transcript of “The Friend Boss” (Ask a Manager podcast episode 1)

This is a transcription of the Ask a Manager podcast, episode 1: “The Friend Boss”.

Alison: Hi, I’m Alison Green. Welcome to the Ask a Manager podcast. Some of you may know me from my website,, where I answer daily questions from readers about how to navigate all sorts of sticky situations with coworkers, managers, and employees. Each week on the show I’ll take calls and talk directly with listeners about the toughest, most frustrating, or just plain weirdest work predicaments they’re facing. I’ll help you figure out what to do and say to handle these situations successfully and get the outcomes you want. So let’s get started.

Alison: One question that I get a lot at Ask a Manager is about managers and friendships. This comes up in a lot of different ways. Sometimes I hear about a manager who’s thinking about hiring a friend, and wondering about how to manage someone who they have a friendship with outside of work. Sometimes it’s questions about where the boundaries should be, like when a manager and an employee get along really well, and in other circumstances might become friends, but the power dynamics make that kind of weird. Sometimes it’s even about what to do if your boss wants a closer friendship than what you want, and how to set boundaries without offending the person who controls your paychecks. This week our guest is someone who already has a good friend at work, a person who has been a peer up until now, but now that friend is becoming her boss. I want to note before we bring our guest on, I’m not going to use her real name since like most people, she wants to be anonymous when discussing work issues. Hello, and welcome to the show.

Guest: Hi!

Alison: Thanks so much for joining us.

Guest: Oh, you’re welcome. It’s my pleasure to be here.

Alison: Why don’t you start by reading the letter that you initially sent into me, and then we’ll talk about it?

Guest: Okay! Hi Alison. I have read your column every day for almost two years and it has helped me tremendously in my career. I am hoping you can help me with this situation that just arose today. My work best friend has just been promoted to be my supervisor. Let’s call my friend and soon to be supervisor Marcia. Marcia and I became customer service trainers on the same day, three and a half years ago, and have taught almost every class together since then as training partners.

I did not apply for the customer service coordinator promotion that she just received, and I’m very happy that she got it. I know she will do a fantastic job, but I am now unsure of what will happen with our work relationship because she will be my direct supervisor. Marcia is a wonderful person and we’re close friends both inside and outside of work. Although we work for a great company, the department we’re in is incredibly micromanaged and is extremely stressful. As my training partner, we fill each other’s gaps. She is strong where I am weak and vice versa. We have been a sounding board for each other when we need to blow off steam and she knows all my shortcomings. She also knows that I have really struggled in my position in dealing with the management of the department and that I wanted to transfer to another area. I don’t know how to navigate this new work dynamic. Can I still come to her with work-related issues when they have to do with my weaknesses? I’m assuming I can’t gripe to her anymore; I would never do that with my boss. Can we still go out to lunch together? I don’t want to lose her as a friend, but I also don’t want to disappoint her as my new boss. Have any wisdom for me?

Alison: This is so tricky, as work friendship issues always are. You’ve had one type of relationship and now it’s going to be something else. That’s always tough to figure this out. Tell me a little bit more about your friendship. You said that you’re friends outside of work. How often do you see each other outside of work and how close would you say you are?

Guest: I’m single. She’s married and has three kids, recently adopted two children that are very young, and so her outside of work life is very demanding. However, we really care about each other a lot. Our relationship outside of work, besides the occasional shopping trip every once in a while or an event, is more calling and texting when something’s going on with our families. “How are you doing? How can I pray for you? What’s going on?” It’s not necessarily a spend a lot of time together friendship, but it’s a real deep personal caring about each other relationship.

Alison: In some ways, the fact that you’re not in the habit of spending a lot of time physically together outside of work will maybe make this easier. Maybe not, but it’s potentially helpful. Is she new to managing, do you know if she’s managed before?

Guest: She hasn’t officially managed before. As a customer service trainer, we manage our classes and supervise our employees while they’re in class for seven weeks. Even down to approving their time, handling disciplinary issues, things like that. She’s also been over the last year in a senior customer service training position, where she doesn’t have any management roles, but has a lot of extended roles – training the trainer, if that makes sense. But this is her first official management position.

Alison: I asked that because I think often for new managers in particular, this can be really tough to navigate. New managers tend to be very optimistic about thinking that they can maintain work friendships with people they’re managing, but sometimes it’s hard enough just figuring out how to manage when you’re new to it. Throwing in a friendship on top of that tends to make it extra challenging. Are you the only person she’s managing or is she managing other people too?

Guest: Right now there will be three of us. I was the only one that she’s close with, but there will be also a new customer service trainer hired to fill her position, and that will make four total.

Alison: Got It. I’m asking that because that can kind of impact this too. If she were just managing you, most of my advice would be the same, but I’m going to throw in some additional advice because the fact that there’s other people who might worry about favoritism if they see your relationship is relevant. Okay, I’m going to stop asking you questions now. I’ll try giving you some advice. Jump in anytime you want if you feel like I’m getting off base.

Guest: Okay.

Alison: So I do think the relationship needs to change – and that’s probably not what you were hoping to hear, but there’s power dynamics now. Her job is to assess your work and give you feedback and sometimes corrections, and maybe tell you things that don’t make you happy, and maybe even be the face of those decisions. And she’s got to be able to do that objectively without worrying about hurting the feelings of a good friend, or worrying that it’s going to make things weird when she’s seeing you socially later that week. She’s going to know things that she can’t share with you, she might need to make decisions that will impact your job in ways that you don’t like.

And then on your side of it, in some ways the power dynamics are even weirder for you. Because your job now is at least in part to make her happy, and that’s a pretty strange thing to have with a friend when it’s one-sided. Even when the person is reasonable – and it sounds like you guys have a really great foundation of friendship and mutual respect – it can still be a little weird when it’s one-sided like that. And it can be pretty uncomfortable to get critical feedback about your work from the person who you were just hanging out with socially the weekend before.

The other thing is, even if you were both able to navigate that perfectly – and most people don’t, but let’s say for the sake of argument that you both could navigate it perfectly – this is where you’ve also got to think about how it will look to the other people she’s managing. And then it’s human nature. Even if she is being very objective with you, people are likely to think that she’s not being objective with you, and they can end up thinking that she’s favoring you when it comes to assignments or perks. Or they might even feel like, if there’s some issue that they’re having with you that normally they would bring to their boss, they might hesitate to do that if they know that the two of you have a close relationship. So for appearance’s sake, if nothing else, the dynamics need to change a bit.

Guest: Right.

Alison: Now I know you don’t want to lose her as a friend, and I certainly understand why – it sounds like it’s a really great friendship.

Guest: Yeah.

Alison: I think you can’t stay friends in the same way while she’s managing you, but you can have a very warm, very friendly relationship with her – and I’m making a distinction there between friends and friendly, which I think is crucial here. You’ve both got to have different boundaries now. You can still talk, just keep it a little bit more professional. You know, talk about music or books, or talking about your family is fine, or whatever it is that you’d like to discuss. I would just stay away from things that are maybe more intimate than that. And I think you’ve got to pull back on how much time you might be spending together – a lunch or happy hour now and then is totally fine, just like she might do with another coworker. But if she’s doing it with you, she needs to do it with the other people she’s managing too, because otherwise that’s when it’s going to start looking like favoritism or special treatment.

Now I will say that in my experience, people in your shoes and in her shoes tend to hear this and think, “Oh no, we’ll be the exception, we’ll be able to make this work.” So I’m curious about whether you’re thinking that right now.

Guest: Well actually, I have thought through a lot of the things that you just said, and it was a pretty quick promotion. They decided they were hiring a second coordinator – there is already one coordinator who was everybody’s boss, and now they’ve split that job – and the job came open and she was hired, and had no idea that when they chose her, she would – they chose her on Friday, she started on Monday. Although she doesn’t start managing anyone until the next pay period, so two weeks. But I actually thought about a lot of this and so before she officially got the job on Friday, I said, “Let’s go to lunch and kind of talk through some of this.” And to be honest, I think she was a little surprised to hear a lot of that. But I gave her a card and I said, “I just want you to know I’ve got your back. I’m not jealous, I didn’t want this position, I think you’re going to do a great job. I think things need to change and that’s why I wanted to set up this lunch before we probably can’t do this again.” And it was a little awkward, but I think she appreciated it. Does that make sense?

Alison: Absolutely. Yeah. I think that’s the perfect approach. I’m so glad that you did that. I know she seemed a little taken aback. She may not have seen that coming. By the end of it though, did you feel like it was resonating, and she got what you were saying?

Guest: Yes, yes. I ‘m a planner, and she’s not, really. So I get the feeling maybe she hadn’t thought through all of this, although she did say someone gave her a book about how to manage friends. (Laughs) So she is starting to think about it.

Alison: Good. No, I think that sounds beautifully handled. That’s perfect, I’m so glad you talked to her. I know you had also asked in your letter about can you still vent to her, or gripe about the stuff that’s frustrating you with your job. You’re right to figure that you can’t really vent to her now that she’s your boss, even if she seems open to it, which she might seem – but that’s treating her as a friend rather than a boss. It could potentially impact you in ways that aren’t immediately obvious, that could come up down the road. Like you might think that you’re talking to her more as a friend, and then something from that conversation ends up in your performance review.

Guest: I was just thinking the same.

Alison: It’s not that she would intentionally be misleading you about which hat she was wearing when, but it’s hard for people to compartmentalize in that way. So I think it’s good to be smart about that, but you can continue to go to her with work-related issues that aren’t venting. You mentioned sometimes you talk to her about work-related weaknesses, and I think you can still do that, as long as you would do it more or less in the same way you would do it with another boss, assuming you were working for a good manager without the friendship issues in play. Say you wanted to say that you feel like your weak in area X, for example, and ask for her input or her feedback. Putting it in that kind of constructive action-oriented framework is the way to go. Does that make sense, and is that the kind of thing that you had in mind?

Guest: Yes, I just think that it’s always awkward. You know, when you’re talking with a friend who’s not judging your performance, it’s different than talking with a boss who, as you said, is going to keep everything you’ve said in mind. It’s their job to do so. I’m just trying to think about, how do I do it with my current boss, that’s not going to be my current boss in two weeks, and kind of transitioning that mindset over. I would never go in and say, “I am miserable here,” which I’m not, but “I’m miserable and I’m so stressed and I don’t think I can take this anymore.” I would never do that to a boss. I just am trying to train and remind myself that I can’t do that with Marcia anymore.

Alison: Yeah, that’s smart. There is a certain vulnerability that you might bring to the conversation when it’s not your boss and it’s just your friend or a coworker that doesn’t really work for the relationship when the person is your boss. But it sounds like you’re being so thoughtful about this and you’re covering all the bases that I would recommend that you covered. And it sounds like the relationship itself is a very good one and that while it has to change, I think you have a pretty good chance of it evolving into something that’s different, yes, but is still a good thing to have at work and in your life.

Guest: Good, good. It’s kind of good to say it out loud and to hear the things that I thought being repeated back.

Alison: Yeah, I think it’s going to go okay. And I think too, the fact that the conversation was awkward is totally fine and normal, and sometimes people have the awkward conversation and the fact that it felt awkward makes them second guess whether they were right to have it. The awkwardness, is it a signal that that was weird and I shouldn’t have done it? But this is just an inherently awkward thing. There’s no way around that except through it, and I think it’s great that you just jumped in and talked about it. Hopefully that helps.

Guest: Yes, it does. Thank you!

Alison: This is really hard. And I hope this was helpful and maybe you’ll send in an update in a few months and tell us how it’s gone.

Guest: Absolutely, I will totally do that. Thank you, Alison.

Alison: Thanks for listening to the Ask a Manager podcast, produced in conjunction with Penguin Random House and Anchor FM. If you like what you heard, please take a minute to subscribe, rate, and review the show on Apple Podcasts, or Google Play. If you’d like to ask a question on the show, email it to And check out my new book from Ballantine Books called Ask a Manager: Clueless Coworkers, Lunch-Stealing Bosses, and the Rest of Your Life at Work. It hits stores May 1st, and it’s the ultimate guide for tackling any and all workplace dilemmas. You can pre-order a copy today at or anywhere books are sold.

Thanks for listening! I’m Alison Green, and I’ll be back next week with another question.

Transcript provided by MJ Brodie.

You can see past podcast transcripts here.