is it OK to take vacations and share clothes with your boss?

At Slate today, I wrote about managers who try to be BFFs with their employees … raising concerns about favoritism and objectivity, sometimes pushing for more intimacy than their employees want, and generally overstepping boundaries. There are stories about a manager who took expensive spa vacations with an employee, a boss who regularly broke into tears while sharing unwanted personal confessions, and more! You can read it here.

{ 95 comments… read them below }

  1. Antilles

    is it OK to take vacations and share clothes with your boss?
    No. No. No. Pack your own suitcase.

    1. Kathleen_A

      I was once lectured about becoming “too friendly” with one of the members of my organization’s board – none of who had any authority over hiring, firing, raises, bonuses, promotions, etc. – by a man who, in just a couple of weeks, was going on a vacation during which he and his wife were going on a cruise with the president of the organization (who most definitely did have that authority) and his wife. Ah, irony. Or something.

    2. Nancie

      You think you’re joking. I know a guy who literally took nothing but his ID on a business trip. He sponged off everyone, for everything.

      1. Kathleen_A

        Why would anybody except possibly a homeless person be willing to share *underwear*? So weird. But thanks so much for sharing!

        1. Not a Mere Device

          I sometimes share underwear with my girlfriend–but it feels like the rules/boundaries in that sort of long-term relationship are different than with my other friends. (At her suggestion, I leav clothes there when I stay over, rather than putting dirty laundry in my bag, so this is usually because she didn’t get around to the laundry, or is staying at my place unexpectly.)

  2. Shades of Blue

    I don’t even need to read the article to know the answer to this is ‘NOOOOO!’

    :)

    1. MagicToilet

      Short answer: No

      Long answer: Noooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo

  3. NotAnotherManager!

    I was very good friends with a former boss, and that’s a hard no from me. It creates too many problems and perceptions of favoritism. (I often felt my former boss was harder on me than others to prove that there was no favoritism, actually.) We would socialize with his family outside of work only if others were there, and when we did lunch together, it was with several other members of the department and open to all.

    1. Shock & Naw

      You just made my head explode. I, too, have a friend relationship with a former boss and wondered why they seemed to scrutinize my work more than others (when my work history and output has always been stellar). You just gave me perspective.

  4. Almost Violet Miller

    I had a boss who would message me on Google Hangouts before I joined the company. That was already strange.
    When I moved to the area where my job was (it was still more than a month before my start date) he invited me for drinks after work. That’s when I realized he was an oversharer: he told me about his first marriage, his divorce, his second marriage, being a dad… I was overwhelmed.
    I was his first hire so he was overly enthusiastic. Also he had been promoted and became the manager of his former peers so he wanted to make sure he still appears friendly to his team.
    But no, please have some boundaries! It was exhausting to be this involved from day 0. Not that this should be default at any point.
    (I must add he was excellent in his field and not a bad boss at all but he had to learn to keep a professional distance. But I don’t know if that happened because I left for a more challenging position in a couple of months.)

  5. Ali G

    Old Toxic Job was a mess with this. The two co-founders were grad school buddies who then populated the C-Suite and other high level jobs with their buddies from their former careers. When they did hire outside their circles it was so obvious who was “in” and who wasn’t. It’s pretty hard to navigate issues when your boss and the VP have already decided what they are going to do about some issue during their group Father’s Day BBQ or whatever they did over the weekend together.

  6. Lily Rowan

    I’m way more circumspect with work friends ever since my buddy got promoted to be my boss. She went mad with power, but we were already Facebook friends, used to hanging out outside work, etc. I did ease off on all of that, and it was fine, but I wish I hadn’t been in the position in the first place.

  7. JosiePcat

    I kind of feel the same way about coworkers. It becomes really weird if they end up being your boss. True story.

    1. The Original K.

      Yeah, I have a friend who became very close with a colleague and then the colleague was promoted. When they became friends, my friend was new to the company and her colleague had been there for a few years and was a notch above her on the ladder, though they both reported to the same boss. That boss left the company suddenly (voluntarily; her husband got a new job out of state) and my friend’s colleague was promoted into that position. It was a mess. Colleague-turned-new-boss asked my friend to be in her wedding and my friend was in knots over what to do. She knew she should say no and she didn’t want to do it, but she was like “She’s my boss so do I have to?” All her friends, including me, said she shouldn’t. She ended up saying no and it was very awkward. (She no longer works there, though it’s for reasons unrelated to that.)

    2. MagicToilet

      Yeah that can be weird.

      Like, okay Michelle, I’ll do thw thing because you’re telling me to do it. But you hardcore vented to me about how this is a stupid and worthless the thing is 2 months ago over chips and guac. I know you’re only making me to do the thing because someone else is making you do the thing.

    3. Anonymosity

      Yep, this happened to me once. I went to work with someone I’d been friends with for years and she ended up being my boss. That did not go well when the job didn’t work out for me (I had a severe depressive episode at the time and ended up getting fired). We’re still friends but mostly on Facebook now. NEVER AGAIN.

    4. Detective Amy Santiago

      This happened to two of my former coworkers. They hung out a lot outside of work and then Kimmy got a promotion and ended up managing the team Jacqueline was on. Not long after that, Jacqueline’s husband left her and she ended up crashing on Kimmy’s couch for a while. It was super awkward for both of them, but Jacqueline didn’t have any family in the area and couldn’t afford her own place immediately (because she had been working to support her and her husband while he was in school – yeah, he was a real jerk).

  8. lionelrichiesclayhead

    I really feel like Alison could do a regular “one word response” post where the answer is so clearly Yes or No that it requires nothing more, or the question is so simple that the response can be as simple too.

    1. Detective Amy Santiago

      The subject line could be “The answer is Yes” or “The answer is No” and then in the body she can just post a list of questions.

      1. OhNo

        Ha! I like this idea. It might be fun for a one-off or round-up post to clear out some of the questions Alison normally wouldn’t have time to answer.

  9. MagicToilet

    For a time, I worked in the same department as my very best friend (I call her my younger sister now, that’s how close we are).

    She was promoted to my boss against her will. It was awful. It was like losing a friend. We both hated the situation. After 3 months, she quit the company (after 8 years of tenure) because of it.

    My 2nd very good friend was my boss for 6 years. I very much did not like him when I first met him. He was controlling and micromanaging, but we grew to understand each other and became friends. But it wasn’t until after I left his company that I was able to be true friends with him.

    I think boss-employee friendships are rarer than male-female friendships-with0ut-sexual-tension.

    1. Washi

      As it should be! It’s rarely a good idea for a boss and employee to be genuine friends, where as genuine friendships between men and women are lovely.

    2. SometimesALurker

      “I think boss-employee friendships are rarer than male-female friendships-with0ut-sexual-tension.”
      I disagree with the idea that male-female friendships without sexual tension for several reasons, but we can agree to disagree on several of them. However, can you please not assume that everyone you know is straight? You may not think you’re doing it, but if you assume that male-female friendships without sexual tension are rare, you’re probably projecting your own experience onto people in an inappropriate way. This post wasn’t even about that!

      Signed, a bisexual woman who does not have sexual tension with every friend who likes women

      1. MagicToilet

        I don’t assume. That’s unkind of you to assume I do. And you are assuming I am straight.

        It was employing a common trope everyone would understand.

        1. SometimesALurker

          Yes, it’s a common trope, but it’s a harmful trope, which is why I tried to explain why it’s harmful.

          1. SometimesALurker

            Sorry, hit enter too soon — I also meant to say that I didn’t mean to derail the conversation, but your lighthearted comment felt like a derail to me (even though you probably didn’t intend it that way), which is why I wanted to mention it.

          2. MagicToilet

            Ok well If I could delete it, I would. I never meant to cause harm (and I don’t believe that it is harmful, but I know it is best to acquiesce to those that feel harmed or wronged).

    3. MagicToilet

      Alison, is there a way to request that our comment be deleted? I can already tell this one is going to bring on critics, and I just wanted to contribute. Thank you.

      1. MagicToilet

        To be clear, I wish I could delete my comment. I naturally would never request you delete someone else’s comment.

    4. Student

      My bosses go out of their way to hire and work with their friends.

      Most of my friendships with the opposite gender are sexual-tension free. The friendships don’t last very long, otherwise.

      YMMV.

  10. Merteuil

    I don’t like the advice to say “I’m old-fashioned about boundaries at work,” implying that not having boundaries is somehow modern.

    You shouldn’t have to seem old or out of date to want to separate work from your personal life.

    1. MagicToilet

      Agreed that it SHOULDN’T but I’m constantly surprised at the number of people who friend their boss on Facebook. Good luck calling in sick on Monday when she can clearly see your party pictures from the night before!

      1. Anonymosity

        I friend NO ONE from work on Facebook or anywhere else unless one or both of us has left the company. I don’t care if people are butthurt. The only time I ever did was someone at Exjob, and we followed each other on Pinterest. I haven’t heard squat from her since I left, either.

        I don’t typically hang out with coworkers, either. I see them enough at the office, thanks.

        1. RandomusernamebecauseIwasboredwiththelastone

          I don’t even friend people after they’ve left the company. I can’t be sure who they are friends with who still works at my company.

          Coupled with the fact I have the most boring Facebook life ever (seriously it bores me… I always feel sorry for whomever the algorithm sticks me in their feed; pictures of my dog from doggy daycare, football team memes, and pictures of the boat that I go on once a year… the most controversial thing I’ve ever seen in my feed was the great debate on if my hometown had the best tasting municipal drinking water… all participants were from my hometown and they all agreed it was ). There is zero chance that I’ll ever have any FB drama, I think I’m doing Facebook all wrong.

      2. Bea

        Sometimes you’re partying with the boss and they call in too. Just once…and we just decided to start later, after we rehydrated…

    2. Marthooh

      You shouldn’t have to, no, and I agree that making chumminess sound like the modern default is not ideal. It makes things easier, though, to say something like “It’s not you, it’s me” when you have to pull back from a relationship that’s gotten too sticky.

  11. Chaordic One

    I had a friend whose boss always wanted to go shopping with her on Saturday. Apparently her boss used these shopping trips to discuss lots of business things so my friend really felt she had to go. Her boss wasn’t very good at reading memos and I think she (the boss) might have been functionally illiterate. Or maybe just lazy. My friend didn’t keep that job very long because all of the Saturday shopping trips were a big time suck, even if her boss did buy her a few presents along the way.

    In a related thought, I’ve always wondered about the people who play golf with their boss. That seems like of similar and also inappropriate.

  12. Pollygrammer

    Oh God, the personal storytime in meetings. I had a boss just had to share her family stories in unbelievably boring detail. (Easily 15 minutes once just on the firetruck theme of her son’s birthday party, and a full rundown of the various firetruck themed party supplies she had found. The napkins were so cute! She found the paper plates at the party store, but she had to order the paper cups on Amazon!) This was all after the actual work-related topics were exhausted, but we were all still trapped in the conference room. You can really only believably fake a coughing fit and escape to go get water once.

    1. Anon (this time)

      I know waaaaay too much about the counters and floors at my boss’s new house and when they were redone and how and all the hassles of scheduling with the counter and floor guys and how she and her husband disagreed about the floor color and missing her old house and needing the floors done so she can put down her rug so she can properly set up her reading nook.

      Oh, I also know about her tween child’s health problems. Including genital health.

      YUP.

      (Now that I’m writing all this down here and below, maybe this really ISN’T as tenable as I’ve been telling myself…)

  13. AnonFriend

    A very close friend of mine was made my boss at my last company. It was fine and we’re still friends (both of us left the company for unrelated reasons). But I recognize this was a unicorn situation.

    I wasn’t really sure what to do, though. I didn’t want to lose one of my best friends (we were friends before we worked there), but I also wasn’t in a financial position to Nope out to another job. A job also doesn’t seem worth ending/severely limiting a friendship with someone who was my bridesmaid. It’s a tough situation.

    1. Jules the 3rd

      I suspect in that case, it becomes a lot like working with your spouse – behave so that no one knows about the relationship. Don’t talk work outside of work, don’t share stories / pics of anything you did together outside work, that kind of thing.

  14. Dan

    I had a boss who was really tight with a few employees for a while. She was an amazing boss, for the most part, but she definitely had major blind spots about the people she was friends with, to the detriment of the entire team. This boss promoted one of her besties—a narcissist who was brilliant at managing up—then left the company. Afterwards, the narcissist became a total power-hungry monster…who left the company in a huge flame-out about a year and a half later. TL/DR: No, you shouldn’t be BFFs with employees.

    1. Kathleen_A

      That sounds horrible. On the other hand, it could be that this narcissist could have blindsided even someone he wasn’t friends with. In fact, that might even have been easier. You never know.

      So I think you’re rule is definitely a good one, but even if your former boss had followed it. it might not have helped.

  15. Waiting for the Sun

    That first example, with the shared vacations, sounds like a lot of togetherness for a regular friendship, much less a boss/subordinate one. I would want some breathing room.

  16. Jiji the Cat

    I left my old job because my boss was trying to force a friendship. Well, that wasn’t the only reason, but that complete disregard for boundaries only added to the general toxicity of the place. We rarely had employees last a year.

  17. Utoh!

    This is so funny because in my department there is a group of managers and their reports who are constantly sharing clothes and going out, they are all BFFs and it shows in the way that they can socialize all day and no one bats an eye. No one else can do the same in our department because we are the ones doing all the work!

    1. Utoh!

      Actually, one of the women in this group cannot keep anything to herself so I know *all* the gory details about their adventures, whether I want to or not. She even shared with me something that was so incredibly personal about her (and my former) manager so that I have never felt the same way about her since. It’s REALLY not a good idea to get to know your manager at that level if you can’t keep it professional and not overshare. Of course said manager is also an oversharer, but I don’t think she would have mentioned this…unless it’s a case of one-upping someone. So glad I’m not in this clique, I guess that’s the blessing of getting older and not giving a F*. :)

      1. Kathleen_A

        Dang it, now I want to know what she said! Like, *bad*. I get why you’re not saying, and that is actually a very smart move, but I can’t help but be curious.

  18. Laura

    I’m curious what everyone’s opinion is of maintaining a friendship when that friend becomes your boss?

    I worked with Mary (not her real name!) 6 years ago where we were on the same level in frontline hospitality roles, and we were casual friends. Then a couple of years later we both worked at a different hospitality-type location, her as a director of a department, and me as a manager of a third party vendor- we became closer there, basically close confidants. It was nice to have a safe person to vent to because that place was toxic, and I know she felt the same.

    Fast forward to last summer and she contacted me- after having walked out of the aforementioned position due to toxicity, she accepted a high level role at a new company for a new location. She needed supervisors under her, and she contacted me because a) she knows my work ethic and b) she knew I was still stuck in a super toxic place. So I happily accepted.

    We’ve now been working together for almost a year, we’re closer then ever, and I think it’s been working really well. She’s currently being considered for a promotion for a higher level role that doesn’t exist yet, and I am being considered for her role if everything pans out.

    1. MLB

      I think as long as both individuals can maintain a proper working relationship (no favoritism) and not take anything personally when constructive criticism is given, it can work. I commented below about my relationship with my boss. It works because we can be both professional and personal and not let one affect the other.

      1. Laura

        That’s a really good point and hits the nail
        on the head- I’m good at accepting criticism (I welcome it as long as it’s constructive!), and I am also comfortable giving her pushback when I don’t agree with a decision she’s making. We’re really good about talking through issues and pointing out different sides that the other person may not have considered. She has on some occasions graciously changed track on decisions when I point out angles she may not have considered, and when she doesn’t choose to change track, I am always still supportive of her choices because she is good about making sure I understand why she wants to do certain things, even if they aren’t the things I would personally do.

        It’s a really good balance.

    2. Jules the 3rd

      It actually sounds like you have a good professional relationship with your boss, not a personal one. Do you spend time together outside of work, doing non-work things? You don’t mention anything like that here, except the vendor / venting role.

        1. Cat Herder

          That’s the only concern I see — do any of your co-workers know that you are outside-of-work friends? (and are you *sure* about that) If yes, that’s potentially a problem.

    3. Bea

      Everything seems fine. Don’t look for problems where there aren’t any.

      You aren’t feeling pressured to be her friend or making excuses for crappy behaviors etc. It’s all good.

      Just like if you work with a spouse, you need to just have business and private separate. It boils down to individuals.

      For every horror story, I’ve seen a well balanced good team balance.

  19. Anon Today Anon Tomorrow

    The worst job I ever had was due to my boss being BFFs with one of her direct reports. They did go on vacation together. It was horrible, because they were clearly talking about the department in their personal time. They’d leave on vacation, and then come back and institute all sorts of new policies. I didn’t make it a year before I quit. Both them were fired within a year of me leaving.

    1. Lumen

      One of the worst people I ever worked with was given a managerial position and immediately convinced the owners to let her expand her department…and then tried to hire her two best friends.

      Luckily they only let her hire one of them. And he was given preferential treatment, more flexible scheduling, more responsibilities (despite being a lower performer than his teammate).

      And then he quit shortly after she did.

  20. MLB

    While rare, it IS possible to have a real and true friendship with your boss. I have this with my current boss. She was one of my managers at my last job, and we kept in touch after she was laid off, then she reached out to me when my current job was available. She doesn’t treat me differently than others at work, she can provide (and I am receptive to) constructive criticism on the job, we hang out sometimes outside of work (would probably do it more often if our schedules allowed for it) and she and her husband came to my wedding. We don’t share clothes (but I don’t really do that with anyone other than a random jacket or sweatshirt if one of us is cold), but I would go on vacation with her if the opportunity came up.

  21. Jaune Desprez

    I was friends with a boss and it went completely sour. She was in a tough financial situation after an acrimonious divorce, and she suggested that I give up my apartment and pets and rent part of her condo. The worst part was that it was a one-bedroom condo. She wanted me to live in her walk-in bedroom closet.

      1. Jaune Desprez

        Fortunately, I was able to truthfully tell her that giving up my pets for adoption was just never going to happen, and that was sufficient to kill the proposal without getting into the long list of horrible things I would rather do than live in my boss’s bedroom closet.

  22. Anon For This...

    My husband is dealing with a situation right now where an operational change needs to be made for the good of the company, but his boss refuses to greenlight it because it will result in more work for one of her besties that she manages. She has refused to listen to reason, and her solution has been to just repeat “what other options have you thought of?” over and over, when there are literally no other options (besides the one that makes the most sense, which she won’t approve). The impact this is having on my husband, and her lack of advocacy and inability to be objective, it making him hate going to work everyday.

    Managers, do not be besties with your subordinates, please.

  23. Anon attorney

    I think it can work up to a point. I’m friendly with my current boss. We go for lunch occasionally (just a sandwich, not a three martini blowout) and have once it twice gone to the theater together. I’m mindful of the boundaries and don’t drink alcohol on these occasions nor overshare personal information. I don’t think it’s affected work or feedback – I’ve had some very clear constructive feedback and I actually feel confident that my boss won’t hold back from telling me if I need to change something just because we have a friendly relationship. Although writing this has made me realize it is a friendly relationship and not a friendship – and I think that works.

  24. Meredith Brooks

    The person I work for now, might be my best boss ever. She’s supportive, calm in crisis, helpful, and optimistic. But, this issue is one of her problems. She’s a very likeable person and as a result, people enjoy being around her. On the whole, that’s not a problem, but I have a coworker who she’s friendly with. They meet after hours or over weekends. I am the team lead and on some level she reports to me, but we all report to my boss. A couple of weeks ago, my boss tasked with improving colleagues performance (she’s not bad, but could be better). I’m pretty sure I was given the responsibility, because my boss is her friend and can only criticize so much.

  25. Anon (this time)

    Oof, I feel this one.

    My current boss has some boundary blindness. She’s a good manager overall – is accessible to help but doesn’t micromanage, is flexible about appointments and time off, gives good feedback and advocates for her reports. But sometimes…oof.

    Some examples:
    – saying we were basically “the same person”… in my interview
    – inviting me to have a tea party with her and her kids, including tutus (I do not have or want kids of my own)
    – lots of time in check-ins or meetings spent veering into personal topics
    – sending me links to her sister’s blog about ongoing illness
    – telling me about another job she’s interviewing for and when she expects an offer
    – “joking” (not really joking) about how she doesn’t need a therapist, because she has me! (yup)

    At our last company event, her preschool-aged child (who I’d met once, a year prior) wanted to whisper in my ear that he loved me. I like kids, but this kinda made alarm bells go off in my head. A child his age likely wouldn’t even remember me from that long ago unless he was hearing about me regularly.

    On the one hand: I genuinely do like my boss. She’s a good person and a good manager (boundary blindness notwithstanding). I know she’s going through a really rough time in several areas of her life, and I think she has some self-esteem issues*. And I hate to say it (because I really don’t think this is about her being ‘unlikable’) but I don’t think she has many (maybe ‘any’) friends outside of her family members, and doesn’t feel like she’s ‘in’ at work, and just sort of latched on to me based on a preconception of who I am that she formed in the first 30 minutes of talking to me.

    But I only feel comfortable pushing back and setting boundaries to a certain degree, because… she’s my boss. She writes my reviews. She approves my timesheet and PTO. I don’t want to risk offending or angering her (especially when she’s at a higher stress level than usual).

    On the upside: it’s not so bad that I feel unhealthy or unsafe at work. When I’ve sidestepped an invite or told her that no, a therapist can provide a lot more than I can, she hasn’t doubled down. The benefits of having a boss who really likes me currently outweigh the costs, but it’s something I’m almost constantly mindful of – do my coworkers see favoritism? IS there favoritism? Is the boundary between us getting to a danger zone? Etc, etc.

    So yeah. I FELT THIS ONE, Alison.

    *The fact that I even have enough information about her and her life and her family of origin to track her potential emotional state and possible self-esteem issues is, yes, another sign of just how over-sharey this relationship can get. Oof.

  26. A username for this site

    It’s funny, because I went into working as a Super Professional Uptight No Friends At Work All The Boundaries Type, and came out of several experiences of being the boss with the complete opposite opinion.

    I’ve worked with people who clearly had toxic friendships at work, ex: employees who used their friendly status with the boss as an excuse to “get away” with this, bosses who befriended certain employees into an ingroup and turned on those in the outgroup, bosses who gave assignments based on friendship and not merit, bosses who expected lavish gifts from employees and punished those who didn’t partake, etc.

    However, in the years I’ve been working, as a boss, I’ve seen the perils of No Friends at Work. If you, the boss, can’t cultivate (appropriate) friendships with your employees, the little things will turn into big things. People lie about absences, cover up mistakes, withhold information, and silently carry small problems into big, resentful burdens. I’ve had people admit to me much later than necessary that they need accommodations for serious personal issues, that they were performing poorly because of sexual harassment, that their coworker’s violations of safety procedures scared them but they were trying to fix it on their own, that another employee was creating a hostile and toxic environment that made a bunch of people uncomfortable such that they were all looking for other jobs to leave that person, or that someone secretly wanted to pursue a different career direction but was afraid of being a disappointment and therefore didn’t get the correct professional development.

    The things that stay hidden when people are afraid of their boss can be just as bad as the things that are revealed when people have poor boundaries. Finding that sweet spot is so important.

  27. Kittyfish 76

    Wow, so much of the first scenario is like my previous toxic job. Where the BFF coworker was able to act with impunity. So much of that place was oversharing, personal drama. I am sure it continues to this day. I wish while I was there I knew about this blog so I could better prepare myself for all the rampant favoritism, etc. Glad I am gone.

  28. topscallop

    My boss at my last job had poor boundaries and was only a couple of years older than me. She wanted us to be both friends and colleagues, but she also was a micro-manager whose standards were incredibly high and would re-do your work but still praise you as she was doing it. We work in global development and would travel around the world together, but even when we were in the office, she was stunningly codependent. She would send me a chat message every day at lunchtime to go eat together. Other colleagues on our team would beg off, citing too much work, but I felt like I couldn’t since she knew my workload. While traveling we’d spend all day together, then work for a couple more hours to prepare for the next day, then go out and eat dinner. She is an external processor and extrovert; I’m an internal processor and introvert. I was constantly exhausted. I am also a people pleaser and would have had a hard time saying no if she were just a colleague, let alone my supervisor.

    Things came to a head for me when we were at a conference together in Bangkok and it was really tense between us – she didn’t think I had done enough prep for our session (she was right to an extent, I was self-sabotaging out of being at the end of my rope with her- felt like nothing I did was good enough so why even try…unhealthy) and yet had to do everything together. At one point, I caught myself wishing I could get moderately injured, like in a minor traffic accident – not enough to be seriously hurt but enough to go home. That’s when I realized how dysfunctional the relationship was. As soon as I got home I started job hunting. I’ve been in my new job over a year now and am SO MUCH happier now that I am supervised by someone more experienced, older, who lives in a different state and has a weekly touchbase call with me rather than being joined at the hip.

  29. Reads Too Fast

    When first I read this subject, I immediately pictured one of those 2-person sweaters that they usually make for Christmas. I’m not sure if this situation isn’t worse.

  30. Oilpress

    I think you can be work friends with your boss. You can go to lunches, talk about non-work things, and be supportive of each other. Anything much more than that starts to get awkward. Spa trips and vacations are definitely too far.

    The big caveat is maintaining fairness. The boss should not be work friends with one or two people on their team but distant from the rest of the team. If the boss takes one of their team to lunch, they should do the same with others on the team.

  31. Annie Nimity

    I went to work for my best friend of 20+ years at her company. We’d known each other since grade school. At first it was awesome. But as time went by I started to see how she did not treat her staff fairly. She was petty, paranoid and sometimes just downright mean. She would speak ill of employees and clients to me, ridiculing their clothing, hair,, personal lives. I was an employee too…. What was she saying about ME behind my back? I didn’t like some of her policies and began to question her. Some of her business dealings were unethical. The more I questioned and suggested changes and better ways, the more she distanced herself from me. Eventually I was so stressed out about work that I’d almost have a panic attack going in the door. I’d pray that she wouldn’t come to the office, because things were so much better when she wasn’t there to hover or change policies and procedures on a whim. There were several straws that broke the camel’s back, but the last one opened my eyes to finally realize I had to get out. I gave notice and left. She always had talked in the past about how employees who resigned or quit working for her were dead to her. I guess that means me too because she hasn’t spoken or contacted me since. A decades long friendship over…. Just like that. I think what really hurts is that she was like that all along and I just didn’t see it, or want to see it, until it was in my life every day. I thought she was a better person. I was wrong.

  32. Grendel

    I managed a small team and reported to a director who befriended some of my subordinates. It was pretty awkward to have disciplinary-type conversations with an employee, and then see her vacation, concert, and party nights with my boss on Facebook. I ended up leaving that toxic mess of a job. Last I heard, overly-friendly-director started dating one of my (former) team members while he still worked there.

  33. LGC

    *raises hand meekly*

    Yeah, I recognize a lot of my old behavior in this. No vacations, but…what made things awkward in my case was that I got promoted in an office where I’d had a lot of work friendships, and further a few people I knew from outside work (including my best friend) were there.

    I was REALLY popular. I was also a total disaster, as employees were gossiping to me about my coworker (and I…kind of encouraged it), I actually ended up having a public argument with him once, and eventually I was transferred. (To be honest, I probably should have been terminated. They said it wasn’t related to my behavior. I still don’t believe it.) I was actually going to comment about how sometimes, it’s the employee putting the manager in an awkward situation. But…like, obviously I don’t have all the power, but in my case (and being older and wiser) I could have shut down a LOT of the more toxic stuff.

    At the very least, I learned to IMMEDIATELY deflect employees who wanted to be friends after that experience. And it also made me a lot more cautious about my best friend.

  34. Hannah

    My best friend of almost 20 years works for someone who works for me. I abstain from offering an opinion regarding her compensation or potential promotions, or work assignments, or really anything affecting her, but because that fact isn’t publicized, I’m sure the perception isn’t great and it probably harms her relationships with her peers to some extent. I used to work in a different department, so the friendship – which preceded even our history with our current employer – was a non-issue at the time, and as a result many people are aware we are friends. I try hard not to make the relationship obvious at work, and I think most people don’t know the extent of our friendship, even if they know we are friends.

    I cringe all the time reading about friends in managerial relationships, but I’m not really sure how else to address it, since I’m not willing to give up the friend or the job, which seems like the most common suggestions.

  35. All about that action

    I had a boss BFF earlier in my career. It feels so inappropriate looking back. We went to bars all the time and to Vegas. Bonus – we were in HR!!!

  36. many bells down

    Mr. Bells is currently supervising a very close friend of ours. “Dan” joined the company a year and a half ago, and somehow got assigned my husband as his supervisor even though he told them that he was friends with Dan. Like, we officiated Dan’s wedding – that’s how close we are.

    It’s so weird and awkward and I really wish they’d assign Dan to another lead for everyone’s sake.

  37. Persephone Mulberry

    I am tempted to send this article to my boss, as I was just contemplating today how to broach the “I’m old fashioned about work/personal boundaries!” issue. Because…my boss is the sister of one of my very good friends. Neither my boss or I made the connection until after I started, but this afternoon she made a comment about her sister wanting to get us together for drinks and Cards Against Humanity *in front of the rest of the team.* I may have physically recoiled.

  38. AcademiaNut

    One thing I find interesting about the comment sections in articles like this is that you get people with horror stories of being the boss, the employee or the coworker in a BFF with the boss situation, and you get people popping up who say that they’ve been the boss or the employee and it worked just fine. But you rarely, if ever, see people saying “My boss and my coworker are best friends and nobody in the office has any problem with this.”

    In other words, just because someone thinks their close boss/employee friendship is perfectly fine and totally fair, it doesn’t mean that the rest of their coworkers agree. Rather, the cost of speaking up about it to either the boss or their favourite is too high to risk.

  39. Panda Bandit

    I know I’ve mentioned the boss who said we should all go on vacation together! This boss also said that one day we’d all be living together. Thankfully this is my last week there. But boss hasn’t learned anything because they’re already trying to be BFFs with the new hires.

  40. Anon for Besties

    What are best practices if your boss was your friend before she became your boss?

    One of the people I report to is my childhood best friend. She’s like the Gus to my Shawn (except I can hold down a job and am hopefully more mature in general). We both ended up getting jobs in the same company. Then after a little while, Gus got promoted to be part of the team I report to. She’s a great boss, but I know the fact that she’s my BFF is inviting complications (the fact that Gus is my friend outside of work is also something that’s well known).

    1. Anon for Besties

      Somehow I missed the “these dynamics can be especially hard to navigate when you’re friends with a peer and one of you gets promoted” line the first go-round, but my quandary is really more about when you’re extremely close friends before you ever work together.

  41. Bazinga

    This is timely. We are dealing with an overly friendly boss. She is a good person. She’s worked with one of my coworkers for years, since before she was promoted. They’re friends and go away overnight sometimes. I don’t think she plays favorites as I think she treats us all equally well, but sometimes I think she can’t see some of the poor behavior of this coworker. She makes excuses for her and tends to let it go. I think she would do the same for the rest of us but we wouldn’t act like that. It’s very frustrating. She’s someone who likes to see the best in everyone, which is nice, but sometimes at work it isn’t the best way to handle things.

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