Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Handle a Boss Who Gives Conflicting Directions
Transcript
- Lucas: So you get into the office — or you open Slack — and your boss has given you what sounds like a clear directive. You spend three hours on it. Then at the stand-up, they say, 'No, actually, I need you to pivot.' And you're sitting there thinking — wait, what happened to the thing you just told me? Luna: That's the classic conflicting-directions trap. And it's surprisingly common. A 2025 workplace survey found that 47 percent of employees say conflicting direction is their number one source of work stress — ahead of workload and deadlines. Lucas: Forty-seven percent. That's huge. And I think the reason it's so stressful is that it's not just about the work itself — it's the feeling that you can't win. Whatever you do, there's a version of your boss who's going to say you did the wrong thing. Luna: Right. It's like Schrödinger's assignment. You're simultaneously doing the right thing and the wrong thing until your boss opens their mouth. Lucas: Exactly. So today I want to drill into a specific case — a product manager I'll call Jenna. She worked at a mid-size B2B software company, about 400 employees. Her VP told her, 'Move fast, ship the MVP by Q2.' Her director said, 'Quality is non-negotiable — we cannot ship until all edge cases are covered.' Two bosses, two conflicting mandates. Luna: And Jenna is stuck in the middle, trying to please both. That's a recipe for burnout. Lucas: Yeah. And what she did — or what she eventually did — is a really good framework for anyone in that position. First step: document the contradiction explicitly. Not in a gotcha way, but as a neutral summary. She wrote an email to both bosses that said, 'I want to make sure I'm aligned. I understand the goal is to ship by end of Q2, and I also understand the quality bar is zero known edge-case bugs. Can you help me understand how to prioritize when those two conflict?' Luna: That's a smart move. It forces them to acknowledge the contradiction in writing. And it shifts the burden back to them to resolve it. Lucas: Exactly. And in Jenna's case, the VP and director actually had a conversation and came back with a compromise: ship on time, but with a documented list of known edge cases that would be patched in the following sprint. So the contradiction got resolved. Luna: But what if they don't resolve it? What if the bosses just say, 'Figure it out'? Lucas: Then you go to step two: escalate to a single decision-maker. That might mean asking, 'Who owns the final call on this?' If you have two bosses, you need to identify which one has the ultimate authority on the specific decision. Sometimes it's the higher-ranking person. Sometimes it's the one whose budget it is. You need to find that out. Luna: And if they both claim authority? That's a whole other problem. Lucas: That is a problem. But then you're into organizational dysfunction that's above your pay grade. At that point, you might need to have a conversation with HR or with your skip-level — but carefully, because you don't want to be seen as insubordinate. Luna: Let me ask you this — you mentioned a third step earlier. What's that? Lucas: Step three is creating a decision-tree for yourself. This is something you can do even before the contradiction arises. For any given project, map out: if this happens, do A; if that happens, do B. It's essentially a personal playbook for ambiguity. So when your boss says 'pivot,' you already have a framework for deciding which direction to go. Luna: I love that. It's proactive. And it also signals to your boss that you're thinking strategically. Lucas: Right. And listeners — you know, we talk a lot on this show about practical tactics for dealing with difficult bosses. And it's something we're able to keep doing because a small group of listeners chips in monthly through buy me a coffee dot com slash fexingo. That's what keeps the show ad-free and focused on real, actionable advice. Luna: Yeah, it's a big help. And it means we never have to run ads or sell your data. So if this show has helped you navigate a tough boss situation, it's a nice way to give back. Lucas: Okay — back to the framework. One thing I want to emphasize about documentation: it's not about building a case against your boss. It's about building clarity for yourself. When you write it down, you often realize the contradiction isn't as stark as you thought. Or you see exactly where the tension lies. Luna: That's a good point. I've definitely had moments where I was frustrated, and then I wrote an email and thought, 'Oh, actually, I can see why they said both things.' Lucas: Yeah. And sometimes the fix is as simple as asking for a priority ranking. Like, 'On a scale of one to ten, how important is speed versus quality on this specific deliverable?' That forces your boss to make a trade-off explicit. Luna: And if your boss says 'both are a ten'? Lucas: Then you have a different problem — a boss who can't or won't prioritize. In that case, you might need to set a boundary. Say, 'I can deliver one hundred percent on one of these, or sixty percent on both. Which would you prefer?' It's a gentle way of forcing accountability. Luna: That's a great line. I'm going to use that. Lucas: Please do. And one more thing — if the conflicting directions are chronic, not just occasional, that's a red flag. It might indicate that your boss is disorganized, or that they're getting pressure from above and passing it down without filtering it. In that case, you might need to think about whether this is a sustainable situation. Luna: So the framework is: document, escalate to a single decision-maker, and create a decision-tree. And if that doesn't work, consider whether the environment is fundamentally broken. Lucas: Exactly. I think the key takeaway is that conflicting directions are often a failure of leadership, not a failure of your execution. And the best thing you can do is shine a light on the contradiction in a constructive way — not to complain, but to get alignment. Luna: And if you get alignment, great. If not, at least you have clarity on what's broken — and that's valuable information for your own career decisions. Lucas: Yeah. It's a tough spot to be in, but you're not powerless. Small steps make a big difference.