Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Manage a Boss Who Never Gives You Context
Transcript
- Lucas: So Luna, I want to talk about a scenario that I think every single one of us has hit at some point: you get a task from your boss, it's vague, it's missing the why, it's missing the success criteria, and you're left to fill in the gaps on your own. Luna: Oh, absolutely. It's like being handed a map with no 'you are here' marker. You just start walking and hope. Lucas: Exactly. And today we're going to focus on a specific case that came up in a listener question a couple of weeks ago. A product manager at a fintech startup was told to 'improve onboarding' — that was it. No baseline metrics, no target, no stakeholder list. And she had to decide: do I ask for clarity, or do I just run with my own assumptions? Luna: And what did she do? Lucas: Well, she actually emailed me because she was paralyzed. She'd seen too many colleagues go off and build something impressive-sounding that got quietly shelved because it wasn't what the boss actually wanted. So we talked through a framework that I've seen work in a few different industries. Luna: Okay, I'm curious. What's the framework? Lucas: It's four questions. And the first one is the most obvious but the one we skip: 'What problem are we trying to solve?' Not 'What feature should we build?' — problem, first. Her boss might say 'onboarding is confusing' or 'we're bleeding users at step three.' That changes everything. Luna: Right, because 'improve onboarding' could mean reduce drop-off, increase completion, or even just make it less ugly. They're totally different projects. Lucas: Exactly. So question one is about the problem. Question two is about the evidence: 'What data do we have that shows this is a problem?' If your boss can't point to a metric or a user complaint, you're probably dealing with a hunch, and you need to know that going in. Luna: Yeah, and sometimes the boss just doesn't have the data. So then what? Lucas: That's when you move to question three: 'Who else should be involved?' Because context often lives in other people's heads. In this case, the PM asked her boss, 'Can I talk to the data analyst who owns funnel metrics, and the customer support lead who hears the complaints?' And just asking that question signaled that she wasn't going to operate in a vacuum. Luna: Smart. And that also covers the political angle, right? You're pulling in stakeholders so when you do deliver, they're already bought in. Lucas: Exactly. And the fourth question is the one that most of us are scared to ask, because it sounds like we're doubting the boss: 'What does success look like?' Not in vague terms, but 'What would we see in the numbers in three months if this went well?' Luna: Yeah, and that's where you might get a specific target, like 'increase completion rate from 60 to 70 percent.' Now you have a concrete goal. Lucas: Right. And if your boss can't answer any of those four questions — not one — then you have a real problem. But you've also just given yourself a strong position to say, 'I need a bit more direction before I start pulling resources on this.' Luna: And let's be honest, sometimes the boss genuinely doesn't know. They're just throwing something at you because they're overwhelmed. So asking these questions isn't insubordination, it's actually helping them think. Lucas: That's the reframe that I think is crucial. You're not being difficult — you're being a strategic partner. And the PM in that case, she sent a follow-up email after a quick chat with her boss, summarizing the answers to those questions. It took her ten minutes, but it saved her weeks of potential misalignment. Luna: And this is actually a great reminder for all of us: if you're ever in a role where you're giving out tasks, give the context upfront. It's a sign of a good leader, not a weak one. Lucas: Yeah, and that's the kind of thing we get into on this show a lot. And if you've gotten something out of these conversations, even a small amount of support can keep them going. A couple of dollars a month at buy me a coffee dot com slash fexingo genuinely makes a difference for us. Luna: Yeah, it really does. It helps us keep the show ad-free and focused on the real talk. Lucas: Anyway, back to that PM. She sent the email, and her boss came back with a one-liner: 'Just make it less confusing.' That's still not great, but at least she knew the problem was perceived confusion, not a specific metric. So she took a different approach. Luna: What did she do? Lucas: She went straight to the source. She ran a quick usability test with five new users, watched them try to sign up, and found that the real friction was a single form field that was triggering a technical error. The fix was a two-line code change. She presented that to her boss with the video clips, and her boss was thrilled. Luna: Wow, so she turned a vague directive into a specific win just by gathering her own context. Lucas: Exactly. And that's the other side of this coin. Sometimes the context isn't going to come from your boss, so you have to go find it yourself. The four questions are the starting point, but they're not the end. Luna: Before we go further, I want to share a cautionary tale from my own career. I had a colleague who was once told to 'modernize the reporting dashboard.' He assumed that meant moving to a new design system, spent a month on it, and when he presented it, his boss said, 'Oh, I meant we should add a download button.' Lucas: Oh, that's painful. And it's such a perfect example of why you have to ask the basic questions first. Luna: Right. And the sad part is, he was so embarrassed that he never asked for context in the future. He just over-delivered on everything, hoping that would cover for the ambiguity. That's not sustainable. Lucas: No, it isn't. And it also highlights a key nuance: there's a difference between a boss who withholds context because they're insecure or territorial, and a boss who just hasn't thought it through. Your response should be different in each case. Luna: How do you tell the difference? Lucas: You test them. If you ask a genuine question and they get defensive or shut you down, that's a red flag. But if they say 'good question, let's figure it out together,' then they're just disorganized. In the first case, you might need to escalate or document everything. In the second, you can be more collaborative. Luna: And what about when you've asked the four questions, and you still get nothing? Then what? Lucas: Then you have to make a judgment call. You can either proceed with your best assumptions and clearly document them, or you can go one level up if the stakes are high enough. But I'd say, only escalate if the project is genuinely important and you're confident your boss's vagueness is going to cause real harm. Luna: Yeah, you don't want to be the person who goes over their boss's head for something trivial. Lucas: Precisely. And there's a technique for that too: you frame it as a request for alignment, not a complaint. Like, 'I have a few questions about the project scope, and I wanted to see if you and I and your manager could get on the same page.' But honestly, that's a last resort. Luna: Okay, so let's recap the practical steps: ask the four questions, if that fails, go find context yourself, and if that fails, decide whether to escalate. Is that about it? Lucas: That's the core. But there's one more thing I want to add, and it's about your mindset. When you ask for context, you're not just doing it for your own benefit. You're modeling good behavior. And eventually, when you're the one giving out tasks, you'll be the boss who provides context upfront, breaking the cycle. Luna: That's a nice note to end on. It turns a frustrating situation into a leadership opportunity. Lucas: And if you're in that frustrating situation right now, start with one question. Just one. See how your boss reacts. That'll tell you a lot about how to proceed. Luna: Thanks for joining us, everyone. We'll catch you next time.