my employee keeps challenging my expertise

by Alison Green on March 28, 2023

A reader writes:

I’m a manager at a small advertising start-up that has a very open and transparent culture. I actively encourage my team to challenge and disagree with me, but I’m having issues with one of them doing so in a way that I perceive as disrespectful. He frequently disagrees with me, which is fine, but he does so in a way that I think challenges my authority.

For example, if I explain a standard procedure that we’ve agreed upon and done in the past that he doesn’t remember, he’ll bluntly state, “No, we’ve never done it that way” in front of the rest of the team. This sometimes leads to us going back and forth about whether or not a fact is a fact, even when I have documentation that proves I am correct, because he can’t accept the possibility that he might be wrong.

So far, I’ve mostly been trying to ignore him when he does this: to briefly explain the facts and reference the documentation and move on, rather than to sink to his level and have it escalate to me reprimanding him. I’m not sure at what point this calls for some kind of intervention, though. Does it make me look weaker to ask him to disagree with me more respectfully in front of the rest of the team? And how do I ask him to cut it out without also discouraging the rest of the team from being open with me?

I answer this question — and three others — over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

Other questions I’m answering there today include:

  • Employee keeping using astrology to analyze coworkers
  • Well-meaning people keep offering me condolences … and it’s a lot
  • How to encourage someone you’re rejecting
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{ 116 comments }

{ 116 comments… read them below }

  1. many bells down*

    I think my spouse hired this guy last year. Everything everyone else did was wrong, but the one time a woman dared to tell him that HE was incorrect about something, he freaked out about it for literally 3 weeks. Brought it up in every meeting. HR tried to force HER to apologize.

    They ended up putting the guy on a PIP and 15 minutes after that meeting, he quit.

      2. I went to school with only 1 Jennifer*

        I recently read (well, listened to) an excellent series about a Super-Hero Industry, and one of the characters was called Inspector Well Actually. (He really was a well-meaning guy, it’s just that he didn’t know he knew something until someone else made a positive statement that was incorrect. And then we learned that he could, eg, feel the air movements someone made from a block away, and that’s how he knew stuff. But he *still* couldn’t access the knowledge until someone else was wrong.)

        1. Robert in SF*

          Can you please post the source of that series (podcast? audiobook?)? I would love to check it out!

          1. GoryDetails*

            I think that’d be “Andrea Vernon and the Corporation for UltraHuman Protection” by Alexander C. Kane – quite entertaining!

            1. MCMonkeyBean*

              Gonna add a note here for anyone else who just went looking for it like I did that it is apparently an Audible Original.

          2. I went to school with only 1 Jennifer*

            GoryDetails is right. It’s a book series (3 books) and the first one is called “Andrea Vernon and the Corporation for UltraHuman Protection”, and they’re by Alexander C. Kane. I’m sure the books are plenty funny on their own, but Bahni Turpin narrated them and she is SO GOOD. (One character is based on a dinosaur, and of course we all know that they were birds, so that character clucks gently like a chicken when she’s mulling thoughts over. And Turpin nails it. That’s *exactly* what a thoughtful chicken-beast would sound like.)

            (Also: same author did Orlando People and you should read it too.)

        2. Robert in SF*

          Can you please post the source of that series (podcast? audiobook?)? I would love to check it out!

        3. Robert in SF*

          Can you please post the source of that series (podcast? audiobook?)? I would love to check it out!

        4. Robert in SF*

          Can you please post the source of that series (podcast? audiobook?)? I would love to check it out!

        5. Robert in SF*

          Can you please post the source of that series (podcast? audiobook?)? I would love to check it out!

  2. Dust Bunny*

    if I explain a standard procedure that we’ve agreed upon and done in the past that he doesn’t remember, he’ll bluntly state, “No, we’ve never done it that way” in front of the rest of the team. This sometimes leads to us going back and forth about whether or not a fact is a fact, even when I have documentation that proves I am correct, because he can’t accept the possibility that he might be wrong.

    I would not be at all surprised if he remembers just fine but is using this to derail meetings and make you look incompetent, OP. So, yes–stop dickering with him in meetings, in front of witnesses. I hope/assume that the rest of your team is astute enough not to be put off when you cut off what seem like obvious attempts to undermine you.

    1. Bee*

      I disagree – I don’t think he’s just making this up, I think he DOES forget and is absolutely unwilling to consider that he’s wrong even when confronted with proof, enough that he basically gaslights himself into believing this never happened. That’s a very common type of guy, probably much more so than someone who is willing to deliberately shatter their own credibility in order to undermine their manager. But also, yes, the rest of your team is most likely aware this guy is wrong, so they’re not going to think poorly of you for declining to debate basic facts. They’ll probably be glad meetings aren’t derailed by this anymore!

      1. Always a Corncob*

        This. What risks your reputation with the team is letting meetings be derailed by back-and-forth with their annoying coworker. Cutting off the behavior and confidently moving things along is a sign of good leadership, not weakness.

        1. Artemesia*

          THIS. It is important to shut this down firmly in the group not for the sake of this doofus but for the sake of how you appear to the team. Alison’s advice is good on that. A firm ‘this is what we will be continuing to do and I will discuss it with you one on one later’ is needed. Don’t ever let him derail a meeting like this again.

      2. ferrina*

        I’ve met this guy. It’s really, really hard to tell if he actually forgot and is refusing to backdown, or if he’s intentionally making stuff up. It’s probably all the same in his head.
        Totally agree that the rest of your team knows you are right. Luckily, LW is the boss and has all the standing (and responsibility) to address this. A simple “I’m not going to debate you right now, we’re going to move on with the meeting”. But I’d think long and hard if you actually want to work with this guy.

    2. H3llifIknow*

      This reminds me of a couple of guys I’ve worked with in the past. They’d constantly bring up all this negative stuff in meetings. Dire consequences, and whatnot, but nobody EVER noticed they had no solutions or data. So, people ended up deferring to them as “experts” and it was SOOOO frustrating, like “excuse me… how can you NOT SEE he is FULL OF s**t!?” They’d especially do it when I or another woman were briefing something. Oftentimes it wasn’t even on point with our topic, but was tangential enough to make everyone take a left turn and leave the presenter looking like an idiot because this wasn’t supposed to be part of the briefing! Aaagghhh so glad to be away from those nimrods.

  3. Me*

    Try being a teacher. My students, who are children, will often question my expertise about a subject I have a master’s degree in. It’s frustrating.

    1. Peanut Hamper*

      Are you sure they’re questioning your expertise, as opposed to the information you are presenting? Because, yeah, students should be asking a lot of questions about the subject matter. “How do we know that?” is an essential question in every field.

      If they are actually questioning your expertise, it’s possible that your teaching method that is causing them to do that.

      You shouldn’t be frustrated by students asking questions. That’s their job.

      1. Lab Lady*

        I think this is a case where we should believe the poster. I strongly suspect as a teacher they have experienced both kids of questioning the material and children who have decided to try to undermine the teacher. and are capable of telling the difference.

        Its totally fine to be frustrated when kids decide to disrupt the class room rather than learn, particularly when that attitude is supported by the parents.

        I’m not saying the teacher gives up on the students – they are kids after all, but the frustration at how little respect the US affords teachers is a fine and real thing to feel – and I applauded the teacher for staying the course while underpaid and underappreciated.

        (of course there are bad teachers too… but not most)

        1. Double A*

          I’m also a teacher, and in my view, even the questions that are trying to “undermine” the teacher are teaching moments. Just because they’re repeating talking points they heard at home doesn’t make that any less true. We can ask them to think about their own thinking. You can’t let it totally derail a class, but one way to show why you deserve respect for your knowledge is showing that you will think about other points of view and take time to explain their questions. These are qualities that you would like your students to learn, I hope — perspective taking and metacognition — so you need to model them.

          If the conversation is derailing the class too much, there are ways to manage that. A great one is to invite them to an after-school conversation on the topic. They will decline if they’re just stirring the pot, but if they’re genuinely curious then what a great conversation you can have with them!

          The amount of patience and instruction that go into teaching children how to cope with authority is (or at least should be) much more extensive than what one does for employees where one clear conversation should do it. Unfortunately, teachers don’t get a lot of training with this kind of thing, which can make it hard.

      2. Irish Teacher*

        Students should be asking questions about the topic, but not stuff like “well, that’s not what the teacher I had last year said” when it’s very likely they just misheard or are misremembering what the other teacher said, because what they are claiming they said is factually incorrect (and yes, teachers can be incorrect, but it is far more likely a student wasn’t listening than that a teacher was incorrect about pretty basic knowledge in their subject area).

        It happens a lot to subs who students often don’t realise have a degree in the subject and try to trip up with half-remembered information from their usual teacher. I’m talking things like the teacher is talking about the causes of World War I and a student says, “that’s not true. Mrs/Mr. Whoever told us Hitler started the World War!” “No, that was World War II. We’re talking about World War I.” “She did say it. You just don’t know. She’s a better teacher than you.”

        Sometimes it’s just a way of trying to kill time by getting the teacher arguing about something, sometimes it’s an attempt to get “back” at a teacher who has caught them out in some misdemeanour, to the point that they are trying to find something the teacher is wrong about so they can convince themselves the teacher’s correction of their behaviour can also be ignored. Sometimes it seems to be a response to a new teacher or sub teacher taking over from a teacher they liked and wanting to put down the new teacher because they object to them taking the place of a teacher they really liked. And well, the time I got it most frequently was early in my career when i was in my mid-20s and usually from the 15, 16, 17 year old boys, so I think there may have been a degree of sexism on occasion too.

        I don’t think many teachers are frustrated by students asking relevent questions, but asking questions that don’t even make sense in the hopes the teacher will say something they can giggle about after class or even just the questions students ask in an attempt to waste time and get the teacher off-topic…that’s different. And I think most teachers can tell the difference. We have a lot of experience of both.

      3. Bunny Lake Is Found*

        Eh, but sometimes a student can legitimately be challenging a teacher’s expertise and authority. I’m pretty sure I was that student at least once, actually.

        My 2nd grade teacher HATED me because I was constantly challenging her/correcting her. I have no reason to doubt her intelligence, but she was not quick on her feet and always got frustrated when she got “off script”. And I was that annoying kid who had read “Origin of the Species” and selected works of Gregor Mendel that was now being taught some watered down, inaccurate 2nd grade science curriculum involving life cycles and heredity. I had questions that my teacher couldn’t answer, information that she didn’t know, and a firm belief that, if I already knew more than the teacher, why exactly was I being forced to sit and pretend to learn? Mix in my being on the spectrum, I am 100% sure I challenged her expertise very directly and in front of students and parents.

        1. Buffy Rosenberg*

          On the other hand, it’s definitely the case that doing a lot of reading up on your own isn’t always the same as learning, being an actual expert, studying something formally or working in the field.

          I have come across people who think they’re correcting or questioning professional expertise and training because they’ve read about it but they’re… definitely not. They haven’t properly understood what they read, or they aren’t reading the most up to date research, or they’re not aware of specific nuances that come with experience, or any number of other things. It can be very awkward, you know they think they’re self taught experts yet to anyone who really knows the field, they’re really kind of embarrassing themselves. It can be harmless so you often just let them do it.

          Not saying you were doing that of course, and a kid in school is completely different from a professional context.

          But I do wonder if it is possible that you didn’t “know more than the teacher” in the way you think you did.

    2. Dust Bunny*

      I mean, at least they’re kids who don’t know yet how much they don’t know. This guy is an employed adult.

    3. Double A*

      I’m also a teacher. This seems appropriate, within limits (it can’t derail an entire class period). I want them to understand why they should respect my knowledge and how to appropriately challenge authority. I’m fine with demonstrating why I know something, or why we need to do something. What a great chance to teach about metacognition — how do THEY know the things they know? Or to teach about assessing sources for reliability — why SHOULD they trust you or anyone? I try to minimize the number of things I make students do that I can’t articulate a good reason for.

      1. ferrina*

        Seconding. I’m a little confused on why they are questioning the teacher’s credentials- I don’t think any of my students ever knew my credentials, and I only knew my teacher’s credentials in college.
        I love the metacognition moments. I’m a philosophy geek, so any student that asks”How do you know?” gets treated to an explanation of anthropology/the scientific method/scientific theory vs law/probability and usability/ways of studying subject X, and oh by the way, here’s where you can learn more, extra credit if you write me a paper on this field. They learn really quickly that it’s a terrible way to try to derail, but a great way to learn about different fields of study and career options.

      1. Fishsticks*

        Hell, it’s normal for kids to do at HOME. I have an eight year old who is the world’s foremost expert in everything, it turns out, and we eventually had to ask her to stop saying “well actually” to every single thing we said because her dad and I were struggling not to either die laughing or of a rage-induced aneurysm.

        1. Grandma*

          I had a 5 yr old who swore up and down that her teacher had told them that bison were extinct. I’m quite sure that’s not what her teacher said, but there was no convincing this child. When she was 9, she saw a group of bison at Yellowstone, alive and well and munching the grass. All she had to say was, “Oh.”

          1. The Architect*

            OK, I learned that bison had been hunted to extinction at some point in elementary school, and I was super confused when I started seeing news articles and whatnot about bison at some point post-elementary school.

        2. Kacihall*

          My 7 year old spent a decent chunk of the 12 hour drive to spring break along is what level specific pokemon evolve at our where he can find them in his game. then telling us we were wrong.

          my husband was about ready to turn around and ignore the Disney tickets we have already paid for.

      1. Tired but happy*

        I am still embarrassed about the time I was ABSOLUTELY CERTAIN THAT THE USA HAD 51 STATES (I am not american) and made an ass out of myself because I cannot remember numbers and I was SO SURE.

        I was in high school. I was so convinced. It was because my parents always said as a joke that the US had 52 states and they would alternate as Canada or Mexico as the state and my brain latched onto that VERY INCORRECT JOKE FACT.

        I am still devastated at past me.

        2. Boof*

          It’s ok. I once swore up and down that hanson was 2 girls and a boy, and that a certain prawn for pyros song went “snap my picture” and not.. something much more misogynistic. I was utterly convinced of both these things for a while as a teen.

        3. amoeba*

          Ah, that’s just because the UK is the 51st state of America! (And now I have the song stuck in my head…)

    6. Stripes*

      It is frustrating.
      To stick with the original letter, say the topic is how to turn in work. If a child says “I’ve always written my name in the right corner and turned it in to box 3 on the front table” and you try to say “no, actually, your name should be in the left corner and this goes in box 1” I can see how that’s frustrating. Most all teachers experience this, unfortunately, as it’s human nature (teaching procedures in the fall and then re-teaching after every major school break).
      I can also imagine, if you have a master’s in education/teaching, that it’s frustrating if a child tries to push back something absurd (“I can only learn when I am allowed to lay on my stomach on the floor”) and you try to explain why that’s not okay and how it’s worth sitting at a desk, or in a chair, or standing in the back, or whatever.
      Also. I am SURE it is frustrating (especially right now!! this week!!) as a teacher trying to share an opinion and seeing a bunch of people telling you how you need to do your job/learn how kids work/etc better. Hang in there, Me.

    7. H3llifIknow*

      I’m curious what the topic is. I have a Masters in Network Security, and I get questioned a LOT by younger people…. and honestly, they’re usually correct. Why? Because IT is constantly changing and evolving and what I learned 10 years ago is often out of date. I try to keep up with current tech and trends but sometimes I don’t have the most current info. If your field is something that evolves or is subjective, or has its relevance in context (think history, sociology, poli sci, anything IT related) I could see them questioning maybe the “current application” of what you’re teaching. If it’s like… Math, well math is math (except new common core Math which is hell).

    8. Pescadero*

      I had repeated experiences in elementary school of proving teachers wrong about subjects they were teaching.

      My favorite – the third grade teacher who thought closed cell styrofoam would get waterlogged and sink if left in a water overnight.

      1. Bunny Lake Is Found*

        Same. It was bad. I realize as an adult that this is because elementary school teachers have to teach such a range of subjects, it is nearly impossible for them to be universally strong/knowledgeable in all of them. Like, yeah, they have a masters, but in the actual work and craft of educating children and guiding their development, not in advance mathematics. No one teaching 3rd graders NEEDS advance calculus, but unfortunately you give a graphing calculator to the wrong kid and suddenly you’re being grilled on sine and cosine while thinking “Kid, I literally have not thought about those WORDS in 20 years, let alone remember what they mean”.

  4. Richard Hershberger*

    LW1 has a usenet idiot working for them. In my youth, poking at guys like this was my personal vice. I have (mostly) aged out of that nowadays. There was this one guy who could be led around in a circle to directly contradict himself. At that point he dropped any pretense of facts and logic and fell into simple abuse. Good times. He also was literally unemployable. No one would hire him for any job that he believed worthy of him, and he refused to take any job that was not. The kicker was that he was actually a pretty bright guy. My theory was that one day in his teens he noticed that he was the smartest guy in the room, and over-generalized from this to believing that he was the smartest guy in the room regardless of who else was in there.

    I guess my question in the case of the LW is what are the chances of this guy growing up, and whose responsibility is it to carry him over until that happy day? I suspect that having him in the office would be intolerable, both for the LW and the other employees.

    1. Keymaster of Gozer*

      I’ve worked with several men like this (and oh boy the usenet days – definitely encountered a lot of the arrogant know it all) and there seems to be two outcomes on being called on it:

      1. Person rants, insults everyone else, claims nobody is smarter than them and either gets fired or quits.

      2. Person stops, has a think about whether being right is worth alienating everyone they work with and becomes a lot quieter.

      Outcome 2 is rarer.

      1. Where’s the Orchestra?*

        The only time I saw outcome number two happen – it happened because being fired (after fair warning, including warning in writing they were required to sign) was such a shock to their system it knocked them completely out of their smug little comfort zone.

        I worked with them later at a different job and they really were a great teammate the second time around.

    2. Alan*

      I work at a place where almost everyone has an IQ well above 100. It’s full of PhDs and engineers, many of whom are experts in their fields. It’s difficult when you come in well-ranked from a good school and find that there are people smarter than you. Some people never quite make the transition, always insisting that they know better than everyone else, even in areas where they *clearly* lack both experience and book knowledge. Those people do not do well, and sometimes strike out. Their self-concept as “the smartest” is being crushed before their eyes.

      1. Mensa Maid*

        I am surprised that you know the IQ’s of your coworkers. Mine is well above 100 but I don’t announce it to people.

        1. Alan*

          Sorry, in retrospect this sounds like a flex and it wasn’t intended that way :-). I’ve just seen people who tried to push PhD-ed experts out of the way (and no, I’m not one) because they thought they knew better, and it never goes well. Sometimes they get it, but more often they think that they’re being underappreciated, that people around them are too dim to know how great they are. When I was younger I too thought I was hot stuff and every year that goes by I realize just a little more that I am not.

      2. Gracely*

        This is why I have a sign in my area that says “We’re all smart here. Distinguish yourself by being kind.”

        1. MM*

          If you don’t have a point to make, don’t sweat it
          You’ll make a sharp one being so kind
          And I’d sure appreciate it
          Everyone else’s goal’s to get big-headed
          Why should I follow that beat being that I’m
          Better than fine

          – Fiona Apple, “Better Than Fine”

      3. sam_i_am*

        It’s difficult when you come in well-ranked from a good school and find that there are people smarter than you.

        +1000. It’s such a harsh transition for a lot of people. It was for me, though I don’t necessarily know if the difference is intelligence so much as expertise. I work at a top-tier university with a lot of people who know their stuff better than I ever will, and I’ve had to learn to accept that. Quite frankly, I just don’t want or need to have their level of expertise because that’s what they’re there for!

      4. Pescadero*

        It is pretty common for PhD’s in engineering academia to believe that the fact they have a PhD means they’re in expert in EVERYTHING.

    3. ThursdaysGeek*

      It’s too bad when smart people are fools – they don’t realize that wisdom is more valuable than intelligence.

      1. ferrina*

        I’m always surprised when a smart person brags about being the smartest person in the room. I’m incredibly smart (got the numbers to prove it), but I’d rather be in the company of people more intelligent than me so I can learn from them. If you’re the smartest person in the room, you’re in the wrong room.

        1. ThursdaysGeek*

          Yeah, bragging about being smarter than others is just stupid (and rude). Plus, I’ve never met a person I couldn’t learn something from. No matter how smart or not smart they are, they still know things that I don’t.

        2. Bunny Lake Is Found*

          Or the right room. Dude, life is like a pot luck party. I DO usually bring the “biggest brain in the room” dish to the party, but the reason the party is awesome is because someone else brings the “Crazy stories from my job that I tell with the skill of a stand up comic” dish, another brings “are we all engaging enough in self care?”, another “I have an art show opening next week and everyone should come”, or “I shall now moderate the small scale debate on “where did the bread for that sandwich even come from?” in The Last of Us?” that has spontaneously broken out because, fun fact, I did Model UN in HS”, and so on.

          I have no desire to be in a room with only people smarter than me, it’s like a potluck party where everyone only brings whole bran muffins.

    4. Science KK*

      I have a relative like this. Everyone’s an idiot except for him, loves to brag about how he’s saved $500 (he has exactly one bill he pays, car insurance, the rest is all just fun stuff), told me I was wrong about the costs associated with moving to the high COL area I live in, and tells everyone he knows he’s looking for a job where he makes a lot of money not actually doing anything. Doesn’t understand why he can only keep his job at the pizza place.

    5. ThisisTodaysName*

      “There was this one guy who could be led around in a circle to directly contradict himself. ”
      This reminds me of one of the most beautiful examples of this I’ve ever seen. My son was in a debate, the topic was something along the lines of our involvement in foreign military actions based on US values. By the end of the debate my son had the other kid saying that the US should not have gotten involved in WWII and that Germany should have been left to continue exterminating Jewish people, he had gotten so twisted up in his own arguments. It was 20 years ago, so I wish I remembered it better, but at the time we were all blown away.

  5. Richard Hershberger*

    LW2: If I were one of those people your team was trying to build a relationship with, I would find this behavior very off-putting, to the point of declining to pursue that relationship.

      1. RJ*

        Totally agree. I believe in a lot of New Age thinking, but I also believe that no one way, path or system can explain everything and everyone.

      2. Ray Gillette*

        I’ve got a team member who jokes about Mercury being in retrograde every time something unexpected goes wrong. Then we all have a laugh and move on to working the problem. That’s about the level of astrology that I think is acceptable in the workplace, anything beyond that is a hard nope.

        1. Relentlessly Socratic*

          Don’t mess with Mercury Retrograde. It smells skepticism and will promptly trash your hard drive, data files, or delete all of your phone contacts.

    2. Dust Bunny*

      I am the biggest Cancerian stereotype in history but I still don’t want people locking me into that box. Also, this kind of thing is especially inappropriate at work.

      1. Queen of the Introverts*

        I felt this letter personally as someone who was pegged as a Capricorn by a high school friend’s mom 10 minutes after meeting here and remained in that box for the next four years.

        1. Queen Ruby*

          My BFF is a Capricorn, and she’s pretty awesome, so I’ll assume you are too!
          I’m on the Leo-Virgo cusp, which is a very weird combo, kind of contradictory. I have a friend who’s bday is the day after mine. As friends, we great. When we worked together, what a nightmare! He’s more Virgo and I’m more Leo.

      2. Peanut Hamper*

        This! I don’t believe in anything really, but if I found out that people were being locked into or locked out of opportunities because of something that is fairly arbitrary (I mean, nobody chooses the time or location of their birth) then I would be not good with that policy.

    3. Where’s the Orchestra?*

      It would be beyond off-putting to me – to the point I’d be investigating ways to NOT work with your report. Generalizations used to make decisions have never worked well in my experience, and I do not want to be labeled for what job I should do just because I’m a whatever sign.

    4. Cohort 1*

      When people ask about “my sign,” I often tell them I don’t know (not true) and I’m not into astrology (quite true). Anyone who takes it one step beyond that is totally socially oblivious. I’m not going to hand over my birthdate or in any way cooperate. As a last resort I might add that I’m just not interested in superstition, but that’s sort of obnoxious so I save it for the truly obtuse.

  6. learnedthehardway*

    OP#1 – In addition to Allison’s advice, you might also need to define for this person what you mean by “being open to people challenging your ideas”. ie. you’re open to people suggesting ways to improve upon processes and policies, but not arguing facts. And that you’re going to be making the final decision. Maybe a general lunch & learn about “How to challenge ideas professionally, constructively, and effectively” would be a good idea for your whole team. Idea being that challenging things should be for the sake of improvement of the overall business, not just to be right / show other people up / be argumentative, etc, etc.

    1. Peanut Hamper*

      not arguing facts

      Yep, this. This guy is veering dangerously close to “fake news!” territory.

      It’s okay to have your own opinion, but not your own reality.

    2. PollyQ*

      Maybe a general lunch & learn about “How to challenge ideas professionally, constructively, and effectively” would be a good idea for your whole team.

      Given that no one else on the team seems to be having trouble with this, I don’t see the benefit to making them all sit through training. Address the problem with the person who’s having the problem.

      1. Cyndi*

        I know personally, if I was one of this guy’s teammates and already frustrated that LW wasn’t shutting him down, a “general lunch and learn” would just compound my frustration with both of them.

        1. Fishsticks*

          I’ve seen “general statements” used repeatedly. I have never once seen them work.

          1. Cyndi*

            Personally I appreciate it for minor things, like if my manager drops a message in the Teams group chat that says “hey everyone, don’t forget to sign your teapots before you glaze them, not after.” But for any more substantial performance or behavioral issue–yeah, addressing it generally instead of with the one person actually having a problem is always going to backfire IME.

          2. Ultra Anon*

            General statements don’t work because often your target doesn’t have enough self awareness to realize you’re talking about them. The rest of your team will either roll their eyes or will think you’re talking about them when you’re not and they’ll spiral into self doubt (….not that I’ve been that team member).

    3. Relentlessly Socratic*

      The problem with a general response to a specific problem is that the person who needs the lunch and learn the most will not realize that this is specifically for his behaviour.

      1. Peanut Hamper*

        Yep. He’s just going to sit there and stew that he’s surrounded by idiots who need to learn this.

        I’ve sat next to people like this. It’s not fun.

        1. Where’s the Orchestra?*

          I had that person as a manager – I almost took a lateral to get away from them. Just as I was deciding between options they quit in a huff because they didn’t get a promotion they thought should have been theirs.

          No, we don’t miss them at all.

    4. Samwise*

      Don;t do that lunch and learn if Junior is the only one not getting it. He needs to be spoken to individually and directly.

      1. Where’s the Orchestra?*

        Or do a lunch and learn for Junior only. If he’s the only person in the room you can be really direct about what you do and do not want to see/hear from him.

  7. Michelle Smith*

    There are few things that make a rejection feel less painful than an interviewing genuinely and honestly conveying that it was a difficult decision, specifying what the deciding factor was that made you second choice rather than first, and encouraging you to apply again in the future. If it weren’t for people like that encouraging me, some very bad things would have happened to me as I lost hope during my last job search. Other things that really help when a person is a strong candidate but there are other stronger ones: offering to connect them with someone else you know is hiring for a position that might be a good fit! There’s no reason you can’t be a warm referral for someone you feel is really strong. I can say from personal experience that even when the person you’re referred to doesn’t reply or isn’t a good fit, just having someone feel confidently enough about your abilities to refer to you to someone else is a huge self-confidence boost in the face of so many rejections.

  8. Marketing Unicorn Ninja*

    LW 1: I would stop handling this guy with kid gloves like yesterday. Shut him down in the meetings, and then talk to him after and lay out the pattern for him.

    I don’t know if it makes you look weak exactly, but I guarantee you it’s driving your other employees bananapants. I have a colleague like this, and everyone dreads meetings with her because she is argumentative, combative, and claims she can’t remember what the procedure is even though we’ve had the same procedure for 10+ years. When she starts to speak, you can feel the whole room collectively groan and turn their attention to something else, and the meetings never get back on track after that.

    1. Turquoisecow*

      Yeah if I was another person in these meetings I’d be wondering why the boss didn’t tell this guy to knock it off. It would make me think op wasn’t a strong leader and that the guy was a jerk who was derailing meetings because he didn’t want to do any work. He’s like the misbehaving kid who derails the whole lesson for the rest of the class. I had no patience for that in high school, I definitely don’t as an adult. Shut it down.

      1. Palliser7*

        I fully agree. We have a couple of agressive over-talkers on my team, and my boss has no problem telling them to stop talking so that someone else can finish a point. It’s 100% a power play on the part of the employee and his teammates are relying on the boss to shut it down so they can avoid being held hostage to BS. I know that sounds harsh and mean, but the truth is that people who do this kind of thing are often so oblivious that they don’t take these sorts of reprimands as seriously as others. My boss often gives reprimands to the over-talkers on my team that would make me cry, but for them it’s the minimum about that makes them actually listen in the moment, and they are very far from being truly upset about it.

  9. takeachip*

    LW1, I don’t think you need to worry about discouraging others from being open with you by shutting this guy down. They can probably see the same pattern you do and may be equally frustrated with it. This employee is being disruptive and I would bet that the others can tell the difference between that type of behavior and the type of open communication you want in your meetings.

  10. VP of Monitoring Employees’ LinkedIn and Indeed Profiles*

    #2…

    “Unfortunately, your hobby really doesn’t have a place in a professional office.”

    1. MsM*

      I don’t think “hobby” is the right framing here. Given how seriously the person seems to take it, I’d be more inclined to compare it to forcing one’s religion on colleagues who don’t want to hear it.

      1. penny dreadful analyzer*

        As far as I am aware astrology is pretty squarely in the “spiritual beliefs” category, so I’d probably also take a “this is religion-adjacent enough to be inappropriate for work” tack.

        1. Reed Weird*

          Yeah, this is where I come down on it, as someone who uses astrology and tarot in my spiritual practice. I wouldn’t want my coworkers saying they’re hiring someone because they prayed about it, and I don’t want them saying they hired them because they’re a Sagittarius.

  11. Robert in SF*

    Can you please post the source of that series (podcast? audiobook?)? I would love to check it out!

  12. Honeygrim*

    I’m dealing with this right now. Instead of challenging my expertise by correcting me explicitly, this person is inundating me with “what ifs” and “what abouts,” like they’re trying to poke holes in any of my ideas or decisions. It definitely feels like they’re trying to undermine me, but I can’t figure out how to address it since it’s not as blatant as what Letter Writer #1 described.

    1. House On The Rock*

      I’ve worked with and managed people like this. Instead of even entertaining their speculation, turn it around and ask them the purpose of their questions. Force them to articulate why they think that exploring endless branching paths is a good use of your, or their time. They usually falter at this point and say something like “just curious” or “just think we should account for every possibility”. Then you can ask them why they think that, or whether satisfying their curiosity is the point of your work.

      The only caveat here is to keep it very focused on how their questions and explanations relate to the actual work at hand, and as soon as they’ve made clear it doesn’t, shut it down and move on. Otherwise they will think that Business Fan Fiction is a legit game to play.

      2. fgcommenter*

        “just think we should account for every possibility” is not faltering. It’s making sure you don’t push through a poorly analyzed idea that could have detrimental consequences. Either show how you have considered the possibilities, or show what contingencies you have in place to catch any fallout from unconsidered possibilities.

        1. New Jack Karyn*

          There’s accounting for possibilities and exploring knock-on effects. Then there’s chasing gnats. You can expect horses, and plan for zebras–but you’re not getting an African wild ass coming through the door.

          1. Don't Call Me Shirley*

            Does the gnat cause mild inconvenience, or mass death? What’s the expected deaths per year of the gnat? Does your existing mosquito netting manage the risk according to standards?

        2. Serin*

          1. The crucial word here is “every.”

          2. I think we can trust that the LW knows the difference between “I’d feel more comfortable with a Plan B because that person works in another time zone and is often unreachable” and “I’m feeling around for some special circumstance in which I’m right and you’re wrong.”

      3. Jam on Toast*

        “Well, we’ve always….” is a phrase I heard so often from one very entrenched and blandly vindictive co-worker that lived to oppose *anything* she didn’t personally approve of. To this day, I actually have to remind myself to breathe slowly and loosen my shoulders before I respond, even if it’s the first time another person says it in front of me. It’s PTKIAS…Post Traumatic Know it All Syndrome.

        1. Lizzo*

          “We’ve always done it that way.” = The most dangerous words in the English language.

    2. Filthy Vulgar Mercenary*

      Let them do one or two, don’t go too far down the road of why it’s not relevant (like one sentence), then say “okay, we are getting off track, we can meet offline to discuss any concerns you have.” Or “I don’t want to derail the meeting with the details of how we have addressed those concerns but we can meet later if you want to review” or “I don’t have time to go into those details but rest assured they’re handled/not a concern”.

    3. She of Many Hats*

      “We have considered many What If/Abouts during the planning stage. We won’t avoid every unwanted situation which why we’ve also planned for contingencies in case something should arise.”

    4. Clorinda*

      Make him do the work himself.
      On Friday around 3 pm you say “You can go ahead and write up all these possibilities and options, and have it on my desk by Monday morning. And on Monday morning, “thanks for the input” and circular file it. He can waste his own time as much as he likes, but he can’t waste yours.

      2. fgcommenter*

        On Friday around 3 pm you say “You can go ahead and write up all these possibilities and options, and have it on my desk by Monday morning.

        It would be better to say “have it emailed to me, and bcc a copy to your personal email”.

        Then when the boss tries to blame the fallout on the employee for “not being responsible enough to see the problem before mindlessly implementing it”, the employee has proof of attempt to address concerns.

      3. Grammar Penguin*

        If it’s a pointless work task that YOU assign to him then yes, that’s “your” time he’s wasting. You ARE going to pay him for that weekend assignment, yes?

        I’m pretty sure if my boss assigned me work on Friday with a deadline of Monday morning, they’d better f’ing pay me that overtime whether they use that work or toss it in the trash. I’d likely be job searching after that. Especially if the only purpose of the assignment was so my boss could *avoid* having a direct conversation about my performance.

        I’m pretty sure if a manager under me was handling a problem employee this way, I’d shut that down. Don’t assign random and pointless work (PAID work, right? RIGHT?) to send a message. Use your words like a grownup.

        If you’re just trying to “manage him out” (i.e. get him to quit on his own) rather than address the actual problem you’re having, this would be a good way to do that I guess. Seems like a lot just to avoid an awkward conversation.

        Maybe it’s the weather affecting my mood this morning but I’m just not seeing the benefit of suggesting petty revenge as a solution.

    5. Ultra Anon*

      Ugh, I feel this so hard. The endless what if, what about, what should we do when’s make decision making by committee the 10th level of hell.

  13. lost*

    LW 1 is very similar to a situation I was in. One of the commandments of where I work is thou shall seek continuous improvement. Unfortunately the person I was managing took this to mean: argue against every policy, even against upper management. I say was, they quit in a huff because the feedback they got from numerous people was “do your own work correctly before you tell your grandma how to suck eggs” (more professionally, natch)

  14. Good Enough For Government Work*

    LW2: Please, please, PLEASE shut that nonsense down.

    I loathe astrology and am frequently surrounded by true believers (I’m queer; it tends to go with the territory). Over the years, I’ve just about used up all my ability to be diplomatic about it and would have immense difficulty in not responding to this coworker’s enquiry about my sign with “I was born under the sign of someone who thinks this is bullsh*t.”

    (If it helps, I feel the same way – occasionally, stronger – about personality tests, Myers-Briggs and the like. Which I tend to refer to as “astrology for people in suits/people who think they’re too smart for astrology.”)

    Now, if you want to talk me about astroNOMY, I’m rubbish at the physics but I’ll be all ears…

  15. SB*

    LW1 – time for a one on one conversation about how to challenge ideas professionally & accept when he is wrong. If he cannot do that, PIP time.

  16. Sometimes you've just had enough*

    A friend of mine finally found a way to head off unwanted condolences. His dad was a big fish in our small town, and everyone that friend encountered wanted to eulogize him… so finally after months of this, friend started soliciting donations to the Big Fish Scholarship fund at a local university. People stopped repeatedly consoling Jr. Fish about the loss of Mr. Fish unless they wanted to get their wallets out.

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