carpool drama, employee time-off demands, and more

by Alison Green on July 27, 2015

It’s five answers to five questions. Here we go…

1. My coworker is making it tough for me to share a ride with our executives

I’m at an organization where we’re in a lot of transition. We have a consultant working with us, “assessing our skills and capacity,” and we have a couple of executives who seem to be wielding all the power without giving anyone else warning.

I was lucky to be selected for an out-of-town conference with a group of my coworkers, including the two executives, and with a long-time coworker, Glenda, who is consistently unhappy with our management. Glenda is a very intelligent, talented person at her job, and I do feel she has been unfairly treated over the years. Management seems to have a personal grudge against her.

When we found that we were going to the same conference, Glenda offered me a ride to the airport, which I happily accepted. A couple of days ago, our executives emailed all of us and said they will be driving carpools since all of us will fit in their 2 vehicles. This morning, Glenda stopped by my desk and said, “Well, aren’t you glad you’re riding with me so you don’t have to ride with them?! I already let them know you’re carpooling with me.” I tried suggesting we should both carpool with them, but she said, “Oh no, it’s no trouble for me.”

Ugh. I’m in a pickle. This conference was my chance to re-establish a positive working relationship with my bosses during a really rough time at our organization, but I think that refusing their carpool offer for no good reason is going to get me on their bad side right off the bat. On the other hand, I don’t want Glenda to think that one of the only people in the office who supports her is now trying to distance herself from her. Distancing myself would probably be the smart thing, but I would feel awful about it. What can I do?

Just be direct: “Actually, I’d really love the opportunity to spend some time with Jane and Fergus. I think it could be great for you to too, if you’re interested. Why don’t we take them up on their offer?” If she says she doesn’t want to, then you say, “Okay. I’m going to go ahead and do it. Thank you so much for being willing to take me though.”

2. Employee is demanding I approve time off at an inconvenient time

I have an employee who expects that he should be granted his vacation requests regardless of the impact it has on a very small department. His first set of dates were approved. He then submitted a second set, to extend his dates, and without approval went ahead and booked his travel. He is attempting to bully his way into having the additional time off.

In fact, he is demanding his birthday off as a Friday – Monday long weekend off with a degree of “entitlement.” His attitude is all wrong and he seems to care less about the impact his extended absence will have on the workflow of the department during a very busy period.

How do I handle this? And do I simply deny him both set of dates including the birthday, given the impact it will have on the department and not being able to function efficiently without him as it is a peak period?

Well, if it’s truly a particularly bad time for him to be gone and you can’t reasonably make it work without him, then you explain that and say no, and make it clear that you regret that’s the case. But if there’s any way to make it work, I’d try to — vacation time is part of your staff’s benefits package and while it’s absolutely true that there can be certain times where it’s just not realistic to take time away, in general you want your default to be to try to make it work if at all possible.

(Also, I’d want to know whether people are usually able to use their vacation time in chunks of at least a week at a time. If they are, and this is a rare situation, that’s a point in favor of your stance. But if you never really want people to take a week off or if you only allow it during very narrow windows, that’s not reasonable — small department or not.)

3. Correcting another company’s language usage

I work in Europe, and most of my job function revolves around my native English skills – I work in communications and content, and my duties include running a blog, handling social media, etc. For every job I’ve worked here in Germany, one of my duties is usually to proofread and correct presentations and documents.

Recently, an external company came to pitch us their services. I’ve developed an excellent rapport with our contact at this external company, Teapots Inc. I speak with him frequently and we get along quite well. During his pitch meeting, I noticed several obvious and distracting English spelling and grammatical mistakes in his PowerPoint presentation, as well as some odd wording. Given that Teapots specializes in content and text production, and they boast about their ability to provide “quality content in multiple languages,” I desperately wanted to point out the few changes. Not because I’m a grammar freak, but because I have a lot of respect for my contact at this company, and I worry that a template like this may be recycled and may hurt their pitches in the future.

He had sent me the presentation as a PDF, and after much deliberation, at the bottom of an email discussing other relevant business topics, I attached the revised PDF with a few minor corrections with a short disclaimer – “Your English is great, I don’t mean to insult you, I want to help you for future proposals,” etc.

I wanted your opinion on something like this. Normally I would never point out typos but given the language difficulties, as well as the nature of his business, I made a judgment call. What would you have done?

I think that was fine to do. There’s an argument to be made, though, that this company’s prospective clients are better off getting an accurate look at the company’s language skills, and you’ve just made it a little harder for them to spot potential problems. But I think it was kind of you to point it out, regardless.

4. I don’t want a prospective employer to confirm my employment with my current company

Will my new prospective company absolutely confirm my employment with my current company ? I’d rather my current company not know I am looking. Also, my current company is very small, with really no HR department. What can you say/suggest?

It’s very normal to ask that your current employer not be contacted since they don’t know that you’re looking. There’s no iron-clad guarantee that some crappy employer won’t mess up and do it anyway, but it’s highly unlikely.

5. Do you get sick time paid out when you leave your job?

If my employer fires you, do they have to pay you your sick time you accrued throughout your time there?

Sick time, no. Vacation time, maybe, depending on whether you live in a state that requires it.

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{ 412 comments }

{ 412 comments… read them below }

  1. Mike C.*

    Re: OP 4

    Have they never heard of a paystub or W-2? You can even blank out the amounts paid, but if it’s good enough for a background check, it should be good enough for them. What’s so difficult about this?

  2. Kara*

    OP #2:

    A “a Friday – Monday long weekend off” is considered an “extended absence”. I’m seriously glad I don’t work for your company. A 4 day weekend shouldn’t impact your department so much that you can’t give someone a long birthday weekend and if it does, then you need to seriously re-examine how your department is structured and how it functions.

    1. Kara*

      It’s obviously way too late for me to be posting anything. That first sentence should read:
      A “Friday – Monday long weekend off” is considered an “extended absence”?

      1. Artemesia*

        I understood that he was adding these 4 days onto an already long vacation. If not then it seems ridiculous to make a fuss about his ‘demanding’ these lousy extra two days.

        1. Apollo Warbucks*

          My understanding was the employee wanted to add on an extra day to an already booked block of time off and then book Monday and Friday separately.

          1. UKAnon*

            I had understood it like this too, but re-reading it I can see how the other interpretations come in. I definitely think we need a lot more information to start making any kind of judgment on this!

        2. Lisa Petrenko*

          That was a different request. He wanted his birthday weekend and at another time added days to an existing vacation.

      2. Desdemona*

        I think we need to hear back from the OP for more context. Do they work weekends, and he originally took Friday and Saturday off, and decided to make it a long weekend? Was he due back on Thursday after how long off? It’s kind of odd, because nothing she’s described sounds like an entire week was involved — he was going to take a couple of days early in the week and be back on a Friday after being gone, but then extended it to include the entire week plus a day? And when she talks about denying both sets, is she saying she’s going to take back the already approved time? Not enough information to be sure, but the way I’m reading it, her approach to time off sounds pretty stingy.

        1. JenGray*

          I agree that we need more context because I wasn’t clear on how the Friday/Monday was related to the other time off. I think it does make a difference on whether it is reasonable to deny the second request. I agree that adding a few extra days in most situations won’t make that much of a difference one thing that I think people are forgetting is that planning was done based on the first request. It is possible that another employee is taking time off beginning that Monday and it isn’t reasonable to have both people off at the same time. In my job, I answer the phones & another coworker is my backup. We could not be off at the same time. We aren’t short staffed at my job normally but if we were both gone at the same time then the company would be short staffed. I also think that the OP is focusing more on the attitude of the employee than the actual request which could be pretty bad- which personally would bother me more than the request. I think all employees should get their time off but also if the employer has been good at communicating than all employees should know that not all requests can be granted at the time the employee wants.

    2. Not Today Satan*

      Letter 2 is the result of the current culture of employers hiring the BARE minimum number of employees needed to function. In the vast majority of situations, it really should not be a huge hardship for one employee to go on vacation, even for two weeks. It really makes me sick how Americans get so much less vacation than people in other countries and then get grief for wanting to take it.

      1. BRR*

        In the end I think we need a little more information. I work in a small department and really the only rule for taking time off is out of the 4 of us, two need to be there but we can get by with one if it’s important. We just had one person out for three weeks and survived. But it’s kind of like the argument we usually use, what if he got hit by a bus/quit/did something that required being fired right away? You’d get by.

        That being said you should never book travel without asking first. It’s just respectful. As I mentioned, my boss approves all request unless too many others already have off (and we have a shared calendar). I still wouldn’t book first. What I’ve done is say “around this time I wanted to take off, I see nobody else has. Is it ok if I play around with dates for the cheapest flights and let you know?”

        1. AvonLady Barksdale*

          TOTALLY this. Someone junior to me on my team, who did not report to me at the time, booked travel before requesting the time off. She told me when she booked her trip because she was really excited, then she told me when she was going– right after a huge event for which she was expected to handle the reporting. D’oh! It was her first year with us. I helped her work it out and set everything up so someone only needed to plug in numbers, but boy, was that inconvenient. She never did it again.

          However… s&%t happens, so we made it work. If we had not been able to make that work, something would have been seriously wrong with us as a department. The following year, I booked travel during the same event for a group thing (no option on the dates). We made that work too (and I wasn’t responsible for reporting on that one, so it wasn’t quite as bad).

        2. LQ*

          Not being able to book a vacation without asking first seems like it crushes any ability to have a vacation with other people though. Unless you go on vacation alone you aren’t allowed. Because say I ask my boss and then the prices change and then we come up with new dates and then you ask you boss and the prices change and now it’s no vacation for you.

          Why is it so bad to be able to look at the calendar and go, this seems ok, and plan and then ask. Besides there are plenty of bosses who think unless you have already booked plans they might as well trample on your vacation.

          1. AvonLady Barksdale*

            Most bosses I’ve had are pretty reasonable, and most plans I make are made far in advance. The only exceptions have been group travel for chorus tours (my chorus in NY tours every two years), but even those trips are planned well in advance. It’s a courtesy to say, “These are the dates I’m thinking, is there one that would be better than the other?” and it doesn’t take much. I’m going on vacation next week. When I was making plans, I gave my boss a choice of two weeks and asked for his OK within a couple of days. No big deal on my part. And if you’re traveling with other people, don’t you have to coordinate with them, see which dates are best?

            1. LQ*

              Yeah, but see this is where I’m confused, like you are going with a chorus tour, do you get to say when it is? If your boss came back and said you can’t leave on Friday does that mean you don’t get to go?

              Yes, when I go with others I coordinate, but I don’t want to double the pool of people I have to ask when coordinating with, I don’t want to have to start copying my boss on the should we leave Friday afternoon or Saturday morning conversation, let alone 2-xx other people’s bosses. (I know that wouldn’t be how you’d do it of course! but essentially.)

              My bosses have been great, but usually I know the schedule and big obstacles (project rollouts, large events, large meetings, etc) better than my boss. I wouldn’t schedule something for the week of a big event say, but I might for 2 weeks after when I know it is going to be quiet.

              Where I have been at other places my coworkers schedules didn’t matter much and when they did we knew them, and where I am now everyone can see time off requests so I know if half the team has off already and wouldn’t request.

              Why isn’t this sufficient to go ahead and book the tickets?

              And if the boss is upset about the way time off is being requested why not have a conversation with the employee about it?
              (I really hope my boss does if he doesn’t like the way I’ve been doing it! Talk to your people! Don’t expect them to just know!)

              1. Colette*

                The boss doesn’t need to be involved in conversations about whether you leave on Friday or Saturday, but you should check with her to make sure it’s ok if you’re gone for 2 weeks in late July Before you book the tickets – because if it’s not ok, you will have to adjust after the fact. If you’re planning in advance, you can usually allow for a day to check with your manager without substantially changing how much you’ll pay.

                1. AvonLady Barksdale*

                  Agreed. This is all about advanced planning– I’ve never had a situation where something planned and approved well in advance runs into some obstacle that substantially changes my plans. For instance, I spoke to my boss before making plans for the vacation I’m taking next week– I ran a couple of weeks by him, he picked one, we’re good. There is work stuff that may come up this week, but my boss and team are now prepared to say, “AvonLady won’t be here, let’s do what we can without her,” or I can get coverage, etc.

                  Now, yes, sometimes things happen. If my boss said to me this week, “I need you here, you can’t go,” then I would bill him for my plane ticket– because I made that reservation after his approval. If I had gone ahead and made the plans without checking with him, then that expense is entirely on me.

                2. Kyrielle*

                  This. There are those things where the boss’s feedback is a go/no-go rather than a “gee, I better find another time” – but not many. (For example, if I want to attend a poetry workshop only available one week, either I get the week or I can’t go.)

                  But we’re doing two family trips this month, and I just approached my boss, expressed the amount and timing I wanted off for each roughly, my husband did the same with his, I booked the tickets, and we formally filed for the dates I got the tickets for.

                  It does depend on your boss responding in a timely fashion to such questions and being reasonably accomodating, of course. It might not work in all environments – but it’s been a functional paradigm in the places I work.

                  I’ve never tried to book a huge huge trip that involved lots of people, though.

                3. ineloquent*

                  I had a boss once who demanded that all vacation time be scheduled (including dates) in February for the whole year. She also almost denied me the time I needed to attend my sister’s wedding. As it was, she gave me two days for the whole trip, which required me to drive 16 hours to be there (wasn’t paid well enough to afford plane tickets for two). Awful boss, awful job.

              2. Adam V*

                > like you are going with a chorus tour, […] If your boss came back and said you can’t leave on Friday does that mean you don’t get to go?

                Yes, that’s what it means. You’ve got two options – you can either:

                1) work out some solution with your boss to allow you to take that Friday off (swapping with another coworker, for example, or maybe working extra hours Monday through Thursday of that week, or just convincing him to let you take the day off)
                2) meet up with the chorus tour after you’re done with work on Friday

                That’s how it works sometimes – if you explain to your boss why that day matters (“it’s like a cruise – either I’m there on time or I miss the boat”) and he holds firm, then that’s that.

                When I first moved to my current company, I already had a vacation planned and booked for that October (it was July). Turns out, my boss (we were a team of two) had also booked that same week off. After some back-and-forth, I ended up having to move my vacation back a week.

              3. Koko*

                In the scenario you describe, booking the travel when you have every reason to think it’s going to be OK is probably sufficient 98% of the time and it’s not like you’d get into trouble for it. It’s just that *you* bear the responsibility for the 2% of the time the boss says, “Actually, I really need you here that week.”

                In truth, I book most of my vacations before submitting my time off requests because, like you, I generally know whether I can be away any given week or not, so I would never submit a request to be away at a critical time. As a result, I’ve never had a vacation request denied, and the risk associated with me booking before submitting my request is practically non-existent. That said, it’s still a risk I bear.

                The basic point is that you don’t get to use, “But I already booked!” as leverage to push back against a vacation request refusal – that’s the part that’s inappropriate, not the actual booking before asking.

                1. LQ*

                  I think this is much more what I see happening around me (and what my boss said as well after asking because this conversation got me very concerned).

          2. LCL*

            Planning is fine. Planning to the point of making your reservations is not.
            In those workgroups where vacations have to be approved, the scheduler is willing to work like you. For non date specific requests, the conversation is supposed to go like this
            “Hey scheduler, I’m looking for some time in the middle of August. What works and what doesn’t?”
            If you handle your planned vacations like this, it still allows wiggle room for the deaths and unexpected birthdays and hospitalizations and other last minute stuff.
            What sucks is when employee says “You have to let me take off next week because I have already made the reservations.” Why do they do that? Just because you can do something, doesn’t mean you should.
            I have gone to the wall on this and made someone use sick time because they SHOVED A VACATION REQUEST SLIP UNDER MY OFFICE DOOR ON MY DAY OFF stating that they would be off that week, and it was a holiday vacation time so other vacations had already been approved and people were gone.

            Scheduling is hard. People have complicated schedules. Once you become an adult, it is not realistic to expect to schedule a vacation with anyone other than immediate family-spouse and kids. And retired relatives. Don’t even get me started on the people that want contorted schedules to see a relative that is RETIRED? What the duck?!

            1. LQ*

              I would absolutely say that the person shoving a vacation slip under the office door is unreasonable. Or even next week. But at this point I’m trying to plan something in February because I am going out of my way to not conflict with anyone else or any “important” things. Why can’t I just book that once I finally get a date that works?

              And it’s kind of sad that you think you can never have a vacation with someone who isn’t your immediate family, but if you aren’t allowed to ever plan without discussing with your boss I can see why.

              1. Sarah*

                LQ, you seem really concerned/confused about this, but I assure you that in practice it’s pretty easy. I’ve operated under a system for years where we request vacation in advance, and during that time I’ve planned a number of vacations, both domestic and international, with a variety of friends/family from across the country; it’s always worked. It may take a little bit of extra communication and organization, but not much.

                1. LQ*

                  I am. I did go and check with my boss. And it isn’t a thing we do here. Which I think is important. This isn’t everywhere that it is expected. (Which makes me think that OP#2 needs to at the very least have a conversation with the employee about expectations. If I was to move to a different place where it was required and my boss never objected to the way I requested time off I wouldn’t know.)

              2. Honeybee*

                First of all, I’m the kind of person who hates last minute travel anyway, so I don’t mind planning something several months in advance.

                But checking with your boss only takes a day at most. You just ask “Hey boss, does XX dates sound good for vacation time?” and they tell you yes or no. The way I’d do it is just chatting with friends ahead of time to get a range of dates they’re available, then check with the boss (asking about a second set of dates if the first set doesn’t work), and then confirm with friends and book the trip. Prices don’t fluctuate that much in the span of time it takes to confirm. And it’s way less expensive than paying a nonrefundable fare only to find out that you can’t go that week.

            2. Kyrielle*

              I have had some pretty limited schedules to see a relative that is retired! Of course, said relative is only in this country a certain portion of the year and my husband doesn’t have a passport (yet, I’m on his case about it), and oh yeah, our kids’ school schedules and the fact that part of the time she’s in this country she’s busy road tripping specific regions….

              She has a very busy life, in other words. :)

              And while a lot of the relatives I’m seeing this month are retired, many are not. By visiting our home towns when the others are there, and not busy with other things, we get to see more people. :)

          3. Koko*

            No, it just means the boss needs to not sit on vacation requests. My manager generally approves my requests same-day, often within the hour – about the same amount of time it would take to coordinate travel purchases with the other person anyway. Prices generally aren’t swinging around that volatilely within 24 hours, although granted my budget is not quite so strict that a +/- 10% price change would force me to forego the trip entirely.

        3. Ad Astra*

          I think some offices will see booking travel before getting time off approved to be a huge problem, while in other offices it would be fine. If you’re in the type of office where no time off is officially approved until right before (I had a manager who would sit on these requests for ages), you sort of have to book your flight and hope it works out.

          1. Doreen*

            I don’t think any job has a problem with people making reservations before they have the time off approved. I think the problem is with why they know people did so- because the only reasons I can see is to pressure the boss into approving it or because the employee is like a friend of mine, who had to cancel plans a few times claiming his boss cancelled his vacation because his boss (the owner) was taking that time off. After a few times, someone asked him how far in advance he asked for the time off. Turned out he didn’t – since he always took the third week of March or the fourth Friday in June, he expected the owner to remember those dates and plan his own vacation around them. And because he saw it as his vacation being cancelled, he expected the owner to reimburse him for any expenses incurred because of it ( for example ,an Amtrak ticket for Friday after work because his ride was leaving Friday morning)

      2. random person*

        It really, really depends on where you work and what you do. For instance, at my job we have 4 year-round non-managerial employees and an additional 12 seasonal term employees. You’d think that would mean that if someone wanted a week off during the summer, it would be fine because we bring in so many people just to cover stuff like that – and generally it is.

        But what about when three people want the same Saturday off, because summer is the time when people have family events to go to, we have 5 people working Saturdays, and we need a bare minimum of 3 people to run the business (and if it’s down to 3, 2 of the 3 have to be illegally denied a lunch break)? At that point, if you’re person #3 requesting leave, whether it’s for that one day or the entire week, you’re going to need to persuade someone to come in on their day off for you, or you’re not going to get that day off. There are limits. (I say this as a Saturday worker who’d love more days off, too!)

        1. random person*

          Sorry. We have an additional 8 seasonal employees, bringing the total up to 12.

        1. Wakeen's Teapots Ltd.*

          Depends a lot on your kind of business and seasonality. We can handle vacation any time of year save a few critical peak weeks that are blacked out.

          We’re a customer sales org. We can’t handle anybody taking vacation any time they want for any length they want, because departments have to be at least minimally staffed or customer’s needs aren’t met. We can approve pretty much anything in advance with “advance” being the operative word. Have to have coverage.

          1. RVA Cat*

            This. If you have blackout days, they need to be officially announced, several months in advance.

            1. Wakeen's Teapots Ltd.*

              Indeed. It’s akin to if you work for UPS, don’t plan on two weeks of vacation directly before Christmas.

              BTW, we don’t have a crap ton of vacation problems, and virtually everybody takes all of their days. Our vacation days aren’t exorbitantly generous, but everybody gets the last drop and usually when they want.

              I think one of the reasons it works so well is people’s willingness to cover for each other, just good attitudes. If there was somebody being rude about last minute demands-no-matter-what, the co workers would Not Be Pleased.

              1. Chinook*

                “BTW, we don’t have a crap ton of vacation problems, and virtually everybody takes all of their days. ”

                Ditto. I work for a place that gets generous with vacation days after an employee is there 10 years and people are encouraged to use it. Our directors are known for going off the grid for vacation for 2 or 3 weeks at a time (only to be contacted if the incident may end up in the media though I suspect many of them check their emails without responding). As long as you have a plan for coverage in place, no one cares as long as you submit the paperwork.

                On a side note – I had one field manager who kept forgetting to do this. When he finally handed me a quickly written one, I joked about whether or not this was all the time his wife wanted him to take off. He laughed and then thought it was a good idea and gave me her email address so she could see if he missed anything (I copied him on it). Turns out he did. Plus, she appreciated knowing that we knew when he was supposed to be off (he had been known to work on vacation) and my offer to cut off his corporate access if he started emailing us during that time.

                That being said,

        2. LBK*

          I don’t know if I really buy that – for short absenses, maybe, but there are positions and departments where it doesn’t make sense to essentially hire someone to just be a vacation backup when the job can otherwise be done in its entirety without them.

      4. T3k*

        A lot of very small businesses are like this, I’m afraid (I work for one of them). I don’t get any vacation days, but if I needed a week off, oh dear god, they wouldn’t know what to do because I’m the only one that does the design work.

        1. Betty (the other Betty)*

          Assuming you mean web or graphic design, there are temp agencies that send out designers. And freelancers who would be willing to take over projects as needed. Maybe you won’t ever plan to take a week off, but what happens if you are in an accident or sick for an extended period?

          It might be a good idea to make a list of the temp agencies or qualified freelancers in your area in case you need back up, and to make sure that your files are accessible so someone else can work with them in an emergency.

          1. Betty (the other Betty)*

            I realized that last comment sounded kind of rude. I just worry about people who feel that they can’t take time off because the company won’t know what to do. Sometimes people need to take time off and should have to feel stressed about it!

            2. T3k*

              Nah, I see your point (without it being rude). The files are available on the company’s computer (I work on site) but the main reason they don’t do freelancers is because they’re cheap. I’ve been tempted to quit and do contract work because I don’t get benefits anyways, and a local agency has contracts that offer over double what I currently make (I’m way underpaid). Of course, the downside is not knowing if I can land contracts back to back.

              And yeah, recently I was out unexpectedly for 2 days (transportation issues) and my boss was texting me, pretty much panicking because there was a rush design that needed to be done during that time that I hadn’t been informed of. Ended up having the files sent to me via email to work on at home.

          2. Koko*

            As well, your business should have a style guide that covers the standard colors, fonts, and other design elements typical to your brand. Between this and a library of logo and other branded PSD files, any freelance designer should be able to step in in a pinch.

            1. T3k*

              We do have some standard files to work with, and anyone who has had sufficient training with the programs should be able to do the job, but the main issue is the owner of the business is cheap. Although I may be able to convince them to hire someone for 20 hours a week to fill in for me (hmm… actually maybe I should ask if I can be switched to that instead, so then I can pick up another job).

            2. Liz*

              When working for a very small company (or even large ones, for that matter) there’s often a choice between doing the thing or documenting the thing. The only reason there’s thorough documentation for my last role is that during a certain project phase I had a few months with a lot of downtime that allowed me to get caught up. When I worked for a 10-person company none of us had time to document things! (And yes, we all know we should.)

      5. RMRIC0*

        It depends on the industry (and what you’re up to). I know some people in accounting where they have definite crunch periods followed by long lulls, and it’s not always feasible to staff up just for the crunch) or keep enough people on hand to make the crunch less crunchy.

    3. JC*

      The conversation in this comment thread reminds me of my last job. It was an office job and a non-customer-facing role where they were mostly flexible with time off, except for around holidays. They always wanted to have “coverage,” meaning that someone from every 5-10 person department needed to be in on any given day. This meant that planning for travel around Thanksgiving and Christmas got tense, especially since our boss wouldn’t usually get around to discussing who would be in until it started getting too late to plan travel. Planning for Black Friday drove me particularly nuts. One year my 30th birthday fell on Black Friday, and I was so worried that I’d be forced to be the only person in the office that day since I was low on the seniority totem pole (what a way to spend a milestone birthday, right?).

      I understand that some jobs legitimately need coverage, but you didn’t need it at this job. It was a government agency where we were the client for contractors, and where we did not interact with the public. The people forced to work on Black Friday and Christmas Eve and New Years Eve never got anything done those days. The agency wouldn’t even bother turning all the lights, but god forbid there were not butts in seats.

      1. Doreen*

        That is no doubt a government -specific issue. In my state , all state offices must be open on any weekday that is not a legal holiday unless the Governor’s office declares otherwise. When they are closed , it’s due to some sort of emergency. It may be all the offices in a particular area or it may be a single affected office, but it will never be based on dealing with the public or not.

      2. Jill 2*

        This happened to me when I worked in marketing… for a bank. Only one person got to take off the day after Thanksgiving a year. In our department of four. It was the most asinine policy I’d ever heard of. NONE of us were customer-facing, and the work there was like molasses. But our manager felt we needed “coverage.” I am positive her boss didn’t care, but it’s not like we could go over her head.

        I still get so annoyed when I think about that policy.

    4. Chinook*

      ” A 4 day weekend shouldn’t impact your department so much that you can’t give someone a long birthday weekend and if it does, then you need to seriously re-examine how your department is structured and how it functions.”

      I respectfully disagree because it depends on when that 4 day weekend. We have quick turn arounds at year end and if I took a long weekend around Jan. 1st, then we could miss something at year end reconciliation. Ditto so many days before quarter end. Also, if the right combination of people were off on vacation, then my taking an extra long weekend would make our department essentially grind to a halt (which is why I didn’t go camping last weekend). It is not that we are under staffed but more the fact that sometimes there are tight deadlines and/or times when everyone wants time off but not everyone should go.

    5. MsChanandlerBong*

      Unfortunately, my husband’s employer is like this. He’s given 10 vacation days per year, but he’s almost never allowed to use them. They have a points system for calling in sick; you can use your sick time, but you get “naughty points” (as he and I call them) against you. So when he knows he has a doctor’s appointment two months from now, he’d love to be able to take a 1/2 day of vacation time, but they say no 98 percent of the time. Then he has to call in sick (they won’t let him take three hours of sick time or go home after half a day of work or anything), use up a day of PTO, and then have the naughty points assessed against him. They sure are going to be surprised when he gives his two weeks’ notice at the beginning of September…

  3. Kat*

    I work with a woman that is constantly asking for time off at the last possible minute. Yes, it’s a problem that directly affects other employees and their hours.

    The bullying you into the time off is not ok. I’d deny it, because that is utter bs. He’s not 8yrs old and the center of the universe on his birthday. He needs to grow up.

    1. Kara*

      Wow. Really? You’d deny vacation requests because asking for one’s birthday weekend off is childish and thinking oneself “the center of the universe”. Yet another person I’m glad I don’t work for. Cheesus.

      1. Ask a Manager* Post author

        I think Kat was referring to the OP’s statement that he “is attempting to bully his way into having the additional time off.”

        Y’all are getting cranky again. Please consider this a reminder (to everyone) to please be kind to each other and letter-writers when commenting here.

        1. Kat*

          Yes, I was referring to the bullying.
          At my job, the woman pulls the same bs every time the schedule comes out and the manager lets her. Then, we get forced to cover her shifts. I have had to stay late and miss things with my kids that I would’ve been able to go to if she hadnt demanded the time off.

          In the past, when I was a manager, I was generous with time off requests as much as possible. I’ve encountered time off bullies and sometimes I had to be the hard ass. It sucked, but when you have 1 person that doesnt consider how their demands affect everyone else, you have to step in and put a stop to it. It affects employee morale. Everyone needs time off, but some employees take advantage of it and think their needs should always come first. I dont want to work with people like that.

        2. Kara*

          Apologies. I was cranky last night and let it come through in my posting.

          I still think the OPs post comes across as very hostile towards the employee and I am doubting that “bullying” is going on. Maybe some manipulation through already booked travel? But also I think you have to consider that booking travel nowadays can be fraught with issues. Sometimes if you have an opportunity to extend a flight or add on a couple of days of hotel at a discount, you have to make the decision RIGHT THEN or lose the deal.

          1. Colette*

            Sometimes you have to prioritize having a job over getting a good deal. It’s nice when you can have both, but that’s not always the case.

          2. sunny-dee*

            And — I am not saying this is okay — but if the employee feels like the OP is being unreasonably stingy with their PTO, they could simply be saying YOLO and doing their plans regardless. I reread the email, and it does sound like the OP is complaining about using two days of PTO. If I had a boss who complained — told me I was being a bully and put out the effort to write letters to management sites — because I asked for two days off, I would very much just do my plans and let the chips fall where they fall.

            Honestly, I would also be job hunting.

          3. The Cosmic Avenger*

            I think the issue is that the OP’s exasperation is showing, and so they gave us as much opinion as fact. If we had a more objective assessment of their employee’s “entitlement”, I think we’d have a much better idea of where the problem actually lies. As it stands, the OP could be very controlling, or their employee could be very unprofessional, presumptuous, and self-centered.

            Sometimes if you have an opportunity to extend a flight or add on a couple of days of hotel at a discount, you have to make the decision RIGHT THEN or lose the deal.

            True, but if I did that, I’d go to my boss and say “Hey, I know I put down for August 2nd through the 10th, but the flights were about $200 cheaper if we come back on the 12th, so we had to book that before the fares went up again. I hope that’s not a problem.” It sounds like the OP’s employee didn’t communicate the change directly to the OP, much less the reasons, as they only found out when some form was submitted.

            1. Robles*

              It’s worth pointing out that, at least in the US, you can always cancel your airfare for a full refund within 24 hours. It’s not well advertised, but airlines are required to do it (I think by federal law). At the very least, I’ve done this multiple times through Travelocity and never had a problem. So you can always book and then ask permission, noting that if the boss has a problem they need to let you know within the day.

              1. Honeybee*

                Yes! And American Airlines actually lets you put your tickets on hold for free for 24 hours.

            2. Elizabeth West*

              That’s basically what I did on my last trip. I let my boss know I was going again, but because it was month end and so close to the last trip, and taking the better deal extended it for a few days, I volunteered to work remotely.

              I volunteered to do that the last time, too, but everybody told me “Go have fun!” So I did, and when I got back, they were like, “Wow, you were gone FOREVER.” Working remotely made it less painful for them and didn’t suck all my PTO away either. Both times, though, I let them know well in advance, because I’m the only person who regularly does what I do in my small department. My boss can back me up, but she was chuffed that she didn’t have to that last time. :)

            3. Erin*

              Agreed. Totally plausible that this is what came up – but the boss will not know unless you communicate this information.

          4. LCL*

            Well of course the OP is hostile to the employee! The employee went through the process, had vacation approved, the schedule is done, then employee is demanding more time off. The whole point of requesting in advance is so that the schedule can be managed, so the work will get done, and other people can also get time off.

            Just because a better deal is out there doesn’t mean you have to buy it. There’s a reason my driveway isn’t filled up with cars-I am kind of a motorhead, there are many vehicles I want and the good deals are out there. But getting that many cars would be unmanageable so I don’t buy them. Tweaking your vacation request after it has been approved, so you can get a better deal, is unmanageable because it is too destructive to the schedule and affects the whole rest of your workgroup.

          5. Stranger than fiction*

            In Kat’s defense, I do think that this whole trend of adults having a birthday week or long birthday weekend, or even a birthday month is ridiculous. Not sure how it got started, but c’mon people, you’re another year older, ok you want to celebrate that’s fine, but this whole concept of being the center of attention for multiple days or weeks beyond the actual day of your birthday, ludicrous. IMHO.

            1. Elizabeth West*

              I kind of agree, unless it’s a milestone birthday and you have something special planned –like if you wanted to do a bucket list thing on a certain birthday, for example. But that’s obviously something you would know WELL in advance!

              On my actual birthday, however, I like to be pampered. It’s the one day a year I can be completely all about me and no one says anything. XD

              1. Kyrielle*

                I absolutely always booked out vacation on my birthday, or if it was a weekend day on the Friday before the weekend, at my old job. That, however, was because the job had on-call after-hours shifts that lasted a week, and booking vacation on / Friday before my birthday well in advance guaranteed I wouldn’t spend my birthday being on call. Which among other things would’ve prevented most plans, since on-call there had a ten-minutes to connecting in remotely time frame.

              2. Koko*

                I agree with both of you. The birthday weeks/months fanfare is just too much for adults out of college. Birthdays are like assholes…everyone has one and nobody really cares about yours except for you.

                Of course, it’s still reasonable to care about your own and I do like to use the occasion to do something nice for myself/pamper myself. Although ultimately the exact day isn’t that big of a deal to me. Does it really matter if my spa day is on your actual birthday or if it’s some other convenient day +/- a few days? Nope. I’ll enjoy it just as much 3 days after my birthday…possibly more if it means I don’t have to burn a valuable vacation day. (Just my preference, but I’d rather be able to tack a “recovery day” on to the end of a trip where I don’t go back to work until 2 days after my flight home, than take an isolated single day off in the middle of the week.)

                1. Blue Shell*

                  Yes, this. I think you can take some time for yourself while still being flexible with your office’s needs. I do like to use my birthday as an excuse to take a long weekend, but I’ll take whatever day makes sense in the big picture, whether that means taking my actual birthday off or not.

            2. aebhel*

              I don’t see why. I mean, I don’t really do parties, but it might be nice to sleep in on my birthday. As long as the time off is requested and approved, I don’t see how it’s any of my manager’s business.

            3. Panda Bandit*

              Not everyone would spend the week around their birthday having parties constantly or trying to be the center of attention. I would love to catch up on sleep and be able to either knock out some personal projects or relax for a few days.

            4. Dr. Johnny Fever*

              I dunno about a trend, but I was raised a JW and never had a birthday acknowledgement, much less a party. I’m not attached to that anymore, so I have a birthday week or weekend depending on when my birthday falls, and I take off work. I figure it makes up for lost time. But I don’t make obsequious demands about it – at least, to anyone other than my spouse.

      2. "Computer Science"*

        I’d urge you to take a step back, please. Birthdays are predictable events, and it’s reasonable to expect people to anticipate how the day will affect their availability. The employee in #2 is consistently giving short-range requests for events he’s either expecting or is actively planning. It’s a selfish way to behave.

        FWIW, I’m grateful you’re not my employee, either.

        1. Kara*

          The employee in #2 is consistently giving short-range requests for events he’s either expecting or is actively planning.

          Where on earth are you getting that? There is nothing in OP2’s post to reflect anything of that nature.

          1. sunny-dee*

            This. This entire complaint is about the guy asking for a single four-day weekend.

            And just to point out, it could be that the guy isn’t even the one who booked the plans. Maybe he’s turning 40 and his wife booked him a skydiving thing in Mexico (or something) as a surprise. Maybe he’s only going to be gone three days, but the return flight comes in at a time where he can’t reasonably get to work on Monday. We don’t know.

            1. LCL*

              I think the entire complaint is about the employee asking for more time off, AFTER he had vacation approved. Sometimes this can be accommodated, sometimes it can’t. It is really painful if someone tries this around a holiday weekend, or other times when you are short.

              1. sunny-dee*

                Yeah but — and this could be because of how the letter is written — but it sounds like the guy put in a request and extended it to a four-day weekend. That’s … really not an extension at all. It’s either one extra day of PTO (if they normally get weekends off) or it’s a couple of days extra (if they normally work weekends). But we’re not talking like an entire month off or something. The only thing the OP mentions is that four-day weekend.

                And, just to point out, the OP also wants to use the extension as an excuse to cancel the original request. That’s tacky.

    2. Elkay*

      Birthdays are a “thing” to some people, they are to me. I don’t think I’ve ever come to work on my birthday.

      1. Apollo Warbucks*

        But your birthday tends to come round at the same time each year so booking it off well in advance seems like it should be easy to do.

        1. LCL*

          Yes, the requests that always make me secretly contemptuous, BUT I TRY MY HARDEST TO FILL ANYWAY, are those requests for days off for something that happens annually on a specific date. That are last minute requests. Asking for a week off for whatever using our process is cool, asking after the schedule comes out, so less than four weeks notice and usually less than 7 days notice, is pathetic. It’s usually “I gotta have Friday off, it’s my wife’s birthday” announced on a Tuesday or Wednesday. It’s even more annoying if it is for a grandkid’s birthday.

      2. Allison*

        Agreed, I always make a point of taking my birthday off, or at least trying to. But just my birthday, and I probably wouldn’t ask for additional days to celebrate unless I was traveling or something, and even in those cases I’d try to put in the request far in advance if needed. If for some reason I was denied because they really needed me that day or I waited too long to request, I’d be bummed but I wouldn’t *demand* I get the day off and throw some sort of tantrum. I’d just make a point to try harder next time, and maybe try to take time off a little later and give myself a “belated” birthday break to compensate.

        Part of being an adult is learning to plan what you want to do, since Mommy and Daddy aren’t there to schedule your stuff anymore. Another part of adulthood is learning to go with the flow when things don’t go as expected.

        1. Elkay*

          Agree, I was just trying to address the opinion (one that seems to be expressed lots of places) that he was acting like an 8 year old because he wanted his birthday off.

          I book my leave as far in advance as possible, I generally have 3 weeks a year that are my standard holiday weeks (husband’s birthday, my birthday, anniversary) because they spread quite nicely through the year, I wouldn’t be heartbroken if I couldn’t have them but I would be annoyed if someone decided that me wanting to take the weeks because they were birthdays was childish.

          1. Allison*

            I will admit that’s a little harsh. There’s nothing immature for wanting your birthday off. I think the point was that the employee was acting immature for demanding that day off and throwing a giant hissyfit when he wasn’t getting what he wanted, but the point was communicated poorly. I know I get annoyed when people pout and go “but it’s my biiiiirrrthdaaaaay” when they’re not getting what they want.

            1. Ashley the Nonprofit Exec*

              Is the employee “throwing a giant hissy fit”? It sounds to me like he may just need direct feedback around expectations for time-off requests. If the manager is just silently boiling without saying anything, that may be contributing to the problem.

              1. sunny-dee*

                Yeah, all the emotion in the situation is coming from the OP. The guy booked his travel, and the OP is the one characterizing the act of booking travel as “bullying” and “entitled.” There are no other actions described for the employee.

                2. Ashley the Nonprofit Exec*

                  Well, OP didn’t say that he was throwing a giant hissy fit. She said there was a sense of entitlement. Those are different – one is a perception that is worth examining. The other is a behavior problem that needs to be addressed.

                3. Ask a Manager* Post author

                  For what it’s worth, sometimes OPs simply don’t give details because the situation is so obvious to them that it doesn’t occur to them that they need to flesh it out for others, or they’re not great written communicators, or they just simply write in a hurry and don’t realize what context people will want. We shouldn’t assume it’s not happening just because they assert it without details. We can question, yes, but it’s worth remembering that letters don’t always come in perfectly fleshed out form.

                4. sunny-dee*

                  I am responding to the people who are saying the employee is “throwing a hissy fit.” There’s zero evidence of that, is all.

              2. Artemesia*

                I always take with a grain of salt statements like ‘he threw a giant hissy fit.’ I remember having one of my employees when I was a manager claim that ‘Artemesia was furious when you XYZ’ — when I have never demonstrated ‘fury’ on the job ever towards a subordinate. For her any pushback at all was ‘furious’ and a ‘hissyfit’ etc etc. I am guessing the guy just said ‘I need to take that time because we have already made birthday plans.’ Those who report bullying and hissfits may be drama queens who amp up the emotion on ordinary disagreement. (or not — we were not there)

                Many businesses automatically give your birthday off; I know my organization did for support staff although not for professionals.

            2. Koko*

              Exactly – the immaturity is not recognizing the difference between a “nice-to-have” and a “must-have.” Having your birthday off work is a “nice-to-have.” It’s not something so sacred that how dare your manager force you to WORK on your BIRTHDAY!!

              When federal holidays fall on a weekend we often “observe” them on the next weekday so nobody gets cheated out of a holiday. If your birthday falls on an inconvenient day, just “observe” it on a more convenient day. A day off is a day off. Digging your heels in that you can’t be expected to labor on your own personal holiday is not the hill to die on.

      3. anonymous daisy*

        I have even requested my birthday off five months in advance. It just boils down to working together versus working against your boss.

        Boss – you seem to have problems with the vacation system. You need to set a policy so both parties have an idea of what will fly and what will not in advance. If you don’t want last minute requests then say how much notice you need. If you need a certain number of employees at work at all times, then say it. If you want a black out period for requests, then set it up in a policy. To me, it sounds as if you might be in a bitch eating crackers mode with how this employee went about trying to get time off. Granted, it was awkward the way your employee did it, but it is a minor annoyance that can be worked through if you set up a system for future requests.

    3. Victoria, Please*

      At my first job on a farm, we were told in no uncertain terms that our birthdays were not state holidays. The best way to get scheduled for your birthday was to ask for it off! But, the owner was working with a bunch of teenagers who were difficult in all sorts of ways and I think that that was just the last straw.

      We all loved and feared her in equal measure! She was a great mentor.

    4. Ashley the Nonprofit Exec*

      Managers need to made decisions based on what their role and responsibilities are. It’s (ideally) the manager’s job to be sure that work gets done and goals are met, to allow employees to maintain work-life balance within the company’s practices/policies, and to allow some reasonable way for employees to use the benefits that are rightfully theirs. The manager’s role is not to decide whether the purpose of an employee’s time off is childish/dumb/worthwhile/understandable. If someone wants to use all their vacation time to marathon shows on Netflix the day they come out, or to attend the wedding of every friend they’ve ever had, that’s not really the manager’s place to judge. Either approve it or don’t, but don’t base your decision on what the employee plans to do with the time. When that’s happening, boundaries aren’t where they should be.

  4. Engineer Girl*

    #2 – I’m concerned about the statement

    he should be granted his vacation requests regardless of the impact it has on a very small department.

    The size of the department should not dictate vacation requests. There are bad times of year to take vacations (surge activities) there are also bad times because others are taking vacation at the same time (coverage). A smaller department may have less coverage if others are out. But someone should be able to take a block of vacation with sufficient notice. If they can’t then you are running the department incorrectly. Yup, you. Good management ensure that people are cross trained so that there is coverage if someone is out (for whatever reason).
    I know in my last assignment we all had 6-9 weeks of vacation on the books when we only accrued 4 weeks a year. That meant that not one worker could take their full amount of vacation. I even had a hard time taking a weekend for my cousins wedding. To me, that is mismanagement.
    It isn’t entitlement to use the vacation you’ve been promised as part of your compensation package any more that it is entitlement in expecting to be paid X dollars per week. If I get 3 weeks vacation a year then I should be able to take 3 weeks vacation in a block.

    1. Matt*

      Actually, to think that you should be able to take your entire allotment of vacation time at once is a bit out of touch. One week is standard. Many places of employment will allow two. Beyond that? Come on.

      I accrue six weeks of vacation time a year, and can carry a maximum of two weeks over into the next year. So I should be able to take two months off if I please, and be upset with management if it’s not approved?

      1. UH*

        Why the hell can’t you take more than 1 week off? 3-5 weeks at once is quite common where I work.

          1. De (Germany)*

            But if Matt gets six weeks, why shouldn’t taking three or four in one chunk be possible?

            1. Engineer Girl*

              Ironically the American worker used to get 2 week vacations as a block. That was in pre-Internet days when you were truly out of contact. Now we claim it’s impossible. The only reason it’s impossible now is because we don’t manage correctly.

              1. Rae*

                Not really. We’ve moved from a goods economy to a service one. If you weren’t there to make teapots someone else could manage. But as a nation we don’t make teapots anymore, we sell teapots, we clean teapots, we re-paint teapots, etc. For many companies, this also means that there is a client relationship built with one contact and disrupting that can be very aggravating for the client.

                1. SystemsLady*

                  This is why it would be difficult for me to take more than a week or two off at a time, at least.

                  Because a client wants specifically me, the only other coworker she has a relationship with is booked for the month, and it’s a busy time in the project, I’ve also been pushing off a week of personal time vacation for about a month now. You just have to do it in some situations, and from my perspective I can kind of see what kind of industry the OP might be coming from.

                  I definitely would not be able to insist on having my birthday off if my birthday fell on an important project date. Now to go to a funeral or deal with a personal emergency, or if a date slipped to a vacation you’ve had planned for a year, sure – you usually have a good enough relationship with your client that they will be understanding – but almost anything else would be in bad taste.

                  Of course, there are also occasionally slow times with smaller amounts of projects when you’re encouraged to give yourself a vacation.

                2. Natalie*

                  I’m not sure that’s made much of a difference. The average goods maker (farmer, miner, factory worker) got basically no vacation for most of history. The jobs of the middle classes that got vacation have always been more service and client oriented.

            2. MK*

              I think it should depend on the work; there are jobs it would a problem for someone to be gone a whole month because of the nature of it. But if that’s no the case and the only reason is management’s discretion mfort with people being gone too long, that’s BS.

            3. Koko*

              This probably varies a lot from place to place.

              Where I work, that would indeed be possible, assuming you had the PTO to cover your absence. And generally someone who earns that much PTO is pretty high up the food chain, where you have a considerable amount of autonomy/privileges as well as a considerable amount of responsibility. I have seen many senior people at my org take 3-4 week vacations over the years…almost exclusively in August, when absolutely nothing is happening around here. And they are very careful to do as much before they leave as they can and slide any movable deadlines, that they can so that work that would normally be due on their vacation will either get done before they leave, or won’t get done until they get back, even if it would have normally been done while they were out. The idea is to have as few items as possible that you expect coworkers to do in your absence.

              And this pretty much works. So the idea is that yes, you can take long vacations. But by the time you’re at the seniority level where you’re earning that much vacation time, you should probably also have enough responsibility to know how to make it work without causing too much disruption to your department and to make all the arrangements necessary to be sure your deliverables get in on time, rather than looking to your manager to approve/deny the request and arrange coverage for all your work while you’re away.

          2. Katie the Fed*

            I take two-week vacations, and woe be it upon anyone who tries to tell me otherwise. I left a previous position over a manager who tried to guilt me about a 2-week trip I wanted to take. When I took my current position I made it clear that I have a 2-week trip-of-a-lifetime coming up in the next year and going on it is really important to me.

            More than 2 would definitely be unusual.

          3. Excel Slayer*

            So you US people get (remembering the childcare question from Friday) only three months of maternity leave and only two weeks of holiday?

            I’m so sorry.

            1. MJH*

              Three months of UNPAID maternity leave (unless your individual company decides to pay you). USA! USA!

              1. Excel Slayer*

                Unpaid? I don’t understand how you people don’t grind yourself into the ground.

                I would suggest fiery revolution, but you probably can’t get the time off for it.

                6. Ask a Manager* Post author

                  Could we lay off the U.S. bashing that’s been rampant here in the last month or so? There are legitimate issues with employment practices here, as there are in every country, but it’s starting to take over comment threads and isn’t particularly helpful.

                  Thank you.

                7. Windchime*

                  We do grind ourselves into the ground. People are anxious and harried and cranky over it, but we’re all used to it and there isn’t any alternative.

                  I’m really fortunate that my workplace supports using vacation time. My coworker just got back from three weeks in France and Italy. A couple of issues came up while he was gone, but we just handled it. I really agree with those who say that management is the key–not necessarily the immediate manager, because that person may not have any influence on the size of the team for coverage reasons. It’s the higher-up Management that is making decisions to run the company so lean that there literally isn’t coverage, so people get cranky and stingy when employees want to take the vacation time that they are entitled to as part of their benefit package.

              2. Nashira*

                To quote Myq Kaplan: “We’re number one! On a scale of one to ten…” in a lot of ways.

                2. JB (not in Houston)*

                  @ Nashira: I love him!
                  @ OriginalEmma he’s a comedian, you can watch his special on Netflix (at least if you’re in the US you can, don’t know about elsewhere).

                3. AvonLady Barksdale*

                  I CANNOT believe someone just quoted him! So awesome. We went to college together. It’s kind of crazy to see him everywhere now, but I love it.

            2. UKAnon*

              I think this is the crucial difference. In most countries, it’s so standard to have to cover for months and months, possibly at short notice, regardless of the time of year or how busy you are (parental leave, sick leave etc) that two weeks is just admin. AFAIK standard practice in most companies seems to be that if there’s a time of year you can’t have off they blacklist it (usually b/c it’s the same time every year when things are hectic) or in some places they mandate you take a certain amount of your holiday over X dates when they know it’ll be really quiet.

            3. BananaPants*

              We get 12 weeks of maternity leave that may be partially or totally unpaid, but only if your company has more than 50 employees and you’ve worked there for long enough to qualify. Those of us who are lucky are FMLA-eligible AND have short term disability coverage for 6 or 8 weeks after the delivery. Those who are super-lucky have actual paid parental leave.

              There is no guaranteed or mandated vacation or sick time in the U.S. There are many workers who get neither and literally have no paid time off. If they’re sick, they come to work sick or go unpaid and hope they don’t get fired. If they have a sick child they cobble together care or again take unpaid time off and hopefully have a job to go back to.

              I’m fortunate to have actual paid sick time (very ample – 14 weeks per year or something like that) and 3 weeks of vacation each year – after 12 years with the same employer. I can buy an extra week of vacation for the cost of my salary for a week if I want. When I had my babies, I got 6 weeks at full pay on short term disability, another 2 weeks of my employer’s dependent care leave (drawn from my sick leave), and then another 2-4 weeks unpaid until we could no longer afford to be without my paycheck. And I’m lucky!

              1. jhhj*

                I really hope you meant 14 DAYS of vacation. Or maybe I just want to get a job where you are.

                2. BananaPants*

                  14 weeks of sick time, total. Anything more than 3 consecutive days may require a doctor’s note and once you hit 5 consecutive days you’re required to have a doctor’s note and initiate a short term disability claim (which pays out using sick time and then shifts to 60% of pay when sick time is exhausted). Not a bad deal, all in all. We start with 2 weeks of sick time and they add a week each year up to a max of (I think) 16 weeks. I get this much because I’ve been here for 12 years! It resets every calendar year.

                  Frankly, having this amount of sick time available to me for maternity leave (or in the event of a major illness or injury, for that matter) is a major consideration in staying at this job.

                3. jhhj*

                  So you can take off up to 14 weeks sick every year? If you took 14 weeks at the end of the year you could take 14 at the beginning of next year (for a well-timed illness or injury or baby, say)? That’s pretty awesome.

                4. BananaPants*

                  I could, but in reality they cap sick time usage for a major event at however long you’re given on the short term disability claim. For example, after having a baby I got 6 weeks of short term disability to recover from childbirth and I was allowed to use sick time to be paid at 100% rather than at 60% of my salary for those 6 weeks. However, once my disability period was over I was on unpaid leave for the remainder of my FMLA; I couldn’t use any more sick time until I returned to work.

                  I suppose someone could burn through 10+ weeks of sick time in 1-2 day increments (not requiring a doctor’s note) but eventually their manager and HR would have a conversation about not abusing the very generous sick time that we are provided. Because they do require a doctor’s note after 3 consecutive days or a short term disability assessment after 5, it limits serious abuse (i.e. Wakeen can’t go off to Cabo for a week while claiming he has pneumonia). In a year where I haven’t had a baby I typically use no more than 7-8 sick days in the entire year and that’s pretty typical of most coworkers.

                  I’m told that the company gives this much sick time because it reduces their short term disability claims and keeps premiums lower than they would otherwise be, because most employee short term disability can be covered partially or fully by their sick time rather than the insurance claim. Regardless, it’s a benefit that I appreciate.

            4. Sans*

              A lot of people start out with two weeks and get more as time goes on. I have 22 days of PTO a year. What gets me, though, is that although vacation is part of your compensation, it seems very few employers are willing to negotiate it the way they do your salary. If you take a new job, it’s viewed as perfectly reasonable to expect more money – or at least the same amount. However, many employers expect you to go back to the low vacation level all entry-level employees get.

              I don’t take those jobs.

              I do have less vacation than I did in the job I was at for 13 years – about a week less. But it was the best I could do.

              And yes, I think the US is ridiculous when it comes to PTO. So many of us are brainwashed into thinking we don’t even have a right to take our time off and that we will somehow be viewed as not dedicated employees. What a load of …

              1. Ad Astra*

                I have less vacation time now, five years out of college, than I did at my first full-time job. You better believe I’ll be negotiating the heck out of some vacation the next time I’m looking for a new job.

              2. Koko*

                Wow, I can’t believe that someone companies would expect a senior exec to drop back down to 2 weeks a year!

                Most places I’ve seen use a combination of job grade and tenure – so the lowest level employees start at 2 and accrue more over the years as a reward for their loyalty. Mid level employees start out with more and also accrue more over the years. Senior execs start with the max from day one.

                1. Sans*

                  No, they wouldn’t expect a senior exec to drop down to two weeks. But your average worker or low level manager? Yeah, they seem to think you should come in making say, $80,000 yet be ok with hardly any vacation.

            5. the gold digger*

              Any job I have ever had (in larger companies but also at a really poorly-run small nonprofit), new employees start at two weeks but get more vacation the longer they work.

              I have not started a new job in the past three years (I have had three jobs in that time) without ensuring that I keep my seniority in vacation. That is, I do not start at two weeks just because I am a new employee – I go in with 21 days (tried for 24). So it is not a universal thing that Americans have only two weeks. Nobody I know except brand-new out of college kids has only two weeks.

              1. Excel Slayer*

                That makes sense, and I can only admire your negotiating.
                (Although it still seems pretty poor compared to the 28 day UK minimum.)

              2. Sunshine Brite*

                At my first job after grad school, there was sick time accruing but no vacation until after your year anniversary and then it started at a week.

              3. Folklorist*

                At my first company out of undergrad, you got 5 days of vacation until you had been employed there for 5 years(!!!!). I didn’t stay there very long.

              4. T3k*

                I don’t even get that. First job out of college was part time, so didn’t really get any vacation time there, and second job is at such a small business, no vacation time either. Woo. Other grads must be lucky to get 2 weeks starting out.

              5. CrazyCatLady*

                I get about two weeks of PTO. When I was offered the position, it was 40 hours to start with and another 40 hours accrued throughout the year. That has to cover vacation and illness both. The numbers will go up a bit when I’ve been in this position longer, but because it covers both eventualities (I will eventually want time off and will eventually be too sick to go into the office), it never feels like that much.

            6. Ad Astra*

              A lot of people who are above entry level in white-collar positions get 3 or even 4 weeks of vacation a year.

              I haven’t had two weeks off since the summer after my freshman year of college, unless you count unemployment — which sure doesn’t feel like a vacation. Not that I’m bitter.

            7. Stranger than fiction*

              Barely , you get ten weeks short term disability pay which is about half your normal pay and unfortunately a week or two is often used before the baby is born so essentially you get two months with baby off , that’s standard, you can sometimes get a couple weeks extension if you had c-section or difficult birth. There is also FMLA you can sometimes take for additional time off but not everyone qualifies for that and it is unpaid

            8. Honeybee*

              Well, some people get two weeks of holiday. There are many jobs that don’t give any paid holiday, as there’s no requirement to in U.S. law. And there are some jobs that give more – I think two weeks is just the most common set up/

          4. JC*

            This can happen in the US depending on the workplace, too. I’ve always had professional jobs where the work is individual and project-based, meaning that the project you are working on will halt if you are out but it won’t halt the team. These jobs started out with 2-3 weeks of vacation a year, but with time spent on the job you could earn 5-6 weeks after a number of years of service; you could also carry over 4-6 weeks a year. It’s been rare in my workplaces, but not unheard of, for someone with a lot of seniority to take up to a month off at a time. When I was a federal employee, I had a colleague with tons of years of service who was earning 6 weeks of vacation a year who took the entire month of November off every year! So it’s definitely more rare in the US but not unheard of everywhere.

          6. UH*

            Somehow my reply got in the wrong spot but I am in the US and get 6 weeks, not counting holidays, sick leave or personal days.

        2. Sparkly Librarian*

          If only we were all so fortunate! In the last ten years I’ve seen one vacation that was as long as two weeks – that was a C-level exec who had prebooked international travel before coming onboard at our company. She checked her email throughout and did some work while she was traveling. No other time (at multiple companies) has anyone taken more than a week at a time outside of parental leave or major surgery (and the full weeks were for major occasions like wedding or honeymoon). It’s not to say that extended vacations don’t happen, of course, but I don’t think they’re at all common in the U.S.

          1. Ani*

            The full week-off vacations are only for things like weddings or honeymoons? Oh yikes. What you are describing doesn’t sound typical to me at all of U.S. office workers, who generally in my experience take the bulk of their vacation time in one-week installments.

          2. Cat*

            Full weeks only for weddings and honeymoons? That sounds like a dystopian nightmare and is not consistent with anywhere I’ve worked (thank God). Nor is two weeks at all uncommon in my job which is part of why I like it.

            1. Ad Astra*

              I took three days off (plus the weekend) for my out-of-state wedding, though I did get called into work for an “emergency” about an hour before I was supposed to leave town. I came directly from the spray tan salon.

            2. Windchime*

              I’m fortunate, too. People take vacation in two- and three-week chunks all the time at my workplace. Many people have family at home in countries on the other side of the world, so they often take 3-week vacations to visit. Another guy just got back from Europe, and last summer a woman went to Australia for at least three weeks.

          3. Sans*

            I’ve worked in several major corporations and week vacations are common. Two weeks don’t happen as often, but they do happen. Two people in my department took two week vacations this year – both for vacations to Europe. They planned it way ahead, and it was no problem.

            I probably take 2 one-week vacations a year and spread the rest of time out into long weekends, or a day off here or there.

            1. the gold digger*

              Same here. I have worked in F100 companies and have never heard of anyone having a problem taking more than one week at a shot. I am on a week and a half vacation right now. My boss took two weeks last year. I took three weeks at my first job out of college. I don’t have data about this, but it is not my experience or that of any of my friends that they cannot take more than one week at a time.

              1. Jubilance*

                Agreed. I’ve only worked for Fortune 100 companies and I’ve never seen anyone bat an eyelash about a vacation lasting longer than a week. I’ve seen people take 2-3 weeks for international travel or their wedding+honeymoon and I’ve never seen it be a problem.

                1. Sparkly Librarian*

                  Maybe the trends I was seeing were due to working for smaller companies (500ish employees across several branches) instead of F100. We accrued vacation (I was up to 4 weeks per year when I left the last job), and often took 2-3 days here and there, but never in large chunks, so it rarely got used up (I had nearly 8 weeks banked that they paid out). Often a vacation spanning a weekend would be 7 calendar days or more. No one seemed willing to take a full workweek at a time, though, except for the major events.

        3. Apollo Warbucks*

          In the UK I can’t take more than two weeks (maybe two and and a half weeks) off in one go unless the head of my department approves, and that’s been fairly standard where ever I’ve worked.

          The reason is the business still needs to run and as a team the holiday needs to be shared out, if I booked 4 weeks off in August it would limit other people’s ability to take a vacation at that time.

          1. UKAnon*

            ^^ Essentially this. It isn’t just about coverage for you while you’re out. While I agree in principle that you should be able to book longish vacations, and you should definitely use all vacation you are given, I think that a lot can depend upon the company and team. For example it’s not unknown in the UK to offer contracts to work term-time only, in which case you’re already losing one person for up to six weeks at a time; if somebody else also wanted to book four weeks at once, nobody else would get a summer holiday that year – whereas if you can stagger it so two people are out all of the time and everybody gets two weeks, that’s going to be much better for team morale.

            (Also, I just can’t imagine taking four weeks off – the drag on having to get back into routine and go back to work just wouldn’t be worth it!)

            1. Elizabeth West*

              Me either. I had major post-holiday letdown after a nearly three-week trip in autumn. Coming back was HARD. The second time, less so, because I worked remotely, but I still get into the bitch-eating-crackers mode coming back to the US and getting used to the food again, lack of public transport, etc. Grrr.

            2. Stranger than fiction*

              So true! Even taking a week off causes me so much anxiety the last couple days leading up to my return and the hundreds of unread emails and trying to figure out what’s been taken care of and what hasn’t…that being said here we get 3 weeks but typically people take one at a time and once in a while someone takes 2 but no matter what they require you have a couple days accrued above what you’re taking so you don’t deplete your bank to zero when you do take vacay

          2. Lucina*

            In my company it’s the same. Longer holidays are possible, but need to be approved and booked long in advance. It happened twice in 5 years, someone went to New Zealand for a family celebration, and somebody else to India.

        4. BananaPants*

          I work in for a fairly typical large multinational, and most of the time when U.S. based employees take more than around a week off, a green card holder or naturalized citizen is visiting their family in their country of origin. For example, my boss goes to China for 3 weeks once a year, a colleague will go to India for 4 weeks every other year, etc. If you’re spending close to a full day on a plane to get to where you’re going and are dealing with jet lag, then you might as well stay for a while! It’s rare but I have seen guys use vacation time to have paid leave after becoming a parent (most get 2 weeks paid – drawn from their sick time). I wouldn’t say 3-5 weeks is common, especially not at the higher end – most just don’t get that much vacation time. But vacations longer than a week at a stretch do sometimes happen and we roll with it.

          We get a holiday shutdown where no one in my location works between Christmas and New Year’s Day; we have paid holiday during that time. Some of our senior people who have 4-5 weeks of vacation per year (and can buy up to 1 additional week for the cost of their salary) will take much of December off prior to the shutdown. Again, a pretty normal occurrence.

          I save most of my vacation time to deal with sick kids. *sigh* The little creatures get so germ-ridden in the winter and if they’re both home sick it’s not realistic to be remotely productive while working from home, so I’ll call out and use a vacation day if I really have to. They’re lucky they’re so awesome. ;-) Also, we can’t afford to actually go anywhere on a real vacation.

          1. Sans*

            I think the last time I took 2 weeks off in a row was a trip to Hawaii 20 years ago. But I used to work with this guy who took August off every year. No, we’re not in Europe.

            He was a long time employee, and it was just known that Joe would be out in August. He went to visit his sister in Montana for the whole month. He didn’t take time off any other time. He’d been doing this for 20 years. He was a good guy who worked hard and did his job well. We made it work.

        5. Allison*

          It depends on the industry. In the tech industry, where employers are trying to compete for talent, 3+ weeks is standard. In a lot of other industries, where people compete for jobs and take what they can get, employers only give 2 weeks (tops) because they know they can get away with it.

        6. The IT Manager*

          One week off at a time is very common. A bit more than one week (ie Friday and the next full week) is common. Two weeks is not unheard of. Anything longer than that at once is very rare. (I personally earn a bit over 5 weeks of annual leave a year, but that is at the highest level of tenure.)

          I’ll personally try to take a bit more than a week, but I have also learned to not actually be away on vacation the whole time I am on leave because that just leaves you returning to work tired from travel. My limit is pretty much a week. (For trips within the continental US, I don’t particularly want to be away longer than that. I might feel differently if a trans-oceanic flight was involved.) I am at the point that on some of my projects that I don’t have anyone to delegate work to so it mostly just builds up when I am gone.

          OTOH I was actually annoyed with my parents when they visited me in Europe for a week. (I lived there two years and they visited once for less than seven days.) They were staying with me for some of it so adding more days would not have really costs too much extra. I guess my dad who was the big boss of his public utility felt like he couldn’t be gone more than that. It was the summer so my mom, a teacher who was loathe to miss school, was off of work. Now that my dad is retired and my mom is semi-retired they do take longer trips. I hadn’t given it much thought before but it may well have been my dad’s reluctance to be away from work that led to there shorter vacations in the past.

      2. Advances,none miraculous*

        Sure, why not? If you can’t manage any length of planned leave without the entire house of cards toppling, you’re in real trouble if anyone gets sick or quits unexpectedly, so your managers need to be thinking about that beyond just saying no as a blanket policy.

        How on earth does anyone manage to relax, recharge and make the most of our short time on this earth with a limit of five days out of the office?

        1. Katie the Fed*

          “Sure, why not? If you can’t manage any length of planned leave without the entire house of cards toppling, you’re in real trouble if anyone gets sick or quits unexpectedly, so your managers need to be thinking about that beyond just saying no as a blanket policy.”

          But many places don’t build in that kind of extra capacity. That’s not on the manager, it’s an overall staffing and budget issue.

          1. Marcia*

            If they don’t have the capacity, then they don’t really offer the vacation time that they say they do.

            2. Apollo Warbucks*

              It depends on how it is phrased, I get 25 days plus 8 public holidays a year. I can request whatever days I like but the employee handbook and probably my employment contract state that it’s at my managers discretion whether or not to approve the request. In fact I’m sure my boss could schedule my time off for me and whilst it wouldn’t be popular I couldn’t argue against, the law says I must have a minimum amount of holiday in the year but it doesn’t state I can take it as I please, not being about to rely on your staff being in the office is no way to run a business.

            3. doreen*

              Not necessarily. I get lots of time off every year – 25 vacation days, five personal days and at least two floating holidays. And as far as accumulating leave, I just have to be below 8 weeks on Jan 1 , so I can actually have 12 weeks or so when November comes around. If I take 12 weeks off between November and January , then the two people who can cover for me can’t take a block of vacation during that period- precisely because if two of us are on planned leave, the third one getting sick or having an emergency will topple the whole thing. Same thing if I take five weeks in the summer.

              I wouldn’t disagree that an employer should have the capacity to give everyone a one or two week block – but that’s different from saying that everyone should be able to get a one or two week block of their choice ( what happens when 6 of 8 people want the same block ?) or that everyone should be able to take their full year’s allotment in one chunk ( If I take July and one coworker takes office, number 3 gets no vacation in the summer)

          2. Mike C.*

            We can sent people to the moon, but we can’t figure out how to cover for the time it takes to send then there and back.

            Simply mind boggling.

          3. F.*

            I work for a small firm (@40 employees) in the USA as a Human Resources Department of one. NO ONE else here can do my job. I also have spent over six months of the past year doing my previous Office Manager/Administrative Assistant job due to inability to find and keep someone in that position. I have been working unpaid overtime (since the HR Manager position is exempt) every week. I took a full eight-hour day of Paid Time Off a couple of weeks ago (still had to monitor my phone) It was my first full day of PTO since last November. This is simply a fact of life in a small company. By the way, the company offers eight days of PTO your first year and thirteen the second all subsequent years. I have been here nearly eight years and will never earn more PTO than I do now. It is not allowed to be carried over, either.

            1. Mike C.*

              This is simply a fact of life in a small company.

              No, this isn’t simply a fact of life in a small company, it’s a fact of life in a company that doesn’t properly staff up or cross-train.

              I get that the biggest thing for companies to do is cut their staffing to the bone, but they shouldn’t complain when the margins for error are so thin that they cannot meet them every single time.

              What would your company do if you won the lotto and quit tomorrow? Or you had a nervous breakdown from not being able to take a day off?

              1. AJS*

                You are absolutely right. There seems to be some corporate version of Stockholm Syndrome going on here.

            2. Sans*

              I’m sorry you’re in a situation like that but please don’t just accept that ‘that’s the way it is’. That’s what lets companies take advantage of employees.

              Maybe there are no other opportunities where you live, but believe me, in most places, there are other companies who will treat you better and be set up in a way where you CAN take vacation time pretty much when you want, and without monitoring your phone. If I was in a company like yours, I’d be outta there as soon as I could manage. There’s just no quality of life. They are taking advantage of you terribly – not just the lousy vacation time that you can’t take or carry over, but also you doing two jobs, unpaid. Maybe there’s a good reason they can’t fill (and keep filled) that admin job.

              Best of luck – I hope you find a better situation soon.

            3. abby*

              I agree with Mike and Sans. It does not have to be that way. Our organization is about the same size as yours and located in the US. We have one HR/Payroll employee. I am her supervisor and if she is out, I cover. Surely your supervisor or someone else should cover for you.

      3. Artemesia*

        What is deeply out of touch with humanity is that idea that vacation is a great privilege and you really shouldn’t take it at all if you are a good worker and you should never take more than a week at a time. And add that to low wages and job insecurity which are the norm in the US. The US is out of step with the universe on this one.

        3. AJS*

          The U. S. is out of step with do universe on a lot of work-related issues, and a great many Americans are fed up with it.

      4. Decimus*

        I worked for a small firm that did allow you to use all your vacation time at once, but you had to schedule it well in advance because they also tried to keep at least one person working (it was a consultancy firm that often had 2-3 people working on-site at various clients).

        The one time I had a case where someone I was working with insisted they must, absolutely, have some particular days off they were denied because I’d booked those days well in advance (and had also made non-refundable reservations). It turned out the individual had actually gotten a new job without telling us and their new job wanted those days for mandatory training.

        Ironically if they’d just told us that outright there would have been less of a fuss. Most of the problem came from the fact they were leaving about six months into a one-year project.

      5. JenGray*

        At my employer we get 13 days a year beginning when we start with it slowly increasing until we until year 5 of employment and then increasing again until year 20. They do not allow you to take more vacation than what you have accrued so you need to make sure that you check your PTO balance before requesting vacation (& most people are exempt salaried positions). I needed 3 days off for my vacation (one day was a holiday and another was a normal day off to make a full week) but I had to wait to request my time until I had that accrued. I would not have been able to take the full week off if it wasn’t for the other days because I didn’t have enough time but that is just the way it goes. I am new to the company so didn’t have much time to accrue the needed time.

  5. love on a real train*

    #2: it is unclear if this person is asking for *extra* vacation days, or vacation days that he is entitled to.

    Regardless of that, his “attitude” should have nothing to do with his vacation days. If his absence will result in legitimate problems, then you and he and maybe others should meet and discuss the issues and try to develop workarounds, ie, delegate to someone while he’s gone, etc.

    I’m sorry, OP2, but it sounds like you don’t like this person, or you resent him, and it is interfering with the objective performance of your job.

    1. Apollo Warbucks*

      I read it as time he’s entitled to. Yes vacation time is a benefit but everywhere I’ve worked makes it very clear that booking it is at your managers discretion and depends on the business needs.

      So even in the UK where vacation is a statutory entitlement there are restrictions on booking it, I can imagine there being even less restrictions or regulation in the US.

      Demanding the time off and having an attitude isn’t helpful to the conversation and would make me think poorly of the employee, it’s not how reasonable people behave.

    2. BRR*

      I’m pretty sure he had booked some time off and had the time to add a Friday and a Monday for his birthday.

      If the OP is a little irritated that the employee didn’t ask before booking I get that and I imagine that’s why the employee is bullying the OP (imagine if somebody wrote it saying they booked a trip but their boss wouldn’t give them the time off). If the OP is irritated because it’s during a busy period, I’m a little less sympathetic.

    3. KT*

      Yeah it’s an extra day–while I disagree with the employee’s “bullying”–it’s a long weekend–I don’t see what the big deal is.

    4. lawsuited*

      OP2, please take to heart Alison’s advice to accommodate vacation requests if at all possible. I worked at firm for over a year and was not able to take any of my 4 weeks of vacation (which were, of course, part of my compensation package and I made concessions on salary in order to get 4 weeks) because each of my many, many vacations requests were denied for “coverage” reasons because it was a small department. It’s one of the main reasons I left, because I started to feel desperate and like I might never get another vacation in my life!

  6. UH*

    And for OP2 – I agree it sound like you simply do not like this person. There is nothing wrong with using a company provided benefit.

    1. Kat*

      It’s how he is going about using it. It is not ok, at any job, to tell them you are extending pre-approved time off without permission. You dont book flights without having the ok from work unless you are a world class douche and want to find a new job.

      It’s showing a complete lack of respect and utter disregard for your co-workers and job. It’s also a serious lack of maturity.

      2. UKAnon*

        As I said above, I would be interested to have more information. It sounds possible on one reading of the question that he booked a pre-planned holiday that coincided with the week before his birthday, somebody decided to extend it as his birthday present and now he needs to get the time off… Also this might be a red herring, but there’s too many questions still remaining for us to really make a judgment on the situation, OP or employee.

        1. Nina*

          More information would definitely help. I initially read the birthday as an entirely separate event; as in “He already extended his vacation (the first set that was approved) in June and now he wants to have a long weekend for his birthday in August” or something.

          He’s entitled to his vacation time, but if this (adding days off at the last minute) is a frequent occurrence or he’s doing this during a busy time of year for their office, I can see why the OP would be frustrated.

      3. Kara*

        You dont book flights without having the ok from work unless you are a world class douche and want to find a new job.

        Seriously? “A world class douche”? Don’t you think that’s a little excessive???

      4. LQ*

        Good grief. I had no idea I was a world class douche for knowing my own schedule and my coworkers schedules and being able to figure out that taking another day or two wouldn’t be a problem. Why is that complete lack of respect and utter disregard for your coworkers and job.

        And if it is why don’t you talk to your employee rather than just calling them a douche?

    2. BenAdminGeek*

      I think many of us are likely bringing our own experiences to how we react to this one. I swear I had OP #2’s employee myself a few years back- from telling me he was trying to time the birth of his child so he could miss our busiest period (hallmark of a good father!), to asking for extensions to already extended vacations two days before his vacation started, to “forgetting” every single dental appointment he ever had until the day of the appointment.

      I would like to hear from the OP about the time until the vacation starts that he requested the extension. That makes a big difference- if it’s 2 days before that’s a problem. If the vacation is in 6 months, you should be able to make it work.

  7. Margaret*

    #2 – I guess I wonder why the time off is inconvenient – the fact of it using a week at a time, or a truly busy peak time that he’s just disregarding? E.g., even the extra long weekend would be totally unreasonable if I asked for it the first week of April – I work in taxes! Is this something like working in retail and wanting Black Friday off, or that the department hasn’t figured out how to have adequate coverage for normal levels of activity?

    1. doreen*

      It might also be that others have already booked this time off – I’ve known people who knew that a particular block of time wouldn’t be approved (because too many others already had approval ) and who used airline tickets to try to bully their supervisor into approving the time off anyway.

  8. SandrineSmiles (France)*

    #1 :

    Do you really want to be associated with Debbie Downer for eternity ? Alison is right. Go ahead with the other plan, and if she doesn’t like it, then, well, you can’t control *her* , so… so be it, I suppose ? You can’t excuse everything just because she’s good at her job.

    #2 :

    So, I read :
    – he expects he should be granted…
    – … without approval
    – is trying to bully his way into…
    – demanding… “entitlement” …

    Well, I’m sorry, but to me the letter doesn’t read as someone simply wanting to take advantage of a benefits package. And it doesn’t read like the OP has something against this guy “per se” either.

    It just sounds like someone is being a big bully and just thinking the world revolves around him. I would approve the first set and nothing more. He knew about his birthday when he booked that first set too, and if he’d said “Oh I’m so sorry, I didn’t realize X Y Z and also need those two extra days” I’d have found a way to make it work. But bullying his way to approval ? Wait, what ?

    Hell NO. And if he doesn’t like it, he can find another job where he’ll try to bully his way into getting things. That’s what I get from the letter… I’d be really tempted to have a serious talk with him and tell him this isn’t acceptable. Negociation is one thing. Bullying another entirely.

    1. BRR*

      That language in the letter signals to me that either the employee is a pain or the manager doesn’t like them and we don’t have enough information to know.

      1. Ani*

        We don’t have enough information. It’s odd, for example, that not even the first block of time has been approved yet. Is this because the employee is asking for all time off without any notice? Or is the OP routinely sitting on time off requests, leaving employees little choice but to go ahead and book flights etc? With the prospect of the OP then not approving some or all of the reqest? It all sounds extremely unpleasant in any case.

        1. UKAnon*

          Hmm… Because OP says in the first para that the first block was approved I was imagining that this was just about the extension, but now you mention it it looks like the OP is thinking of taking back permission for the first, approved block too. OP, don’t do this! Punishing the employee by taking away approved vacation is only going to build up a really bad feeling, both from the employee and from others who see you act this way. Whether you should grant the second block is up for debate, and we need more info to truly know, but once you have approved vacation stick to it, except in absolute emergencies.*

          *Nothing less than ‘the rest of the department was hit by a bus and our one contract is pulling out tomorrow unless this work gets done so come in or you won’t have a job left’ counts as an emergency in these circs…

          1. Apollo Warbucks*

            There is nothing that indicates to me the OP will rescind the already approved time off, but yeah the OP really can’t do that it would be so wrong.

            1. UKAnon*

              I was reading: “His first set of dates were approved. He then submitted a second set, to extend his dates, and without approval went ahead and booked his travel….And do I simply deny him both set of dates including the birthday, given the impact it will have on the department and not being able to function efficiently without him as it is a peak period?”

              So:
              – Set 1 approved
              – Set 2 asked for
              – Bullying
              – Reject both sets?

              I may just be really misreading that, but that’s where I got the idea from.

              1. UKAnon*

                Edit: Unless the employee tried some sort of “It’s pointless me taking any of it without taking all of it” trick but even so… we need clarification!

              2. Apollo Warbucks*

                I took the OP to mean that they would reject the request to amend the first leave and the second bit of time off.

                but I agree with you that cancelling the first set of leave would be a bad thing to do.

    2. aebhel*

      I disagree strongly. If it’s really going to put them out to give him the time off, then by all means don’t, but refusing to grant vacation time to ‘teach someone a lesson’ because they’re being annoying is really poor management, and it’s going to make the manager look petty and obnoxious to everyone else.

  9. Katie the Fed*

    #2 – You seem to be locked in an overly personalized power struggle over a fairy routine matter. I’m going to guess that this employee bugs you in other ways too.

    So, I’m going to share with you some tips on dealing with leave and leave requests that might help. Setting some ground rules might help a lot.

    – First, leave IS an entitlement if it’s part of the compensation, so don’t resent employees for wanting to take it. Even if you haven’t taken a vacation or sick day in 22 years, that’s you, and they’re different. They’re allowed to want to take leave

    – The reason for their leave doesn’t matter. I treat all requests the same, whether you’re going on your lifelong dream of living among Masai warriors or spending a day cuddling your cat – I don’t care. I don’t even ask but if they want to tell me that’s fine. The only exception is a family emergency – I’ll move heaven and earth to try to make that happen for you

    – If they make travel plans without getting leave approved, that’s on them, not me. They know the policy, and I’m not going to prioritize their leave because they didn’t check with me before booking a flight. That’s also a really good way to piss me off, so I sympathize with you here.

    – Have a clear policy when leave should be requested. 2 weeks out is a good rule of thumb, maybe 3-4 for holidays. If something comes up in a shorter time, you can do your best but no guarantees.

    – In general, try not to deny leave requests, and if you have to, there should be a strong, mission-related reason for it. Denying it when there’s not a clear reason seems arbitrary and unfair, so I would avoid doing that.

    Hope this helps.

    2. Elkay*

      Have a clear policy when leave should be requested. 2 weeks out is a good rule of thumb, maybe 3-4 for holidays. If something comes up in a shorter time, you can do your best but no guarantees.

      My old company had a policy that you had to ask at least double the time in advance to the amount of leave you wanted to take, so 4 days leave had to be requested a minimum of 8 days beforehand.

      1. Excel Slayer*

        My company has this exact policy. It doesn’t mean that some people don’t ignore it, but it does help.

    3. BRR*

      So many of your posts make me want to work for you (note to other managers, if you do things like this you have happy productive employees and can get/retain talent).

    4. LBK*

      – If they make travel plans without getting leave approved, that’s on them, not me. They know the policy, and I’m not going to prioritize their leave because they didn’t check with me before booking a flight. That’s also a really good way to piss me off, so I sympathize with you here.

      I find this an odd contradiction to some of your other tips. While I agree it’s not really a smart move to assume time off will be approved, unless they’re bugging you to go out of your way to accommodate it when you’re not easily able to do so, how does this not fall under “it doesn’t matter why you want the time off”?

      1. JuniperGreen*

        I don’t see that as contradictory. The issue with booking unapproved time off is not the “why” but rather the “when.”

        1. LBK*

          I don’t see what difference it makes, though. As long as that time isn’t a conflict, I don’t see why it matters if they pre-booked something or not.

          1. Katie the Fed*

            It just irks me. It doesn’t influence the decision, but it’s irksome. If I have 3 people that want Christmas week off, you don’t get special consideration because you already booked a flight. If you lose your flight reservation, that’s on you, not me.

            1. Graciosa*

              Like you noted below, I wouldn’t refuse to approve it just because the tickets were booked, but it can be irritating.

              I think the irritation comes from it clearly being presented as a club – as if pre-booking the tickets somehow will magically convince me to approve your vacation when I wouldn’t otherwise, or tell a co-worker that their vacation is retroactively revoked to accommodate the person who booked without bothering to ask.

              Neither of these are going to happen, but I still don’t appreciate the threat – or the assumption that 1) our relationship is adversarial and 2) you can make a choice to spend money in the hope of using my basic decency to force me to bend to your will.

              It actually doesn’t bother me when it’s just sharing information (bursting with joy about the great deal that will finally let employee fulfill the lifelong dream of living among Masai warriors – loved that!).

          2. Katie the Fed*

            To be clear here, all I said was “I’m not going to prioritize it.” I didn’t say I wouldn’t APPROVE it. A lot of people seem to be mis-reading that.

            1. LBK*

              Ah, okay. That makes more sense – it was the level of accompanying ire that made me confused.

      2. Katie the Fed*

        Because I’m not going to put myself in the position of deciding if their leave is for a good enough reason. Like I wouldn’t assume non-parents can work weekends, etc. If they want to take leave, they want to take leave. That’s all I need to know.

        It’s more that it doesn’t matter if you booked travel plans or not. I’ll make the decision without taking that into consideration. Yes, it will irk me a bit that you did it, but it won’t factor into whether or not I approve it. I’ll approve it if I can and if the mission allows it. As for why it pisses me off – it’s presumptuous. :)

        1. LBK*

          Oh, I totally get why it pisses you off, especially if the person is whining and pushing you to move things around for them when they didn’t bother to check first :)

          I think it’s perfectly reasonable in the context of generally trying to approve all requests anyway, in which case it truly doesn’t matter if they booked before or not – the request would have been equally approved/disapproved either way.

      3. The IT Manager*

        I think the problem is when the employee lets the boss know, “I booked my tickets already, can you please approve my leave?” It’s an attempt to pressure/bully the boss into approval because kind people don’t want the employee to lose money on their booked tickets or to get the boss to approve their leave instead of another coworker’s because the money has been sunk.

        The employee could do the same thing, but ask for leave without mentioning the already booked tickets and there’s no issue. Mentioning that the tickets have been purchased is a form of pressure on the boss.

    5. LQ*

      I’m really surprised that so many people expect that staff check with them before booking vacation?

      What does this actually look like to you?

      (I’ve never asked unless I wasn’t sure something was happening, “I’m looking at booking something in August, are we going to be doing X big thing during that month?” “No, that’s delayed until September.” *goes off to book August*)

      Is it someone checking in several times because they have to go back and forth with potential travel partners? Is it someone giving you a block of time? Do people not know their schedules and the business well enough to know when is good or not to take vacation?

      1. LQ*

        What about going to someone else’s wedding? I want to go to a friends wedding and I need to travel a day or two for it, I can’t go because I haven’t asked first? I’m really confused about this? Especially since there seems to be an element of if you assume it’s ok then I’m going to deny it.

        1. Katie the Fed*

          “Especially since there seems to be an element of if you assume it’s ok then I’m going to deny it.”

          That’s not even CLOSE to what I said! I said absolutely nothing of the sort and have absolutely no clue why you would think that. I’ve denied maybe 1 leave request ever because I had too many other people out.

          As far as the wedding, I don’t understand the question. If you need the day off, ask for the day off.

          1. SystemsLady*

            Normally a wedding is something you’d know about so far in advance that asking your employer before booking the travel does not really affect travel prices that mucb, so that confused me as well.

            1. LQ*

              But that is the day of the wedding. That’s the thing, it’s not like I can move the wedding back a week. Say I book the ticket a year in advance, I still can’t change the day of the wedding.

              1. Elsajeni*

                Right, you can’t change the plans in terms of rescheduling the wedding — but, as much as you don’t want to, you could change your plans and not go. Your friend’s wedding date doesn’t depend on your work schedule, but whether you can attend the wedding might; you should (in most workplaces) be clearing the time off with your boss before you commit to being there, including booking flights.

              2. Kyrielle*

                No, but you know about it far enough in advance to ask for the time in advance, in which case there’s usually no problem. If you wait until the last minute and ask for it then, and you can’t go because the other two people in the department asked in advance because one of them has a Miniature Lego Teapot Fanciers convention to go to and the other one just wanted to spend a long weekend cleaning their house, should the manager be changing one of their plans because you didn’t ask in advance?

                The trick to asking as soon as you know for a fixed-date item is, it gets you in ahead of the people who have flexible dates (like the house-cleaner mentioned above, who could do it another weekend but may have booked services once they confirmed that weekend).

                It does depend on whether your department needs coverage and how big it is. I don’t think there’d be much issue where I work with “oh, too many people already have that off” since we don’t have a specific coverage need. (But if I try to book a week off around a major release, that might be seen as a little blind to things…maybe. I’m not sure yet. Also not worried about it, since I don’t actually want that time off this year. I’ll figure it out when it matters.)

              3. LizB*

                Here’s the timeline:

                – Your friend announces their wedding date
                – You say, “Hey boss, can I get June 8-11 off next year?”
                – Boss says, “Sure, I’ll put it on the calendar.”
                – You go book your plane tickets

                This can all happen in the space of a day, maybe a week if your boss is busy. Ticket prices won’t change THAT much during that time.

            2. jhhj*

              It can also be an issue for a Jewish wedding, which can’t be Friday or Saturday (Saturday in the winter can work, if you are into winter weddings), so you almost certainly need to get time off for a Thursday or Sunday night wedding.

              1. Ad Astra*

                Is this the case with all Jewish weddings? I’ve been to what I would describe as a “half-Jewish” wedding on a Saturday, but it wasn’t in any kind of house of worship. Is it about the facility itself (the way you can’t have a Catholic wedding on Sunday because the church is already booked), or is it about the actual religious rules for this stuff? Just curious.

                1. jhhj*

                  Forbidden until after sundown on Saturday. Some rabbis will do it anyways, if they’re from a more liberal congregation — though I don’t think they’ll do it in a synagogue (which would be in use for services), you’d have to have it done at your reception (which is normal).

                2. Kara*

                  Religious rules. You cannot get married (or actually perform any work) on Shabbat (the Sabbath day). In the Jewish faith, Shabbat runs from sundown on Friday to sundown on Saturday. So Saturday weddings aren’t allowed unless you can schedule them for after sunset. A Friday morning wedding would work, but you’d have to have a dead stop for the reception well prior to sunset on Friday (to allow for time for cleanup and so forth).

                  How strictly the “no work” rule is followed varies a lot. In a conservative or Orthodox family/congregation that can mean no cooking, no driving, no flipping of light switches even. In a Reform family/congregation, it could be interpreted a lot more leniently, but a wedding is still a no-go.

      2. Katie the Fed*

        “Boss, I want to take vacation from 4-28 September. Is that going to be an issue?”

        “Nope. Go ahead and book it.”
        or
        “Well, we have a big project due then, can you adjust it by a week?”

        1. LQ*

          But shouldn’t I know if I have a big project due then? Truely big project I would always know I would have coming up wouldn’t I? I wouldn’t schedule something like that.

          And what if I change it from the 4-28 to 5-29? Do I have to check back in every time? Or if I only want a half day on the 4th do I have to come back? Like ok the flight leaves at 3:30, so I can be at work until 1 and still make it to the airport in time. Do I have to now say I want to leave at 1 instead of noon? (I would have to do that at my office in my request, but I would personally just assume my boss would be fine with it…Now with everyone saying stuff like you’re a douche if you don’t ask first and asking to be fired I’m wondering what on earth?)

          (And no I don’t think you would deny it! You are way more sensible, which is why I’m asking because you are totally sensible. But other people, including the op sort of seem to have that attitude!)

          And the problem with the wedding is I’m assuming I can take the day off because I can’t change my plans because I can’t ask my friend to reschedule the wedding. I’m not asking then telling the friend ok, book teh wedding venue!

          1. Katie the Fed*

            Ha, I have no idea on every variation of the scenario. In general, I manage to accomodate most leave.

            And while I know you might know what projects are coming up, you might not know that Fergus is also planning to take leave then, or that Mandy is going to be on maternity leave. Sometimes we know things you don’t.

            1. LQ*

              I have to say I’m now not wanting to take a vacation at all.

              I don’t even know.

              I don’t even talk to my boss enough to ask those things for each of the scenarios.

              Would you talk to someone if they were doing it wrong? That’s the thing, no one has ever told me, hey you should talk to me first. Or told me not to take a vacation I planned without checking with the boss on first. If you don’t tell someone what they are doing is wrong how do they know? Especially if you just keep approving the vacation. (The OP didn’t say anything like, I’ve talked to this staff person about the way the request vacation in the past. They just want to deny it.)

              1. Katie the Fed*

                I can’t help but feel like you’re over-complicating this. I don’t know the particulars of your situation, but it sounds like it might help if you clarified expectations with your boss.

                1. LQ*

                  I just went in and did that and he looked at me like I had lost my mind. He asked why I was asking him and that yes I should just book time. He then back pedaled and said something about if there are x people gone (more than have ever been on our team) and someone raises a union grievance we might have an issue, but that chances were good I’d still be high enough on the seniority likely to be ok, was that what I were worried about?

                  So yeah, not asking doesn’t mean someone is immature and a world class douche, it might just mean they have a very different culture than you.

          2. Colette*

            Sometimes the manager knows something is coming but you don’t. For example, when I talked with my manager about vacation last year, she said “actually, I think we might be in India then, can you make it a week earlier?”

          3. fposte*

            It’s going to depend on the job; however, sometimes when you think you know, your boss knows more. I’ve had a staffer get the week of a big project wrong and book his vacation for that week.

            In general, my staff is assumed to check the viability of dates before asking; I don’t think I’ve ever said no, because they’re more attuned to their dates. But they also shouldn’t be booking flights without checking with me first. In contrast, there’s nobody I would or even could check with; I’m in the great unsupervised realm of academic management, and it’s on me to be wise about when I take time off. I think that ranking difference isn’t uncommon, in that earlier in your career you’re likely to be creating more work that supports management and therefore management needs to know when they’re going to be going commando.

            1. Elizabeth West*

              Agreed. I would never book without checking, simply because airline change fees are so onerous that it’s easier and cheaper to just ask my boss, “Hey, I’d like to go to X for a week or so; is this date okay?” Like you and other said, often the boss knows about stuff we don’t. For events, like the Titanic concert in London, it HAD to be a certain time, but letting her know in advance meant we could work out the particulars of me working remotely. If I wanted to go to New Zealand (someday!!!), that’s a long enough trip and an expensive enough booking that I’d definitely want to check.

              Now my team shares their calendar, so I typically know if someone is going on PTO on X date–all I have to do is look. But that’s not necessarily the case at every company.

          4. Adam V*

            > And what if I change it from the 4-28 to 5-29? Do I have to check back in every time?

            Depends. Did the boss say “yeah, that’s a pretty quiet time of year, that should be fine”? Or did she say “well, the day you get back, we’re going straight to the [X] convention, so you’ll have to hit the ground running”? Or even “It looks like your request is bumping right up against Julie’s, so that’s fine”?

            In the first case, it’s probably fine to stop by afterwards and say “hey, I changed it to the 5th-29th instead”. In the second and third, it’s probably good to go back and say “is it still okay with the new dates? I wouldn’t want [us to be short-handed for the convention / you to be without both Julie and I]”.

          5. hbc*

            “I want to go to a friends wedding and I need to travel a day or two for it, I can’t go because I haven’t asked first?” No, you can’t go *until* you’ve asked first. Please let me know what wedding you have that has just a couple of day’s notice, such that you can’t let your boss know in advance.

            I think what you might be missing is that the places where you (almost) never have a problem booking it yourself, the approval “process” is dirt simple. As in, you say one sentence to the boss, the boss pencils it in on the group calendar and says “Okay” 99% of the time. While that might seem like wasted time, there’s the 1% chance that the boss says, “Ooh, Big Client is looking at coming sometime during that last week and I really need you to be here for it” or “Three other people are already off, so the backfill people you usually use are going to be overloaded.”

            Maybe you work at a place with a lot of independent operators where it doesn’t affect anyone else if you’re out for three weeks at a stretch, but that’s very rare.

            1. LQ*

              But why do I have to tell the boss, hey I want to book plane tickets on the May 15, 2016 before I book the ticket and then wait to hear back for who knows how long and then book the ticket and then request approval for the time off?

              I have worked in independent operator places where my boss would have less idea of my serious things than I would. And if I was out for 3 weeks I would be expected to cover all the work or make sure it was done and as long as I could do that it was fine.

              Where I work now it would impact others but people share their schedules so I would look and know before hand if someone else was out that week and wouldn’t even bother to try planning for that week. (And I’m not even talking about 3 weeks at a stretch, the OP is talking about a long weekend, not 3 weeks. Having to do all this planning before taking an extra day or two is part of what confuses me.)

              1. hbc*

                If you’re that independent, then it can be more of a “I’m going to be booking May 15th 2016 by next week, FYI. You have until Friday to object.” Or just understand that your position is very different. Surely you’d be ticked if you waited on hold for 2 hours and were told, “Eh, half our staff decided to take the week of the World Cup off.” Or you try to order a bunch of brochures and are told “We might have that printed for you in a month or so. The guy who does special orders is out for a month, one backup is out on maternity leave, and the other just quit.”

                1. LQ*

                  But what I’m saying is if I see 6 other people on the day off I’m not going to request it because that would be jerky…

              2. De (Germany)*

                My boss also doesn’t know that stuff because I work as a consultant. So I figure out what days I need off, ask the coworkers who would need to cover for me and then basically say to my boss “I’ll be out on these days, I have someone covering for me”. It’s really not complicated and can be done in advance.

        2. plain_jane*

          “Boss, I’m looking at going Far Away in Mar/Apr for about three weeks, but I’m not sure of the exact dates yet because ticket prices are in flux. Is this ok on your end? I’ll let you know as soon as I have dates firmed up.”
          Optional: “I shouldn’t need too much coverage – project X will be in field, and reporting for project Y will be done, just a couple of potential followups that otherperson can take care of.”

          I say this as someone who as a junior person booked my flight before getting approval for vacation. It had a strong negative impact on my relationship with my boss going forward that I had assumed a three week block wouldn’t be an issue because I had already accrued it.

          1. Katie the Fed*

            I screwed up royally when I started in government – I assumed the day after Thanksgiving was a federal holiday and didn’t request leave. I found out the week before that it wasn’t and I had leave booked. And I was poor GS-09 who couldn’t afford the $150 to change the flights. My boss brought that up for YEARS. Buddy, it was an honest mistake :(

        3. JB (not in Houston)*

          I don’t guy why some people thinking asking for approval is a huge ordeal. Maybe it depends on the circumstances. To me, you don’t necessarily know everything your manager knows, so you don’t always know if there’s something you’d need to be in the office for, or if other people already have been approved for that time and you need to cover for them, or there is some other factor you’re unaware of. Especially if you’re going to be gone for more than one or two days.

          Maybe I’m coming at this from a biased point of view, because I have to cover for my coworker when she’s out but she doesn’t have to cover for me, and she has a habit of just scheduling time off without asking me first if I’m going to be there. It’s irksome. And it doesn’t make me feel charitably toward her, that is for sure.

          1. SystemsLady*

            Yeah, and if circumstances change, a reasonable office isn’t going to ask you to change a vacation you had requested months ago.

            Clients will usually understand that a date slip on their end falls on them, and that they might not get the resources they had originally requested.

          2. Judy*

            I always wonder at my current job, because my manager’s answer to most anything is “That should be OK.” I never know if it is approved or not.

            “I’d like to use a vacation day to go on big field trip with my 4th grader in 3 weeks.” “That should be OK”

            “We’re looking at next summer’s vacation one of the two weeks between the kids getting out of school and husband’s start of summer school session.” “That should be OK” (Note, due to schedules beyond our control, there are only 5 weeks a year that the kids are out of school and my husband isn’t teaching, two in May, one in August and two in December.)

            1. Katie the Fed*

              I would ask. “When you say ‘that should be ok’ does that mean I can make travel plans and definitely be off that day?”

              1. JB (not in Houston)*

                Yes, I would clarify that, too. It could be that ‘should be ok’ is your boss’s way of approving it, or it could be that your boss doesn’t want to commit and is reserving the option to change her mind at the last minute if something pops up. That’s something I’d want to know in advance!

            2. Ad Astra*

              Every manager I’ve ever had has been a “That should be ok” person. I can’t get a “Yep, I’m definitely expecting you to be gone that day” until we’re within a week of the date. At least my current manager puts this stuff on his calendar.

        4. Kyrielle*

          “Boss, I’m hoping to take a 3+ week vacation starting sometime in September, ideally 4-28 September. Is this going to be an issue?”

          “No; I know your big project wraps up in late August, but this client *always* has some last-minute change requests and we need you available for post-cutover support. You can take a week in early September, or you can take 2 or 3 weeks with a start date of September 17 or later. If we’re still having issues from the project by a week before your vacation, we’ll have you cross-train Lucinda to handle them.”

          1. Kyrielle*

            Er. My answer would make more sense if I hadn’t reworded my question. No -> Yes. Or “That won’t work” maybe. In any case, the reasoning stands.

            It only works with a communicative boss, tho.

      3. esra*

        I’ve worked at a couple orgs where senior management doesn’t really communicate ahead of time when big items are coming up. So while, say, October in the past has always been an open schedule, they actually have a massive campaign planned and don’t let people know until September 15. It’s not good management, it frequently meant we couldn’t do the best job possible, but they just didn’t see themselves as accountable to staff that way.

        So I definitely check before booking any travel that will cost if I have to cancel or move dates.

      4. Graciosa*

        I once booked a couple over-two-weeks-each vacations with only a few weeks in the office in between.

        I had a candid conversation with my boss before I did this.

        “Boss, I have an unusual opportunity next year for Trip of a Lifetime 1 in Month and Trip of a Lifetime 2 in Following Month. I have tried to find other ways to schedule it, but these are the only options for Reason. I realize that this would be an imposition and will cause some stress on the team since I will only be in the office for a few weeks after Trip 1 before leaving again on Trip 2. Is this something that will be workable for the team, or should I choose one of the two trips?”

        I’m sure it helped that I was a long time employee, good at my job, and asking well in advance. I also made it clear that he was allowed to say it was too difficult to manage.

        I think that asking far in advance is probably more effective than pre-booking tickets to get the approval you want. Decent bosses *want* to give you the time off you’re requesting. Asking far enough in advance makes it easier for them to manage around your absence. Asking respectfully makes it clear that you know they want to help you.

        Not only was it approved, but my boss documented the heck out of his approval – which was really important as I got a new boss shortly before the first trip, and the new boss was not thrilled.

      5. HRrMe!*

        Our policy states clearly that vacations must be requested and approved in advance and that approval is dependent on ‘needs of the business’. We also acknowledge that different departments will have different notice requirements – the recreation folks are scheduled 2 weeks in advance, project management needs 3 weeks, executive services asks for 7 business days notice, legal wants 4 weeks, and so forth.

        I talk with Spousal Unit/other traveling partners, confirm the dates we’d prefer and run it by my boss. Generally takes 5 minutes or less to get his OK or preferred alternate dates, which then get fed back into the travel group. We all work – we all deal with the need to get time off approved, and we’ve managed at least 2 separate week-long vacations a year for the last 8.

        Getting preapproval isn’t really a deal-breaker. It’s very common in California, at least; 18 years HR experience in large/global to micro (under 10 employees) businesses up and down the state, every one required advance approval for vacation.

    6. Ad Astra*

      This is great. If there’s a mission-related, sensible business reason for not approving this employee’s leave, the OP didn’t provide it.

    7. Elizabeth West*

      I treat all requests the same, whether you’re going on your lifelong dream of living among Masai warriors or spending a day cuddling your cat – I don’t care.

      1. You rock as a boss.
      2. Both these sound equally awesome.

  10. BananaPants*

    Re: #1 – drop Glenda like a bad habit. In a time of turmoil, those executives offering you a ride may be the one to keep you employed or get you into a position with more stability. She sounds like a perpetual Debbie Downer and it’s clear that management doesn’t like her; be polite and pleasant but don’t hitch your star to her or give senior management the impression that you have.

    1. Rebecca*

      Agreed. I’d be really miffed if one of my coworkers took it upon themselves to tell management that I wouldn’t be taking them up on an offer, especially given the circumstances here.

    2. Trillian*

      Seconding the above. I would put a few bucks on the bet that if Glenda got the opportunity to ride along with the exec alone, she’d take it. Go to the exec ASAP, without talking to Glenda (so she can’t put her oar in) and let them know there’s been a miscommunication and you gratefully accept their offer.

    3. MK*

      What I find disturbing is Glenda’s attitude in this; there is a very definite feeling that she consideres the OP not just an understanding coworker, but an ally, somone who will side with her. I don’t think the OP needs to “drop” her, but adjusting expectation would probably be a good idea.

      1. Lizabeth*

        Probably Glenda will drop the OP since it would appear that the OP is no longer on her side.

      2. LBK*

        The problem with having “allies” in a situation like this is that if you’re an employee setting up an us vs. them dynamic against your management, you will lose 100% of the time because they have all the power. The only people you should be trying to turn into allies are your managers.

      3. INTP*

        I suspect this may be why she has so few supporters left. She probably pulled the same kind of thing with other people who supported her in the past – essentially lost all her friends in the org by expecting that they would support her unconditionally and to their own detriment.

    4. Artemesia*

      this one needs to be nipped so fast. The OP needs to let Debbie Downer know to not speak for her and needs to go tell executives that she would definitely like to ride with them. If they say ‘oh but Debbie said you had made other arrangements’ look baffled and say ‘no, I intended to take you up on your offer for a ride.’ Let Debbie make her own bed.

      You will be perceived as in cahoots with this negative person if you don’t specifically counter this.

      I once made the mistake of not affirmatively distancing myself from somehow who actually proceeded to send a nasty memo more or less in my name about a policy that while I didn’t agree, I knew was pointless to argue further against. It made me look like one of the disgruntled people who had failed to take ‘no’ for an answer. And it forever colored my relationship with that C level manager.

      Debbie is an anchor — fix it now or sink with her.

    5. INTP*

      I agree and this habit of trying to isolate her supporters from her detractors might be why she has so few supporters. I wouldn’t look at her as an innocent victim of an agenda who deserves support however it affects you. If she’s acting so that people feel like they have to choose between supporting her and their own careers, of course she doesn’t have many friends left! And that’s not the OPs fault or responsibility.

    6. Purr purr purr*

      I was going to say the same. Aligning yourself, whether it’s intended or not, with a person who management don’t particularly like is a recipe for future disaster. I would definitely be taking the execs up on their offer and also limiting my future exposure to Glenda.

  11. Rebecca*

    #2 – I think this sheds light on another phenomenon that’s becoming more common: a very lean working staff, to the point if someone is off for more than a few days, the others are negatively impacted. The OP needs to ask herself, what if Fergus shatters his femur while biking, or Jane breaks her shoulder while fording a canoe, and one of them is out of the office on medical leave for 8 weeks or longer? What then? How will you cover the workload without overloading the remaining staff? Can you hire a temp?

    As far as the OP’s employee, it appears he already booked travel plans prior to having the extended dates approved, so in my mind, he’s trying to force the issue that way. Not a great thing to do in my book. Plus, the OP is in a spot now – either approve it, and force the work on to others (and they all know why they’re being overworked now) or tell him to cancel his plans, deal with a surly employee, and perhaps start looking for a replacement.

    1. Ani*

      It’s possible the employee put in a formal request for the additional days off precisely to give the OP plenty of notice that OP will be short-staffed those two additional days. Because most surly employees would just call in sick at the last minute and take the time off that way. It’s so hard to tell from the contents of the letter, but it just seems this is unnecessarily adversarial and will only become moreso if OP starts yanking back days already approved.

      1. Koko*

        “Because most surly employees would just call in sick at the last minute and take the time off that way.”

        Well, yes, but you don’t really win any brownie points for not doing what surly employees do. The standard you’re held to is what responsible, cooperative employees do. And responsible, cooperative employees would neither pre-book their travel to force the boss to approve the days, nor call in sick at the last minute. They would get approval before making plans, or bear the risk of making plans without knowing for sure they would be let off.

      2. Kerry (Like the County in Ireland)*

        We have had 2 people out for 6 weeks each since January. One broke a kneecap while walking on campus and was out all of January and into February; one came down with a virus that threatened her hearing and was gone in late March through April. Truly freak things happen, and the remaining staff kept things going in each case, but it’s been at a big cost emotion/stress/burnout-wise.

  12. Dorf*

    #2

    A lot of people have keyed on the idea that the vacation taker is a “bully,” but where’s the “bullying”? Sounds like a standoff where neither party wants to blink, but pushing for self-interest isn’t the same thing as “bullying.”

    1. Worker Bee (Germany)*

      The “bullying” is there bc OP said so. In these comments we take the words from OP as the truth. S/he didn’t go into details, so we need to take her/his word for it.

      1. Dorf*

        Seriously? “Bully” is a pretty charged word for a disagreement about how a company policy is implemented. There are no examples of the bullying behavior, and just taking a position in opposition to your boss isn’t “bullying.”

      2. AvonLady Barksdale*

        As a general rule, I agree with you. However, in this case, I get the sense that the “bullying” is rooted in the request for time off. If the guy were berating the OP, coming by her office every day, leaving nasty messages, etc., I’d be surprised that the OP left that out. The main reason I get that sense is because the OP is focusing on the taking time off at a busy time, not on the “bullying”.

        1. JMegan*

          I agree. Normally we do try to give the OP the benefit of the doubt, but “bullying” is a pretty strong word to use without providing examples. I’d like to get more context from the OP – how much time was originally requested, how far in advance, how the employee is actually behaving – before coming to any conclusions about what’s going on there.

        2. Ad Astra*

          Yep, this is where I stand. It’s important to take letter writers at their word when it comes to facts, but that doesn’t mean we have to agree with the LW’s assessment of the situation. Words like “bully” and “attitude” indicate how the LW has assessed the situation, not the who/what/where of what’s actually happening.

        3. Koko*

          I think this may be a “living language” thing. To me, the context of “bullying someone into someone” means the somewhat older usage: “using high-pressure tactics to forcibly get one’s way.”

          With the cultural zeitgeist of attention on school bullying these days, though, I think a lot of people now interpret the word “bullying” as “pervasive, intensely personal harassment” like the kind you describe in your comment.

          My guess is the OP meant the word more in the older meaning than the newer one. That the employee is throwing weight around inappropriately to get his way (passive-aggressive guilt trips) rather than the employee is harassing and abusing his boss.

          1. JB (not in Houston)*

            Thanks for pointing this out! I took the OP’s use of the term as meaning use #1, but clearly others are taking it as use #2. That surprised me, but now that you’ve pointed out what should have been obvious to me, I see where the difference in reactions is coming from.

      4. Ask a Manager* Post author

        As I wrote above, sometimes OPs simply don’t give details because the situation is so obvious to them that it doesn’t occur to them that they need to flesh it out for others, or they’re not great written communicators, or they just simply write in a hurry and don’t realize what context people will want. We shouldn’t assume it’s not happening just because they assert it without details. We can question, yes, but the fact that they didn’t give sufficient evidence doesn’t mean it’s not happening.

    2. Katie the Fed*

      I noticed that too – it’s a really strong word. But in this case I didn’t focus on it because it’s telling enough that the OP perceives it as bullying – it’s a pretty toxic relationship for sure.

      1. Dorf*

        But employees can’t be responsible for the impressions of a manager. Bullying upward is possible but rare. The employee here has pushed, and the manager doesn’t like being put in a position to push back–that’s fair.

        There’s a chance her for the manager to win an ally down the road (or at least to establish a clear standard in the future) if the vacation can be granted.

        1. Katie the Fed*

          I think you’re reading something into my comment that wasn’t there. I’m not saying the manager is right or not. But the point is – it’s so toxic at this point that it doesn’t matter if we can show it’s bullying or not. They need to focus on fixing the situation.

        2. Apollo Warbucks*

          If the employee is behaving in a manner that the OP is finding offensive / objectionable then they have let themselves down, irrespective of whether or not bulling is the right word to use.

          The employee needs to understand that demanding time off at late notice is an imposition on the employer and they should wind their neck in and stop making a fuss, its one thing to make a request and another thing entirely to demand the time off.

          1. Ani*

            Except another way to look at this is: The employee was giving the OP advance notice that the plans had changed and he/she would be out an additional two days. Many employees who wanted to shaft the employer would call in sick at the last minute and take those days that way.

            1. Apollo Warbucks*

              But the employee is not entitled to use their vacation time whenever they please and just because it’s convenient for them to change their plans doesn’t mean that the employer is obligated to approve the a change to the request for time off.

              The grown up thing to do is talk about it reasonably and see if a compromise can be reached if not they the employee needs to suck it up and get on with doing the job they are paid for or be more organised.

          1. Kara*

            “Manipulative” maybe?

            I, too, keyed on “bullying” as being excessive, both because, as someone else pointed out above, it’s hard to bully UP, but also because the entire tone of OP’s letter seemed very hostile towards this employee. (Which is probably what coloured my earlier responses up-thread.)

  13. Moonpie*

    #2 – You mention this is a small team with peak seasons. I understand that. I am diligent about encouraging my team to use their leave. However, we are also a small group, and most of them work in a role that does not allow for remote work or “catch up when they get back”, or temps (due to the training required). So I have to have a minimum number present at all times. Fortunately, we’ve built a good team, and they work amongst themselves to plan their time off and notify me as much in advance as possible. I love to give people their birthdays off, but if plans collided and I’d already stretched to approve the maximum number I could spare for a particular day and someone additional asked for it at the last minute, I may well have to say no. At the same time, I’d look to see the next possible time I could offer off instead. Stuff comes up, but if I had an employee who was repeatedly ignoring our efforts to work together for coverage and for time off, it would be a discussion point between me and that employee for sure.

  14. schnapps*

    OP2 – I work in a small department. I’m also in government which means everyone has huge amounts of vacation and various other time banks. Any time off is “subject to operational needs”.

    So if a request for time off impacts operational needs, then it’s not usually granted except in extenuating circumstances (case in point: no one gets time off in July because that’s our big push. There’s a long stretch from August to middle of September where we can go down to minimum staffing. This year, one coworker was granted time off in July because her brother is getting married).

  15. NDQ*

    #2, I once worked with a supervisor who said, “I didn’t approve your sick leave request because your email wasn’t written in the form of a question. It has to begin with ‘May I…'”

    I would also never use her for a reference because if you actually used the sick or vacation leave benefits, she gives a less than stellar reference.

    NDQ

    3. Allison*

      Now that’s just ridiculous. She sounds like an elementary school teacher who won’t let you use the restroom until you say “*May* I go to the bathroom” instead of “can I go to the bathroom?” Or a middle school foreign language teacher who makes you say it in the language you’re learning.

      1. Andrea*

        That’s the first thing I thought of—it’s not a child asking to leave class to use the bathroom, it’s an adult who wants to use the time off they are entitled to!

      2. PegLeg*

        As a grown adult who now knows the difference between can/may, I look back and cringe at my elementary school self who would ask “Can I got to the bathroom,” then say “yes!” and leave the classroom when the teacher would respond “I don’t know, can you?”

        2. Desdemona*

          Really? I learned can/may pretty young, and cringed every time a teacher would pull that old trope out on my fellows. Totally rude, and such a lame pedagogical tool. I can’t remember anyone ever bothering to explain the difference, we were all just supposed to intuit it from their snide responses. To me, “yes!” and leaving the room is the response of a strong, assertive child refusing to play that passive-aggressive game.

    4. Ani*

      Some employers do want to discourage employees from actually taking the time off they are ostensibly given, and the way to do that is to yank back approval of days off.

      1. Miss Betty*

        Absolutely. I had a boss once who used to write up the employees who used all their vacation and sick time in a year (and it didn’t roll over). (She’d also write people up and never tell them about those write-ups, then surprise people with them at their annual reviews.)

      1. NDQ*

        Ha. It’s her interpretation of the rules: must be requested and approved in advance. She believes that a request can only follow the “may I” format.

        If this were her only quirk, it would be funny. I’m just happy my tenure under her was brief. I imagine her playing “Mother, May I” during her off hours.

        NDQ

    9. Koko*

      Dear gracious sir,

      May I have the privilege of vomiting in my home toilet today rather than the wastebasket next to my desk?

      With all deference,
      Your humble employee,
      Koko

  16. Jwal*

    OP1 – I feel tor about this one. If you think that management has a grudge against this person then associating yourself with them (or appearing to) is probably not going to be massively helpful for you.

    That said I know what it feels like to hate work and feel like you don’t have support there, so completely distancing yourself from Glenda feels bad as well.

    I agree with Alison that you should go with the execs, but I don’t think that I would phrase it quite like that. I’d probably out-and-out say that I think it’d look bad if we didn’t go with them, and then just try to be firm but apologetic.

    It feels a bit like trying to decide whether to sit with your mates or the popular kids at lunch!

    2. BananaPants*

      Glenda not being well-liked by management is her problem, not the OP’s. If the higher-ups really don’t like her (even if it’s for a B.S. reason) then that’s a very hard thing to change and OP being nice to her isn’t going to help any. OP needs to look out for her own self-interests here.

    3. JenGray*

      I agree. It’s really a hard spot to be in and you don’t know exactly how things will end up. It could be fine that you are friendly or friends with Glenda it could not be. I would explain to Glenda about why I am going with the execs but also let her know that I am sympathetic to her & how she has been treated. I would also let her know that is is nothing personal and you understand that it could blow up in my face. It sucks with having to deal with execs that just make decisions that don’t make sense but sometimes this is how employers choose to run their business and you just have to go with the flow.

  17. PontoonPirate*

    Re: #4: The head of HR where I work commented once in a work group that he will always look up a candidate’s current employer and make a reference check, regardless of whether or not the candidate has indicated this is okay. It blew me away. I actually spoke up (in front of everyone else … where is my filter sometimes?) and pointed out how awful that would be for a candidate who needs to protect their current employment situation. He clearly disagreed with me, but he’s not held it against me either, so there’s that.

    2. Apollo Warbucks*

      Well done for speaking up it’s up to the employee if the decide to let their current employer be contacted for a reference. It’s a jerk move by the HR guy to ignore that.

      1. PontoonPirate*

        I don’t understand his point of view on this one, but then I’m generally baffled by a lot of policy decisions my company makes. I don’t have the insider point-of-view, though; I’m not high enough on the ladder to be invited to those sorts of meetings. To be clear though, I don’t think there’s an insiders-view justification for this kind of action.

        Silver lining — he’s the head of HR; I don’t imagine he actually gets involved in a lot of the quotidian tasks of hiring, so he’s probably not making that many reference checks at all. It’s also not an official company policy to my knowledge, so hopefully we haven’t negatively impacted too many people.

        1. hbc*

          I understand his point of view, it’s just phenomenally selfish. It’s better for your company to get an understanding of the candidate from his or her current employer, it’s neutral to positive to the person you hire, and neutral to negative for every other candidate. He’s not worried about society, just him and his company.

          Or maybe he’s just naive. He would never punish someone for looking, so he doesn’t understand that someone else would take that call a different way.

  19. RVA Cat*

    Re: OP #1 – “Glenda is a very intelligent, talented person at her job, and I do feel she has been unfairly treated over the years. Management seems to have a personal grudge against her.”

    The best way for you to support Glenda is to support her moving on. Do you know people through your network who would need and appreciate what she brings to the table? Management is not going to change.

    1. Artemesia*

      If this is the way Glenda behaves then nowhere she is the victim of personal grudges. If she did me the way she had done you, I’d have a personal grudge. She is actively undermining you with the people who control your career.

      I would be very clear with Glenda that she is not to speak with me with the bosses. Don’t make this ‘tactful’ so that she doesn’t get it. Her speaking for you was a major transgression that damages you. The OP needs to clearly fix that fast.

  20. Long Time Reader First Time Poster*

    What’s all this business about *asking* for time off, anyway?

    I never even word it in the form of a question. My typical time off “request” to my manager goes something like “I’m planning on taking three days of vacation time next month, August 1-3. I’ve checked with the team and nobody else has scheduled time out during that period. Please let me know if you are aware of any other conflicts, otherwise I’ll process the paperwork with HR. Thanks!”

    I’ve always been under the impression that one should not have to *ask* for permission to use one’s benefits. One should obviously make sure that there are no conflicts, but it should not be a dynamic where you should be saying “please may I” and your manager decides whether or not you are worthy.

    If I put in a request for time off, I’m expecting it to be granted unless there are seriously extenuating circumstances. And I don’t think that’s entitled at all.

    1. LBK*

      I don’t think people ask as in asking for permission, but rather they just take the “please let me know if you are aware of any other conflicts” line of your phrasing and word it as a question (mostly because a lot of people aren’t comfortable essentially giving an order to their manager).

      Most people also have to get approval in a systematic sense – when I submit a request, my manager has to go in and approve it in our benefits system.

      1. SystemsLady*

        Yup, this is what I mean by “asking” as well.

        The idea that there are even managers out there twiddling their fingers and denying leave just because they can baffles me – even here I haven’t heard of them!

    2. LQ*

      This is much more how I’ve gone about it. My supervisor does “approve” it but he’s never turned anyone down. He did talk to people about requesting time off further in advance because some people were doing it like the day before. But he had a conversation rather than just denying those requests.

    3. Apollo Warbucks*

      It’s not about your manager deciding whether or not you are worthy, but more that the business can still run efficiently everywhere I’ve worked the overriding presumption is that time off request will be granted unless there is a very good reason not to.

      Your first paragraph describes very well the process that I’ve used to book time off everywhere I’ve ever worked.

    4. Allison*

      I don’t ask for permission, but if I’m looking to take time off or work from home on a certain day, I might say “I’d like to _____, is that okay?” or “I have this thing coming up and need to take these days off, is that okay?” It’s never been a problem, and I pretty much go into it assuming it won’t be an issue, but phrasing it that way at least shows that I respect her position of authority and I’m flexible enough to not take that time off or work from home if it’s not okay.

      Then again, I’m a contractor, I don’t need to go through a formal approval system for time off.

    5. JB (not in Houston)*

      As LBK said, I think when people talk about asking for time off, they mean doing exactly what you do. That’s what I mean. I don’t ask “please may I take this Friday off?” But I do say, is it ok if I take this Friday off, or I was planning to be out on Friday, let me know if there are any conflicts.

      I think it *can* be entitled to expect to take time off whenever you request it unless there are seriously extenuating circumstances, but it would depend very much on the nature of the job. Many (maybe even most) places it wouldn’t be a problem.

    6. Sunshine Brite*

      I’ve had to ask permission at every job but this one so it’s strange that I didn’t need to follow-up a million times verbally and written to know if my time off was approved or not even though I wasn’t able to get it in months in advance like at other places because I had 2 conflicting trips that I was considering. At my last position, I entered the request months and advance and she just held onto it waiting to see if anyone else wanted that time too. I just ended up making plans because she was taking forever in saying yes or no and it wasn’t around a major holiday or anything.

    7. Andrea*

      That’s how it works for me, too—I say that this is what I’m planning, and let me know if that’s a problem, though I typically wait to book until I have heard back. I’ve only had a problem one time at one job, years ago, and that was when I was a federal employee and I wanted to go to a family reunion out of state, and I’d asked very early (like maybe two months early). My manager hemmed and hawed and finally told me to see if I could choose different dates because another coworker, who was pregnant and due two weeks after my family reunion, “might go into labor early.” I said that no, I could not move the dates of my family reunion, which was going to be attended by about a hundred other people who had already made travel plans. Ultimately I was not allowed to go, and my pregnant coworker gave birth a week or so after her due date. I left very, very quickly after that.

  21. Ad Astra*

    I can’t help but wonder if OP #2 has an unreasonable vacation policy and doesn’t realize it. In many small offices, there is no good time for anyone to take time off. None of the employee’s requests seem out of line based on the information we have, so it’s hard to tell if the OP resents employees using their vacation time or if there’s truly a business need to deny vacation time during this particular period.

    Either way, I highly recommend looking for opportunities to cross-train employees so that one or two missing staff members doesn’t shut the whole department down.

  22. IndieGir*

    I’m going to stick up for OP #2 here, because a lot of people are making assumptions about her that I’m not getting from the post. I don’t get the sense that OP#2 is annoyed at the employee wanting to use his time off, she’s annoyed because OP#2 is being entitled and playing games to get the time off he wants. I had an employee who used to do this to me all. the. time. At the time, I was managing a 5-person call center. One person was already out on maternity, and my rule was vacation was first come, first serve and we had to have 2 people in to cover the phones. Not an unreasonable policy. One employee would constantly come in at tell me, not ask me, that she was taking a set of days off, regardless of whether the others had asked for it off first. My boss at the time would completely undermine me, and tell her it was OK. Since I’m not a glasshat, and since I didn’t want to rescind vacation for the other two, I wound up covering phones all alone for an entire week on at least three separate occasions. The only small victory I got at one time was making her take a week unpaid, as she had used up all her days for the year. My idiot boss wanted to let her “borrow” days from next year, but when he saw my head was about to explode, he backed down. And yes, at the time she had a nice number of days to choose from — 3 weeks vacation, 5 sick, 2 personal, and 3 family care days, plus 9 paid holidays, so it wasn’t like she was out b/c we were cheapskates.

    So, I can see OP#2’s perspective. It’s not the time off request that sticks in the craw, it’s the evil, blackmailing way of trying to ensure you get the time off.

    1. Ad Astra*

      It would definitely help if we knew more about the existing policy at OP #2’s office, and whether the employee’s actions comply with that.

  23. eplawyer*

    #1 – let me be blunt here. I do it so well. Is Glenda going to protect your job when firing comes around? Is Glenda going to pay your bills when you get fired along with her because she is perceived as the problem (and with her attitude probably is) and you are associated with her?

    The only going to protect your job is you. Glenda has already indicated she is blind to perceptions here by speaking up for you and declining the shared ride. You have to look out for you. Feel bad for Glenda that’s fine. Maybe even point how Glenda’s attitude might be affecting how management sees her. But do not hitch yourself to her.

    #2 — the guy already got his 1st request approved. Then without asking booked extra travel. Whether it is attached to the already approved vacation time or not, he went ahead and did something that affects the company without approval. And now he is mad he is not getting his way. The manager has to put the needs of the company ahead of this guy’s wants. It’s that simple. I would totally do the same thing. There is a process for approving vacation time, follow it or don’t get bent out of shape when you don’t the time off.

    Yes you can still travel with others even if you need advance approval. You plan ahead. Most family vacations are planned in advance because everyone needs to get the time off work approved. There are rarely vacation “emergencies.” Your birthday — as noted — is not an unexpected occassion. Mom falling and breaking her hip and being in the hospital — an emergency. An event that happens the same time every year — not an emergency.

    1. Case of the Mondays*

      Managers should generally have a contingency in place for a day or two after someone is expected to return from vacation. Many times flights are cancelled or rescheduled and the employee is delayed in getting back to work at no fault to his or her own. I know that is different than deliberately extending a vacation but it is generally good business practice to assume someone might be a day or two late getting back. Jet Blue had a fiasco in Boston last year where many people’s flights ended up being a week later. That’s extreme of course but something to keep in mind when traveling.

  24. MLT*

    #1 You say that Glenda has been unfairly treated and management may have a grudge against her. Sometimes we expect school room fairness when we are in a work situation, well beyond our childhood years. At work, people who give the most value generally receive better treatment – more opportunities, more money, more responsibility. When a person creates drama and negativity as Glenda does, her value drops considerably. She costs more to manage and the effect she has on morale presents costs as well. She may be very justified in her complaints, but her “us vs them” approach will cost her, and it could cost you too if you align with it.

    Your company has invited an outsider in to assess skills and capacity. People like Glenda reduce capacity. Offer Glenda advice that her attitude is doing her no favors. If she doesn’t heed it, distance yourself.

  25. mdv*

    #2 — My problem with this is the fact that the person CHANGED his travel (adding on) and booked it without permission first. I think you let him take it IF it does not require changing things for other people, and is workable, BUT, you tell him that this is a ONE TIME approval, and in the future he will be SOL on travel plans made without vacation approval.

    Said as a person “in a small department” — one of two employees of whom one or the other MUST be in the office… and the person who tries to be proactive and plan my time off to be as UNobnoxious as possible (a difficulty exacerbated by the fact that I am the only person in the office who can do certain things) looking at the calendar up to 18 months in advance.

  26. Hiring Mgr*

    On #2, this is why I write in my cover letters something to the effect of “I will need x week s of vacation time to be taken at MY discretion, with no more than three (3) days advance notice required”

    If an employer objects to that, i know it won’t be a good fit. Best to realize this up front.

    1. MLT*

      Wowee. If everyone did that, companies could be reduced to a nonfunctioning state based on their employees’ inability to plan more than 3 days in advance and all deciding to take two weeks off at the same time. I expect it’s hard to find employers who agree to that.

    2. fposte*

      Have you ever gotten a job with that in the cover letter? It’s not just the demand, it’s its placement in the cover letter that would be a dealbreaker for me.

      Your handle sounds like you’re hiring now. Do you find something like this effective when you see it in applicants?

    4. hbc*

      I respectfully submit that you can do this because you’re the manager. You can give people orders to cover all of your work on short term notice and blame them for not getting all of their work done and yours in your absence with no planning. Or maybe all of your responsibilities are so high level that literally nothing getting done on them for two weeks doesn’t have a real impact on the business. Most workers are not in that kind of position.

    5. Graciosa*

      Three days?!?

      “I’m leaving on Friday and I’ll be gone for X weeks. Yes, I know that I’ll be missing the annual conference, but my contract does not require my presence. It does require you to let me take my vacation regardless.”

    6. LBK*

      I’ve noticed you make a lot of comments like this (totally ridiculous things seemingly designed to alight the AAM commentariat) and I can never tell if they’re jokes.

    8. Ask a Manager* Post author

      I’m assuming that this is a joke. Hiring Mgr, as LBK points out, you like to do this :)

      Could I ask that you not? It tends to derail the conversation because people take you seriously.

      Geez, I’m micromanaging the comments all over the place in this post today. Sorry about that — just a few different issues jumping out at me this morning.

      1. Graciosa*

        Okay, now I feel silly for taking the bait.

        This is generally such a good forum, and I really enjoy hearing different points of view. I do see thoughtful commentary about points of view with which I disagree, so perhaps I’m not doing a good enough job identifying when this is done for effect.

        LBK, I’m really impressed that you noticed.

      2. CMT*

        I think Mercury must be in retrograde or something. Or it’s just a Monday and people haven’t quite finished their coffee yet.

      3. Katie the Fed*

        Maybe you need a vacation too :D

        (which isn’t undermine your observations at all, of course. I’ve just been noticing I’m more annoyed at things than normal lately because I haven’t had any vacay in a while)

      4. Hiring Mgr*

        My apologies! I was joking, but by no means did I intend to derail the conversation….I will refrain from this…

        Sorry!!

        1. LBK*

          FWIW I found it funny but deadpan/sarcastic humor is notorious hard to parse correctly via text :)

        3. Cath in Canada*

          I found it amusing, but only because I recognised your name and style! I agree that if I hadn’t recognised you, I might have joined the derailing though… ;)

  27. Cordelia Naismith*

    OP#2, can you elaborate on how your employee is bullying you? What is he doing that’s bullying? Is it just that he asked for additional time off after getting his initial request approved and is using his already-booked travel to try to “force” you to give him the additional leave? Or is there something else happening?

    If it’s the former, that doesn’t seem like bullying behavior to me. It’s inconsiderate and kind of manipulative, but not bullying. Your use of such an overly-strong word makes it feel like you’re overreacting to a minor irritant. If there’s no other reason not to (like it being a busy time of year or other people in his department already having approved time off for those days), then I’d just give him the time. People earn their vacation days and are entitled to use them.

    If he used up all his vacation time with the previous request and is asking for more on top of that, then I’d deny him the leave. If he hasn’t earned it yet, he doesn’t get to take it just because he already booked a trip.

    If there is something else going on that you haven’t detailed in your letter that makes a stronger case for the employee being a bully, then that changes things.

    1. fposte*

      I think “bullying” may not be the correct word, but I don’t think it’s necessarily overreacting–the employee is trying to make it the OP’s fault if he can’t take the planned extension. That’s a mean thing to do.

      1. The IT Manager*

        I suspect he’s also playing the “I will lose my deposit, if I change my plans” and what kind of **jerk boss** would want for that to happen. He’s trying to place the blame on losing the sunk costs on the boss who won’t approve his additional vacation days,

      2. Cordelia Naismith*

        I agree that it’s unprofessional behavior and makes the employee come across as a jerk. I just don’t think it meets the bar of being bullying. YMMV, I guess. It is a mean thing to do, that’s true.

        1. Cordelia Naismith*

          Oh, and also, I totally understand why OP#2 is feeling reluctant to give the guy the time. Nobody wants to let themselves be manipulated or give in to these kinds of tactics. But if he has an attitude or is being insubordinate, then I guess I think that’s a separate issue from the leave time. The OP should address his attitude with him directly, rather than making it all about the leave.

      3. JB (not in Houston)*

        I agree with the commenter above that “bullying” may be a perfectly correct word choice here, but the older use of the word, not the more recent one.

  28. Allison*

    2) OP’s employee reminds me of my classmates in college who would book their end-of-semester travel before knowing things like exam times and their move-out dates, and then whine about how the professor won’t let them take an exam early or how the cold, heartless housing office is unfairly “kicking them out” two days before their flight home. I’d always shake my head at these people who expected everyone to accommodate their travel plans, when they had to know that booking in advance without knowing their schedules was a bad idea.

    Wouldn’t surprise me if this employee was one of those students . . .

    The justification was, of course, that travel was expensive and booking early made things cheaper, and guaranteed them a spot on a flight during a busy travel season. My guess is, OP, your employee did something similar; when he changed his plans, he felt that he needed to book ASAP to secure a seat on the flight he wanted at a decent price, or needed to get a room at a hotel he knew was filling up and getting more expensive by the day, and he just couldn’t wait until the time was formally approved because he either assumed it would be, or he figured that if he locked in his travel you’d have n0 choice but to accommodate him.

    1. Brett*

      Though I waited to book…and ended up spending four Thanksgivings and three Christmas vacations on campus unable to go home because of the cost.

      1. Ad Astra*

        And this is why it’s a good idea for professors and university housing departments to have their calendars mapped out and distributed at the beginning of the semester.

        1. Allison*

          Oh no doubt, schools shouldn’t hide this information from students, I think the issue with my school (and this may be true with others) was that it took a lot of time to coordinate exam schedules, it wasn’t just when the professors wanted to give the exam, but when they could book a room for the test. I think this led to a lot of professors opting out of that madness and either assign final papers instead, or elect to have the exam on the last day of class.

          1. Ad Astra*

            Ah, I see. My school kept a master list of assigned finals dates, times, and locations. These were tentatively scheduled years in advance and were pretty much written in stone by the beginning of the semester, so they should have been in the syllabus. The only exceptions would be inclement weather (never happened, but we came close a few times) or students who have too many finals scheduled in a short period of time and have the option of rescheduling. I think the rule was if you had more than three finals in 24 hours, you could reschedule one of them, but the schedule didn’t change for the rest of the class.

            I always felt bad for people who ended up taking a final during the latest possible time on the last day of finals — so, like 2:30 p.m. on a Friday — because all the sorority houses usually closed Thursday night or at noon Friday. I think the dorms closed Friday evening, so you’d have to be totally packed up before you left for your final. :(

            1. Allison*

              At my school our move-out dates were contingent on finals, so they gave you 24 hours after your last final. BUT the freshman dorms closed on Friday evening, so if your final was late Friday afternoon you didn’t have much time to move after that. I tried getting an extension, but no such luck. My dad basically came the night before to get most of my stuff, and I spent the last night of freshman year alone, in a nearly bare, cement block dorm room. Super depressing.

            2. Talvi*

              Yeah, my undergrad school scheduled all finals well in advance, so you knew at start of term when your exam would be. First class of the semester on Tuesday at 2:30? Exam would be e.g. Dec 18 at 9:00 for every course with the first class Tuesday at 2:30. It was virtually impossible to have two exams scheduled at once (exams were either 9:00 or 2:00, and no longer than 3 hours so there was no overlap)

    2. jhhj*

      Most schools publish the last possible exam day well in advance — but then you could be stuck there quite a bit longer than you need to — so my undergrad place has an exam period from Dec 9 to Dec 22, and if you’re in an exam-light semester, you don’t know if you will end up lucky or not until November when the final exam schedule is published. (If you’re in an exam-heavy semester, they try to make the exams more or less evenly spaced. Or they used to.)

  29. Brett*

    #5 While Allison’s answer reflects the law on vacation and sick time, in practice many employers (especially public employers) with sick time will pay out that sick time on separation. In those situations, you have to look to the employer’s written policy to know how that payout is handled when you are fired.
    (Sick leave payouts combined with pension calculations are a reason that many public agencies are eliminating sick leave and vacation for PTO, which is not paid out.)

    1. SystemsLady*

      Really? I was just about to say that if sick time is included in PTO (which ugh I wish employers wouldn’t do), you’re probably more likely to get it paid back. But it does depend on the employer’s policy, and I’m not familiar with the public sector.

  30. Already Monday*

    I have a coworker who still lives at home (nothing wrong with that) who pretty much insists being off the same time during the holidays (Thanksgiving/Christmas) as her mom, who is a para-pro for the local school system. She has no concern or care that I might want to be off during the holidays to be with my family (we are the only 2 who do our particular jobs). I don’t begrudge anyone there time off, really we all deserve it, but I think my coworker should have a little consideration for me and not insist being off all week for Thanksgiving and Christmas every year. I have offered to flip-flop holidays with her each year but she doesn’t want to be reasonable. She thinks she is entitled to those weeks.

    I recently had a sit-down with my boss and explained that I don’t think one of us has to be here the whole week during those two weeks and he agreed, so we are going to see how it goes with both of us being off a week. I told him that if it proves that one of us does need to be here the whole week, I would be glad to either split the weeks or flip flop the holidays, but I will not continue to work all the holidays so he would need to address that with her boss, so he could address it with her. He did so and she flipped out when her boss talked to her. She just burst into tears and almost hyperventilated. She said that since she is an only child and her father abandoned them when she was a baby, the holidays were “special” for her and her mom. Yep, she played the fatherless, only child with a single mom card. I feel for her but she’s grown (24) and it’s time to be a grown-up and realize that she cannot always have the holidays off with her mom.

    TL;DR- Sometimes hard choices regarding time off have to be made. If your a manger, don’t be stingy. If your an employee, don’t be greedy. There are other people who want to be off, too.

    1. Artemesia*

      This would make me furious if an employee pulled this crap on me (but no I would not show the fury or have a hissy fit) The idea that this ‘only child’s wishes are more important that the desire of everyone else at work to have the holiday off is beyond infantile. It reminds me of inlaws who insist ‘Christmas is our day’ when their kids marry and have complicated families now to deal with. Mom and daughter can organize different vacations to be together; they are not the only two people on earth who want to be together at Christmas or Thanksgiving. I hope the boss made it clear that giant baby only gets one of these weeks next fall.

      1. Adam V*

        Heck, I’d have told the other coworker “you’ve had these same weeks off for several years, AlreadyMonday is going to get them *both* off this year and you’ll be working them both. Next year I’ll have both of you prioritize your requests and decide who’s working when.”

      2. Already Monday*

        She has been pouting and passive aggressive since she was told. Her boss is one of those who wants to be friends with her, so he has basically overlooked this behavior. It’s really a shame- this girl is smart, went to a private university and made fantastic grades, but has no ideal how to behave like a grown-up.

        My boss is the “big boss” so now that I have brought the concerns to his attention, I have no doubt that he will make sure that holiday time off will be fairly split.

    2. Nina*

      That’s completely absurd. The “I’m an only child” bs would just have me rolling my eyes. It’s also a way to kill morale in other employees.

    3. Limes*

      I mean not to sound harsh but – she really IS “entitled” to those two weeks of vacation if she works for them and it’s part of her earned benefits.

      It’s not really fair to deride her or be upset that she “doesn’t care” about your arrangements because it’s not actually her concern. She can’t (and shouldn’t) have to arrange her life and plans around your needs and you shouldn’t have to arrange yours around hers. Really this seems like your managers dropped the ball or like this should’ve been a brought to their attention a few years ago. Yes it’s pretty obnoxious (and the tears are ridiculous) but if it falls within the bounds of the company’s policies and her boss approved it, I don’t see how she’s being greedy by using what she’s been given and whatever manner she sees fit. And it sounds like the same thing would’ve been approved for you had you asked first, no?

      The way I see it, her using her time off shouldn’t bar you from using yours. And if does that’s not really her fault – it’s management’s … she should be free to ask and they should be free to say ‘No.’ If they don’t, don’t get mad at her.

      1. Adam V*

        She’s not entitled to *those* weeks, though. She’s entitled to two weeks, spread across the entire year.

        Management is entitled to say “in the interest of fairness, since those particular weeks are highly sought-after, and you’ve been granted them for the past few years, we’re going to deny your request this year so that AlreadyMonday (who a) also requested those weeks and b) has had to work during those the last couple of years while you were off), can take them instead.”

        You’re right, it’s a management thing. However, that doesn’t mean crying and hyperventilating when told ‘no’ is appropriate behavior.

        1. Adam V*

          (And that’s just me saying “this year AlreadyMonday gets both weeks off”. It’s entirely possible, since it wasn’t stated, that the boss instead said “pick the week you’d prefer to take vacation, and you’ll have to work during the other one”.)

      2. LeighTX*

        I disagree here—it IS greedy to hog the best holidays for yourself. Of course she’s entitled to her vacation time, but teamwork is part of office life and she’s not really acting as part of a team in this situation. If she knows that AlreadyMonday has to be there when she’s not–which means that using her time off DOES bar AlreadyMonday from using hers at that same time–then it’s only polite to be considerate of AlreadyMonday and take turns with the holidays.

        1. Limes*

          I think the question is whether or not Employee 1 using her vacation time ACTUALLY bars AlreadyMonday from using hers. I think in most people’s mind the answer is automatically “Yes” since in our society, we often have the mindset that resources are scarce and therefore if one gets something the other can’t. But we should really be shifting our thinking to, “Just because someone gets something, it doesn’t automatically mean there’s less for me.” Which is pretty much demonstrated in the fact that all AlreadyMonday had to do was speak to her manager and he is now giving her the same time as Employee 1. It’s really not Employee 1’s fault that AlreadyMonday didn’t ask (not trying to be snarky, I totally get where you’d be coming from given our cultural views here).

          That said, I still feel this is management’s fault and not Employee 1’s. AlreadyMonday shouldn’t HAVE to speak up for those two weeks – they’re her entitlement too – but it looks like a case of the boss not knowing it was a point of contention because it wasn’t ever brought up. Just another case of “leaning in”.

          1. Already Monday*

            It used to, before I asked if we could try something new. They (management) felt that one of us needed to be here pretty much everyday during the holiday season (Thanksgiving, Christmas) because we have access to certain files and information that others do not and we can also back up another dept if they get really busy.

            The lady who held the position before employee 1 and I switched holidays each year so that we both got time off at the holidays. Employee 1 has been here for 3 years now and she only wants those two weeks off every single year. As I said, I don’t begrudge her time off, but if the new plan doesn’t work, I am not going to work every Thanksgiving Christmas week every year so she can be off with her mom. Since my boss now knows what is going on, I think the chances of that are slim. If they decide the new system doesn’t work, I have no problem switching holidays each year and if she doesn’t want to compromise, I’ll get petty and request off years in advance.

    4. Katie the Fed*

      The problem here is the boss. The boss should be managing leave, not leaving it for you two to sort out. And the boss shouldn’t be telling you what the coworker said/did during a private conversation between the two of them.

      1. Adam V*

        It’s entirely possible this just happened somewhere that the coworker’s reaction was visible. What with the push for “open floor plans”, it’s not always possible to find a quiet place to talk.

        Not to mention, I wouldn’t have expected flipping out, bursting into tears and hyperventilating over a conversation which probably began “you’re going to have to reschedule some of your vacation time, AlreadyMonday has asked for that time off too and pointed out she’s never gotten to take that time off since you’ve taken it the last 4 years”. Maybe the reaction just drew a lot of attention? I dunno.

      2. Already Monday*

        Her boss did not tell me what was said. He called her into his office and then about 2 minutes later the crying and hyperventilating started and it was so loud, the entire office noticed. I’m probably less than 6 feet from his office so I hear pretty much everything. MY boss, who has an office next to her boss, actually knocked on the door and ducked his head to make sure everything was ok. She also went to the other person in her dept (3 person dept, Boss has small office, 2 employees are in cubeland) and loudly complained that she might not get to take vacation with her mom anymore because “other people are complaining”.

    5. Purr purr purr*

      I wouldn’t have the patience to deal with it like you did so kudos to you for handling it politely and properly by going to your manager. I can’t understand your colleague’s refusal to do the flip-flopping; she must be extremely selfish.

      For me, I’m *insisting* on this Xmas off this year. I worked last Xmas and now I’ve been scheduled to work this Xmas too. That’s just not going to happen when there’s two other people on my schedule who enjoyed last Xmas off. I’m willing to leave over this because it’s a repeated pattern in that I’m always scheduled to work public holidays too. I’ve mentioned it and the person who writes the schedules just gives a smug smile. I dislike him immensely!

  31. Erin*

    #2 – Is this really happening during a peak time? Like, it’s early April and you’re a CPA firm, kind of peak time?

    If so, and if it’s possible and makes sense, maybe you could change the PTO policy to state that you can’t take time off during a certain window frame of time – or, that you need a certain advanced notice to take time off during that window (more than the usual).

    Also, I would directly call him out on the fact that he got time off approved, and then went ahead and extended – and booked – his trip before additional time was approved. I mean, come on. That’s inexcusable and should be nipped in the bud right away.

    If it were me, I would approve the birthday off, but not the additional trip time. Hope that airfare, hotel, and whatnot are refundable, jackass.

  32. LQ*

    OP #2

    You asked how to handle this. I would say have a conversation with your employee. *Assuming this specific incident has passed at this point* Sit down and say I expect vacation to be handled *however* in the future. Vacation requests not handle this way won’t be approved. (Or whatever the consequence is for you.) Have a clear plan and be able to answer questions. If this is a change, it is even more important. Then if you need to have that conversation with your whole team to let everyone know what the policy is. Especially if this employee is one to complain and would tell other people on the team OP won’t approve any vacation anymore unless you get it signed in triplicate first! If you’ve told them what you actually need this will help you a lot.

    (If it hasn’t happened I’d try to approve this one, say this time only, all times in the future will be handled X. Even if you don’t like that this employee did it this way it will show other staff how you handled it.)

  33. Vicki*

    #1 – I’m going to disagree. Riding in the back seat of the exec’s car on the way to the airport is NOT going to provide the OP with a “chance to re-establish a positive working relationship” with those execs. It will, however, destroy your relationship with your co-worker because she’ll view it as giving in (at best) or buttering up (at worst).

    This is a Ride to the Airport, not a marriage. Smile, don’t make a liar out of Glenda**, and “re-establish a positive working relationship” at the conference.

    ** Consider the ramifications of saying “yes, I was going to ride with Glenda, but I’d rather ride with you guys instead”.

      1. Desdemona*

        Yes. It’s risky to be friendly at work with someone on the outs with management, especially if management’s treatment of the person is unfair (for example, a manager who’s threatened by someone’s intelligence, so makes it a point to keep the subordinate way down). OP appears to have accepted that risk and has offered Glenda emotional support and a reality check that her treatment may be less work-related than personal. Glenda in turn crossed a line by assuming that because OP is willing to befriend her, she’s willing to jettison her other working relationships. I like Allison’s suggestion. It allows the OP to do what she considers best for her own career, continue to be Glenda friend if she so chooses, and invites Glenda to take an opportunity to try to mend bridges without making a moral judgment about her if she refuses.

  34. CdnAcct*

    I once had a problem booking vacation time that upset me so much that I made a comment on our employee survey, I brought it up to senior managers when they asked about problems, and I still mention it when discussing bad management. This vacation time that I asked for was one afternoon off.

    First, I asked for the whole day off a couple weeks in advance. This was during a period where the department around me was busy but winding down, and I didn’t have any deliverables. My manager hemmed and hawed and said, let’s wait and see.
    So I waited, asked again on the Monday (it was for Friday). He said, I don’t think so, I don’t feel comfortable letting you go for the whole day (I was more of a report checker and by then most of them were done already, but he was always pretty insecure about not having me available for some reason) He also had my number in case of an emergency. So I asked for just the afternoon – I had booked an afternoon tea with a friend where you had to book on a weekday. Again, he said let’s wait and see on the actual day.
    The day rolls around and I’m not busy at all, haven’t gotten any questions or requests for help. I ask, and he doesn’t want to let me go, so I say I’ll go but come back after, so it’s more of an extended lunch hour. He agrees.
    I come back after two hours out, and he gives me shit (actually pulled me into a room and lectured me) because our big boss came around and asked him something, and I wasn’t available right then to run it – I can’t even remember what it was, it was small, and the boss didn’t care about waiting for an hour.
    I had a lot of issues with him before that, but that frankly made me lose any remaining respect I had for him, and I’ll NEVER work for him again. He probably doesn’t even remember this incident. Jerking people around about their time off is awful management – that two-hour tea was barely enjoyable because I was so stressed about getting back.

  35. Lisa Petrenko*

    The question about time off… I’m guessing your company is luke most where people have a limited number of days vacation (most are 2 to 3 weeks, lucky ones maybe 4), so you really should do your best to approve most requests (especially just a long weekend! ). The only time you should say no is maybe when it overlaps someone else’s time off or if you already gave notice that x is a bad week because (whatever, there is an inspection, etc.). Saying yes to most and having no as a very rare exception should be the rule. If you say no, it really causes resentment and a lack of loyalty to the job and frankly looking to get out ASAP.

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