employee is making sexually suggestive remarks — to his boss

A reader writes:

I’m writing on behalf of a friend. (She’s reviewed and approved this submission, by the way.)

My friend was recently promoted from chief accountant at one hotel to assistant director of finance of another hotel managed by her company. She’s been at the new hotel for about a month now, and the A/R manager — who reports to her — has gotten a little too comfortable with her. He’s begun making comments that are becoming increasingly sexual in nature. It began with remarks about how her boyfriend is “so lucky to be with her” and has grown to the level of what she describes as “increasingly explicit double entendres suggestive of S&M.”

Besides the sexual innuendos, she says that he’s an excellent worker — the best on her team — so she wants to give him a chance to change his behavior before reporting it to her manager or HR. To give some context as to why he might be acting less professionally with her than he might under different circumstances, she has a firm but casual management style and can sometimes blur the line between friend and manager. (She was my manager for about two years, so I speak from experience.) Aside from that, both he and her predecessor reported to the director of finance previously, so he’s used to being on somewhat equal footing with the person in her position. They’re also both fairly young: he is 26 and she’s 27. (Again, I’m just putting the behavior into context, not trying to excuse it — it’s clearly disrespectful and inappropriate.)

How can she clearly communicate that the behavior needs to stop?

She manages him and she hasn’t put a stop to this? Between that and your description of her tendency to “blur the line between friend and manager,” I have some worries about how she’s approaching her job as a manager in general. But we’ll get to that in a minute.

She needs to put a stop to this immediately. This would be true even if they were peers, but she’s his boss. She’s responsible for setting and enforcing standards of behavior.

The next time he makes one of these remarks, she needs to immediately say, “That’s not appropriate to say at work. Please don’t talk to me or any other employees like that.” She needs to say it clearly — no watering it down with a smile or a laugh.

If it continues after that, she needs to treat it with escalating seriousness: “Bob, I’ve told you in the past that remarks like that aren’t appropriate at work. I’m not comfortable hearing those comments, and it’s not acceptable to say things like that to others here either.”

(Note, by the way, that she shouldn’t just be shutting him down when it comes to conversations with her; as his manager, it’s her responsibility to tell him that he can’t talk like that with others at work either.)

She should also alert her HR department that she’s had this conversation with him — because it will not go well for her if someone else reports him for harassment and it comes out that his own manager knew about his conversational tendencies all along.

Now, let’s go back to this management style “that can sometimes blur the line between friend and manager.” She needs to stop that too. She isn’t her employees’ friend. She’s just not, no matter how much she might want to think that she is. Friends don’t judge each other’s work, give tough feedback, impose consequences when their work isn’t up to par, make decisions about raises and promotions, and potentially need to lay them off or fire them. (And managers who try to be friends with their staff? It rarely goes well.)

Given that your friend is already not sure how to address inappropriate behavior from someone who reports to her, she’s really got to step back and reassess her management style — and put an end to the friend pretense. That doesn’t mean that she needs to be cold and aloof, but it does mean preserving professional boundaries, being forthright when there’s a problem, and being comfortable with exercising authority.

{ 118 comments… read them below }

  1. Joey*

    A firm, but casual management style? That actually sounds like the really common “no” management style. I always find it interesting how some managers believe they’re good managers or have high expectations merely because someone performs their tasks well (and usually on their own).

    1. Kara*

      Yeah, I was reading this like “‘How can she communicate that the behavior needs to stop?’ … By telling him to stop it.” Sometimes it really is just that simple.

  2. Tank*

    Alison, you’re on point. I would however leave out the ‘at work’ reference in dealing with the sexually tinged comments. He’s likely to read into that to mean she might be interested in him ‘outside of work’ when she might not be, as he’s clearly looking for signs of interest on her part.

  3. Jamie*

    There are some things that make the world stop while we deal with that and this kind of talk at work is among them.

    Seriously, you hear this and immediately it needs to derail anything else going on while you incredulously address the extreme inappropriateness of what you’ve just heard.

    1. KarenT*

      This. I was about to comment on your response, saying that hotels, bars, restaurants are rife with this behaviour (not that it makes it right, but it is harder to change systemic problems). Then I realized she is the assistant director of finance!

      Agree %100 with Jamie. OP, your friend needs to deal with this immediately. She could land in some seriously hot water if she doesn’t.

  4. fposte*

    I’m curious what her response to this behavior has been so far, and why she would expect him to change his behavior if her response hasn’t been to tell him it’s unacceptable.

    (I suppose there’s a slight possibility that she has firmly told him and that he’s continuing, in which case he needs to get an official warning of his risk of termination if he continues and it needs to be shared with HR.)

    1. BCW*

      Thats what I want to know. I feel like there he probably tested the waters once and got a somewhat favorable or positive reaction, so he thought he had the greenlight to continue. Understand, I’m not saying he is right, but its that whole thing where if you think the other person is into it, then you aren’t necessarily harassing them.

      1. twentymilehike*

        I’m curious what her response to this behavior has been so far, and why she would expect him to change his behavior if her response hasn’t been to tell him it’s unacceptable.

        I’m thinking that this probably has something to do with being young and being a woman. I’ve found myself in a similar situation in the past, and in my head I always had perfect responses, but I just couldn’t seem to do anything more than laugh it off or pretend it wasn’t going on. Addressing things head on didn’t come naturally to me (as I’m sure is the case for others), and it took a lot of work to get to a place where when someone makes a super inappropriate comment now, I have no problem looking them in the eye and shutting them down.

        1. Ali Mc*

          I can totally relate to this – however I think as an acting manager you have to speak up, if not for herself, for her staff! That was my issue with this entire discussion – she is not only responsible for her well being but others working around her. argh. Women just shouldn’t have to feel like this in the work place.

        2. Katie*

          Am I the only one tired of seeing this question on here? Seriously, the answer to “I’m receiving unwanted sexual advances from someone, what do I do?” is pretty much always, “Shut it down and leave no room for confusion.” I don’t care whether you are at work or at a bar or anywhere else. If someone is coming on to you and it makes you uncomfortable, the answer is almost always to tell them so. If you have safety concerns, that’s one thing, but if you’re just worried that it might be weird or awkward to reject someone, especially a coworker, it’s only going to make things weirder and more awkward the longer you let it go on. SHUT IT DOWN.

          I’m the same age as the manager in this scenario and a woman, so I get that society encourages women 1) to treat all sexual advances, no matter how unwanted, as flattering so as not to hurt the precious egos of men who deign to find us attractive, and 2) not to rock the boat EVER, but every time someone writes in a question about “this dude at work is hitting on me, and I really don’t like it,” the answer here is always the same: SHUT IT DOWN. And I just have a hard time believing that most of these women don’t already know this is the answer. What else would the response be? “Ignore it and hope it goes away”? That’s not how you should handle anything else as a manager, so why would this be any different?

      2. Lauren*

        “I feel like there he probably tested the waters once and got a somewhat favorable or positive reaction, so he thought he had the greenlight to continue.”

        Um, there is nothing in this post that implies she has encouraged this behaviour. I think it is fair to assume that she was shocked by it and unsure what to do. We aren’t all born managers and if this kind of thing was new to her she may not have known what to say.

        This is probably exacerbated by that fact they used to be on ‘the same level’, and so a fairly innocent comment like ‘you bf is so lucky to be with you’, which, in the right context doesn’t have any creepy undertones, could just elicit an ‘Oh, nice of you to say.’ Now it has escalated, so yes, she needs to tell him to stop with the comments.

        1. Katie*

          Yeah, but the first time it did venture into the creepy zone, she should have put an end to it.

          Someone else here said that for some people, the absence of a no is a yes, and while we can talk all day about how wrong that is–because it is most certainly wrong–the truth is, at work, as a manager, you should never let something you don’t like persist just because it might be uncomfortable to address it.

    2. OP*

      She hasn’t said anything directly about it at this point – my understanding is that it began last week, which is when she mentioned it to me. She’s only been there for about a month now.

      The first time it happened was over the phone (she was working late and he had gone home, but then called about something work-related). At the point where he said something suggestive, she just made up an excuse to get off the phone. I think so far she’s been ignoring it just because she doesn’t know *how* to react.

      As I mentioned in the letter, she was actually my boss for about two years and she was normally great about addressing problems immediately and directly with people on her team. I have little doubt that if someone had ever mentioned having a similar problem, she would’ve been able to give good advice, but it’s a little different when it’s in the moment. I think we’ve all had situations where in theory we’d expect to behave one way, but in reality when that situation or a similar one arises and it’s unexpected, we find that our response falls way below our expectations.

      That said, I think Alison’s advice is on target.

      1. Long Time Admin*

        Not saying “no” is saying “yes” to people like him.

        She will be a much better manager when she learns how to deal with awkward situations. I hope she takes AaM’s advice.

  5. B*

    I am going to be super blunt – she is not ready or mature enough to be a manager. These type of comments are the first thing someone puts a stop to, even if they are not a manager. Perhaps she should take some business management/style classes or read some books on managing people. And especially reading AAM.

    I will give her a very slight benefit of the doubt, that having what seems a meteoric rise to the top at 27, perhaps she never observed/learned how to be a good manager. Even observing bad managers you learn how to be a good one. But that does not excuse not knowing how to stop “double entredess of S&M”, especially in the work place.

    1. Ariancita*

      I agree that these are the types of comments someone puts a stop to immediately, regardless if you’re a manager or peer.

    2. Anon*


      She’s going to have a serious problem if she doesn’t address this now, he does this to someone else and it’s discovered she knew he engaged in this type of behavior and didn’t do anything. In fact, I know of a manager and her subordinate that were both fired when his harassment activities came to light – along with the fact that people reported his behavior to her and she not only didn’t stop it, but she didn’t report it to HR either.

      There has to be more to the story as to why she hasn’t squashed this. And there is no such thing as a firm but casual management style.

        1. Anon*

          It’s someone who wants to have the higher pay scale and do what they know how to do, but not deal with the people part. In which case, find a job where you have a mgmt title, but are an individual contributor. Don’t go into a mgmt position and make people under you miserable. People hate whimpy managers.

        2. fposte*

          I’m guessing it doesn’t mean she’s in khakis when she tells him that that line of conversation is appropriate nowhere at work and needs to stop immediately.

          I do actually understand that it’s hard to move out of your comfort zone, and she’s not exactly a grizzled veteran. But I think she’s prioritizing him not being mad at her over stopping his behavior. That is not the priority her company is paying her to have.

          1. Hooptie*

            “I think she’s prioritizing him not being mad at her over stopping his behavior. ”

            …and you can bet that he knows that.

        3. Jane Doe*

          I think it’s sometimes synonymous with “not a micromanager,” or describes a boss who isn’t interested in enforcing hierarchy in every decision (by soliciting feedback, encouraging employees to come up with alternative suggestions, etc.).

          In practice, I think it often means what Anon said – they’re not really interested or good at managing people (maybe for fear of being disliked) or are not sure when to exercise authority and how much is appropriate. I had a manager who was way more interested in manipulating metrics reports than allocating work appropriately or dealing with bad behavior.

    3. bobM*

      Agree!!! She shouldn’t be in a management position. She should have noted all his remarks and immediately and I mean IMMEDIATELY, reported it to personnel.

      Sorry to say, but she doesn’t have the skills needed to manage people.

      1. Rana*

        Or she does, and she’s not using them.

        One of the most valuable things someone said to me early in my career was to own my authority and not be apologetic about it. It was said in the context of this being particularly important for young women in such positions (which would describe the OP’s friend) but it applies more generally, too.

        For me, it meant acknowledging that however much I might have wanted my students to like me, at the end of the day I was the one with the gradebook, and the authority – and responsibility – to fail them if they didn’t do the work. Perhaps it would help the OP’s friend to remember that while in a non-work situation it may be difficult or dangerous for a young woman to say no, in this situation she’s the one with all the power, not him. He can only pose a problem if she lets him.

        1. fposte*

          I think the authority thing is really relevant here, and I think that the friend and the OP are reinforcing each other’s weakness here. This doesn’t need to be subject to the approval of–well, I’m not sure whose approval is being worried about, really. Ironically, by worrying about doing this wrong she’s doing her job wrong.

  6. some1*

    Actually, I can see how someone can endure comments like this from a co-worker and not put an immediate stop to it. When I was 19, I worked with a guy who I chatted with during down time. Since we were the same age, sometimes we got around to talking about dating in a general sense. (“I went to see that band with this guy Joe I used to date. Joe and I don’t go out anymore because he moved away, blah blah blah”). Then he started making sexual remarks to me, and even asked co-workers to ask me if I would go out with him on his behalf. This went on for weeks before I told my manager what was going on, and she canned him right away. The reason I didn’t go to my boss sooner is that I thought it was partly my fault because I started out talking about dating.

    1. Anon*

      You weren’t in a position of power over him. This guy is not her coworker – he is a subordinate. She is his BOSS. And you had the good sense to put an end to it. You did the right thing.

      1. some1*

        I agree, I was responding to some of the commenters who can’t understand why anyone would put up with this from ANY co-worker.

      2. Ali Mc*

        I agree Anon! that’s what was so crazy about this post. She IS the boss…..I just can’t believe it. If not for yourself, think of others. I’d be curious to know how many of her staff get similar comments

    2. Jamie*

      Oh I think it’s totally understandable to not assess the situation correctly at 19. You’re just figuring out what is and isn’t acceptable in work and the world. I would have been equally unsure back then.

      1. Laura L*

        Agreed. I definitely put up with stuff when I was 19 that I wouldn’t now (not at work, but in social situations). It’s hard to figure out these things.

  7. Just a Reader*

    Wow…I can’t imagine letting this happen more than once, much less enough to have to write in to a blog. This is management 101–I wonder if she’s had any training at all, or if her employer just threw her into the deep end.

    The one thing that wasn’t covered is: does she know, for sure, he’s not already acting this way with others? If other employees perceive her to be friends with this guy, they may be hesitant to complain.

    In my state, managers can be held personally liable for unresolved sexual harassment issues. I wonder if other employees think she is condoning or even contributing to this behavior.

    1. twentymilehike*

      I wonder if she’s had any training at all, or if her employer just threw her into the deep end.

      I think personally that it sounds like she got thrown in the deep end without training. To be that good at your job at that age, I imagine her focus has been getting good at her job, not getting good at managing. She has to learn somehow, and I’m not that much older, but I know that at 27 I was still quite green.

      I second the comments upthread about her taking some additional training, reading some books, and definitely following this blog!

      1. Jamie*

        That’s an interesting question – did any here get management training for their first management position?

        I didn’t. I learned from good managers what to do, from bad managers what not to do and I’ve learned a ton from this blog which I’ve applied…but aside from being told “to hold people accountable you need to put some teeth behind it.” I don’t think I’ve even gotten advice about how to manage.

        I’m sure that’s not uncommon – I think a lot of us were tossed in to sink or swim – but I’d love to know of training that worked well and helped people transition a little more smoothly.

        1. Just a Reader*

          I did. Lots and lots and lots of training during my time as a manager. I was 30 and on the older side for a creative agency, so many of my peers were 3-5 years younger and also new to management. We were trained to within an inch of our lives by both internal and external trainers.

        2. twentymilehike*

          I’m sure that’s not uncommon – I think a lot of us were tossed in to sink or swim – but I’d love to know of training that worked well and helped people transition a little more smoothly

          I’m in complete agreement. I didn’t realize how bad my managers were until I took some business classes with some good professors and did some reading on my own time. I did it personally because I was interested in becoming better, but I honestly didn’t know what I was missing until it hit me in the face. Like we say in motorcycle racing, “everything is fine until it’s not.”

        3. Revanche*

          I did. Once I started getting mgmt-lite responsibilities (ie: informally, the boss just didn’t manage and expected me to run things smoothly without the title), I took certification courses in Supervision and Mgmt. I knew that I’d be aiming for mgmt jobs after that anyway so figured it would do me good to learn formally as well as informally.
          I also remembered all the crappy things my mgrs had done in the past, what they did well (if anything) and added those actions and why they were bad to my learning framework. Then too, I found Alison around the time I started my real mgmt job!

        4. danr*

          Nope, no training for my short management position. Later on I got to see an excellent manager in action (what a difference) My company never had any training. Usually folks moved up in their depts and learned from their bosses. I had to figure it out on my own, and it didn’t go too well. And this was way before AAM.

        5. Arts Nerd*

          I’m a first-time boss with absolutely no training (other than some nightmare managers whose errors I’m trying to avoid.) I’m also still learning how to be assertive and direct in communicating uncomfortable things – in my life, not just at work – which is posing a real challenge in managing, obviously.

          I’m working my way through Alison’s book (https://www.askamanager.org/my-book). Finding it very helpful so far! Anyone know of any other good “Be a Boss 101” resources?

          1. Ask a Manager* Post author

            If you’re in the D.C. area, NYC, or San Francisco, The Management Center does fantastic trainings for managers:

            One of their trainings actually pulls heavily from my book (since my co-author is their founder and CEO). I sat in on one recently and it was like watching the movie version of the book. I loved it.

        6. jubileejones*

          My first time as a manager I had no training. I was young (25 or 26) and had no clue about managing. It didn’t help that I was promoted internally and ended up managing my colleagues/friends. Imagine being thrown into the deep-end of the pool when you don’t know how to swim and you have no floaties. I failed miserably and was the poster child for bad managers.

          A few years later when I was no longer traumatized by the experience, I actually became a good manager by doing the opposite of what I did before (remember the Seinfeld episode where George does the opposite of what he would normally do…that was me!). I also asked for help, did a lot of research on my own and had supportive bosses who wanted me to succeed (again things I didn’t do/have the first time).

      2. Elle*

        While I agree it doesn’t sound like this manager has had much training, I don’t think its not necessarily a direct correlation to age. I have seen a number of people in my profession, accounting, who have no idea how to manage and they are much older than 27. They’ve always been do-er’s and while they were great at the doing, managing is often not something that’s taught in accounting as you’re trying to learn regulations. Certainly not saying that should be an acceptable “defense”, but rather I’m certain that’s fairly common.

        1. twentymilehike*

          I don’t think its not necessarily a direct correlation to age. I have seen a number of people in my profession, accounting, who have no idea how to manage and they are much older than 27.

          True … but at 27 she’s had a lot less time to learn than someone who is 37, so I’d like to be able to give her the benefit of the doubt and say that its entirely possible that in time she’ll improve, rather than just continue to be oblivous (like so many managers end up doing… ).

          1. Jamie*

            Oh for sure. And it’s not just age but time in management.

            I’m a little older than 27 (ahem) and I’m not the same manager I was even 3 years ago.

            Even those of us who started in the work force older it can take a little while to find your footing and get comfortable with your own authority in a work environment.

  8. Sandrine*

    I actually am very very sad over the fact that we have now come to a point where a boss couldn’t be friends with an employee.

    My boss is sortof blurring the line on this too, but the difference is (and yes there are innuendos from all sides from time to time, like when another team leader asked him to readjust a poster on the wall because she wanted to see the shape of his butt… he never noticed but yes I giggled) that if he needs to kick my butt on something ? He sure as heck does so. In fact, I have told him, repeatedly, that while I wish to be friendlier because I find that (after all) he’s not such a bad human being and he’s pretty likeable, PLEASE DO NOT HESITATE TO MANAGE ME.

    And because of that attitude I have, things are going smoothly. I know what goals I have, he knows my strong points and weaknesses, he knows I’m not a quitter and I know he’s not just a jerk. Just a little too “corporate minded” , in a way.

    So I can totally see myself (and yes, I really do) having a party at a friend’s house who’s actually my boss and getting my behind kicked Monday morning because I messed up a client’s file and if I need to get fired over it, well, procedure is procedure.

    Not that I have zero self esteem but just I’m just a people magnet in that I can get along with pretty much anyone, and I would be depressed to know that there are such barriers (Boss is only 4 years older, too) .

    Now I’m pretty sure I could get used to a US work environment (not like, but get used to) and behave, but, well, it’s rather sad :( .

    I do understand Alison’s logic, though, and given the context, I actually agree entirely with her response.

    1. Ask a Manager* Post author

      It’s not that we’ve now come to the point where managers can’t be friends with employees — that’s always been the case, with some very, very rare exceptions. You and your boss might be one of those exceptions, but typically when you have a power dynamic like that in a relationship, you can be warm and friendly, but not friends. Certainly not in the sense that people normally mean it in.

      And that’s for the reasons I wrote in the post — your boss needs to be able to objectively evaluate your performance, fire you if needed, keep information from you that you might have a huge impact on your if she’s not permitted to share it yet, etc. Most people can’t and wouldn’t want to do that with friends. (Plus, other people managed by your boss need to believe that she’s objective about you, and even if she is, appearances to the contrary matter.)

      1. Revanche*

        Yes, and to put another complexion on it: when bosses INSIST on the managers=friends/friendly = you *must* be their friends, otherwise you’re the enemy which translates into being a “bad” employee based on Not Performance.

        I’ve had some terrible experiences with managers who wanted to maintain a “friendly and casual” style and imposed that on their reports. A) if you weren’t their best buddy, agreeing with everything they said work-related or not, then they took it personally and you were targeted for negative remarks, gossip, and other unprofessional schoolground behaviors. B) You were literally expected to mindread. I was told once “You’re supposed to be my deputy and you should know what’s expected in that position.” We didn’t HAVE a deputy role, and I had no clue when I’d been “promoted” into this non-existent role either. But I was punished for “lack of performance” anyway.

        As a manager, I insisted on maintaining a professional distance (I didn’t try to party with them, I didn’t insist they had to include me in all their group lunches, I didn’t insist that they tell me everything about their personal lives) but that didn’t mean I didn’t care or “take care” of them.

        They were able to tell me when personal or professional crises came up if they needed support, they knew that I would support them professionally in whatever way they needed, and they knew what their professional expectations were. And that I would be straight with them no matter what. And we did share fun events but never from a “you must do this and hang out with me, be my FRIEND” standpoint. (a la Liz Lemon…)
        I definitely wasn’t perfect but this was one of the reasons my staff did work well.

      2. Sandrine*

        The thing is, to me, there are different kinds of friends anyway: some friends I could go to hell and back for, some I might have for dinner at my place, some I might go on a trip with, some I might only have a coffee with, different people different levels, I guess.

        Maybe that’s just me then. In my mind, I can have different relationships with the same person, and I can also adapt to various people in bizarre ways at times.

        I do believe that there are situations where what you say happens (after all, you’re AAM, I’m not :P) but as I said, I’m fortunately confident enough in my abilities to make the whole thing work mostly because of the reasons previously stated… that’s where the “it makes me sad” part comes in :) . It makes me sad to know that something that is so natural to me isn’t natural to others, and I’m thinking maybe if there was a teeny tiny bit more friendship all over the office then maybe things would be less tense in general…

        Wait no that can’t happen otherwise there wouldn’t be so many questions here! Woops XD !

        (I’ve read the replies and as always I really appreciate all the insight. Sometimes I think I’m an alien in the professional world. I might even be staying at my job for a while. I had a “Come to Deity” moment after Jan 1st and I’m almost starting to like it o_O)

    2. ITwannabe*

      Long time reader, first time commenter…..

      Sandrine, in my opinion, blurring the line between manager and employee rarely works – the reason being that the manager stands to lose objectivity and the employee loses perspective. This is not to say that you can’t have a good working relationship – I have been fortunate to have one with nearly all of my bosses. But ‘friendly’ does not equate with ‘familiar’. And really, it shouldn’t. Because if a situation comes up where discipline is necessary, it will be more painful and complicated than it needs to be.

      To OP – I agree with the rest of the commenters. Your friend is putting herself at risk by not taking a hard line. I hope she will find the strength to do it – now. Best of luck.

      1. Jamie*

        Awww- your screen name makes me smile. A wise comment from someone with an appreciation for the wonders of IT…I hope it’s the first of many comments. :)

        But I do agree that there is a difference between friends and friendly. I absolutely have friendly relationships with my bosses over the years – some joking, being happy for them good things happen, being genuinely compassionate when they have losses, enjoying their company…etc. I think that’s great and a pretty ideal relationship to have with someone with whom you work.

        But being friends is different. That’s personal. That’s knowing all the crappy stuff you keep in your psyche and loving you anyway, being there to convince you that you’ll feel better if you take a shower and eat something for God sakes when you lose a parent, that’s hating all the people you hate even though they have never met them.

        There’s a “got your back” quality of a real friendship that just can’t be there in a good boss-employee relationship.

        Because in a good boss-employee relationship the business needs will always come first and both parties respect and understand that.

        The only time I can see friends working in a boss-employee relationship is if the business needs or feedback never conflict with the relationship – because the second you have to make a choice between being there for your friend or doing your job you’re a buddy or a boss – you can’t be both.

        1. ITwannabe*

          Thank you, Jamie, for the kind words and welcome. I am finishing a degree in IT next year and starting grad school. I have enjoyed every bit of it so far!

          1. Jamie*

            Shhhh! If people discover that IT is the most fun you can have at work (with the coolest gear) than they are all going to be switching career tracks and gunning for our jobs.

            Seriously…IT is nothing but stress and loneliness…nothing to see here, people…nothing to see…

            (but just between us – excellent choice! I’ll buy you a virtual drink the first time and end user makes you cry.)

        2. Elizabeth West*

          I agree with this. I had a friend who became my boss and it pretty much ruined the friendship for a long while, because I had to be fired. I didn’t have a problem being fired–in fact I was pretty unhappy and ill at the time, but it made me sad that I lost my friend.

          We’re talking again but we don’t hang out the way we used to. Of course, she has grandkids now and that takes up a lot of her time.

    3. Jen in RO*

      This is one of the reasons I decided management wasn’t for me. I wouldn’t like to get a promotion and lose my work friends… and I sure as hell couldn’t tell someone they aren’t performing well enough. Managing would stress me out so much. My best work friend was recently promoted (she isn’t our boss and we report to the same person, but she has a say in big boss’s decisions), and I hope we get to *stay* work friends!

    4. Anonymous*

      Here’s part of the problem though. Maybe you are perfect. You and your boss are completely and totally perfect in your balance. But lets say you and I make widgets. I make 100 widgets a day. You make 90. The goal is 80 so we are both great. But I see you getting to make the more exciting widgets now because you and the boss are friends and he sees your name and mine on the good performers list and he goes, yeah but I’d rather train my friend to do this cool widget work. The perception that I’m punished for not being friends with the boss by having to make boring widgets is real.

    5. AdAgencyChick*

      I too know that it can work — which is not to say that I don’t understand how rarely it does work. (Kind of like marrying your high school sweetheart IMO!) My current manager, who has been my former manager at 3 different companies now, was an attendant in my wedding party, I love him that much.

      Could he fire me? I mean, I don’t give him cause, so I don’t think about that too much. Can he manage me? Yes. He’s not afraid to tell me what I need to do to improve my work product and how I’m perceived in the office. Can he keep secrets from me? Also yes — he has no problem telling me “I’m not allowed to tell you the answer to that.”

      That being said, although our friendship means that we sometimes talk about stuff you wouldn’t normally discuss with your boss, he never says anything to me that could be construed as sexual harassment, and vice versa. I also know that, although he wouldn’t lie to me or try to screw me over, that he won’t sacrifice his or the company’s well being for mine, and vice versa.

      I recognize that this is a rare and special working relationship!

      1. Elizabeth West*

        I had a bit like this with my last supervisor (a lady also). We are still friends, although we don’t see each other much because we don’t actually live in the same town. I would definitely invite her to my (hope) wedding, though. I’m pretty sure if she were able to that she would come.

  9. Lisa*

    The second that another comment is made, pull your employee aside or into your office (basically away from other’s hearing).

    Joe, Stop. Stop now. You will not make inappropriate comments to me any longer. I am your boss, you report to me, and you will stop making sexually explicit comments to me NOW. Consider this your first and only warning. Do it again, even once, and I will report it HR and create a paper trail that may result in disciplinary action that could cost you your job. Do you understand what I am telling you?

    Avoid trying to explain away your style, “I know I am usually easy going, etc”. No keep it to , stop , stop now, and explain the consequences. Don’t forget to ask him if he understands what you just said.

    1. iseeshiny*

      I don’t know that this is the approach I would use. I would be more likely to say, “That’s inappropriate for this office,” one time, in front of everyone. I don’t think he needs to stop making inappropriate comments to her because he’s her boss; he needs to stop making them to anyone at work, period.

      1. iseeshiny*

        Um. By “in front of everyone,” I mean right when it happens, in front of whoever is there. Not drag him out in front of everyone or what have you.

      2. Just a Reader*

        I agree with this. The power card actually undermines the message of the inappropriate behavior and may convey that this is okay with peers.

      3. Jamie*

        I agree – because you don’t want him thinking it’s a boss-employee thing…it’s just a workplace thing.

      4. fposte*

        I agree that if it’s in front of people it’s useful to make the point publicly that this isn’t appropriate.

        However, if you can’t pull yourself together fast enough to do it then, it’s imperative to talk to him afterwards at this point rather than wait for another occurrence. I suspect the latter is how she’s ended up in the situation in the first place.

        1. Jamie*

          It might help to think of it as the immediate affront that it is.

          If you stomped on my toe I wouldn’t wait and maybe see if you did it again, or talk to you later to ask you not to step on my toe. I’d say “OW!!” right then and look injured until you said you were sorry.

          This is one of those toe stomping problems.

  10. twentymilehike*

    I actually am very very sad over the fact that we have now come to a point where a boss couldn’t be friends with an employee.

    I hear where you are coming from, and agree to some extent. My current boss has even held my hair out of the toilet while I puked before, but it’s not quite the same as my BFF doing it. I like to think of that relationship as sort of like a dating relationship (we use that analogy a lot, don’t we!?)–some exes I’m still able to be frends with and other’s I’m not. Everyone is a little bit different and you have to judge each situation individually. Even if the OPs friend WAS attracted to this guy and ENJOYED the little comments, she should be able to address that it is not approriate with him and they need to keep it professional. As someone who regularly sees boobs at work (on models and advertisements and whatnot), it is smart and important to know where to draw the line.

    1. some1*

      From a different perspective, even if everything is fine between the employee and boss who are friends (as in, no discipline issues, etc), you risk lowering the morale of the other people managed by that boss.

      Several years ago I had a boss who was hired from another dept. New boss was already friends with my co-worker for many years and openly favored her until Boss’s first evaluation from her other employees, when her boss put a stop to it. They also went out to lunch together on a regular basis (just the two of them). Granted, I didn’t want to have lunch with either one, anyway, it was the principle of how it looked that the rest of us were excluded. It also probably wasn’t fun for my co-worker that she was seen as the Teacher’s Pet all of the sudden.

      1. twentymilehike*

        you risk lowering the morale of the other people managed by that boss

        Granted, I didn’t want to have lunch with either one, anyway, it was the principle of how it looked that the rest of us were excluded.

        Excellent point. And very true. That same thing has happened in my workplace.

    2. BCW*

      I think the problem is often other people, not the manager or subordinate, are a bit too sensitive for it to really work. I’ve had bosses before who were friends (would hang outside of work regularly) and honestly to me, it didn’t make a damn bit of difference. I respected that my manager know what they were doing and could deal with problems that came up. I got along fine with my manager, and I’m the type of person who thinks if its not really affecting me, I don’t feel the need to concern myself with it. Other people though felt left out/neglected/slighted whatever. So while the manager/subordinate may have had a perfect working relationship other people’s insecurities got in the way because of a perceived wrong (Even if there wasn’t really one)

      1. Sandrine*

        Just replying here because of the reference: actually, I’ve noticed something that may be a reason as to why things won’t work.

        Usually it happens when people come to a job in “direct opposition” with the bosses/authority. When everything is questioned/analyzed to the point where they come to almost hate the boss. In fact, in my team, this has happened to the point where two people abandoned their job, and at least two others are begging to leave the team (once the team shuffle happens).

        At a time I was even saying bad things about him with another coworker. And for some reason, we both looked at each other one day, said “Screw this”, talked to him (she did it first and is so confident and strong minded that she kinda scared him for a bit I think) and explained a few things, and now we’re all good.

        Thanks to her, I realized that thankfully the French system made it so I could simply go to him, sit down, have a little frank talk saying that I had no idea what he thought of me, but here’s what I thought, blah de blah, things were cleared up and now everything is fine. Just like sisters bickering, it was resolved in a nice way. In the US, because of how easy it looks like to fire someone, I guess people would be much more careful, which might explain the slight difference maybe.

        With that said, there are plenty of bosses I wouldn’t even dream to be friends with. Because they are plenty of jerks out there :P . I like to question my perception of bosses from time to time and while this one could, in fact, become a friend, he’s one of the rare few I’ve had over ten years that I could potentially add to my “real life friends list” .

  11. Not So NewReader*

    Unfortunately, drawing the line is not a skill/knowledge we are born with. It is something we learn.

    Frankly, I see very little training going on out there that shows people where to draw the lines. Yes, there is sexual harassment training but I think that if you have to pull out that information the situation is extreme already.

    Personally, when I was younger, I would have appreciated information on early signs and what to say.
    The first thing I learned was if you see something three times that means you have a pattern and it needs to be addressed.

    I moved on from that to more clearly defining what types of convos I just don’t want to have. For example: I have no issue with medical problems that are spoken of in a respectful manner. I have had a male boss ask me to speak to a woman regarding a female problem. (Basically, the boss needed a time line of some type- but he sent me out of respect for her.)
    I do have a problem with medical stories that are disrespectful, crass and so on.

    I have managed gain the presence of mind to respond on the *first* incident. (This took some doing.) And I developed a short list of one liners that gets my point across.
    For a first offense something as simple as “Hey, don’t GO there!” will stop it cold. Or “moving RIGHT along…”.
    It’s the lack of interest in following that train of thought that comes across. And the quickness of my response seems to help, too. Most of the time it works for me.

    However, if that does not work- a short, clipped statement will work sometimes. “Ok, you are over the line. That is enough of that.”

    Boundaries are not just for sexual/intimate topics. My guess would be, OP, if your friend is having trouble setting boundaries in this arena then there are other topics that she has boundary problems with, too. Not everyone wants to hear about the latest argument with the BF/hubby/SO.

    My experience has been- yeah, you can make a friend out of your boss and that will work well for a while. When it ends- it’s a crash landing. My motto is you want to be a good friend to me- then JUST be a good boss. Tell me what I need to know so I can keep food on my table and a roof over my head. In return, you will have my life-long respect.

  12. Joanne*

    Before I write this, I feel like I need to admit that I have never managed anyone. There.

    If someone at my work were making S&M type remarks, even as “subtly” as through double entendres, I would feel unsafe. For some reason, to me that comes with the connotation that “no means yes, and 50 shades of grey tells me exactly how many yesses, so don’t even bother telling me to stop, because I can read your mind”. If that were true, would that change the way this situation should be handled, or would assertively communicating expectations still be the best route to go?

    1. Ask a Manager* Post author

      Assertively telling the person to stop is the way to go. If the person then continues, it needs to be dealt with as a disciplinary issue, up to and including firing the person. You can’t be held hostage to the worry that the person will think “no means yes” — especially as a manager, where you have a legal obligation to act on harassment concerns.

    2. KellyK*

      I don’t think it changes the response any, and I think it’s a fairly big leap to go from “makes inappropriate jokes about S&M” to “thinks (or pretends) that ‘no’ means ‘yes.'”

      For me, the only thing it would change is that if the guy were giving me creepy vibes, I might take extra personal safety precautions *in addition* to dealing with it as a disciplinary issue. (I don’t know that the specific comments would make me feel unsafe, but this is how I’d react *if* they did.)

      That is, the idea that he might go from stupid jokes to stalking or harassment or threats would be more at the forefront of my mind, and I’d be likely to avoid, say, him and me being the last two people in the building, at least until I saw that he could deal with the discipline like a grown-up and stop being creepy.

      I don’t think the fact that they were S&M comments makes it super-likely that there’s a safety concern. I think it’s more likely that he’s just trying to get a reaction.

  13. OP*

    Wow, I’m surprised by a lot of the assumptions that people are making. Granted, maybe I’m biased because this is a friend, but I think a lot of commenters are being a bit more harsh than necessary.

    1) This is not something that has been going on for a long time. She’s only been at that hotel for about a month now. The inappropriate comments started last week. She called me as soon as the first one happened looking for advice on how to handle it. She had been working late and he had called about something work-related and somehow the conversation devolved into him making an inappropriate comment. As soon as he said it, she made up an excuse, ended the conversation, and called someone to figure out how to respond appropriately. She knew she hadn’t handled it well and wanted to find out how to handle it better if it happened again. I said I would write in to AAM and here we are today. It’s not something that’s been happening for weeks or months that she just hasn’t dealt with.
    And as I mentioned in the letter, he’s not saying explicitly sexual things. He’s making double entendres. It’s very easy for him to defend himself by saying that he didn’t meant it in a sexual way at all, but she took it the wrong way. That’s a little less easy to deal with than an explicitly sexual comment.

    2) I’m a little shocked to hear so many people declaring that she’s a terrible, horrible manager. She’s not. I worked for her for two years and thought she was great. Does that mean that I never got disciplined? Not even close. Does it mean that I never got a fair performance review? Not at all. She’s not the type of person to worry about whether people will dislike her for being honest. She doesn’t pull punches among her friends and she doesn’t go into the office and start pulling punches there, either. Is she a perfect manager? No. Are there problems with a management style that gets too casual? Absolutely. Honestly, I’ve read plenty of AAM posts on why managing friends/spouses/relatives/etc. is dangerous. This may sound hollow as someone who is a friend and a former subordinate of hers, but I think she is one of those rare people who can do her job as a manager well even when her direct reports are friends. I think the danger for her is that the friends/spouses/relatives/etc. don’t always know how to manage their own behavior differently. This situation is a case in point. You wouldn’t normally make comments like that to your boss, but you might make them to a friend you’re interested in (not that it’s the best way to go about it, but that’s a different conversation). And lots of commenters have made great points about why it’s safer to keep the professional/personal boundaries clear. I totally agree. But it’s not like she’s 57, about to retire, and refusing to change; she’s young and she’s learning. Here we have a situation where she gets to do that. Let’s all calm down and give everyone in the situation the benefit of the doubt.

    1. fposte*

      “It’s very easy for him to defend himself by saying that he didn’t meant it in a sexual way at all, but she took it the wrong way. That’s a little less easy to deal with than an explicitly sexual comment.” It’s really not, though. This isn’t a trial where gets to state his side and she needs to be able to prove her case to a jury. She gets to tell him that it doesn’t matter how he meant that comment, it was employed inappropriately for a workplace and it can’t happen again. She should not let herself be dragged into an examination of the minutiae and where she stands on them, and she should add that references to her personal life are now off limits as well.

      1. OP*

        When I made that remark, I was imagining about a hypothetical situation in which HR was involved, which I would assume would be somewhat like having to prove her case to a jury. I realize I didn’t state that quite clearly, but it made sense in my head.

        I do agree that after this she’s going to have to make a super clear boundary with this guy which would include no more references to her personal life.

        Clearer boundaries with her other employees would probably be helpful too, just because it gets messy. But this one has already danced across the line and now needs to stand farther away from it.

        1. Ask a Manager* Post author

          Just to be clear, HR will not require her to prove her case like in a courtroom. And she doesn’t need to go there as his adversary. She can go to them and say, “He’s made these comments, I found them inappropriate, I told him it needs to stop, and while I expect that it will indeed stop, I figured it’s something you’d want to be aware of.”

          That’s it.

    2. businesslady*

      to point #2, I’ll say this–a few years ago, I was about to start working directly under someone who’d been a casual friend for a couple years (& who was really tight with a very close friend of mine, further short-circuiting the usual workplace boundaries). my dad gave me some great words of wisdom: “I’ve had friends become bosses many times during my career. as the employee, I’ve always considered it my responsibility to ensure that they never had to choose between the friendship & their professional responsibilities.”

      I took that to heart, & now (after another role shift) I no longer report to her–but we’ve remained friends, & in fact grew even closer while working together. & I think that’s largely because, while I was her employee, I took care to never take advantage of our friendship, never put her in an awkward position by behaving inappropriately, & never make things uncomfortable for our mutual friend.

      I do think that it IS possible to have a friendly relationship with a subordinate, but that’s the subordinate’s privilege to lose–& a good manager will choose professionalism over friendship if their employee forces the issue.

    3. LCL*

      There are a few responses if the remarks occur by phone. These may not work, she might have to go to HR anyway, and she should be careful to not join in the joking. Anyway, when presented with some possibly ambiguous remark, she could chose one of the following replies:

      “I don’t understand. What do you mean?”
      “I’m sorry, I didn’t hear you. Please repeat what you just said.”
      “I must have misheard what you said. Did you just say XXX?”‘
      “Aw, I am not following you at all. I will talk this over with the crew tomorrow and see what they think.”

      Or, if it is really blatant,
      “I am way too busy to talk to HR today/Don’t want to talk to HR. Could you rephrase that so I don’t have to?”

      1. iseeshiny*

        I love this approach. Either he commits to the yuck or he backs away from it with your point taken. If it’s the latter, fine. If it’s the former, you can address it and he can’t hide behind plausible deniability.

      2. OP*

        I love the last one, even if it’s not blatant. It’s also something that I could definitely picture her saying.

      3. Long Time Admin*

        “I am way too busy to talk to HR today/Don’t want to talk to HR. Could you rephrase that so I don’t have to?”

        That reminds me of Provenza telling a suspect that he’s too old to chase him, and he doesn’t want to shoot him because then he’ll have to deal with all the paperwork, so the suspect should just stand still while he gets the cuffs out.

        And sometimes, you have to…

    4. Jamie*

      But it’s not like she’s 57, about to retire, and refusing to change; she’s young and she’s learning

      The thing is we learn a lot of stuff on the job, but this is so clear cut and harassment such an integral part of management that the “just learning” doesn’t really cut it here.

      A head lifeguard may have to learn stuff on the job like where to put the towels or how to make out the schedule – but she sure as hell better come into it knowing how to swim.

  14. Mike C.*

    There’s one part of the letter that is really bugging the heck out of me:

    Besides the sexual innuendos, she says that he’s an excellent worker — the best on her team — so she wants to give him a chance to change his behavior before reporting it to her manager or HR.

    This is a terrible, terrible philosophy to have. I get that for top performers, things like dress code or attendance might be ignored, and for good reason. It makes sense, because those sorts of infractions aren’t harmful if the employee is otherwise doing well.

    But when we’re talking about things that are crimes, or close to them, performance doesn’t and shouldn’t matter. Doubling my sales in 2012 doesn’t entitle me to take a swing at that coworker I hate, nor does landing that huge contract allow me to get away with groping that cute receptionist a few times.

    This employee has crossed through a DMZ and over a huge, red line. Give them one chance if you must, but after that have them fired. No “hints”, no “assigning everyone sexual harassment training and hope the jerk gets the hint” (because he’ll think it applies to everyone but himself) and no compromising.

    By allowing this sort of thing to happen, the manager is giving him and others permission to continue on, and do it to others. It’s not your fault that this is happening, but proper action will keep it from continuing.

    1. Ask a Manager* Post author

      This is a great point. OP, can you point out to your friend that she (hopefully) would never tell someone else to put up with sexual harassment because the harasser was a top performer? Certain things are not okay, no matter how great the rest of someone’s performance — embezzlement, harassment, etc.

      And she might feel that she doesn’t really mind putting up with it, if that lets her avoid the discomfort of dealing with that, but as a manager she doesn’t have that option. She’s obligated to deal with it, and report it too.

    2. Joey*

      That’s a really noble view, but it lacks all sense of reality. And, we’re nowhere near illegal sexual harassment. We’re talking about a few inappropriate sexual comments that at most violate a company policy at this point.

      We all know that performance and ROI are criteria that are factors in every employment decision. If this person were a poor performer it’s a quick excuse to can him. But if he’s someone that is hard to replace and is worth a lot its harder justify bringing down the hammer down on him is the best business decision. I know that’s not fair, but its reality. Frequently dealing with the headaches is a sacrifice that’s better for the business than the alternative. It’s when the pendulum swings the other way do you change your position.

      1. Ask a Manager* Post author

        I don’t think anyone is arguing for firing this guy at this point — just for making it clear that it needs to stop and for getting HR in the loop (so they’re aware of it in case they get other reports). But if he’s warned to stop and doesn’t stop, that would be a bigger deal.

      2. Mike C.*

        Don’t call me naive, and don’t confuse an argument for “what aught to be” with an argument about “what currently is”. I made the former, you responded to the latter.

        Just because some companies out there are more than happy to justify terrible, unethical or borderline/outright illegal behavior doesn’t mean I’m wrong to call out this behavior, identify it as such and shame those who partake in it, excuse it or idly sit by while it goes on.

        1. Joey*

          Yes I agree theoretically your advice is the noble path, but realistically its not. That’s all I’m saying.

            1. Anon*

              All they’re saying is that something needs to be said. That doesn’t mean firing. Besides, in this economy, when they can choose from loads of qualified people (even in some specialized fields), that isn’t even a reality most of the time.

          1. Laura L*

            I get what you’re saying, but that’s something that needs to change. People should not be allowed to get away with sexual harassment and other bad behavior (particularly behavior that targets historically marginalized groups) just because they are a good performer.

            It needs to start somewhere.

            Although, yeah, no one is suggesting firing the guy for the situation as it stands.

      3. Elizabeth*

        What if it were an email that had an inappropriate joke attached?

        What if it weren’t his boss receiving the comments, but it was the night auditor who reports to him?

        HR needs to know. Period. There isn’t a “top performer” exception for being a jerk. HR may need to coach him on how not to be a jerk.

        To me, this is a pretty blatant example of the first steps of sexual harassment. I’ve gone to our HR department with exactly this scenario, and they counseled and coached the offender.

    3. OP*

      I think this is somewhat missing the point. Her question has never been, “Should I do something about this?” She knows she has to do something about it. The question is, “How do I do something about this?”

      Obviously if it were an explicit comment, she could easily say, “Bob, that’s not appropriate for the workplace. Do not make comments like that to me or to anyone else” and then she’d need to report it to HR. When it’s something like this that could be taken sexually or innocently, it’s harder to deal with.

      Also as a bit more background as to why she’s hesitant to just fire this guy: when she started in this position (as I mentioned, about a month ago), she found out that the hotel’s books were a big mess *and* her boss wanted her to terminate two employees who weren’t performing up to par. She’s terminated those people and is in the process of finding their replacements. But right now she’s understaffed and trying to clean up messy finances. The last thing she wants is to have to fire a top performer over remarks that may or may not be construed as sexual harassment before at least giving him a fair chance to stop. And giving him a fair chance to stop means saying something to him directly so that he knows it’s unacceptable. Her problem is that she doesn’t know what the appropriate thing to say would be.

      After reading a few comments and Alison’s response,
      I suggested the following, which I thought was appropriate: “Listen, you’ve made comments that have made me uncomfortable. For instance in X situation when you said Y. You may or may not have meant it in a sexual way, but I took it that way and it needs to stop. If it doesn’t, Z will be the consequence.”

      1. Mike C.*

        Oh yes, of course! I totally forgot about the “being short staffed and performing better than the other folks who are on their way out means I can hit on the ladies” rule. My wife will be thrilled to hear that!

        Look, we’re all adults here. We all know when a comment can be taken multiple ways. Occasionally it’s accidental, but given that as adults we don’t wander around all day giving presentations to managers or clients filled with innuendo, it means we know what is appropriate for work and what is not. And yes, maybe it’s slightly harder to deal with, but that’s why managers make the big bucks and get the shiny office with the nice window. Their job is to do the hard things and nib problems in the bud before they get out of hand. Sexual harassment doesn’t usually take the form of some guy just dropping his pants in the middle of the company picnic, it’s much more subtle than that.

        As for your suggestion, she’s the damn manager. The boss. What she says, goes. All she has to say is, That’s not acceptable behavior, I expect you to stop. No equivocating, no ifs, ands, buts, or “maybe you didn’t mean it that ways”. These are two adults and they both know what is acceptable in a professional environment and what isn’t. Sure, he might gaslight her and claim it was perfectly innocent, but that’s not because he’s actually innocent, but because he’s a jerk trying to take advantage of the situation.

        Anything less opens the door to further crap from this guy or undermines her authority as a manager.

        1. KellyK*

          Sure, he might gaslight her and claim it was perfectly innocent, but that’s not because he’s actually innocent, but because he’s a jerk trying to take advantage of the situation.

          Yes, absolutely. If he claims it was perfectly innocent, her response needs to stay just as firm, and not debate with him about what he meant or didn’t mean. What he *said* was inappropriate, period, end of story, and he needs to not make those comments.

          1. fposte*

            Right. The OP and her friend are bogging themselves down in preparing to argue with rules-lawyering and intent-pleading, and the thing to do about those is to shut them down because they don’t matter. She can even straight up say that if he starts claiming innocence or she didn’t mind before or whatever: “That doesn’t matter. It’s behavior that has to stop now.”

      2. Ask a Manager* Post author

        “Listen, you’ve made comments that have made me uncomfortable. For instance in X situation when you said Y. You may or may not have meant it in a sexual way, but I took it that way and it needs to stop. If it doesn’t, Z will be the consequence.”

        I think that’s too much. It doesn’t need all that explanation and qualifying, and it will make her sound unsure and sound as if the door is open for him to debate it with her. Just a simple, “Those sorts of comments are not appropriate. Do not make them to me, or to anyone else here.”

        “Obviously if it were an explicit comment, she could easily say, “Bob, that’s not appropriate for the workplace. Do not make comments like that to me or to anyone else” and then she’d need to report it to HR. When it’s something like this that could be taken sexually or innocently, it’s harder to deal with.”

        But what people here are trying to tell you is that no, it’s not harder to deal with. You deal with it in exactly the same way. I understand that she feels it’s harder to deal with because it doesn’t feel as clear-cut to her, but … it IS clear-cut, and it really just needs to be dealt with in the same way.

        On it being clear-cut: Your letter said, “He’s begun making comments that are becoming increasingly sexual in nature. It began with remarks about how her boyfriend is ‘so lucky to be with her’ and has grown to the level of what she describes as ‘increasingly explicit double entendres suggestive of S&M.'” There is no grey area here. It doesn’t matter that he didn’t proposition her or comment on her breasts. These comments are inappropriate (and she knows they are, because that’s why she’s having the reaction to them that she’s having), she has an obligation as a manager to tell him to stop and alert HR, and she could be in a lot of trouble if it comes out later that he harassed someone else and she didn’t handle it this way.

        1. pidgeonpenelope*

          I’m with you here. I’m sure this gal is great in many ways but we all have opportunities.

          I’m really bothered that a manager is not sure how to handle this sexual harassment situation. I’m not sure this is the fault of the gal or the company she works for. I know my company does management training. I would expect she would be familiar with how to handle this situation.

          I’m also concerned about the gray area friendship she has with her subordinates. While not good, I understand when you’re a young supervisor in a retail store having friends with subordinates. However, when your’e that high up, do not be friends with your subordinates. In fact, as much as I adore my coworkers, I keep a friendship distance with them. I don’t want to talk about work on my personal time. I don’t want my friend or I to get promoted and then be in charge of the other and have to deal with that new boundary. I am friends with former assistant managers/shift supervisors/etc but those dear friends taught me the reason why I know to keep a relationship distance with superiors/subordinates.

          1. Rana*

            Agreed on finding her inability to deal with this worrying. Imagine if she was your boss and the same guy started harassing you. She’d come off either as incapable of dealing with this stuff (in which case you’re on your own) or, worse, tacitly approving of it.

        2. KellyK*

          A couple things that she should keep in mind that might help her deal with this exactly the same way she responds to a blatant comment:

          -People who enjoy harassing other people *deliberately* use double entendre or remarks that they can later claim were “misunderstood.”

          -If she lets an employee be harassed, it won’t matter that this guy’s comments could be taken innocently.

          -Usually when people accidentally make a comment that can be taken sexually, they’re embarrassed. If he’s not saying “Oh, crap, that came out wrong. I’m sorry, I didn’t mean it like that at all,” then smart money says he meant it exactly that way.

          -Talking about how lucky her boyfriend is to have her is already getting into inappropriate territory and it would be totally reasonable for her to respond with “That’s not appropriate for the workplace.” right then and there.

          -Even *if* she’s totally misunderstanding (she’s probably not) and his comments were meant innocently (I doubt they were), her reaction (tell him to stop and inform HR) should still be the same. On the off chance that the double entendres were inadvertent, he still needs to know that he’s making inappropriate and offensive comments so that he can quit doing it. No one’s saying fire him on the spot.

      3. fposte*

        That response is also very personally based. This isn’t personal; this is business; leave the “I messages” at home. Her feelings–or his, for that matter–shouldn’t come up in this conversation. There’s no interpretation to be explored here or benefit of the doubt that needs to be entertained, because nothing savage is happening to him. This is not a quandary. This is a straightforward thing to do and she needs to do it.

        1. KellyK*

          Good point. The response would be totally reasonable from a coworker, but as the boss, she needs to be a lot more firm than that.

          And also, making her uncomfortable is beside the point. If she didn’t mind at all, she’d still be obligated, as his boss, to tell him to stop because it’s not appropriate.

  15. JEM*

    As an HR Professional, this has “lawsuit waiting to happen” written all over it.

    OP – Your friend is a manager and is therefore legally held to a higher standard than non-managers. If the offender starts making comments to someone else, or if someone overhears the remarks made to your friend and is offended, your friend can be held liable for NOT acting on this because she is the manager.

    She needs to address this immediately and clearly. It will keep her 1) out of legal trouble, and 2) hopefully get the behavior to stop. A third bonus is the experience of dealing with a difficult situation like this – if management is something she plans to make a career of, then she’ll undoubtedly have many other difficult conversations to deal with in the future.

    Best of luck to her!

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