can a manager and employee vacation together?

A reader writes:

I am a VP in the finance department. My boss wanted me to hire a person from another department who is my best friend. My boss knows this. She is a great worker. She gets no special privileges. She is treated like all the other staff.

We had planned a vacation before she began to work in my office. We went on the vacation and she returned back to work three days before I did. When I returned, I was told we can not do that again.

There’s no policy that states we can not go on vacation with staff at all. I cross-train everyone in my department so everyone’s desk is always covered for vacation. Is this against any work practice or is this not good, period?

Was your boss saying that you can’t go on vacation at the same time as another employee in your department, or was she saying that you can’t vacation with an employee?

Saying that you can’t go on vacation at the same time as another employee in your department is reasonable if it would leave your department under-staffed, although that should really be something that you — as the department’s manager — would be able to figure out. If your boss thinks it does cause problems and you think it doesn’t, then either your boss is seeing something you don’t see or you may need to explain to her what arrangements you’ve put in place to avoid problems. (Or she may simply feel more strongly about this than you would, which is ultimately her prerogative.)

But if she’s saying that you can’t go on a vacation with an employee, well, that’s not unreasonable either. Yes, I get that this is your best friend, and that relationship existed before you hired her. But now that she’s working for you, the relationship has to change — that’s part of the deal when you hire a friend. You can’t vent to her about work anymore, she can’t tell you that the reason she called in sick yesterday is because she was hungover, you can’t be a nonjudgmental sounding board about work issues, and yes, you can’t vacation together.

Vacationing together creates an appearance of unfair, preferential treatment. Whether or not one really exists, it would be crazy to expect your other employees not to see things that way when you’re vacationing with one staff member. There’s just no way that people aren’t going to see that and assume other forms of favoritism.

So yes, your boss is absolutely right that you can’t do that again.

{ 82 comments… read them below }

  1. Not So NewReader*

    “There’s just no way that people aren’t going to see that and assume other forms of favoritism.”

    Thank you, Alison for saying this so clearly. Having been on both sides of this question- it is true. There does not have to be favoritism going on. All that has to happen is the perception of favoritism.

    This is a big deal. Very, very rarely can a boss be a friend and a boss at the same time. There might be one in a million people who can actually pull off that dual role. It almost never happens because someone, some where will complain about something imagined or real.

    I think OP’s boss gave them a break on this vacation because it was planned before the BF changed departments. Good for the boss.

    1. Poe*

      Agreed. I worked in an office where one of TPTB was close friends with one of my coworkers and they went on several vacations together (before the big-wig got married they both loudly considered themselves Sex and the City singles), including an annual Vegas trip. While there was never any evidence of preferential treatment (except the time I had my request for holiday turned down, possibly to let them take the same week, I swear it was a conspiracy), it bothered a lot of people.

    2. Jessa*

      I agree, I think it’s okay to have gone on the already planned, probably paid for before the transfer happened vacation. It’s just like saying “I have something planned for x time” when starting a new job and working that into the negotiations before you’re hired/transferred. However, the near occasion of sin and all really does mean that it cannot become a regular thing. It just would not look good.

      It’s more than reasonable to say that you should not do that again.

  2. Sourire*

    While I totally agree with Alison, I have to say I really feel for the OP here. It sounds like this hire/transfer was the boss’s idea, and thus OP is now having to deal with a serious change in the relationship with her best friend as a result. If it was OP’s call/choice to hire this person*, that is different, but if not, she ended up stuck between a rock and a hard place (possible insubordination issues depending on just how much the boss wanted to hire this person versus unwanted changes/complications in personal relationships).

    *I am assuming OP did not have a lot of choice/influence over this decision, but if she was the one who recommended her friend, had other candidates she was easily able to choose from, etc, much of my sympathy is lost. In that case, these complication really should have been considered before making the decision.

    1. Ask a Manager* Post author

      I agree with all of this — although I’d also note that even if the boss was insisting on it and the OP couldn’t say no, the friend could have said no. (And if they’re truly best friends, I’d think the OP could have talked to her about why she should.)

      1. Jessa*

        Exactly. At this point I think they have to talk about what it means for the friendship, but they have to understand that it will cause morale problems in the future if they continue to act that close outside of work and the other staff find out about it. And they will.

    2. The IT Manager*

      Me too. Frankly to extrapolate, LW’s best friend really can’t be her best friend any longer without the negative work consequences of the appearance of favoritism. This is the professional reality. This sucks for the LW, but it shouldn’t be a surprise. When best friend accepted the job, the relationship has to change. Accepting the job is deciding to value work advancement over the friendship. Maybe the LW and her best friend didn’t realize it, but that’s what has happened.

      LW, if you want to remain best friends it is time for you to start looking for a new job ASAP before this unprofessional relationship blows up into something that hurts your performance and references. Your boss has already noticed so you need to act fast.

  3. Sydney*

    Alison is right; reasonable employees might see favoritism in this situation, whether it exists or not.

    I could also see this not posing a problem depending on how she reports to you. If you’re a VP, and she’s not your direct report, but only sort of under you with 2+ people in between, I could see this situation being okay in some companies. But that’s only if you’re far enough removed to not be the one in charge of her hiring, firing, promotions, etc.

    1. Anon1*

      I’d say that if the person rolls up to you, it is a problem. Doesn’t matter how many levels exist between you – the employee’s manager is probably well aware they have a friend in high places and common vavcations just magnify the issue . My only exception might be if you are in a matrix reporting structure.

  4. Ann Furthermore*

    No, no, no you cannot vacation with a direct report, no matter what your personal relationship is, if you want the people in your organization to respect you and take you seriously.

    My company is, by and large, a great place to work. People gripe about things but my feeling is that if we weren’t putting up with this company’s big bunch of BS, we’d be putting up with some other company’s big bunch of BS. Nowhere is perfect, and every place has its own quirks and internal workings that you just have to get used to and figure out.

    But one area where my company is much worse than others is its politics, and stuff like this is a big reason why. Yes, politics exist everywhere, but never have I worked someplace where they were *so* blatantly displayed. It’s truly mind-boggling.

    One VP is BFF’s with a director that reports to her, and it’s very well known – hard not to be since they eat lunch together in the cafeteria every day. Quite a few people have had issues with things this particular director has done, but everyone knows it’s no use saying anything since she’s protected at the VP level. The VP gave this director a very prestigious award a couple years ago for work done on a huge, multi-year project, but no mention was made of the thousands of hours worked by the people on the project team that made the project successful. It was assumed that their personal relationship was the driving force behind the award. It’s well known that they vacation together, spend time together on weekends, and so on. It’s because of this relationship that this director has been allowed to bully people and get away with it, or behave extremely unprofessionally and not be called on it. It’s because of this relationship that very good employees have left the company rather than have to continue to deal with this particular director.

    It was a huge mistake for you to hire your best friend to work for you, no matter what your boss wanted you to do. You state that you’re a VP, so it’s safe to assume that you should have the final say in who works in your organization. You are going to have to spend an inordinate amount of time proving to everyone else that your friend is not receiving any special treatment, that she isn’t privy to any confidential information because of your relationship, and that any good assignments she gets are because she was the best person to get them and not because of your friendship. If she’s allowed to take time off during a busy time, people will assume it’s because of your friendship. Any time she calls in sick on a Monday or a Friday people will assume it’s because of your friendship.

    It doesn’t matter if it’s true or not, or how excruciatingly professionally you both behave. People talk. And the talk is never good. It’s just human nature.

    1. Jessa*

      All of this. There is no way this is going to end very well. If there’s any legitimate way to move this person out from under your direct control find it. That or take a giant step back. Because this isn’t going to end well.

  5. Mike C.*

    Let’s make this question a little more interesting:

    What happens if the new direct report is a family member or a spouse? Is it possible for a smaller, family run business to be run fairly when these situations arise?

    Just a random thought I had.

    1. Jessa*

      That’s a different dynamic. A smaller family run business has different issues to deal with and yes a lot of them fail because of those issues. But it’s not the same as a larger company.

      Also some companies have rules about this for just that reason. Good companies usually prohibit spouses/significant others from being in line of report to each other. IE you can be in accounting if your spouse/s.o. is in IT. But you can’t be a web programmer if your spouse is the IT manager.

      I’ve worked in call centres where the rule was that spouses/s.o’s could not work in the same team groups. So you couldn’t be in the groups that reported to the same overall top manager. The place was large enough that they had like four vp style managers. You had to be placed in different vp groups. Just in case one of you got promoted to team lead or group manager or something you could NOT be responsible for the other person’s promotions/discipline.

      In one company they would not hire a spouse s.o. on their phones if the other person was in quality control. But they would hire them in the office/back office staff. But IF you were already employed and then got married, the rule was strictly that you HAD to have the QA manager do your stats. You couldn’t ever touch your spouse/s.o’s stuff.

      1. Elizabeth West*

        This is why I won’t date people at work. I can’t lose a job because of my SO. My earning power isn’t that great. I just cannot afford to take the hit for a relationship that might not even work out.

        1. Poe*

          I have had different dating experiences. I once dated someone who worked in the same department, and it was a mess. We broke up, the girl he dated after me showed up at work to scream at him and me (not sure why, well, she articulated why she was mad at HIM pretty clearly, but my involvement was a bit more obscure. She also threw his stuff in the parking lot and we had to call the police when she started hitting him). So…there was that. At a different job I dated someone who worked in a department about 9 light years away from mine, and it was fine. On one project I had to ask him a few questions to get background on something he worked on in the past, but I told my boss up-front that we had a relationship and it was fine. It was also a friendly break up and we ended up on a project together after the break up and everything was great. We’re still close friends. So…there is no moral to this story. Sometimes it works, sometimes it doesn’t.

    2. Ask a Manager* Post author

      Family businesses often play by different rules, and it’s important for everyone involved to be clear on that (including new employees who aren’t family). Some family businesses are run just like other businesses; if that’s the goal, then no, family members should not supervise other family members. Other family businesses, though, have part of their mission as being to supply work for family members. That’s their prerogative, and that’s when you might see something like this — but in that case, it’s really important to be clear that the goal is different.

      More here:

      1. Chinook*

        I echo what Allison says about small, family run businesses being different. First, everyone is aware if the relationships. Second, all the family members have a (perceived) vested interest in the success of the business. Third, family can be harder on you than any boss. Just think of the expectations a given parent had for you growing up and how, sometimes, they weren’t always aware of how you have changed because they still remember that stupid thing you did when you were 7. Now imagine that is your boss. I love my family but none of us would want to work for mother permanently (during the holiday season, unfortunately, is not a choice if we want to see her, though)

    3. Ruffingit*

      I’m sure there are family businesses somewhere that have been able to operate in a professional manner. Unfortunately, I’ve not seen them myself. I’ve worked for three small family businesses and all of them were totally ridiculous in terms of the family issues being brought into the office, family members being allowed to get away with absolute murder, family members being given jobs they were in no way qualified for and so on.

      1. September*

        This was my experience at a family-run nonprofit. I wasn’t aware that most of the staff was family before I was hired, and many of the family members weren’t qualified for their positions (and were bad managers).

        1. Ask a Manager* Post author

          Ooooh, family-run nonprofit is unacceptable, to me. You want to have a family-run business that isn’t well-managed? Go for it. But to run a nonprofit that way, when you’re taking donations to ostensibly help a cause? I find that corrupt.

          1. September*

            You probably wouldn’t be surprised to hear that they are no longer “in business”, after losing their state contract. Luckily, I was already gone by then.

          2. Ruffingit*

            Agreed. But then again, I’ve worked for non-profits that have taken money to help a cause and completely mismanaged and wasted it.

      2. JustMe*

        From my observation (being non-family in a family business), it’s really hard for outsiders to advance ideas in a family company because you’re always outnumbered (or out-voted) by the family clique. The family clique does things how they want to do–same ideas, same preferential treatment, etc. Nothing ever really changes. So, the company stagnates, and you have to either bite your tongue a lot or get out.

      3. Natalie*

        Admittedly I don’t work there, but as far as I know my brother and step father have managed to keep family stuff out of their business. One key factor, though, is probably the fact that my step father has essentially retired, so they aren’t in the office together every day.

    4. fposte*

      I would always expect favoritism in a family business. I might be pleasantly surprised if there wasn’t any, but I’d expect it.

      1. Ruffingit*

        Yes. There will always be favoritism in family businesses and there will always be people who have jobs there that they are completely and totally unqualified for. I worked for one family business where they let the high school drop out son work in various capacities including HR Manager (again, high school dropout with no experience managing others and no HR knowledge at all) and, shockingly, as the CEO because he asked for the job and wanted it. This was a company bringing in millions a year by the way. You can imagine that the CEO job didn’t last long for this guy. The only person in that family who seemed at all normal was a daughter who had never worked in the business. She married and moved to another country. I always thought she did it to get away from the psycho family.

    5. KellyK*

      It’s possible, but not likely.

      Though, honestly, with a family business, if you’re going to hire family members and not treat them the same as regular employees, it’s better for all concerned for them to report to a family member than a non-family member. You have favoritism either way, but you’re at least not putting a non-relative in the position of “managing” someone who they don’t have any real authority over.

      1. Jessa*

        Thank you. This is the best advice I’ve seen so far. I would love to put this on the desk of half the family business owners I know. Please do not give someone a management position over someone they do not have authority over. In big giant letters.

        Actually I think that goes for any boss. If you’re going to be friendly with someone and take their word or give them all the cushy assignments or whatever, please don’t put them under another supervisor just to have an appearance of being hands off.

  6. Former 7 year old*

    “Vacationing together creates an appearance of unfair, preferential treatment. Whether or not one really exists, it would be crazy to expect your other employees not to see things that way when you’re vacationing with one staff member. There’s just no way that people aren’t going to see that and assume other forms of favoritism.”

    How did I NOT ever see this before?!?!! I worked at a nonprofit as a temp worker, and my dept manager went on a weekend trip with 3 other staff members (who reported to her). That wouldn’t have been an issue except of the 3, one of them was a complete witch to me and my staff and my boss flat out said deal with it and eventually stopped communicating with me til my assignment was over.

    Eesh, the more and more I think about it, the more I realize how unprofessional and messed up some of those people were.

    1. Jessa*

      Because sometimes when you’re right in the middle of the thing, it doesn’t occur to you? Immature people however, are going to be like that anyway. It’s good you got out after the assignment.

      Also the truth is temps tend to get treated awfully a lot of the time. They treat us like disposable tissues like they can walk all over us because we’re “not real employees” which stinks.

      1. Former 7 year old*

        Exactly–I’ve experienced this in my personal and professional life as well that you don’t see a bad situation until you’re far removed from it. In fact, I didn’t even think that they were being unprofessional until I wrote to Alison regarding something related to it and she pointed it out!

        This vacation post just reminded me of yet another incident from that time. I’ve moved on, and like I said below, I made tons of mistakes as well so I wasn’t perfect.
        It does suck how crappy we’re treated.

    2. Girasol*

      When everyone in your environment agrees that YOU are the problem, don’t we all tend to doubt ourselves and think that perhaps we are? Good people listen to manager and peer feedback, after all, and we’re all wired for social correction. Of course you could be right and all of them dysfunctional – it’s not a vote! – but humans are not well wired to see matters in that light.

      1. Former 7 year old*

        You’re right, at the time I thought I was doing EVERYTHING wrong (although in my defense, this was my very first time ever in a “managerial” role and while I feel I was adequate with the work product and I tried my best with clients, I can honestly say that I sucked as a manager–I was too relaxed and let the people who reported to me walk all over me [screaming at me in front of clients, fighting with each other etc])….I still acknowledge my mistakes that I made there but now I see that I wasn’t the only one who was like this–people far more experienced and educated were also behaving unprofessionally…so what was their excuse?

      2. Natalie*

        There have actually been some studies on this. One well-known study took one subject and several planted subjects, who were all asked to determine which line of 4 was longer. The plants all strongly insisted on the incorrect answer, and apparently the subject would often begin to doubt their own answer.

    1. xx*

      I really don’t like when people say things like this.

      People aren’t here to be told that a particular blind spot they have means they’re probably Not Good at their job. How useful is this comment? Are you suggesting she resign? Maybe accept that judgement comes with experience and people make totally cringeworthy mistakes that they regret later, which refines their judgment? I’m sorry, I don’t mean to be rude, I just can not stand this sort of empty speculation.

      1. EM*

        No, of course I’m not suggesting she resign.

        I’m just surprised she had to ask this question in the first place and it just honestly makes me wonder if she didn’t realize this was not such a great thing — what other kinds of decisions she might be making that are not professional/ideal/etc.

        I hope that she seriously considers AAMs response and maybe does some hard thinking.

        **I am assuming this situation is the latter of vacationing together with the employee and not an issue of simply taking a vacation at the same time as the other employee.

      2. Mrs Addams*


        Not to mention the fact that it’s not clear in the OP whether she had any choice in the hiring/transferring of her best friend. If it was OP’s boss who called the shots and OP had no say in the matter, it’s not fair to question OP’s judgement.

    2. Gilbey*

      Agreed. As a VP I would think she would know this type of situation is not ideal. Questioning her boss and asking the question to AAM boggles my mind a little.

      As a regular worker non-mgmt I know that a boss and being best buds with a subordinate can cause a problem.

      OP, if a person reporting to you wanted to hire his/her buddy to work for them how would you feel about as a VP? Would you say no problem or would you question how well that will play out?

      1. Cat*

        I think that what makes this situation a bit different is that it sounds like she didn’t want to hire her bff to work for her. Her boss wanted her to and/or insisted – we don’t know how strongly. Imagine that her boss had pushed for her to hire her husband; nobody would imagine in that scenario that she’d stop having a spousal relationship with him. For her, this might well have seemed the same and I don’t know that I find that unreasonable per se.

        That said, it was still a bad idea and someone should have short-circuited – either the OP by refusing to hire the BFF (if she had that ability) or the BFF by not taking the job. And one of them really needs to be looking for a new job stat (because honestly, a job is not worth losing your best friend over). But I see why this situation seemed different than her hiring her best friend of her own accord, and I see why she was surprised that her manager pushed for the best friend to be hired and just assumed that she’d stop being friends with her without saying anything about that.

      2. Gilbey*

        Agreeing with EM that is…..
        That is what these threads are for. Not be mean but OP did ask and the responses I believe are appropriate. I am not saying she is bad at her job, a bad person, or anything to that nature.

        But she asked a question and just saynig “No not a good idea” and leaving it at that isn’t going to help.

        A lot of people read this blog and if one person, VP, CEO , french fry maker see’s this and says… hhmm.. I was going to hire my friend, or I am going to be hired by my best friend, and then says, well maybe I need to re-think it after reading this, that is why we all give our opinions the way we do.

        And to go with the original statement that EM says, yes VP should know having your best working for you and going on vacation can be a problem.

        1. J*

          “I question your judgment as a VP if you thought this was OK in the first place.”

          And how does EM’s comment help? He’s not providing any suggestions, just straight up condemnation of the letter writer.

          1. Not usually anonymous*

            Thanks xx and J for speaking up!

            I think commenters are harder on managers who write in, even though 99% of managers are themselves subordinates and subject to their bosses.

  7. anonce*

    I’m in a similar situation (minus vacation). I was promoted after 3 years of working at my current job, during which time I became essentially best friends with someone who I now manage. I wasn’t aware of the issue this would become perception wise, and it’s led to my boss, who I work very closely with and who I share a lot of duties with anyway, taking over managing this person. It sucks, and I hate the impact it’s had on my managing credibility generally.

    My friend and I hang out occasionally still and talk almost not at all about work. There was a learning curve with that — particularly, lessons were instantly internalized after her telling me something another employee said about me, and me, after a couple of drinks, telling her something confidential (albeit about someone who was long since terminated). Never again. We’re also both under 25, and while I don’t ever want to rest on that as an excuse for not foreseeing problematic situations, it feels like I’m still learning a lot generally. I would probably not have a friendship like this ever again.

    Last thing to note — I’m working in the hospitality industry in a place where everyone is sleeping with each other, including HR with several employees. The GM here is a very personal friend to a selection of staff, and a lot of people working here are family. Managers get falling over drunk and cry in front of their staff in other departments. In some ways, I think the only reason my one friendship is an issue is because we’re relatively quiet about it compared other folks.

    Not a justification, and this isn’t really a direct response to the OPs situation, but I’d guess this sort of thing changes a lot depending on the industry and company culture. A lot of questions and answers here skew toward a very particular work setting, I think.

  8. AB*

    “She gets no special privileges. She is treated like all the other staff.”

    Just to add to what’s already been said, there are plenty of studies in behavioral economics that show that no matter how unbiased we think we are, humans are not wired to be neutral in situations like this. We will always have a tendency to see our friends / family members we like in a better light, excusing their flaws and augmenting their virtues.

    OP, you may think you are treating everybody equally, but one of two things is likely to happen at some point: the friend gets the best project, with it being rationalized as she being the best person for the job, but with the friendship subconsciously influencing the choice, or the opposite: the friend does not get a project she deserved because the boss is trying to compensate for the bias and prove neutrality to the team.

    There is no win-win in this type of situation.

    1. Anonymous*

      That’s going to happen even with friendships that form at work, though. When you work somewhere, you always grow closer to some people than others, and sometimes they become lifelong friends. The same unconscious behavior is going to happen in that case.

      So if the boss was pushing this hire and knew perfectly well the two were friends, there wasn’t any good reason to not hire the friend. The OP could just as easily have gotten close with the new hire after the fact.

      1. Ask a Manager* Post author

        But a manager needs to be careful not to grow close with a staff member like that; you need to have professional boundaries while someone is working for you. If I saw that someone I managed had developed a close friendship with someone they managed, I’d have concerned about their ability to manage that person well and the appearance of special treatment on the rest of their team — and that would be the case no matter when the friendship started.

        1. AnonEMoose*

          Perceived (or actual) favoritism is incredibly toxic in the workplace, too. This is a bit complicated, but where I work currently, the team I’m on was created a few years ago with “Leila” as our supervisor. She blatantly favored two employees “George” and “Stacy” out of a team of about 15 people. Worse, she equally blatantly “disfavored” one or two other people on the team, leaving the rest of us scrambling to more or less not be noticed.

          Leila was doing things like, pretty much every time I’d speak up in a meeting (regardless of what I said or how I phrased it), I’d hear about it (in a negative way) at my next 1:1 meeting with her. I heard from other employees that Leila was literally crying about her personal problems in her meetings with them.

          Eventually, it was decided by Leila’s boss to split the team into two, with Leila supervising half and Stacy supervising the other half. And guess what? Stacy continued and expanded the blatant favoritism of George and outright bullied two other people on the team (no, I wasn’t one of those bullied, but it was difficult not to catch at least some of the fallout). I survived being supervised by Stacy by using the “smile, nod, do what I’m told and under no circumstances share my real opinion” approach.

          Eventually, Leila moved to another department entirely, leaving Stacy supervising the whole team. They’re both now gone from the company (sometimes layoffs aren’t all bad). But the team is still suffering from some pretty toxic dynamics thanks to the legacy of favoritism. It’s less now, but still there. Thanks to being favored for so long, George has pretty much destroyed any chance of more than a very superficial cordiality with most of the rest of the team. Not just due to being favored, but due to his own smug, arrogant, and interfering behavior, which was enabled due to the favoritism.

          Bottom line, favoritism can have very negative and long-lasting effects on a department or team, whether it’s perceived or actual. It’s never good when part of a team feels that, no matter how hard they work or how much they go out of their way, they’ll never be noticed or thanked, because the boss is spending too much time blowing sunshine up the “favorite’s” behind.

        2. Lily*

          I managed 2 people and Joe was convinced that I favored Jerry when Joe was not performing and Jerry was. So perceived favoritism can be an ego-saving excuse (for Joe). However, I agree that it is still incredibly toxic. Joe left after a lot of drama.

          1. AnonEMoose*

            It was a fairly complicated situation, and I’m being intentionally vague on some details since I don’t know who reads this. I can say that the favoritism was clear to everyone else on the team, so it was definitely more than the perceptions of one or two people.

            There also weren’t any major performance issues with anyone on the team (little stuff like one person being chronically a few minutes late, and some borderline dress code stuff, sure – neither of those is major due to some specifics of the workplace). Those who were the targets of the worst bullying were young, female, and pretty.

            Stacy did sort of try it with me a few times, too (although I don’t fully fit that profile), but I think that was more about her wanting to flex her managerial muscles, so to speak. She had a real need to throw her authority around from time to time. So between the favoritism and the bullying, it was a pretty toxic environment for awhile. It’s slowly getting somewhat better, but the effects are definitely still there.

  9. Anon*

    The OP sounds somewhat disconnected with how other people will percieve this friendship. YOU know you won’t show favoritism and that the boss is the one who brought her here, so they must, too. But they don’t, and the minute something they want goes to her, suspicion will creep in, no matter how professional and decent your other reports are. This person was offered the job because your boss sees that she’s good professionally, and you’re best friends because you think she’s a great person. Why wouldn’t she thrive in this environment? Then your other reports resent her and you both. Unless she plans to be as mediocre as possible, this will probably go poorly. I could see this turning into a situation where it’s either the friendship or the job.

    1. Chinook*

      Anon, you pointed out perfectly how the OP can be legitimately blind-sided by her boss, concern. If she 100% believes she wouldn’t show favouritism (which could go as far as her double checking, in her mind, any praise for BFF or having higher expectations) or if the OP is excellent in compartamentalizing her life to the point that BFF and she only hang out after work hours and don’t mention it at work, then the OP may thought she was handling it well. But, if they vacationed in the same place, then the perception has been created and it is hard to cancel it out.

  10. Anon*

    Good timing, I just came back from a vacation with my boss (and our spouses). I wasn’t sure if the optics would be weird, so it’s interesting to read these comments. I’m his only report, so favoritism’s not an issue, but we weren’t friends before he hired me. He’s only ever been my boss.

    I was going to be low key about the trip, but he went ahead and posted pictures to FB and tagged me for the benefit of our mutual work friends. Another wrinkle – he’s male, I’m female (but our spouses were there!) Now I’m a little worried that this looks bad on us. How bad is this? If it helps, I work for a small branch of a major NGO.

      1. Clever Name*

        It looks fairly bad, honestly. It’s best to avoid even the appearance of any weirdness/wrongdoing, and vacationing with ones boss isn’t typically done.

    1. Jen in RO*

      My boyfriend has a good friend who was his boss at some point and we did vacation together during that time. I have no idea how this was seen by their other coworkers, but I didn’t think it was such a horrible thing!

    2. The IT Manager*

      I think this look pretty bad. Why did you and your boss think this was a good idea? It actually seems a lot worse than the LW’s situation since this vacation was planned WITH YOUR BOSS.

      Frankly just because your his only direct report means nothing. Your work friends all know that you’re such close friends you vacation together. Every raise, award, recommendation, positive thing said about you by him is suspect because you are friends.

      1. Anon*

        Although I wondered if it was weird, it didn’t seem to raise any flags for him at all. Though now that I think about it, he’s at the end of his career and really doesn’t care how he’s perceived. I’m early-mid career, and I do care! Following his lead wasn’t the best move in this case.

        He didn’t get any likes or comments on FB, so I’m going to cross my fingers, hope no one noticed, and be more careful in the future.

  11. MARA*

    Have no personal relationships at work. Your role is to make money for the company. Human interaction impedes this goal. Your ‘best friend’ is the best widget for the job, according to your boss. Cut off all relations immediately.

    1. Treece*

      I’ve always made very good friends at the places I’ve worked. None of those friends were my boss.

      At my current job my boss is friends with my co-worker (known each other for 10 years and hang out with eachother outside of work). It makes for a not-so-fair work environment. But what can I do? I choose to ignore it and do my job as best I can.

    2. Chloe*

      Can’t quite decide if you are being facetious or not. I can’t imagine being a great team member without having any human interaction. But then, I’ve worked with some reasonably non-social people in the past, so maybe some people are just more comfortable operating that way.

      1. Also Kara*

        I can’t tell either. I do make a point to keep personal and professional somewhat separate (one of my colleagues met her husband at work – not where we work – and … let’s just say I have not yet met a man worth breaking my “no dating coworkers” rule. I’m also not FB friends with people I currently work with, on purpose), but the days would be really long if my coworkers and I had no personal interaction. Not talking about vacationing together; just basic water cooler chit-chat, “Hey, did you see Breaking Bad last night?” kind of stuff.

        1. AB*

          There were past discussions about this here in AAM; there’s nothing wrong with being friendly: showing interest for a colleague’s kids, talking about vacation spots with your manager, etc.

          There’s a huge difference though between being “friendly” in an office environment and managing someone with whom you go out to drink together, use each other as a sounding board for work and personal issues, etc. I’ve never seen the latter work well for the reputation of the people involved.

          1. Also Kara*

            Right, I get that. Longtime AAM reader and have commented under several names (was Kara at one point but then stopped commenting as much -new job, less time- and seem to have been replaced by another Kara). And the commenter makes it clear below that she was kidding, although I confess I really couldn’t tell – and I have worked with people who truly don’t want to make small talk. They want to come in, put their heads down, do the work, and leave.

      2. MARA*

        I’m very worried that you thought that was a legitimate comment. Actually the fact that you thought that might have been a legitimate comment on this blog is what I was poking fun at, there should be a limit to the extremes of ‘professionalism.’

          1. MARA*

            I’m arguing that the existence of this problem says bad things about our society. We work to live, not live to work. Saying ‘the relationship must change’ instead of talking about pushing back against the unreasonable demands of the market (and the boss). Yet, managers seem to think you can put people together for 8 hours a day and there will never be any complicating feelings.

            1. Ask a Manager* Post author

              Managers don’t think there will never be any complicating feelings. In fact, that’s the whole point here: There will be, and so when you’re in a position of authority over others, you have to be thoughtful about what you can do to not feed into that and cause problems.

  12. Maggie*

    Thank you for posting this!

    A few months back my manager got married, and invited one of her four direct reports to her wedding. I always thought it was a little strange, and gave me an uneasy feeling. Now I realize that even though weddings and vacations are different that feeling wasn’t completely unwarranted.

    1. Anon for this*

      I’m experiencing a similar situation. Just one of my peers was invited to my boss’s wedding. She’s posted pictures of them together in various social situations, including out on the boss’s boat. And she recently was “promoted” into a newly created position that was never posted and isn’t a direct, obvious promotion (completely different title). She’s a good worker, so it doesn’t really feel like blatant favoritism is at play, but there’s definitely the possibility / appearance of it. Awkward.

      1. Chinook*

        Your situation, Anon For This, highlights the advantages of having one-on-one time with the boss. The peer was probably innocently talking to the boss about an idea for where she would like to go in the company (or maybe not so innocently – she would be the only one who would know). Since she could casually spitball her idea, the boss was able to see her as perfect for the position whereas, if she only had access to boss at work, boss may have thought of other eligible employees.

        DH found this happenning at one office when his boss smoked. Other smokers were able to talk casually with the boss and gained advantages. DH learned, then, to join a buddy who also smoked in the pit and was able to become part of this group without lighting up.

    2. Jen in RO*

      This might be another Europe vs US thing, but here the manager would proudly be offended if not invited. I just came back from the wedding of my team lead (and friend), and many of my coworkers go on regular vacations together. I’ve never seen it as weird – after all we spend more time at work than we do awake at home!

      1. RJ*

        Hi Jen, I think it’s not so much that socializing with coworkers is frowned upon here,as that the power differential and unequal treatment are problematic. If the boss invited all the people at a particular level to the wedding, that seems ok. If or a member of the peer group socializes with only some coworkers, that seems ok, or at least problematic in a different way. But when only one person or a select few out of a larger peer group are invited to a boss’s event, it opens up opportunities for the appearance and the actuality of bias, conscious or unconscious.

        1. Jen in RO*

          I agree – while I think it would be wonderful not to feel like you *have* to invite everyone, my team lead did invite the whole team and it would have been awkward otherwise.

          (And proudly=probably, in my first comment)

  13. Maggie*

    At Old Job I had a manager “Jane” who played favorites. Each morning she walked through our area making sure to greet & visit with the chosen ones. She just passed by the rest of us, not saying a word. At lunch Jane and her pets would sit at a table in the break room, there was a lot of speaking into each others ears & looking around the room while snickering. Jane was a witch with a Capital B. eventually Jane was fired. Never found out why they canned Jane but I was glad she left.

  14. straws*

    Based on the reality of how things work, I agree completely with the advice here. But speaking from an idealistic standpoint… We want adults to be treated like adults. In the ideal world, they’re expected/trusted to do their jobs regardless of the where, why, how, what, and when. Why is who the only part left out of this? Managers are tasked with properly evaluating their employees, regardless of who they are (friend, relation, son of the CEO, daughter of the president). If the reason is preferential treatment, there are plenty of reasons to play favoritism that have nothing to do with relation or friendship. If I’m expected to control every single other reason as part of my job, then why not that one? I’d be hard pressed to choose between quitting my job or firing a top performing employee simply due to an unfortunate reorganization. In cases of specialized roles, it could even be detrimental to the company to lose one of those employees.

  15. straws*

    Oh, and as a disclaimer, yes I am in a position where I manage someone I’m rather close to. I won’t argue that it presents extra challenges, but I do feel that the pros outweigh the cons.

  16. BCW*

    While I agree with Allison on this, the reality sucks. I hate that you can’t do what you want because you have to worry about what people think even if they are wrong. I’ve personally never become great friends with a boss, but if I was, I wouldn’t want to have to walk on eggshells because my co-worker Jane was insecure and thought everything was favoritism. Again, I know favoritism is awful in the workplace, however if its really not there (and I don’t want to hear about the subconscious thing, because that can happen anytime) people perceptions shouldn’t dictate how others live their lives

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