my employee keeps working long hours even though I asked him to stop

A reader writes:

One of my employees who I manage is a very hard worker, reliable, and always gets the job done. He has a great reputation in the company, and everyone goes straight to him for help with projects (something that was the case when I started, and has been working well until recently).

But the last few months, he has been staying late and talking about it in a way that troubles me. I often hear him say things like, “I’m going to be here until 9:30 tonight so one more task won’t matter” or “I was here until 8:00 and it still isn’t done.”

As his manager, I felt obligated at the beginning to find out where these tasks were coming from and what I could take off his plate. Every time we met, we decided on a plan for reassigning something, or I would reach out to someone asking if a timeline could be pushed back, etc. Then, a day or so later he would be back to staying late. Just yesterday, he sent me a note that said, “Look at the time receipt on this email — I was here until 10:00 p.m.”

It’s frustrating when he flaunts his overtime because he’s not helping me do anything about it. We seem to have a plan and then it falls through. At this point, I’m feeling like he just wants me to feel guilty or bad for him. (He is not eligible to be paid overtime.)

I believe the problem is ineffective time and task management. He has a team he manages that does design work for the entire company, and sometimes requests come in that we need to say no to, or give a more realistic deadline for completion. He wants to please everyone, which is just not realistic for this type of work. Another problem is that this workload is inconsistent — sometimes we are bombarded with requests, other times it’s very slow.

I’ve tried continuously to ask how I can help, but I think the last resort would be to have all of his tasks come through me. I hate to rob him of his freedom to manage his own tasks, but part of my role (I believe) is to help him to manage his work in the confines of a 40-hour work week. Any advice?

I answer this question 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.

{ 200 comments… read them below }

  1. CatCat*

    I hope he’s not flaunting his late hours to his team. That could be setting them up to see that as some sort of expectation on them and making them feel guilty for not staying late. I’d be looking at the team’s hours too.

    1. stefanielaine*

      I was thinking the same thing – there are two parts to this issue, working long hours and boasting about working long hours. My work requires long hours sometimes but no one brags about it or points out time stamps. I don’t think you’ll solve the real issue here without figuring out what he’s getting out of constantly pointing out how late he works because *that* is why he’s resistant to LW’s attempts to cut down his workload.

      1. LL*

        Yup, I came here to say that – I think the employee is not so much ‘complaining’ about long hours (as Alison describes it in her response) as bragging about them, either because it makes them feel very essential, or because they want praise/recognition for being ‘so dedicated’. So no amount of workload management will fix this.

        1. i_am_eating_cheetos*

          This was my first thought too!! I can’t stand when coworkers do this, even though I 100% understand the impulse.

          1. clumsycharisma*

            I was given that advice early in my career. When here late, always send your manager an email so they can see what time you were working.
            I completely understand wanting to do that but I only ever do it when I actually have something they need to know.

            1. Devil Fish*

              I dunno, it can be important for managers to have a general sense of their team’s hours—either to reward them correctly instead of relying on who they’ve physically seen the most or to help them keep to their assigned schedules (whichever one tracks best with the office culture). This is even more important in a salaried environment if no one punches a clock and there’s minimal record keeping re: hours.

        2. annony*

          Yep. The most effective way to make that stop is to give the opposite reaction than they want. “Look at the time receipt on this email — I was here until 10:00 p.m.” should be met with “That really concerns me. We need to work more on your time and task management because I don’t want that to happen again.” Hopefully he will stop working so late, but at the very least he will stop bringing it to everyone’s attention.

          1. Trevor*

            Unless the issue is the workload. Do not assume your guy sucks, that fails both of you.
            I left a position where I was repeatedly harassed for working late, and the only identified problem was my time management…
            Except my manager and director used beliefs and feelings, rather than data to make this identification. They made me question my productivity and work ethic.
            But enough days validated my beliefs in my abilities. I ran the reports and processed it in my already late evenings. I proved that due to throughput I was performing twice the assessments as the next closest person and generating five times the referrals.
            Starting dream job on Monday, just left the report on (now former) manager’s desk, sans the 18 page diatribe I found cathartic to write. I could not leave without at least presenting that information to try to help the next person who takes my assignment.

            1. VeryAnon*

              Yes. I was constantly told to stop working late in one role, so I did. And because there was too much to do, balls were dropped and deadlines missed. They eventually realised one person couldn’t do the work of three but boy were they mad about it.

        3. AndersonDarling*

          Ugh! I worked with someone who loved to complain about working late to get sympathy from other people. But guess what? Turns out he would actually leave 5 minutes after the last employee left at 5:15.

          1. Trish*

            Yes. I had a direct report a while back who did not like her annual review. She decided to get “even” by going to my supervisor with a whole lot of inflated overtime hours. It was a long hot mess. The relevant part is that she was actually going out to the pubs for a few hours and then coming back to the office and clocking out.

        4. Landry*

          This employee is gunning for OP’S job. Whether he is successful depends on whether the company’s leadership values a long-hours culture.

      2. Librarian1*

        Yep, I agree that it’s bragging. I think the employee thinks that showing that he’s working long hours will improve his chances at a promotion or a raise, but that’s clearly not going to happen because that’s not the culture at this company. Or at least not with this manager.

      3. Emily K*

        Yep, I have an employee who has a version of this issue that doesn’t involve the boasting. I know she works a lot of long hours and I am pretty vigilant about monitoring her workload and giving her explicit and realistic deadlines, e.g., “If you can get to this today with your other work that’d be great, but if you would need to work late it’s not important enough to be worth that and you can just hold off til tomorrow.” Sometimes the job does require late hours so I always try to make clear to her that my intent is to never make her work late when it isn’t strictly required so that she doesn’t burn out and will have an easier time when it is.

        She still works a lot of evenings, even when I’ve told her something can wait, but she’s not pointing it out to me. When I’ve noticed her working late she’s told me she just prefers to do certain types of tasks at home in the evening. I give her a lot of flexibility with her daytime schedule so the late hours aren’t always long hours, and it seems to genuinely just be the time of day she’d prefer to work if we didn’t live in a 9-5 world. I continue to monitor to make sure she never feels like she’s painted herself into a corner by setting a precedent that’s unsustainable, but I’m also not going to push her too hard to work more standard hours when her position doesn’t require it and she seems to have worked out a schedule she likes without compromising her availability or responsiveness to others.

        1. Devil Fish*

          This seems completely different than the OP’s situation and it sounds like you’re handling it well. :)

    2. Artemesia*

      I’d also be looking at the team’s productivity and his management of the team. Is he working long hours because he can’t supervise and delegate and manage others?

      1. Baba Wawa*

        This was my first thought as well. Sounds like he either doesn’t know how to delegate work, or his team isn’t up to speed/task. Maybe they are hourly and he doesn’t have the budget to have them finish the projects? Maybe he isn’t happy with their work and doesn’t know how to give them critical feedback? Maybe he’s trying to let the OP know that he needs another employee but just hasn’t said it outright?

    3. Laurelma_01!*

      His being johnny-on-the-spot allows others to slack off and “not” manage their time, workload. They can wait until the last day, etc and dump it on him, when they should be developing the ability to manage their workload and time management. It also screws up the time frame of his, and yours’ deliverables.

      Once a company gets used to a shortened deliverable time frame because of his hours, it will increase the expectation of others of him, his team and as his supervisor.

      Is he doing all of the work so that his team doesn’t work OT?

    4. Phoenix Programmer*

      I can almost guarantee he is. In general folks who bemoan (eg brag) about long hours dont want to fix the problem. They want to be seen as hard working and irreplaceable (which OP has fallen into the trap of) rather than focusing on their flaws (usually terrible time management, slow at their work, terrible delegators, control freaks, etc.)

      No sympathy for these people but as a manager OP needs to follow Alison’s advice for sure.

  2. Stickler*

    Maybe he’s working late because of personal issues but framing them as professional? It might be worth discreetly digging into that, if possible.

    1. Snark*

      I am continually amazed at the number of commenters who think it’s any of a boss’ business to “dig into” personal issues, however discreetly.

      1. Stickler*

        If the employee is having personal problems, the boss might be able to point them to the EAP. What’s wrong with trying to figure out if there are other issues besides an unrealistic workload?

        1. Snark*

          Because that’s not the boss’s job, and knowing if there’s a personal issue doesn’t change how they need to move forward to address this performance issue.

      2. pentamom*

        Digging into a personal issue itself? No. Digging into *whether* there is something outside work driving this behavior, without getting into what it is, is certainly the boss’s business. Otherwise, OP is going to keep trying to solve a work issue that isn’t a work issue.

        1. Snark*

          OP does not need to solve any issue that is not a work issue. If he stops racking up overtime, that’s where her interest in this stops. She has no standing to pry into his personal life, particularly when doing so would not actually change the approach Alison suggests. And she can solve the work issue without addressing the personal issue.

          1. Devil Fish*

            Hard agree. Depending on her relationship with the employee, it could be worth addressing the problem bluntly by asking “Why does the overtime keep happening even though we’ve agreed on ways to make it stop? What’s your goal here?” (I’m admittedly not great at interacting with humans so I’ve legit asked coworkers very similar questions when they moan about the string of bad luck resulting from things that are very within their own control) but that’s not an excuse to go digging through personal stuff.

            Further: Do not start a conversation about a personal stuff and then abruptly 180 like it’s the employee’s fault for bringing it up when you asked! (Hat-tip to the manager 10 years ago that noticed I was having an off-day and asked “if there’s something going on at home” and then physically recoiled in horror when I broke down and started sobbing about my impending divorce. Thanks, Steve! V helpful!)

      1. Safely Retired*

        Staying late to avoid going home to problems was exactly my first thought. Close to that, but not quite the same, is staying because you have no other life, going home to nothing. If the only meaning in your life comes from work…
        Neither of which is directly addressable by management. Only the behavior of staying is addressable.

      2. juliebulie*

        I thought so at first too, but in that case I don’t think he’d make a point of letting the boss know how late he stayed.

        1. Safely Retired*

          Just because staying late is to avoid going home does not mean they would themselves believe that to be their reason. We pretend to be rational beings, but when it comes to that sort of thing we are rationalizing beings. So blaming the long hours on the work load would happen regardless, and be as honest a reason as they can admit to themselves.

    2. KimberlyR*

      But he’s still letting other teams give unrealistic projects or timelines, just because he doesn’t want to go home (if that is the issue.) The teams giving them projects will come to expect this as the norm and get upset if Employee changes how he does things (or burns out or quits or whatever) or if other team members cannot perform to this expectation. As a whole, this team should hold their projects to reasonable timelines and reasonable expectations, regardless of one individual’s desire to work late (if that is indeed the case, which we don’t know.)

      Frankly, he sounds like the martyr type. He wants to flaunt how late he works and how much he gives to the team and how much they take advantage of him. But he doesn’t want to solve the issue because he won’t get to be a martyr. I could be off base but it would be telling if the OP held the Employee to Alison’s advice and he still tried to find ways to work late and brag about it.

      1. Elizabeth West*

        That was my suspicion too. A martyr will resist anything that doesn’t let them play that role, and the OP already said she tried to talk to him about what could help. If a non-martyr were inundated with work to the point they had to stay late almost every night, they’d jump at anything that would fix it.

        Of course, he could also be overwhelmed and sending the messages as a passive-aggressive way to say “Help, I’m drowning over here,” which validates Alison’s suggestion to check the workload. We’ve seen a lot of OPs who are afraid to say anything when they’re in a situation.

    3. Coverage Associate*

      I often stay late because the rush hour commute is so awful, or because I have a late personal appointment near the office, but I try to be really up front with coworkers about my reasons.

        1. tired*

          No, but this comments section has a tendency to jump right to the extreme. It’s never “maybe they’re just not a great employee” and always “THERE’S ABUSE HAPPENING AT HOME AND THAT’S WHY THEY ACT LIKE THIS!!!!”

          It’s pretty exhausting to rule out common work scenarios and jump right to the worst case scenario to justify bad behavior.

          1. pentamom*

            Well, that’s true, but allowing for a possibility that should be ruled out isn’t “jumping” to that, nor is it ruling out other causes. At least, I wasn’t jumping to it or assuming it. I just think it’s something to be considered. If you’re going to solve a problem, it’s best not to rule out possibilities just to avoid feeling like even considering the possibility is over-dramatic.

            1. Tinuviel*

              What does “allowing for a possibility” look like? Should we speculate on all kinds of reasons and come up with ways OP can tackle each of them, slowly moving further and further from what’s likely or in the letter? Or should we stick with common/likely scenarios that are more helpful to OP?

          2. Wendy Darling*

            I mean, I stayed late at work every night for weeks because my in-laws were staying with my partner and I in a 2-bedroom apartment and at my desk at work after everyone else left was legitimately the only alone time I got outside of a bathroom. My in-laws are nice but can be tiring and I am an introvert.

            That’s what I think of when someone is suggesting something going on at home. In my case I didn’t work, or even say I was working, all that time — I had a great relationship with my manager so I straight out told her I was just watching some netflix before I went home because my house was currently a total zoo. But I’ve definitely had some managers who I’d be like “Oh I just have all this work to do ha ha yeah it’s no problem I am totally good being here literally forever!”

        2. Ask a Manager* Post author

          The rule from the commenting rules is:

          Limit speculation on facts not presented by letter-writers to reasonable assumptions based on the information provided. If you’re speculating on facts or context not in the letter, explain how it’s actionable for the letter-writer. “She might be stealing your lunch because she can’t afford her own” is not actionable (and quickly becomes derailing). “She might be stealing your lunch because she can’t afford her own, and so you could try XYZ” is actionable.

      1. Kathlynn (Canada)*

        And how do you stop someone from yelling at you, to try and provoke you? Whether or not you have a violent history? You remove yourself from the situation. Could he have removed himself in a different manner, yes. But they way he did so isn’t wrong, nor does it say/prove that he has a history of violence.

      1. MCMonkeyBean*

        Yeah, most people don’t have to actively avoid their spouses in order to not hit them…

        1. Melon Soda*

          Not to push this tangent too far, but c’mon guys, you wouldn’t want to avoid a home where someone was always trying to pick a fight? You’d just go “well as long as I practice my wonderful self control and don’t hit anyone, this is otherwise a lovely home environment to be in”? No one says he avoided home as the one way to avoid jail.

        2. I Wrote This in the Bathroom*

          To be fair, most people’s spouses don’t show up at their work and then behave in such an aggressive manner towards their spouse in public that the bystanders have to call the cops.

      2. Lissa*

        It doesn’t sound like he did hit her though, and sounds like she was the one who got arrested? Not to say people are always truthful but the way it’s framed I didn’t get the sense from this story he was the one in trouble.

        1. WorkMore-AvoidJail*

          This is correct – he had a record from his early 20’s getting into bar fights (with other men – our understanding was he never hit a woman) and still had some anger managements issues he was in treatment for. She was actively trying to push his buttons so he followed his lawyer & therapists advice to stay away and not put himself in a situation where things could go sideways. Her mother was the one who warned him what her daughter was planning and ended up providing proof during the divorce proceedings.
          Yes – he did press charges against her and my husband’s company pressed charges for trespassing on private property and possibly destruction of property (can’t remember exactly what).

      3. EPLawyer*

        Actually, in my experience the abuser tries to goad the victim so they can point fingers and say “see what I have to put up with?” So they can be the victim. It’s about control. They control the situation to make the victim look bad. So perfectly plausible to me.

        1. OhNo*

          That’s my thought, too. Not to get too far off on a tangent, but it sounds like the wife in this case was emotionally abusive, and the husband was trying to avoid that. All perfectly reasonable.

          Let’s hope the OP’s employee isn’t in a similar situation, because I don’t think there’s a good way for a boss to say, “You don’t have to go home, but you can’t stay here”.

      4. sunny-dee*

        Not necessarily. Women are actually much more likely to initiate domestic violence than men (although they’re also more likely to be injured — because they’re smaller and weaker than men). It is entirely reasonable to be concerned that a woman may initiate abuse in the hope of getting him to hit back, and then blaming it on him to the cops.

        1. Business Librarian*

          Not what I’ve read. Here’s the abstract of a review of data and studies specifically addressing women’s use of violence:
          The major points of this review are as follows: (a) women’s violence usually occurs in the context of violence against them by their male partners; (b) in general, women and men perpetrate equivalent levels of physical and psychological aggression, but evidence suggests that men perpetrate sexual abuse, coercive control, and stalking more frequently than women and that women also are much more frequently injured during domestic violence incidents; (c) women and men are equally likely to initiate physical violence in relationships involving less serious “situational couple violence,” and in relationships in which serious and very violent “intimate terrorism” occurs, men are much more likely to be perpetrators and women victims; (d) women’s physical violence is more likely than men’s violence to be motivated by self-defense and fear, whereas men’s physical violence is more likely than women’s to be driven by control motives; (e) studies of couples in mutually violent relationships find more negative effects for women than for men; and (f ) because of the many differences in behaviors and motivations between women’s and men’s violence, interventions based on male models of partner violence are likely not effective for many women.

          Link to the article in a reply.

          1. RUKiddingMe*

            Did you get that from my dissertation?

            LOL I know you didn’t but this is exactly my research and you are completely correct.

      5. pentamom*

        It also sounds like the way someone would frame it if their emotionally abusive spouse were attempting to goad them into violence.

    4. What's with Today, today?*

      We had an employee like that – well, I’m Vice Chair of a board for a non-profit, and the former Exec Director did that. We put numerous plans in place (and tried to hire another employee to help, which she declined) and then would still get emails flaunting the time stamp (I could have written that part of the email). She eventually left claiming work/life balance. But we all knew it’s really just her. Our new Exec Director has no problems with work/life balance, and former Exec Director is (surprise) having the same work/life balance issues at her new gig.

      1. What’s with Today, today?*

        For clarification, she’s a martyr, but her martyr syndrome is intensified by issues at home (which she talked about loudly).

    5. Lissa*

      I feel like the fact that he keeps pointing out how long he stays would indicate away from that, but maybe. Like, to me if he was say, avoiding a bad situation at home or something he wouldn’t say things like “look at this email receipt” and keep going on about how long he stays.

    6. Artemesia*

      This is IMHO the most common reason people diddle around doing nothing much all day and then stay late and come in on weekends. Lots of people don’t want to go home — they don’t want to have to deal with their kids – their wife can do it — they don’t have a good marriage or aren’t willing to pull their oar and so avoid the household. The boss can’t really intrude on this, but if time is being wasted during the day and then hours stretched, being firm about not staying late but being productive during the day is appropriate.

      1. Anon for this*

        For years, my dad used to find excuses to go in to work every damned day, like 6 or even 7 days a week, and it was definitely all about avoiding being home! And my mother was too dense to figure out that he was avoiding HER. *sigh,* They had a lot of issues, and neither of them had any idea how to actually work them out. So my dad hid out at work, and she constantly griped about him to me. It was l8ads of fun … NOT.

        Dr. Phil (of whom I am a huge fan) always says you should never involve kids in adult matters or in things over which they have no control. Sometimes I almost wish my mom was still alive, so I could throw that in her face. (Not really; I mean I’d never do that. But she’d legit deserve it,)

    7. Quickbeam*

      I worked with someone once who logged huge long hours into the night. When the manager finally looked at computer use, they found out he was writing a book after the rest of the team left. Is all that after hours work really work related?

      1. Devil Fish*

        “Is all that after hours work really work related?”

        In OP’s case, the work seems to be getting done, so I’m guessing yeah?

        In your case:
        1) Was he salary or hourly?
        2) If he’s salary, who gives a shit if he’s writing a book after hours?
        2a) Qualifier to that question is if he was bragging about the time spent working late rather than just being present and someone noticed; if he was pretending to work when he really wasn’t, that was stupid and wrong.

    1. Triumphant Fox*

      Is this necessary? There’s no indication the employee is in the military and this generalization isn’t really helpful or thoughtful.

      1. London Calling*

        I don’t see any harm in pointing that out and problems at home might be the case here as well. Checkert was generalising from experience, which in the absence of concrete information is what we’re all doing.

        1. Triumphant Fox*

          Sorry, did Checkert comment elsewhere that I’m not seeing that they were in the military and had that experience? I guess this just felt like a pretty broad statement about a whole sector that may doesn’t seem to apply here without much additional commentary to either support it or add any context.

          1. QCI*

            Checkert didn’t claim Braggart was military, the comparison was “military people also do this thing”, which could also be said of any kind of job without set hours.

          2. Checkert*

            For the record, and not that I have to prove anything to you, I WAS in the military and have worked in the federal government since, and the same types of behaviors can be seen in some across both. Feel free to thank me for my service.

        1. Snacksrock*

          My brother in- law works 7 days , 10 plus hours all the time. He has no desire to stay home with his wife. So it is possible that this is the issue with this person. When asked by a co-worker why he doesn’t just stay home with his wife, he just shrugged. They do not need the money. ( we all know that for a fact). He would just rather go to work than stay home

          1. The Man, Becky Lynch*

            Yeah, some people are just workaholics. It’s a real thing. No problems at home. Or perhaps their spouse works opposite shifts so they have no reason to rush home to an empty house either.

      2. Artemesia*

        It isn’t just in the military — this is very common in any workplace — the people who are not more productive than others but spend long hours avoiding going home.

        1. Earthwalker*

          +1. Not that anything in the message indicates that home issues are positively the reason for his overtime, but it’s certainly possible. People do this, and when they do they don’t brag about problems at home but talk up their company loyalty instead. A manager who is trying to solve the problem by focusing solely on whether the problem is workload or time management could be tripped up if the behavior actually had such an unrelated cause.

  3. Pay No Attention To The Man Behind The Curtain*

    “Look at the time receipt on this email — I was here until 10 p.m.” is such an odd thing to say unprompted that his overtime seems to be performative.

    1. CupcakeCounter*

      Agree – its very weird. The only time I sent something like that to a boss was to underline the serious issues in our department and needed him to grow a pair and stand up to the big bosses who kept expecting more and more work from fewer and fewer people but that doesn’t seem the case with Bob and OP.

      1. Sparrow*

        Yes, exactly. The only time I can recall saying something like this was to very clearly signal, “This is not working for me,” and as such was very enthusiastic about finding and implementing a solution when my boss showed the appropriate (concerned) reaction. This just strikes me as odd, unless he thinks OP isn’t serious about continuing to work with him to find a fix – or he’s just finding the solutions really ineffective and doesn’t know how to articulate that.

    2. Witchy Human*

      My brother complimented his kid once for helping another kid pick something up on the playground, and then he went through a phase determined to constantly Help Pick Up All The Things so he could run back to Dad to demand praise for it. It was very annoying.

        1. Jaydee*

          It’s a pretty normal thing for little kids to want to be a helper and to do things they think/know will earn them praise. Our son is praised regularly and told and shown how much he’s loved just for existing. And still he regularly insists on “helping” with things in ways that are not actually helpful because he knows that helping is good and he really values being seen as a helper. He’s almost 9, so we do have the talks with him about how to figure out if what you’re doing is *actually* helpful or is just a way you’re trying to get attention and be seen as helping.

          1. Niktike*

            My toddler is constantly trying to “help” by closing the fridge door while we’re in it, intentionally spilling things on the floor and then pointedly wiping them up, taking his toys out just to put them back, throwing away stuff we want to keep, etc. Unfortunately, he’s not old enough to distinguish when his help is not helpful.

            1. Rebecca*

              Yeah. My five year old helps cook by eating everything he’s helping to prepare. ;)

              But the actually helpful vs performative for praise thing is super normal. My students fight over who gets to help me carry my bag or books or whatever, and really get off on the status being the helper gets them. It’s a process.

      1. hbc*

        We spent a good three months regularly waiting outside busy places for my son to stop holding the door. He called it his job, and he was happy to do it for 15+ minutes. Of course, he’s six and didn’t whine about how long he did it, so he’s got two things over the OP’s report.

    3. Just Elle*

      I think the key is going to be to dig into WHY he did that. Is it because he’s feeling incredibly overburdened and genuinely asking for help addressing a systemic issue (not just taking one thing off his plate)? Is he wanting praise or a raise? Is he covering up for his poor time management?

      At my last job everyone valued time-at-work over actual productivity. It was super aggravating when I put my head down and worked for 9 grueling hours and left, only to get noses turned up at me… while the people who constantly bragged about working >12 hour days took half an hour every morning standing around sipping coffee, took 2 hour lunches, and horsed around for the greater part of the afternoon before ordering in takeout to eat while they played on their phones for an hour as ‘dinner’. Actual productivity time was probably more like 6 hours, but the bosses were constantly praising them for it.

    4. Pay No Attention To The Man Behind The Curtain*

      Is the OP sure that he’s actually staying/working late, or are they just relying on Bob’s self report? Because, what if he isn’t staying/working late, but is creating a paper trail (email trail) that says he is. He might be building a cover for personal problems like having an affair; or he could be working a side job using the resources of his full-time job.

      1. AndersonDarling*

        I’ve seen people use the auto-send feature on Outlook to distribute emails at late hours to make it appear they were working late.

    5. That Girl from Quinn's House*

      I worked with someone who LOVED to tell you what long hours he worked.

      He was wildly fudging his hours. He’d get in at 10:15 but claim he’d been working since 8:45 (when he pulled out of his driveway and then stopped for breakfast). He’d take a 30 minute morning break, a 30 minute afternoon break, and an hour or more for lunch. Then he’d tell everyone he was staying until 6 but sneak out at 5.

      The building was spread out and he was salaried, so this went unnoticed by his bosses until his staff realized they weren’t getting their mandated meal breaks because he wasn’t around to provide them, and they started ratting him out to his boss instead of covering for him. He was, of course, fired.

      1. Anon for this*

        I worked with someone who stayed at work till all hours at night *and received awards for it*. This person’s manager would call their name for another award and say something like “They work crazy hours”. A few helpful tricks this person had up their sleeve to accomplish this:

        1) They were very social, and would chat with their team all day so that no one was able to get any work done. Then at 5, they would be “oh no, we are behind schedule, everyone stay late tonight, I’ll order takeout for the team” (and expense it of course). Then the team would finally go home and this person would stay for a couple more hours and finally leave late at night.
        2) They had a side gig, which,as I’ve heard through the grapevine, they sometimes worked on, using the company’s equipment, after everyone was gone.
        3) My favorite story was from a coworker who ONCE had to stay late to meet a deadline. He told us that, by 9 pm, it was just him and Long-Hours Alex in the office. Long-Hours Alex shut down their computer, packed their things, and was on their way out the door when they spotted my coworker. Alex turned around, went back to their desk, powered the computer back up, and went back to (working?) and was still at it when Coworker finally left for the day.

        This would’ve been funny, if not for the fact that Alex’s bizarre work hours were being praised by the managers and had started setting the work culture in the office. It started getting to the point where it was considered normal to work extra hours, and people who worked 40hr/week were being frowned upon. Don’t know how it all ended, because I left and Alex stayed. Hopefully they aren’t all working 100-hour weeks now.

    6. RabbitRabbit*

      There is someone in another department at my workplace who has no apparent reason to work long/insane/off-hours, and yet has seemingly done so, for years. I was once in a meeting with her, one of her bosses, and some other people about trying to redistribute her workload and she was quite possessive of it. Nothing came of that particular attempt.

      I know she’s also been spoken to about not sending various non-urgent e-mails at odd hours; she tends to cc everyone she can think of, including my manager and his boss, and those people sometimes need to watch for actual emergencies and act on them. She was even told to use Outlook to create those notification e-mails and auto-send them during more usual business hours. Nope.

      Pretty much everyone sees through her behavior at this point and her attempts to get attention/prioritization don’t work.

    7. Sharrbe*

      Ridiculous conspiracy theory time! He’s trying to establish alibis for his secret life as a criminal!

      1. OhNo*

        Maybe he’s casing a bank or jewelry store next to the office. He’s staying late to dig his secret tunnel into the next building!

    8. Laurelma*

      Could be doing some work, at work after hours and doing things he doesn’t want his spouse to know about? Calling a girlfriend, porn, etc. Having an affair with someone that works next door.

      Am wondering if is output matches the hours he works? OP might want to ask IT to check his computer log. He could sit there and be viewing women on a dating site for an hour or so here and there. Or have a chat up and running while working that he doesn’t want seen during the day. He might be stating that he was at work, look at the time stamp because I was doing something else that I didn’t want to admit to???

      OK, I’m going off the deep end here.

    9. Elenna*

      Yeah, my first thought was that he’s procrastinating, working really slowly, or taking lots of breaks and then acting like “Look what a good employee I am, I stay so late!”. Either because he wants to brag, or because he actually thinks people will think better of him if he stays late.

      That’s where it would probably help to take a good look at how much he’s actually doing.

  4. Kater*

    My read is that this guy gets a kind of pleasure out of martyrdom (like the people who brag about how little sleep they got last night.) He seems to be acting under the impression that his long hours are praiseworthy. It’s a pretty common thing in business that long hours are seen as praiseworthy, and in some cases, expected. Why else send an email that has no point other than to humblebrag about how late he’s working? He could think “she says not to work long hours but that’s just the official rules, the unofficial rules are that I’m a good guy.”

    Another possibility is that he has a terrible home life and doesn’t want to go home.
    At a company I worked for once, there was one guy who was always the first to arrive and the last to leave. We later found out that he was embezzling and wanted to make sure he was always there so that no one found out.

    1. ErinFromAccounting*

      Yep, in fraud examination class at school, some of the red flags for embezzlement was long hours, little-to-no vacation days, and an unwillingness to pass off responsibilities to others. When someone has a reputation as a high-performing control freak, managers and colleagues tend to let them do their own thing… perfect opportunity for fraud.

    2. Oh No She Di'int*

      My read is that this guy gets a kind of pleasure out of martyrdom

      I came here to say this. The fact that OP seems to have gone out of their way to limit the workload and therefore the hours, and yet somehow nothing ever “sticks” seems to be a red flag.

      I have one such employee now. No. Matter. What. I try, she simply will not rein in her work hours. There is always something she can be just a little bit more picky about, a draft that could get one more proofreading. I have given it a rest for now. I’ve come to the conclusion that she simply likes working this way. But I have made frequent and robust pronouncements to the staff as a whole that people are not expected to stay after 5 pm. Indeed after about 4:00 people can leave if they’re done for the day–no need to ask permission, and no one is to judge them for it.

    3. Batgirl*

      I’ve never understood this; it just looks like poor time management. I think the OP should phrase it as such too, after offering help : “The workload and deadlines need to be better managed. Working late every day is chaos”.

  5. Aspiring Chicken Lady*

    I’m wondering if he’s a) playing the victim because he wants attention for his work, b) unable to work well during regular hours and instead is essentially “flexing” his more productive time later … but still putting in hours 9-5, c) completely unable to time manage, d) avoiding being home for some personal reason, or e) some combo of all or some of these.

    I think the answer to the issue lies in understanding what’s going on.

    1. ThisColumnMakesMeGratefulForMyBoss*

      So many possibilities…I’m thinking he works harder instead of smarter. Once OP digs in and figures out the WHY, they need to treat this employee similarly to someone who is under performing. Come up with a plan and if they don’t follow it, keep addressing it until it’s fixed, and discipline as necessary.

  6. Jennifer*

    He’s a martyr. I’m guessing he brags about never taking sick or vacation time. He’s always going to do this unless the boss comes to him and says that she expects him to go home at x time unless he’s working on a special project or something that requires overtime.

    1. Jamie*

      I know the type. I worked with someone who came back to work the day after their spouse had a limb amputated and was praised by tptb to the heavens for his dedication…even when they recounted how their spouse wished they could take a few days which they had on the books and absolutely could have.

      Soulless company loyalty above all else is rewarded in some toxic workplaces.

      1. Jennifer*

        That is so sad. I want to work for a company that would strongly advise me to go be with my spouse in the hospital. If I were his manager, I’d worry that employees felt that had to come to work no mater what.

  7. BRR*

    Another possibility other than time management or workflow is he’s doing this solely to flaunt it. I’ve worked with people like this and it was all about the show. They used this as a way to show how they were a rockstar employee. To their credit, it worked because of some awful managers who ate this up.

    1. Marie*

      This particular brand of workplace toxicity has driven me even more crazy since I became a parent. Anyone with daycare pickup MUST leave on time — I can never advance in a company where staying til 7pm is expected.

    2. MissDisplaced*

      It does kinda sound like that.
      Especially if you’ve brought it up.

      If it’s not, the work could be coming all in at once. I used to work at an ad agency where we sat around all day, but then got slammed at 3pm ever day which caused us to have to stay until 9 or 10 at night. It really sucked!

  8. AdAgencyChick*

    This is an old letter, so OP is long gone, but assuming it’s a time management issue and the employee seems to like playing the martyr, I’d add the following to Alison’s script:

    “You aren’t increasing your likelihood of advancing at this company by doing this. It’s not an expectation of people in your position to stay here at all hours, and your doing so can create a perception that that IS the expectation. I’m telling you flat out that you will not earn brownie points with me or get promoted because you’re doing this.”

    1. Landry*

      There is nothing wrong with wanting to be a rockstar employee. The mediocre always attack high achievers, whether in school, athletics, hobbies or the workplace.

      1. Environmental Compliance*

        There’s a pretty big difference between being a rockstar employee and simply staying late. Those are not mutually required.

        (It’s unclear to me if this is what you mean with your statement or not.)

      2. Librarian1*

        @Landry. Wow, that’s unnecessary.

        Also being a “rockstar” (whatever the hell that means) employee does not equal working long hours. He could be working long hours because he wastes time during the day or he’s much slower at his job than everybody else is.

        1. voyager1*

          I kind of get where Landry is coming from, AdAgencyChick’s response is pretty blunt (maybe even adversarial) considering we don’t know why then employee is working the hours he is. Everyone in the comments seems to be jumping on the “he is a martyr” bandwagon, but that may or not be the case. AAM really nailed in her response that pinning down why the long hours are occurring is important.

          1. Librarian1*

            I guess I don’t agree with that. I had the same thought that AdAgencyChick had while reading the article. And she didn’t say anything about it not being okay to want to be a successful employee, she’s just pointing out that working long hours is probably not going to get him anywhere at his current employer. And I feel like Landry is conflating being a great employee with working long hours, which is something I hate. One can be a great employee while working normal hours.

          2. Oh No She Di'int*

            I think that AdAgencyChick did say: “Assuming ABC, then say XYZ”. That’s an “if” statement. If ABC is not true, then don’t say XYZ. So it’s a self-regulating system. Indeed, there are many possible reasons why the employee may be behaving in this way. AdAgencyChick has addressed one of them. Other commenters have addressed others.

      3. fhqwhgads*

        The rockstar would get all the stuff done WITHOUT the extra hours. Anyone can be double-productive if they put in double-hours. That’s not high-performing, it’s just math. If his work can’t be done in normal hours he’s either not efficient enough at it or the company has unreasonable expectations, but since the boss has tried to balance this person’s workload I don’t think it’s the company having unreasonable expectations. Either dude is choosing to stay late when he doesn’t need to or dude is too slow to finish on time.

        1. Eleanor Konik*

          This. I work the shortest hours of all the people on my team because I am *efficient* and *plan ahead,* whereas the other people on my team frequently work 13 hour days multiple times per week because they either don’t like going home to their stressful children (stated fact, I am not projecting or assuming) or because they are disorganized and can only plan a day in advance and get overwhelmed with emails, performative overachievement that our bosses neither see nor car about, etc.

          This is a salaried position, no overtime, and they both have the same workload, which is less than mine because I am the team lead and that comes with extra paperwork.

      4. The Man, Becky Lynch*

        It’s not “rockstar” level to just be there all day, every day. You have to be efficient and getting things out ahead of schedule and so forth. This guy seems to be struggling if anything, the only time I’ve had to work late nights was during a seasonal rush or when I was severely overworked and understaffed.

    2. Landry*

      Of course the employee may be earning brownje points with people more senior than OP. I think the employee is gunning for OP’S job.

    3. Close Bracket*

      That’s unnecessarily hostile. We don’t know that he’s playing the martyr. There are any number of motivations for working long hours.

      1. Oh No She Di'int*

        Yes, there are. However, I think that is covered by AdAgencyChick’s caveat: “Assuming X, Y, Z, add this to the script.” In other words, if the conditions are as such, then one can say the following text. If conditions are not that, then don’t say that text. It’s a self-regulating system.

        1. AdAgencyChick*

          Coming in very late to say: Yep, that is exactly why I put the word “assuming” there.

  9. banzo_bean*

    I had a boss that would do this to her team, and it was definitely in part performative. At the time I was in school with night classes so leaving at 5:00pm was a hard deadline for me, but she would often send emails late at night from the office to demonstrate how late she had stayed at work.

    A lot of this was due to over comitting to clients, failure to communicate deadlines with clients, and mostly a failure to effectively manage her own time. She continued to take on pro bono/free work despite pleas for her staff not to, and it made her miserable and very self righetous.

    If I was a client and I asked if something could be done on time, I don’t mean “can this be done by Friday- even if it means your work every night till 10:00pm?” I mean could it resaonably be done by Friday. Communicating with clients about deadlines/workload helps train them into having reasonable expectations of you and helps them properly frame their needs/timelines with you.

  10. JSPA*

    I’d be tempted to deal with it by suggesting he take a day off, weekly. Or setting up a program that logs him out, no override, at 8 PM. Or suggest that his schedule be changed so that he starts at (and can’t start before) 10 AM, if he’s a night-owl, and is using the late hours to “explain” morning ineffectiveness and grogginess. Frankly, he also could be home and be sending the 10 pm emails to look more hard-working than he is.

    1. Jamie*

      I’d be tempted to deal with it by suggesting he take a day off, weekly.

      That would get me to start doing it, and I’m sure others in his office might as well…40 in 4 days is a dream for a lot of people.

  11. Jamie*

    I had a boss once who said there are only three reasons people work excessively long hours indefinitely (as opposed to a finite crunch time): They have a sh*tty manager who can’t manage, they are in over their head, or they are avoiding going home.

    It’s a bit simplistic and sure there are other reasons, but I’d bet the vast majority falls into one of those 3 categories.

    1. Close Bracket*

      Or they love working and being productive? If your manager couldn’t think of that reason, he’s the shitty manager.

      1. Jaydee*

        But are they *really* productive or just enjoying the appearance of productivity? Research has shown that productivity hits a cliff if people work more than 50-55 hours in a week. So I would question whether someone who is regularly working long hour is actually accomplishing more than (or even as much as) they would working 40 hours a week.

  12. Blessed with Flushable Turds*

    I’m someone who needs to flex my hours because of personal/family commitments. I also work a job with incredibly variable workflow under tight immovable deadlines. And I love my job, I do all this by choice, and sometimes I work until 7 or 8 pm, or start at 6 or 7 am to make it all happen. I don’t kill myself to make it happen, and I still largely average 40-ish in the end. It’s just the nature of this job. I don’t necessarily go around flaunting it, but if someone leaving at 5:30 says something like “How much longer are you gonna be here?” or “OMG when did you get here today?” I’m going to answer honestly. I’m going to have emails with timestamps on them that run counter to some people’s expectations. I could be described the same way OP is describing Bob.

    If someone like OP came to me with an effort to “fix” all this, I’d be totally put off. Like Bob, I too am “a very hard worker, reliable, and always gets the job done. He has a great reputation in the company, and everyone goes straight to him for help with projects” … and THIS is what you want to get on me about?

    My point – if your problem is only about Bob’s hours, shut up. If your problem that Bob is complaining about his hours, or that his workload actually *is* too much on a consistent basis, then address THAT, and not that this guy is committed to doing a good job.

    1. Yorick*

      But I assume your manager knows you’re flexing your hours, and hasn’t talked to you about how much overtime you’re working in an effort to get things off your plate. Your situation is not the same as in the letter.

      1. Blessed with Flushable Turds*

        I am Bob, somewhere in the middle of this story, right before
        “As his manager, I felt obligated at the beginning to find out where these tasks were coming from and what I could take off his plate.”
        “I believe the problem is ineffective time and task management.”

        And the fastest way to make me hate my job would be to consistently talk at me about a problem that doesn’t exist instead of helping with any that do.

        1. hbc*

          Your regular late hours can actually be a problem, though, even if you’re happy to keep doing them. At minimum, it’s masking a resource issue, and it’s giving an indication to others that the way to get ahead is to not have a life outside of work.

          And frankly, a lot of the people I know who are workaholics to the extent that the OP is talking about are not getting nearly as much done as they think as well as they can, or using their time wisely.

    2. AvonLady Barksdale*

      Your situation, as Yorick pointed out, is very different from the one in this letter. The workload itself HAS been addressed and no one has asked for flex time. I imagine that you’re not sending messages about the time stamps on your emails with, “Hey, look at how haaaaard I work.” Bob’s hours are a problem not because they’re late but because Bob won’t change anything even though he complains.

      When an employee willingly stays late for personal reasons or just a preference for getting tasks done before heading home for the day, it is a far different scenario than an employee staying late just to complain that he stayed late.

      I know someone who “performs” like this. She has no concept of time management and absolutely no desire to address it, though her superiors have tried. She wants to show everyone how “hard” she works because she stays late, even though there are periods in the day when she is certainly not working. That’s the issue here, not that Bob is in the office past 6pm.

      1. Poor Bob*

        Is he actually complaining? It sounds to me like he’s saying, “see boss, I *do* need to work these hours because project X and Mr Y are needy, so I’m doing my job just fine, quit bugging me about it.”

  13. ArtK*

    You’ve got someone who doesn’t want to say ‘no’, combined with resentment about the load that produces. The former gives you the workload problem, the latter gives you the martyrdom (“flaunting” in the LW’s terminology.)

    Alison’s advice is good, but my suspicion is that the LW is going to have to act as a gatekeeper for new requests. One other thing that I noticed: The problem employee manages a group. I’d look into whether he’s delegating appropriately; fixing that may again require the LW to become a gatekeeper.

    1. Elizabeth West*

      Oh, that’s a really good point. I had a team lead once who was super reluctant to let go of things and consequently she ended up working more hours. She was efficient despite that (and something of a workaholic–like, her idea of heaven was spending six hours working on a giant dashboard spreadsheet), but Bob may not be.

    2. TurquoiseCow*

      Oh, good point about him being a manager. I used to work for someone who constantly complained about how late he worked, but never delegated any of it to those of us beneath him, even though he could easily have given it to me. Whenever he said “oh I was here until x time” or “I got in a XAM and I still have # tasks to do!” I’d speak up and say “oh, I can handle x or y task!” and he’d just be like, “oh, no, it’s fine, I got it.”

      He also had a tendency to jump on everything like “OMG I NEED TO DO THIS NOW” when some of it could have waited a day. And on the rare occasions he would delegate, he’d explain in detail what needed to be done, even though I was more than capable of figuring it out on my own.

      Maybe Bob isn’t delegating, or he’s spending a lot of time micromanaging what his reports are doing, and that’s not allowing him to get his work done.

    3. Close Bracket*

      “Flaunting” is a judgmental term that injects a presumption of Bob’s mental state that LW can’t know.

      1. ACDC*

        How does “flaunting” tie to a mental state? In every context I’ve heard it in, it’s a synonym for boasting or bragging. I don’t think it presumes anything, it’s just someone’s opinion of his tone or reason for saying what he said.

  14. Sunflower*

    My big question here is what kind of authority the employee is given to say no? If the problem is ineffective time management because he feels like he can’t say no, that’s a very different problem then someone who can’t focus or is wasteful of resources. Before reprimanding him, I’d suggest giving more feedback on how he can say no, make sure he feels empowered and address his concerns about saying no.

    I was this employee before in a way- I worked in a support service at a BigLaw firm and my boss gave me the same ‘we can’t say yes to everyone’ but at the end of the day, we kind of had to anyway. Saying no consisted of 1. me telling my boss I was going to say no 2. drafting a long, carefully worded email about why I had to say no and running said email by my boss. 3. Person I emailed emails my boss complaining 4. Boss says deal with it so person emails grand boss 6. 50% of the time, it would lead to a meeting where the person complained that our team didn’t understand the demands and flexibility that comes with working in this type of environment. So you can see why often times, I just said yes. Did I mention those people also had input on our performance reviews?

    I’m also wondering if the employee thinks this is helping his chances of getting promoted- or is he worried about his job being eliminated? The way my performance evals were set up, people I supported gave feedback so if I said no to someone enough, I was given bad feedback which impacted if I was promoted/given a raise.

    It’s also possible he’s just trying to be a martyr but I’d look at some other things before yanking his freedom to manage his own tasks.

    1. Fikly*

      Given that his manager actively has expressed how much he wants the workload to decrease, his authority is going to his manager and saying they are asking me to do x, and it will require y amount of time.

    2. WS*

      Yes, my brother also worked for Big Law and had a similar experience – on the surface everyone is supportive of work/life balance, but in reality it’s 100% work. He also had two kids which meant that this would only work if someone else (i.e. his wife or parents) stopped working in order to cover his wildly unpredictable hours. So he left.

    3. Queen of the File*

      Working in a design-related field this was my feeling too. In fact, this part:

      > the person complained that our team didn’t understand the demands and flexibility that comes with working in this type of environment.

      Is exactly what we hear when we push back on “urgent” requests.

      On one hand management wants us to keep normal work hours, but underneath that when we say ‘no’ to things that really don’t need to be done same-day the clients will escalate the problem and we often end up having to do the work anyway (with even less time). The problems in this case are that on a larger scale we don’t handle client expectations effectively, and design staff don’t have the authority to say a ‘no’ that resonates.

  15. Middle-est of Middle Managers*

    I had a very similar employee- never wanted to say no to anyone even when I repeatedly told him to stop working on projects that were of low value/not needed anymore. He’d work and work and work and a good 30% of his time was spent on things he was told to stop doing. He started hiding what he was doing from me but still wanted to get praise for working long hours. He moved on to another team and I still regularly get emails asking me to update some file/project he was secretly working on.

    My first boss sat me down when she thought I was working too much and said, “We generally pay you to work 40 hours. Sometime it will be more, sometimes less, but if you’re consistently doing it, either you don’t know what you’re doing, or I don’t know what you’re doing and both of those are a problem.” I’ve kept that advice close at hand when managing people.

    1. Filosofickle*

      I love what your boss told you, that’s helpful framing.

      In an early job I was non-exempt with no overtime, but I often wanted to work a little longer to improve my work. I was often tempted to do it anyway, unpaid and hidden. Tho we’re talking about an hour here and there, nothing major. I would have listened to this reason and respected it.

      (In case anyone is wondering why in the world I’d work unpaid OT: I was a young designer. The quality of one’s portfolio is critical, and I wasn’t always given enough time for the creative exploration that would lead to the great samples that would get me a better job. This is before we had software/hardware at home, so what I created on the clock was all I had.)

    2. NW Mossy*

      I have a colleague who’s very much the same – Fergus definitely fills his long hours, but with the sort of deep-in-the-weeds analysis that no one wants or needs. I’ve talked with his boss about this many times (it impacts my directs’ workflow negatively), and I don’t envy the task he has in trying to get Fergus to knock it off because Fergus will straight-up ignore direct instruction to stop doing it.

      I don’t know if the same is true in the OP’s case, but with Fergus, it seems tied to his need to be perceived as The Industry Expert Who Knows Everything. He’s the only person I’ve ever met who has said “there’s nothing I don’t know” with complete sincerity, and genuinely believes that if he doesn’t examine every item that crosses his desk in exhaustive detail, he’s failed.

      This type can be madly frustrating to manage, because they’re so deeply convinced that Vanilla Ice had it right with his lyric “anything less than the best is a felony.”

  16. AndersonDarling*

    Is the employee productive later in the day? I had a colleague that would come in later and then chat with co-workers until lunch time. He didn’t really get his work flow going until the afternoon and then he was the most productive after hours when he was in the office alone.
    Some people aren’t ready to get the big work done till later in the day.

    1. juliebulie*

      I am the same way (sort of) and also have trouble with task-switching. So, I work late. But I don’t make a point of sending my boss late-evening emails for the sole purposes of telling him that I’m sending a late-evening email. That’s what strikes me as really odd about this letter.

  17. Non-profiteer*

    Another possibility: is this his extremely misguided way of making a case for a promotion or a raise?

    1. 1234*

      I was thinking this too. Especially if he came from a previous company where people were “rewarded” for working the longest/sending out emails at 10PM just to say they were “working.”

    2. Cranky Neighbot*

      I’m wondering if he’s making a point about his job responsibilities or overtime ineligibility.

      I once had a job where I had to work after-hours regularly, but I was very much Not Supposed to Do That contractually and legally. However, I also couldn’t drop the ball on the work that I was doing. I could only alert my manager to the issue. (I should have gone over her head, but I was like 21 and afraid of being an entitled millennial at the time. I thought the job would get better if I worked harder.)

  18. Acornia*

    If he manages a team of designers, I might consider talking to his team to see if he’s delegating and trusting them to do their work, or if he’s trying to do it all himself and/or micromanage.

  19. Buttons*

    “Look at the time receipt on this email — I was here until 10 p.m.”
    My first thought is to find out what his goal is for sending that to his manager. Is he wanting some sort of recognition, is he gearing up to ask for a raise, is he upset about something, does he feel like other people aren’t pulling their weight? It is just such an odd thing to do.
    If it really isn’t a workload issue, what is it? Does he feel like he can’t trust other people? Does he not have enough ownership and autonomy to push back or decline requests?
    I hope you will update us!
    PS I am working on a tight deadline and I started my workday at 4:30 AM. Do I get martyr points? ;)

    1. Poor Bob*

      It reads to me like he’s justifying why he needs to work late, since OP has been consistently on his case about it.

      I don’t think there will be an update, this is an old letter so might as well be hypothetical.

    2. Arts Akimbo*

      It reminds me of an episode of Columbo. When the murderer wanted to establish an alibi to show he was definitely not at the scene of the crime at the time the medical examiner and the victim’s broken watch would say the murder was committed, he made a point to ask someone the time. That way, when the police questioned everybody at the art gallery opening, that guy would say something like, “Oh yeah, he was definitely here at 1o pm!” “You’re sure?” “Oh yeah, I looked at my watch and that’s what time it was.” “You just happened to look at your watch when he came in?” “No, he asked me what time it was because his watch was running slow. Funny thing, an expensive watch like that running slow.”

      I guess watch out for any of Bob’s rich relatives with large art collections getting shot while playing the piano at 10 pm?

  20. MD*

    As a medical resident, this happens all the time with us because we legitimately have that much work, but if we accurately log our hours, it’s framed as an efficiency or time management issue. The reality is that administrators want us to lie when reporting our hours if necessary in order to seem like they are within ACGME guidelines (no more than 80h/wk average over 4 weeks), and they threaten our individual careers if anyone doesn’t fall in line.

    1. ArtK*

      Medical residency is its own horrible monster. Although I’m on the outside, a lot of the feeling I get is that it’s a for of hazing. “We had to do this, so now it’s your turn!” The fact that it puts patients at risk is a *very* good reason for it to stop.

      1. Lily in NYC*

        I’ve always thought the same thing! I remember a resident at Johns Hopkins died a few years ago because she fell asleep driving home after working an insanely long shift. I think JH changed their rules about resident hours after that but I doubt it stuck. It’s probably just as bad as it always was.

      2. MD*

        It’s not really hazing though. Hazing is when your own colleagues in the same industry heap shit on you. A lot of it is that hospital administrators and executives know that it’s cheaper to make underpaid residents work insane hours than to hire more staff, including higher-paid midlevels, because we can’t freely leave and transfer residencies. Residency is similar to indentured servitude.

  21. Cyrus*

    Bob sounds really weird. Other people are already speculating about personal problems, which isn’t productive and may or may not be any of the OP’s business depending on details. I’ve actually read that working pointlessly long hours is a warning sign for fraud; it both makes them look like exemplary employees and gives them the chance to do something undetected. Speculating about that is also not productive, I realize, it’s just the first thing that came to mind. Bob COULD just want to please everyone, which the OP considered, but I can’t imagine handling it like he is.

    But anyways, Bob is working long hours even though he doesn’t have to and is pointing it out to his manager even when he knows his manager is trying to prevent it. It’s baffling. Either he’s overworked and the OP won’t admit it, or he’s hiding something, or he’s avoiding something, or he’s just cuckoo.

  22. hbc*

    I think the key thing Alison points out is staying on top of it. As in, weekly meetings to discuss workload–what’s gone out since last week, what’s come in, what took longer than expected. Then OP can catch what the exact issue is, be it over-promising, underestimating completion times, thinking 90% of requests are emergencies when only 5% justify late hours, whatever.

    I’m sure Bob will hate it, but that’s where I would say something like, “Look, we don’t have to do this forever, but I haven’t been able to help you get to regular hours yet. So unless you have another suggestion, I’m going to have to get closer to the process. I can either do the scheduling for you or you can keep me in the loop on how you build your schedule.”

  23. Lily in NYC*

    Many moons ago, I had a coworker who would set his email to send delayed messages (meaning, he’d write it at 3pm and set it to be sent at 9pm). He would then act all smug about how late he worked and implied we were all slackers. He was our lowest performer and my boss was sick of him. She called him out in front of everyone when he made one of his comments and told him “Wow, that is not something to be proud of considering you are behind on every single single one of your projects”. He got fired a few months later.

    1. Beatrice*

      Ha! I do the opposite – if I am sending emails at 9 pm because I’m trying to catch up from home, I try to send my direct reports delayed messages to deliver in the morning so they don’t get the idea that working those kinds of hours is my expectation for them (it definitely isn’t!)

  24. Still Here*

    I did a quick scan, but didn’t see this addressed: Is the employee exempt or non-exempt?

    If not exempt you are require to pay for all hours worked….

  25. Anon here*

    About 10 years ago I was ‘this guy’ as a team leader of a small group and reporting to a more senior manager. In my case it was a combination of two things: increasingly feeling the push and being unable to say no to the people requesting the things, because of hard deadlines (that would lose the company money if we didn’t meet them), politics between senior-level people etc. I felt like I had to pick up all this stuff because I couldn’t trust either my team, or my manager. (And I was proved right on several occasions as when they did have to pick up things, they invariably screwed them up!)

    The second reason was then feeling resentful towards my reports and manager — why should they get an easy life with their job done for them while I get shafted with all this? — so wanted to make them feel guilty or unsure of their own position. Why (in my mind at the time) were they feeling able to have so much certainty, so little to worry about?

    It took me quite a few years since being out of that environment to be able to recognise and articulate those motivations.

    I’m not saying this applies to this guy or ‘diagnosing’ anything, just suggesting some possibilities to think about from my own experience. It may be (I hope) that they are not relevant here!

    1. Anon here*

      Oh and I meant to add but got distracted and hit send too early — I used to do the same thing with my own manager, where we would go through the list of current and upcoming requests, how can the burden be eased, please don’t work that late, I’ll (i.e. my manager) push back on the people and tell them No, etc. I ended up agreeing in the moment but felt that I knew better than he (manager) did about what were the real priorities, how urgent things were, etc.

      (One day we got into a bit of a conflict over this, as I was insistent that something was more urgent/important and had to be done even though he had said to leave it (so I broke ranks and did it anyway, as I knew best!) The argument was “Are you really saying that you think you know better than I do as the manager, what are our priorities and how things should be managed?” I agreed that yes I really was saying that. There wasn’t much he could say, as on some level it was true.)

  26. Close Bracket*

    It’s frustrating when he flaunts his overtime because he’s not helping me do anything about it.

    Does he *want* you to do something about it? Some people thrive on long hours. I work my 40 and go home, but many of the people I work with love working 10 hr days and 6 day weeks.

    Before you bring up burn out, that is not an objective thing where every person who works more than 40 hrs/week is automatically going to burn out. Some people get demoralized when they are prevented from working, and that’s just as important to prevent.

  27. Bob*

    There is another possible explanation for this: has the employee got something going on at home and that’s why they don’t want to leave work? This may be a mental health issue, in which case try and open up a conversation and see if they need any support. The showing off about staying late may be a cry for help.

  28. Perpal*

    I always wonder if there were any updates on these old letters? Sometimes it seems to come out in the comments. Did things ever get better? Agree some people might be happy working ALL THE TIME but most of the time that’s not great and preferable to stick with normal work hours. Even if he just loves working /that much/, it might make an oppressive atmosphere for teammembers, who might think they are also expected to work unreasonable hours.

  29. Decoy44*

    If you’re a hard worker that’s great. But going out of your way to make sure people know whenever you work long hours is obnoxious.

  30. AnonAnon*

    I know this is an old letter but for anyone who has an employee like this, I think it’s worth digging into to find out if it is a workload issue. I have to wonder if him pointing out “I was here til Xpm” is his way of saying “hey, boss, this is a problem, my workload is too high,” and the boss isn’t getting it. I’m guilty of having told my manager “hey, I’m working 12 hour days,” and expecting her to fill in the “and that’s not okay,” but she totally didn’t. In fact, she said “okay.” So I started filling it in for her. “Hey, I’m working 12 hour days, and that’s not sustainable. My workload is becoming a problem” actually got through to her that it was an issue.

    Granted, she hasn’t done anything about it as she promised and keeps giving new projects so now I’m hecka job searching to hopefully find something that won’t kill my mental and physical health so spectacularly, so…

  31. Xavier89*

    Gosh that’s an obnoxious thing to do

    I worked a ton of overtime at my last job but I did my best to downplay it because flaunting it just isn’t a good look.

  32. designbot*

    This was an interesting one for me to read, because I’m a bit like Bob. This isn’t the only option, but I want to explain what’s going on for me in case it’s something others can learn from. When I have one of these sit downs and someone makes me agree to route all requests through my boss, there’s nothing I feel I can say but ‘yes.’ However, in practice it 100% does not work. My boss is often nowhere to be found, and the partners of the company need whatever the thing is done before my boss can be found to discuss it with. OR I say I have too much work and hand it off to my boss… only to have it boomerang back to me a day, a week, two weeks later, but now with even less time to complete the task. So the words are saying “this isn’t how we want you to handle it!” but the actions add up to “this is the only seeming possible way to handle it.”
    So for Bob’s boss and anyone who relates to them, don’t just ask about the beginning of the process (people coming to Bob with work), but ask about how it went. Okay, you handed off X project to Dwight, and what happened then? There’s a fair chance you’ll hear that Dwight had a bunch of questions, or whoever the project came from kept emailing Bob instead of Dwight until Bob eventually just took care of it, or that Dwight couldn’t actually be found in time to meet the deadline.

  33. Essess*

    Personally, every time he ‘bragged’ about being late, I would immediately ask him to explain to me WHY it was necessary to work those extra hours instead of doing it within the normal work day. You could also make it a requirement that if he is going to be working “extra hours” that day, he needs to send you a note at the end of the normal workday letting you know how many hours he plans to work that evening and the justification for needing to work outside of core hours.
    Then you can assess if he’s just slacking off and determine if you need to discuss a performance review about his time management since this does have an impact on other team mates (both morale and workload effect).

  34. Blue Horizon*

    I had this problem early in my career – actually in my first team lead role, where I had one guy that would routinely work until 10pm or so every night and could not be talked out of it.

    Often it’s a symptom of equating success with working harder than everyone else, and using working longer hours as a proxy for that. My mistake was to try and tell him to cut back while acknowledging the effort he was putting in and thanking for it. If you do that then all they hear is “you’re the hardest worker, good job!” and there is not a hope in hell that they will change. To make any progress, you need to reframe it as a negative. “We are committed to a culture of work-life balance here, and it’s important to us that people work normal hours in support of that. By working late even when you don’t need to, you’re undermining that and creating unrealistic expectations for others. It needs to stop.”

    Things to keep in mind: (1) as Alison says, you need to be very, very sure that you aren’t requiring the extra hours either explicitly or implicitly, or else fix that BEFORE having the conversation if you are; (2) you also need to be aware that if this person’s self-image is bound up in working long hours as a proxy for working hard, you could be taking away an emotional crutch when you do this. They may need a little help figuring out what performing well in their role means for them when it’s restricted to 40 hours a week. Think about what you really value about them, and what success looks like in that context, and then reinforce it as much as you can until they are able to see it too.

  35. James*

    What was the culture like where the guy worked previously? This can be a big factor, in a few ways.

    First, he may be coming from a place where long hours are the norm. Some positions in the company I work for, for example, routinely require workers to work 10 hours a day, 6 days a week. I can say from personal experience that going from that to “8 hours and it’s pencils down” (as a coworker put it once) can be very hard, and the longer you’re in a hard-pushing job the harder it is to transition to a typical work week.

    Second, different groups discuss long hours differently. In my company we routinely joke about it, as a means of stress relief–it’s like parents joking about how little sleep they get, not to “humble-brag” but because it’s a way to cope with a situation that’s really hard on a person.

    I would also look at the team as a whole. How do they handle delegating tasks? Not just the employee in question, but the whole team? I’ve been in situations where I was told to delegate tasks, but the folks I was told to delegate to refused to do anything but the easiest/most high-profile tasks, many of which I was not permitted to delegate due to company policy, legal issues, or previous instructions from managers. Cynicism sets in; you soon realize that the team isn’t there to help you, that it’s every person for themselves, and that in this team “delegate” really means “let others take credit for what you do”. And suddenly you find yourself working 16 hours a day. I’m not saying that’s what’s happening. What I’m saying is, it could be–or the employee may think it is. It DOES happen, after all (everyone I know has a horror story about a team like that), and after you’ve been burned a few times you tend to assume it’ll happen again.

  36. Christmas Carol*

    Is there anything wrong with the fact that I’m reading this at work and it’s 5:30, and I hate month end.

  37. nonymous*

    Perhaps this is the detail-oriented part of me, but has OP set up a process for how to handle the excessiveness in the moment? Like if OP and Bob agree that even during crunch time he should not be working past 6P (or 5P or 7P, whatever is reasonable for their org) and when he reaches that point he can sends an email saying “XY&Z still need attention, I estimate there are 4 – 5 hrs of work left” where OP triages those when she comes in first thing in the morning?

    It really doesn’t matter if his estimates are off, because OP will likely call in reinforcements or say that the current state of XY&Z are good enough or some other such rearrangement. This assumes that part of OP’s triage is smoothing any ruffled feathers and resetting expectations. With design work in particular, I’ve found that the end users will sometimes ignore opportunities to give feedback early on (when it is most efficient for the design team to do so) and then want to make a lot of changes at the end. Some of this is about setting expectations with the clients to limit the rework loop. If Bob (or the work culture) has been super-accommodating historically OP might want to start a broader conversation about efficiencies, possibly with some metrics to back her case. But if the issue is that there is a power differential between Bob and the requester, then OP owes it to her subordinate to clarify when he can say no.

  38. pcake*

    I didn’t see any martyrdom in the OP’s letter, so I’m taking a guess that this is what I call Super Hero Syndrome. He’s a super powerful worker who Gets Things Done, and no amount of work or lateness of hour will stop him. He laughs at late hours or long tasks because he is SUPER! And even if you, the OP, don’t recognize his abilities, he feels strong knowing he works harder and achieves more than his coworkers.

  39. K.K.*

    I know someone who ended up like this more or less (with less flaunting). He had so many real or perceived interruptions/distractions during the normal work day, things like talking with clients, project management and coordination, helping new hires, and getting pulled into other conversations in the open office that he could help with as a technical expert. He stopped even trying to get real work product done in the 30 minute breaks between these things and would stay late when he had tough work to get done. In a time sense he had the tune to get the technical work done during his official workday but the combination of his varied responsibilities (assigned and de facto) and his work style meant it didn’t happen. I think it took him a year to realize and name the issue, and a deliberately partly shifted workday was part of the solution.

    I feel like OP should consider this possibility.

  40. anon9*

    Geez, the amount of comments about home life trouble because someone worked late is startling. I often work late because we have flextime and I like to sleep in and make early appointments. Oddly, I’ve also noticed people are only aware of when others leave and not when they arrive. Yikes – oh well!

    Otherwise, LW’s employee is a common workplace creature known as the Underappreciated Butterfly. They will continue to pile on more (usually just time-consuming rather than hard) work (that could easily be split) and refuse to let anyone help so they can complain about how they are so busy and sacrifice so much and no one appreciates all the work they put in, ostensibly in silence. I didn’t read any home-life trouble just based on how much he wants LW to KNOW how long he’s stayed and sacrificed and “is it too much for LW to say thank you once in a while, since I am not asking to be comp’d for this copious and burdensome amount of overtime which I do freely and happily?” I would not be shocked if this employee thought everyone else didn’t work as hard as him. It’s a harsher view but I’ve worked with many of these types – while I do think that he probably doesn’t have much going on personally (I see this as fulfillment seeking behavior in it’s most basic form) – it’s not LW’s job to do anything other than correct the work issues. Stay out of your employee’s personal lives.

  41. CM*

    I totally agree with the advice on this one, but I want to throw something else out there just in case:

    I had a similar situation with a designer I used to manage, and what was actually happening is that he was chronically absent and trying to cover for it by saying he worked really late. “I always have 800 million projects on the go” was a smokescreen for why stuff didn’t get done and “Guys, I was here until 10 PM last night” was a smokescreen for why he wasn’t at his desk during core business hours or why he seemed like he wasn’t engaged/awake/paying attention to stuff. In reality, he was working maybe three hours a day, at all random times. Or, perhaps on the night before something he had procrastinated on was due, he would actually work for a stretch of 12 hours, but it wasn’t a regular thing.

    All that is to say that, I still agree with the advice, but in my situation, it also would have helped if I had tried to get a clearer, more concrete picture of everything this dude was working on and how long it theoretically should take to complete. And I feel like that might be part of what the OP’s getting at by suggesting that the tasks should come through them. Since the person in question is a manager, in this case, it’s not really productive for the OP to take over monitoring all the projects and tasks, but it seems like there’s a problem with how they’re being managed right now, and it might make sense to get super involved for a limited time — just long enough to diagnose what’s going on.

  42. JetlaggedExpat*

    Oh, hey, my mom used to work like this! She’d tell me about what she was doing and I’d explain about (a) time management and (b) workload management and (c) DELEGATION and (d) not letting the perfect be the enemy of the done, but she never heard any of it. It actually did hold her back at work: she became known as a bottleneck because anything that had to route through her got stuck. And it wasn’t that she wasn’t working! She just treated absolutely everything that came across her desk as though it were The Most Important Thing, which meant The Actual Most Important Thing often got buried.

  43. Pink Geek*

    I had a former colleguge who used to struggle with this. They would goof off all day and then stay late to get work done. The problem in their case was constant inturruptions making it very hard to focus on project work.

    They were a manager and trying very hard to be always available but in the end the solution was to put a few hours in the calendar every day to close their door and ignore phone, email, and IMs.

  44. Mama Bear*

    In some industries, working odd or long hours can be reportable to your facility security officer. May not be the case here, but that’s another reason to care about someone’s hours.

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