does using humor risk undermining me as a manager?

by Alison Green on November 16, 2023

A reader writes:

I am a brand new manager at a rather small company and have one employee who reports to me, my first ever report.

Typically in the past I’ve built relationships with coworkers and managers with work-appropriate humor and puns, with a decent amount of my jokes being self-deprecating (Think jokes about the thickness of my glasses or relating a story about my panic over a small mistake I once made.)

This strategy has been successful for me in building up warm, collaborative relationships with my colleagues. My jokes are all safe for work, and I have never received a complaint about the context or the timing of any humorous remarks, and I tailor any humor to my audience and by reading the room.

My question is, does using humor to connect with my employee come across as inappropriate or risk undermining me? Right now I am training them and am planning for them to have the freedom they need to run their areas as they see fit under general guidelines that I’m laying out, and I am finding myself automatically turning to my usual humor to impart lessons about mistakes in that position I’ve personally made and to build a friendly relationship. Could this cause me or my employee any problems in the future?

I love this question because humor can be a great way to humanize yourself, connect with someone, lighten a conversation, and generally just making work more pleasant.

But it can also come with risks. It sounds like you’re avoiding the obvious no-go’s (like sexual humor or humor based on stereotypes) but some of the other risks to be aware of are:

  • inadvertently undermining yourself or someone else (more on that in a minute)
  • making someone feel bad (you need a lot of trust in a relationship to joke about the other person, and even then need to tread carefully)
  • making light of a situation that someone thinks you should take more seriously (especially as the boss)
  • being sarcastic (which can come across as unpleasantly negative to people who aren’t heavy-sarcasm users themselves)
  • seeming like you’re punching down (if you’re joking about someone with less power than yourself)

In your case, because it sounds like you use a lot of self-deprecating humor, I’d say to be thoughtful about the quantity of it. Self-deprecating stories or jokes can be fine in small doses, but when they’re frequent, they can make people have less confidence in you (especially because you’re new) or make them feel like they need to prop up your ego, which you definitely don’t want at work. That’s not to say that there’s no place for self-deprecating humor at all, because there is; for example, if you’ve got a staff member who’s excessively beating themselves up over a mistake, it can help to share a funny stuff about a mishap of your own. But if you’re constantly self-deprecating, you can diminish people’s confidence in you.

So the key is to be thoughtful about all of these things and get the balance right. If you do that, humor is a good thing. (Most of us would not want to work in this office, after all.)

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{ 124 comments }

{ 124 comments… read them below }

  1. Maple Leaf*

    I recently had this come up with a client on my caseload ( I manage a caseload of long term disability client’s who received social assistance). He was trying to scan then email a document to me and was struggling with the tech aspect. I relayed that I had just returned a loaner car to the dealership while my car was being repaired. I explained I hit a button that opened the moon roof, and could not for the life of me figure out what to hit to get it closed again. I had to walk into the dealership with my head hung low, and tell them they had to send someone out to close it.

    All I could do was laugh at myself, as I also struggled to start the engine with the push button start (PSA: you need to press the brake to push start a car!).

    The client chuckled along with me and even said how grateful he was that I shared the story with him, and that we are all human who sometimes struggle with new things. It really went a long way in building the rapport with the client.

    1. ThatGirl*

      The first time I drove a push-button start car was about 10 years ago, also a dealer loaner, and I had to walk back inside and ask how :D so I’m glad that isn’t just me hahaha.

      1. Charlotte Lucas*

        I had the same thing happen, about 15 years ago, when they weren’t at all common. With all the different types of keys and starters these days, rental agencies should just hand out instructions.

      2. A Poster Has No Name*

        Yup, 100% had to go in and ask how to get the car started the first time with a push button.

      3. Greta*

        I just sold my 25 year old car and bought a brand new one (my first new car ever!). It’s like driving a space ship!

        1. Charlotte Lucas*

          I am reading some books from about 100 years ago. They mention push button starters.

          Everything old is new again.

          1. JustaTech*

            OT: when my grandmother was a child (so, the 1920’s) one of her neighbors had an electric car. It had a tiller rather than a steering wheel and was slow as anything.

          2. Clisby*

            I learned to drive in a car (Rambler) with push-button transmission (regular key starter, though.) I loved it. I wish I still had a car like that.

      4. Hiphopanonymous*

        About ~15 years ago I bought a new car. The version I test drove was an automatic, but the one I bought was a manual – I’d been driving manuals for 10+ years at this point, and I really wanted a manual. I did all the paperwork, paid, etc., and the salesman tossed me the keys.

        I spent the next 20 minutes trying to figure out how to put the car into reverse. I’d driven cars where you had to push the gear lever over really far/hard to get into reverse, cars where you’d had to pull up on a ring under the shifter to get into reverse, and cars where you had to move a little physical blockage out of the way to get the car into reverse. But this car, you had to push down on the gear knob to get into reverse. I had to go back into the dealership and ask the salesman how to get into reverse so I could take home my brand new car I’d confidently assured him I could drive. Doh!

        1. Bexy Bexerson*

          I had a somewhat similar experience when I bought my car in 2017. It’s a 2012 Mazda 3 with a six speed manual transmission. I went to this dealership specifically to look at this car, because I wanted to go back to a manual after driving automatics for a decade, and I had loved my previous Mazda 3, which was a five speed.

          The sales guy didn’t come with me for the test drive because he was busy closing another sale. He just tossed me the keys and let me go for it. I go out to the car, get in, start it up, and then… then I couldn’t get it into reverse to back out of the parking spot. Lucky for me the parking lot had a slight incline, so I managed to back out in neutral.

          Got out of the parking lot, got on the highway, ran through all six gears with great joy and knew I was absolutely going to buy this car. But I needed to figure out how to get it in reverse! I pulled into a random parking lot and figured it out by dumb luck, but I still didn’t understand exactly how I’d done it.

          Drove back to the dealership, told the guy I wanted to buy it, got the financing taken care of…and then when I was getting ready to leave I asked “So, umm…how exactly do I get the car into reverse?” and he was very kind and explained the push down thing.

          Six years later that car still runs like a dream and is fun as hell. I’m going to drive it until the wheels fall off. But I still sometimes end up in first when I’m going for reverse, and vice versa.

    2. Silver Robin*

      Humor to ease another person’s shame, especially in a “you are far from the only one” definitely seems like one of the safer routes to go.

      1. goddessoftransitory*

        I use it a lot in training! “There is nobody in this room who hasn’t struggled to figure this out, including me. *anecdote*”

      2. Clare*

        My go-to when the checkout or reception computer isn’t working, and the person behind it starts to apologise is: “Ugh, computers, right? They say they’re supposed to make our lives easier, but I’m not convinced”. It usually gets a grateful laugh when they see I’m feeling sympathy rather than impatience.

    3. Not Tom, Just Petty*

      I read your comment a couple times and I’m typing this because I’m thinking about it for myself to figure out WHY is it a great example and I think I get it
      This is a great example, because you are ultimately talking about how you learned something new, not about how you don’t know some specific thing.
      Your point is that it can be so freaking embarrassing but you do have to suck it up and ask how. And you can even laugh about it later.
      That’s the humanizing quality.
      It would cross into “emotionally needy” by continuing with:
      “I guess I’ll never have a new car. If those guys at the dealership saw me walking in, they’d tell me to get on the bus because I can’t figure out ANYTHING about these new cars.”
      And if each interaction after was a call back, like, “drove my self in today. Even managed to turn on the headlights. I should get gold star!” type of look-at-me versus shared universal.
      So thanks for letting me has that out.

      1. Lily Rowan*

        Ooh, that is exactly right, and that is how to do this! It’s not “I’m such a dummy,” it’s “I didn’t know a thing and now I do, and here’s how.”

        2. wordswords*

          Yes, this is a great breakdown of why your example works, and what could make it not work as well!

    4. lyonite*

      This is a good example because it’s a funny story where the joke is on you, as opposed to self-deprecating jokes that are just “God, I’m such a mess.” Which can definitely be funny, but that’s the sort of thing that can be undermining as a manager. (Or anyone, really. I’ve had to train myself out of making so many jokes along those lines after a couple of people pointed out that I was dragging myself too much.) (I also wonder if this is a gendered thing for women? Like, someone compliments you and you’re supposed to say, “I look like a cave troll” or something instead of accepting it?)

    5. Rocket Raccoon*

      I had a trainee ask me how I instantly knew the fix for every mistake she made. Told her “because I’ve already made the same mistakes!”

      1. Peanut Hamper*

        Ha! We just went through a major IT transition at work and I’ve been getting messages right and left asking for help, and when I respond, I get that question and am able to give that same response. BTDT is definitely a thing!

    7. nervous wreck*

      Omg, I borrowed my partner’s push to start car for the first time and I thought I had started it…… I actually managed to back it out of the driveway but it wasn’t actually on so the pedals stopped working and I had to call him in a panic to come out and fix his car. Very embarrassing lol.

  2. Sciencer*

    I think one risk of self-deprecating humor is that you can end up insulting someone else. Like if you forgot makeup one morning and joked about looking haggard without your base layer or whatever, you might make someone who doesn’t wear makeup worry that they’re always looking haggard to you. I think just avoiding that kind of humor when it comes to your body or physical appearance is probably wise in a work setting.

    1. Lucy*

      Yeah, you want it to be clear that you wouldn’t laugh at the person you’re training if they make a similar mistake later.

    2. Silver Robin*

      I also worry about folks feeling like they might have to reassure OP. Like if they keep making jokes about how bad they are at X task, I can see reports feeling like they have to step in and say “No, Boss, you’re great at it!” or “No worries, it is not a big deal!”. Some folks use self-deprecating humor as a bid to for comfort/reassurance (myself included every so often), and that can feel really weird in the workplace and especially with power dynamics at play

    3. Combinatorialist*

      This is especially true in contexts with people with different backgrounds. The first semester I was a TA for calculus, I was joking with my students in break and was telling some story about dumb, young me who didn’t know you couldn’t divide by zero and how goofy I was. And one of my students in all earnestness was like “you mean, I can’t divide by zero” and he felt really really stupid and I felt really bad. So now I don’t joke about not knowing something because then if someone else doesn’t know it, I’m not implying its so obvious its a joke.

    4. Dread Pirate Roberts*

      Yes, very true. I had a boss who was constantly talking about how old she was, forgetting things because she was so old, out of touch because she was so old. Of course I was the same age as her, as were others on the team – and we weren’t THAT old or feeling out of touch and whatnot, and it came across as hugely ageist so none of us wanted to speak up and tell her how old we were. The example in the letter that seemed a bit similar was the thick glasses. I wear contacts so you can’t tell how thick the glasses I wear at home are, but more to the point I work with someone with a visual impairment that not everyone knows about. I don’t know that either of us would feel bad about a comment like that but you just never know with self-deprecation who you’re including in the insult.

  3. Sparkles McFadden*

    Humor at work is generally a good thing, but I only used it with people I knew well enough so I would be sure how a joke would be received. I must admit that I used humor at work far less often as I transitioned to management. I just thought it was important to be clear with the people reporting to me, and that was easiest if I didn’t make light of anything. That said, I would still use humor if I thought it would make someone feel better or less stressed. I saved my sarcasm for non-work situations, though something would slip out here and there.

    I did once work in a department complete devoid of humor, and that was so very odd. It was like working on another planet. My time there did help me hone my deadpan delivery, but I was relieved when I transferred to a department where it was OK to make a joke.

    1. RegBarclay*

      Yeah, knowing people is key. Not long ago I was in a meeting with my boss and he was laughing uproariously at something I did. And I had zero idea whether he was laughing because he thought it was clever, or because it was the stupidest thing he ever saw. HE probably thinks it was obvious, but it really wasn’t.

      To be fair, it’s on a long list of minor issues I have with my boss. If we had a better relationship I’d either assume the best or be comfortable asking.

    2. Escapee from Corporate Management*

      This is so important. Using self-deprecating humor is okay IF the audience is in on the joke. If your team is having doubts about your management skills, it may not come off the way you expect.

  4. AskJeeves*

    Self-deprecating humor can be great, but illustrating a training for a direct report with many stories about mistakes you’ve made, and laughing about them, is probably not the best approach. Just wait until you know the person better and vice versa.

    1. Snow Globe*

      Yes, one potential problem is that you might be sending a message that mistakes are not a big deal. That can be an ok message with a good employee who beats themselves up about small mistakes, but could be a bad message to someone who already has a cavalier attitude towards mistakes.

      1. WantonSeedStitch*

        This is why I would use the humor *in response to* someone beating themselves up too much about small mistakes, or during a time when a lot of small mistakes are expected and folks shouldn’t feel badly about making them. In my job, we have a lot of written work product, and it’s pretty much a given that even if you’re an excellent writer, when you start out, you’re going to get LOTS of edits from your manager on your work. I’ve let the people I’ve trained know, “look, you need to expect a lot of red pen in the first few months here. I got a masters degree in journalism, and I saw fewer red marks from my journalism professors on the articles I wrote for class than I did on my first few TPS reports here! It was like someone splattered ketchup on the page! But you’ll get the hang of the specific way we write things HERE soon enough.”

        1. Exile from Academia*

          That’s exactly it. We’re required to document almost every mistake at my job (not for tracking individuals, but to see if we need to change process or training if a whole bunch of people are making the same mistake) and people in their first few months often panic and feel like they’re terrible at their jobs because they’ve never had that sort of concrete list of every mistake they’ve made before.
          So I say things like “Hey, I made the same mistake when I was new. Most people do at least once. Now, if I was still making that same mistake four years in, we might have a problem, but we expect new folks to take a while to get everything down. Now let’s talk about some strategies for avoiding this happening again,” and that generally works well to keep people from beating themselves up too much without downplaying the need to prevent similar mistakes in the future.

      2. Tio*

        It can also risk coming across like you don’t know what you’re doing if you use too much self-deprecating humor. If you come in and hear a bunch of stories about your boss not knowing what they’re doing, that could actually be a big red flag. So you want to be really careful about what you’re joking about and how often.

        1. AskJeeves*

          Yes, this is definitely one of the risks I was thinking of. As a new employee, I’d be wondering if my boss was actually competent.

    2. ferrina*

      I think about this more as sharing information through storytelling, rather than humor.

      “When I was in your role, I learned this lesson the hard way. I tried to speed up the timeline by automating the process, but I didn’t test the program in a test environment. I ended up messing up our original draft and had to rewrite it from scratch. I had to pull a couple very late nights to catch up. After that, you can believe that I always used test environments, or at the very least, always kept a clean copy of the original draft.”

      1. bio student*

        I think it depends on the exact humor. For instance, I worked in a biology lab as an undergraduate and while on a scheduled shift on the weekend where I was alone in the lab, I wasn’t wearing goggles and hadn’t pulled a fume hood all the way down, and managed to shoot pressurized formaldehyde into my eye, requiring me to use the eye wash (imagine putting your eye directly against the shower nozzle at full volume, then holding it open for 10 minutes), and then blurrily and soggily discovering that the building plan did not involve floor drains in labs and thus I needed to call *campus security* to get facilities to come wet vac the now ankle-deep water… And that, friends, is why we ALWAYS wear our safety goggles.

        1. AnonRN*

          I have said to mortified trainees “oh! You found a new and exciting way to make a mess!” usually followed by a story of a time I did the same thing, and why I only did it that way once.

          I’ve been doing things long enough that I’ve had the opportunity to make every kind of mess you can think of, they don’t need to be ashamed but I do want them to learn. Sometimes you only learn which way the tubing needs to be clamped by unclamping the wrong side…

        2. AFac*

          I winced so hard at this story, but unfortunately every lab researcher has a similar one. Mine involves a more experienced researcher asking me to help with a task that was so quick I didn’t need gloves.

          Also, for anyone reading this and wondering what to do in that scenario: don’t let the lack of drain keep you from doing the emergency actions you need to do. Water on the floor can be cleaned up. Damage to you can’t always be.

          1. bio student*

            Yes, it turns out this was a feature and not a bug– in labs working with the kind of chemicals where you need a fume hood and eye wash, you can’t have a normal drain that just dumps into the local sewer system (imagine if someone dropped a gallon jug of formaldehyde down the drain)– those drains have to be a separate hazardous chemical system, and apparently they did the math and wet-vac-ing every time an eyewash or shower was used was expected to be substantially less expensive than the fancy chemical drainage system. (And I’d imagine safer– there are some chemicals you really don’t want coming into contact in a closed drain that vents to a lab space…)

    3. r.*

      Maybe.

      It really depends on the phrasing, and if you have a strong error culture (and in all likelihood that is something you want to have).

      If you have one, using humor on *mistakes* (as opposed to errors) can be a great way to take the sting out of the discussion, and allow better focus on what matters most, ie how to prevent a mistake, once identified, from re-occuring.

  5. Hospitiful librarian*

    I have a coworker (not a manager though) that makes self-deprecating jokes that, while about himself and are not at the expense of any others, sometimes make me feel uncomfortable. Like once joked along the lines about how if you pointed to a stack of manure, you couldn’t distinguish it from himself. So I would also argue that it’s not just about using that kind of humor too frequently, but how you use it.

    1. jellied brains*

      Yeah if my boss kept making self depreciating comments, I would wonder if I was supposed to now big them up? I did not sign on for that kind of emotional labor.

    2. Radioactive Cyborg Llama*

      Yikes. That would make me uncomfortable, too. It barely sounds like self-deprecating humor to me, which is more along the lines of “I have human foibles” and less “I consider my whole self shit.”

    4. Despachito*

      Yes, this is true. Comments like this from other people have made me writhe in second-hand embarassment, although the deprecation was aimed at them and not at me.

      It sounds like fishing for compliments, or, like in your example, not even that. Social convention requires you to say “no, it is not that horrible”, but you may not always want to play this game. And the “manure” thing is so weird, I would not even know what to answer (“no, I think there is a thing or two on you that will enable me to tell you from the heap of manure” does not sound like something the person would want to hear.

    5. Jaydee*

      That’s not even a joke. Like, there is a HUGE difference between comparing yourself to a literal sack of $h1t and saying something like “I’d probably forget my head too if it weren’t attached” when you leave the conference room before the meeting starts to go back to your office because you forgot a pen. And again for your coffee. And also for the agendas.

  6. stk*

    Ooh, yeah, difficult. I do think it’s different as a manager: what is a perfectly reasonable, non-offensive piece of jollity in a colleague can so easily become EXTREMELY weighted the second that you have real power over the person you’re talking to, and you are not in a good position to know when that’s the case. And self-deprecating stuff can suddenly become a much bigger problem in terms of finding and embracing your place as a leader. I don’t think you have to be really po-faced when you’re a manager, but I do think you’ve got to be very careful. Especially when you’re new. Taking a genuine interest in your reports and how they’re doing, and doing your best to support them and the work of the team, is probably your best strategy for making positive relationships with them anyway, at least until you naturally have in-jokes or a really strong sense of where the lines are. Which is okay: your reports don’t want you to be a jokester. They want you to be their boss.

    1. Smithy*

      Taking the OP at their word that they are skilled at reading the room and using the right humor with the right audience, I do think the point about the OP being new to management is the key here. While humor can be an effective tool in many kinds of interactions, what likely feels awkward for the OP right now is having to go back to a more reserved and cautious kind of humor while they figure out management.

      If the OP was promoted into management at their same workplace, taking the mindset of truly having a *new* job and approaching humor with that same perspective. You’re learning a new working dynamic and therefore the style of humor and frequency of jokes is likely to be best served in a different way.

      Right now the OP may be finding a good way to connect with some direct reports around mistakes or other issues is humor, but whether it’s a different personality type or a different issue – having other approaches in your toolbox is likely helpful. And it may honestly be about the same story, but how that person will connect best with you. I once had a situation with a doctor where when getting the local anesthesia for inpatient surgery, I was clearly almost about to faint. In addition to now feeling poorly, the doctor could tell that I was feeling distressed and then proceeded to tell me this long story about catching an illness during residency from a patient that required a shot in the tush which caused him to faint.

      Any story that ends with a shot in the butt could likely be set up for laughs, but his approach was to tell it very slowly and calmly in a way that distracted me and ultimately was more effective regarding my own wooziness. Ultimately, I really respected this doctor for figuring out what I needed as a patient – and with mistakes or other issues – some direct reports will appreciate a more jovial or humorous dynamic. But others are going to be looking for something else, and the OP being able to balance different styles will just serve them well in the long run.

  7. Be Gneiss*

    I agree that too much of it can come across as weird, but I think it’s really useful in situations where someone has made an error and is embarrassed about it. It’s nice hearing “I know this feels horrible, but let me tell you about the time I made this embarrassing typo in a company-wide email, and it didn’t ruin my career.” Sometimes in a moment of frustration with technology, or after you notice a mistake, it feels like all eyes are on you and that’s what people will remember you for – like your legacy is going to be the woman who jammed up the copier for 3 hours during your fist week. It’s comforting hearing “I made an equally-embarrassing goof, and not only lived to tell the tale, but have succeeded in the workplace!” Logically, you *know* that stuff happens, but embarrassment can be hard to shake.

  8. MassMatt*

    Alison hit on many great points to consider. You definitely need to know your audience, and they need to know and trust YOU (it’s not always automatically reciprocal), and you need to be sure not to cross boundaries. This is especially true with customers, in most cases I don’t interact with them as much as with peers, so the trust takes longer to build than with coworkers. In general I follow the customer’s lead in how formal or informal they want things to be.

    You also need to be aware that as a manager you have a captive audience, you can’t expect underlings to laugh at everything on command. I also draw a distinction between taking the responsibilities of the JOB seriously, while not taking my SELF too seriously.

    All that said, I think having a sense of humor at work can really help to make a job more pleasant. I am known in my office as someone who jokes around, while not being a practical joker or making fun of anyone, and taking issues seriously when necessary.

    1. Generic Name*

      OMG, the captive audience. I do not miss cringing through all-company meetings at a small company I used to work at where leadership seemed to think that the meetings were their personal stand-up comedy stage. Lots of awkward/nervous laughter from staff. Made so much worse by the founder laughing and laughing, which obviously encouraged the “comedians” even more. Ugh.

  9. Jelly*

    May I add: humor, joking, etc. should be in periodic doses. It gets tiring being around people who constantly respond with rim shot-type answers.

    But it sounds like you’re handling things quite well. :)

  10. Prexit*

    I think there are two other problems with self-deprecating humour from managers.
    If the goal of it is to say “hey, I’m just like you!”, the problem is, you’re not. You have some sort of power over them, that affect their salary and whether they keep their job, and acting like “I’m just a goofball!” can come across like you don’t understand that.

    Similarly, if and when things go badly at work – heavy workload, company layoffs, whatever – people want a manager who seems to be taking it seriously, and not trying to joke through it. It makes it seem like you’re ducking responsibility.

    I always felt my current manager was a bit stiff, but when things at our company turned sour he was able to deliver bad news with the appropriate amount of gravitas, and I appreciated that.

    1. Radioactive Cyborg Llama*

      It heavily depends, but I don’t think joking sometimes =I’m a goofball who won’t handle serious things seriously. I joke at work, but I would never be like “LOL, you’re fired!”

  11. Miss Chanandler Bong*

    OP, my favorite manager ever was the one who occasionally made self depricating jokes, and I think it’s because he had an underlying humility that other managers lacked. After having several really bad bosses and then coming to him, it built up my confidence because I wasn’t afraid to come to him when I made a mistake and always understood it was part of the learning process. He was able to balance that with also holding his standards high. It was also nice to be on a team where humor was appreciated.

    One of my favorite conversations, well into the three years I worked for him, was when he asked me why something was the way it was on one of my assignments. I said to him, “Well, the most likely explanation is that I am an idiot.” He said, “Join the club, I am the president.”

    Granted, it took us time to work up to this relationship, and for about the first six months that I worked with him, I don’t recall him making any self depricating jokes, but he always had an underlying humility balanced with his self confidence that really made him a great manager.

    1. Goldenrod*

      Aahahhahahha! First of all, I love your name, “Miss Chanandler Bong.” :p

      Your anecdote reminds me of one of my favorite jokes from Seinfeld. George tells Jerry that he needs help – he locked his keys in his car. Jerry says, “What?? How?” and George says, “How? I’ll tell you how. I’m an idiot, that’s how!”

  12. The Coolest Clown Around*

    An alternative if you’re concerned about too much self-depreciating humor: self-aggrandizing humor. As long as it’s super clear your kidding and you have the confidence to pull it off, it can still break the ice without you having to worry about depreciating qualities other people might share/be offended by.

    1. Silver Robin*

      That feels even riskier to me. Which is worse: a boss who thinks they are God’s gift to the world or the boss who is keenly aware that they have limitations? They can both be uncomfortable but I feel like the overconfident one can land way way worse when coming from a position of power.

      1. Clare*

        It can be done safely if you’re normally reasonably humble and you stick to work-irrelevant things. For example, if you have a notoriously cranky coffee machine: “Wow, I just got the coffee machine to work properly! Feel free to come and bask in the glory of a genius, everyone!”. Of course, as you say, you run the risk of being thought big-headed – but if your humour is usually self-deprecating then it’s not a huge risk to mix it up occasionally.

        As with all humour, it needs to be clearly absurd to all parties in order to be funny.

        1. Silver Robin*

          keeping it not work related is good! and yes, keeping it obviously absurd helps a lot, though some folks have a much higher threshold for what is considered absurd XD

  13. The House of No Mirth*

    My current manager uses a lot of humor, and I find it supremely annoying. They said something along the lines of, “I’m just a clown and want everyone to be happy.”

    In practice this means they’ll spend time chit-chatting and almost never discuss work issues. They use a lot of sarcasm too, which makes it difficult to talk to them about anything business related.

    With “humorous” managers, I’ve often felt it essentially becomes a requirement of the job to be their friend/buddy and laugh at their jokes. For me that’s a draining requirement, and having a good relationship with my managers doesn’t need to be based on being to joke around with them.

    1. Lady_Lessa*

      I first started thinking about your statement when I read something similar in a Robert Heinlein book. And am forced to agree. Perhaps not always cruelty, but definitely bad (like death)

    2. Lenora Rose*

      In discussion of how to have humour that doesn’t attack someone, the other most common version of humour is *surprise*. Someone did an unexpected thing, or started down what looked like a common path and veered.

      (another part is capping a quote in an unusual way, but this depends on knowing the original quote and the cap, and gets into pop culture ref territory quickly, which is awkward for the person without the references)

      1. socks*

        Yeah, in my day-to-day the “unexpected turn” form of humor is way more common than humor that’s based in cruelty.

      3. Silver Robin*

        I feel like puns and wordplay fall under this too, using words in an unexpected way that turns out silly

    4. Clare*

      People laugh at the absurd. Breaking social taboos is a cheap way of finding something many people find absurd. Hence, cruel humour. Higher wit is often context-dependent, since it relies on finding absurdity in a topic that all those present have a similar understanding of. Not everyone will laugh if I say I’m working on inventing the world’s first write-only memory, so such jokes feel uncommon – but that’s because we only usually hear the subset we have context for, whereas we’re all subjected to taboo breaking because the assumption is we’ll get it.

      In my experience, US humour is particularly heavy on cruelty and aggression, perhaps because it’s such a multicultural society and it’s hard to find shared topics? I’m not sure. But you don’t have to avoid wit to avoid cruelty, by any means. Searching ‘your hobby’ + ‘jokes’ can be a good place to start if you’re looking for humour without the nastiness. Unless your hobby is bullying of course, in which case I can’t help you.

      (That was a joke, I’m 100% certain bullying isn’t your hobby)

      1. Lady_Lessa*

        I know that when I took a college Latin course on Roman comedians, the slapstick/word play was still funny, but the political humor wasn’t.

  15. anon_s*

    Self-deprecating jokes seem harmless but they can just be awkward, tbh, and reveal your own insecurities in a way that does undermine your leadership. While I don’t think there needs to be a sharp divide between leadership/management and direct reports, there is a line between “my manager is personable, understanding, someone I can talk to, and even go to a happy hour with” vs “my manager is my peer.” We’re all adults, but when you’re in a hire/fire position talking to someone you can hire/fire, some seemingly harmless ‘jokes’ just don’t land for a lot of reasons others have described.

    Miss Chanandler Bong’s comment is a great example of when it would really work and when it’d also be a way to humanize, have fun, and comfort an employee.

    1. Smithy*

      To the point about revealing an insecurity, I do think that as a manager being able to sit in a certain level of sincerity is just necessary. Over time, you’re likely to have direct reports tell you varying degrees of good, bad, awkward, complicated and ugly news where being able to sit in a sincere response can be helpful.

      I’m not saying that the OP has been preparing to respond to news like a team member’s parent is sick or an important deadline was missed with a quippy remark. However, I also know that in tense moments there can be an impulse to add something to a phrase like “I’m so sorry to hear that” to lighten the mood. So not having humor always be a default can be a good practice to prevent Chandler Bing snarky quips where it’s not what your direct report wants.

    1. Jewelz*

      I humbly disagree, it’s not a terribly interesting question because there’s a pretty clear answer. Having a sense of work-appropriate humor is completely independent from competence as a manager or trainer which is what really matters.

      1. The Unspeakable Queen Lisa*

        I’m always amused by people who claim a topic is boring or not worth their time, but then take time to search for a comment to respond to indicating their disdain.

        It *so* uninteresting, let me tell you why…

  17. Frankensteen*

    The worst manager I ever had was the office clown before he was promoted. In fact, I think his being the office clown was in part the REASON he was promoted. His continuing attempts at being goofy and funny made his poor management even worse, it went from fun to oppressive, and he became increasingly panicked as the stuff people used to find endearing was now irritating.

    Managers can absolutely use humor well, but it has to come as a complement to their good management techniques. If those are lacking, humor is not going to help,.

  18. Fullaboti*

    Ooooof, this is a question I needed earlier in my career. I thought I was closer to a coworker than I was so when I teased them about something I inadvertently hurt their feelings. Luckily I wasn’t their manager but our relationship was strained after that. I’ve been working on my communication skills at work ever since but sometimes its hard for me to pick up social cues.

  19. Ms. Chaos*

    My former assistant principal once referred to me as the OG of SpEd at our school, then I’ve had to tell new people that I’ve made every mistake in the book… at LEAST twice… to let them know there’s nothing we can’t fix and that we are not invincible. So while that is technically self-deprecating, I can tell it often put people at ease when they are brand new working with someone who’s been in this game for decades.

    1. The Taking of Official Notice*

      I don’t find that self-deprecating—I find that approach to be acknowledging that we’re all human. It’s relatable and honest in a good-yet-professional way.

  20. Prefer my pets*

    One other caution about humor at work…please don’t let your initial response to a question be a joke & avoid deadpan jokes where there is even a nanosecond of question that you might be serious. I worked with someone we all avoided asking questions of at all cost because the frustration of having to wade through the joke, the joke responses delivered deadpan that then we had to figure out if were serious, etc was rarely worth the information, even if it took 3 times as long and went outside our official “chain” to get the answer elsewhere.

    I still hate that guy.

    1. Generic Name*

      I bet he has “fluent in sarcasm” on his online dating profile. I always swiped left on those guys.

  21. Two Dog Night*

    I didn’t think of this for the recent call for updates, but I’d love to know whether the employee at the no-humor office is still there….

      1. Two Dog Night*

        I only saw the one update, where they’d been there about 9 months and were planning to stay another year-ish, IIRC.

  22. Banananaan*

    I cut back on self-deprecating humor when I read that it has “splash-damage”. When you put down yourself, you may also be putting down people’s faith in you and casting doubt on their ability to accurately assess someone’s characteristics. Also, I noticed that I would use it to minimize my accomplishments or success to make other people feel better, even when I didn’t believe myself that whatever I had done was “no big deal”.

    Can confirm what Alison said: Sharing a funny time when I’ve flopped when someone is beating themselves up helps them feel less bad about themselves and seems like the best time to use this kind of humor.

  23. Audrey*

    Self deprecating can be so great when done well! I love this quote from John Maxwell:
    “Want to impress others? Talk about your successes. Want to impact others? Talk about your failures.”
    I think Alison is spot on with the advice, AND, op, sounds like you’re being a great manager.

  24. Generic Name*

    I just came from a company where work-inappropriate humor was rampant, and (at least in my opinion) contributed towards a hostile work environment. Upper management seemed to treat company meetings as their own personal stage to get laughs, and looking back, it was very unprofessional. Young men took their cues from the male leadership. Male company leader makes poop jokes, so male junior analyst thinks it’s a good idea to tell sex jokes. It was so not okay, and I’m still decompressing from that kind of atmosphere.

    So make sure that the nature and amount of humor you are using doesn’t open the door for problematic behavior, even if your humor is just on this side of the line. I’m not saying that is what you’re doing, but it’s definitely something to be aware of. Another thing I’ve noticed is when managers try to be funny during meetings, it can derail a meeting. Snarky or snide asides during meetings just isn’t something that managers (well anyone really, but especially managers) should be doing.

    And I’ll echo Alison’s comment on sarcasm. I have basically no tolerance for it anymore. Too often, sarcasm is really just meanness disguised as a joke. In my opinion, it has no place at work. If you MUST be sarcastic, save it for friends and family.

  25. Coin_Operated*

    One of the receptionists I managed was in our CRM and couldn’t find an email for one of our customers. I looked it up, and it was right there where they all are normally, she was just having a “moment.” I told her a story about after I had moved into my new house, and on the first night I was trying to plug a power strip into an extension chord, and it just wasn’t working. I was holding the prong side of the power strip backward so they weren’t even going into the plug in the extension chord. We had a chuckle after that.

  26. Delphine*

    Honestly, I’d say that as a manager you should avoid self-deprecating humor except in the rarest circumstances. People need to be able to trust your skills and self-deprecating humor often gives the humorist less of an air of authority and leadership.

  27. Jo-El*

    Fact is there is no good answer. And every day at work is a tight rope you’ll have to walk. I also use humor a lot at work, I figure if I’m gonna be with these people more than I am with my family I need to enjoy myself as much as I can.
    Here’s my advice, from the start I told them that “while I may not take myself seriously, I do take the job we do VERY seriously” and I’ve tried my best to live up to that daily and so far after 5 years no problems. Hope something like this works for you as well.

  28. Mononoke Hime*

    In some situations where stakes are high and emotions run rampant (e.g. emergency response), making self-depreciating jokes, especially coming from a leader/manager, would erode people’s trust and confidence in them. There are other ways to demonstrate humility and relate to people – one can be honest and direct and also show empathy without the humor element.

  29. Jam on Toast*

    I’m naturally irreverent and I like to laugh. However, I work in a field where many people take themselves, and their intelligence and their credentials, very VERY seriously (why yes, it is higher ed, thank you for asking!). There’s a lot of gatekeeping here, as though intellectual rigour and humour are fundamentally incompatible, which has always bewildered me. When people ask about my approach, I always say “I take my work seriously but I try not to take myself too seriously!” Honestly, I couldn’t do the work I do if I had to be serious every single moment of every single day. It would suck the joy out of everything. It also makes the times when I do approach things seriously more impactful because it underlines the difference from my normal, default setting.

  30. English Teacher*

    Another thing to keep in mind with any kind of humor is whether the listener is 100% guaranteed to understand what you’re really saying. Clarity should be the priority over humor in most work conversations. I speak from awkward experience. Some people just don’t have the ear for humor, and will just be puzzled, take sarcasm for sincerity, or not follow a joke’s train of logic. And if the language you’re speaking in is not their first language, they’re going to be at a real disadvantage. You want to avoid that confusion, not only out of consideration for them, but because explaining a joke is the worst thing to have to do.

  31. Jade*

    A little humor can be good and a lot is not. I’d question a manager who wigged out over a small mistake even if they were jokey about it.

  32. William*

    Timing, timing, timing, everything is timing. Not a manager story exactly, but yesterday I was in court for a murder sentencing, and the judge, in explaining why he was imposing a mandatory minimum sentence, somehow decided that was the right time to crack a college football joke.

    He did not get a laugh from the courtroom.

    1. Goldenrod*

      Jesus. Read the room, buddy!

      I don’t understand how people like that get to be judges in the first place.

  33. Thunder Kitten*

    As a 5’2″ petite (brown skinned) woman with an exceptionally young face and a high pitched voice working in a (older) (white) male dominated environment, I literally could not afford to have a sense of humor.

    People’s lives literally depended on me being taken seriously when I had something important to say. Manager or not, one’s ability to make jokes is also about one’s Identity and the privileges or lack there of that it affords you.

    1. Peanut Hamper*

      Agreed. Humor (or the perception thereof) often very much depends upon whether or not you are in or out of the group with which you are joking.

      These things are very situational. People who are looking for guidelines that will work in all situations are going to be disappointed.

  34. Goldenrod*

    I think a positive attitude and certain “lightness” of demeanor are very good attributes in a boss.

    Being a clown or telling inappropriate jokes – no. But being light about mistakes that aren’t serious, generally being willing to laugh about things, a willingness to admit imperfection, when appropriate – these are all great.

  35. The Taking of Official Notice*

    I find it obnoxious when coworkers use the same self-deprecating language repeatedly. Once or twice, fine. But don’t keep bringing that vibe into work. It’s unpleasant/uncomfortable to be around.

    1. amoeba*

      Eh, I mean, I think that really depends on the level/definition of self-deprecating. From the LW’s letter and comments, I got the feeling that it was really more in the “not taking yourself too seriously” and “being able to laugh about yourself” vein, which I actually think is great and I really like that in… well everybody, but also definitely my boss!

      Actually putting yourself down or unloading your self-hate upon your colleagues is a very different thing, of course.

  36. Amber Rose*

    My job involves a lot of troubleshooting, and often the simple act of my arrival in someone’s office causes the problem to vanish into thin air. I find it helps to joke about how I should clone myself so I can hang out in everyone’s office and then we’d have no problems, because people often feel so bad about me showing up only for there to be nothing I can do.

    So what I’m getting from that and a lot of these posts is that a little self deprecating humor to cheer someone up during or following a minor problem, that’s appreciated. If you’re constantly putting yourself down for laughs regardless of context, that would be wearing, and if you’re cracking jokes during a critical incident when the priority should be action, that would be undermining your authority.

  37. mimi*

    Allison’s second point regarding joking about the other person is so important. I deal with a lot of chronic pain that has me on FMLA and some work restrictions, and I occasionally make self-deprecating jokes about it* (usually when I have to ask someone to do something for me). My boss, who I am pretty friendly with, started making similar jokes to me. Eventually I had to speak with her, because, like, it’s not *actually* a funny thing to me, it’s a massive burden that I wish I didn’t have to deal with. To her credit, she was mortified and stopped immediately.

    *I’ve also experienced going way too dark and landing in the “this has made everyone uncomfortable” zone,

  38. Awkwardness*

    Ooooh. Such a good question and such a nuanced answer.
    It will take some time to let it fully sink in.

  39. Janeric*

    I recently saw a panel of very senior staff at work — and the head of the large government agency made about a half dozen jokes that miiiight read as friendly banter in most circumstances, but all his senior staff looked taken aback or worried by the jokes at their expense. It was an interesting insight into their dynamic.

  40. Hosta*

    I naturally have a pretty dark and wry sense of humor. A friend recently described a joke as “hilarious, dark but hilarious”. At work I save that for after we’ve really gelled as a team. The number one thing your report wants to know is that you are going to support their career. That means they need to know you are confident in yourself and in their work (as appropriate). They need to know you are reliable and fair.

    That doesn’t mean you need to be serious business all the time, you should totally smile, you can make small jokes, etc. But save a lot of the joking for once you have established trust.

  41. OP*

    Hello everyone, I’m the writer of this question. Thank you so much to Alison for responding to my question, and the commenters for offering examples of how humor can both be done well and those that related stories of jokes being taken too far.

    As an example of the humor I am using, while walking my report through a small mistake they made I related how I had made the exact same mistake when I first started out, was sweating buckets thinking I had caused a Big Problem, then upon going to my manager discovered that since we caught it immediately it was a 15 second fix. I wanted to illustrate that even if it seems like an issue will be a big deal that it’s not, as long as it’s corrected properly in a timely fashion. I also had a big yawn during some training, then explained to them that I was a bit tired because my cat woke me up at 2 AM screaming in my face that his food dish was only half full, and if I didn’t feed him right this moment he’d surely starve to death.

    The previous person in their position didn’t just make mistakes, but covered them up, then compounded those errors with more incorrect work to the point that 2 years later we’re still dealing with the fallout. My biggest concern coming in was emphasizing to my employee that small mistakes aren’t just ok, they’re expected, and making sure they feel comfortable coming to me with any errors or issues and we’ll get them corrected together.

    I want to thank you all again for the kind advice, and will ensure to use self-deprecating humor sparingly and to be mindful that any jokes or puns are kind and don’t detract from work. As the lead accountant you can a-count on that. :)

    1. Leaf*

      I love what you said about wanting to express that it’s most important to bring up issues to get them corrected together! I’ve only had a manager like that once and it has made a world of difference. I would appreciate as an employee if my manager just said that right out to me, whether or not jokes were included. I’m so glad this community was able to productively answer your question!

    2. Silver Robin*

      ah yes, the deep drama of cats whose food bowls are even but a gram off from their preferred fullness XD

      Those sound like perfectly good jokes, and they fall exactly in line with what I think most folks here were suggesting. Carry on! (but be careful about carrying ones… :p)

    3. MiloSpiral*

      OP, thank you for asking this question! I resonated so much with it. You sound like a very kind and personable manager, and the fact that you are asking this question shows you are self-aware and thoughtful too. I also like how you framed small mistakes as things to work on together.

  42. Leaf*

    I really like Alison’s note about being careful of quantity of self-deprecation, I also want to suggest being thoughtful of making fun of yourself for a mistake someone else might make later, if that makes sense. For example, how you talk about yourself making Mistake A is how I will assume you would think about or even talk about me if I were to make Mistake A later on. This may not be true, but it may feel that way for a newer or more anxious employee. Especially if you target yourself with words or phrases that aren’t particularly harmful to you but might be microaggressions if targeted at someone else.

  43. Peanut Hamper*

    I think humor at work depends a lot on the consequences.

    I don’t mind it if my boss jokes about his being incompetent at something rather inconsequential (not being able to cook), rather than something consequential (not approving time cards in a timely fashion).

    Likewise, I don’t think my boss minds if I drop a joke in the department chat about something inconsequential (we do love our cat memes; chemistry cat is a favorite), but if I made a joke about failing to meet a client deliverable, that would not be received well.

  44. Captain dddd-cccc-ddWdd*

    I’ve come across this both as the person reporting to the manager, and as the manager or colleague making the jokes.

    Reporting to the manager – he did come off as incompetent anyway, which was objectively true, but the use of humour made it worse. He didn’t know what to do in any given situation (the only reason the situation had reached him was because I or someone else didn’t know how to proceed or didn’t have the authority to handle it ourself, so it was a genuine escalation) and would respond with silly comments like “Delete all of it! HAHAHAHA” in response to an escalation about a number that seemed incorrect in a regulatory report… No one had any confidence in him and we were all relieved when he was “made redundant” and given a payoff as a face saving move instead of sacking him.

    As the person using humour – I do this a lot, but often the butt of my jokes is a faceless entity rather than myself or the other person. So I will joke about bad recruiters, the idiot at the software company who allowed the software to be released with this obvious deficiency, etc. Sometimes I make self deprecating jokes and pull them off, but I am quite confident (and perhaps arrogant!) normally… I do have a “silly switch” and have the ability to flip from joking around to serious instantly, like if we have a high severity incident (part of what my team does is escalations of customer incidents). I do try to maintain a sense of good humour even in fraught situations though, not necessarily cracking jokes but keeping things moving in a friendly manner. It does work as I get on with pretty much everyone, even those who are known by reputation to be “difficult”. I have 2 work ‘nemeses’ who would say I’m on good terms with them…

  45. DinoZebra*

    I love a bit if self-deprecating humour (I’m British that and sarcasm are our main forms of humour). But please don’t make jokes about “the thickness of your glasses” – modelling ableism – even/especially internalised ableism – to your subordinates is very much not what a manager should be doing.
    Even if it’s a light-hearted coping mechanism for you there’s a risk of making your audience feel awkward and ashamed about their own assistive tech.

  46. Ellis Bell*

    We just had some all-school training from a retired headteacher who was very funny, and I remember thinking that the humour was pretty clever and deliberate and that he probably had been a really great boss at his school. He was particularly keen that we compliment students more, and led by example during the training, but did so in a way that was funny, and didn’t have any of that awkward-singled-out-for-praise element. One example was he said to one teacher “I saw you all over this school today – you had your skates on! If you didn’t go there it wasn’t worth going to!” Another teacher was praised for his demeanour and was christened “Happy Jack” while he didn’t use humour, but spoke more straightforwardly when he made a similar compliment to someone he hadn’t met yet: “Thank you for speaking up, I love your cheerful energy.” There was some deprecating humour of hypothetical non existent teachers/the teacher we could be without watching our mood: “No one was ever inspired by a lemon lip”. One thing that made it work was that some of these lines were obviously prepared or thought up during the day, rather than risking a badly landed joke by going in off the cuff.

  47. A Good Egg*

    I recommend the book Humor, Seriously by Aaker & Bagdonas. My main takeaway from that book was that office humor needs to be more deliberate.

  48. JaneDough(not)*

    “Typically in the past I’ve built relationships with coworkers and managers with work-appropriate humor and puns, with a decent amount of my jokes being self-deprecating.”

    LW, is it possible that you’re over-relying on humor, esp. self-deprecating humor, bc you see your “regular” self (non-joke-cracking self) as insufficiently likeable? That, at some level, you believe that in order to be liked, you have to either show yourself as not a threat (“I’m a bit foolish / a nerd /a dork”) or entertain people?

    I think it could be very useful to pull back on the humor and simply be cordial / pleasant on some of the occasions when you feel the urge to crack a joke. Take the risk of feeling uncomfortable as you make that change, and in so doing add one more relationship-building tool to your toolbox — which will boost your confidence, which could lead to other positive changes. (I’m not suggesting that you need to change in lots of ways — but if it’s true that you feel insufficiently likeable as you are, then, yes, I’d say that some confidence-building and self-acceptance would serve you well.) Best wishes.

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