Latest / New Manager Conversations with Fexingo: First 90 Days, Managing Former Peers, and Leadership Basics / How New Managers Can Handle a Direct Report Who Is a Friend
Transcript
- Lucas: So, you've just been promoted to manager, and one of the people on your team is your best friend from college. You've shared apartments, you've been to each other's weddings, you've seen each other through breakups. And now, you're their boss. What does that actually look like on a Tuesday morning at nine a.m.? Luna: That's a scenario a lot of new managers probably think about but rarely talk about out loud. It feels almost taboo, like admitting it means you're not serious about the job. Lucas: Right. But it's incredibly common. A survey from a few years back found that nearly one in three people have worked with a close friend, and for new managers, it's often the first awkward situation they have to navigate. The thing is, it's not just about feeling awkward. There are real, structural tensions between the friendship and the manager role. Luna: Structural tensions. Can you unpack that a bit? Lucas: Sure. In academia, they call it a 'dual relationship' — when two people occupy two different roles at the same time. And those roles have different expectations. A friend is supposed to be supportive, non-judgmental, on your side. A manager is supposed to evaluate, coach, and sometimes deliver tough feedback. Those two sets of expectations can directly collide. Luna: So what does that collision actually look like in practice? I'm thinking about, like, a performance review where you have to say something critical. Lucas: Exactly. That's the classic. You've been telling your friend for years that they're amazing, and now you have to sit across the table and say, 'Your presentation skills need work.' The friendship can make you soften the message so much that it becomes useless, or you overcorrect and come across as harsh. Both are bad. Luna: And there's also the reverse problem. I've seen cases where the manager bends the rules for a friend — giving them more leeway on deadlines, not holding them to the same standards. That's not just unfair to the rest of the team, it's actually harmful to the friend in the long run. Lucas: Absolutely. That's the 'friendship bias' trap. It feels like you're being kind, but you're actually doing them a disservice because they're not getting the coaching they need. And the rest of the team sees it. It breeds resentment and can destroy your credibility as a manager. Luna: So what's the first step? I mean, before you even have that first performance review. Lucas: The first step is to have an explicit conversation early on, ideally in your first week as their manager. Not a performance conversation, but a 'how we're going to work together' conversation. You say something like, 'Hey, we've been friends for years, and that's important to me. But now my job is to manage this team, and that means I have to make decisions that might not always be comfortable. I want to be transparent with you about that.' Luna: And what does that achieve, practically? Lucas: It sets expectations. It acknowledges the elephant in the room and gives your friend permission to talk about it too. It also draws a line between the two roles. You're not saying 'we're not friends anymore', you're saying 'we have two different contexts now, and we need to be clear about which one we're in at any given moment.' Luna: I like that. So it's about role clarity. And that conversation should cover some specific ground, right? Lucas: Yeah. There are a few key things to cover. First, how you'll handle performance feedback — that it will be direct, and it's not a personal attack. Second, how you'll handle sensitive information — like salaries, restructuring plans, that kind of thing. You have to be clear that you can't share confidential details with them just because you're friends. And third, how you'll handle social situations outside work. Luna: Social situations. That's the other minefield, right? Do you still invite them to your birthday party? Do you go to their wedding? Lucas: Right. And the answer is usually yes, but you have to be thoughtful about it. The friendship doesn't disappear, but you have to be aware of the dynamic. For example, if you're at a social event and a couple of other team members are there, you need to be careful not to appear to be favoring your friend. You also need to be clear that what's said at work stays at work, but what's said in a bar might not be. Luna: That's a fine line. So how do you actually manage that in practice? Lucas: The key is to establish some boundaries early on. You might say, 'When we're at work, I'm your manager. If you need to vent about your day, that's fine, but I might have to put on my manager hat and give you feedback. Outside of work, we can be friends, but I might not be able to talk about certain things.' It's about being honest about the constraints. Luna: And what about the rest of the team? They're watching how you treat your friend. If they see you being lenient or overly chummy, it's going to affect morale. Lucas: That's a real concern. The team needs to see that you're fair and consistent. One way to handle it is to be extra scrupulous about following the same processes for your friend as for everyone else. If you have a weekly one-on-one with everyone, you do it with your friend too. If you document feedback for everyone, you document it for your friend. You almost have to over-index on process to show that you're not playing favorites. Luna: That makes sense. But I also wonder about the friend's perspective. They might feel like you're treating them differently because you're being too formal or distant. How do you balance that? Lucas: That's the crux of it. You have to communicate a lot. Check in with them regularly, not just about work but about how the dual relationship is feeling. Ask, 'Is this working for you? Is there anything that feels off?' So often, the problems come from unspoken assumptions. If you both agree that you'll be transparent about the weirdness, it becomes manageable. Luna: It sounds like the friendship actually gives you a foundation of trust to have those conversations. Lucas: Exactly. In a weird way, a pre-existing friendship can be an advantage. You already have honest, direct communication patterns. You've seen each other at your worst. You know how to give each other feedback. The challenge is to deliberately apply those skills in the managerial context. Luna: That's a good reframe. So what are some practical tips for that first conversation? I'm thinking of a script or a checklist. Lucas: Sure. First, pick a neutral, private setting — not your office, maybe a coffee shop or a walk. Second, start by affirming the friendship. Say, 'You're one of my closest friends, and that's not going to change.' Third, explain the new reality: 'I'm now responsible for your performance and development, and I take that seriously.' Fourth, set the ground rules for feedback, confidentiality, and social stuff. And fifth, invite them to share their thoughts. Ask, 'How are you feeling about this? Is there anything you're worried about?' Luna: And then what? You have that conversation, but you don't just set it and forget it, right? Lucas: No, definitely not. You have to revisit it. Maybe once a quarter, or when something changes — like if you have to give tough feedback or if a promotion opportunity comes up. You check in: 'How are we doing with this? Anything we need to adjust?' It's a living agreement, not a one-time contract. Luna: And what about the situation where the friendship really does interfere with the work? Like, you find yourself avoiding giving feedback because you don't want to hurt their feelings. What do you do then? Lucas: That's when you have to lean into the role. You have a responsibility to the company and to your friend to be a good manager. If you're avoiding feedback, you're not doing your job. One thing that helps is to separate the person from the behavior. You can say, 'I value you as a person, and I also need to tell you that this specific behavior isn't working.' That's a classic feedback technique, but it's especially important with friends. Luna: And if it becomes so hard that you can't be an effective manager? Is there a point where you should consider recusing yourself or moving the friend to another team? Lucas: That's a legitimate option. If the conflict is too great, or if there's a perception of bias that you can't overcome, it might be better for everyone to have the friend report to someone else. But that's a big step, and it should be a last resort. Before that, you should try to make the dual relationship work with clear communication and boundaries. Luna: So, in your experience, is it more common for these situations to work out or to end badly? Lucas: Honestly, I think they can work out really well. I've seen managers and friends who are incredibly effective as a team because they have that deep trust. They can have honest conversations that other teams can't. The key is that both people are committed to making it work and are willing to be transparent about the challenges. It's not easy, but it's absolutely doable. Luna: That's reassuring. But I imagine there are some common pitfalls that you see over and over. What's the biggest one? Lucas: I think the biggest pitfall is not having that initial conversation. When you avoid the topic, the friendship and the manager role just blur together. You're in a meeting, and you're not sure whether you're talking as a friend or a manager, and the lines get crossed in a way that's confusing for both of you. That's when resentment builds. Luna: So the first step really is to have that awkward conversation early. Lucas: Yeah. And it doesn't have to be a horrible, heavy thing. It can be light: 'Hey, this is a bit weird, but let's talk about how we're going to handle this.' The fact that you're both aware of the weirdness actually makes it easier to manage. Luna: I like that. It's about naming the elephant in the room so it doesn't become a barrier. Lucas: Exactly. And that's a skill that goes beyond managing a friend. It's about being a good leader in any ambiguous situation — naming the tension and working through it together.