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Ask a Manager: I Didn't Expect My Employee To Take So Much Time Off...

...After a Family Death.

My only direct report, Jessy, recently had an unexpected death in her spouse’s family. This has taken a huge toll on both of them, especially due to its sudden nature.

Jessy let me know a couple of days after the passing. I checked her PTO balances (which are generous in our company), let her know how much time she could take, and encouraged her to take the time she needed. I expected this would be two or three days at the most.

Instead, Jessy was off three days last week and three and a half this week. This has really put me in a bind and left me with a lot of extra work that I hadn’t planned on. In addition to a normal heavy workload, we have several special projects happening. There was no one else who could step in, and one contractor we reached out to never responded, so it’s been a lot of 12-hour days and lost weekend time for me.

I want to be compassionate and understanding, but I can’t help feeling that the time Jessy is taking off is … excessive. She submitted her PTO requests a day or two at a time, so it’s been difficult for me to gauge her availability. Maybe that’s a lesson for me for next time — I’m a first-time manager and I’ve never encountered something like this, so I’m just trying to learn.

I’m hopeful that we can start getting back into a normal rhythm next week, but this has shaken my confidence in Jessy’s reliability and commitment. Does that sound unfair to you? I just get a bad sense that she’s spiraling and I’m not sure what to expect when she (hopefully) gets back into a regular schedule. Jessy has done good work and has been reliable in the year she’s been with us. I’m just not sure how to convey that her absences have hurt us, we’re all sympathetic to the situation and the job needs are the same as before without coming off as completely callous.

Yes, you’re being unfair. You told her to take all the time she needed, but now you’re holding it against her that she took you at your word. If you didn’t really mean “take all the time you need, no matter how much that is,” then you needed to use different language — like “Why don’t you take the rest of the week off?” or “Why don’t you take the rest of the week off and then we can touch base about what you’re thinking after that?”

For what it’s worth, I don’t think the amount of time she’s taken is excessive! But the bigger issue is that, as far as she knows, you’ve actively encouraged her to take it. Plus, people do have crises that can result in them suddenly missing a lot of work; this is one of them.

In any case, at this point you’ve made the offer and walking it back wouldn’t be great. But you could say, “Can you give me a sense of what you’re thinking your schedule will look like over the next few weeks? I’m trying to plan and ensure we have enough coverage, so that will help me know if we might need to push some work back.”

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My first reaction is to want to dribble LW like a basketball.

*takes a breath*

My second is to be glad LW wrote in instead of punishing Jessy for being human and not being telepathic.

My third is to want to dissect LW's response because it's interesting.

Overall, LW seems to be thinking "I'm upset so the only possible reason is that Jessy must be misbehaving." It's especially intriguing that LW said "take all the time you need" while having a set number in her head instead of telling Jessy that number. I also really find it interesting that LW wants to tell Jessy, who recently suffered a death in the family, "your absences have hurt us."

Frankly, I hope LW can pull her head out of her ass. She does describe herself as a first time manager so maybe she actually does want and intend to learn. We can only hope. Most managers who would describe an employee's bereavement this way would never doubt their own judgement.

Ouch, this hits close to home right now.

FWIW, any death, but particularly the death of a parent (or parent-in-law), can lead to a lot of time drains, whether it's planning services/burial/cremation, arranging the disposition of the estate, cleaning out a living space, taking care of pets, notifying others...you get the idea. I've hardly been involved with all of this with my mother, and I've still had to take three days off work.

When a coworker's mother died, and she flew back to Spain to deal with it, she was away from work for more than two weeks, and the boss was very supportive.

Deaths take A Lot Of Admin, quite apart from the emotional effects (and the physical effects of those emotional effects)

*hugs you sustainingly*

Absolutely amazed by LW's statements. Apparently they can't hear themselves!

Some commenters had said "LW 1 is just stressed and will come to her senses" but in my experience stress, like anger, shows who people really are. And this exchange is pretty illustrative:

LW 1*
September 15, 2025 at 11:38 am
That’s not it at all. Jessy is not new to the workforce. I thought she understood that she could be okay taking a reasonable amount of time off, not disappearing on me for two weeks with projects halfway done.

Reply
▼ Collapse 7 replies
Ask a Manager*

September 15, 2025 at 11:40 am
Whoa, wait. Did you read/process the reply I wrote to you? I’m asking because you’re sounding like you haven’t grappled at all with the fact that you told her to take as much time as she needed — this is on you, not on her!

Also, three days the first week and three and a half the second week is not “disappearing”! She was clearly in some contact because she was working some days.

This is also a normal amount of time to take off after a death, particularly when your boss tells you to take all the time you need.

Exactly. LW's whole letter shows a clear pattern of self-centered thinking and lack of empathy. They clearly think everyone else is crazy and that the only reasonable interpretation of "all the time you need" is whatever imaginary calculation they came to for what would make sense, and even after the answer, which was explicit and literal!, have not grasped that it's even possible for "all the time you need" to mean "all the time you need". They think an employee who asked their supervisor for direction is blameworthy and rude for following the direction she got instead of the secret other directions they were transmitting telepathically! It's not a stance you just accidentally come to in the heat of the moment.

Edited 2025-09-15 16:37 (UTC)

Alison has popped up in the comments at least three times to say "Um, LW, pause a minute and reread". That's when you know LW really needs a whack with a clue brick.

She's now actually asked the LW to stop commenting!

At this point, I don’t think you’re engaging in good faith so I’m going to ask you to stop commenting and reflect on what people, including me, have told you here.

criminy.

Also people are pointing out that it is extremely vanishingly rare for the AAM commentariat to be 100% in agreement of ... literally anything

but 100% of the comments to LW1 are a) you're wrong, and b) the workplace is full of evil bees

and that even the people giving LW the most benefit of the doubt are in agreement

cripes. reading through this it seems like LW1 wanted AAM to say the employee was bad and wrong, and got their back up really badly when everyone disagreed.

Holy crap, this is the first time I've ever heard of her doing that!

Wow.

Based on my experiences in HR, this happens a lot. The supervisor wants the credit for being the nice manager who says "take all the time you need," but doesn't want the inconvenience of the employee actually taking them at face value. I wouldn't have thought I would have to say you can't punish employees for taking time off when you told them they could, but I was wrong!

Also, if LW's estimate of how much time Jessy would take was two or three days (!), I have to assume LW has never actually dealt with an unexpected death in the family. The logistics alone are not going to be handled in two or three days.

Also, if LW's estimate of how much time Jessy would take was two or three days (!), I have to assume LW has never actually dealt with an unexpected death in the family. The logistics alone are not going to be handled in two or three days.

ABSOLUTELY THIS.

Yeah, I had a manager once where I put in a leave request and then they berated me for requesting leave on a day when we were shortstaffed and how much work they would have to do for coverage now that it was approved, and I had to sit there while I was being berated thinking "....you could have refused it then? that's why it starts as a request? that's why you get paid a manager salary?"

This seems like the same sort of thing but even less self-aware. Employees can have all the leave they need! They just need to be able to telepathically detect when they shouldn't take it so we don't have to tell them!

lord i HATE this.

The supervisor wants the credit for being the nice manager who says "take all the time you need," but doesn't want the inconvenience of the employee actually taking them at face value.

Yeah, I think you’ve hit the nail on the head here, with perhaps an extra side of “the supervisor hasn’t introspected enough to even fully realise that’s what they’re doing”. I can scrape together maybe 1% of strained sympathy for LW on this, because I’ve absolutely been guilty of defaulting to what I thought of as rote niceties on the assumption that the other person would be playing the same “after you! no, really, I insist!” game as me and then feeling taken aback when they instead took me at face value. (Not relevant to this letter, but it’s a culture clash I encountered a lot when I first started making friends with Americans.) But 1) there’s no excuse for blame-shifting to the other person like this, you’ve still gotta be ready to own and honour your own damn words! And 2) in a cultural environment where indirect communication is the norm, a big part of what authority figures like managers are FOR is to cut through that awkwardness and say what others don’t feel free to. Niceties are for communicating upwards and horizontally, not downwards. 😬

Ask culture vs. guess culture! In my experience it’s largely regional in the US, and it gets super messy when you live in a city with lots of transplants and nobody speaks the same “language.”

This is one of the reasons why "unlimited time off" is bad for employees and a scam: Jessy can look at her available time off and say yes, I have that time available. Whereas every vacation day a person takes with "unlimited time off" is actually "play guessing games about what my boss, who is potentially a complete jerk, will feel is appropriate."

I read an article about a company that had had unlimited time off until they looked at the numbers and realized that people weren’t taking it, so they switched to “unlimited time off plus you’re required to take x days of paid vacation per quarter”.

Oh, people who honestly meant an employee benefit to benefit the employees, how nice.

I mean, well-rested people are also more productive. But many companies don't want to know that.

Yeah, this is definitely "actually communicate your actual expectations" time.

I thought "excessive" was going to be 1-2 months...

At first I thought that she'd taken time in addition to her allowance. Reading the comments, it sounds like she took the days she was entitled to, but the manager thought it was a bad time. Is any other time going to actually be better??

I guess if someone had a *minor* crises that might be fixed in a couple of hours, I might say "take all the time you need" and assume it was obvious I meant "hours, or maybe days" not "weeks". But I can't imagine *never* needing more than 3 days for a death. I guess it also depends on who's death -- if it's husband's parent, it may very likely need them taking care of a lot of bureaucracy. If it's a cousin, ok, maybe they don't need to do as much. But I assume she took the time because she did need to.

It sounds like boss is overworked, but that's not employee's responsibility to fix.

OTOH, in other circumstances, if boss has made a mistake in saying something too generous, but what they actually wanted from the employee was reasonable, I think it's reasonable to explain that and ask if employee can change plans (although not to retract anything the employee has massively relied on, or to blame the employee, or to breach a contract made).

I get the feeling it was partly "I am horrifically overworked" (i.e. company needs better infrastructure for hit-by-bus/won-the-lotto factor) and partly toxic company culture is toxic.

I think it would be valid for LW to say something like "we're really swamped, I know you're still grieving but is there any chance you can [XYZ] this week", but not blame J for ... not reading her mind. Or not making arrangements in advance (wtf).

LW: "Myself and others have taken two weeks off before, with the planning in place similar to what you mentioned, lots of instructions and backup plans in case something sudden came up. Jessy basically vanished for two weeks with several projects in mid-stream, leaving work undone and clients wondering what was going on."

Gosh, how dare she not do advance planning for an unexpected death...

LW: My manager was well aware of the situation the entire time and agreed with my assessment. We are in the process of doing more hiring but obviously that does not happen overnight.

Reply: Agreed with which assessment–that Jessy should take the time she needed, or that Jessy needing time is an indictment of her work ethic?

LW: He agreed that Jessy’s time off was excessive.

Reply: Oof. Just oof. No wonder he’s letting you take 12 hours days and weekends. Is he sitting back and letting you work yourself to death, or pressuring you that “the work needs done”? Either way, it’s telling us a lot about him, and none of it is good.

LW: We both understand that the work needs to get done. It wasn’t just him. When I mentioned Jessy’s absences to other managers and coworkers whose projects were affected, the response was always “wow, that’s a lot of time off.”

[wonder if LW told them everything including having said "take the time you need"]

LW: There’s this weird thread here that I told her she could take as much time as she needed. I only told her what her PTO balances were. I didn’t say she could take so much of it at once. Then when I knew more about the situation I approved her piecemeal requests because, despite what many people here think, I’m not a terrible human.

LW: The expectation came from the fact that the company offers 3 days of bereavement leave, and all of my colleagues in the past have never taken off more than that for a death in the family.

She was unreliable because she left multiple projects unfinished or halfway finished, with no guidance on how we could pick things up and see them to completion, if she was going to be able to finish them herself or what we were supposed to tell clients.

AAM: That is what people do when they have a sudden family emergency or health crisis. It is normal. It sound like she’s been in for a few days during this, so if you needed info on projects from her, that was the time to get it — that’s part of your job as her manager!

And again, you told her to take all the time she needs. If you meant “3 days,” you needed to say 3 days! You are being unreasonable in expecting she should have read your mind. I don’t think you’ve engaged at all with that part of it.

Seriously, why did LW write to an advice columnist if she was already so damn right about everything? (I mean, obviously, to hear how damn right she is. But.)

Leaving aside all the other bullshit (the insistence that Jessy read their mind, the changing of the story in what they wrote in the letter, the unreasonableness and selfishness from someone who wants to be seen as the Hero without any inconvenience, the conflation of 6.5 days spread out over two weeks to "two weeks of leave"):

It’s not just this workplace. It was very standard at my previous workplace of 12-plus years as well. Same with my boss — he has worked elsewhere and said he’s never seen anyone take off as much time after a death as Jessy did.

It’s also true for my friends and family. I’ve only ever heard of someone taking off a week at the most.

LW 1: Way to make it clear that you live in a place with either zero Jews or a lot of antisemitism. (Probably other religious and cultural groups require a longer bereavement as well but I only know from Jews.) If your area has any Jews, then at least some managers know perfectly well that lots of people require a week for certain bereavements.

Also you're lying, LW: absolutely nobody in a job where there's benefits like PTO expects the norm that a grieving parent will come back after three days, and amongst all your friends and family somebody has known a colleague who lost a child. Individual bosses and companies will absolutely have shitty expectations for grieving parents, but it's not the norm, FFS.

FWIW:

I had a boss who told me to put in for bereavement and not (limited) PTO when my best friend's parent died and I had to go be with her, and when I protested that parent's mother wasn't in the benefit, she told me not to be stupid, I was bereaved, wasn't I? I should take bereavement leave and go be with someone who needed me.
I had another boss who, when I came back to work after my father's shiva, tried to make me take more leave, and only relented when I told her I needed to be at work just then. That boss was also fine with me running out constantly during the six months before he died, every time I got a call that made me run to the hospital.
I have had multiple bosses who told people (me, or colleagues) who were sad about the death of a pet to take the rest of the day and maybe tomorrow.

I have never in my life encountered a boss who wouldn't try to get you a week after a death in the family. I know they exist, but seriously, WTF.

Edited (clarifying that you only need to know if you're a manager) 2025-09-17 04:40 (UTC)

There’s this weird thread here that I told her she could take as much time as she needed.

encouraged her to take the time she needed

Does LW think "the time she needed" is different from "as much time as she needed"?

I only told her what her PTO balances were. I didn’t say she could take so much of it at once.
I could be wrong (laws about PTO vary) but isn't your PTO pretty much yours to use when you want it?

Not necessarily - it's definitely allowed for companies or managers to require you to request a certain amount of time in advance for some kinds of leave, or block off certain times when you can't take it, as long as they don't put enough limits on to stop you from taking it at all. For example tax accountants are often barred from taking vacations at the end of tax season.

(This is obviously not true of sick leave or bereavement leave, but that doesn't stop managers like this from existing. But tbh it probably would be... not great but not completely off the wall for this LW to have given her the three days' bereavement leave right away and then asked that she give a certain number of days of warning if she needed to take more leave for administrative reasons or the funeral. Although this LW doesn't seem to understand that the administrative needs would even exist.)

It sounds like they have a horrific company culture.

I… encouraged her to take the time she needed. I expected this would be two or three days at the most.
People are not psychic, LW. You do not work for Xavier's School for Gifted Youngsters.

Someone died, LW. Someone died unexpectedly. Not only is that emotionally difficult but it could also be logistically complicated and require a lot of business hours phone calls, et cetera.

LW needs better work-life boundaries and their workplace is understaffed if one person being off intermittently - again, because someone in their family died unexpectedly - is causing this much chaos. That might not be something LW can fix but it's worth mentioning.

When I saw "excessive amount of time," I was thinking six weeks not six days. Jesus Christ, LW. Do you know how to human?

I want to shout in LW's ear: IF YOU'RE DROWNING IN TOO MUCH WORK AND BURNING YOUR CANDLE AT BOTH ENDS TO COVER JESSIE BEING OUT,

IT'S NOT HER FAULT.

IT'S YOUR COMPANY'S.

FOR NOT HAVING ENOUGH PEOPLE TO COVER SHOULD ONE PERSON BE OUT FOR BEREAVEMENT, OR SICK IN THE HOSPITAL, OR WHATEVER ELSE COMES UP.

Fuck, we're never escaping the crab bucket at this rate.

There was no one else who could step in, and one contractor we reached out to never responded

ONE contractor? LW needs contingency plans for their department because employees WILL become unavailable from time to time. LW is getting all twisted up about whether their employee is taking “too much” time off. Well, what if the next time an employee is unavailable it’s because they were hit by a bus? I’m not sure if this is the fault of the company or LW’s managerial inexperience or both.

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Ask a Manager: I Didn't Expect My Employee To Take So Much Time Off...

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