Best Friends Don't Make For the Best Bosses
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Welcome. Welcome. Thank you. Shall we listen together to the question that you send? And then if there's anything you want to edit, we can do so too. Okay. Okay. Yeah. Let's go.

My friend, who I've known since elementary school, decided to open a bookstore in 2019 and asked if I would work with him. And I said yes, and so we opened this bookstore together, and it was going really well. He was the owner and the manager and my boss, but it was really just the two of us there for a long time. But things eventually started to feel hard between us.

He, as I mentioned, was my boss, but he was also my really good friend and we didn't have any systems in place to talk about job performance or anything like that. So from my perspective, he just felt like he would randomly like make kind of snippy comments about things he didn't like that I was doing or that I could do better. And then I would get defensive and then it would feel tense for a while between us.

And that was escalating. And eventually after a couple of pretty big altercations between us where I was yelling and then he was like,

mad at me about that, I decided it was in my best interest to leave and in both of our best interests really so that we could stay friends. So I left, I got a new job and we are still friends and I still go and work there sometimes, but I'm really sad that it didn't work out. And he's really sad that it didn't work out. And I miss working there. I think I was really good at it.

And I'm just wondering if there's any scenario, a future scenario where it could be better there between us.

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Whatever you're into this holiday season, from streaming to shopping, it's on Prime. Visit Amazon.com slash Prime to get more out of whatever you're into. Good. That's a clear question. And anything you want to add, change? I guess just that I submitted this question a few months ago and then sort of just reconciled to the fact that, you know, it is what it is. I have this new job and, you

things happen the way they were supposed to happen. And so now, I don't know, it's just a little bit in the, a little bit further in the past than when I first wrote it. Tell me about, there's many ways I could start this, but just to get a little bit more context, how is your relationship or your friendship with him now? I think it's,

Okay, I think that we were able to talk a little bit after I left about how we were both sad. But I think that there are things that neither of us will say to each other. You know, I haven't said anything.

I left because I thought you were kind of being a jerk. You know, I haven't said those words. So I think that there are definitely things unsaid. But in general, we're in a good place and we love each other and we have no ongoing conflict. OK. Have you had an actual debriefing conversation? What worked best?

What are things that we overlooked? What are things that we didn't communicate about well? What are KPIs that we may have missed? How did we let the blending of the friendship and the liking and the feelings enter into a conversation that then could not address issues of competence and performance and outcomes and goals? Have you had that kind of, not just...

You don't tell your boss he's a jerk. No, no, no. And he was your boss. And that doesn't say much. It just means you didn't like what he had to say. Of course. Have you had a professional off-boarding conversation? No, I would say we haven't. I think we tried to do something like that. But I think to hear you say the word professional was striking to me because I don't think we ever...

figured out what our professional relationship was. And so, right. And so it could, yeah. So we've talked about it more as friends than as friends.

colleagues or co-workers or professionals. You remind me of an episode that I did with three men who had been playing together since they were young children. And that play turned into a production company. And they too struggled with the kind of formalizing of

of expectations, of boundaries, of accountability, of communication flow, of initiatives, you know, things that are not necessarily defined in a relationship, even though they are often implied in a friendship, but they're not made explicit. And if you ask me, do you think there's a chance this could ever happen again, that I could work with him again?

I would say yes, potentially, but it requires this transition.

Yeah. I was not very professional. I became defensive. I thought, you know, if we like each other, we should overlook these things. I didn't really like the sudden shift in power dynamic. And now you get to evaluate me. And I don't get to tell you what I really think because you are my boss. And all these things that muddled me.

That needs to be formalized and clarified if you ever want to have a professional relationship with a friend. That's the combination. You're trying to integrate these two. But it is an integration of two things. It's not just two friends working together. Yeah. I mean, I hear about couples who have businesses together, and I really just can't even understand how that works.

could possibly happen. And I do think there's probably some resentment on my part because since he was the leader, the boss, I think I was waiting for him to do some things like establish some job performance systems, stuff like that, that never happened. And maybe I used that as an excuse

to not rise to a more professional level. And does he do it now? Not that I know of. With the next person?

Well, he's been very slow to hire new people. He hasn't really replaced me. He's just sort of drowning there at the bookstore by himself. But he has a few part-time people. And to my knowledge, no, he hasn't. Okay. So if you came to him and you said, I want to take accountability for my part. I kind of left it up to you. I...

Since you didn't come, I didn't push. You know, this kind of I wait till you wait till I wait. And I think we have a lot that we can learn from this. Should we sit down and just to do a debrief together? We can see if there's ever an opportunity to try this again. I think it's a very interesting thing to rehire people that we had let go or that left. It can work very well. I've done it.

But it demands a clarification of defining the relationship, the terms of the relationship, a clear set of expectations, and a willingness to be very professional and not to try to diffuse the professional because we are friends, which I think is what I'm hearing you say. Yeah. I think I don't really know how to do that. I think I don't really know how to be professional professionally.

With my friends. I don't know. Tell me about you in the new job. I work at a school now. I'm professional there for sure, but I don't know. You know, it's... What does that mean, I'm professional? Yeah. What is being professional for you? Yeah, it means... It means, I guess it means I'm always focused on the work and why I'm there. And...

acknowledging the hierarchies that exist in my place of employment. Yeah. You show up. Yes, right. I show up on time. I stay until I'm supposed to leave. Yeah, I do all those things. I did that at the bookstore too, but yeah. Okay. So where would you say were your lags in the bookstore? Where were the leakages? I think the power...

dynamic was a struggle for me. I think I didn't feel, I wasn't sure how much freedom I had to be creative and share my own thoughts and ideas and where I was meant to just sort of do as I was told. And is that a question that you ever were able to bring to him? Did you have regular meetings?

set in the calendar where you looked at things from inventory to work culture to store culture to... We didn't have regular meetings because it was just the two of us. So all of our conversations were just, you know, folded into while we were both just standing there. Exactly. Yeah, exactly. Yeah. And this question in the course of this in-between conversations, were you able to ask him?

Is there an opportunity for me to share some of my ideas? I have some thoughts about how we could do this or... I'm trying to think. I don't know. I'm not sure how to answer that. I think I feel intimidated by him. He's very smart. He's like one of the smartest people I've ever met. And I think sometimes I just defer to him. And then he was my boss, so I defer to him. And sometimes I would have ideas that...

not in a mean way, but that he would sort of pivot away from and just end up doing his own idea instead. And so I think I just got the message or interpreted some message that maybe my ideas weren't so valued. We have to take a brief break, so stay with us and let's see where this goes.

Support for this show comes from Amazon Prime. However you plan to make the most of the holiday season, you can do it with Amazon Prime. Whether it's last-minute ingredients and stocking stuffers or a themed puzzle to solve with the family, get fast, free delivery on holiday essentials with Prime. And with Prime Video, you can curl up on the couch, warm drinks in hand, and have a holiday movie marathon. Throughout it all, you can tune into classic holiday playlists on Amazon Music.

Whatever you're into this holiday season, from streaming to shopping, it's on Prime. Visit Amazon.com slash Prime to get more out of whatever you're into. Imagine that you have an opportunity to meet him and to just start a conversation. You know, I was talking to this lady on her podcast. And the reason I brought this up with her was, what would you say?

I would say I brought it up because I wish things had gone differently. I wish we could have figured out how to be friends and work together. And I don't think we ever figured that out. And that was really sad and a disappointment to me. It was very sad. And

It was sad to him, too. I mean, it was very clearly sad. He was very sad when I left and very surprised when I told him I was leaving. So he may not even know half of what went through your head. So as I was talking to her, I thought, we really need more conversations about this. It's a pity. We've known each other our whole life. If we can't have this conversation, who can? So...

Here are things that I've been thinking about that I really would like just to think out loud with you. And I would love to listen for you to talk to me as well, because I think there may have been many misunderstandings, many unspoken moments, many things left on the cutting room floor. And here we are a little bit dazzled at this thing just unraveling like this.

And neither of us have actually really done a post-mortem. So I told this woman, Esther Perel is her name. Well, we have your book at our bookstore. So he knows you. Remember that woman and the book? Okay. So I went to talk to her. And here are the things that stood out for me that I realized that I have not really had an opportunity to share with you.

Then it's my turn? Yeah. You got it. Okay. That I never figured out how to be a professional with you, that I never quite figured out our roles, our boundaries, how our relationship needed to evolve to be a healthy working relationship.

So consequently, when you tried to talk to me about things that you wanted me to work on, it felt like my friend criticizing me and I felt defensive and didn't act my best. When I did what? When I snapped at you, when I got mad at you for giving me instructions. I'm going to role play him.

Did you hope that when you said I'm leaving that I would beg you to stay and put our friendship above our collaboration and run after you? I was hoping that you would try and figure it out with me, that we could figure it out together, how to make it work. I wasn't playing a game. I wasn't like saying I'm leaving and hoping that you would like talk me out of leaving. It wasn't that, but I was hoping

I did somewhere hope that it would be the impetus for change between us. But you didn't come to me saying, we need to talk. This isn't working out very well. We can do better. No. You had a fit and then you told me, I think I should go. That was your dramatic exit. And I don't like to force people to do things they don't want to do. Mm-hmm.

So you didn't give me a sense that you wanted to work something out. You gave me a sense that you are upset. Hot or cold? So here's what I did. After I, this sort of last instance, when he snapped at me about something and it was Black Friday, it was a stressful day anyway, you know, so I give him that. But I blew up. I got very angry.

And I, a couple of days later, came to him and apologized. And I said, I should not have spoken to you that way. I was very stressed out. You know, I like sort of took responsibility for my part of it. And he didn't really say much. Like he didn't, I don't know. I just got the impression that,

That wasn't going to be possible for us to have in-depth conversations like I wanted to. Based on his response to my apology, he just sort of like doubled down on his initial complaint. And so that is when I thought, I don't think things can change. I think I should leave. I didn't say it right then.

So he reminded you why he had snapped rather than showing you appreciation for your taking responsibility. And what did that represent for you? I wasn't looking for appreciation, but I was looking for him to say something about, you know, maybe I...

shouldn't have said that in the way I said it, or perhaps we could have talked about it at a different time, or just some acknowledgement that the communication between us on both of our parts was not excellent. And when it didn't even seem that he could see that, I kind of lost hope. But you know this man your whole life. Is this the first time you have a

misunderstanding, a skirmish, a moment when you do something that you think is for the benefit of the relationship and you feel that he's talking for the benefit of the point he's trying to make rather than protecting the relationship. We had never had an opportunity to really have a skirmish like that where we both were so invested in something. In being right. Yeah.

Yeah. In being right. When two people are invested in being right, then what? Yeah. Finish the sentence. I don't know. Someone has to say I was wrong or someone has to... I mean, both people can't be right, I guess. I don't know. I don't know the answer. What made you think when he continued to say...

Why he thought he was justified in being upset or mad. What made you give up like this? You could have, you know, I know this guy, I know how he gets, or it's not worth it. Our relationship is more important. Or what happened? What parts of each of you got uncovered there that it became so reactive? Yeah, I think he is...

not that willing to talk about his inner life. And, you know, it's weird because the way I responded to him when he would tell me things was not the way I would respond to someone who I hadn't known for 30 years. You know, that's, I would not have snapped at someone who was only my boss, not my friend. And so then the repair I had to do with him was also not

the kind of conversations I would typically have with someone who I only had a work relationship with. So I had never had such intimate conversations with him and his stubbornness, his, the wall he put up. I just, I didn't see how, how it could work. I just couldn't imagine a scenario where we could go forward and,

And the wall would be down and we would act like professionals, but we could still be friends. Like I just couldn't figure out how that could be possible. And so I thought, I think, and I didn't think he was ever going to fire me. So I thought, I have, I think I have to leave. Like, it's just, it's not going to get better. And none of that has been part of the conversation yet.

That is not a conversation that you have had even ever since. Correct? That's correct. Yep, that's correct. That's the conversation I imagine. I mean, part of what you're talking about, and especially when you say my reaction to him was sat on top of the fact that we know each other our whole life. I wouldn't react this way to someone I know less and that is actually in a more formal way, my boss. Yes.

You know, many of us wonder, can you work with your life partner? What is the essence of family business? What's it like when two close friends join forces and start working together? And they suddenly realize that co-parenting the store

brings out many differences between them. How do we straddle superposing different relationships that have different rules and different frameworks? It's a real challenge and an act of, it's an act of creativity and it demands tremendous communication skills. I think all work relationships do, but there is something even more unique when you have an overlap between

You know, one minute it's, you know, I talk with you about some very personal things. The next minute, you know, you're evaluating my returns. So lots of us want to know how do we do this? But what's interesting is that you used your familiarity to allow yourself to react to

And strongly. But you didn't use your familiarity to actually have the difficult conversations. And when I say familiarity, I mean the level of trust, the reliance on the solidity of the relationship. Suddenly you acted as if this relationship is uber fragile. Yeah. I am curious about that. I think I did try to use my familiarity to have conversations with him more.

But in retrospect, I don't think I did it in a way that was productive or, I mean, it didn't lead to the outcome that I was hoping for. For example? For example, him saying, this is hard. This is hard to be friends and to be a boss and employee. This is, we're going to need to come up with something.

some rules or some boundaries or go to therapy or take a course or I don't know. I mean, I really don't know. But like just some acknowledgement that things can't keep going the way they're going because I didn't know a way forward. This is all so new to me. And so we learned about selling books, but we didn't learn about this. Yep. And if he was here today, what do you think he'd say right now?

I think he would say that he's sad that I don't work there. I think he would say that he never could figure out how to talk to me in a way that was productive about performance stuff, like in a way that would lead to meaningful change. And I think he would probably say... So he was more focused on criticizing than improving?

He would tell you what was not right or what he didn't agree with or didn't like. Right. But he wouldn't tell you, I expect this. You have that many days to do that. This should be the result that we're hoping for and setting projections and goals. Yeah. And then I think he would probably say something self-deprecating, like that he was a bad boss or something, because he has a lot of negative self-talk, I think.

We are in the midst of our session. There is still so much to talk about. So stay with us.

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Join the ACLU today to help stop the extreme Project 2025 agenda. Learn more at aclu.org. Do you think you're going to use this conversation as a springboard to actually finally have the chat you've never had with him? Yeah, I think it would be a real waste if I didn't. That's right. So, yeah, I think I will. And I don't know what...

I don't know what my goal is, though, like at this point. You know, when I wrote the question, I really wanted to work there again. Like I wanted to figure it out so that I could work there again. And now I feel a little bit less clear that that's what I want. But I think regardless, we should still have the conversation. In order to? In order to be better people. In order to learn from...

Things like this. I mean, I just think having hard conversations with people, like I've learned so much from having hard conversations with people that I thought I'm going to die if I have this conversation. And then I had the conversation and I didn't die. And so I think just being able to talk to someone who you're close to is an important skill. And maybe that's how you want to start the conversation. I'd love for us to learn.

from our collaboration. Each of us for our own future and wherever we go from here, but also in our friendship, in our relationship. When you started, what did you imagine? And what are the things that you felt actually flowed nicely? And what are the things that you feel really became hurdles? And what did you wish you had done differently? And what did you wish I had done differently?

And what have you done differently since because you've actually learned something? And I think your line about we learn a lot about selling books. We didn't really learn much about being, in a way, co-founders of the bookstore and to nurture the relationship that was needed in order for the bookstore to continue to grow and establish itself, you know. Yeah.

The conversation at some point can include, have you ever thought that we could fix this? Did you think it was defunct? Do you think it was moot? Or did you actually think we could fix it? Did you think you would never fire me because you didn't have the guts to? Or did you actually think this should be able to work? I just don't know how to do it.

You know, if you're my friend and I know you well and you know me well, I shouldn't have to tell you what to do because if you know me that well, you should know it. That's one of the things that often happens is that we presume the deep inner knowledge that we have as friends and we transport it into the workplace and it doesn't work like that. Yeah. And I also think starting a small business is

running your own small business is so hard and stressful and isolating. And he was going through all of that at the same time, not to mention COVID, you know, so all of these things were happening during the first few years of the bookstore. And I think that there was just a lot of naivete on, on both of our parts about what it would take like spiritually, emotionally and spiritually to do this work together. Yeah.

The conversation will be a lot more useful if you don't do it as a blame session. But if each person basically looks at themselves and looks at the other and says, I wish we had, I would have loved to if. It's a very different conversation than you never did, you didn't tell me, you did this, you did that. As a rule, I think sometimes...

Between friends, it's the same thing. Between partners, between colleagues, you know, you can have a breach. And then at some point, people work their way back into a different collaboration that is much better. So I don't think once gone, gone forever as a rule. Sometimes.

But sometimes there's something very interesting by having created the cut that allows people to actually reflect back on what happened here. Why did this totally derail? What was our naivete? What have we learned? And then from there, it's not the same conversation between should we do it again or what happened? First one is a clearing of the slate. Right.

And it would be a lovely thing, actually, if you use this session, our conversation, and you say, I would love for us to listen to it together and use that to start the conversation that we haven't had. It becomes like a transitional object, you know, that you put in the middle. We both listen to it and we start this chat. Yeah. How is this? So it's great in theory, but...

I don't really know what steps to take next, like to say, hey, do you want to go for a beer? Like, I don't know, you know, like sort of that, like how to get to the point where we're talking about this. Like logistics, you know? What's happened to us has been on my mind. I don't know if you think about it often, but I do. And so I reached out.

to Esther Perel. I thought, you know, why not, basically. I reached out a while back, so it was interesting to suddenly revisit it now. And I would love for you to listen to my conversation with her and for us to use this as a springboard into a clearing of the slate together. Would you be open to that?

I think we kind of left a lot of things hanging. We have a lot of things unspoken between us. I think both of us care deeply about our friendship and we don't want it to suffer. But at the same time, I think if we really trust our relationship, then we need to trust that it's solid enough that it can really tackle this experiment that we had together and help each other understand the other side.

I think we probably have a good idea of our own side, but it's not clear that we have a good sense of what happened on the other side. You know, if you say no, it's totally fine by me. I mean, I know you're not your guy who doesn't particularly like to go and delve deep into your, you know, but I also think that it's a good thing to do an offboarding like that, a kind of a summarizing of what happened here, because I think we stand to learn a lot together.

So I brought you this tape. Here's the link for that matter. Listen to it. And here are my three questions for you. And I'd love for you to come back and you start next time with your three questions for me. So what would be your three questions? Oh, boy. Okay. What...

Will you critique them after I say that? I'm asking seriously because I don't know that these are the right ones. What they can change. It's really, I actually think that they can be the broader ones, you know. What are the things that you think actually worked really well? Because we could start with everything that didn't work. But is that the best way to start? There are a lot of things that worked quite well. How long did you work with him?

Four years. Okay, that's a chunk. That is a chunk. It's not like you stay there four months. I had no sense it was that long. See, in the four years, I mean, we overcame a lot of things. We actually learned a ton of things. I mean, God, opening a bookstore, it's not like, you know, an easy, easy thing to do. So maybe we start with what we did well, and then we continue with what we think we could have done better.

And then we continue with what we think we really flunked at. Yeah. You know? I like that. I really like starting with what we did well. Yeah. Four years, you know? And what of what we did is still present in the way that the things that the store is run. You know, how much did the launch really solidify the existence of this store? We launched it together.

Those are not questions about what did you feel when you said this? You know, we're not going into that zone at all. It may have unfolded there, but that's not where you start. Yeah. The store is in the middle of the discussion. The store was our project. The store is what we co-parented and co-founded. And we start by talking about our contributions to the store.

And the store was a dream for each of us, so it's our contribution to our shared dream. If we were to write a book about the story of two people with a long friendship who want to build a bookstore together, how would we start the story, right? You came on a day. I was honored that you asked me. It really touched me, and I had tremendous hope.

That this would work, that this would succeed. I think you're one of the brightest guys I know. And from here you continue. It's a lot of what you've already told me, by the way. Yeah, I can do that. But the recording of our conversation is part of being a stress diffuser because he will already have heard a part of it. And then you basically, now that you heard it, let me say it in person. Yeah, I hope I didn't say anything that was...

I don't know, offensive to him. I haven't heard anything that was offensive. I heard maybe things that he may say, that's not how I see myself, but that's okay. Otherwise, he'd be standing in front of a mirror rather than in front of another person. They see other things than we see. So I don't know the person, but I didn't hear anything that was in any form blatantly aggressive, hostile, offensive.

At all. Okay, good. But you will listen to it again first. And if you do find something there, you'll say, there may be things that I, as I hear them, I'm not so sure that that's all I think. I said it then, but there are other thoughts that I, you know, this is one conversation. You're saying certain things to me today. You could say very different things to me another time.

You're not defined by these words. Neither is your friendship defined by this narration of the story of your friendship and your professional collaboration. Yeah. Anything else you want to say or ask? I don't think so. Glad you did it or wished we had never found you? No, so glad. I'm so glad. Yeah, for sure. And I think I'm certainly not the only one

who's trying to have a professional relationship with someone that they love. Absolutely. Yeah. Absolutely. It really is filled with good intentions and so easy sometimes to lose the ability to marry these two relationships. So thank you very much.

This was an Esther calling. A one-time intervention phone call recorded remotely from two points somewhere in the world. If you have a question you'd like to explore with Esther, could be answered in a 40 or 50 minute phone call, send her a voice message and Esther might just call you. Send your question to producer at estherperel.com. Where Should We Begin with Esther Perel is produced by Magnificent Noise. We're part of the Vox Media Podcast Network.

In partnership with New York Magazine and The Cut, our production staff includes Eric Newsom, Destry Sibley, Sabrina Farhi, Kristen Muller, and Juliann Hatt. Original music and additional production by Paul Schneider. And the executive producers of Where Should We Begin are Esther Perel and Jesse Baker. We'd also like to thank Courtney Hamilton, Mary Alice Miller, and Jack Saul.

Support for this show comes from Amazon Prime. However you plan to make the most of the holiday season, you can do it with Amazon Prime. Whether it's last-minute ingredients and stocking stuffers or a themed puzzle to solve with the family, get fast, free delivery on holiday essentials with Prime. And with Prime Video, you can curl up on the couch, warm drinks in hand, and have a holiday movie marathon. Throughout it all, you can tune into classic holiday playlists on Amazon Music.

Whatever you're into this holiday season, from streaming to shopping, it's on Prime. Visit amazon.com slash prime to get more out of whatever you're into.