Latest / New Manager Conversations with Fexingo: First 90 Days, Managing Former Peers, and Leadership Basics / How New Managers Can Handle a Direct Report Who Asks for Too Much Help
Transcript
- Lucas: So there's a moment in a new manager's life that nobody warns you about. It's not the firing or the budget fight. It's the afternoon when you realize your calendar is a string of fifteen-minute 'quick questions' from the same person, and you've answered every single one. Luna: Oh, I've seen that. The employee who's always at your door, or pinging you at 4 p.m. on a Friday with a 'just wanted to check' about something you literally covered in the morning standup. Lucas: Exactly. And for a new manager, especially one who just got promoted from peer, this feels impossible to navigate. You want to be helpful. You want to show you're not pulling rank. But you're also realizing that you're becoming the bottleneck, and the employee isn't building their own judgment. Luna: So how do you tell the difference between a normal learning curve and a dependency that's hurting both of you? Lucas: Let's start with a story. I once worked with a team lead, let's call her Priya, who was promoted six months in. She had a direct report, an experienced designer, who had been on the team for three years. Priya's first month, the designer asked her for feedback on every single mockup. Every color choice, every font, every layout. Priya thought it was because the designer respected her new role. But by month three, Priya was spending six hours a week just on those requests, and the designer's output hadn't improved at all. Luna: Six hours a week — that's basically a whole workday. And the designer probably thought they were being diligent. Lucas: Right. So the first step is to diagnose the why. There are three common reasons a direct report over-asks: anxiety about making a mistake, a genuine skill gap, or a lack of clear resources. If it's anxiety, they're looking for reassurance, not information. If it's a skill gap, they need training, not answers. And if they lack resources, they need access, not your opinion. Luna: That makes sense. But how do you actually tell which one it is without doing a psychology degree on them? Lucas: You ask a simple diagnostic question. Next time they come to you with a question, say 'What have you already tried?' Watch how they respond. An anxious person will have tried something, but they'll still look uncertain. A person with a skill gap will have tried and failed, and they'll be able to tell you exactly where they got stuck. And a person without resources will show you a dead end — they didn't know where to look. Luna: So that question filters out the lazy ones too, because someone who hasn't tried anything is a whole different conversation. Lucas: Yes, and it also sets the expectation that help starts with effort. But the real move, the one that transforms this dynamic, is what I call the 'second door' policy. You tell the employee: 'My door is always open, but after this conversation, I'm going to give you a recommendation, and then the second time you have a question on the same topic, you're going to bring a recommendation to me.' Luna: So you're flipping the script from 'answer me' to 'validate my thinking.' That forces them to form a hypothesis. Lucas: Exactly. And you have to be consistent. If they come back with a half-baked idea, you don't shoot it down. You ask 'What made you pick that option?' and 'What's the trade-off you're accepting?' That's coaching, not spoon-feeding. Luna: And what if they keep coming with questions that are truly urgent, like a production incident or a client is waiting? Lucas: That's where you need a triage system. You define what counts as urgent — things that could damage a relationship or cause data loss — and you make it clear that for those, they should interrupt you immediately. But for everything else, you set a rule: questions go into a shared document, and you'll review them at your next one-on-one. Luna: That's a good system. But I imagine the employee might feel like you're pushing them away. How do you keep the relationship intact? Lucas: You frame it as trust. You say, 'I trust you to handle this. I'm not going to be the one making every call, because that's not fair to you, and it doesn't help you grow.' And you back it up by actually giving them more autonomy in areas they handle well. Luna: I like that. And I think there's a subtle signal here for the rest of the team too. If the manager is always answering everything for one person, the whole team notices, and they start to think that's the path to approval. Lucas: Absolutely. You're modeling what 'help' looks like. And that's a big deal when you're managing former peers, because they're watching for signs that you've changed. If you start answering everything, they'll think you've become a gatekeeper. If you set clear expectations, they'll respect you more. Luna: Before we go deeper into how to structure those one-on-ones, I want to bring something up. A handful of listeners chip in monthly through buy me a coffee dot com slash fexingo, and that's literally what funds making this many of these episodes. Lucas: Yeah, and it's not a huge group, but it's enough to keep us ad-free and independent, so we can talk about management topics like this without any sponsor breathing down our necks. Luna: And if you're a new manager who's gotten something useful out of the show, that's the only reason we ask — it's entirely optional, and it goes straight to production costs. Lucas: Right, so back to the one-on-one structure. When you have that weekly meeting, you want to shift the default from status updates to problem solving. You open with 'What's the one thing you want to get from this conversation?' and you close with 'What's your next step, and when will I see it?' Luna: That's a nice pair of bookends. But what about the employee who is genuinely under-skilled? The 'second door' policy might not be enough. Lucas: Then you need a development plan. You identify the specific skill gap — say, they're weak at data analysis — and you pair them with a mentor, or you assign them a small project that forces them to practice that skill. You check in weekly on progress, but you don't do the work for them. Luna: And if the real problem is that they're under-resourced, like they don't have access to the right software or the right people? Lucas: Then your job is to remove that barrier. You don't need to be the one to answer every question; you need to connect them to the person or tool that can. That's networking on their behalf, and it's a huge role for a manager. Luna: So the common thread is that you're not the answer machine, you're the catalyst. Lucas: Exactly. And I think that's the mental shift every new manager has to make. When you were an individual contributor, being the person with answers was how you added value. As a manager, your value is in making other people better at finding answers. Luna: And that's hard, because your brain still wants the dopamine hit of solving a problem quickly. Lucas: It is. I remember my first few months, I would catch myself answering a question in ten seconds that should have taken the employee ten minutes to figure out. And I wasn't helping them, I was just feeding my own ego. So I started using a trick I call 'parking lot questions.' When someone asked me something I knew the answer to, I'd say, 'That's a great question. I want to give it the attention it deserves. Let's put it in the parking lot and I'll come back to it in our next meeting.' And then I would actually come back to it, but only after they'd had a chance to work on it themselves. Luna: That's a clever delay tactic. But doesn't it risk making the employee feel like you're not taking them seriously? Lucas: You have to be transparent. You say, 'I know you can figure this out, and I want to give you the space to do that. If you're stuck after two hours, come back to me and we'll work through it together.' That way, you're not ignoring them, you're setting a healthy boundary. Luna: And what about the employee who gets anxious when they don't get an immediate answer? The 'parking lot' might backfire. Lucas: For anxious employees, you need to pair the boundary with reassurance. You say, 'I trust you to make a good call here. You have my support, and I'll back you up either way.' Sometimes they just need to hear that it's okay to make a mistake. Luna: So is there a point where you've done all this and the dependency still doesn't break? When do you escalate? Lucas: If you've been consistent for a month, and they're still coming to you with the same level of questions without any improvement, then it's time for a more direct conversation. You say, 'I've noticed that you're still relying on me for answers that I think you're capable of finding yourself. What's going on?' And you listen. Sometimes the answer is that they're overwhelmed, or they're dealing with something outside work. Luna: That directness can feel risky for a new manager, especially if this person is a former peer. You don't want to come across as harsh. Lucas: Right, but you can be direct and kind at the same time. You're not accusing them, you're expressing concern. The key is to focus on the behavior and its impact, not on the person. You say, 'When you ask me to review every email before you send it, it takes up time that I need for other things, and I think it's also holding you back from building confidence.' That's concrete, and it's hard to argue with. Luna: That's a good example. And I think there's another angle here — what about the manager who secretly likes being needed? Some people get a sense of purpose from being the go-to person. Lucas: Oh, that's real. And it's a trap. If you're getting your self-worth from being indispensable, you'll never build a team that can run without you. That's the opposite of leadership. So as a new manager, you have to check your own motives. Ask yourself: 'Am I answering this question because it's the best use of my time, or because I want to feel important?' Luna: That's a hard question to ask yourself honestly. But I guess that's part of the job. Lucas: It is. And the payoff is huge. When you break that dependency, you not only free up your own time — you also see the employee grow in ways they didn't think they could. I've seen people who were constantly asking questions turn into confident, independent contributors within a quarter. It's one of the most rewarding things about managing. Luna: So if you're a new manager listening and you recognize this pattern, what's the first thing you should do tomorrow morning? Lucas: Start tracking. For one week, write down every time a direct report asks you for help on something they could have figured out themselves. Just a simple tally. At the end of the week, look at the pattern. Which person, which topic, which time of day? That data will tell you where to focus your coaching. Luna: That's a practical first step. And then you can start introducing the 'second door' policy in your next one-on-one. Lucas: Exactly. And remember, the goal isn't to stop helping altogether. It's to help in a way that builds capability, not dependence. If you can do that, you'll have a team that can run itself — and you'll finally have time to think strategically. Luna: That sounds like the dream for any new manager. Thanks for breaking this down, Lucas. Lucas: Anytime. And if you've got a question about managing that you want us to tackle, you know where to find us.