Latest / Interview Prep with Fexingo: Behavioral Questions, Case Studies, and Hiring Manager Insights / How to Answer the Tell Me About a Time You Managed Up Question
Transcript
- Lucas: Luna, I want to start with a confession. For years, I thought 'managing up' was just a fancy term for sucking up to your boss. And I think a lot of listeners might feel the same way. Luna: Oh, absolutely. It sounds like corporate-speak for 'learn to flatter the person who signs your paycheck.' But it's actually a real skill — and it comes up in interviews all the time. Lucas: Right. The prompt is usually something like 'Tell me about a time you had to manage up' or 'Describe a situation where you influenced a decision made by someone senior to you.' And it's one of the harder behavioral questions because you have to be honest about a challenge with a boss without sounding like you're complaining. Luna: That's the tightrope. You need to show you can navigate hierarchy diplomatically, but the story can't make your boss look incompetent, because then the interviewer thinks you're difficult to manage. Lucas: Exactly. And if today is useful to you — if you've ever struggled with this question or just want to hear a framework you can steal — the way we keep this show ad-free is through listener support. You can buy me a coffee dot com slash fexingo. It's how we keep doing deep dives like this without sponsors. Luna: Yeah, genuinely — if we've helped you land a job or even just think through a career move, that link helps us keep the lights on. Lucas: So let's talk about what a good 'managing up' story actually looks like. I want to use a real case from a product manager I worked with a few years ago. Let's call her Priya. Luna: I love a concrete example. What was the situation? Lucas: Priya was a mid-level PM at a B2B software company. Her VP of Product — let's call him Mark — was a classic 'numbers guy.' He only cared about metrics that moved quarterly revenue. Priya needed funding to build a data infrastructure layer that would enable better analytics across the product. But Mark saw it as a cost center, not a growth driver. Luna: So she had to convince someone senior to her that his own framework was incomplete. That's managing up in its purest form. Lucas: Exactly. And the first thing she did — and this is the key — was diagnose Mark's decision-making style. She realized he wasn't going to be swayed by technical arguments or long-term vision. He needed a direct line from the investment to a revenue outcome. Luna: So she reframed the project. Instead of 'data infrastructure,' she called it 'customer retention engine' or something? Lucas: Close. She didn't just rename it. She built a one-page business case that showed how the infrastructure would reduce churn by enabling a new feature: automated usage alerts for customers at risk of downgrading. She tied it to a specific dollar amount — $2 million in retained revenue over 12 months. Luna: That's smart. She spoke his language. But the interview question isn't just about the strategy — it's about the interpersonal piece. How did she actually approach him? Lucas: She scheduled a 15-minute slot, not a formal presentation. She walked in with a printed one-pager, no slides. She said, 'Mark, I think we're leaving money on the table with churn. I have a hypothesis that this data layer could help us keep customers longer. Can I show you the math?' Luna: She framed it as a hypothesis she wanted his input on — that's brilliant. It makes him a collaborator, not a target of persuasion. Lucas: Exactly. She also came prepared with a fallback: if full funding wasn't possible, she asked for a smaller budget to run a three-month pilot. Mark agreed to the pilot. Six months later, the full project was approved. Luna: So the STAR for that story would be: Situation — a VP who only valued short-term revenue. Task — get funding for a long-term infrastructure project. Action — diagnose his style, reframe the project in revenue terms, approach humbly with a one-pager and a pilot option. Result — pilot approved, then full funding, and ultimately reduced churn. Lucas: That's exactly the structure. But here's the trap a lot of people fall into: they spend too much time explaining why their boss was wrong. They say things like 'My boss didn't understand the technical debt' or 'He was too focused on quarterly numbers.' That sounds like a complaint, even if it's true. Luna: Right. The interviewer doesn't need to know how wrong your boss was. They need to know how you navigated that reality. Focus on your actions, not their flaws. Lucas: I'd add one more thing. The best managing-up stories also show some self-awareness. Priya could have said 'Mark was a narrow-minded spreadsheet jockey.' Instead she said 'Mark was driven by revenue metrics, so I learned to frame everything in that language.' That shows adaptability. Luna: It's also honest about the power dynamic. You're not pretending your boss was perfect — you're showing you can work with imperfect leaders, which is a huge green flag for hiring managers. Lucas: Let me give a counterexample. I once coached a candidate who told a story about convincing his CEO to change the company's pricing model. He spent two minutes describing how the CEO was 'stuck in the past' and 'resistant to data.' By the time he got to his action, the interviewer had already mentally checked out. Luna: Ouch. That story would have been great if he'd framed it as 'I researched competitive pricing and presented a data-backed alternative in a way that addressed the CEO's concerns about revenue stability.' Lucas: Exactly. The difference is framing. You can say the same facts, but the tone changes everything. Let me share a simple framework I've used with clients. I call it DFD: Diagnosis, Framing, Delivery. Luna: I'm taking notes. What's the first step? Lucas: Diagnosis. Before you approach your boss, figure out what drives them. Is it data? Relationships? Speed? Risk aversion? Priya diagnosed Mark as a revenue-driven skeptic. That's step one. Luna: And framing is where you tailor your message to that diagnosis. So for Mark, it was a revenue retention story instead of a technical infrastructure story. Lucas: Right. And delivery is the how — the tone, the medium, the ask. Priya used a one-pager, a humble pitch, and a pilot option. She didn't demand a decision on the spot. Luna: I want to push back a little. What if the boss is genuinely unreasonable? Like, what if you have a micro-manager who won't listen to any data? Should you still try to manage up, or is that a sign to leave? Lucas: That's a fair question. And I think the honest answer is: managing up has limits. If you've tried multiple approaches and your boss is still shutting you down, that's useful information for your career. But in an interview, you probably don't want to tell a story that ends with 'and then I quit because my boss was toxic.' Luna: Unless you frame it as 'I escalated to HR' or 'I documented the issues and eventually moved teams' — but even that is risky. Interviewers might worry you'll be a difficult employee. Lucas: Exactly. So for interview purposes, pick a story where you had some influence, even if it was partial. If you truly couldn't manage up in a past role, find a different example — maybe you influenced a peer or a cross-functional leader. Luna: That's good advice. I also think candidates underestimate how often 'managing up' can be about managing expectations, not just getting buy-in. Lucas: Yes! That's a whole other angle. Sometimes managing up means telling your boss 'We can't hit that deadline with current resources' and proposing a realistic alternative. That's still influencing upwards. Luna: And it shows you're proactive about trade-offs, not just a yes-person. I've seen stories like that land really well. Lucas: Let's wrap with a quick summary of what listeners should take away. First, pick a story where the result was positive, even if the process was messy. Second, use DFD — Diagnosis, Framing, Delivery — to structure your narrative. Third, avoid bad-mouthing your boss at all costs. Luna: And practice it out loud. The STAR structure is great, but if it sounds rehearsed, it loses impact. Record yourself and listen for any defensive or complaining tone. Lucas: Good point. If you try this framework, let us know how it goes. And if you found today useful, you know where to find us — buy me a coffee dot com slash fexingo. It's what keeps episodes like this coming. Luna: Next week, we're tackling a question I know a lot of you dread: 'What is your greatest weakness?' We'll have a fresh take on that one. Lucas: Can't wait. See you then.