my staff keeps requesting time off at the last minute, even though I keep asking for advance notice

A reader writes:

I am a manager in a small office (me, my boss, and my three direct reports), within a very large organization. The size of our office is a bit unusual; most departments have 50+ employees, and many are 100+). As a result, many of our HR policies are set up in an extremely structured way. Traditionally, our office and other small offices have been given a great deal of latitude in applying some of the policies. For example, our company policy is that employees must give at least two weeks notice in writing when requesting vacation time. Another formal policy is that vacation requests can be denied based on the number of other people already scheduled for vacation.

We’re a little more flexible, so I’ve stated, many times, that I’d like one week’s notice, and verbal requests are fine. I have explained (with words! repeatedly!) that I need about a week to adjust staffing assignments during vacation time. And depending on where we are with workflow, during quieter times, it’s fine to have two or three people out of the office at the same time, but busier times present more of a challenge.

Yet somehow we have gotten to a place where all three of my direct reports are in the habit of requesting vacation days, via text or a phone call, the night before the day of planned vacation. I thought it was okay to approve the requests if the work demands of the office were low. I have framed my responses to say “yes, you can take tomorrow as a vacation day because we have a fairly low-key day planned, although our general practice is to request vacation at least a week in advance.” I don’t want to be a jerk and not allow someone a vacation day if it truly would have been okay, work-wise.

But it has been happening so consistently that I resolved to enforce our already fairly casual policy. Sure enough, the next time it happened — a text in the evening asking for a vacation day the following day — I called the employee back, prepared to decline the request — and, we had a large project scheduled and another person was already scheduled to be on vacation, so I could legitimately say that it was too late to accommodate another person being out of the office. When we spoke, the person was extremely apologetic and emotional — she had made a mistake (which she readily owned up to) about the date that her son was on military leave. This was his one day to spend with his family. I thought this was compelling, and tried to keep it in mind when I was scrambling to get the project completed by deadline.

Most recently, we had a major external review scheduled, definitely an “all hands on deck” situation, and I informed employees about two months ahead of time that no vacation could be taken during the review days. Shortly after, another staff member came to me and asked for an exception — could he leave early on the last day of the review, because he and his wife were traveling out of town for a family reunion? He had already put in a great deal of quality work for the review, and I wanted to consider his efforts. I agreed that he could leave the office early on the condition that a specific review-related project was completed before he left (a group project which everyone was contributing to). On that day, we were about 80% finished with the project, and he announced he was leaving. He said, in what I think was a sincere effort to make it sound cheerful and friendly, that he needed to leave at that moment because “his wife made it very clear that they needed to avoid rush hour traffic for their drive to the reunion.” I was pretty steamed, because as his boss I thought I had made it very clear that he needed to have this project completed before leaving.

Some additional factors are that both my boss and I have crisis management roles, so the two of us are often called to physically be present at another site, or might be called to work on weekends or overnights. If either of us are called in on a Tuesday at 2 am, we might not go to the office during business hours on Tuesday. Or one of us might unexpectedly be called to work at another site. My direct reports all have more typical 9 – 5 office functions, such as budget work, fielding phone inquiries, and assisting visitors in the office. Even though everyone intellectually knows that my boss and I have a different type of job when it comes to being at our desks, I think it’s creating a perception that attendance in the office is flexible. It’s one thing to explain in a staff meeting the kind of work I am doing during a crisis call, but in a sense, I think it’s somewhat invisible work to my staff members because their direct experience is that I’m not in the office, that I’m vaguely “somewhere else” during the work day. Maybe I’m working, maybe I’m eating bon-bons and shopping … ?

And, all three are very nice people who are generally good employees, and work well with each other. I am not aware of any resentment among these folks that any one person’s unexpected absence is creating a burden on the others. As far as I know, they are willing to pick up extra work on days when someone else is out, because they feel it is reciprocal.

The missing piece, maybe, is that even though they are willing to do extra work, it also creates extra work for me, and it can ripple through projects in ways where I am the one working late, rushing, asking other offices to give us extended deadlines, or putting other important tasks aside. It’s causing stress for me. While they can reciprocate to each other, they cannot reciprocate *to me* many of the aspects of my job that get put on hold during times like this. I feel that in some situations, such as illness or emergencies when an employee would take a sick day, that’s part of what I am compensated for as a manager — to take on the responsibility of closing the gap when we are short-handed without notice. But isn’t the whole point of requesting vacation days in advance to allow the office to be better prepared for those times when people are scheduled to be away?

How can I get this back on track? My boss is trying to be my ally in this, but due to his own duties, he’s a little distant from the day-to-day office operations.

What are you doing after you grant these last-minute requests? Because I can totally understand why you go out of your way to try to be flexible with people (that’s a good thing) and why you don’t want to tell someone that she can’t see her kid on military leave — but you also need to follow up with them afterwards to make sure that they really do get the message that they need to change how they’re handling this stuff. I know that in the moment when they’re making the request, you’re reminding them that generally you want more notice — but then you’re going ahead and saying yes anyway, and that’s probably the part that’s sticking with them the most.

I think they’d get a different message if, once they’re back at work, you followed up with them and said, “Hey, what happened the other day? That seemed like a request you could have made in advance, and while I tried to make it work for you because you’re a good employee, it meant that I had to reshuffle my own priorities/work late/pull people off other projects.” In other words, treat it like you’d treat other types of mistakes — help the person clean it up in the moment, but talk about it afterwards to make sure you’re creating some accountability and to get aligned about how to handle it differently in the future.

It also sounds like you need to get more comfortable with the idea that sometimes it’s reasonable for you to tell people no. When you’re managing good employees, you do want to try to say yes where you can — but there are times when you can’t and that’s okay, as long as you’re being reasonable and you explain your decisions. That guy who agreed to get a project finished before leaving early, and then left early even though it wasn’t done? That’s a big deal — he was breaking a clear commitment that he’d made to you. It sounds like you felt helpless to stop him, but ideally you would have spoken up and said, “We actually agreed that you would need to have this done if you wanted to leave early today, and it’s only about 80% of the way there.” If he pulled out the line about his wife making it clear that they needed to avoid rush hour traffic, you could have said, “I sympathize, but I really do need you to stick to our agreement to get this done before you leave.” (Alternately, depending on the importance of the remaining work, you could have let him leave but then followed up with him when he was back in the office to ask about what happened and why he didn’t follow through on the commitment he made, and to make it clear that you take that seriously and it can’t happen again. Either one of those creates some accountability; it’s your call as a manager to decide which one makes the most sense in that particular context.)

But I’d also take a look at the policy itself too. In general, I’m a fan of adults managing their own time off, and I wouldn’t love a policy that required a week’s notice for just a single day off. Adults should be able to look at their workloads and think, “You know, if I push to get everything done by Thursday, I could take Friday off without it impacting anyone else” and then do that. And I’d be annoyed as hell if I knew I could manage my workload to make that go seamlessly, and yet was still told no because I didn’t request it a full week ahead of time. If it doesn’t impact anyone but me, it’s infantilizing.

Now, in your context, it sounds like absences do impact other people, at least some of the time. But that’s the place where I’d put your real focus, more than on the one-week policy.

After all, what is it that you really want out of this policy? Presumably you want to make sure you’re not caught short-staffed, having deadlines missed, or having to reshuffle your entire day. So why not build your policy around that? For example: “In general, I need a week’s notice to approve time-off requests, so that I can ensure that work is sufficiently covered. However, we can occasionally work with shorter notice if you’re able to manage your own workload so that no one else is impacted and no deadlines are missed. In those cases, I may ask you to walk me through what you’ve arranged.”

That will drive home that there’s often work involved in covering for absences, and that it’s not always as simple as just skipping off for the beach and not thinking about the impact on other coworkers.

Approaching it this way doesn’t mean that you’d never help people out if they can’t arrange coverage on their own. For example, with your employee who got the date of her kid’s military leave wrong, you’d still presumably help make that happen if she needed assistance, because being flexible with good employees when life throws surprises at them is part of being a good manager. The idea is just to hold people to the same level of responsibility and consideration in return.

Read an update to this letter here.

{ 214 comments… read them below }

  1. Katie the Fed*

    Agree with Alison – you need to focus on the work and not the 1-week notification. And you need to say no sometimes – they need to know that there are consequences, and that work comes first.

    When your guy left before the project was done – that was an absolute nonstarter. That’s not a situation where you need to sit there and take it. Tell him to finish it. I had a guy once leave before a big project for Congress was due the next day. He just left. And when I realized he was gone and it wasn’t done, I was LIVID. And then I picked up my phone and told him to return to work and finish it. He wasn’t too happy either. Actions have consequences. He made a choice to leave early without finishing his work – so he can deal with the consequences of that.

    1. Basia, also a Fed*

      I agree 100% with Katie. It is difficult to manage people, and I’ve struggled with exerting my authority myself. But for your staff to respect you and follow your directives, when something like this happens, you need to say “I’m sorry, but when you asked to leave early, I approved it under the condition that you wouldn’t leave until this was finished. Therefore, I need you to finish it before you leave.” The fact that you aren’t enforcing what you say is causing your employees to take advantage of you – they know you don’t mean it. Good luck!

      1. ZenJen*

        yeah, when I have to weigh in on conditions of letting my staff take PTO in certain situations (a busy period, last-minute), I make sure I have an email reply, so that there is SOMETHING in writing about what my decision was. I DON’T leave it to just a verbal reply that someone can say “oh sorry, I forgot”. If there is any further issue on it, I resend them my previous email, so they are reminded of what I told them–that’s part of the accountability. It also makes sure I’m treating all of my direct reports fairly+equally.

        1. Trillian*

          Doing it by email would also let the OP create templates to cover the various situations, saving them having to spend time and energy working out the wording. Two or three emails would cover refusal or conditional agreement.

          The OP should also think through in advance how they’ll deal with people who ignore the conditions and take off anyway, because I suspect that will happen.

        2. Vacation Manager OP*

          Having an email record is something I will definitely do in the future — even if it starts with a verbal conversation, it’s easy enough to send an email to sum up what we decided upon. Thanks for the good tips.

    2. Mallory Janis Ian*

      Yeah, all the other requests for time off seemed pretty reasonable to me, but the guy leaving without finishing his work, because his wife said they needed to beat rush hour traffic, was out of line. He doesn’t answer to his wife regarding his work; he answers to his boss for that.

      1. Koko*

        Yes, OP seemed like a nice reasonable manager until I got to that one. Caving in to an employee’s spouse’s preference to avoid traffic makes you a doormat. It wasn’t asking him to skip the event or miss a flight, just to put up with a little traffic because he has a job that prevents him from always being able to leave town in the middle of the afternoon. A lot of people have jobs like that and they suck it up and sit in traffic.

        As Red Forman said, “Work is work. You don’t show up late, you don’t make excuses, and you don’t not work. If it wasn’t work they wouldn’t call it work. They’d call it Super Crazy Happy Fun Time…or Skippity Doo!”

        1. Kate M*

          But even if it were a case of missing a flight or something, it’s still the employee’s fault for assuming that he’d be able to leave on his own schedule. If the project was expected to be over at 4pm, I still wouldn’t book a flight until much later (maybe 9pm if you’re an hour from the airport) so that I could make sure to build in time in case it ran over.

          In general of course flexibility is good, but when your boss tells you explicitly that you have to be there for something, you’re there barring an emergency. If you take the risk at booking an earlier flight, that’s a gamble you might lose.

    3. Katie F*

      Yeah, I think letting the guy leave early was a mistake. He knew you wanted that project done and he knew it was his responsibility to ensure it WAS done before he left. I’d have called my wife (or, er, husband in my case) and said, “I’m sorry, honey, we couldn’t get the project done and it’s essential to me being able to leave. I’ll be home at 4:30 and we’ll get on the road.”

    4. animaniactoo*

      Yeah, that’s the point where you need to make it clear that his wife’s priorities are not *your* priorities. And that since it is work hours, your priorities come first for anything less than the sky falling in. So, sorry bud, no deal. Leaving early was conditional and the condition is not met.

      1. Sketchee*

        One thing I’ve found helpful is to acknowledge what they want. “I wish it worked out that way. Totally understandable that you’d want that. Wouldn’t it be great if the timing and workload allowed that.”

        This let’s acknowledge’s Allison’s point that when it’s possible, allow and encourage flexibility.

        Even more directly you can ask “I understand that you’re hoping to leave early. As you know, we have to meet the deadline because Other Department Needs X/For the Big Meeting/Whatever reason. What’s your plan for completing this by the deadline?”

        Show that you’ve thought it out and ask them to join in with that thinking process. The hope would be that they’d use their flexibility responsibly. Ultimately, it’s the manager’s call though. “That change in plans doesn’t really work for me. Let’s get this done today as we originally planned.” Be considerate and honest. It goes a long way

        1. animaniactoo*

          Yeah, it can be very simple “Well I can understand why she’d feel that way, but unfortunately I need you to help finish this first.”

          I suspect to some extent that the OP was flabbergasted and caught off guard and wasn’t able to think quickly enough to stop him before he went out the door. This is the kind of thing that experience and practice will bring.

          1. Vacation Manager OP*

            Yes! Being flabbergasted and caught off guard is exactly what was happening. That, in combination with not realizing he was wrapping up to leave (for the most part people are working on their parts of the project in their own offices) so he was literally walking out the door, had me pretty speechless. (If you can picture this happening on a sitcom, it would have been a shot of the elevator doors closing behind him with me saying “whoa, wait a minute …” to an empty hallway.) Thank you, Allison, and the other commenters for providing some solid scripts to have at the ready.

    5. Recent Reader*

      “. . .they need to know that there are consequences, and that work comes first.”

      Ugh, no. Yes, work is very important, but it certainly doesn’t come first (at least, in my life). It’s just a means to an end. My family comes first.

      1. Katie the Fed*

        Well, I didn’t mean that as a general philosophy – it was related to requesting leave. Your leave requests depend on the needs of the employer. I’m usually quite flexible, but you don’t get to roll out on no notice and leave the team holding the bag.

        1. Mallory Janis Ian*

          Exactly. The rest of the team has family or other commitments that they consider important, too. “Work first” doesn’t necessarily mean that you become a workaholic, sacrificing any and all family time to the job; it means that when you have a commitment, you finish it before you waltz out early in the middle of the afternoon.

        2. JumpyJess*

          …”but you don’t get to roll out on no notice and leave the team holding the bag.”
          Right!! Especially when they have just thoroughly assured you they won’t do exactly that.

    6. Vicki*

      I’ll make it even clearer. One week required notice is NOT a “fairly casual” policy.

  2. CMT*

    Hmm, I can see how a week’s notice might be a lot to ask for just a day off, but I can’t imagine texting my boss the night before to ask for a vacation day. I would just never do that. (If I were sick, yes, definitely.) A whole day off would be something I’d try to ask for at least a few days in advance, or at they *very* least, while at work the day before.

    1. Katie the Fed*

      Eh, it’s not a big deal for me. It’s more like “Hey Katie – I’m really tired/feel like going hiking during the beautiful weather/feel like a romantic weekend away. We’re pretty quiet tomorrow – do you mind if I take the day off? Sorry for the short notice!”

      I’ll say yes like 95% of the time. Or sometimes I’ll tell them as long as they’re local it’s fine but I reserve the right to call them in if we need.

      1. CMT*

        Hmm, maybe I need to loosen up my own standards. I seriously doubt my boss would say no in a case like that, I just wouldn’t feel comfortable asking.

        1. Katie the Fed*

          I figure I’ve built up a pretty big bank of goodwill – coming in on weekends, staying late, etc. So I don’t feel bad taking a withdrawal once in a while :)

      2. Ask a Manager* Post author

        Yep, exactly. If your workload allows it, it’s not a problem. It’s treating people like adults and trusting them to manage their work responsibly. The issue is when people aren’t doing that.

      3. LAI*

        Hmm, this is good to know. I just took a day off after asking only the week before, and I was feeling pretty guilty about that. It’s more typical in my office for people to plan their vacations months in advance, especially in the summer because a lot of people try to take time off. To ask for vacation only a day in advance would just be such a departure from our normal routine that I don’t think I could do it… but good to know that some managers would see it as no big deal.

        1. fposte*

          I have positions where that would work and positions where that wouldn’t. So far people are pretty good about knowing which one they’re in.

    2. Countess Boochie Flagrante*

      There was exactly one time I did that, and it had a lot to do with being overseas and not within cell range until the night before. (I returned from vacation seriously ill — not recommended!) But that was a pretty exceptional situation.

    3. irritable vowel*

      I agree. I don’t think there needs to be a rigid one-week notice policy, but a vacation day is something that should be scheduled with a little bit of forethought whenever possible, not just “I think I’ll take tomorrow off; let me text my boss at 9 pm.” I agree that adults should be trusted to manage their time, but a last-minute request to take a vacation day (that isn’t about something urgent that just came up) says to me “I just don’t feel like coming into work tomorrow,” and that seems unprofessional. Better to make that a sick day (aka mental health day) than a vacation day, IMO.

      1. Ask a Manager* Post author

        I think the more senior you get, the more acceptable it is to do that — because you’re trusted to manage your own workload and decide if you can or can’t do that on any given day.

        1. irritable vowel*

          Yes, agreed, but I think whether you are also a manager affects that. If I didn’t manage staff, maybe I wouldn’t mind saying to my boss “okay if I take tomorrow off?” But I feel like I need to set a good example for my staff, and I wouldn’t feel comfortable messaging them in the evening to say I’m not going to be in the next day, because I wouldn’t find that acceptable from them unless it was for illness/emergency. (If I’m going to be out sick, I tell them that.) My current staff are great but I’ve definitely had people on my team in the past who really needed to understand that time off should be structured.

          1. Koko*

            I do think it’s probably dependent on your staff dynamic/culture. Our department head and VP each manage a full team and it’s not unusual at all to get an email on Thursday from one of them announcing that because the forecast for this weekend looks so great they’re going to take tomorrow off.

            Most of our senior employees have the same flexibility, but there are junior employees whose work isn’t as flexible who can’t do that. I think they understand why it’s OK for some of us and not them, though. Those employees are paid hourly, work on desktops in the office, and leave the job behind at 5 pm. They come in at 9 am the next day and see the emails that everyone else was sending at 7 pm, 9 pm, 6 am, or over the weekend and they understand the trade-offs involved. We are given more flexibility than them in which hours we work, but we work a lot more hours.

      2. LQ*

        I used to do this often at my old job. All of my meetings would get cancelled and I’d look at my work load and be like oh! A DAY! And I’d take it off. But I knew what my workload was, I knew what I was responsible for. And often that would be the only way to take a day off at some parts of the year. It wasn’t ideal, but I think that there is nothing wrong with looking at your schedule and going, I’ve been running hard on all these projects and this day opened up, I’m going to take the day off.

    4. Koko*

      Hand to heart, sometimes I decide at 7:00 am when my alarm goes off and I don’t feel like I’ve gotten enough sleep that I’m going to take the day off. I’ll fire off an email from my phone in bed and then I go back to sleep for a couple of hours more.

      In terms of workload coverage, when it’s short notice I usually say that I’m just hanging around the house so they can call me if they need anything. If I had anything due that day, I’ll get it finished sometime after I get back up, and I’ll work on anything due the next day that I don’t think I’ll be able to complete unless I work on it that day, but otherwise I enjoy the day off.

      Since the objective of taking the day off was primarily to get more sleep rather than to not work at all I consider it a pretty fair give-and-take that I can take off at the last minute as long as I’m still available for emergencies and understanding I might have to do *some* work to keep projects moving.

      1. Edith*

        At my work that kind of a day off is its own category of leave. We get two of those days a year.

        1. AvonLady Barksdale*

          I would love to implement that here. And call it a “F*** It Day”. Or, in our case, “F*** It, Do Not Call Me Day”.

          1. Oryx*

            Someone in, I think, Friday’s open thread mentioned at their job all employees get one Ferris Bueller day which serves the same purpose.

    5. Kira*

      I can’t imagine asking for a day off with just a few days notice at my last job. We had an elaborate time off request procedure that required collecting time off forms from HR (who would respond in a couple of days), then preparing a sheet for your manager (who might be working from home and wouldn’t be able to physically sign the form for a couple of days), then send that back to HR, who would pass it to the top executive, who would decide whether she felt like approving it or not on an arbitrary basis.

      It was not a conducive process for one-off vacation days.

      1. SophieChotek*

        Yes, I agree. I can’t either.
        I have to put in a request in writing a month in advance, and it has to be approved by two different department heads.
        The idea to decide the evening before just boggles my mind.
        But I guess we established from my “Time Off” post on Friday a few weeks back…my work place isn’t always that…

      2. Oryx*

        Agreed, my last job wasn’t either. I had to get it approved by three different people.

        My current job, we are trusted to manage our own schedules and check the team calendar, but I just put in a request through our payroll system and that’s it.

      3. HoVertical*

        Oh yes, I’m very familiar with that kind of process. I worked for my state’s DMV back in the 90s and HR were absolute sticklers for their beloved three-part forms, that had to be signed out there, filled out in front of the department head, and then co-signed by the department head, division manager, and requesting employee.

        There was no such thing as a one-off vacation day, and, when I went into early labor with my first child, I didn’t hear the end of it for over a year. “What? What do you mean, you’re in labor…but you’re still coming in, right?” (Slight – only slight! – exaggeration.)

    6. CMT*

      Seeing the variety of responses here is super interesting. The more I think about it, the more I think I would definitely have leeway to ask for a last-minute day off if I had all my ducks in a row at work and no deadlines or meetings. I just have this ingrained idea that it’s unprofessional to ask for something like this last minute, and it does sound like in some work places, it would be viewed that way.

    7. Murphy*

      Yeah, I’ve done it. I’ve had staff do it. If it really doesn’t impact anyone else, I don’t care. Hell, I don’t even really need them to ask me, just say “I’m thinking of taking tomorrow off. A, B, and C are covered and D & E can wait until Monday, you cool with that?”

        1. Murphy*

          But that text could come in at 9 pm and I’d be cool. Ditto if it came in at 7 am. But I work in a world where cover-off isn’t a big deal. So long as project aren’t left undone or deadlines not met it’s fine by me.

  3. Tiffin*

    I’d have a meeting and emphasize that you have been much more flexible than the general company policy because you appreciate their work but that if they can’t meet your current request, you will begin to require 2 weeks’ notice. Should you have to do that? Of course not. However, it seems like these 3 are taking advantage of the relaxed attitude in the office. I can’t believe someone had the nerve to leave before finishing a project to miss traffic!

    I agree that adults should be able to manage their work, but it doesn’t sound like these people are completely doing that. Also, I think it’s a general courtesy to give people a head’s up as early as possible when you are going to be out. For a vacation, it should be well in advance; for just a day, a day or 2 of notice would work, but the night before (and after hours, no less) should only be allowed for emergencies. As the OP noted, you may think you have your work covered, but there could be ripple effects that you don’t know about (say, Tom e-mails the night before to say he wants a day off when you’d planned to help him cover Sally’s work while she was out).

    1. Florida*

      I don’t know if I would have a meeting with the whole department. I would speak to people one on one. I call those punishing-the-whole-class because it reminds me of school when one person did something bad so the whole class got punished. Even if most of the class did something wrong, there were people who didn’t, and they shouldn’t be punished for it. That creates resentment.

      Usually,the offenders aresitting in those meetings thinking, “This doesn’t apply to me. I’m not the one who requested the vacation time.” Or the employee who truly is innocent and always follows the policy is becoming resentful of her co-workers because she is sitting in this stupid meeting because they are requesting vacation time.

      If you have three employees who are messing it up, I would talk to each of them individually about it.

      1. Not a Real Giraffe*

        It sounds like there are only three employees in OP’s department, though, so I think a team meeting in this case is appropriate.

        1. Artemesia*

          It is even less appropriate in a small department to have this meeting. The guy who waltzed out of work with his work undone will feel resentful in a meeting, but appropriately confronted in a one on one. Yes, he should have been told he can’t leave till the work is done, but everyone makes mistakes on the spot sometimes. He needs even now long after the event to have the discussion. It is easy enough to speak individually with 3 people than 30. In a meeting, the woman whose son was home on leave will feel singled out, the guy who waltzed out will feel resentful rather than appropriately reprimanded because it is public and the other guy will feel unfairly targeted. One on one is the way to go.

          1. AD*

            It sounds like all 3 employees are doing this, not just the one guy. And it’s absolutely a manager’s prerogative to call a team-wide meeting to address a problem that’s occurring throughout the group – whether that group is 3 people or 30. Just because the team is small shouldn’t mean that employees will be more sensitive to the content of the meeting. I don’t get that.

            1. Not So NewReader*

              I see nothing wrong with recapping the rules and letting them know no more midnight texts unless there is an absolute emergency and work must be caught up before you leave. All that can be said without naming names or particular situations. And it can be expressed that everyone is being told at the same time so everyone knows they are all being told the same thing.

        2. Laura*

          I would include it in the next regularly scheduled meeting. “Hey guys, I’ve had to do x, y and z recently since we’ve been getting lax with the vacation time.” The military leave does make sense, but the guy that ducked out on the project? Yeah, I would include that on his annual review.

      2. Muriel Heslop*

        Teachers do that punishment to *cause* resentment. I don’t use that tactic myself but many of my colleagues turn to peer pressure to enact better behavior. Sometimes it works, but it also teaches by example a poor way to handle things later in life.

        1. Florida*

          You are probably right that sometimes it is to cause resentment. And there might be times where using peer pressure is the best way. (I can’t think of an example right now, but there is probably some time where this is a best practice.)

          Often though, I think teachers (and managers) use it is because it’s easier because it’s less uncomfortable for the manager. It is easier to put a sign in the office kitchen that says, “Clean up your mess,” than it is to talk Messy Marla who is the only one who can’t wash her dishes.

          I was thinking more of when people punish the whole class (or work team) because it’s easier, not the ones who are trying to use peer pressure. I think Tiffin was suggesting a meeting because it’s easier, not because you can enlist peer pressure. (Tiffin, correct me if I’m wrong.)

        2. Katie F*

          And you know what, it works! It causes all the kids to band together in their resentment of the teacher. That’s what those teachers are going for, right?

          Because… that’s the only result -I- ever saw from tactics like that while I was in school. It took my otherwise fractured and constantly fighting class and united us in a passionate hatred of the Teacher Who Punishes Everyone Because Brandon Drew on His Desk.

          1. Chinook*

            My class had an even better strategy when the board stated you couldn’t publish an entire class unless the entire class was the problem. One student was the appointed to explicitly behave so that that option wasn’t open to the teacher. :)

    2. fposte*

      But they’re not doing it because they’re not being held accountable, not because the current policy is bad. The guy had the nerve to ask because he thought he was going to be told it was okay–and he was told it was okay. It doesn’t make any difference how many weeks the OP officially requires if she always grants vacation whenever it’s asked for.

      That being said, I think this is worth bringing up in a meeting, though it should be business during an existing meeting rather than one called just for this purpose. “I’ve realized I’ve been deviating more from policy than is practical and letting people leave when it’s bad for the workflow. Night-before requests will no longer be granted; requests when projects are due won’t be granted. Please, for your own sake, don’t book tickets for anything before you have approval in email [or other fixed medium] from me.” (I’d actually be inclined to say no texts for vacation at all–planned absences should be in a more fixed format.)

      1. Katie the Fed*

        Oh man, the booking tickets before leave is approved. UGHHH. It always feels like a way to strong-arm/guilt me into approving leave. I’ve made it clear that if you bought tickets without leave being approved, you’re not getting any special consideration. I’ll approve leave based on my normal processes (especially for holidays), not because you bought tickets.

        1. Mallory Janis Ian*

          That’s the policy around here, and it states upfront that tickets purchased before leave is approved may not be reimbursed (for work-related travel) or will not be given consideration (for personal leave). I’ve never seen anyone attempt to abuse the policy, but if strong-arm tactics were someone’s MO, I’d like to see them have their request denied* because I’m cranky like that.

          *not arbitrarily denied just to prove a point, but denied if the leave would not otherwise have been approved for real, workload-related reasons.

      2. Legalchef*

        I agree with this, but then there needs to be a policy for how long requests will be responded to. It’s not fair for someone to have to significantly delay booking (and therefore potentially have to pay a lot more) because the vacation wasn’t approved until 2 weeks after requested.

        1. Paquita*

          At one old job DH and I planned to go on a group tour to Israel in late January early February. Per policy no time off was ever approved until AFTER the beginning of the year. What if someone wanted Jan 2 off? (New Years Day was a holiday). Stupid policy! We paid our money and just hoped for the best.

          1. Anna*

            Yeah, I’m not going to lose good prices because of slow management response time. It’s never been an issue. It goes along with knowing your job.

  4. The IT Manager*

    I think you need to enforce your policy. I totally get allowing the mom off to see her son on his one day of leave; however, why didn’t you stop the guy from leaving early for his reunion? You said the project needed to be done before his departure why didn’t you enforce? I think the obvious answer is you’re not comfortable with potential conflict or uncomfortable conversations. You’ll need to work on that. There seems to be a good chance you’ll have to say no to these people in the moment in the future since your announcement of your policy change hasn’t resulted in a change in the way they request leave.

    I’m shocked too. The only way I would contact my boss after hours for leave the next day is if something urgent came up. I agree if I’m having a good week or a busy week, but my work is done I might request a day within the upcoming week. But so many last minute leave requests seem odd to me.

    1. ZenJen*

      I definitely agree–I would NOT have let the guy leave early. He knew better, and I would have reinforced the conditions of his request right then and said SORRY you didn’t finish what you needed to, and we’re unable to take over your work.
      When my staff take last-minute time off, they KNOW to let me know of any pending work and whether they have already arranged for back-up coverage of it or if it can wait until they’re back in the office OR if I need to find coverage of the work. OP needs to have his/her employees be more active participants in managing their workload coverage.

      1. irritable vowel*

        Right. And then if his response was anything other than, “You’re right, I’m sorry – let me tell my wife we’ll have to wait,” then that becomes a performance issue that you can address in a more formal manner. But because you let him leave, you’ve lost the opportunity for there to be consequences for him.

        1. Dan*

          To be clear, I’m not sure the OP “let” him leave and lost an opportunity for consequences. I mean, OP can tell said employee that he “can’t” leave, but you know what? Said employee can walk straight out the door. OP isn’t allowed to physically restrain him. If he says, “I’m leaving and you can’t stop me.” Which is a true statement.

          There’s no reason OP can’t write him up later or use whatever other consequences she may have in this circumstance.

          1. Ineloquent*

            True, but it’s not like an employer can’t decide that an employee who has done that won’t be coming back. That sort of flagrant disregard for management would be termination worthy imo.

          2. The IT Manager*

            The LW wrote the story as if she was in the room at the time and concluded with I was pretty steamed, because as his boss I thought I had made it very clear that he needed to have this project completed before leaving. It does not sound like she said anything in the moment of his departure to tell him he couldn’t leave with the report only 80% complete. That’s letting him leave without telling him that his vacation was only approved on a condition that was not yet met. If still walked out then that’s a much bigger/firing issue.

            1. Dan*

              I’m stuck on why what she didn’t say in the moment actually matters. The guy’s vacation was approved contingent upon the work being completed before he left. It wasn’t. He knew it. He even not very subtly used his wife as an excuse.

              1. Ask a Manager* Post author

                It can be hard to respond perfectly in the moment to something that takes you off-guard. I agree she should have, but I understand why she didn’t.

                1. teclatrans*

                  I think I understand Dan to be saying that he can’t understand *commentors’ emphasis* on her failure to say something in the momtht, because it doesn’t preclude her calling him on the carpet, writing him up, or etc. afterward.

    2. neverjaunty*

      Yes, this. OP, it’s pretty clear that your reports don’t think you will say no to them, and they’re taking massive advantage of that.

  5. Joseph*

    Honestly, I’d start by denying some of the less important requests. While you don’t necessarily want to get too far in the business of judging requests, some of these are undoubtedly a lot easier to say no to than others.

    I mean, you told your entire team in advance that nobody could take vacation, but you then had an employee ask to skip out half-finished to avoid traffic? Really? I’ll bet you could think of a couple more examples where you could easily have said no without drastically affecting the employee.

    The instant you *actually* deny a vacation and make it stick, your employees will stop doing it. The trick is to find some small items, so they don’t have a long period of active resentment for it.

    1. Newby*

      Yeah. The lack of enforcement is making the message unclear. No letting someone leave early if he had actually finished the work would be uncalled for, but if the work isn’t done it is not unreasonable to expect him to finish it before going on vacation.

    2. Not a Real Giraffe*

      Honestly, I’d start by denying some of the less important requests.

      I don’t agree with this, which sounds like denying requests just for the sake of denying requests and building up a reputation for saying no. If a request truly impacts the workload, and if it’s truly unreasonable, then yes, start denying those requests. But don’t deny a request just so you can be known as someone who doesn’t always say “yes.”

      1. Mallory Janis Ian*

        I agree. I wouldn’t say “no” just for the sake of saying “no”, but a good place to start enforcing some basic standards would be around situations such as the guy who egregiously left early despite not having his work finished. Just hold people to the real, actual work; don’t make up arbitrary standards just to appear like a tough manager.

      2. Joseph*

        The problem is, right now the OP is known as someone who always says “Yes”. And it’s having clear consequences on the functioning of her team – OP has explicitly said she needs to scramble and work late to address these issues.

        Right now, OP’s employees ask with no notice because OP has made it clear through her actions that the policy doesn’t actually exist. As long as OP continues to always say yes, why would they ever change?

        1. Mallory Janis Ian*

          She doesn’t need to say “no” just to prove the point, though; she can wait until the situation is truly “no”-worthy and then enforce a genuine “no”.

        2. Kate M*

          Arbitrary no’s though aren’t going to go over well. If someone asks for the next day off because it’s going to be a slow day and OP says no, then they come in and have very little work to do. That’s definitely going to cause resentment, and it’s going to make them think that a “no” isn’t actually based on workload. So there’s going to be a morale issue that will bleed through to times when a “no” is warranted.

          If you only say no when there’s actually a need to though, then you’re more likely to have employees who understand that you usually do your best to accommodate them, but sometimes you really do legitimately need people there.

          It’s like a parent who yells at their kids all the time. The kids learn to tune it out. But if the parent only raises their voice in the rarest of occasions (like an emergency), then the kid will learn that a raised voice actually means something.

    3. Ife*

      Before starting to deny last minute requests, I think it is important to explicitly tell the employees what you expect, otherwise the employees may feel blindsided if they had been used to requesting days off with little notice in the past. Remind them that your policy is one week’s notice for planned vacation days. If you receive less than one week’s notice, you will try to accommodate the request but it may not be possible due to work flow/coverage needs.

    4. all aboard the anon train*

      I’d be careful about choosing who gets to go on vacation and who doesn’t based on their reasons for wanting a day off. It’s really not up to the OP to decide whose vacation plans are more important or “worthy” or a day off, plus unless I’m misreading your message, it kind of implies that the employees need to start saying, “I want X day off because I’m doing Y” instead of just saying they want a day off.

      1. Florida*

        I think if the employees are following the policy, then it’s not up to OP to decide if the vacation day is worthy. But if they are violating the policy and want an exception, then OP gets to decide if it’s “worthy”. For example, the general consensus seems to be that the son’s military leave is worthy, but leaving the team in a bind so you can miss traffic is not worthy.

        But if people are following the policy, I agree with you that they should not have to justify their reason for wanting a day off. In fact, if people are following the policy, unless there is a specific reason to deny the request (it’s retail and they want Black Friday off), then the default should be to approve it.

        1. fposte*

          I think that’s a good differentiation. Arranging vacation is a right; arranging one against policy is a favor.

        2. Ad Astra*

          I agree. OP doesn’t need to decide who’s got a “worthy” reason for taking time off if they’re following the policy. But it makes a lot of sense for OP to decide which situations are worth making an exception and potentially taking on extra work to accommodate. After all, we would all be pretty horrified if OP had put her foot down and told her employee that she absolutely couldn’t see her son on his one day of leave. So much of a manager’s job is making judgment calls.

          1. Katie the Fed*

            Right – that’s how you end up with a situation like the boss who denied the employee leave for her college graduation.

          2. Vacation Manager OP*

            I feel like this is the point where I’ve gotten myself stuck. I absolutely agree that the reason for taking vacation doesn’t come into play when it’s a request for time off with notice — maybe you are using the time to save orphans, maybe you are using it to pick your toenails — but without notice, the reason seems to come into play more. And I’m in this situation where the significant majority of the vacation requests are without notice, so in effect, I *am* listening to the reason every time (and a lot of the time, the reason is volunteered right in the first sentence of the request, so I know it whether I want to or not).

        3. Katie the Fed*

          Yeah, I denied a request a few weeks ago from someone who wanted to leave early. It would have caused a significant disruption and the workload didn’t really permit it. I WOULD have made a special exception for an emergency – sick dog, sick parent, World Series tickets, whatever – but all he would say was “I just have stuff to do.” Sorry, that’s not enough to make me jump through my butt to accommodate you.

        4. MillersSpring*

          Alison, if the OP explains to her team that the policy will now be enforced, but then she has an enployee make a last-minute request, which the OP denies, what if the employee balks and still wants to take the vacation? What recourse(s) does the OP have…can she have the time classified as unpaid leave? Does she start a PIP or other disciplinary steps?

          1. Ask a Manager* Post author

            That would be pretty serious insubordination. If someone goes on a vacation that you’ve explicitly told them you can’t give them time off for, you’d want very serious consequences. The specifics would depend on the the circumstances. If this was someone who already wasn’t great and had had past issues, I’d seriously consider just firing them over it. If it was someone who was normally good, I’d take more of a “what on earth happened here?” approach when they were back — serious conversation to try to figure out what went wrong, while making it clear that it was a Big Deal that could not happen again.

            1. Not So NewReader*

              Doesn’t that approach abandoning your job? If you are told not to leave then you leave, that can’t be left unchecked. Everyone will be doing that once word goes around.

              1. Dot Warner*

                That’s a good point. Most of the places I’ve worked would consider each day of the “vacation” a no call/no show, and if the person is gone more than 2 days, they no longer have a job.

      2. Jaydee*

        I would focus less on the reasons for the time off than on the work situation. The issue for family reunion guy wasn’t that it was a family reunion or even that he just wanted to leave early to beat traffic. The issue was that there was work that needed to be finished before he left and it wasn’t finished.

        So don’t deny Jane’s last minute request to take Friday off to go camping just because it’s not super-important in your eyes. Deny it if there is some reason that her taking Friday off will cause issues at work (“Sorry Jane, I’d like to be able to say yes, but Fergus already has Friday off and I need you here to run the teapot glazer.”) And if you give conditional approval for leave (“Fergus, you’re welcome to leave early tomorrow as long as the TPS report is finished and in my in-box before you leave.”) enforce those conditions. Fergus doesn’t leave until you have a TPS report from him.

        1. Mallory Janis Ian*

          For most typical time-off requests I agree with this. But something like a son’s one-day military leave or a college graduation are so extenuating that a good manager will grant the time even if it does cause some trouble with the work, so there will still sometimes be judgement calls involved.

          1. Jaydee*

            Oh, I agree with that 100%. But only in the direction you have described. Some requests for time off will be so meritorious that approving them is warranted even if it’s not convenient. But I think if you’re denying a request for time off, the focus has to be on the work impact first. So you can use the reason for time off to approve a request that would otherwise have been denied. But not to deny a request that would otherwise have been approved.

          2. JessaB*

            Yes, but to do that you have to be consistent around the rest of it. There will come a time when an employee is going to be really ticked off (and rightly so,) if they’re suddenly at the last minute held to something that they’ve never been asked to do before. And regrettably (and the OP already knows this,) letting Fergus go before the work was done was a really bad idea. This needs to be nipped ASAP before it gets far worse than it is. And it starts with a talk to Fergus about “I really don’t care why you left, you knew very well that this had to be finished. You do that again and you’re out.” Now if Fergus had left because he was sicking up or something that’s different. But he knew very well that the rule was finish the work.

            After dealing with the issue with Fergus (which I really do agree with everyone who said this is a one on one thing,) you can have a meeting with everyone including Fergus about expectations going forward. You don’t again bring up the particular, specific, issue with Fergus (you’ve dealt with that,) but you make it clear that this kind of thing can’t keep happening.

            Also I think it needs to be discussed that while they are not putting out their co workers, they ARE putting you out. They don’t see that happening, so they may not realise thinking “hey I’m not making new work for Jane and Jo and Fergus so it’s okay,” when it’s really taking an incredible toll on you.

            Once they understand that there are rules, you can of course actually make exceptions to them. But to make an exception (military son,) they need to know there’s a rule they’re actually telling you to waive for them. Also I still think that in 99% of the time a graduation is something you know about in advance. And military parent should have been switching leave (unless the original date was a date they don’t work such as a weekend.)

            And the rule about in advance should be “as soon as you know x, let me know, so I can make decisions about things so we don’t get stuck.”

            It’s not that they have to let you know a week in advance, but geez, if you know for instance in early May that graduation is in late June, why the heck not tell the boss this so it can go on the calendar.

    5. Florida*

      I agree and disagree.

      I would not deny a request just show your employees that you’re the boss. To me, throwing your weight around to prove your the boss is the worst sin a boss can commit,

      However, I would deny a request if it is going to impact the work flow. (You will feel bad about it the first time, but you’ll get used to it. Remember that your priority is the work flow, not your employee’s personal lives.) If you say, “No vacations the first week of August,” then you allow it, you have taught your employees that the vacation policy is merely a suggestion. But if you say, “No vacations the first week of August,” and Johnny wants to take a half-day off so his wife doesn’t have to sit in traffic, then I’d stick to my guns.

      Good luck with it.

      1. LQ*

        I think this is a good point. If my boss denied my leave request because I requested last minute even though I knew all my work was wrapped up and it wouldn’t impact anyone else? I’d be like FINE You want to nickle and dime. We can nickle and dime. If he denied it and said, “Hey CMS coworker and I are both going to be out, we haven’t put it on the shared calendar yet, can you be here?” I’d have no problem with it.

        We need to have someone who can update the monkey dance videos? Sure! Of course.
        I don’t like that you didn’t email me sooner? Why are you treating me like I’m 3?

      2. Joseph*

        Right now, these requests are impacting the work flow severely. Read this paragraph from the OP:
        “The missing piece, maybe, is that even though they are willing to do extra work, it also creates extra work for me, and it can ripple through projects in ways where I am the one working late, rushing, asking other offices to give us extended deadlines, or putting other important tasks aside. It’s causing stress for me. While they can reciprocate to each other, they cannot reciprocate *to me* many of the aspects of my job that get put on hold during times like this. ”
        It’s not OP throwing her weight around just to be The Boss, it’s changing the policy to address issues caused by no-notice absences.

        1. Florida*

          I agree. I don’t think that OP is throwing her weight around. (If anything, she’s doing the opposite.) I was responding to Joseph who suggested that she deny some requests just to show that she can deny them. I’m sorry I wasn’t more clear about that.
          Denying for denying sake is being a jerk. Denying because it is a work issue (as OP describes it) is reasonable.

        2. Kira*

          Agreed. I felt like OP is underestimating the impact on workflow. Maybe OP sees it like “I can workaround Jane’s absence, I’ll just need to reschedule X, prioritize Y and Z and talk with Rob about…” instead of “I’ll need to do quite a bit of working around this absence to make it work, it’s probably not a good idea right now.”

          1. Vacation Manager OP*

            This is an excellent point and I will really think it through. Thank you!

    6. Recent Reader*

      “The instant you *actually* deny a vacation and make it stick, your employees will stop doing it. The trick is to find some small items, so they don’t have a long period of active resentment for it.”

      And then your best employees will jump ship, b/c they understandably want to work for a manager who treats them like adults.

  6. Roscoe*

    It seems, in general, that they don’t see the ripple effects you mention. So that may be a good thing to mention. Not in a “woe is me” type of way, but in a way that lets them see how their absence can affect others. If, in there mind, they think their work is done, and they all cover for each other, it makes complete sense that they don’t see the problem with it. But if it is bigger than that, then let them know.

  7. TotesMaGoats*

    I would be annoyed by the last minute vacation day requests, especially if they were coming late at night. You couldn’t have asked/told the day before when packing up? Sick leave is one thing either for them or a kid/family member. Death in the family, again, not really the issue. It’s the “I’m gonna take the day off” and I’m not gonna tell you till right before because I know you’ll say yes.

    With a small office I would absolutely enforce at least a week’s notice, and probably more, when taking more than a week off. That’s a major workload shift. They don’t seem to get the impact their leave is having on you and office productivity.

    1. Anna*

      It sounds like the last minute at night request was because that’s when the woman realized when her son’s leave was. If you had said no to that, you would be making a bad choice. However, what it shows is that each request needs to be weighed individually based on what is happening in the office and what can be accommodated. Guy who left early should not have been permitted to do that. Woman who got the date wrong on her request and whose work can be shuffled can probably be accommodated.

      1. TotesMaGoats*

        Yeah, I would definitely give the military son person the day off. I got the impression that there were more last minute night before requests for less “emergency” situations.

        1. Vacation Manager OP*

          This is very true, it feels like everything is an emergency when the requests are made. I am getting a lot of “last minute emergency vacation requests” and almost no “hey, I’d like to take some days off next week” requests. Can people have so many emergencies? I have never turned down a vacation request with notice, so I don’t *think* I have set any sort of tone that it is hard to take vacation unless it is an emergency. That is a big part of my frustration — people have a generous number of vacation days, it’s easy to request them in advance, it’s unlikely the request will be turned down in advance … and yet still, it’s all last minute requests.

      2. JessaB*

        Honestly even if we had to scramble, I’d have approved that military mom. I hate to be a downer, but geez, given that we’re boots on the ground in hostile countries, it’s possible that she may never see him again. I’d freak out and feel like world’s hugest jerk, worst boss ever in the universe, if gods forbid something happened to that son and I said she had to work on the last day she could have seen him.

        Dude that wanted to leave early because of traffic? Nope, nope, nopity nope. Not going there. “You promised me you’d finish this, you’re not finished, sorry. You stay.”

  8. BananaPants*

    For the employee whose child was on military leave, bear in mind that she may have said she got the date wrong when in fact the date had changed due to circumstances beyond the adult child’s control. Frankly, I’m impressed that the employee actually told you the real reason rather than just calling out sick (assuming she had paid sick time). If the kid was in boot camp or technical school he could have been “recycled” due to injury or illness, graduating later than expected. His deployment or move date could have been moved up, forcing him to visit NOW rather later if he wants to actually see family before deploying or PCSing. My brother’s active duty military and I need more than one hand to count the times that his travel plans have had to be shuffled on short notice because the boat is suddenly going out to sea 2 weeks early or there’s a huge inspection scheduled or whatever. Having some compassion for the parent and allowing a short-notice vacation day in that situation is commendable.

    But for the guy who got approval to leave early on the condition that the project got done? As Alison says, I would have told the guy that the agreement was that he could leave when the job was done, and it didn’t look like that would mean leaving early since the team was only 80% of the way there.

    1. Chinook*

      ” My brother’s active duty military and I need more than one hand to count the times that his travel plans have had to be shuffled on short notice because…”

      As the one who had to reschedule getting married twice (and just eloped the second time) because the military changed their plans with future DH, I agree. This is not a case of “family is more important” but more “the person I have plans with is on a tight schedule that is dictated by powers beyond his, or any one person’s, control.” Add to that the fact that the odds are against them seeing that person any time soon (for the same reason) and this is where compassion comes in.

  9. coffeepowerrdd*

    I think that this decision may hinge on your employees’ current perceptions of how important their attendance is at work, versus having the job completed. I am alarmed that your employee left early after promising to stay just to avoid some traffic, “due to his wife”; that is one of the lames excuses I’ve ever heard and if I were in your position I would have said, “actually you can’t leave until this is finished”, right on the spot.

    I think your employees think that they can just come and go from work at any time, based on their behavior, and it’s getting egregious enough that it’s affecting productivity. It wouldn’t matter to me if they could come and go and the work is done. Because when the work is done, the day is done (basically, right?). But that’s not what’s happening here. What’s happening is your employees are walking away from their responsibilities to tend to their personal lives, at your expense and the expense of others, which isn’t okay. I usually offer a solution of how to fix this, but I think Alison and the other commenters will provide something for you.

    1. addlady*

      I am totally going to pin all my bad decisions on my spouse/friends/relatives from now on. I’m sure it will go over GREAT.

    2. Mallory Janis Ian*

      That’s what irritated me about that guy’s leaving early: not just that he didn’t finish his work as he had committed to do, but that he seemed to think a “wife trumps boss” statement was a perfectly valid departure-enabling device.

      1. Katie F*

        To me, that ‘sounded’ like the employee KNEW he shouldn’t leave and was trying to shift responsibility for him choosing to ignore/disrespect the boss onto someone else who wasn’t there to be disciplined. “Oh, yeah, it’s not ME that wants to leave early, really, it’s totes my WIFE who, golly gee, isn’t here for you to ask!”

        That was honestly the most disrespectful part to me – not that he still tried/left early, but that he pinned it on someone else to make the boss feel bad about pushing back on it. That’s… immature.

        1. lollo*

          But then we never know if he had a ‘Hitler wife’ that was verbally assaulting him that he had to leave early to beat traffic or else she’d strap him to the car roof for the drive… and even then it is only appropriate to ask, not inform. Informing only works to leave for medical reasons.

          1. Rat in the Sugar*

            It’s still not appropriate to ask, imo. Employee knew that OP needed the project done before he left and it wasn’t done yet. His relationship with his wife is his own to manage, regardless of how closely she may resemble dictators past.

        2. addlady*

          It also seems to me to be a jerky thing to do to your relatives. How would you feel if you knew that people were blaming you for their decisions behind your back? “Oh, I’m sorry I can’t have fun with you, you can totally blame my manager for that.”

        3. Florida*

          This. It’s a manipulative tactic that he has probably used forever. When he is talking to his wife, he probably blames stuff on his boss.

          1. Dynamic Beige*

            Yeah. Same thing when he can’t hang out with the guys. Some people find it easier to blame someone else than take responsibility for their own choices. And on the other hand, if a woman said she had to leave early because her husband said so, everyone would immediately jump to a place of “you’re not his property”/”are you safe”/something along those lines.

          2. Katie F*

            Yeah, exactly. I imagine if OP had held him to the “don’t leave until the work is done”, he would have been on the phone to his wife surreptitiously talking about Just How Awful His Boss Is instead of admitting “maybe I should have put in the extra work to get this project done early or asked for this day off entirely a month in advance.”

            He sounds EXACTLY like those people for whom everything is always someone else’s fault/responsibility.

    3. Vacation Manager OP*

      Thanks for your comments! I definitely wish I had been ON IT at the moment to give that response on the spot. I had replied to a comment above that it was one of those things where it was happening before I really put all the pieces together.

      I also wanted to let folks know that I do, overall, think he is a good employee. I get that in a short account of one specific incident, I created an impression that he is a terrible employee who intentionally blamed things on his wife so that he could kip out of work early. For me, even that very day, it was more indicative of a genuine, also extremely naive, assumption that our work environment is awesomely flexible. I like to think we’re flexible, but not to that extent.

  10. WellRed*

    I emailed my boss that I was taking a vacation day today at 8 am. So grateful to work in a place like that, even if they don’t let us roll unused time over.

    1. ZenJen*

      yeah, it’s nice to have that flexibility IF you’re not sticking your boss/coworkers with your work because you felt like taking a day off. it’s not about having the day off, it’s about how to manage your workload so that these last-minute absences don’t impact the general workflow AND sometimes it’s about planning ahead instead of doing a last-minute call-out.

    2. Anonymous Educator*

      Would you do that if you knew today was a heavy day at work, and they needed you in the office? I doubt it. It’s not really just about whether the request is last-minute or not.

      1. Ask a Manager* Post author

        Right, but I think the point is that the fact of it being last-minute isn’t inherently problematic. The only relevant factor is the impact on the work. If there’s no impact/not much impact, then it shouldn’t matter if there was a week’s notice or not.

        1. Anonymous Educator*

          I don’t think it’s inherently problematic, but I do think it’s a factor. The greater factor is the impact on work, but the two are also usually (not always) related. With a heads-up (not a last-minute request), it’s easier for a manager to plan ahead for workload redistribution.

          1. Anonymous Educator*

            In other words, when an employee makes a last-minute request, she’s essentially make an impact-on-work assessment for her manager, since she’s putting her manager in the place of either denying or approving the request. Depending on your industry and role in it, most of the time, having a heads-up gives the manager a chance to make a better impact-on-work assessment. “Oh, employee A is taking Thursday and Friday off that week. Perhaps I can have employee B work on that project then, and then give the other project to employee A, so she can cover the days that employee B is out.”

            1. Kate M*

              But sometimes workload doesn’t need to be redistributed. I work in lobbying – right now Congress is in recess for the next six weeks. Which means there is not a lot on the Hill that our clients need to be updated about, especially on Fridays. If I finish my big projects on Thursdays or I have things that can wait until the next week, it’s not a bad thing to say I’m taking Friday off. In that case there’s nothing to reshuffle to anyone else. I know my workload, so my manager doesn’t even have to think about it.

              So it’s not always a factor. If you work in an industry where it matters, you know it. But if you work in an industry that’s more flexible, you shouldn’t be rigid just for the sake of it.

              1. Anonymous Educator*

                Sure. There can be exceptions. As I said before, it depends on your industry and your role in it.

              2. JessaB*

                Yes but KateM you’re actually making that assessment and you know that because you know your job you’re making a reasonable assessment and if for some reason you missed something and your boss said “Um, we just found out that we’re going to have a meeting with $$BIGBUCKS client, even though Congress is out,” I bet you’d be okay with working it.

                I get the opinion that the OP’s employees aren’t. None of them seem to be taking workload into account. Especially the change in workload for the OP because the OP hasn’t let their employees KNOW that there is impact. If you shield them from the impact, you can’t then get annoyed that they didn’t account for it.

                And in most cases requests should not be last last minute. Asking on Monday to have Wednesday eh, could be horrible depending on the company. Asking Monday to have Tuesday has impact if only because the boss has to scramble, a la minute, to figure out whether or not they can approve that. The understanding that if it’s not a critical reason that if you ask on Monday for Tuesday you can be told no, is something that OP’s employees seem to need to learn.

  11. Anonymous Educator*

    A conversation afterwards is certainly a good starting point (“Next time, you have to give me more of a heads-up”), but most people learn from actual consequences. Take it from a former classroom teacher, you can tell kids all you want “If you turn in your paper late, you will be marked down a grade,” but unless you actually mark it down when it’s turned in late, no kid will listen to you. Same deal with adults. It seems the take-home message they’re getting is “My manager is chill; I can just ask for time off whenever.” The take-home message should really be “Work at work needs to get done, and I need my manager’s approval to take time off.”

    Honestly, I just asked my boss for a day off (one vacation day) recently, and I asked three weeks in advance. It wasn’t that difficult to do, and my boss approved it. Certainly, if some emergency came up, my boss would understand getting less notice, but for most things (reunions, weddings, vacations out of town), you will know more than a week in advance that you’re going, so there’s no excuse to not give your boss a heads-up so she can plan coverage.

    It is not an unreasonable expectation to get at least one week’s notice for vacation time.

    1. neverjaunty*

      Yep. When the words coming out of your mouth don’t match your actions, people notice. The message these employees are receiving, loud and clear, is that they can take time off whenever they feel like it, with no consequences if that means ditching work.

  12. Ad Astra*

    Oh man, this whole post — both the OP’s thought process and Alison’s advice — is just oozing with reasonableness. I can’t take it.

    1. March*

      It’s amazing how much this contrasts with “I wouldn’t let my best employee have time off for her graduation”. Now here’s a case where the employee’s being unprofessional – “My wife wants me to leave early to beat traffic”. Can’t get over it.

    2. Jamie*

      “Oozing with reasonableness is exactly what I was thinking…but you worded it better.

      But I’d also take a look at the policy itself too. In general, I’m a fan of adults managing their own time off, and I wouldn’t love a policy that required a week’s notice for just a single day off. Adults should be able to look at their workloads and think, “You know, if I push to get everything done by Thursday, I could take Friday off without it impacting anyone else” and then do that. And I’d be annoyed as hell if I knew I could manage my workload to make that go seamlessly, and yet was still told no because I didn’t request it a full week ahead of time. If it doesn’t impact anyone but me, it’s infantilizing.

      And so much this. And to the people who set and fiercely police this kind of policy for the sole reason of making it really hard for your employees to interview…ever…you suck.

      OP isn’t doing that…just saying I’ve heard it happens.

  13. Mimmy*

    See, now this is why I’d make a horrible manager: With the guy that left to purportedly avoid traffic when the project wasn’t 100% complete, I would’ve let him so as not to get him in trouble with his wife :P

    In all seriousness, based on the way it was described, it sounds like he likely knew he was breaking a commitment, clearly taking advantage of the flexibility. I’m all for flexibility when it comes to time off but the OP definitely needs to be firm about the consequences of these employees’ behavior. I would recommend having a meeting with the team and explain that, while you have been flexible, it is starting to impact productivity. Then, if people continue to not heed your directives, meet with them privately and “in the moment” if possible.

  14. Kiki*

    Didn’t we have a letter a few weeks ago about the good employee who quit on the spot when her very reasonable request for time off was denied? That might happen here, as it seems like, at least from the employee’s point of view, this is a change to the office culture. I can see where a good employee might think this is a game changer and opt for a new employer. Not that requests in advance are unreasonable at all.

    1. neverjaunty*

      This really isn’t like the previous letter at all. Promising to finish a project, then not finishing it and leaving for convenience’s sake is not a “very reasonable request”.

    2. Anonymous Educator*

      The two aren’t comparable in any way at all. That other letter was an employee who’d never taken a sick or vacation day in six years, covered other people’s shifts, already knew well in advance that she wouldn’t have to work the day of her graduation and then was suddenly sprung with “You have to find coverage and work on this day you wouldn’t ordinarily work,” and then she couldn’t find co-workers to cover.

    3. OhNo*

      It might be a change to office culture, but it’s not a change to policy, which is why I think this is a very different situation. I mean, imagine if the OP did enforce the policy, and Alison got a letter from one of the employees: “In my office we’re supposed to give one week of notice for vacation, but my boss has never stuck firm on that requirement before. Now she is going to. She even turned down my last-minute request last week! Should I quit?”

      I think most of us would give some pretty heavy side-eye to that person for complaining about actually having to actually follow a policy that they new about before they accepted the job.

    4. Kiki*

      I do get the difference everyone, but thank you. Just pointing out that those most affected might not see it that way. As a manager, I like to look at things from every angle.

      1. Anonymous Educator*

        Just pointing out that those most affected might not see it that way.

        Sure, they’ll grumble about it, but the manager wouldn’t be being unreasonable, so no one here would care for the grumbling. As OhNo stated, disinterested parties (i.e., readers here) would give serious side-eye to complaining about actually having to follow reasonable expectations.

  15. Lily in NYC*

    I can understand this policy for a “true” vacation of more than one day, but I not if it’s expected to give that much notice when someone wants one day off. Shit happens. I live alone so I’m the only person who can answer the door if I have a last-minute emergency that needs a plumber, etc. How am I supposed to give a week’s notice for that?

    1. Lily in NYC*

      Adding to my comment – if the role of everyone on your team relates to crisis management, then it makes a lot of sense to have this type of policy.

    2. animaniactoo*

      That counts as an emergency, not a pre-planned event which is the kind of thing that the OP is talking about.

    3. Anonymous Educator*

      If I’m understanding the letter correctly, I think it’s less about the actual vacation day and more about the attitude of not caring about whether work gets done or not. I promise you if I had a busy day at work ahead and a plumbing emergency, I would do everything in my power to get coverage and/or work remotely and go back into work as soon as the emergency was taken care of. I’m not getting that vibe from this letter. “[H]is wife made it very clear that they needed to avoid rush hour traffic for their drive to the reunion.” Nope.

    4. doreen*

      You can’t – and I don’t think anyone expects you to. Certainly not anyone reasonable.But the problem the OP has is similar to one that I’ve encountered. The official policy was that time off had to be requested in advance except in emergencies. In advance, not a week in advance so that asking for Wednesday off at 4 pm on Tuesday was within policy. And of course, workload was a supposed to be a factor in approving time off. But my predecessor (s) didn’t follow either policy , so it wasn’t terribly uncommon when I first got there for multiple people to call in the morning asking for the day off because 1) It was their mother’s birthday 2) It was their own birthday 3) Their apartment was being painted 4)They had to be in court for a personal matter and so on. All things that should have been known about in advance. It’s one thing to run short-staffed because someone is sick , or had a plumbing emergency or their car broke down or their kid in the military got unexpected leave or even that they got the date of the leave mixed up. It’s another thing entirely to run short-staffed because someone couldn’t bother to plan ahead and ask for their own birthday off. And it wasn’t a matter of a couple of problem employees – I would say that at least 75% of the employees made it a habit to request single days the day-of. This is the reason why some places end up with unscheduled absence policies – it’s difficult to deny someone the day off when they have to be in court or the landlord is sending painters so the problem didn’t actually get solved until my employer put an unscheduled absence policy into effect. (which actually was not a bad policy- starting after the 8th unscheduled absence in 12 months, a manager had to look at your attendance and decide whether some sort of action should be taken. It didn’t actually require any action to be taken , only that a manager make a decision and document the reason , so a 20 year employee with a good attendance record who hit a bad patch could be treated differently than a six month employee with the same 8 unscheduled absences)

  16. animaniactoo*

    OP – worth noting. How wrong did the military mom get the date wrong? Because if she got it wrong by less than a week, she was still screwing up the notification/request.

  17. LQ*

    Do your staff have a good idea of what their workload is? That sounds like a stupid question but I kind of wonder if they do. If you can give them more understanding of what the impact is and what it takes I think that might make a big difference.

    Do they know when their coworkers are out? We have a sort of shared calendar system so I know who is out of the office for all or part of the day and it is super helpful to know that I can’ t go to Jane I need to ask Wakeen instead. But it also lets me know that my CMS coworker is out and is there something else happening so that one of us should be in the office? If so then I won’t even request time. I can make that decision because I know who else is out and what my workload is and what the impact will be.
    I’m not entirely sure if you have things that can be passed from one to another person but if they can, if it can be managed a bit like that it might be good to empower your staff a bit more to understand the impact of their time off. They might start making better decisions without having to be punitive about it.

    1. Meg Murry*

      Yes, I wondered how the communication was between the other 3 team members and whether there was any kind of shared calendar? Because I feel like there is a big difference between Jane asking to take a random day off knowing there is a deadline tomorrow and Joe is already on vacation, and Jane asking for a day off because as far as she knows tomorrow is a regular fully staffed day and there are no pressing deadlines. If her staff could check a group calendar first and see what deadlines are coming up and who is already out, they might know that they shouldn’t ask for days with big deadlines.

      Again, with communication and the person that left early – you told him that he could leave early as long as the GROUP project was complete. But did he have his own part of the project, or was it a complete team effort, and did the rest of the team know that? If Joe wants to leave at 2 pm, and Project XYZ is due today – well, I’m going to assume that the deadline is close of business, not 2 pm – and I could see Joe’s frustration if he is being expected to wait until the entire group finished if he put in extra effort to get his parts done, while the group is frustrated that no one told them that Joe was leaving at 2 pm. If the whole group is aware that the target is 2 pm (or possibly that the composing of the project needs to be done by 2 pm, and then Jane and Bob and OP will finish up the last of the spell checking and formatting) and Joe is doing parts A, B and C, while Jane does E and F, etc – that’s different, that’s pulling toward a team goal.

      1. Library Director*

        Shared calendars don’t always fix the problem. We have a shared calendar accessible on the web that shows programs that obligate employees. This means they cannot be at fixed staff points. I still had people text or email me saying they wanted the day off because all they would do is count the number of people and say, “Oh, everyone’s there.” Worse was that more than one person would do this. Texts and emails were removed from the request process (it’s not the normal process anyway). Call me and we’ll talk. If we can work the schedule we will. But, Busy Bob may be scheduled to be in his office all day because of big state report on the teapot statistics with a short deadline.

    2. Dynamic Beige*

      My question about communication is: would it have been reasonable for OP to check in with “Wakeen” earlier or would that have been too parent-y?

      I mean, would it have been reasonable and/or a good idea for OP to send Wakeen an e-mail on say, Wednesday, requesting a status update on where he was at with meeting his deadline? As I am not a manager (and don’t play one on TV) and work in a very deadline driven field, I could see if I were in that position asking “just wanted to see where you’re at with the Spout Report as I know you are planning on leaving early on Friday.” If he’s been willing to stay late in the past, shouldn’t that have been a kick-in-the-pants of “Oh yeah, I’d better make sure that’s done” kind of thing? Or is that too micro-managey?

  18. Carissa*

    I agree that you should have a meeting with your employees and talk to them about the policy. If it’s a true mistake- like the employee whose son was on military leave- you can approve it. But the guy who used his wife as an excuse to leave, no, he should have not have left.

    I think they are taking advantage of you. You are going to have to start denying request when they do not follow the policy. In a perfect world, adults can manage their own schedules but we aren’t living in a perfect world. They know you are going to say yes, even if they don’t follow they policy, so they don’t follow the policy. Sure, there will be an occasional emergency that can’t be approved in advance, but otherwise, you need to flex your polite manager muscles and deny request that are not submitted in a timely manner.

  19. Menacia*

    I wanted to make a comment regarding OP being out of the office handling issues elsewhere. The way for your employees to not feel like you are off in the ether doing who knows what would be to send them a quick email explaining where you are, what you are doing, and how to contact you in case of an emergency. That way they will know you are in fact working, and that you respect them enough to let them know what’s going on. If my manager disappeared without any kind of email, that would be very odd behavior for her and we’d start to get worried something happened to her. Communication is great but only when you do it effectively.

    1. Miss Nomer*

      Eh, my managers are out a lot and I’d think it was weird if they did email me. When I first started they explained that they would be out periodically doing x, y, or z and to email with questions. Now, if the OP is rarely out, it might be a good idea to send an email each time. Otherwise, I would have the big picture conversation and then only notify if I wouldn’t be reachable for some period of time.

      1. Victoria Nonprofit (USA)*

        Agreed. It’s pretty normal for people, maybe especially managers, to be in and out of meetings, on- and off-site. It would be weird if my manager sent me updates about his movements.

  20. Ineloquent*

    Wife + traffic is an incredibly weak sauce excuse to be absent from work. I suddenly want to know the worst absentee excuse every one else has run across. For me, it’s the no call no show who, when she finally talked to her manager, explained that she had a bee’s nest on her front porch so she couldn’t get to work… Which also apparently affected her ability to use the back door and/or call to let us know she’d be out. Somehow she remained with us for several more months.

    1. animaniactoo*

      I once completely missed that it was Monday. I lounged around all day thinking it was Sunday, chores and reading, right up until I turned on the tv to watch something that came on Sunday nights, and Monday programming was on instead. That was about 15 or 16 years ago. I probably would have been out the door if they didn’t have prior experience with me (they were my clients when I worked for a different company).

      1. CMT*

        Ha! That one is pretty funny. Nobody called to see where you were?? In my office, we’d start worrying you were dead in a ditch somewhere.

    2. EvilQueenRegina*

      For me it was the broken foot that miraculously recovered after only a week. Said employee returned without a limp, then when our manager was at a meeting in an office in the next street and her car was blocking in someone who needed to leave for an appointment, she managed to RUN to that office to fetch her! This was done in front of an employee who had complications with a genuine foot injury.

        1. JessaB*

          I dunno, I guess the only possible thing to do is ask for a medical note, but then I guess that depends on what you want the consequences to be. It depends on whether or not actually addressing the issue is something you want/need to do. Personally I’d be ticked to have been lied to, if I was. Despite how it looks, you’d be surprised what can happen with people. I broke a toe and limped around for three days with the top front cut out of my shoe, but once the swelling went down I was okay even if it wasn’t fully set yet. So I dunno. I don’t know enough about what the employee said was wrong with them to tell if coming back without a limp after a week is good or bad or if they’re the kind of person who is dumb enough to run when they shouldn’t have and later paid the price with ice packs and anti inflammatories.

          I suppose what you do about it depends on what you want the result to be.

    3. Miss Nomer*

      When I was a tutor in college, one of the other tutors told us he couldn’t make it because he was in the middle of something on League of Legends and his team “would suffer greatly” were he to leave.

      1. LizB*

        Holy moly. That is just hilarious. I have lots of friends that play, so I’m very accustomed to the unpredictable lengths of League games, but all my friends know not to start a game within an hour of something important unless they’re willing to ditch their team when they need to leave. Yikes.

      2. Mallory Janis Ian*

        “Suffer greatly . . . ” ahaha! — I can imagine the wailing and gnashing of teeth.

    4. Oryx*

      I wouldn’t say it’s the “worst” but I had a co-worker who didn’t show up and when our manager called, the employee’s mom answered and said “Oh, she moved to California over the weekend.”

      1. Mallory Janis Ian*

        I had an interviewee do something similar last week. The committee and I were all sitting there at interview time, and the candidate was ten minutes late to a 25-minute meeting. I finally called her, and she said, “Oh! I meant to tell you. I accepted another job.”

    5. LizB*

      I had a coworker who was often very late for meetings, especially after lunch… turns out she thought it was appropriate to take naps in an unused room whenever she felt the need to because sometimes she was so tired she just couldn’t face [work task]. She was neither fired nor disciplined. (That workplace was a disaster.)

      1. animaniactoo*

        Geez. We’ve cracked jokes about going upstairs to take a nap on one of the beds in the showroom, but to my knowledge no one has ever actually done it!

    6. Anonsie*

      The broken foot story above reminded me of a friend-of-a-friend who was hanging out with us in our city, and decided to stay an extra day to spend more time with her friend. Since the next day was a Monday, she decided to call in sick… not with a cold, or anything else that could clear up in one day, but poison ivy. When my friend pointed out that poison ivy rashes usually last 1-2 weeks, and sometimes up to a month, and that there was no way she could just stroll into work the next day claiming she was cured without raising suspicions, the friend-of-a-friend panicked. The last I saw of her, she was driving off into the woods to find some poison ivy.

        1. Anonsie*

          Ha, no, luckily. I still don’t know how her work responded when she showed up rashless. (Or maybe she just decided to call out sick for the next week?)

      1. Mimmy*

        LMAO!! As someone who’s had several suspected poison ivy reactions that would last for weeks, I can tell you that this guy would have been VERY sorry if he truly got poison ivy. Most. miserable. thing. ever.

    7. fposte*

      I was a receptionist at a city branch of an insurance company when they announced the branch was closing. Higher-ups formed their spinoff business while still collecting a paycheck from the lame duck company, and when an appointment was missed I had to tell the receptionist at that new business that it was her boss’s real job calling.

    8. Risa*

      I actually had an employee whose sister died twice. The first time, supposedly they figured out it really wasn’t his sister when they went to the morgue to ID the body. The second time it occurred was less than a year after the first incident. To this day, I’m not even sure he actually had a sister.

    9. Kelly L.*

      Probably told this one before. Pre-cell phones; he’d probably get away with it now.

      College. On-campus burger joint. Employee wasn’t a student, but his girlfriend was. He called from his girlfriend’s dorm room to say that he was stuck in a city two hours away and couldn’t make it to work. Except on-campus numbers identified themselves to other on-campus numbers in the voicemail system.

    10. Anon For This*

      We just went through this with a new employee who had to take off a day in his second week because there was a mouse in his apartment and his partner (who also works for us) is so afraid of them he needed to stay home with her. Regardless of whether or not it’s true I would have honestly gone with “a pipe broke” or something that doesn’t sound quite so high drama.

      This employee followed that up with springing a week of vacation on us (again within his first 4-6 weeks of employment) and then tried to give us a floating return date – as in, “I’ll try to be back on Monday but if I get back late on Sunday it might be Tuesday.” He also spun the whole thing as something he had to do for his partner while sidestepping why he couldn’t have given a heads up when he started (which would have not been an issue, we have that come up all the time.)

      This kid is generally good at his work but those things left a really bad taste in my mouth (and I’m not even his direct manager.) He also took people here having semi-flexible schedules to mean he could start being the first person in and the last person out immediately, even though I questioned how valuable it is for a new employee to basically be here an hour before anyone else shows up. Ultimately I think we’re getting played, but his manager won’t put his foot down and it’s kind of the tradeoff you get when you try to be flexible – someone’s eventually going to take advantage of it.

    11. Paquita*

      At an old job we were already going to be short staffed one day. Person A, with a very good reason, was told they could not be off because too many people were out. Person B was let off because ” her boyfriend was coming in that evening from a two week trip and she needed the entire afternoon to ‘prepare’ to greet him. ” This is the same girl who got engaged at least three time then broke it off during the year I worked in that department. She had a collection of rings!

    12. CarrieUK*

      I had someone not show up for work on Monday, finally phoning midday on Tuesday to tell me that her boyfriend had taken her to Paris for the weekend and they had just gotten back and she’d be back in on Wednesday because she was “tired” from her impromptu holiday…

    13. W.Irving*

      Not an excuse, but: a former colleague in a different department took a short medical leave and then just disappeared. Her manager was worried sick because he couldn’t get in contact with her for weeks – he even tried her emergency contact to no avail. Finally, about a month after she was supposed to return, one of her (former) coworkers stalked her on social media and saw her alive, well, and living it up like she was on perpetual vacation.

  21. Victoria Nonprofit (USA)*

    I’ve told this story here before, but I once had an intern no call/no show on the first day of the Arab Spring protests in Egypt. When called him to check in he said that “as a political science major” he felt that it was more important for him to watch the news that day than come to work.

    Readers who heard this story before will probably remember the best part: his manager was Egyptian (and at work, although she did spend much of the day fielding calls from family and on the phone with reporters looking for a local angle on the story).

    1. Katie the Fed*

      Still one of my favorites.

      Of course I was up until 2am on Saturday morning breathlessly watching the Turkey coverage. :)

  22. Jill*

    As I read the letter, it sounded to me like OP was merely looking at whether the rationale behind the request (son home on leave, wanting to beat traffic) was “reasonable” and then using that as a barometer for whether to give permission.

    OP, you decision shouldn’t be based on whether the reason for the request sounds good. It should be based on the extent to which the employee being absent will negatively impact the office. Low impact, you say yes to the leave. High impact, you MUST SAY NO.

    Those times where you say yes even when the impact on the office will be high, should be for very, very extraordinary reasons.

    1. JessaB*

      The problem with this is that there’s an extra step in there where reasonable does factor in. Sometimes the reason makes it worth bending over backwards to make an exception for a good employee. Unless military mom is a total flake all the time and constantly misses deadlines, takes advantage, there’s zero way I’d turn that down (see my response above.)

      1. Anonymous Educator*

        I would say that’s covered under Jill’s Those times where you say yes even when the impact on the office will be high, should be for very, very extraordinary reasons..

  23. Elder Dog*

    OP, it sounds as if your employees are taking you by surprise, and you are saying yes in the moment, without having the time to think about it or check what other work/deadlines and so on will be affected.
    The thing that worked for me was “I’ll check and see if that’s possible and get back to you in and hour/day/week.”
    Then check and if you can you can, but if you can’t, sorry. The point is not to agree or disagree in the moment.
    That will start teaching people not to wait till the last moment, and let them know if they give you a chance, you’ll try to work things out for them.

    But absolutely, if someone has been told he can’t leave till his project is done, say something, in the moment if you can, and certainly afterward as well.

    1. Anonymous Educator*

      I agree that’s a good approach, but until the OP starts telling people last-minute requests should be the exception rather than the rule and then actually enforcing it, it will be difficult to actually have enough time to consider and get back to the employee.

    2. Vacation Manager OP*

      This is an terrific idea, and I’m going to add in a “let me get back to you” step right away. And I think even if a request comes in via text at 9 pm the day prior, I don’t think someone would complain if I had to get back to them at 10 PM with an answer. The whole issue of “in the moment” is something that became clear to me when reading and considering everyone’s comments — I felt caught off guard in the moment when the staff member left the office, too. Taking back the time to say “okay, let me look into this and I will get back to you” seems like a very obvious thing I can start doing immediately. Let’s hope I remember that the next time there is an “in the moment” situation.

  24. Looby*

    I wish my boss would start saying no to last minute days off. I’m Person 3 in a 3 person team. If 1 or 2 are away, I get pulled from my own duties to take care of theirs because they have a higher priority. I don’t mind the short notice when they’re sick, but telling – not asking – the boss that you’re taking Thursday off before the Easter long weekend, on the Monday afternoon is not okay to me. Or is asking for Friday off on Thursday morning.

    No one does my work when I’m not there, it sits and waits for me to get back. And even when I am there, but acting as someone else, I’m still expected to get most of my work done too. It’s his first management role so I try to cut him some slack, but he really sucks at it.

    1. YOLO*

      So much *this*! My last job was in a place that had very liberal leave policy and treated everyone like adults. Except that managers didn’t feel the need to manage day-of vacation requests, so long as their needs were met. Which meant that my two colleagues would decide not to come in (sometimes on the same day) and their managers would just come to me to get the work done. That I had to delay meetings because I needed to get their input on something was “my work”, not “their work”, so didn’t influence their decision to take a day off. And since it only impacted my work, they didn’t care.

      Literally the only time we would have staff meetings was when I had a vacation coming up – even if it was only 2 days – so that they could get briefed on “all the work they needed to do to cover me”, whereas I just had to pick up and go with their projects because they were in and out with so little notice. There are sooo many reasons I came to hate that job, and poor management really was at the base of all of it.

  25. Narise*

    You are getting to caught up on why someone needs a day off. When you start weighing requests you set yourself up for complaints of favoritism or discrimination. Have a meeting with all three and state that vacation days need to be requested in advance during normal work hours-take after hours requests off the table.

    The employee needs to provide a recommendation of how things will get done while their gone for your approval. Let them know that while you’ve tried to be accommodating they have gotten lax in following basic professional curtesy and the work has to be done so going forward they need to plan their vacations in advance.

  26. stevenz*

    You don’t need a new policy, maybe just an explanation of the reality of asking for time off. Just put in writing more or less what Alison suggests and distribute it – a paper copy – at a staff meeting and ask if anything needs to be clarified. They can’t then say they didn’t know.

  27. nofelix*

    I’d appreciate some advice if anyone sees this – I’m often in the ‘family reunion’ employee’s position: I’ll let my boss know in advance that I need to leave promptly at the end of the day for an appointment, yet when things don’t get finished he still expects me to stay even when it’s arguably his fault.

    Recently this came to a head because I had to leave for a flight at the end of the day. At 6pm he gave me an extra few hours worth of tasks and things got heated because I had to insist on leaving since my original tasks were all done. I know my boss most likely worked till past midnight after that, which I feel bad about but also surely it was his fault for not planning out what had to be done. At least in that instance it was clear-cut that I had finished the original tasks; often he instigates surprise last minute redesigns that stop me completing things. I’m never quite sure how to handle these.

    1. KellyK*

      Well, to start off with, make sure you’re doing everything you can reasonably do to get things done on time. Give your boss plenty of notice, pick days when things aren’t busy (as much as possible), get help from coworkers, and/or come in early if you know you need to leave early or exactly on time. Also, if you know he has a history of giving you last-minute tasks, check in with him earlier in the day to see if there’s anything else. Ideally, you wouldn’t have a flight scheduled when there’s a major deadline at work that requires your boss to work until midnight to finish it. Is that something you knew about when you made those plans, or something that came up later?

      If you’ve done everything you can do to make sure the work gets done, and you have a firm commitment that your boss okayed previously, I think it’s okay to leave when you need to leave in order to make an appointment or a flight.

      The other thing I would do is talk to him about it, both so he knows it’s a problem and to ask if there’s anything you can be doing differently. There may not be. He may just be disorganized and dumping stuff on you at the last minute. And if that’s the case, it’s an excellent reason to look for another job.

      1. nofelix*

        Thanks for your advice Kelly. I do try and sort all these things out ahead of time, yes. There is a confounding problem where he always thinks things can be done in half the time they reasonably take, so the more organisation I do the worse the problem becomes. I hate this because it means there’s always a strong incentive for me to allow the uncertainty to continue. +10% last minute tasks are more feasible than +100% planned tasks.

      2. nofelix*

        And yes, he approves all my leave months in advance, then only lets me know the deadlines to add pressure when it looks like they’re in danger of being missed. And since he underestimates everything, by the time he’s noticed a deadline is in danger most likely we are well beyond being able to meet it.

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