Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / Managing a Boss Who Never Gives You Straight Answers
Transcript
- Lucas: So, Luna, real talk. You're in a one-on-one with your boss, you ask a simple question: 'Should I move forward with the vendor contract or not?' And the answer you get is... 'Let's keep that on the radar.' Luna: Oh, the classic non-answer. I've been there. It's like they're speaking in code that only they understand. Lucas: Right. And it's not just frustrating, it's genuinely costly. When your boss is vague, you end up guessing, stalling, or redoing work. In fact, a recent survey from the Project Management Institute found that poor communication is a factor in about a third of failed projects. That's not a small number. Luna: A third. So this isn't just a 'oh, my boss is annoying' problem. It's a 'my project might literally fail' problem. Lucas: Exactly. And today we're going to dig into one specific flavor of this: the boss who never gives you a straight answer. Not the boss who's just busy, not the one who's micromanaging, but the one who, no matter what you ask, seems to have a PhD in evasion. Luna: So what's the first thing we need to understand about these bosses? Like, what's really going on under the hood? Lucas: I think the first thing is to separate intention from effect. Some bosses are vague because they genuinely don't have the information yet. Others are vague because they're avoiding a decision. And a small but important group are vague on purpose, because being clear would expose them or commit them to something they don't want to own. Luna: So you're saying it's not always a character flaw. Sometimes it's just a lack of data. Lucas: Right. And that's actually a critical distinction, because your strategy for dealing with it changes completely. If your boss just doesn't know, you can help them get the answer. If they're dodging, you have to change the incentive structure. And if they're strategically vague, you need to protect yourself. Luna: Let's talk about that first group, the 'doesn't know' boss. How do you even tell the difference? Lucas: So one tell: they'll say things like 'I need to check with finance' or 'Let me get back to you on that' and then actually follow up. That's a good sign. But if they say 'let's circle back' and then never do, that's a signal they're avoiding something. I have a concrete example from a product manager I know. Luna: I'm all ears. Lucas: Her name's Sarah, and her boss kept telling her 'let's hold off on the vendor decision' for six weeks. She'd ask in every one-on-one, and he'd say 'it's on my list' or 'we need to align with the broader strategy.' Finally, she sent him a short email: 'I want to make sure I'm not blocking anything. What specifically is holding us back? Is it budget, timeline, or something else?' And he replied with a one-line answer: 'It's budget, I'm hoping to get more funding next quarter.' That was it. Luna: Whoa. So just asking a more specific question unlocked the actual reason. Lucas: Exactly. She was asking a yes or no question, and he was avoiding the yes. But when she asked 'what's the constraint?' he could answer without committing to a date. That's a great example of rephrasing your question to make it easier for the boss to be honest. Luna: So the lesson is: don't ask 'when can we start?' ask 'what's in the way?' That kind of reframe is really powerful. Lucas: And that's also where I think we should pause for a second. If today's episode helps you in a real meeting tomorrow, that's worth a coffee to me. And honestly, that's the link: buy me a coffee dot com slash fexingo. It's a small way to keep this show ad-free, and it's genuinely appreciated. Luna: Yeah, I've seen that link. It's a low-key way to support the show, and every little bit helps us keep doing deep dives like this. Lucas: So back to the second group: the boss who's dodging a decision. They have the authority, but they don't want to use it. What do you do there? Luna: That sounds like a boss who's afraid of making a wrong call, or maybe they're not the real decision-maker themselves. Lucas: Often it's a boss who's worried about accountability. If they say 'go ahead' and it fails, they're on the hook. So they keep the door open. In that case, you need to make it easier for them to say yes by reducing the perceived risk. You can say something like, 'I'll take the lead on this, and if it goes sideways, I'll own it. I just need your approval to move forward.' Luna: That shifts the risk onto you, which might be exactly what they need to hear. But is that always safe? You're putting your neck on the line. Lucas: It's a calculated move. If you're confident in the project and you have a track record, it can work. But you're right to be cautious. That's why you also want to document that you offered to own it. Send a follow-up email after the conversation: 'As discussed, I'm happy to lead this and assume responsibility. Let me know if you'd like any modifications.' That way, if they say nothing, you have a record that you proposed a clear path. Luna: So documenting is key. But what about the third group, the strategically vague boss? That sounds more manipulative. Lucas: Yeah, and this is the one that can really burn you. This is the boss who gives you just enough information to start working, but never commits to a specific outcome. They might say 'I'm thinking we should explore a few options' and then never define what 'a few' means. Or they give you conflicting instructions depending on who's in the room. Luna: That sounds like a boss who wants to keep their options open, or maybe they're playing politics with their own boss. Lucas: Exactly. And in that case, your best move is to create a written record of every ambiguous instruction and your interpretation of it. I call it the 'Precision Email.' After any conversation that leaves you unclear, send a summary like: 'Just to confirm, my understanding is that I should proceed with Option A and deliver by the 30th. If that's not correct, please let me know by Friday.' Luna: And if they don't respond? Lucas: Then their silence is your answer. You've given them a chance to correct you, and they didn't. That's not a guarantee, but it's your best defense if they later say 'that's not what I meant.' You have a paper trail. Luna: I love that. It's proactive, but not aggressive. You're giving them a chance to clarify in writing. Lucas: Right. And there's one more tactic that works across all three types: the time-bound question. Instead of 'can you get me an answer?' say 'I need a decision by Wednesday to keep the project on track. If you can't decide by then, I'll proceed with the default option.' That forces a choice. Luna: That's a little confrontational though. What if your boss gets annoyed? Lucas: You have to gauge your relationship. But in most cases, bosses respond to clear consequences. And if they get annoyed, that's a signal they're not willing to engage with the process. That might be your cue to escalate to a skip-level or to HR if it's really affecting your work. Luna: When would you actually go over their head? That's risky. Lucas: It's a last resort, but if you've tried the precision email, the time-bound question, and you still can't get a straight answer, and the project is failing because of it, then you have a legitimate case. You frame it as 'I wanted to flag a communication bottleneck that's impacting delivery.' Not 'my boss is terrible.' And you bring evidence: the emails, the deadlines missed, the decisions stuck in limbo. Luna: That's smart. You're not just venting; you're documenting a systemic issue. But what about the smaller everyday vague comments, like 'make it pop' or 'let's be more strategic'? Those drive me nuts. Lucas: Oh, those are the worst. My rule of thumb there is to ask for parameters. If your boss says 'make it pop,' you ask, 'Compared to what? Do you want it brighter, more minimal, or more playful?' You turn a subjective comment into a concrete set of choices. Luna: So you're essentially teaching your boss how to give you better instructions. Lucas: Exactly. And after a few times, they might start being more specific on their own. It's like training a muscle. But you have to be consistent and patient. Luna: So let me try to distill what we've talked about. One: figure out if your boss is clueless, cautious, or calculated. Two: adjust your approach accordingly. Three: always document your understanding in writing. Four: use time-bound questions to force a decision. And five: only escalate if you've exhausted those options. Lucas: That's a perfect summary. And I think there's one more thing to keep in mind: a vague boss might not change overnight. You're not going to fix them in a week. But you can change the dynamic one conversation at a time. And that's the real goal of managing up. Luna: I think that's a great note to end on. If you're nodding along, you've probably dealt with this. And if you've got your own story about a boss who never gives a straight answer, we'd love to hear it. Maybe we'll feature it in a future episode. Lucas: Yeah, send it to us. But for now, thanks for listening, and we'll catch you next time.