update: employee is taking all his vacation days at our busiest time of year

Remember the letter-writer whose employee was taking all of his vacation days at their busiest time of the year? Here’s the update.

First, I want to thank the commenters for an active and lively discussion. Certainly many people had an opinion on how I should handle my employee’s future vacation requests. I was a little disappointed that so much of the discussion focused on things that were, and still are, outside of my control: the use-it-or-lose-it vacation policy, that working remotely is not an option for this role, and that taking three weeks of vacation time in a row would be very outside the norm for my company. So, thanks Alison for your active moderation on all posts and focusing commenters on the specific question at hand.

So first, let me explain how our busy season panned out with Bob being gone for a large majority of it. As I expected, December was a complete nightmare for me. I was in the office almost every day at 5:30 am and wouldn’t leave until around 9 pm or after. I came into the office almost every Saturday and Sunday as well. When Bob returned in January, I was so far deep into all the projects that I couldn’t utilize him for almost anything on these key projects other than very small supporting tasks. Instead, I had him focus on all of the “regular” projects that were dropping through the cracks during this busy time. As for me, my insane work schedule continued throughout January, until all deliverables had been completed in early February.

Career-wise, the work on my end paid off. My deliverables were hailed as some of the best the company had ever seen. I received numerous compliments and tons of praise from several EVPs and our CEO (!). At my performance review, I was given a very high rating and received the highest possible raise. I have established myself as one of the best employees, if not the best employee, that holds my role. Personally, though, that crazy work schedule impacted me in some very negative ways. I gained almost 20 pounds due to poor eating, never got enough sleep, and didn’t allow myself any time for any positive outlets for stress (like exercise). It impacted my marriage as well since I very rarely saw my spouse and when I did, I was frazzled. I am not sure how to back out of this for next year….since I showed I could deliver a way-above-expectations deliverable, I feel obligated to deliver the same in the future….except that I don’t really want to work that hard in the future.

That leads me to my team. Bob returned in January and was visibly guilty throughout the month. To be clear, I took the advice of AAM and I said nothing to him before his vacation nor upon his immediate return. I don’t believe I did or said anything to contribute to him feeling bad about taking vacation during that time. I think he could see that the entire department was working so hard and we were all essentially bonding over how miserable we were, and he was left out. Of course, he also was largely left out of any praise or compliment for the deliverables of my team, which was a huge missed opportunity for him to shine.

Bob actually came to me and promised not to take vacation ever again during that time. (Or perhaps, maybe he reads this blog! Who knows.) I let him know I could support him taking time off during our less busy times, even if it is more than week at a time. However, it’s April, and he’s only taken one day of vacation so far. Probably at every other one-on-one I ask him about his vacation plans for the year and encourage him to take some time off, but I still haven’t received any official vacation requests.

I am hopeful that with Bob’s help, this year we can deliver a product that is just as high quality as last year’s deliverables, but without having to make so many personal sacrifices. I have also started keeping personal best-practices documents to supplement documents that my HR team provides. I wish I had thought to ask about used/unused vacation time when I inherited this employee – but that’s now been added to my personal “New Employee Orientation” best practices document.

Thanks again for posting my question, and helping me get feedback on this tricky situation.

Me again. Keep in mind that you don’t want to wait for it to get late in the year, have Bob realize that he hasn’t used his vacation time yet, and then have him decide that he again needs to take it at your busiest time. Say something now — something like, “Can we sit down and figure out when you can schedule some vacation time? Because of how busy I expect December to be, I won’t be able to approve many days off then, and I want to make sure you get a chance to take some time this year.” If he doesn’t want to, then make sure you’re clear with him about the limits of what you’ll be able to approve later (“I want to make sure you know that I’m only going to be able to approve a maximum of X days off in December, even if you have several weeks saved up, so I really urge you to use it before then” or whatever).

You don’t need to find yourself in a situation where last year gets repeated; you can say no to that, and that’s a fair thing to do as long as you’re been really clear with him all along. Just don’t put that conversation off, or you risk misleading him into thinking he could do it again if he wants to.

{ 170 comments… read them below }

  1. Roxanne*

    This: …”wish I had thought to ask about used/unused vacation time when I inherited this employee – but that’s now been added to my personal “New Employee Orientation” best practices document.” This should be part of the plan with employee transfers!

    This happened to a manager I knew when he took on a employee about to be laid off – she had five weeks of vacation accumulated and she had them scheduled before her lay off and took them just after she was adopted by the new team, leaving the new manager happy to get new staff but frustrated that he couldn’t use her for most of the summer.

    1. Kyrielle*

      I just transferred managers (now I’m reporting to the person whose work I have been doing, which is a Good Thing), and one of the first things I did was drop an email to confirm that he was aware of and okay with my scheduled vacation times. (All of which but one day were…at best, hard to move.) He didn’t have my schedule, was glad to get it, and is fine with the times. But I also assume, when getting a new manager, that making sure we’re on the same page with things like that is important for me also!

      1. StudentPilot*

        I’m starting a new job in a week, and when they offered it to me, I gave them my 3-week vacation in August (international travel is involved, and it would be difficult to move.) They were happy to have the heads up, and confirmed it would be no problem. Really, both sides should be involved in the decision.

    2. Cordelia Longfellow*

      One of my colleagues was forced to take three months of leave before he was allowed a transfer/promotion, and that still only brought his leave bank down to an “acceptable” limit of 12 weeks or so. His new unit didn’t want him arriving only to bugger off for six months. (Caveat: this is outside of the US in a field where there’s lots of overtime with the option to take it in leave rather than cash.)

  2. Gene*

    Probably at every other one-on-one I ask him about his vacation plans for the year and encourage him to take some time off, but I still haven’t received any official vacation requests.

    You are hinting. Don’t do that. Say to him straight out, “Bob, if you leave your vacation to the end of the year this year, you will lose it. I will not approve vacation time in our busiest season. I need your vacation plans by our next one-on-one.” Simple and direct.

    1. Nova Terra*

      Yup, this. Even if Bob made his “promise” in good faith (and I’m skeptical enough to think it might have been apologetic guilt talking), things can change, come up, etc.

      Your update said “it’s April”, which means you wrote in this update two weeks ago at minimum. If you haven’t sat down with Bob and laid down your expectations in clear, unambiguous language akin to what Gene suggested, do it ASAP, OP. You don’t want to be in a situation months down the line where Bob complains “but you should’ve warned me!!”

    2. Stranger than fiction*

      Yes. It’s great he came to her, but still needs to get the message loud and clear. He may feel guilty now, then fall comes and his friends and family start talking about hitting the slopes in December (or something) and it lures him into repeating this.

    3. LBK*

      Yep, I agree. Just make it super clear up front that vacation requests for more than X days in a row in December will be denied, and he’ll lose the vacation time (probably not a bad idea to make that well-known to your whole team, especially those who burned the candle at both ends with you last year since that will be a reassuring sign to them that you’re making sure they don’t have to go through that hell again).

    4. Sarah in DC*

      I don’t think its fair to require him to have all of his vacation planned by their next one-on-one. I also work for a use it or lose it company and I haven’t planned all of my time off for the year and I would be pretty frustrated if my boss asked me to commit to which week in October I plan on taking a long weekend or whatever. I do think is reasonable and necessary to communicate to everyone that request for time off longer than X days or with less than X days notice will not be approved for the month of January.

      1. Raine*

        Oh I think it’s fair. The orginal post indicates he took 4 straight weeks off in a row at their busiest time of the year when typically all vacation, travel, and conferences are blacked out.

        1. Koko*

          Right. The problem was when he took his vacation, not that he waited too long to book it. Why does he suddenly need to give 4-5 months notice for a vacation that is not during a black-out time? He just needs to not schedule a vacation during blackout time. If he wants to wait until August to schedule his October vacation, that doesn’t seem from OP’s letter like it would be a problem.

      2. Sciencegirl*

        Many places of employment have employees choose their vacation weeks for the entire year each January or February. This is not unusual.

        1. Koko*

          It may not be unusual, but I don’t think it’s especially common, either. I’ve never worked any place that required me to do that and I’d find it very frustrating if there wasn’t a solid business reason why my holiday vacation dates had to be set 11 months in advance. It would be locking myself into particular dates before I had any idea what my family’s holiday plans were, what flight prices and schedules were going to be, or anything else that might change in my life in the next almost-year. I’ve had family members conceived after January and born by December that changed our family’s plans for the holidays!

          I also like the flexibility of being able to take a few long weekends and maybe one weeklong-trip throughout the year and then decide how much holiday time to take based on how much PTO I have remaining come November. It would suck to block out a bunch of December time in February and then find out in May that an old friend will be in town in July and now I can’t take off time to visit with them because I already committed all my days to being out in December/failed to reserve that July weekend back in February.

          There are just loads of ways where the lack of flexibility would be inconvenient. I wouldn’t want my employer to begrudge me that flexibility just because they would *prefer* to have it all sorted in advance but there’s no reason they *need* to have it in advance.

          1. De Minimis*

            I’ve worked at a place that does that, and it was miserable, and yep, there was rampant sick leave abuse/absenteeism due to the lack of flexibility.

          2. OlympiasEpiriot*

            In my company, the long weekends don’t generally require the months of lead time, but BIG chunks, like a week or more, benefit from the scheduler knowing well in advance. I think there could be a mix of the two, if everyone was responsible about it.

          3. Lady Bug*

            Figuring out all your vacation in January is too far in the other direction. All of my vacation this year (and last year) is based on out if state music festivals or concetts. It’s not like zi can call up the organizers and tell them they need to have the dates and line ups set by January 1st.

          4. Julie*

            This is not all-or-nothing. Bob should plan the bulk of his vacation. He can leave himself a few days unscheduled for long weekends, etc. Or have him “pencil in” a few days and let him know these are flexible and can be changed closer to the date.
            I worked in (and sometimes was acting manager for) a union environment where we had to book our vacation upfront for the year and there were certain restrictions during busy periods (only 20% of staff could be off at the same time during the summer months). These rules were in our contract. There were also many first generation Canadians who wanted long vacations for trips home – when you’re talking 10k in flights for your family, it only makes sense. We managed to make it all work and have some flexibility and understanding for people’s situations.

        2. Green*

          That would be unusually rigid for many professionals. I don’t even ask for vacation days. I just plan my own vacations and keep my manager in the loop.

          1. 2 Cents*

            Me too. If it’s a week or longer request, then I give at least two months’ notice (if not more). A long weekend / part week scenario? Maybe two weeks. (Of course, YMMV at your company.)

        3. AVB*

          It might not be unusual, but it is quite unfair if Bob is the only employee required to book all of his vacation 4-5 months in advance because of one occasion. Also, only giving him 1-2 weeks of notice to decide on his vacation for the year seems like a bad idea to me.

          1. Chocolate lover*

            Doesn’t seem particularly unfair to me if he’s the only one exhibiting the problematic behavior. Just like one person coming in late all the time and everyone getting scolded for it, I don’t think everyone should be punished for Bob’s sake

            1. AVB*

              But it doesn’t sound like the OP has made clear to Bob that it’s problematic. His previous vacation was approved, and the manager is ‘asking’ and ‘encouraging’ about vacation time but it doesn’t sound like he’s sat down and clearly outlined that vacation time in December is impossible. That clear conversation, then giving Bob some time to plan, would be the first step to me – rather than arbitrarily mandating that he decide his vacation for the whole year on two weeks notice, which is what was suggested above.

          2. annonymouse*

            It’s because of a few things:
            Use it or lose it policy (which sucks)
            The fact Bob has to take it in blocks of two weeks or more (visiting overseas family)
            The fact more than one week off at a time is frowned upon at this work place (which, again, sucks)
            Also that Bob showed last year he isn’t great at managing his holiday needs – he didn’t think about it or take it until last minute.

            OP has every right to try and make sure this doesn’t happen again.

            Tell Bob – I need your holiday request/plans (because you take them all at once) by July/August. Any later than that for 2 weeks or more and I can’t approve it.

            These are the plans deadlines – not the actual holidays. Bob can tell OP “I want November off” as long as he tells OP by July/August deadline.

      3. Gene*

        To me, vacation plans don’t need to be detailed, just something like, I’ll be taking a week in late July and a week in early September.

        But he needs to show that he’s put some thought into it.

        1. Green*

          I don’t think he needs to show he put thought into it or plan vacations by their next one-on-one. He just needs to be made aware of the business requirement (he can’t take more than X days in December) and the consequences of delaying (his vacation request will be denied, and he will lose it) and then he can make his own life decisions on the basis of information currently known only to his manager (that she will deny December vacation requests).

        2. Roscoe*

          I don’t think he does though. If you are clear that in December, you can’t take more than 1 week off, why does he need anything besides that. Does he have to tell her “Yes boss, I’m in active discussions for October”? If she is clear when he cant do it, he doesn’t need to tell when he is going to

          1. annonymouse*

            Because in the original post it was stated that Bob travels overseas to see his family so needs to take off larger blocks of time than just one week (also something frowned upon at this company – which I think is ridiculous)

            Because Bob hadn’t kept a good eye on his holidays he had to use it up in one go at the busiest time. Something OP is actively trying to avoid this year

      4. Rusty Shackelford*

        I don’t think he needs to know when he’s taking his next vacation. I think he only needs to know when he’s NOT taking it.

      5. Joseph*

        I don’t think you need to require him to plan it out. You just need to make sure it’s clear to everyone (especially Bob) that “No employee can take more than 5 days of vacation during the busy season between November 25th and January 5th” (or whatever). Make sure this is both (a) crystal clear and (b) documented somehow – this will prevent him from coming back on November 17th and acting shocked that he can’t use all his remaining PTO due to the policy.

      6. annonymouse*

        But that’s the problem.
        Bob didn’t use it until the busy period (December AND January) and took all of it in one go which caused major problems for his team.

        Based on what OP is telling us it looks like that pattern is about to repeat itself.

        I think it’s fair for OP to sit down with Bob and be direct:
        “Bob, I know when you take your holidays you take them in large chunks because you visit your family overseas.
        For you to do this we need to start planning it now so that we can have adequate coverage and make sure it’s not at a busy period.
        What month(s) are you thinking of taking?”

        So Bob is aware that he has to use those holidays. Bob can reasonably say “I haven’t thought that far ahead etc”
        OP can respond “I need to know your holiday plans by July/August to make sure you take the time off you need and to make sure the business/team is ok during your holiday”

    5. BRR*

      Yeah it sounds like it needs to be more explicit to prevent bob requesting vacation time anyways and being pissed if it’s denied.

      We have a use it or lose it policy as my boss had her three direct reports give approximate vacation times. We didn’t have to keep them but it got us thinking how we should use our days.

      1. BeenThere*

        This, approximate vacation times! I never usually know exact dates until the month before the vacation so I usually go to my manager and say “Hey, I’m planning on taking two weeks in the middle of October I don’t have exact dates and they may shifts according to whatever flight is cheaper. Is this ok?”. It’s never been an issue. In the case where the HR system doesn’t let you update days off we simply don’t put the request in until flights are booked.

        1. TootsNYC*

          The last vacation one of my direct reports took, I must have erased twice before I got out the pen. He’d ask, I’d say, “should I write it in ink,” and he’d say, “wait, I need to look into flights.” then he’d change it–his vacation partner couldn’t go then, or flights were too expensive, whatever.

          I’m happy to be flexible–if I want him to accommodate me in his planning by checking the timing BEFORE he buys tickets, I’d better be willing to wait for the ink until AFTER he buys tickets.

          We’re in this together.

    6. TootsNYC*

      yeah, don’t hint. Drag this out into the open–there’s no need at all to pussyfoot around it, and it’s actually pretty unfair NOT to be direct.

    7. Artemesia*

      THIS. It is time to have a very straight talk. ‘Last year when you took off most of December you left us in the lurch and it was very stressful to have our highest workload without one of our key team members. I cannot authorize vacation during that time this year as we will be slammed again. You need to identify some times you will take vacation and get that scheduled or you will risk losing it if you still have unused vacation days in December. We will not have a repeat of last year.’

      You can soften the ‘last year disaster’ talk if you feel you should, b ut the conversation needs to be this direct. It is May — He needs to focus on this and KNOW that last minute use will not be an option this year. The rest of the team actually needs to know this too, so you probably ought to be planning vacation times with everyone. Perhaps announce this in a team meeting, then meet one on one with each person before this month is out to coordinate times and assure that no unleft days will be available in December (or at most one or two per person during that month)

      1. Koko*

        This is really minor but I wouldn’t use, “We will not have a repeat…” language as a way of telling an employee what you expect of them. It sounds too much like a mom or school principal telling you off. Especially since it’s not like the employee intentionally tried to cause hardship last year, he was just thoughtless about his impact.

        I’d stick with language like, “The department won’t be able to cover your absence in December again this year,” “I can’t have you out in December again this year,” or “You can’t take your vacation during our busiest time again this year.”

        But “we will” when what you really mean is “you will” comes off infantilizing.

          1. Petronella*

            I like the “We will not have a repeat” language very much and don’t see why Bob shouldn’t hear it. He put his coworkers through hell last year through his own thoughtlessness, with no consequences to himself, and as others have noted, his “guilt” will likely evaporate by the time December rolls around.

            1. Green*

              Because OP is not a mother scolding a kid but a manager who approved the vacation. “I won’t be able to approve time off in December” conveys the necessary information in a more productive manner.

            2. Mallory Janis Ian*

              I like the “We will not have a repeat” language, but I can see starting off with softer (but still direct) language and holding it in reserve for if he seems like he isn’t getting it.

              The “we will” in this is the OP and the rest of the team, as in “we [the rest of your team] will not have a repeat”of being left shorthanded during the busy time.

                1. TootsNYC*

                  I agree, it’s a drama-inducing.
                  It defines the “we” as “not including Bob.” This “we” cannot include Bob.

                  However, “we can’t have a repeat” is different. In this one, “we” could include Bob.”

              1. Green*

                I still don’t understand how this is somehow preferable to: “We tried it last year, but it was very difficult for everyone else on the team during your vacation, so this year we won’t be approving vacation days during this time period.” No real need to wordsmith this much beyond tonally treating Bob like an adult who can handle factual information and is a part of the team. The prior fail here is on management (OP or predecessor), not on Bob for asking for and receiving vacation.

                1. Kit*

                  People are hearing the “we” as in the condescending “well, what did we learn?” or “We won’t be doing that again, will we?” that sometimes come out of a parent’s mouth when they are sick of your shit and definitely told you so.

                2. Shannon*

                  There’s no “we.” It’s the OP’s decision whether or not to approve his vacation, so she should take responsibility for that decision.

  3. Seal*

    Is there some reason you can’t institute some sort of no/limited time off policy for your busiest months, coupled with regular reminders for people to schedule their vacation time wisely so they don’t lose any? Otherwise you may be facing the same thing again this year, despite Bob’s promises to not do it again.

    1. sunny-dee*

      Yeah, I’ve definitely worked on projects where a team lead or manager had blackout dates (usually in the 4-8 weeks before a major software release). Not always, but if it was recognized that there were a lot of issues out of beta or a lot of unfinished features or testing. My friend who is a bookkeeper has a similar thing for March and April. It’s not an unreasonable request, especially with months of notice.

      1. TootsNYC*

        I agree. I let my team know when our monthly crunch times, and it’s clear these are not available. On very rare occasions, my folks will come and say, “It’s my sister’s wedding!” and then they’re OK to go, but they know how big a deal it is.

        Be open, be early–and let Bob figure it out beyond that.

        I remember my mom being appalled that I couldn’t take vacation during a crunch time (at the time, I was at a place that only had 4 crunch times in a year), and I said, “Mom, those four time periods are the ONLY reason there’s a job for me. If I’m not there for them, why would they keep me on?”

        1. Green*

          I’m glad you’re still flexible on blackout days. There are some things that people don’t get to plan. :)

        2. Petronella*

          My mom (in a unionized government job for her entire working life) was similarly mystified when I told her that I had to work at certain times and couldn’t take vacation anytime I wanted. It’s a generational thing, like not taking your parents’ advice when job searching.

          1. doreen*

            I don’t think it’s a unionized thing, a government thing or a generational thing. Because my 75 year old retired union/government employee relatives certainly did not get to take vacation anytime they wanted throughout their entire working lives. It’s true that those sort of jobs often don’t have “crunch times” where no one can take vacation , but it’s also not uncommon for vacation approval to be based on seniority in those jobs. Which often means the people on the bottom of the seniority list end up with a week off in April and another one in October because that’s what’s left.

        3. Ad Astra*

          My mom was similarly appalled when I was working as a sports copy editor in a Southern college town and I couldn’t get any Fridays or Saturdays off during football season. (In her defense, she’s decidedly not a sports person, so the significance of Friday and Saturday football wasn’t obvious to her.)

        4. Erin*

          I checked with my friend CPA’s to plan the best weekend for my April wedding. All were pleasantly surprised and basically said plan it and we will make it work.

      2. SophieChotek*

        Yes we have blackout dates too.
        We have some quirky blackout dates…which now that I check are not in my contract.

        And at my food service job that I work at weekends, there is a “request-off” calendar (which is first come, first serve)…which probably isn’t best practise (per reading here) but seems to be standard in the hourly food service place I work and has been for years, with slight preference for senority in terms of much-requested dates

    2. Raine*

      The original post indicated that in fact all travel, conferences, and vacation time is typically blacked out during this time frame. He put in the request late in the year for 4 straight weeks off when the OP was new, and the company wanted to keep him (and thought he was unhappy) so worked to make it happen.

      But Good God. He had to know even taking 1 day was a big thing during blackout days. And partly for that reason I suspect he’s stockpiling days and fully planning to do it again.

      1. Petronella*

        Agreed, he knew exactly what he was doing and will probably do it again if he can.

      2. Terra*

        That’s not necessarily true. In the original post it was clarified that the person in question was a temp to permanent so depending on how that was handled they 1) may not have know about the blacking out before hand and 2) may not have had a choice in that if they were made permanent and earned the vacation time that they then had to use right before the end of the year or lose it.

    3. Lee*

      But this company’s busiest month is December. What kind of company of has a “use it or lose it” policy, then limits vacation in December (the last month to use your days off)?

      1. Sciencegirl*

        I think a problem could arise here if too many people decided to take vacation during the time of year that they all know is the busiest. Blocking it out for everyone seems more fair than allowing some but not all to have vacation during this time.

      2. AnonInSC*

        Doesn’t matter – that’s the reality for this company and the OP can’t change it. And it sounds like something everyone knows…so people should be able to plan accordingly.

        1. AnonInSC*

          I should add that I do agree it stinks. But I can see how vacation time needs to be managed during the rush. That it coincides with a time that people traditionally need more time for travel etc is rough.

          1. Lee*

            It also coincides with the last month for a “use it or lose it” policy for vacation days. Also, has this company never heard of temps?
            Futhermore, I highly doubt the CEO and higher-ups were:
            -working 12+ hour days for almost 7 days a week for months
            -not taking vacations during this time period

            This whole thing just rubs me the wrong way.

            1. Kyrielle*

              Rubs me the wrong way too, but OP was pretty clear about not being in a position to change that policy.

              And temps don’t work for everything! The product I worked on most recently at $LastJob required software engineers who were up to speed on the product – a training cycle that generally took 9 months or more, depending on the person and their prior experience. For the first 3-6 months, the person would be a net drain on the team. Bringing on a temp for a “crunch month” would be a very bad mistake.

              Even customer service staff and trainers for that product needed a month or more to come up to minimally useful speed.

              Plenty of roles do lend themselves to bringing on temps, but others really don’t, even if you have the budget for the temps.

              1. Kyrielle*

                Hmm. I wish I could edit or remove my comment; temps don’t work for everything sounds too much like “not everyone likes sandwiches”, and I apologize. I just wanted to highlight that it may not be a case of “haven’t they heard of temps” but that in some cases, companies may have heard of them but decide for very business-legitimate reasons that a temp cannot solve the crunch.

                Still, if it’s an area that a temp *could* help with (even if they could only help with the routine stuff, for that matter), it could be another good avenue to explore.

                1. Ask a Manager* Post author

                  No, I think your point was well worth pointing out in this case, because people often do suggest temps as being an across-the-board solution, and there are many jobs where a temp isn’t feasible (which I don’t think people always realize, if they haven’t worked in those jobs).

                2. LBK*

                  Yeah, I think there’s many roles where by the time a temp got up to speed enough to be useful, the person would be back anyway. For work that sounds as intense as what the OP describes, I really doubt it makes any sense to bring in a temp just for a month. Usually those kind of super-short temp gigs are tasks that are very simple but time-consuming, like “We need someone to go through 5000 returned letters and update the addresses in our database”.

                3. Green*

                  I had 2 months of just training when I joined my company in my role. We have a few contractors (i.e., retired employees and one who moved and does occasional freelance work), but otherwise that’s not an option, so it’s a fair point.

                4. Kyrielle*

                  I still would have liked to say it better than I did, but I’m glad the point is at least relevant enough to pass the test with others. :)

                5. designbot*

                  I wouldn’t apologize for that. In my field people think that freelancers are the balm for everything, but in my experience this has only worked when the company has a sort of stable of freelancers that have experience with us. If the regulars aren’t available and we have to interview and hire completely new ones, it’s more trouble than it’s worth.

              2. AdAgencyChick*

                It’s not just that temps may not be able to handle the work (they are a frequent solution for crunch periods in my industry). It’s that:

                1) if the staff as a whole aren’t spreading their time out during the year, *everybody* wants to take off time in December — and then the company’s payroll suddenly takes a huge leap in December, because they’re paying the salaries of the staff who are on vacation, plus the hourly rates of an army of temps
                2) Good temps are in short supply, and because busy December is an industry-wide phenomenon, you may not be able to book enough of them to fill the gaps. I had a *devil* of a time getting enough freelancers last year to cover for people on my team who were out!

        2. OP*

          To clarify, busy time for my *department* is in December. That’s not necessarily true for the thousands of others who work for the company. For example, May through September is the busy time for another department. You can’t please everyone. And to another commenter’s point, our FY is same as the CY, so the use-it-or-lose-it tracking makes sense to use FY/CY.

      3. Just Another Techie*

        I agree, it’s crappy, and if the OP has the standing to do so, she should advocate to get the policy changed. But since she can’t single-handedly change the policy and has to work with it, it’s best for her to be crystal clear with all her direct reports that she won’t approve time then.

      4. TootsNYC*

        Were I HR, I’d be lobbying to set the beginning of the “year” as June or July.

        (I’d like to se the beginning of my week as Wednesday, so that if someone needed a ton of hours on Friday, I could adjust their schedule to cut back on the next Monday or Tuesday.)

        1. Rater Z*

          Where I work (a big box store/chain), the benefit period for each employees starts on their anniversary date. For me, it’s July 24th. If I don’t take my vacation time by then, I lose it and start over with the next year’s allotment of hours I can take. I’m part-time but work enough to get 143.75 hours this year and I still have 90 to take. Since we are retail, they black out the weeks from early November to the end of the year because of the Christmas period. They also, within the past couple of months, set up a new policy of planning schedules for two weeks out so we have to ask for time off at least two to three weeks in advance. I usually hold most of my time until the end because of my wife’s health and not knowing if /when I will need the hours off. This year, losing the supervisor in mid-March and not getting a new one until this week complicated everything in planning. (I have the other 90 hours planned out now for days I don’t work anyway–which they accept and pay for).

        2. Creag an Tuire*

          Agreed. At my current job, our busy seasons coincide with the beginning and end of the K-12 school year, so our “year” starts in September; as you might assume summer is our slow season, so if you haven’t used any expiring vacation days by September 1 you have no-one but yourself to blame.

      5. Koko*

        It might not make sense for them with the way their payroll and accounting is setup to have vacation formally expire on Nov 30 if their fiscal year ends on Dec 31, nor does it make sense to move the fiscal year just to accommodate vacation expiration dates vis a vis the busy season.

        It’s fine for employees to just know that the “practical” expiration date is November 30 even though their paystub won’t reflect the expiration/rollover until Dec 31.

      6. Paris*

        My company has a use or lose it policy and we have blackout dates from mid-October through December. You are explicitly told you have to take your vacation prior to mid-October.

      7. Roscoe*

        That my big thought. If you are going to do that, you shouldn’t have December be when you need to use it. Because essentailly you are saying, use it or lose it, but only in these 11 months, and no holidays for you. Seems pretty crappy to me.

        1. Rafe*

          In DC, December is a crazy crunch month for all sorts of different types of jobs — partly because Congress is usually passing last-minute bills, and if it’s a tax bill, for example, computer programmers at the IRS have to work nonstop to accommodate the system before tax season starts, and so do all of the tax software preparation businesses like TurboTax and H&R Block and everything. That’s just a teeny tiny example. It seems like I’ve heard end-of-year business records are a nuthouse thing in finance. I mean, yes, without question there are jobs in the private sector and in government where those people who go into that field know there are entire months that are basically blacked out.

      8. Rusty Shackelford*

        I don’t see what the issue is. It’s not like they dropped this information on him in August, when it might have been too late for him to do anything about it. You have X days of vacation you can use this year. Do not use them in December. Why is that impossible?

        1. Dot Warner*

          I agree. I don’t see why so many people are defending Bob. He knew that December is the worst time of year for the company and that taking vacation at that time would leave everyone else in the lurch, but he chose to take his vacation then anyway. I’m sure Bob’s family will miss him at the holidays this year, but you know what? Everybody who had to work 16 hour days to cover for him has a family too. And heck, if Bob goes to visit his family in October instead of December, his plane tickets will probably be a lot cheaper.

          1. DoDah*

            Because those who are defending are also defending their own actions. PS these are people I would not want on my team.

          2. Evan Þ*

            The original letter, and OP’s comments, explain that Bob’s family lives on the other side of the world, so the holidays are the only time he can take a 3-week vacation to see them for a substantial time (which, given the cost and duration of plane flights, matters.) Also, last year, he only was hired full-time in August – so the information probably was dropped on him then.

            1. Dot Warner*

              Yes, I read the original letter and comments. Bob may not have had vacation time a year ago, but he was employed in OP’s department then and surely would have seen how busy December is for them. He chose to take vacation then anyway and his coworkers – who also have families and lives outside of work – had to work 16 hour days to cover for him. I’m betting OP wasn’t the only one whose marriage was adversely affected the workload.

              I get that international travel requires an extended amount of time, and it certainly is difficult to be on the other side of the world from your family, but his vacation prevented his coworkers from enjoying their families. That’s not OK. If time off at the holidays is a non-negotiable for him, then he just isn’t a good fit for this role.

      9. Chocolate lover*

        If you know that in advance, then you plan for it.

        And not every place uses calendar year as the deadline – or fiscal year and vacation time operate from June to July.

      10. CoffeeLover*

        Why not use the fiscal year rather than the actual year, if your blackout period is in December? My company uses fiscal year benefits rollover.

    4. Anna*

      At a past job we had court mandated deadlines we had to keep, but so many people took so much time off around December we’d inevitably fall behind. Manager finally made a policy that no one person could take more than 1/3 of their vacation time during December (we were also a use it or lose it).

  4. misspiggy*

    I do hope the OP considers leveraging his achievements into a new job somewhere which doesn’t expect people to work huge hours to make up their colleagues’ holiday time.

    At the very least, the OP should make clear the high personal cost of achieving the last set of deliverables, and negotiate a significant bonus or pay increase if similar performance is to be expected this year.

    1. Stranger than fiction*

      Totally. Op I’m so sorry you had to work 16 hour days! You basically did nothing but work and go to bed :(

    2. Long Time Reader First Time Poster*

      Yeah, I’m kind of sideeyeing this company, to be honest. When people are out on PTO, there need to be better ways to support that absence than forcing a 40 hour a week employee to work an 80 hour week!! Yes, even during busy periods. Have a plan in place to hire a temp — you never know when one of your employees is going to be hit by a bus or otherwise out unexpectedly for a long period of time, even if you do crack down on PTO.

      And in the OP’s place I’d sure as heck be managing up to ensure that I’d *never* be expected to pull that kind of herculean effort again.

      1. Jeanne*

        I agree. This can’t continue year after year. OP will end up divorced and hospitalized. It’s not worth it. If the whole team was overworked, I suspect even having Bob there won’t help enough. Start talking now about those deliverables and how to balance things better. OP is right they’re going to expect miracles again unless someone speaks up.

      2. OP*

        To be fair to my company, I was new in my role and these were company-specific deliverables. My boss and coworkers kept saying what a big deal it was. No one did a great job of explaining what the bar was for success. I certainly didn’t want to risk under-performing, so I went all the way in the other direction. Looking back I didn’t need to put in so much effort (I feel my average-level deliverables still would have been seen as above-average in this case) but I had no clue and nothing to compare against. Of course now, I’ve set a bar for myself and higher-ups expectation of me, so I’m having trouble figuring out how to scale it back for next year. Prep starts in July!

    3. TootsNYC*

      Well, one of the challenges for the OP is for her to figure out how to achieve that same result using Bob’s labor–since that’s what was missing. If she’s got Bob’s hours and skill, it ought to be possible.

      But i do think it would be wise for her to forecast this for her higher-ups, so that they are prepared to view that as being just as big a success for the OP as all her single-handed work was.

  5. AdAgencyChick*

    I responded to the OP feeling her pain and got drubbed a bit for some of my views — I very much want people to take their full vacation allotment (not to mention use all of mine too!), and I also HATE HATE HATE when people don’t plan well, causing me as a manager to have to either be an ogre and decline a request late in the year, or else sacrifice the needs of the business (or, as OP did, be the person who takes on the brunt of the work to accommodate an employee who requests vacation during a busy period).

    I think there needs to be consideration on both sides. The busier a period is going to be, the more important the timing of the trip had better be in order to ask for that time. Three weeks for your wedding and honeymoon while the rest of us are in launch mode and doing shifts so that we can have 24-hour coverage? Go with my blessing — I’ll find a way to deal with it. Three weeks to visit family in a faraway country? Okay, but I’m going to at least ask if there’s another time of year that would work well for you.

    If your reasoning is that you need to take three weeks off in December because of the use-it-or-lose-it policy, and you just didn’t plan well, I am going to be annoyed. Possibly annoyed enough to say no. Like OP, I work in an industry in which December is the busiest time of year, and like her I work at a place with a no-rollover policy that I can’t change. And like OP, I ended up covering more than my fair share of extra work in December because employees hadn’t planned their PTO well. (In my defense, I started the job late-ish in the year, so I was not able to have “plan your PTO” conversations in the first half of the year.) OP’s situation sounds far more extreme than mine was, so I feel for her. A lot.

    Anyway, I have had “plan your PTO” conversations with my employees a couple of times this year already. I noticed a tendency of commenters in the earlier thread to say that the manager should be reminding employees on a regular basis. Is that true? I’m asking. I think my employees are grownups who should be able to be told once or twice, and then do the planning, or else face the consequence that they may be told no.

    I promise, I HATE saying no to vacation requests. HATE it. But I continue to sympathize with OP, and since it sounds like Bob is not paying attention to regular reminders to use his time off, I will sympathize with OP if she has to turn him down at the end of the year.

    1. AdAgencyChick*

      To add: I also firmly believe that once I’ve approved vacation time, if things become busier at that time than we expected, it’s my problem as a manager to cover that. I would never attempt to solve the problem by asking the employee to reschedule.

    2. Nova Terra*

      I used to work at a very large company where all employees were required to submit their vacation requests for the year by mid February. Of course, they weren’t set in stone–you could still request changes and the like–but all changes were done at the discretion of your supervisor. There were blackout periods too. Given that, I’m having a really hard time dredging up sympathy for people like Bob…if you don’t have already have vacation plans, you could make some?

      And AdAgencyChick, I think it’s reasonable to expect adults to be on top of their own vacation planning. I wouldn’t want my managers to constantly remind me about vacation. I’m now also in a company with a use-it-or-lose-it policy, and everyone plans their vacations accordingly.

    3. Wakeen's Teapots, Ltd.*

      Our busiest month is September. We have standard 3 week blackout during that month where nobody can take vacation and we make sure that everybody knows it.

      (Can nobody really take vacation? If you’re the maid of honor in a destination wedding and you need to tack two vacation days onto a weekend, yes, we’ll work with you. There’s always someone who needs some kind of accommodation every year but pretty much nobody can take vacation those three weeks, everybody survives getting to chose from the other 49 weeks of the year.)

      December is our slowest month. We can let everybody have all of the time they want in December, if they have days left (as long as there’s a skeleton crew in every function). Works well because half of the people want to use as much time as they can in the summer (so they don’t have that much time left in Dec) and half of the people want to see how close they can get to the whole month of December off.

    4. GeekyDuck*

      I agree with you in the broad strokes. I think we should expect people to act their age and not their shoe size, and as such plan their own PTO without having to be babysat.

      The area where I don’t know if I agree is this comment:

      “Three weeks for your wedding and honeymoon while the rest of us are in launch mode and doing shifts so that we can have 24-hour coverage? Go with my blessing — I’ll find a way to deal with it. Three weeks to visit family in a faraway country? Okay, but I’m going to at least ask if there’s another time of year that would work well for you. ”

      I think this comes dangerously close to policing people’s private lives. Where do you draw the line? A wedding isn’t an emergency and doesn’t crop up overnight so the person should have been able to plan around whatever the job’s Hell Week/Month is. On the other hand, my grandma was diagnosed with cancer and her last family Christmas is an important thing — visiting my family is my top priority.

      I’d personally be more comfortable saying “unless this is an emergency leave, vacation time during X window is limited to Y and Z conditions. We’re too crunched otherwise.”

      1. LBK*

        I don’t think asking someone to justify an exception to a rule (like taking time off during a blackout period) is policing someone’s private life – it’s a unique situation because it’s not just asking for time off, it’s asking for special treatment, and there needs to be some level of explanation for why you need that special treatment.

        1. LBK*

          (And I think that contrasts with asking for an explanation every time someone takes any PTO off, because just taking PTO shouldn’t be considered a special request. It’s only because it’s asking for time when you’re not supposed to take PTO off that it matters, because if there weren’t a requirement to justify that time off, everyone could just take it, which would defeat the purpose of the blackout.)

          1. AdAgencyChick*

            Exactly this. Want to take two weeks during a slow period? Be my guest. I don’t care whether it’s for a trip to Japan or for an Akira Kurosawa marathon in your PJs. Ask me for two weeks in a row in December, I’m going to want to know that there’s a good reason you can’t take that time in one of the other 11 months of the year.

      2. sunny-dee*

        Well, stuff happens. In software, I’ve had projects slip as much as 6 months from their original date. Almost always, that means there were big design flaws that require a lot of extra work to fix and those are the projects that result in blackout days leading up to release. But you could have someone who planned a September wedding assuming their project would release in April. (That actually did happen to me, though I only took a week and a half off.)

        1. Stranger than fiction*

          Yeah, the thing with wedding is, sometimes there’s no one date that works for the bride, groom, and their families. So you could end up being the one that has to have that awkward convo with the boss about taking time during a blackout. Of course, you still don’t book the reception hall til you have that cleared (if possible, we’ve also read here about managers that take weeks to approve requests).

        2. Alter_ego*

          This happens to us all.the.time. I have a coworker who had three major projects in a row whose deadlines got pushed to the week he’d deliberately scheduled his vacation to be after the project deadline. It sucks for those left behind finishing things while he’s on a beach somewhere, but he did his best to accommodate the schedule, he can’t help it if the deadlines change

          1. AdAgencyChick*

            Completely agree; that’s why I made an addendum above. Once I as a manager have said yes, any coverage problems become my problem, not my employee’s. I know there are industries and managers who expect employees to be “flexible with” (read: willing to give up) their vacation time after it’s been approved, but I definitely draw a line there.

    5. LBK*

      Can you check people’s PTO balances a few times throughout the year and send out targeted reminders just to the people with a lot left? I think that’s a bit less paternalistic than sending out constant blanket reminders. And I don’t think a “regular basis” has to be more than a few times a year – I’d say once per quarter.

  6. Sami*

    What about having a policy that time off in December (or six weeks before your deadline or whatever makes sense) must be requested and approved by ___ date? That would force employees to make time off and vacation plans well in advance.

    1. Anna*

      But it doesn’t address the amount of time being taken off. If Bob sends his three weeks in by that date, he would reasonably have an argument for them being approved since he met the deadline. OP needs something else. Either a blackout period or a policy that an employee can’t take more than X amount off during their busy period.

      1. Sami*

        True. Add a limit to time off during this period AND make requests due by a particular date.

  7. animaniactoo*

    Seconding blackout dates. My company has them along with a use-it-or-lose-it policy.

    In the main, the blackout dates vary by division, but I know that I can NEVER schedule a vacation in the month leading up to and during the Annual Major Teapot Convention, or the Annual Tea Cozy Convention. Those 5 weeks each are completely blocked out. The week right after is also not great because even if not specifically blacked out, we usually have a high number of initiatives that come out of those conventions.

  8. Mae*

    I can sense the frustration on both sides here, to be honest. Four weeks off in one shot is significant, and furthermore inconsiderate if this request is indeed resulting from a lack of planning on his part. No one should have to work upwards of 80 hours a week. However, I sense resentment in your tone, and it seems as though you want to castigate this employee in a sense, which isn’t really all that effective. So what can you take from this? Suggest a change to the policy in writing. Most employees truly believe they are entitled to take the vacation they’ve accrued as they please. If there are blackout dates or a max cap on how much you can take at once, that needs to be explicitly stated, otherwise you have no footing to go on other than your own preference.

    Devil’s Advocate: I see Bob’s perspective because, I, too, have family overseas that I miss and need two weeks at a time to go see due to various factors, including the expense of international travel, etc. Also, like me, it sounds like Bob is one to work his a** off for months at a time and then take longer trips as opposed to people who just take staycation days here and there. It could also be that the holidays are the best time for his personal reasons to see his family. I mean, who doesn’t want to be with their family around the holidays. I get it- not your problem. But I think you could have been more proactive with planning on policy on your end. Resentment will grow if he continues to feel guilty for having taken all that time off- and if you project your own frustrations onto him to try and perpetuate that guilt.

    1. Just Another Techie*

      Most employees truly believe they are entitled to take the vacation they’ve accrued as they please. If there are blackout dates or a max cap on how much you can take at once, that needs to be explicitly stated, otherwise you have no footing to go on other than your own preference.

      This has not at all been my experience. Nowhere I’ve worked has ever had formally written blackout dates or caps on how much you can take at once, but I and my colleagues have always understood that you don’t take off and leave your team in a lurch the month before you launch the satellite you’ve spend the last year building, or the weeks before a major consumer product release, or whatever. It’s unprofessional and inconsiderate, and will make everyone in your department think ill of you, which certainly won’t help when it comes time to do 360s and allocate bonus money.

      1. Mae*

        No, I completely hear you. I’m not condoning what Bob did, but I was genuinely trying to see it from his perspective as there are two sides to every story. I’m a big proponent in general of having such protocols documented. My organization already has a month-long blackout in place for this fall, of which we were all notified company-wide months ago. Why is this so hard to implement? I don’t think it’s enough to rely on people having common sense and common courtesy. This is why backing up with documentation helps such matters.

    2. Wakeen's Teapots, Ltd.*

      Not meant to disagree with your point entirely:

      If I had to tell a marketer or a catalog artist that they couldn’t schedule two weeks of vacation directly before a catalog deadline, they wouldn’t have a job. It’s never happened, I don’t think it would ever happen, but if it did, I’d fire them.

      My point being that there are some or even many jobs that come with the responsibility to think for yourself and plan your vacation around your workload, OR your workload around your vacation. What has happened is a marketer moving a December deadline up by a week and a half so she could take the days she wanted . That’s smart! And nothing I had to think through for her (just she just had to get buy in from the rest of the team for the closer deadline so she could get her days.)

      1. Kyrielle*

        Yep. If I can’t take a week off in December, I need to know that well in advance, because there’s…nothing happening that I’m aware of special in December.

        If I worked at a Destination Resort with a special Holiday Magic thing going on, I would have a very different view of the odds of that December vacation. (But you can bet I’d be talking with my manager about whether a January vacation to recover from everyone else’s December vacation was a plausible thing, because I’d be _flat_ by the time that ended, I suspect….)

        The major release of software I work on before the major tradeshow in my industry? Yeah, probably I should not plan to take a lot of time off leading up to that….

      2. Mae*

        “If it did, I’d fire them.”

        To clarify, are you implying that said employee should be fired for asking?

        1. Wakeen's Teapots, Ltd.*

          I don’t approve or disapprove vacation days in that work group/level. People just let me know when they are taking and that’s it.

          If Glenda said, “I’m taking xx for vacation”, I’d say “sure”.

          The assumption in those roles (never once proved wrong) is that the people in the roles are aware of their deadlines/responsibilities and scheduling around them. Somebody who can’t handle that level of autonomy doesn’t belong in one of those roles.

        2. LBK*

          Not to speak for Wakeen, but at the very least I’d have a serious conversation with that employee about being cognizant about the needs of the business. It would show a pretty dramatic lapse in judgment.

          1. Wakeen's Teapots, Ltd.*

            Catalogs cost between $100k and $250k an edition and each one is responsible for driving X million in business, which a whole bunch other people’s jobs depend on.

            Anyone who isn’t capable of managing their own vacation time around their responsibility to the deadline, isn’t ever working on another catalog at Wakeen’s.

          2. Petronella*

            Exactly, if an employee has the bad judgement and obliviousness to even ask for (non-emergency) vacation at what they know is the regular crunch time…that’s a data point. It tells me something about how seriously they take the job and what kind of team member they are. What would you think of a tax accountant who asked for 4 weeks off in April?

            1. anonintheuk*

              I am a tax accountant, and the UK filing deadline is 31 January.
              I will approve leave for my staff for the days off between Christmas and New Year, or for a couple of days before Christmas, so that everyone gets a decent rest and to see family. If you ask for time off in January it had better be an emergency.

              A few years ago someone in this area asked to take a week off to go skiing in January, Her employers turned the request down on the basis that they were too busy and ski slopes in Europe are open, usually, until mid-March. She took the leave anyway, so her employers took legal advice while she was away, and she was out of the office within 20 minutes of her first day back. She has since left this field, because she could not get another tax job.

    3. Roscoe*

      I too sensed some resentment in her tone. I thought I was the only one. It seems like she is saying “He feels guilty, and he should feel guilty”, with a subtext of we made him feel guilty. The guy has family overseas. That is a big deal around the holidays. My family is a half hour away, so I never have a problem working a bit more so people can just take an extra day at home. But this place essentially is saying that he can NEVER visit his family at the holidays. Frankly, that sucks. I actually feel ad for him.

      Now this doesn’t take away from the business needs. So in that, I agree, you need to have a written policy. I’m not a fan of the “its a known thing that you can’t do x,y,and z at this time of year” If its known, make it a policy.

      1. Mae*

        Exactly! I thought I was the only one, too. This also runs into the territory of being entitled to feel like a martyr. I hope for everyone’s sake, this whole thing is not held over Bob’s head.

        1. Roscoe*

          Yes. She is making herself a martyr. Bob wanted to see his family, his bosses okayed it, and she was forced to work absurd hours, but they payoff was worth it. But Bob = bad guy. I bet its already being held over his head, if not blatantly then in small ways.

          1. LBK*

            It wasn’t quite as simple as that, though, because you’re ignoring the part where there was serious deliberation about whether Bob should be allowed to go. I think your explanation makes it sound like there wasn’t any consideration beforehand to how this might impact the department, so therefore it’s not Bob’s fault if they approved the request and then discovered that it would actually screw them over if he left. They knew and they tried to do the right thing by letting him take the time since there wasn’t any policy to the contrary, but that doesn’t mean Bob gets off scot-free from the consequences of his decision just because there wasn’t a rule in place.

            1. Wakeen's Teapots, Ltd.*


              IDK, different workplace cultures are different I guess but at Wakeen’s, we don’t leave co-worker’s hanging, and everybody seems to get all of their vacation they want just fine also. It’s about working together and cooperating with each other.

      2. LBK*

        Well, wait, I don’t think this means he can never see his family at the holidays. I get that if you’re going to do international travel it makes more sense to do it for a longer period of time, but 2 weeks would still be plenty and be much less of a stress on his coworkers than 4.

        But moreover, I think this is kind of just the circumstances you accept when a) you move somewhere away from your family and b) you take a job that’s extremely busy around the holidays. If you take a retail job, you can’t get indignant that you never get to take Black Friday off – that’s just part of the job that you signed up for.

        I also don’t think the OP is wrong if she feels resentment towards him. She should be allowed to feel resentment – he left her in a lurch that seriously impacted her, to the point that it even impacted her relationship! This isn’t “my coworker did something annoying that I got over after I ranted about it for a few minutes over drinks after work”. This is “my coworker made my work life miserable to the point that the effects bled over to my personal life.” Having actually gone through something similar to the OP last December/this January (my hours weren’t quite as insane, but pretty close), that takes a serious, long lasting toll on you. It can take months to feel totally rejuvenated and refocused, and often it leaves a permanent mark on your work ethic. It’s not a consequence that should be considered fair and balanced in exchange for Bob getting the schedule leeway he wants.

        I didn’t read her explanation as being a martyr, but rather to show that there were genuine impacts to the business as the result of Bob being out for that long (because often when subject of someone wanting to take a long vacation comes up here, people argue that one person being out doesn’t usually have as much of an impact as it might seem). I don’t think it’s fair to discredit the way this has impacted the OP – PTO is not a god-given right that should be allowed no matter the consequences, even if you don’t have a written policy. As I said above, taking this much time during the busy season shows a serious lack of judgment on Bob’s part, and I’d be questioning in what other ways he’s being myopic about his role in the department.

        1. Roscoe*

          PTO isn’t a god given right, but it is a company given benefit. Again, I’m not saying that there wasn’t a business impact. And its unfortunate what happened to OP. But I don’t think blaming Bob is entirely fair either. He made it clear that this was a big deal to him when he was hired. Requested the time off. And it was approved by OPs manager. The deliberation that went into it is neither here nor there, it was approved because they found him very valuable. She should resent her boss, not her subordinate. But she can’t take out that resentment on her boss, so Bob is a much easier target. Getting made at people for taking a benefit they have earned is never something I’ll be behind. If it makes my job harder because someone else is taking it, I’m going to be annoyed at the people above me for making that situation what it is. I had a job once teaching where basically anytime someone took a sick day, they would make our technology teacher sub (to save money), well that meant someone else lost their prep period for the day. It was their way to make us mad at the person taking the sick day, but the point is, we should have been mad at them for cheaping out.

          1. LBK*

            I don’t think the blame is totally on Bob either – if you go back to the letter a few weeks ago about the coworker who blocked off all the days around holidays when only one person was allowed to be out at a time, I was staunchly defensive of the position that it was management’s fault for having a short-sighted policy. But in that case, the problem was more that the policy allowed Jane to violate the social contract, which makes her a bit of a jerk but it doesn’t necessarily say anything about her as an employee.

            There’s a professional expectation that good employees will manage their own workload without needing oversight. I think that includes ensuring that your availability aligns appropriately with how your business operates; on a smaller scale, this means things like working longer hours during a busier cycle, which may be balanced out by working shorter hours when it’s slow. On a bigger scale, this also means understanding the schedule and seasonality of your workplace and planning your PTO accordingly, and I think that applies whether it’s explicitly written into the policy or not. For example, I have critical tasks that have to be done on the 4th business day of every month, otherwise it can potentially screw up payroll for our entire sales division. It would make me look completely oblivious about my responsibilities if I requested that day off, at least if I did it without first ensuring I’d have a backup available and making it clear that I’d planned accordingly when I made the request. There’s no policy that requires me to do that, but good employees proactively consider the impacts of their decisions, and that applies here as well.

            What it comes down to is that I can’t picture a truly high performer thinking it’s acceptable to take off a huge chunk of time during the busiest part of the year whether it’s allowed by the policy or not. Sure, Bob technically didn’t break any rules, but he showed that his priorities are out of sync with his role in the department and that he wasn’t thinking of the big picture, neither of which are good signs.

      3. Temperance*

        You don’t move several time zones away from your family without realizing that you won’t be able to see them for every Christmas.

        I think it’s really unfair if he keeps getting off for long periods during the busy season because of his particular situation. Everyone else gets punished by having to work longer days and by not getting time off at the holidays.

        1. Roscoe*

          That may or may not be true. Everyone may not get as much time off, but if their family is in the area, they can still see them at the holidays.

          1. LBK*

            I think Temperance’s point was that if we accept Bob’s family situation as always justifying extra time off in December, that means the office will always be short-staffed during the busiest season, which isn’t really fair or sensible for the business.

            1. Jayn*

              I read it that way as well. I haven’t seen my parents near the holidays in years. On our end we’ve had various reasons not to travel–on theirs, my father cannot take much time off October-December. It’s just too busy for him (November he may not even take weekends off). And it sucks, but his business is super busy that time of year and i can accept that even though I wish it wasn’t the case. And I’m only a country away.

  9. TootsNYC*

    I want to encourage people to challenge this sort of assumption:

    “When Bob returned in January, I was so far deep into all the projects that I couldn’t utilize him for almost anything on these key projects other than very small supporting tasks. Instead, I had him focus on all of the “regular” projects that were dropping through the cracks during this busy time. As for me, my insane work schedule continued throughout January, until all deliverables had been completed in early February.”

    Sometimes people think that the work it takes to delegate is too much of a distraction for them to do when they’re busy, but its payoff can be huge, and you shouldn’t reject that out of hand.

    1. StudentPilot*

      I read that as “the projects were far enough along, that it would have meant spending more time than feasible to give Bob the background on the projects so that he could pick up and start working” not that the OP didn’t have enough time to delegate. I have this issue at work – what has been, why X isn’t being done, what has been tried and hasn’t worked, what we’ve decided to jettison due to time constraints, why A is being done (because it seems like such a weird decision, but if it isn’t B, C, and D also won’t work), how K will effect L, who is doing what….

      1. TootsNYC*

        Oh, I don’t mean to imply that in the OP’s situation, she was absolutely wrong–it’s just that I see this often enough IRL when I know it’s not actually the case. I thought it was worth reminding people.

        And, I think the OP was smart to sic out-of-the-loop Bob on all the everyday stuff, to keep that moving along.

        1. Anna*

          I thought the same thing. If your first thought about delegating is that it would just be easier to do it yourself, you may need to reassess.

    2. kk*

      I came here to say something similar. This is a mistake I see often in new managers or people new to running projects. They think that it will take too long to bring someone up to speed so they continue to do things by themselves. It’s even referenced in The Leadership Pipeline by Stephen Drotter as being one of the key things to learn in the first turn you make becoming a manager of people. Additionally there was a bit of self-congratulatory tone after this in the letter, see I did it by myself and got all these accolades, they think I’m the best employee at this job – go you, you did a good job but a little bit of humility will take you much farther in life than the big head you have developed from this success.

      1. JB (not in Houston)*

        I didn’t get that at all from the OP. First, they should be congratulating themselves for doing a good job. That’s really hard to do in those circumstances. But I didn’t get a “I’m so awesome” vibe from the OP at all. All of the OP’s comments about how the work turned out served a purpose other than talking about how great she was–it gave another reason why Bob is acting like he regrets being gone, and it is a reason why she’s worried that this might happen again in the future, because now that higher ups think that they can let this happen again and everything will be fine.

        1. So Very Anonymous*

          Exactly. There’s a potential good-deed-going-punished angle here, because while it’s great that the OP got so many accolades, there definitely could be a precedent set that Bob wasn’t really needed, after all. It’s the same issue with letting people work overtime without paying them: it then looks like the work is all getting done without any extra costs, when really, it isn’t. I don’t hear OP bragging; I hear OP taking credit for a job well done AND also expressing concern about the optics of having done well without Bob being there.

  10. Stranger than fiction*

    Ok I didn’t see anything on #2 yet , but my question to the Op on this is do you have access to these logs? Or anyone else? And did they get corrected, updated? This guy should definitely not be the only one who can access and edit this log.

  11. Mike C.*

    For workplaces that have “busy times” which tend to cause all sorts of problems, I’ve found that taking the down time to make a concerted and formalized effort to improve your processes leads to huge savings, reduced stress and increased morale. It’s a large part of my job to be honest, and I’ve seen huge gains made

    I understand that this isn’t a direct answer to Bob here, but there are a ton of problems that arise from having busy times, but it’s all too easy to only deal with what’s right in front of you instead of blocking out time to try and address the root causes.

    Look at your processes and find which ones are truly time sensitive and which ones are not. Can anything be done in advance or otherwise time shifted? Are there situations where errors (client or employee) are adding more time? Can automation be helpful in any steps to speed things up or reduce errors?

    Deal with your vacation issues now, but if you start asking those sorts of questions, (of both yourself and your employees) the issues surrounding vacations might not even matter anymore.

    1. Wakeen's Teapots, Ltd.*

      Or matter less, at least.

      I agree.

      Some things are customer driven (peak business), and there’s only so much you can do about that. Our marketing calendar and product cycles though, we’ve been able to smooth that out with a lot of concentrated planning (and years of experience.) What could be “hair on fire!” “work 15 hour days!” schedules aren’t because of good process, long range planning and cooperation.

    2. TootsNYC*

      I so agree!

      At my current job, I find it frustrating because we don’t do this in any larger way, and any efforts on my part to goose us into having those meetings is ineffective.

      After one extra-bad crunch time, I wanted to have a meeting, and it was really, really demoralizing (and infuriating) when the department that was a huge part of the problem said, “Oh, we’ve moved forward onto the second piece of this project, and we don’t have time to sit down for an hour and discuss what went wrong.” Like, they had time to be so badly organized that I had to work 18-hour days, 3 days in a row, on Saturday AND Sunday–but they couldn’t carve out an hour to discuss anything.

      1. Wakeen's Teapots, Ltd.*

        Can I sneak in my culture clash story, mostly because I know you’ll like it?

        Okay so we sell teapots via catalogs and online. At the time the story takes place, we had 8 catalog print editions on 3 brands, all with hard event driven deadlines, pretty small staff – just a handful of us. Sometime we crunched or sweated to deadlines but we never missed dates and never worked insane hours.

        Dude comes in from Fancy Larger Competitor. He had a small division set up for him adjacent to mine, sort of in competition to me. (SPOILER ALERT: I won that “battle” and was asked to have his stuff folded into mine a few years later, but not actually relevant to story at hand, just ya know, information.;) )

        Anyhoo, he also had a catalog schedule, also event driven. Fewer titles, but essentially the same thing (with the same 365 days a year, 24 hour days).

        His deadlines were: pandemonium

        Catalog deadline! Everybody needs to work this weekend! I’ll buy pizza, Saturday and Sunday! 12 hour days during the week! Cancel your personal plans!!

        My people were like………………..what? They started looking at me doe eyed and lovey, like omg you are the bestest boss in the universe. They’d never heard of such a thing as was going on across the way.

        (And, to make matters worse, dude sniped at me how I’d spoiled the culture here and it was ridiculous that he had to push to get people to work these kind of hours when Where He Came From it was completely expected and normal.)

        Same 365. Same 24 hours in a day. Pretty big difference.

        1. So Very Anonymous*

          Wakeen’s Teapots, I’m pretty sure you ARE the bestest boss in the universe.

          1. Wakeen's Teapots Ltd*

            While of course I am amazing ;), there’s no magic in this story. It’s straight to Mike C’s point. Every crisis crunch this guy and his team had was of his own making. I don’t think it was poor planning, so much as it was intentional. For whatever twisted reason, he believed this was the way Things Should Be Done.

            Maybe it made him feel important. Dunno.

            1. So Very Anonymous*

              I have to say, though, that it’s your clearheadedness and practicality that make me think you’re the bestest. I’d much rather have that than that kind of stirred-up Excitement! Crisis!

    3. DoDah*

      Yep. I’ve worked for companies who used Agile to get a handle on their workflow. I’m trying to implement it at current job–but they LOVE their EMERGENCY EVERYTHING mode.

  12. Alabama Vet*

    Whatever you do make sure you DOCUMENT your discussions, verification that he understands the parameters of December (or whatever time frame), that he understands he could lose his unused vacation (use it or lose it), and have him SIGN HIS ACKNOWLEDGEMENT. Keep this in his department file and ensure HR has a copy too. This worked extremely well when I had “issues” while commanding an Army unit.

  13. Kas*

    OP, I don’t have anything to add to how to manage Bob’s leave next time round – other commenters have it covered – but I want to make sure that *you* managed to get a good block of time off after these projects were delivered, and I hope that your personal situation is better now.

    As for your concern that this level of output will be the default expectation from now on, I urge you to sit down with your manager at some point and make it clear that you won’t be able to pull that feat off a second time. This could also include your input onto the company’s leave policies, as they did contribute to your overwork and stress.

  14. Ash(the other one)*

    Ok, didn’t see this in the comments to the OP, so:

    OP–yes, I would say you need to have the conversation with Bob. You also need to make sure the rest of the team is aware as well. I see two things:

    1) Other team members saw Bob did it last year and may be thinking they can do it this year (“But you let Bob do it and my issue is equally as important” syndrome.)

    2) Depending on your team size: If more people have similar vacation banks to Bob, how do you make sure all that vacation time is mostly accounted for prior to the blackout dates and make sure you still have the coverage you need for the rest of the year w/o any0ne losing time? Admittedly, this may not be a problem for your team, but I wasn’t sure, so I thought I’d mention it.

    I’m not saying everyone needs to pick dates ASAP, but I think the team as a whole should know that December vacation will not be approved barring emergencies, and that they need to be thinking about scheduling their vacation to accommodate that so that they don’t end up losing days at the end of the year.

    As an employee I’d want it plain and transparent early on (the earlier the better) so I know how to plan, and so I know no one will be doing the December vacation thing this year.

  15. Elizabeth West*

    He might be saving it for summer–lots of people take vacations then because the weather is nice.

    I’m glad it (sort of) worked out. I hope the OP got some time off after this crunch as well.

  16. JS*

    Seems like a bigger problem here is being overlooked: Staff is obviously short handed if OP had to come in at 5:30 am and leave at 9pm. Even if Bob was in town, one person couldnt lighten that amount of work load. Need temp or seasonal employees.

    1. LBK*

      Well, just doing simple math, that’s 15.5-hour days, which divides into pretty normal 7.75-hour days for two people. And having multiple people is usually more efficient – you get rapidly diminishing returns from someone who’s working that much, so one person’s 14th & 15th hours are going to be a lot less productive than two people’s 7th hours. My brain is basically mush once I cross the 12-hour mark.

      1. OP*

        Typically what was happening was that normal work hours, 8:30am-4:30pm, I was completely slammed with meetings. So 5:30am and 4:30pm and after was the only time I could work on the deliverables for this project. Unfortunately it wasn’t temp-style (repeatable, simple) work – it needed subject matter expertise which typically takes about 1 year to build. Had Bob been in the office, I potentially could have pulled him from all meetings to work on deliverables instead, or we could have alternated.

        What I’m trying to say is, I wasn’t giving 100% of time 15-16 hour days to these deliverables. But when I started making silly mistakes or found myself randomly staring off into the distance, that’s when I shut it down. Usually around 9-10pm.

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