you need to consider your options — transfer, escalate to HR, or leave. Luna: Before we get into those options, I want to pause on something. All this advice — it's only useful if people are actually hearing it. And honestly, having a podcast that digs into these messy dynamics is rare. Most career content is either generic or just 'be positive.' Lucas: Yeah, and that's exactly why listener support matters for shows like this. We keep The Difficult Boss Podcast ad-free because we think these conversations are better without commercial breaks — but that's only possible because of people who chip in. If you've gotten something out of our episodes, you can support us at buy me a coffee dot com slash fexingo. Luna: Even a one-time contribution makes a difference. And we genuinely read every message people leave there — your stories sometimes become future episodes. Lucas: Okay, back to Jenna. She tried the reset conversation. Paul said he appreciated her asking, but nothing changed. So she started documenting — dates, emails, assignments she was excluded from — and built a case. Luna: And then what? HR? Lucas: She did go to HR, but carefully. She framed it not as 'my boss is mean' but as 'I'm concerned about career growth and feel systematically excluded from high-visibility work.' That's hard for HR to dismiss. The head of HR had a conversation with Paul, and within a few weeks, Jenna was back on the campaign — but the trust was still broken. Luna: So ultimately she left? Lucas: Six months later. She got a job at a competitor where her new boss had a reputation for directness but not grudges. And she told me the biggest lesson was: never again wait six months to address the relationship. The earlier you try to reset, the less entrenched the grudge becomes. Luna: That's a good takeaway. But I want to push back a little. Is there ever a risk that the reset conversation backfires — that the boss sees it as manipulation? Lucas: Absolutely. If the boss is highly narcissistic or paranoid, any attempt to address the relationship can be seen as a power play. In that case, you might be better off bypassing the conversation and working around them — building allies, getting sponsorship from a skip-level, or finding a lateral move. Luna: So read the boss's personality first. If they're the type who can handle a direct conversation, try it. If not, protect yourself quietly. Lucas: Exactly. And know that grudges tend to fade faster when you make yourself useful again. Not by groveling, but by solving a problem they care about. If you can help them succeed on something important, the grudge often dissolves because you've re-proven your value. Luna: That's strategic — not about the past, but about creating a new narrative. Lucas: Right. And if none of that works, and you're in a genuinely toxic situation, there's no shame in leaving. Your career is too long to spend it in someone's emotional prison. Luna: So to wrap up: if you're dealing with a boss who holds a grudge, first assess whether it's retaliation or just coldness. Try a reset conversation once. If that fails, document, build support, and consider a move. And above all, don't internalize it — their grudge is about them, not you. Lucas: Well said. And next time, we'll talk about a related dynamic: the boss who pits team members against each other. That's a whole different kind of difficult. Luna: Looking forward to it. Thanks for listening, everyone.