updates: CEO is furious about my joke, boss keeps saying he loves me, and more

by Alison Green on December 6, 2024

It’s “where are you now?” month at Ask a Manager, and all December I’m running updates from people who had their letters here answered in the past. Here are four updates from past letter-writers.

1. My CEO is furious about a joke I made

Thanks for publishing my letter. I wasn’t able to respond to comments that day, but I read all of them. Some commenters speculated that the CEO initially thought I was serious and was alarmed; he definitely knew I was joking from the get-go and did not like being the butt of the joke. (Most of his jokes are intended to keep the subject a little off balance, but that is supposed to be a one way street).

A coworker later suggested that since another PM was in fact struggling with keeping up with her project, which was causing major problems, the CEO might have thought I was referencing her struggles and it hit a little too close to home. I wasn’t, but it would make his reaction a little more explicable.

I have also since learned from other folks in the industry that he has often responded disproportionately angrily to things you wouldn’t expect. Overall the joke probably helped my reputation amongst my coworkers since most of them disliked the CEO, so they found the situation amusing because it made him look thin-skinned and a little foolish.

I didn’t see the CEO for a while after this incident and while he clearly remembered the encounter, he didn’t mention it and congratulated me on how the project went. The division VP who’d reprimanded me started acting more abrasively towards me, but he was treating everyone the same way so I didn’t take it personally. My boss did mention the incident in my yearly review as a word of warning, although he clearly thought the CEO’s reaction was ridiculous.

Shortly after many people I worked with left the company, and I did as well. I ended up finding a much better-paying job, remote, with really good (and pleasant) bosses who have no issues with humor. So far I’ve been very happy here.

I’ve kept up with some folks from Old Job and it seems many are thinking of leaving. I would never, ever work for either CEO or VP again if I can possibly help it, so it’s not likely I’ll ever run into these folks again (but it’s a small industry so who knows!). Since things turned out okay, I don’t regret making that joke, although in a vacuum I wouldn’t do it again. The whole situation really opened my eyes to the importance of corporate politics; somehow I’d mostly avoided it before this but the amount of gossip and nepotism at that job was incredible. Overall, I’m happy with the way things turned out.

2. My boss keeps telling me he loves me

As many of the commenters guessed, my boss does come from a place where “I love you” or “love you” is a common way to end a conversation, although he doesn’t seem to do it with anyone else. He’s pretty much stopped, presumably due to me giving a weird look every time he said it. Our working relationship continues to be strong! He promoted me to the senior leadership team and I continue to be able to bring up challenging topics with him that others couldn’t. He does suffer a bit from lack of boundaries — just recently he mentioned to me that he had a prostate exam, but it was fine to tell me because “they do blood tests now, not the finger up the butt. Well, they still stick the finger up the butt later, but that’s after the blood test I think, they just don’t open with the finger in the butt any more” — but that’s just who he is. And frankly, it’s refreshing to work for a boss whose “finger up the butt” stories are medical. That’s progress for my industry.

– still don’t love him, but I like him just fine

3. Can I take off a full week when no one can cover for me? (#4 at the link)

Your advice was indeed very helpful and reassuring.

Here’s my update: The company hasn’t changed much, but I have:

· I’ve required that others provide information I need to fulfill their product needs on a timely basis, or it doesn’t get done.

· I’ve made it clear that because of my broad background, I can do almost anything, but not everything. We can do “A,B,C” but not “D,E.F.” If I’m clear and consistent, I don’t get heavy pushback. This has reduced workload.

· I insisted I be allowed to hire freelancers who can take on much of my back-office work, making it easier to get ahead before vacations.

Those three items above have made real vacations possible for me and for the company. I also made a logical case for raises. They weren’t large, but my staff and I got something, which improved morale here.

4. Our director left while my coworker was on vacation (#3 at the link)

The advice was spot on.

My update is that the coworker was fine learning about the news in a casual way when she got back. Unfortunately, I was not hired for the permanent position. There were a lot of red flags in the hiring process. The interview was scheduled at the last minute (on a Thursday when she pledged to announce who was hired on a Friday). The executive director also told me, verbatim, after my interview, “Well, you know I want to hired you, but I have to interview Jane to make sure she doesn’t get mad.” She took Jane on a 15-minute coffee interview the next day. She gave Jane the job. For reference, Jane has less experience, training, and credentials than me. I was given a smaller promotion but that wasn’t enough to balance out that Jane and my ED cut my most interesting tasks, removed me from all important conversations, and undermined me at every turn. After a long and frustrating summer, I got a new job in a related industry for a little less money. I am thrilled with the new job and excited for a fresh start.

The most interesting part about my new job is that I’m in a “project engineer” role (my smaller promotion was to “senior engineer”) so technically a step down, but the levels at my new organization are massively different. At my old org, my new director and ED were very young and inexperienced. The new job, people have way more experience. While that likely means I won’t make my way up to senior engineer in the near future as I hoped, I am actually a lot happier to be learning and growing with people who have something to offer in terms of professional growth!

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{ 45 comments }

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  1. Hlao-roo*

    #1 – I appreciate the irony that the CEO hating your joke gave you a better reputation with your coworkers. Glad you’re at a better job now.

    #2 – Glad your boss has tapered off the “I love you”s and is still a good boss!

    #3 – Thanks for sharing the changes that have allowed you take real vacations.

    #4 – What a terrible hiring process at your old company! Glad you are also at a better job now.

  2. Jen in OR*

    “And frankly, it’s refreshing to work for a boss whose “finger up the butt” stories are medical.”

    *snort!*

    1. Consonance*

      I really appreciated that! There really is a difference between “well that’s a little out there” and “that is offensive” !

      1. Superfluous and Sassy*

        The line is pretty slim between “that’s a little out there” and “offensive”. If finger up the butt stories are medical, does that make them okay? Even if it seems innocuous, it’s bringing a sexual component to the workplace. I don’t think this is as innocent and LW is hoping it to be, particularly with the backstory of the boss saying he loves her. A lot of creeps try to explain away their sexual fixations, as the boss is doing here. Yes, some people are overshares, but that doesn’t give them a free pass to talk to their subordinates about private parts and putting fingers into them.

        To give another example, I was once working with a cultural group on a very fulfilling project. However, one day, while alone in a forest with a member of this group, he told me a story that he said was culturally significant. It was a story of incest, with many rambling details about sex. But according to him it was just a mythical story that his culture has passed on for generations. Does that make it appropriate to tell to a female colleague when you have her alone?

        1. a clockwork lemon*

          There’s nothing sexual about a routine medical exam, especially not in the context provided by the LW. It’s possible to be a chronic over-sharer without being some sort of sex pest or predator, and it’s clear from LW’s anecdote that boss is the former.

        2. Consonance*

          Yeah, I definitely don’t mean that just because they claim ignorance that’s the truth. I’m just taking the LW at their word about this particular person and situation. It sounds like your experience with someone was different, for which I’ll similarly take your word.

        3. Peanut Hamper*

          I am having a hard time equating “a story of incest, with many rambling details about sex” with a prostate exam. This is not an apples to apples situation.

    4. SomethingClever70*

      Omg, that boss actually sounds hilarious. I’d probably get along with him really well. I guess that makes me problematic as well!

  3. Sassy*

    #2 – Oh my… details about prostate exams are definitely NSFW, verging on sexual harassment. Even if it’s veiled under the guise of “medical reasoning”, talking about private parts should never be brought to work! And do you think he’s oversharing about his prostate and butt-finger experiences with his male colleagues? I also experienced this once with a coworker, he was simply explaining that he was off work because he had a prostate issue, then as a simple clarification (because I need to be mansplained at) he told me how the prostate is connected to the penis, and went into great detail about his penis – all under the guise of needing to inform me of a simple medical procedure that was pertinent to why he was off work. Fucking gross. And he told this to me while I was in a room alone with him. He thought it was necessary work-related detail, but oddly enough it wasn’t so necessary that he brought it up in our team meeting.

    1. Socks*

      Your coworker obviously knew what he was doing, but if the LW didn’t get that vibe from her boss, I could very easily someone prone to foot-in-mouth-itis rambling through a train of thought like: mentions prostate exam -> oh no the LW thinks I’m talking about a finger up my butt -> says they don’t do that anymore -> realizes that that’s not true -> clarifies that they DO but that’s not the whole thing

      1. Superfluous and Sassy*

        I do see what you’re saying. The LW’s boss may not have intentionally talked about putting fingers into butts. But – intention is actually not that important. Someone higher up needs to tell this manager to stop telling his subordinate about his prostate and fingers being up his butt. This actually could be the crux of the problem. The LW’s boss is clueless about boundaries. That doesn’t make any of this okay. LW was clearly uncomfortable with “I Love You”, and it seems to me that the boss has now warped her sense of what is normal and okay. Even if LW finds it refreshing for sexual stories to be told from a medical perspective, it doesn’t make it okay for people to be talking about sexual (or potentially sexual) things to their subordinates.

        1. Saturday*

          I don’t think these are sexual comments. The lw is in the best position to judge, and it sounds like this conversation isn’t coming across as way off base. Some people are just more open about these things.

          “And do you think he’s oversharing about his prostate and butt-finger experiences with his male colleagues?” I could definitely imagine the answer being yes.

          1. Socks*

            Yeah, this. I don’t think what the boss said was appropriate, but I don’t think it was sexual. I also think it’s pretty unkind to the LW to say her perspective must be warped because she didn’t react as strongly to the oversharing as you (Sassy) would.

        2. Irish Teacher.*

          I wouldn’t consider that to be a sexual story. An inappropriate story, yes, because the imagery is pretty gross, but I don’t think there is anything inherently sexual about a butt being examined medically.

          Now a creep could make it sexual and I could well imagine a sexual harasser talking about finger up the butt tests and grinning or eyeing the other person in a way that indicates he is hinting at something different from medical examination but it doesn’t sound like that is the case here.

          1. Bird names*

            Yeah, gotta agree with Irish Teacher here. It seems a bit of a leap from “medical oversharing” to “definitely sexual”. Just because a human body part is discussed, does not automatically imply sex. Absent additional indicators such as *grinning or eyeing the other person in a way that indicates he is hinting at something* as Irish Teacher put it, I’d consider it TMI, but that’s it.

      2. Dawn*

        I honestly found it a little adorable, yeah. I could see doing that “thought process out loud” thing myself for sure!

    2. Alicent*

      It’s not innocent when they do that. My dad has a similar fixation on prostate issues and penile function and it’s entirely obsessing with losing function and how he would lose the will to live. It’s super gross and they know what they’re saying.

    3. Crashing into Middle Age*

      So…I was in the Navy for many years, at times the only woman or only one of a handful on a ship, which gave me plenty of opportunity to hear male only conversations (things overheard or heard in passing, not for my benefit). And those dudes did indeed discuss prostate exams and fingers up the butt (like, a lot). It is just a Topic of Conversation, just as women will discuss the joys of being squeezed by the mammogram machine and have it not be sexual.

    5. Alz*

      I disagree that it is inherently inappropriate- A lot of men avoid the doctor because they expect it to be embarrassing or painful- The more that these kinds of medical things can be normalized the better it is for everyone. If it is done in the right tone it is no more inappropriate than a woman talking about her period or menopause. I totally agree that people can talk about these things inappropriately but, well, heck, the idiots I work with can make inappropriate comments about the dinner menu or the printer being out of ink- tone and context is important.

  4. Lana Kane*

    If this site had Reddit-style flairs, I’d use “they just don’t open with the finger in the butt any more”.

    1. bleh*

      Funny how they were able to create a blood test so men can avoid invasive exams. Still no blood test for cervical cancer. Hint: it would be easy for them to do, but women accept invasive tests where men won’t.

      1. Crashing into Middle Age*

        This year the FDA approved a self test kit for cervical cancer! So instead of a pelvic, you self swab. Not quite a blood test, but could be an improvement! and most women went from getting PAPs every year to every 3-5 within the last decade. Some things are less terrible than they used to be!

        1. Self Swab FTW*

          I did the self swab this year and it was SO easy. I don’t even use tampons because I find them very uncomfortable, but my doc handed me the little broom thing and left the room, and I got the sample first try and had no pain.

      2. bamcheeks*

        But the HPV vaccine is going to *dramatically* reduce the incidence of cervical cancer in my kids’ generation, potentially to the point where smears aren’t routine. There are a ton of examples of cancers which affect women getting less funding and research than ones which affect men, but I’m not sure this is one of them.

        1. Bird names*

          Yeah, wasn’t there a follow-up study in Sweden that already showed the numbers dropping noticeably for the ones that got the very first vaccines?

      3. varied*

        Could you share data that a blood test for cervical cancer is a good test, and that “it would be easy for them to do”?

  5. I'm just here for the cats!!*

    #1 glad you are in a better job now. This made me think of the letter where the office had a no humor policy. Maybe the CEO used to work there?

  6. 2e asteroid*

    It’s not as dramatic as some, but this post definitely falls in the “combination of headlines suggests interesting fanfic” AAM bingo square.

  7. I Have RBF*

    Re “finger up the butt”: So, everybody has butts, and most people require colonoscopies at some point in their life. I guess I don’t see it as sexual, but it is medical TMI, just like talking about placing a catheter is medical TMI.

    1. RLC*

      And medical TMI can often squick out one’s colleagues! I’ve had a few memorable ones, including one who turned an office wide safety meeting into a plea to have prescription-only antibiotics included in our first aid kits. Boss pressed him for details (big mistake in retrospect) so employee described “weird mysterious rash needed treatment sooner than I could get to doctor’s office”. Rest of staff in meeting visibly shrank away from rash dude. Rash dude also once asked me if I thought his behavior put him at risk of STDs…I pointed out that he should consult a medical professional with such questions, not my area of expertise as I am a civil engineer.

      1. Reluctant Mezzo*

        I used to be a nurse’s and someone else at the office used to work in the ER. We could play ‘grossout’ and clear that office in about ten minutes (mostly men). I should not be proud of that, but it was fun at the time.

  8. HolidayAmoeba*

    For LW#4. People get really hung up on titles, but as you’re learning, knowldge and experience are what will really matter in the long run. And a person with a senior title and no experience to back it up can cause a ton of chaos. So it’s okay to not have that senior engineer title for awhile yet.

  9. I'm great at doing stuff*

    #1 reminds me of a situation at a former job. It was a very relaxed atmosphere with lots of joking. Someone new was hired to head up a committee and while she was going over our roles I made a joke similar in tone to the LW. She stopped and stared at me and said, “Are you done?” with zero irony or humor. But she ended up abruptly leaving (not sure if willingly or not) and I lasted 12 more years, so who had the last laugh? Me! Hehe

  10. Insubordinate Clause*

    #2 – If someone veers off into territory that’s uncomfortable, you don’t have to put up with that – and you are sending a message that NO ONE should have to put up with that. You don’t have to be obnoxious about it, but call it out so your boundaries are clear. Something like, “Whoah, whoah! I’m gonna stop you right there with the prostate talk. TMI! Let’s move on to a work topic.”

    1. varied*

      Yeah, or even, I dunno, just start fake coughing –cough– suddenly and — cough — oh, wow, one sec — cough cough COUGH – ah, excu — cough — excuse me, I need to get some COUGH COUGH — water. [exits comment]

      Not all lies are bad, and some are quite forgivable.

  11. Avery*

    The joke was not hilarious but it wasn’t insulting and CEO overreacted. I think this falls under know your audience.

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