I’m going to lose hundreds of dollars on a “perk,” coworker told interns the wrong dress code, and more

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

1. I’m going to lose hundreds of dollars on a “perk”

I manage a restaurant and also bartend (I’m still hourly) and one of my perks is a week in the owner’s AirBNB that they bought less than a year ago. It has been offered to all of us in management and our GM went with his family about two months ago with no problems. My group is set to leave in a few weeks, and I was just told this afternoon that the owner’s wife accidentally double booked for the week I’m going. Our tickets are already bought for our flight (four of us) and because they were bought so long ago, we cannot get a refund. We live in Pennsylvania and the house is in Florida, so we can’t just pick up and go another day.

We didn’t actually pay anything for the house since it was a perk. All we are asked to do is pay for the cleaning services and get our own plane tickets, so I have no legal contract that it’s been booked. I do have messages from months ago going over the dates that she had free and so on. So now, just today, she tells me the other guests cannot change (even though we booked before them) and I need to pick another week in the next few months with very little to choose from, and try to talk the airlines into refunding or giving us vouchers. The airline will do the vouchers but with a fee.

My issue is, our restaurant is not going well so I am not sure we will still be there in the later months, plus this is the second time she’s canceled my week down there so I really just don’t trust that it will ever happen. How do I go about communicating that we would like to be refunded for our tickets and not try again? These are my bosses so I’m really stuck, but I’m also furious and very hurt. The three women I was planning to go with do not want to try again either. I am beyond stressed. I have been struggling financially so I cannot at all just eat this few hundred dollars.

The right thing for your employer to do would be to book you and your friends into different lodging for the same dates and cover the cost themselves. It was their screw-up, and they should take responsibility for fixing it. It’s far from right that you’re now out hundreds of dollars for what was supposed to be a perk.

I would say it this way: “I understand mistakes happen, but my group isn’t able to reschedule and the airline won’t refund us. Right now I’m out hundreds of dollars for trying to use a perk, even though I confirmed the dates would work before booking our tickets. So that I don’t lose this much money — especially at a time when finances are really tight for me — would it be possible for the company to cover different lodging for us that week?” If they won’t do that, then you could say, “In that case, would you cover the cost of the airline tickets? I booked them once you gave me the go-ahead and that’s a lot of money for me to lose.”

There’s no guarantee they’ll do it, but it’s a very reasonable thing to ask for.

2. Did I overshare with my boss?

I am a young professional who recently started a new job and I really enjoy working there. My boss is a nice guy. We get on very well and we regularly have friendly discussions (my desk is in front of his office and I am his assistant so he frequently talks to me about his weekend or kids).

I have a sibling in Ukraine and there is a lot of stress in my life surrounding that. I don’t talk about the situation all of the time, but my boss has asked about them a few times and when there is a major situation change, like leaving a combat zone or going back into a combat zone, I will mention it to him (probably once every 4-6 weeks). I thought it was a good idea for him to know about my connection to the crisis and a major stressor in my life, but a friend has warned me that sharing too much with a boss is a bad idea since if the company thinks I am too distracted by what is happening, they might choose not to renew my contract or my boss might choose not to give me new responsibilities because of the stress I am dealing with. I am still on probation so I am trying not to mess this up. Did I overshare by talking about my sibling’s situation in Ukraine? I obviously care more about my sibling than anything else, but I really need this job too.

How much to share with a boss is always a judgment call (based on the relationship and what you know of how they operate), but if your friend is giving that as blanket advice (not specific to your dynamics with this particular boss) they’re overreacting. Assuming that you’re performing well and are focused most of the time when you’re at work, there’s nothing wrong with sharing something like this with a boss who you get along with and who seems like a generally decent and caring person. Your friend is being excessively cautious.

3. Should I mention my grad school plans in a job interview?

I was just offered an interview for a role at an organization that I’m really excited about. However, I am applying to grad school in the fall, and I’m struggling with how to explain my future plans in said interview. My thought is that I will decrease my chances of landing the job if I essentially say, “I’m planning on going to grad school in 14 months, but if I was hired I would still want to stay on as a remote employee.”

If I don’t mention it, or just keep it as vague as “I’m considering applying to grad school in the next few years,” and am hired, then I run the risk of burning bridges when I tell the employer next summer “actually I did apply to grad school and am quitting.” What’s the best way to handle the situation? Am I overthinking this? My current job sort of stinks, and I’m really excited at the prospect of something new.

Don’t disclose it. It’s 14 months away and a lot could change between now and then — you might not get into grad school or might decide not to go after all or might not even end up applying in the fall. Also, even aside from the uncertainty, 14 months is far enough away that it’s not egregious to accept a job now; if grad school were looming at the end of the summer or something else much closer to now, that would be different.

4. Coworker is telling my interns they can only wear jeans on Fridays, but he’s wrong

I manage a group of interns in an organization where the dress code has been fairly relaxed since people returned to the office. This mostly looks like people wearing jeans on non-Fridays. However, one of my coworkers (who is not directly responsible for the interns) keeps telling the interns, “You can wear jeans on Fridays because that’s our ‘dress-down day.'” Personally, I don’t care how the interns dress on any day as long as it’s clean and reasonably presentable (which is also the view my boss holds), and since other people wear jeans in the office on non-Fridays, I find it unfair to impose a different standard on them. I know I should have gone over dress code with the interns earlier, but is there a good way to approach that with them now?

Yes! “I should have gone over our dress code earlier, so let’s do it now” — and then give details. If you feel like it’s weird to contradict what your coworker told them, you could say, “We used to only allow jeans on Fridays, but things have relaxed since the pandemic, and I am giving you official permission to wear jeans any day of the week as long as your clothes are clean and reasonably presentable — for example, they shouldn’t have holes in them.”

It sounds like you’re confident your boss agrees with that, but if you haven’t explicitly confirmed that with her, it’s worth doing that first so you don’t inadvertently set the interns up for problems if it turns out someone objects.

5. Covering travel expenses for junior employees

I took a position five years ago as a junior employee that involved a good amount of traveling. I was told that we pay for our travels and are then reimbursed. I was also told (quite kindly) that if I wasn’t able to or preferred not to put it on my personal card, a more senior member of the traveling team would pay for mine and be expensed accordingly.

I had to take them up on this offer for several months of travel due to having been unemployed for a few months prior. I felt like a complete chump — just awful and inadequate the whole time. I was so embarrassed having the senior team member ask for my check to be included at meals, and for them to check me into my hotel.

Now I am financially stable, I can afford very easily to put the trips on my personal card (and enjoy the points!). I would be more than happy to pay for and actually even would like to help a junior employee in a similar situation as I was. When this happens, how do I make this person feel not like I felt? My feelings of inadequacy colored my performance in all areas on those trips — I was timid and downtrodden. I don’t want a junior employee to be concerned about money whatsoever!

And the thing is, my company did all the right things for me. They never required me to put expenses on my own card and never said anything to make me feel bad about it. But I still felt bad! Is there more I can do to make sure junior employees never feel bad like that? I know you’ll say we need company credit cards, but that’s not possible (or rather not in my control).

First, offer it proactively rather than making anyone approach you for it — “Let me know if you’d like me to put your expenses on my card; I’m happy to do it and I know it can make things a lot easier when you’re junior.” And second, be super matter-of-fact about it, like it’s completely normal and not in any way A Thing, and if someone seems uncomfortable consider throwing in, “I don’t love that we don’t have corporate cards; I know it can be tough to swing these trips when you’re junior and I’m happy to handle it for you, just like someone always did for me when I started out.”

At the same time, though, don’t go overboard, and pay attention to people’s cues. Not everyone will feel as uncomfortable about it as you did, and you risk adding to any awkwardness if you’re more focused on it than they are!

{ 280 comments… read them below }

  1. lyonite*

    Ugh, OP1. Your boss sucks, but you probably already knew that. This “perk” is clearly only on offer if they don’t have anyone willing to pay to rent the place, which would be not so bad for a local getaway (and if it was clear from the get-go), but to do it for somewhere you have to pay to fly to is a lousy act. Good luck getting some kind of recompense, but I’m afraid this is just going to be an expensive lesson to not trust them.

    1. Captain dddd-cccc-ddWdd*

      Yes, perhaps I am just cynical but I didn’t think it was actually double booked “accidentally”… you can try asking for money back for the flights / an alternate place to stay etc but it seems possible that they’ve done this double booking for a cash injection so there may not actually be any money…

      1. Kwebbel*

        My thoughts exactly. And, even if I am willing to give the owners the benefit of the doubt and assume the double booking was an accident, I am a lot more skeptical about their “the other guests are even more inflexible than you” story. That one smells real fishy.

        1. EPLawyer*

          Especially as it happened TWICE. This perk is only a perk to THEM.

          Honestly OP the business is struggling. try to get your money back, or suck it up and take the airline vouchers with a fee (better than eating the cost) and look for another job.

          1. Not Tom, Just Petty*

            Agreed. They let staff go down as free house sitters. The OP has to pay for cleaning? OP, you are doing them a FAVOR and they are treating you like crap. They don’t block the weeks they agreed to for you and expect you to show up at their convenience to watch the place, keep it looking occupied and pay for cleaning…BTW
            Remember, no contract works both ways.
            If you end up going down (don’t), you do not have to pay for cleaning services.

            1. KateM*

              I understood the paying for cleaning as paying for the house being cleaned after them, which IMO isn’t an outrageous thing to ask – that’s like getting a free item but need to pay for shipping.

              1. Jolene*

                If you are leaving job anyway, you might have luck in small claims court. Detrimental reliance. (Obviously, this won’t work if you intend to keep this job)

              2. Not Tom, Just Petty*

                It is jumping out to me because this perk is so much not a perk. They are paying for flights, food, entertainment, uber or rental cars down there. And it’s not like they get to choose where to go on their “vacation.”
                If OP was told, “hey, we have some open weeks. If you’d be up for jumping in last minute, you can have the place for a week, but pay cleaning.”
                Not, “here is a perk of your employment. FREE WEEK IN FLORIDA! Followed by small print.
                It’s the tying it to a work perk that makes it feel skeevy to me.

            2. Artemesia*

              Paying for the cleaner after you use a free vacation rental is pretty standard. In our family when we used a relatives wonderful Oregon beach house that was part of the deal. It is a small expense and one that needs done after every occupancy.

              But of course it was not accidentally ‘double booked’ and if it was, the second person to book is the one who is dropped not the first person. I had this happen last year with a Paris apartment. Sometimes that is just being yanked around but I believe this owner whom I have rented from several times and will be again this fall and was able to adjust my schedule to accommodate him. But I was the second person to be promised the place — in this case, the OP was the first person to book and should be given the place.

              The problem is the boss of course and working for him after this — maybe time to move on.

            3. Lego Leia*

              This is how I read it, more of less. “Lending” it to coworkers is better than empty, so boss offers them weeks. Bosses wife wants/needs all of the income possible, so books paying clients as much as a possible, ignoring the “lent” weeks.

          2. yala*

            “This perk is only a perk to THEM.”

            Yeah, gonna be honest, this sounds like exactly the kind of shenanigans I would expect from folks that buy a residence to turn it into a barely-regulated side-hustle.

        2. lb*

          The other guests probably booked through Airbnb & are in a better place to complain/leave a bad review – whereas OP is getting this as a “perk” and doesn’t have the same platform to complain.

      2. Caliente*

        Yes, I would ask and expect nothing but bring it up so they know you know they ain’t doing you right, kind of a thing.

      3. Canterlot*

        Yeah – people can get pretty morals compromise-y when their business is going under. My guess is that the perk was offered for weeks when the owners didn’t think their AirBnB would be booked, as a cheap way to keep employees loyal during a time when they might not wind up getting paid regularly. But then paying guests offered to book, and the owners thought they would rather have a stranger’s money than an employee’s goodwill.

        I wouldn’t bank on the AirBnB profits being recycled into the business either. If they haven’t missed payroll already, they will.

      4. McS*

        I thought the same thing when I read that it happened twice. And I think it’s likely to happen again if they reschedule. The week was open when OP bought flights, but the owners didn’t remove it from listing on AirBnB and when someone paid for it, they let the booking go through knowing they could kick their employees out.

    2. JM60*

      I wonder how accidental that double booking really was. The boss may have decided that they’d rather get paid by the AirBNB customer rather than honor the free booking they promised to their employee.

      1. Felis alwayshungryis*

        My first thought too…betcha they got a paying booking for those dates.

        1. GythaOgden*

          This is why my mum and dad don’t rent out their holiday cottage near Swanage. They gift people they trust weeks there (like my friends have had times there, both singularly and collectively, and I have a key of my own), but they want to be able to go down there spontaneously at the best times of year (my dad is a keen amateur photographer and catching the sunrise over Corfe Castle is a passion of his), and don’t want the hassle or grief that comes from this kind of scenario.

          I admire their generosity in not seeking to profit from it. They could rake it in, but they choose not to, so that they could genuinely offer the use of it as a perk/gift and not have it conflict with an income stream. They debated opening it to refugees in the spring as well so people could have a semblance of a private life rather than feeling like intruders in someone else’s home, but I don’t think that plan got very far along as the place is a bit isolated from a lot of amenities and community resources a family coming in would actually need.

          1. Storm in a teacup*

            Ooh Swanage was our staycation last year – so beautiful around there and Corfe castle was gorgeous. Your parents are so lucky to have such a lovely spot!

            1. GythaOgden*

              It’s so nice to be there! It helps that the house was not really the best shape or layout for a family home, so they got it cheaper than expected. I call it the ‘brick tent’…

      2. londonedit*

        Yeah, there was a lot of that going on with holiday lets and Airbnb here when things were first opening up after the lockdowns – people realised they could get a lot more money from people desperate to book a holiday in 2020 than they could from the people who’d already booked in 2019, so there was a lot of ‘Oh, so sorry, terrible error but we’ve double-booked, you’ll have to find accommodation elsewhere’ when actually they’d just jacked up the price and booked in another party. I wouldn’t be at all surprised if someone had made an enquiry about booking the property that week and the boss had decided to get some money for it rather than letting the OP use it as planned.

    3. Language Lover*

      I agree.

      The lw said that this was the second time the date was changed by them. I’d love to know what happened the first time.

      I suspect they’re agreeing to the dates but not blocking off the time in Air BnB, VRBO or whatever services they list on to see if they get a paying customer. They might not accept a booking if someone wants to do it for just a weekend but if someone requests the full week, the employee gets the boot.

      It’s a really thoughtless thing to do, especially with no warning. I hope you get your money back but I’m not holding out much hope.

      1. I Wrote This in the Bathroom*

        I was mystified by the owner’s and wife’s behavior, but this sounds like a very likely explanation for it. I bet this is what’s happening. Big red flag if so.

    4. I'd Rather Be Eating Dumplings*

      Yes, I’m so annoyed on OP’s behalf. There is something particularly grating about someone who makes a big show of offering “perks” or “favors” but only when they are at no cost to them.

      (To be clear, it’s fine to offer a favor that is easy/free to provide, it’s just the positioning of this as a “perk” or a “benefit” when clearly it is more to the benefit of the employer — who gets to double-dip the value of their house by using it both as an employee benefit AND for rental income…is annoying to me. It feels like there is no good will or generousity underpinning the offer, otherwise they would be apologizing and trying to work with OP.)

      1. Slow Gin Lizz*

        Right? This absolutely doesn’t sound like a perk to me. I think the fact that the location is not within driving distance and requires the employee to buy plane tickets immediately knocks it out of “perk” territory to me. It’s really just a nice favor, not a perk. A perk would be free. And add in the fact that the boss keeps double-booking (I agree that it doesn’t seem likely that that’s an accident) and it’s actually the opposite of a perk.

        I desperately want to know if the boss is equally untrustworthy in other areas as well. The fact that the business isn’t doing well speaks to me. OP, there are a lot of restaurant and bartending jobs out there now and if you can deal with a job search, I’d recommend starting one. And please let us know how things are going, we are a curious bunch, after all. Good luck!

        1. I'd Rather Be Eating Dumplings*

          I desperately want to know if the boss is equally untrustworthy in other areas as well

          I have to admit I’m curious about their financial savvy; buying a vacation rental while their restaurant is on the rocks seems like the move of someone who isn’t realistic about risk.

          1. Slow Gin Lizz*

            My thought is that they are independently wealthy and have multiple properties and business ventures, but your scenario seems equally likely.

          2. Canterlot*

            Ah, restaurant owners. Some of the best and the worst people I’ve ever worked with. It is, unfortunately, a risky type of business with razor thin margins.

        2. HBJ*

          Speaking just to the is this a perk or not part of this discussion. I disagree. Housing is the most or the second most expensive part of a vacation. This is a huge perk. The employees don’t have to use it if they can’t afford the other costs associated with it. A company doesn’t have to pay mileage for the drive and a workout clothes stipend if they provide a gym membership as a perk.

      2. Not Tom, Just Petty*

        The 21st century white elephant is indeed a “free vacation home.”
        You have to pay to get there. You have to cover food and drink and entertainment while you are there. You have to pay for a cleaning service when you leave.
        I’ll say it again, no contract for the owners means no contract for the staffers. Pay what cleaning fee? Nope.

        1. New Mom*

          LOL. This could be an SNL skit. Opens with the company perk announcement and everyone is excited and then the family arrives and the house is disgusting and has old food in the fridge, and finds out that the landscaper was actually illegally living in the house (this really happened to me at a “free vacation home”).

      3. New Mom*

        Yeah my husband’s old company had a “company cabin” but it was really the CEO’s family cabin that he wanted a tax break on. So he blacked out all holidays and a lot of the winter and summer. It was in Tahoe which was cool, but requires hours of driving, buying and lugging everything that you needed, and then random things would not work at the cabin that were listed in the guide which was disappointing but we couldn’t complain because it was a “perk” provided by the CEO.
        There was also no one who was managing it so one weekend we went up and another coworker and his family went too even though we had been on the sign up sheet for more than six months and the guy literally texted my husband when we were there saying they were on their way up. To me, not really a perk to have to awkwardly share a kitchen and do small talk with strangers when I just wanted to relax and drink beers in nature with my husband.
        I really hope OP gets their money back!

      4. Princesss Sparklepony*

        This falls under my adage that Things you get for free are the most expensive.

        The owner’s shenanigans are going to cost LW over and over again. They have cancelled twice on her, third time could be the charm but it’s unlikely.

        The owners get the kudos for offering the “perk” (look how generous we are!) but never or rarely do the employee get to use the perk. The perk costs the owners nothing since they already own the place and now they are replacing the perk with a paying customer. But the employees get the short stick every time.

        The thing to me is that once you can have the double booking problem with an employee, but twice, nope that isn’t double booking. That’s at best carelessness but more likely calculated to maximize profit on unit and no concern for employees. If the condo was driving distance I’d have more sympathy possibly.

    5. Not So NewReader*

      It would depend on the particulars of the setting, but I might be tempted to try, “I am embarrassed in front of my friends. How do I explain to them that their money is gone?”

      I am sorry to say, OP, but your boss is not a person of their word.

      1. Petty Betty Crocker*

        Oooh. “They are already mad about the first cancelation and we’re taking bets on a second one. Being told we can’t refund our airline tickets will be another reason for distrust. Is there any way you can help salvage this for us?”

        But ultimately, this isn’t a perk. As an outsider, we know this is about *appearing* generous to staff, but really they aren’t. They never expect their staff to have the funds to go to Florida to visit the property, so they will always prioritize paying customers, or family, or friends, or anyone they don’t actually pay.

    6. Bagpuss*

      Yes, I think that the host can cancel an Air BnB booking so Boss could cancell the other booker even if they are saying they are not flexible – but of course they would be given a refund so Boss would be out the money . IIRC AirBnB would then assist the booker to find alternative accommodation.

      It seems totoally reasonable to ask that the Boss cover the amount you’ll be out of pocket by – whether that is the charges for cancelling your flights for credit (if that’s even a an option) or booking a different place and still going.

      1. Keeley Jones, The Independent Woman*

        I am an Airbnb host, do I can offer some insight. OP’s reservation isn’t through Airbnb, the other one is. If the boss cancels the other one, Airbnb will charge boss a fee, and you get an automatic one star review and I believe more than once cancellation will lose them any Superhost stats, and if they have a lot of cancellations, Airbnb will just kick boss off the platform. OP’s boss isn’t likely going to do this.

        I’m not saying boss was intentionally being malicious here, I think in all likelihood they forgot to block those dates on the calendar, someone else booked and they don’t want to take all the penalties that come with cancellations.

        1. Person from the Resume*

          I agree. My friend who hosts AirBnB rooms in her own own home complains constantly how difficult being a host is and how difficult staying in good standing with AirBnB is. It’s probably lots easier when it’s a whole home and a newer home than my friends, but cancelling an AirBnB booking has consequences for hosts.

          That said Alison’s answer is spot on. Boss’s doesn’t cancel AirBnB, but pay for alternate lodging for the employee. Who knows if they purposefuly or accidentally double-booked? The LW should ask for lodging or refund of plane tickets. I wouldn’t count on it because they sound shady, but that is the way for the employer to make it right.

          1. pancakes*

            Right, whether it was purposeful or accidental it shouldn’t remain the letter writer’s problem. The employer should cover this either way.

        2. Bagpuss*

          That makes sense. I assumed that there would be a fee but wasn’t aware of the 1 star review etc.

        3. Not Tom, Just Petty*

          I’m not feeling that they forgot to block them, a second time. I think they took a wait and see approach. Both times. I think they are taking advantage of the staff and though I agree malicious is a strong word, they are being completely inconsiderate of others’ time and money.

          1. Books and Cooks*

            I suspect they have what I’ve found to be a semi-common attitude among people who are wealthy or quite well-off: “Oh, it’s only a few hundred bucks, it’s not a big deal.”

            I get this from my mother fairly often (a woman who tells me she is “broke” when her main checking account hits “only $20k”); granted, my mother is a pretty terrible person, but I know she’s far from the only one, and they can’t *all* be selfish malignant narcissists. I think some of them are just honestly clueless about, or have forgotten, what it’s like to not earn six figures (or more) or have inherited wealth or whatever else. They genuinely do not seem to grasp that a few hundred bucks actually is quite a big deal for many people, and that many people can’t just cover or eat that cost, and that when those people say “I can’t afford to lose this money,” they really mean it–they don’t just mean, “Losing this money will mean not going out to dinner once or twice,” or “Losing this money will mean curtailing my shopping trip next week.” They mean, “I don’t know how I’ll feed my family for two weeks if I lose this money.”

            (Note: I’m not saying it’s okay if another person’s financial selfishness/irresponsibility/broken promises “only” means you can’t buy that new dress or skip a restaurant meal. Of course it’s not. I just mean that some people genuinely seem to not understand that a few hundred bucks can be a lot more serious than those things. And I’m of course not saying that all wealthy/well-off people have this attitude, either. Just that I’ve run into it more than once in my life, and we’ve seen it in letters here more than once over the years, as well.)

        4. Falling Diphthong*

          As someone who uses AirBnB on the guest side, I do not believe for a minute the boss’s claim that they asked the renters if they would mind coming some other week, and waddayaknow they’re way more immovable than any hypothetical double booking.

    7. WellRed*

      This is why it’s never good to mix work with outside stuff, especially when there’s money involved. OP I’m unclear if you’ve even pointed out that you also can’t rebook. I doubt she’ll have any sympathy but if you haven’t spoken up you need to. She sucks. Please update us!

    8. Antilles*

      which would be not so bad for a local getaway (and if it was clear from the get-go), but to do it for somewhere you have to pay to fly to is a lousy act.
      To me, the problem is primarily that the boss didn’t say the “only if nobody else is using it” caveat.
      It’s obviously easiest for a local destination where you can potentially just figure it out off the cuff. But even for a flying destination, I could see it. If OP had known in advance, they could have figured out something – paying the extra airline fees for easily refundable/exchangeable tickets, setting aside money to pay for a hotel if needed, waiting as long as possible to book tickets, or just not using the perk at all.
      But instead, the boss has done the last-minute switch afterwards and now OP is stuck.

    9. Other Alice*

      Have to agree, it looks like the boss is giving priority to renters, which would have been okay if this had been disclosed first. As it is, LW should definitely try to address the problem but I have little hope the boss will make it up to them. LW should definitely let the boss know that they can’t reschedule and they are losing money over this.

      1. Jackalope*

        I don’t actually agree that it’s okay as long as it’s disclosed first. If it were someplace local that they could get to by driving then sure. Once they have to buy plane tickets for the trip, that means a considerable expense that they wouldn’t generally be able to get fully refunded. If I were the LW I would try to find new work (easier said than done, I know), and then leave a scathing Glassdoor review.

        1. Bagpuss*

          I suppose that if it were disclosed in advance then it would have been possible for OP to look at flexible tickets etc (and to decide if it was worth booking at all)
          As it stands however OP relied on Boss’s word and they and their friends are out significant amounts as a result

        2. metadata minion*

          Agree. I’d be totally fine if they automatically blocked off popular times of year or something like that, but it’s not ok to just cancel someone’s booking because a paying customer wants it that week.

        3. Seven hobbits are highly effective, people*

          I think it’s more “ok” in the sense that you’d know what you were getting into rather than “ok” in the sense of offering a reasonable perk that was actually a good idea. If someone told me I could use their house in a plane-ride-away location but that it might get booked out from under me if a paying renter wanted it, I’d file that under “not a deal I’ll ever want to take them up on” and cross it off the list of perks I might use in the same way that I do with their offers to pay for Weight Watchers, Toastmasters, or a gym membership. (Although those are different in that they’d make sense for someone else, just not for me.)

          A free vacation rental that could be cancelled out from under you last-minute is not a reasonable offer for most people (I guess if you happen to have family in the area, and you’d otherwise stay in their guest room but would rather have your own house if it were free?), but if the catch was upfront it’s an easy offer to not get sucked into.

    10. Imaginary Number*

      I also suspect if boss is only offering this “perk” when there aren’t rentals because they are doing something shady by claiming the cash-value of the perk as some sort of business expense for tax purposes.

      1. Not Tom, Just Petty*

        See, this is where I’m coming in. Boss is using the staff to keep the place looking occupied, getting a bonus free (to them) cleaning service between guests, and now you point out a possible third financial benefit.
        This is all good for the owners. The staffers are getting hosed.

        1. Slow Gin Lizz*

          Oh, right, I forgot about the employee having to pay the cleaning fee too. That’s ridiculous. If it were really a perk for the employees, the boss would pay the cleaning fee. Added to which, I feel that it’s not really a great look (i.e., not fair) for a boss to offer a “free” vacation (minus airfare) to employees who have financial difficulties. It seems a bit tone deaf, especially if the employer isn’t paying the employees enough for them to be able to afford a vacation on their own. I realize the financial issues of the employees might not be the employer’s fault necessarily, and definitely isn’t the boss’s business if not, but I am suspicious that the owner is providing this “perk” in place of higher wages. The whole thing is a bit sketch.

        2. Anne Elliot*

          I’m not understanding this. In my fairly extensive VRBO/etc. experience, the cleaning is always “free” to the host, in the sense that the booking party always pays for the unit or property to be cleaned after they leave. Some hosts handle the cleaning themselves between bookings — but they still charge the cleaning fee. So it’s not really a “bonus free” cleaning for the hosts; it’s a standard cleaning between parties, and it’s no more or less free than it usually is.

          If any party stays in the property, that party pays the cleaning fee, regardless of whether the rest of the stay is free or not. That seems reasonable to me. You might argue that then the entire trip is not really free and that’s true, but the staffer knew of the requirement to pay the cleaning fee all along. And since they are not going to get to stay at the property, they don’t have to pay the cleaning fee.

          The issue isn’t the cleaning fee, it’s the nonrefundable plane tickets.

          1. bamcheeks*

            Yes, it’s “the owner isn’t incurring a cost” rather than “the owner is getting something extra for free”.

          2. Keeley Jones, The Independent Woman*

            Yeah the cleaning fee here is a wash. I charge X per night plus set cleaning fee, which is just what I pay a cleaning service to clean in between every guest. (Actually I pay them more than the cleaning fee I charge my guests so I do absorb some of that myself) Even if I stay there, I have to pay to have it cleaned properly for the next guest.

          3. Student*

            Seems to me like if a company is offering free vacation housing as an employment perk, but then tacking ANY FEE WHATSOEVER onto that “free” perk, is not really a free job perk. It’s something substantively different.

            This isn’t a situation where you’re letting friends and family use your vacation rental house for a week and expecting them to pick up a minimal expense to cover your costs. This is a company billing use of this property as a perk to their employees. The relationship is different; the expectations of a job perk vs a favor are different.

            Just the fact that we’re getting this letter shows that the company didn’t really think through how to make this into an actual job perk that employees could enjoy; they are looking to make it low-hassle to themselves instead of something to attract and retain good employees.

            I wouldn’t be surprised if the owners did this to drum up their own rental business, more than anything else. Maybe they figure that if well-off employees use their AirBnB for free once, they’ll leave good reviews and consider paying for it on future vacations.

            1. Anne Eliott*

              But nothing in the letter indicates the “company is offering free vacation housing.” The letter says “We didn’t actually pay anything for the house since it was a perk. All we are asked to do is pay for the cleaning services and get our own plane tickets.” It seems like you’re arguing a perk is not a perk unless it is 100% cost-free, when it’s the OP who described it as a perk, cleaning fee and all.

              That said, I join you (and others) in suspecting that the employee got bumped when a paying guest wanted the property. To me, the owner should have either made the possibility of being bumped known upfront (“I can put you on the books for my beach house but if a paying customer wants it, you’re out”) or by treating the employee like a customer and blocking that time on the calendar as “sold” and honoring the reservation. When the OP has bought plane tickets in reliance on the reservation, the boss should make it right by paying the change fees on the tickets or getting the OP housing elsewhere. But really what the boss should have done, of course, is not taken the paying reservation in the first place, for a time frame already promised to the employee.

    11. Dr. Vibrissae*

      Not sure if someone else has mentioned it, but I also suspect you are going to have trouble getting them to cover your full ticket costs here. I’d ask for that first, of course, but if they won’t budge there, you might have luck with a counter offer to cover the flight change fees at least. You might even be able to frame it as a way to meet in the middle/let them save face, and then use those tickets to go somewhere else (not tied to this dubious perk).

  2. Caramel & Cheddar*

    5) Can junior team members get a cash/check advance instead of being reimbursed? This would let them pay off any credit cards immediately rather than waiting for reimbursement. If they’re worried about price fluctuations between gathering estimates and booking, advance like 80% of the cost (or whatever makes sense) and then have them get reimbursed for the remainder after booking.

    I feel like a company that doesn’t have corporate cards probably wouldn’t go for this either, but it’s so much less stressful for the employees that you’re forcing to use personal cards for work reasons.

    1. SemiAnon*

      I work in a place where they can’t give us corporate cards, and they will give cash advances as needed. Plane tickets go through a travel agent who bills the institute directly.

      One thing to consider is when you get people who either don’t have credit cards, or where the limit can’t handle air tickets plus a week in a business hotel. For hotels and plane tickets you really do need a credit card holder.

      1. Lyudie*

        Seconding that second paragraph. When I was fresh out of college, I would not have had enough of a credit limit to cover flights and hotel for a business trip. Maybe if it was a very cheap flight and only a day or two at a hotel.

    2. Koalafied*

      Yes, I was thinking the same thing. The big ticket items – hotel room, airfare, event registrations – you can have a senior prepay on their card. For the little around-town stuff on the trip, instead of needing to get their boss to come pay for their X every time they want anything, just give them a prepaid Visa or petty cash equivalent to a reasonable per diem for the location. (The federal government publishes their per diem rate which you could peg yours to, give it or take some.)

      If it’s within your power to influence and the company isn’t running a super tight budget, it might also consider paying it as an up front allowance rather than using it as a budget limit. They just get paid out $X/day for incidentals and they don’t have to save receipts and give back any unspent money. A lot of companies do it that way as much to reduce the administrative overhead of verifying the receipt on every $2.50 added to a subway card and $1.10 bottle of water. They just give you (for example) $50/day and let you budget that out between transportation, meals, coffee, shampoo, aspirin, or whatever they might need in the moment.

      The allowance is usually low enough that realistically there’s not much potential for abuse. At most they could eat really cheap food and not have any other expenses come up and pocket the extra money, but what difference does it take make to the company? If there was no potential to keep the surplus they’d have much less motivation to eat cheap, so the cost to the company is likely similar in both scenarios.

    3. Asenath*

      At one time, I got travel advances when I was so junior I didn’t even know if the employer had corporate cards (I think they did, but only for extremely senior people who travelled a lot). Initially, I felt a little embarrassed to ask for money in advance, but naturally Finance considered the request quite routine. So that might be an option for some employers.

      1. soontoberetired*

        my first work trip, my boss had corporate pay by check pre our going (we knew way in advance and this was 30 years ago), which I appreciated. Plane tickets were booked by travel. It was a training class and I was one of two people going – he insisted we get a car . I didn’t want one, but he booked it. turned out he didn’t have a valid drivers license or a major credit card and I ended up having to cover the transportation costs and the incidentals of his hotel room.

        Get the advance if you can .

        the company now issues corporate credit cards to anyone who asks for one before going on a trip, but they definately will pay hotel costs for you pre showing up so you have the money available to pay your own credit card right away.

    4. Snow Globe*

      I worked for a company that had employees pay and get reimbursed, but we could submit receipts immediately (such as right after buying plane tickets, rather than after the trip), and I’d get reimbursed to my bank account in about 3-5 days. So I always got the cash back before the credit card bill was due. This actually helped me – I got the points and it helped to build my credit, and I never actually had to float the cash. I just had to remember to pay the credit card company as soon as I got the reimbursement, so I wouldn’t accidentally spend the money in my account.

    5. anonymous73*

      I don’t understand why letting a senior member pay for your expenses is such a big stressor. You’re all on a BUSINESS trip. It’s not like you’re asking your mom to buy you a t-shirt on vacation. My team and I went to Laguna Beach on a business trip once and my boss paid for everything. It’s really not that big of a deal. In fact, I’d prefer it because submitting expense reports can be a giant pain in the butt. I was happy to let him deal with all of that when we got back.

      1. EPLawyer*

        It’s embarassing. You feel like a failure if you can’t even pay for your own lunch and have to ask for it to be paid. Plus you feel like if you splurge even a little, say steak instead of a hamburger, you will be judged for not being “frugal” enough and that’s why you can’t afford it.

        Unfortunately, with this set up, I don’t think there is anyway to avoid someone feeling like they are worthless with this set up. If corporate cards are not an option, then it needs to be either a per diem OR it needs to be that senior people will pay for ALL junior people. They shouldn’t have to ask. What is someone is too embarassed to ask? What if some boss is not as kind as OP’s boss and demands to see the junior’s finances to “go over them” to see what they can afford. Putting junior employees in this position where they have to ask just exacerbates the power dynamics.

        1. londonedit*

          Absolutely – I think if I was a junior employee and my colleagues were all paying their own way, but meanwhile I had to get my manager to cough up for my hotel room or my dinner, I’d feel very embarrassed and it absolutely would feel like asking your mum to buy you something on holiday. If it’s a case of ‘everyone goes out and the boss pays for it’, fine, but if everyone else is using their own cards and you’re the only one who has to ask the boss to pay for you, it’s not going to be a great look. And I also agree that it’s going to impact your decisions – if you’re paying for dinner on your own card and claiming it back, you can make a decision about how much to spend (within reason). If your boss is going to have to cover the cost for you, you’re more likely to go for something cheap so it doesn’t look like you’re splashing the cash.

        2. KayDeeAye*

          I agree with anonymous73 – it wouldn’t bother me at all to have a senior front my major expenses for a business trip, so Alison is right that the OP needs to be careful not to overdue the whole “I know it’s embarrassing” angle. Yes, it might be embarrassing for some, but it honestly wouldn’t bother me a bit, and it didn’t bother me at all back when I was a junior, either. So the OP just needs to remember that it will bother some people a lot less than others.

        3. anonymous73*

          I don’t find it embarrassing at all. It’s a work expense and has nothing to do with personal finances.

          1. Jora Malli*

            And some people are saying they DO find it embarrassing. Just because you wouldn’t feel it doesn’t mean other people don’t, and businesses should try to avoid making their employees feel stigmatized over their finances.

            I honestly hate when companies make employees pay for stuff and wait to be reimbursed and I think it shouldn’t be allowed. The business should pay for business expenses, full stop.

            1. Loulou*

              I think the point is just that not everyone would feel as OP did in this scenario — so just as people shouldn’t assume that others wouldn’t feel embarrassed just because they wouldn’t, OP shouldn’t assume the reverse. If they do, they could end up creating awkwardness where one existed before, which is obviously the opposite of their intention.

        4. Lenora Rose*

          I think it helps if the person paying emphasizes that they went through the same thing and it was fine (Without mentioning how it made them feel; in this case making it sound like it was taken in stride will go a long way towards letting the new junior person take it in stride). It might also help to mention it’s just a “Pay it forward” situation where when the junior person becomes senior (even at a different company), they can help out their own new juniors.

        5. pancakes*

          “. . . I don’t think there is anyway to avoid someone feeling like they are worthless with this set up.”

          Wait, why? It isn’t in fact intrinsic or congenital for everyone to have the same feelings in this scenario, no. For a start, for many people, a large chunk of their response will depend on the cultural and familial views around money and work they were raised with, and those vary. Wanting to be seen as demonstratively frugal, for example, isn’t seen as equally valuable in every culture or in every family. Likewise wanting to pay for a work lunch, or seeing the ability to do so as part of one’s identity, or meaningful to the degree that being thwarted dents one’s self-image.

          I agree that junior employees should’ve have to ask to be excused from personally floating business expenses – it should be standard to see that their expenses are looked after by the employer from the start. I don’t see anyone saying they should be put in that position, and a senior employee picking up the tab is going to be an easy and practical way to handle it in many situations. If the junior employee has big feelings about that part, I don’t think those are or should be on the employer.

          1. Loulou*

            Yup, it’s certainly not inevitable that everyone will feel like that! But if you act like it’s a huge deal, that’s a good way to make people feel like that even if they would have thought nothing of it otherwise.

            1. pancakes*

              Who is suggesting acting like it’s a huge deal, though? The advice is to be matter-of-fact about it, and I don’t see anyone recommending a big speech or something.

              1. Loulou*

                Lol pancakes, love the energy but I was in fact agreeing with you! Keep it low key, don’t make it a big deal (including by getting really in your head about how this is a universally humiliating experience)

      2. WellRed*

        I suspect it’s all in how you frame it. As in, it’s not that you can’t afford to buy your own lunch, it’s that you’re not expected to buy your own, it’s a business expense. It’s not unusual even if you have your own card for the senior exec to pick up the tab. For little incidental like a bottle of water, I wouldn’t ask but would submit for reimbursement. Companies: if you want people to travel, get them corporate cards. It’s not hard.

        1. Jora Malli*

          I don’t have a work credit card, but when I travel for work my airfare and hotel are booked by the finance department, who do have cards, and I’m issued a check for my food and transit expenses before I leave. Even if you can’t give every employee a credit card, you can still cover their expenses up front so they don’t have to use their own money for business purposes.

      3. Hlao-roo*

        I am picturing a situation like this:

        Bob, Jane, Linda, and Fergus are all on a business trip. Fergus is a junior employee and doesn’t have the money to front the costs and wait for reimbursement, so Jane is covering for him and fronting the costs for herself. Bob and Linda are fronting the costs for themselves. They all go out to dinner together and ask for separate checks but oh, actually, can you put Fergus’s meal on Jane’s bill please?

        So now Fergus feels embarrassed because Bob and Linda know that he can’t afford to pay for the business costs up front and be reimbursed later. Not that he should feel embarrassed, just that this is a very different situation than Linda paying for everyone’s dinner.

        1. KayDeeAye*

          Again, everybody’s different, but that wouldn’t bother me in the least – whether I was Bob, Jane, Linda or Fergus. It wouldn’t have bothered me when I was a much younger person, either. But as I said, everybody’s different, so as long as the OP keeps that in mind, all will be well.

        2. Ellis Bell*

          I don’t think that’s an unrealistic scenario, but it’s a bit of a ham fisted one you would hope people could easily avoid. Surely Bob, Jane and Linda would be used to the fact that there is often a junior employee unable to front funds. With their background knowledge, I would expect one of them, most probably Jane to say “Why don’t I get the cheque for all of us, to save the waiters splitting the bill. There’s only one set of expenses that way as well.” If Jane was lax in that respect and forgot to cover the cheque more smoothly without referring to Fergus, I would be fleetingly embarrassed in Fergus’ situation. But I’d be more embarrassed for the lack of smooth manners, and the lack of company credit cards than I would be for myself.

          1. Hlao-roo*

            I based my scenario off of the letter writer’s sentence “I was so embarrassed having the senior team member ask for my check to be included at meals,” so it sounds to me like the senior team member who was fronting the LW’s costs was not smooth enough to cover everyone’s meals.

            I agree that the Bob and Linda’s of the situation probably aren’t judging the Fergus’s of the situation, and that it would be smoother for the senior team member to cover everyone’s meal on one check.

            1. TechWorker*

              Also, senior member of staff may feel totally fine about fronting 2 meals, but not 10 meals… or not wanting to sort out expenses for 10 people vs 2. I don’t think there’s a perfect answer here

              1. pancakes*

                “I’ll put expenses for my department on my card, so here, this is for me and Fergus.” Or something along those lines. A bit awkward, but better than having Fergus take the lead in trying to sort it out. In any case, it would be really weird for the other people present to assume that Fergus doesn’t have any money, or make other assumptions about Fergus’s life (?), on account of him not paying for his own work lunch.

      4. Agile Phalanges*

        Yes, companies I’ve worked at have actually REQUIRED meals to be paid by the most senior person present (or one of the most if multiple at the same-ish level). This is because if a junior person expenses it, then their manager approves it, it may never be viewed by someone who wasn’t attending the dinner (or whatever). If the most senior person does it, it goes to THEIR approver, who presumably wasn’t there or they would’ve been the most senior). Also, they often have an admin to handle their expenses, whereas more junior people would be handling the extra work themselves (listing all the attendees or whatever). It also just makes sense to minimize the number of checks to request from the server as much as possible, so one check for the table instead of five separate ones or whatever. I realize in this day and age, it’s a lot easier for them to separate tickets, but still harder than just doing one ticket per table.

        Similar theory with shared rental cars when a group is going on a trip–most senior one pays, but anyone covered on the company insurance can drive.

        So I don’t think it should be at all embarrassing to have someone else paying your meal when it’s a business meal, and I also don’t think people should make assumptions based on who’s paying when they see other folks out and about. [My boyfriend’s mom once got pissy because he paid and I didn’t even offer, and it’s because he was paying with a joint account that we both contributed to!] Of course plane tickets, hotels, and conference fees often have to be paid for separately, which can result in the need for an advance, someone else putting it on their card, or other solutions. But again, it shouldn’t make a person feel embarrassed. Not all of us have a ton of liquid cash just sitting around to pay for work-related expenses.

      5. Elsajeni*

        Well, there’s a difference between having the default be that the most senior person handles expenses for everybody — as seems to have been the case on your trip — and having the default be that everyone fronts their own expenses, but if a particular junior employee can’t afford it someone will step in to cover them. Of course some people will find it embarrassing to be presented with the assumption that they can afford XYZ and have to speak up individually and say “actually, I can’t afford that, what is the backup plan?”

    6. Chelle*

      My company doesn’t have corporate cards but will do this! It can be difficult to estimate how much you’ll need, but it’s better than nothing.

    7. Artemesia*

      We could get cash advances for travel but not a credit card; they just didn’t hand out corporate cards to very many people. We could get a cash advance and then provide the receipts to erase it. Usually the cash advance just covered part of the expenses but the heavy lifting like air tickets and hotel and the expense report would cover that and the rest and we would get further reimbursed for what had not been covered.

    8. Formerly Ella Vader*

      I’ve worked at several places where it was possible to request a travel advance, including where I work now. Sometimes this was done very straightforwardly – every time you filled out a permission-to-travel form, you put the estimated cost of the trip and how much cash/cheque advance you wanted. Other places, I had to ask about whether it would be allowed and the admin wasn’t quite sure how it worked, making it clear that most people who travel don’t use it.

      I think that as a senior person, you would be doing junior/less-flush employees a big favour if you inquired about travel advances and how they work, and advocating for them to be a thing if they aren’t, and then letting the new people all know about them. If they say “oh no I’ll just put it on my credit card” say no, take the advance, put it into your credit account right away, then you won’t worry about running out of credit or about the reimbursement not coming before your bill is due.

      If your employers are unwilling to do travel advances at all, then offering to book someone’s flights with your own, to share the airport limos and taxis, and to make their hotel reservation would be much less embarrassing to me than me having to confess that I couldn’t book it yet because I had to wait til payday.

      Another reason for businesses (and for you, if you’re trying to do the right thing and your company won’t) to offer travel advances is because an unaccustomed trip for a new employee will mean other extra costs that they won’t get back. New clothes. Luggage or briefcase that doesn’t scream “student tourist”. Petsitting and childcare (if your company covers these things, make sure your protegees know it.) If the per diem amount is expected to include tipping (hotel cleaners, taxi drivers, food and beverage) remind them. If they are going to incur extra cell phone charges because of the trip, or if there are extra costs for hotel internet or hotel parking, find out what they have to do to get them paid.

    9. NaoNao*

      When I was a junior (and to some extent still, depending on the costs) I literally didn’t have enough of a credit limit to charge a week in a hotel + a flight + meals etc. I’ve gone on work trips where the flight was $1000 and the hotel takes a “hold” of the cost of the rooms, meaning that I can’t use that money on that card either. So let’s say I have a $2000 limit. The hotel is $600 total. Generally they also ask for an incidentals charge, so now we’re at $1800 or even more. For someone running on a small salary, that’s a big ask.

      The idea is solid for a junior who has a high credit limit or doesn’t use cc’s to “stretch” between paychecks but I don’t think it’s the bridge between charging the stuff to paying it off that’s the core issue.

  3. nnn*

    For #5, if you’re eating the meal in the restaurant together, you could just grab the cheque and, if pressed, say “Senior employee pays – that’s how we do things!” As though it’s a tradition or etiquette that’s particular to you company.

    For hotel rooms, who’s booking the travel? Can you book the travel so it’s on your card as a matter of course, and, when you check in, say “Both rooms are on this card” as though its, like, an administrative matter? (I’m not 100% sure if it works the way I think it does though)

    Another thing that might smooth things over is to emphasize how you like getting the extra points. This is very much a “read the room” situation, but sometimes, with some interpersonal dynamics, you can come across as they’re actually doing you a favour by letting you pay for them and get all the points.

    1. MK*

      But it isn’t tradition or etiquette for the senior employee to pay or for the hotel to be put into their card, and the junior employees are going to find that out at some point.

      Frankly, this sounds like a problem with the OP’s perception of the situation,not anyone else making them feel bad. It would be much better to make it clear that this is normal and nothing to be ashamed about, than trying to handle the junior employee’s feelings for them.

      1. Zelda*

        “But it isn’t tradition or etiquette for the senior employee to pay”

        It is everywhere that I’ve been in a position to incur business expenses– an admittedly limited list. So I’m not going to try to claim that it is The Standard, but it certainly is an existing custom, with a number of sensible reasons behind it. So the LW might do well to flag it as how their department does things rather than as How Things Are Done, but it’s a perfectly fine thing to do.

        I agree that I’m very sorry the LW ever felt embarrassed about not covering business expenses out of their personal finances; there’s no earthly reason they should have, and whatever circumstance in their life made them feel that way was pretty unfair to them.

        1. AcademiaNut*

          On the other hand, I’ve never worked at a place where the senior employees automatically covered the junior employees when on business travel, and trying to claim someone else’s expenses on your report would probably cause considerable confusion, unless things were pre-arranged (like one person putting the AirBnB on their card).

          Honestly, I think the OP trying to make up reasons for why they’re paying a junior’s tab is likely to cause confusion, particularly as some juniors are paying with their own credit card, while some aren’t. Just be matter of fact and reasonably discreet about the process, and be mindful of the logistics of the process (like having to check in at the hotel at the same time).

        2. MK*

          But it isn’t how their department does things, that’s what I meant. In this company everyone pays their own expenses and are reimbursed.

        3. Lunch Ghost*

          They could say “Someone did this for me when I was junior, just passing it on”– that’s the truth, and still hits the “Don’t be embarrassed, you’re not the only one to ever be in this position” notes.

          1. ReallyBadPerson*

            This. When I was a 20-something employee, I used to sweat bullets until that reimbursement check came through. I would have kissed the feet of a senior employee who put my expenses on their card!

        4. Hillary*

          It’s usually a rule that the most senior person pays – there’s a potential for ethics violations if if the approver is sitting at the table. The senior person can order an expensive bottle of wine, have the junior person expense it, and then approve the reimbursement.

      2. octopodes*

        I think another problem with this wording is that it could be easily misinterpreted to the senior employee treating the junior employee with their own money, rather than with money that will later be reimbursed, which could introduce more discomfort to the situation, rather than alleviating it.

      3. Nerfmobile*

        My company has an explicit policy that for a shared meal at a restaurant, the higher ranking person picks up the check and expenses it. Turns out that can sometimes lead to budget abuses across divisions in some situations, so for large groups there is an asterisk that it is the highest ranking person _of the sponsoring team_. That is, a manager’s team can’t go out for a meal, invite a director from another division, and then stick the director with the check.

    2. SemiAnon*

      For hotels, generally they want you to book and pay on the same card, and I wouldn’t count on anything else going smoothly. You can book someone else a hotel room on your card, but they’ll want the card holder there when checking in (learned that one the hard way – room was on my roommate’s card, I arrived six hours earlier, and had to hang around waiting for her instead of getting the sleep I desperately needed).

      1. Nancy*

        Was your name also on the reservation? Hotels don’t care whose name is on the card, but do care about the names on the reservation. So if other people are staying in the room and may check in earlier, call and have them listed in the reservation.

        1. SemiAnon*

          We told them when we made the booking, including the fact that I’d be arriving earlier, but knew nothing about it when I arrived.

        2. Koalafied*

          I’ve been able to check in before the person who paid for the reservation as long as my name was also on the reservation AND I was willing to put down a credit card for incidentals upon check-in. They could switch the incidentals to my friend’s card once the friend arrived, but they wouldn’t allow a room to be checked in without having a credit card on file.

      2. Anon all day*

        My company booked a hotel for me, so my name wasn’t on the credit card, and they just had to fax an authorization form to the hotel confirming that the booking was for me/I could sign anything needed for check in etc.

      3. ToTiredToThink*

        All of the times that I’ve stayed in a hotel where it was a different card paying, I’ve never had to have the original card on hand to check-in. I’ve had a number of situations where I was like the employee in this story. Once, it wasn’t even work related – a family member died and a friend decided to cover my hotel room at the airport. I’ve even used Pay-in-4 virtual credit cards (where a physical card doesn’t exist) to pay for a hotel.

        In your instance I have a feeling it’s because the reservation was in your roommate’s name – not because the physical card wasn’t there.

    3. Cambridge Comma*

      That’s setting the employee up for an uncomfortable situation if they ever have dinner with another senior employee who expects everyone to be paying for themselves.
      In some contexts I would also think the points thing would start to seem a little dodgy. Perhaps the junior employee would start to wish they had their own points.

      1. Falling Diphthong*

        Yeah, I could definitely see a junior who isn’t struggling to come out of any debt viewing this as “OP grabbing the points by insisting that the senior pays, which isn’t actually a rule.”

        Present it as an option, not a fait accompli.

      2. Irish Teacher*

        Yeah, I definitely wouldn’t do the “senior employee pays; that’s how we do things here” because then they will assume that’s true whenever they are with a senior employee and if another doesn’t, it could potentially make things very awkward.

    4. Kate*

      I think that’s weird phrasing. It makes it sound like the senior employee is treating them, rather than getting the expense reimbursed.

      I mostly agree with Alison’s last point – I think most people are going to have less feelings about this than OP did (I’ve personally never had a problem saying ‘I can’t upfront this expense’ and getting the company invoiced or getting a senior to pay – it’s just business), and these complicated responses are just making more of a big deal about it. You’re doing it because that’s the way the company does things.

    5. mikey c*

      Places I’ve worked the general deal is that the senior employee has a company credit card and they always pay for everything for everyone there. if the senior employee’s not around (taxi to the station, breakfast snack…) then sure, the junior can pay and expense it, but as a rule _everything_ done with the senior present is paid for with their company card.

      1. WellRed*

        This. Even when everyone has a card, it’s not unusual for the most senior to pick up the tab, whether it be dinner, drinks or cab fare.

    6. Forgot my name again*

      For my SO’s work, that *is* how they do things, company policy. Most senior person pays and claims back expenses so that junior employees don’t have to worry. Maybe suggest it to this company?

      I personally feel that not being able to afford things isn’t in any way shameful, so I feel like OP should try and reframe this in their mind, because not every person who can’t afford to pay is going to feel the same way. OP, it was a long time before I could start paying for things myself, but where I work there are plenty of people in both camps such that there’s a social sense of paying forward about it all. Please don’t feel embarrassed about being at that stage of life – I promise you, the majority of us have been there.

      1. SemiAnon*

        The problem is you’d be requiring the senior person to pay for everyone on their personal credit card. I’d bet that most of the situations where the senior person pays, the senior person has an actual corporate card, and is not fronting their personal money for it. The OP doesn’t have a corporate card, and it sounds like no-one else does either.

    7. Asenath*

      The problem with grabbing the cheque at the restaurant, and I speak from experience here, is that if the very junior person is new, they can go through agonies of uncertainty about paying, wondering if they can order just a bowl of soup because that’s what they can afford, or would that look really odd. It would have made things so much easier if whoever organized it said “The whole team is going out to dinner on the Thursday, 7:00 PM at Chez Marie on Nearby Street. Senior Manager will cover all the cost.” Presumably Senior Manager then claimed the cost back, but at the time, all I could think of is what I could possibly afford to order, since I didn’t know Senior Manager would say at then end of the dinner that she’d be covering all the junior’s dinners. Or, sometimes, the restaurant staff would tell us it was covered.

    8. KRM*

      On my last trip with friends I booked the hotel rooms and just said “all the rooms go on X card” because it was easier for us to split the expenses after. So for sure a senior employee could book all the rooms, put more junior employees names on the room, and they can say “when Guacamole Bob checks in, the room is on this card”. And if no senior employees are going, I think you could still do that–when I went for a grad school interview, I checked into the hotel and it had already been covered by the school, and I didn’t have to do anything at all. They even covered all expenses so I didn’t have to put a card down for extras, which may not be the case with OPs company, but it’s worth clarifying that as a policy.

    9. Person from the Resume*

      No because then the senoir employee pays for everyone at the table and not just the person they are fronting expenses for. Plus what if the LW isn’t the senior employee at the table? Is he putting the expense on the most senior employee or is he paying for the senior employee too?

      And then the LW files his travel voucher and has to work out that I paid for my hotel room and meals, and Junior Guy’s hotel room and meals, and at this one meal I paid for all 5 employee’s meals? Getting more complicated than needed.

    10. Shhhh*

      My thought was emphasize the points thing, too. I mean, definitely along with Alison’s advice. But I’m incredibly motivated by rewards programs :). I’m currently sitting on over 70,000 Skymiles with Delta.

    11. Artemesia*

      Where I worked we could not get reimbursed on travel for multiple people on the same check. It was possible when wining and dining people interviewing for a job — that was a special category. But on a business trip only our own expenses could be on a dining check. Each person needed to pay and be reimbursed for their own. Meals though are seldom the budget breaker — it is the tickets and hotel that are really tough for juniors to pay.

    12. LittleMarshmallow*

      I agree to be matter-of-fact about it. Another thing that I think helps is if you remind the person that ultimately “company” is actually paying. You’re just doing the expense report (I get that when you have to use personal funds and get reimbursed it’s a little weirder but ultimately if your company doesn’t have issues with reimbursement then it shouldn’t need to be “a thing”). We have corp cards but when we travel together usually most senior pays for meals… if you’re basically equal we take turns. It’s silly to make restaurant staff split a bill when ultimately the money is all coming from the same place.

      When I travel with friends we often book hotel under one credit card and then split later. It’s just easier. Not work related, but still, ultimately LW (and other junior employees) weren’t being paid for by the senior people, they were still being paid for by the company just through senior person.

  4. Rich*

    OP5, I have traveled extensively for work, and I have been on both sides of your situation in my career. Alison’s advice is good.

    I’ve found it’s best to bring it up with them when scheduling the trip. “We’ll be in Saskatoon next Tuesday, staying at the ThusAndSuch hotel. If you need me to handle the flight or hotel charges for the trip, let me know so we can keep everything running smoothly for you”.

    Also, in general, pick up the charge for meals you eat together. Everywhere I’ve worked has always had either a policy or informal practice of the senior person at the table paying for a meal, and expensing it, listing all attendees. This takes away both the anxiety reimbursement, a lot of the expense tracking overhead, and frankly generally just makes the meal more enjoyable for the more junior folks.

    If you’re thoughtful, proactive, and matter of fact, you’re doing everything you should. But also, it’s good to remember that it is, in fact, not a big deal — it just felt like one to you when you were on the “receiving” end of it. It may be helpful to come right out and say that. “When I first started, it was challenging to absorb all the charges and cash flow issues associated with travel, and it really stressed me out. If you’re fine with it, that’s great. But I want to save you the anxiety I went through, so I’m happy to help if it’s helpful.”

    1. Willis*

      Yeah, one person always pays for dinner when we travel. It’s less work on keeping track of expenses and also less annoying for the restaurant than having to do a bunch of checks for one table.

      1. NotRealAnonForThis*

        A sign of how awful our travel system was at OldJob: we couldn’t cover our work-mates tabs on a single bill like this. It was flagged as being “charge amount greater than allowed for meal, and/or disallowed additional meals” even when we input them with our actual names. Flagged expenses could not be submitted until rectified. We learned the first time how many hoops we had to go through to get them pushed through, then just apologized and asked for separate checks from then on.

    2. mikey c*

      yes 1 person paying for meals also means the person with less cash doesn’t feel like they have to scrimp and not order what they want, so it’s good for promoting equality/team spirit/etc

    3. hbc*

      One nitpicky tweak that I’ve found works well in general: change “need” to “want.” So many people won’t want to admit to needing help with finances or an extra hand or whatever, but are okay with saying that they will accept it.

      -“Do you need me to pay for the hotel?” “No, I can make it work, no need.”

      -“Do you want me to pay for the hotel?” “Well, that would make things easier, if you’re sure….”

      1. Emilia Bedelia*

        Honestly, I would feel exactly the opposite – I would never admit to “wanting” someone to do something as I wouldn’t want to look entitled, but if it were an actual need I would accept help. I’d feel better if the person could see that I had a good reason to ask for help, and wasn’t just asking because I didn’t feel like doing my own expense reports or something.

        All this to say, I think it can definitely be a touchy subject, and different people are going to bring different baggage to the table. As long as the OP has a positive attitude and can conveys that this isn’t an inconvenience, it’s a totally normal thing to do, I think their colleagues will understand the sentiment. Tone will mean more than specific words in this scenario.

        1. pancakes*

          Yes, for a number of people “want” is not a much less fraught word than “need.” It might even be more so, if they have a history with trying to stifle their wants in favor of their needs.

      2. pancakes*

        I’d think a number of people inclined to over-think things — which seems to be a lot of people — would then be wondering whether they qualify as “needing” the expense covered up front. Better to somehow make clear that it’s a routine business expense, and avoid any suggestion that the employee’s own financial condition is somehow relevant to how it’s handled. “What we do with company travel is put this on a senior employee’s card,” or something.

    4. Storm in a teacup*

      Yes our workplace has this policy – if multiple staff paying for something eg meal or hotel – the most senior person pays and adds the others.
      Op5 may be worth suggesting to your company if they’re open to these kind of suggestions

  5. ThatInvisibleDragon*

    OP2. My boss also asked me about my Ukrainian family first, once when I all first started and then again a week or two later when I was cancelling my PTO (I was planning to go back to Ukraine in April). I was worried about similar things so made sure to emphasize that the relatives that stayed are safe far away from any fighting. But honestly I think you’re fine, they asked first and the updates are rare enough that aside from the content they’re no different from any other major event/change in your life.
    I was also worried about putting a flag in my Slack profile but aside one of the new guys asking if I was from Ukraine no one said a word even though it’s kind of a perpetual reminder.

    1. Slava Ukraini*

      OP2 and ThatInvisibleDragon,
      I hope that your relatives are safe and well. My personal idea about sharing with my bosses things about my life are heavily dependent on that boss and how much trust I have in them. However, I also believe that something as large as a war negates those parameters. And saying something every 4-6 weeks is not oversharing. You are allowed to be people who have worries that might spill into work. Most people will be sympathetic and willing to help you out, especially for something this important. My workplace has offered support to Ukrainian employees and their families.
      And having a Ukraine flag in Slack as a perpetual reminder is fine as well to me. Some people perhaps need that reminder of what other people are going through at any one moment in order to remember to be kinder.
      Slava Ukraini! Heroyam Slava!

    2. tiasa*

      hard agree that having family members facing war or in combat zones is a big life event that absolutely is not oversharing to mention on a 4-6 week basis. OP, you don’t say what country you’re working in, but if you’re in the US, there’s a widespread and strong (sometimes too strong!) cultural value for ‘be a little extra nice to American soldiers and their families out of respect for their sacrifices and their service’ and given the context, I’d be hard-pressed to imagine a workplace scenario where that would not extend to the family members of Ukranian soldiers and volunteers as well.

  6. Raida*

    5. Covering travel expenses for junior employees

    I would tell Junior staff that the process is “if you prefer not to” and ‘just want to clarify’ that the business is responsible for these costs and is not entitled or interested in the reason why the Senior’s card is used. If it’s a personal preference, being burnt with reimbursements at other jobs, not having a credit card, it is none of [business] business and [business] has made it very straightforward to go with the Senior’s card, [example].
    and add “I’ve previously had staff give me their justifications for asking to use my card, like personal finances, so I just want to be clear that it is unnecessary. You just let me know what needs the company card used and that’s what we’ll do.”

    1. bamcheeks*

      Depending on how junior the junior employee is, it might also be useful to make this part of a wider conversation about how expenses work, what you can and can’t expense, how long your company usually takes to reimburse, and any particular expectations at your particular company. There’s often a lot of assumed background knowledge about how expenses work that is neither obvious nor universal.

      1. KRM*

        This! Every company has a different expense policy, and often has several layers which take things like “has their own corporate card” or “prefers to book their own travel” or “can cut check before travel to cover majority of expenses” built in. Onboarding should include a rundown of how expenses work and what you can expense, especially if you’re expected to travel. Some companies require receipts for everything, but also have a system where you can upload the receipt using an app and it gets paid out right away (next check/end of week/whatever company policy is). Some give a per diem and leave it at that. But it should be covered when you’re hired, with a “always feel free to reach out to X contacts if you have questions before you book/travel/submit!”

      2. BethDH*

        This would have made a huge difference to me. I remember being told things like “oh, you can get reimbursed for a taxi” but I didn’t know you could ask the taxi driver for a receipt so I would take the bus or walk ridiculous distances at unsafe times.

      3. UKDancer*

        Definitely. When I have a new person start (especially if they’re at the start of their career) I always make sure I or someone else explains to them what the rules are for booking travel and how expenses work in the company. I find it helps to be as matter of fact as possible and not make assumptions what people can afford so everyone gets the same explanation of how to get a travel advance if they need and what sort of things we cover and what we don’t (to be honest the key thing is that the company won’t reimburse for alcohol). Also the importance of keeping all receipts.

        1. bamcheeks*

          The mindset shift when you realise that £300-worth of receipts you’re carrying around is actually the same as £300 cash to you is something else.

      4. Agile Phalanges*

        Ooh, this is a good point. Especially for folks who have been at the company a while without needing to travel and now have a trip coming up. I was lucky enough to have gotten my start in Accounts Payable, where we processed expense reports (first by paper, later with an online system), so I actually knew all the travel rules (had literally written the company guidelines) and how to get reimbursed and how soon it would be, but I can see where someone else would not. And it’s easy to be a person that normally doesn’t need to travel, but now they’re sending you to this one training, or a particular conference, or whatever, so it’s a one-off thing but no one thinks to tell you all the rules and procedures.

    2. eat_more_bees*

      As somebody who has definitely been in a situation where everybody is talking about going and doing stuff that I absolutely cannot afford as a work event, I agree with LW5 that it is very embarrassing to have to admit that I can’t afford to participate. Especially if you are from a different socio-economic group than most of your coworkers, who may not have EVER been in the position you are in (moving from working-class into office jobs was a VERY big change for me).

      This is a very good idea to offer the help in a way that isn’t directly embarrassing to the employee in question, or require them to disclose anything about their financial situation. It doesn’t matter if nobody should be embarrassed or judged about only having enough to barely cover their rent, some people will be, and some people will judge or not understand.

  7. Donna*

    There is always someone with a corporate card who can cover the weight of your expenses.

    1. Zelda*

      The letter says “I know you’ll say we need company credit cards, but that’s not possible (or rather not in my control),” so no, there is not someone with a corporate card.

    2. Raboot*

      OP does not need help fronting expenses.
      That’s actually the opposite of their question.

    3. The Other Dawn*

      No, there isn’t. Out of the five companies I’ve worked for, only one had corporate cards and they were for executive management only.

      1. lost academic*

        This, plus, at many places where significant fraud has occurred they’ve been removed or are heavily monitored and only for very specific purposes – you typically see that in the public sector but I’ve seen cases with smaller private sector companies. Plus honestly… I’ve had company credit cards and it’s just a credit card in my name for business expenses so…. it’s not anything different then carrying the charges on my personal card. The agreement you sign when you open it makes that clear.

  8. GythaOgden*

    With the Ukraine situation, definitely keep people in the loop. First of all, it helps people know that you have an issue that might cause you to be distracted at points. My Russian colleague has friends in Ukraine and everyone is being supportive of her. (The worry for her is that she’d be the victim of ignorance about the situation, but it seems like apart from being very worried about speaking Russian in public, which is frustrating because I’m learning it and she was the only person I could practice with, she’s being well supported by her team. Everyone understands it’s Putin who did this, not Russia.) Secondly, your bosses are human beings too and they will want to help you out. My bosses knew that I was struggling with my husband having cancer and then dying, and they bent over backwards to help out. My line manager suffered from a similar anxiety disorder to what I do, and even before hubby’s decline was on the radar helped out by disclosing his issue to me and telling me that he would back me up if I needed help.

    Knowing is half the battle. If people understand why you’re worried and stressed, they can help you a lot more than if you don’t tell them. In situations where there’s an obvious cause, it’s probably easier to get them to understand — I’ve been through both an inexplicable mental breakdown and one or two with an obvious cause, and the ones with directly relatable causes were easier for people to handle, not because the others weren’t as bad, but because we naturally tend to be more sympathetic to things that are obvious life-or-death stressors rather than things which you think people should be able to compartmentalise while at work.

    And please accept my thoughts (and prayers if you’ll take them) for your sibling and any other friends and family out there. It’s a terrible, terrible thing to be happening, particularly when you’re on the other side of the world. Any decent human being would understand if you needed time and space to handle this.

    1. PotsPansTeapots*

      I agree. You’re not oversharing with your boss by bringing it up once a month or less. Most decent bosses want to know what’s going on with employees because they’re good people, but also because it provides context should something happen.

      If it makes it easier for you, you may also be doing a kindness for your co-workers and other people in your boss’ life who have friends or family in Ukraine by giving him the odd update.

      And all the best to your family.

  9. All Outrage, All The Time*

    OP5: I have seen this a lot in my career and it’s not a big deal. Maybe just say “I have a company card and I can put your expenses on that, or you can use your personal card to get points or what have you.” It’s normal for not everyone to have a corporate card so just be matter of fact and let them know they can choose to do it either way. You don’t have to reference their personal finances or the fact that they are junior at all.

    1. LizardOfOdds*

      This. Status in the company should not matter when it comes to expenses like this, and I think positioning it as a Junior/Senior thing is strange (at least it would be in my industry). I think the offer can still be made without asserting seniority.

  10. Luna*

    LW1 – If you ‘have’ to go there, it’s not a perk. It’s almost like a work-function.

    1. it's-a-me*

      They meant that they had no choice of where to go, not that they have no choice about going at all.

    2. I'm Just Here For The Cats!*

      This isn’t a work function. It sounds like its just a fun perk that if they choose to go on vacation in this specific area of Florida they can use that airbnb. No where in the letter does the LW say they are being forced to go. Its just that the timing is limited and they have to use their airline tickets or else they are out of the money.

      1. Phony Genius*

        I agree that they are not being forced to go. However, if your boss offers you this type of perk (especially if he owns the business), it can feel like it’s mandatory. I would wonder if the boss would feel insulted if I didn’t accept the offer. If it feels like a “mandatory perk,” I wouldn’t enjoy it.

      2. Becca*

        I get the impression that OP feels pressured to use it though. She says the boss says she “needs” to choose a new week and asks how to let the manager know she doesn’t want to try again.

  11. Jules the First*

    For OP5, if you’re senior, you could speak up and ask corporate to consider a policy that takes the load off junior staff – a corporate policy where you book hotels and plane tickets, for example, or clearly state that the most senior traveller picks up the bills. In the moment, one of my senior partners does this very gracefully by checking in ahead of his juniors and telling the concierge to put the charges “for the whole group” on his card, so that when juniors give theirs it is only for incidentals. This only works where the company has booked the hotel, but it’s a start. I usually offer my PA to help with travel arrangements “so she can put all the costs on one card to keep expenses straightforward.”

    1. fueled by coffee*

      This! We (a university) don’t have a great reimbursement culture, but they will at least book flights on the department credit card so we aren’t out hundreds of dollars several months prior to traveling (and getting reimbursed).

  12. Green great dragon*

    #4 I would check whether you actually have a written dress code, and suggest it’s updated if necessary.

    1. Lunch Ghost*

      That’s what I was thinking. Which isn’t to say if it’s out of date and doesn’t get immediately updated, I wouldn’t talk to the interns, I just wouldn’t use the “giving official permission” language. I’d say it more the way my boss at my last job did when she told me about the outdated dress code. “You’ll notice the dress code says you can’t wear A, B, and C, but honestly, a bunch of us have been wearing those for years and no one’s ever said anything.”

      1. OP*

        OP here! I just looked through all the emails HR sent me when I first started as well as the employee portal and it doesn’t look like we have any company-wide policy and based on prior conversations with my department head – it seems like it’s up to their discretion. I really like your wording because there’s nothing concrete I can point to but I know no one is going to say anything either. I also liked the other commenter’s suggestions of being detailed on the specifics of what’s OK and what’s not OK so I’ll incorporate that as well. Thank you!!

        1. Just a thought*

          Our dress code is essentially, you should be dressed appropriately for your duties and remember that you represent our organization when you are out in the community. That’s pretty much it.

          So, for instance, I have been wearing jeans almost daily since returning to the office, but if I have outside vendors coming in, I throw on the slacks.

    2. anonymous73*

      There are many places that have written dress codes that specifically say “no jeans” yet have casual days when you can wear jeans, so there’s no guarantee that this will be helpful. After OP addresses the interns about the relaxed dress code, they also need to talk to the co-worker who told them not to wear jeans because frankly it’s none of their business.

      1. Jora Malli*

        I’ve never worked anywhere that didn’t have the casual day schedule included in the written dress code. Usually it will be the standard dress code first and then “Casual days are Friday, Saturday and Sunday, here are the parameters of what casual clothing is acceptable to wear on those days.” Is that not a thing most companies do?

        1. anonymous73*

          I’ve never seen a company handbook specifying “casual” days. IME Most of the time modifications to the standard dress code are season or activity based. Sometimes it’s for a fundraiser (pay $1 to wear jeans each Friday, money goes to charity), etc.

    3. Just Your Everyday Crone*

      Also, with interns, I’d suggest erring on the side of more details on all aspects of the dress code. “Ok to wear jeans” is a broad statement and younger people might not realize that their shredded jeans are a bad idea.

    4. INFJedi*

      Regarding #4 I do wonder: since when is wearing jeans looked as “dress-down” or only seen as casual?

      Sure, jeans (or any trousers) hanging halfway someone’s bum is not something I consider as appropriate at a workplace, same with clothes that are “fashionable ripped”. I also understand that some firms (think lawyer firm, perhaps even some accounting firms) have a specific dress-code.

      But when the dress-code is “clean and reasonable presentable”, I think a nice jeans is just fine. Not?

      1. Sparkly Librarian*

        Traditionally, jeans are not formal enough to wear to an office. Denim used to be primarily worn for heavy labor, and although they’ve been a fashionable choice for decades now, professional dress codes do not include them. “Dress down” days assume that most of the time a business dress code (without jeans) is being observed.

        Business dress code: suit (matching trousers and jacket, with a collared button-down dress shirt and tie; matching skirt and jacket, with a formal blouse or shell)
        Business casual: Dress pants with collared shirt or blouse; knee-length skirt in dressy fabric; shift dress with sweater or blazer; ties optional; workplaces on the more casual end could include khaki trousers
        Casual (for work): clean unripped jeans may be worn; khakis; maxi skirts but not mini skirts; T-shirts may be allowed but could be restricted (for example, “no graphic tees”)

        Many modern workplaces do exceed even this level of casual — yoga pants, hoodie sweatshirts, ripped jeans, or pajama pants are acceptable in some environments, although individuals may prefer a step dressier. If the dress code really is as generic as “clean and reasonably presentable”, I think sticking to “casual for work” guidelines would match that. In that case, there wouldn’t need to be a “dress down” option.

      2. TrixieBelle*

        “Since when” is probably the wrong framing – they used to be much more glaringly out of place in some casual workplaces and now aren’t.

        Fifteen years ago, when I started work at the company I work for still (office with some audio visual production that occasionally requires manual labor), nobody wore jeans to work unless they were literally doing carpentry, moving things, doing dirty work, etc. Jeans were not “nice” office casual clothing and the big boss would get annoyed at seeing violations of these rules.

        Today that is no longer the case. It started maybe 12 years ago with jean-cut twill pants in different colors, or solid dark denim in conservative cuts that didn’t read as “blue jeans” and nobody (or hardly anybody!) was fussy enough to try and complain about those. Soon nobody cared about “athletic shoes” either, which was also a prohibition.

        Now with the old big boss retired and gone, it seems crazy that they were ever that fussy. But I’m sure there are other workplaces at different stages in a comparable evolution.

      3. TrainerGirl*

        Since folks started coming back into the office after pandemic remote work, there doesn’t seem to be a clear consensus. I just started a job that’s 100% remote, but my last job had a business casual dress code, and when we went back to the office, the general feeling was, “If you make me come in to the office, I’ll wear what I like.” The higher ups didn’t seem inclined to comment on it.

  13. Princess Deviant*

    Ah, the interns dress code.
    I’d love to know what happened to that bunch of interns who pushed back against the dress code and got fired – where are they now?

  14. Turtle Duck*

    Sometimes I think people have horrible bosses to have such views on life and work…Being professional is a thing and it is important of course, but it doesn’t mean you aren’t human. If having relatives in a warzone makes you less employable…wow, maybe you shouldn’t be employed there. I know people can’t just up and leave any job, but if there isn’t any reason to think it affects you in any way, why stress about something like that on top of being in a stressful situation already? I would make it my career’s aim not to work in an environment where I have to think about things like that. I have already cried in front of different managers – obviously not all the time and excessively in an awkward way, but things happen, we are human, and most other (decent) humans get that.

    1. Emmy Noether*

      I’m with you! Most bosses are humans, not monsters, and have some compassion. A boss who is going to let someone go on the pure theory (not even actual observation!) that they may be less concentrated due to family in a war zone (!) is a monster.

      My workplace actually gave people with family in Ukraine extra PTO and resources towards the beginning of the war, and would surely still do so on request for an urgent need now. I think that kind of thing pays off in employee loyalty (I sure have positive feelings about it, even though it doesn’t apply to me).

      1. EPLawyer*

        See how the company treats others when something out of the ordinary happens, lets you know that if something happens with you, you will be treated the same way. Maybe not relatives in a war zone, but your family across the company suffering a natural disaster (heaven forbid). You know you will be treated with compassion.

        A little humanity goes a long way.

        OP your friend is wrong. You have not overshared. Oversharing would be all you talk about all day every day in exquisite detail. An update every few weeks while the situation is ongoing is fine.

    2. Not So NewReader*

      Yep. I am not sure that OP’s friend is that helpful. When extraordinary things happen, it’s human nature to talk about it. And it’s human nature for others to be concerned. I am not clear on why your friend does not “get” this.
      But it seems like your boss is okay with this. The boss’ opinion matters, your friend’s opinion, not so much.

      Just my opinion but a wise boss wants to have some idea about how their employee is doing so they know where to cut some slack, such as letting the employee leave early or whatever. This is how to retain good employees, have some awareness of what’s going on and where they might need extra support.

      I hope your sib is able to stay safe.

      1. drinking Mello Yello*

        Some people are Weirdly Private about anything extraordinary happening in their lives and expect other people to be the same way. Or maybe it was a stint in a crappy job where the employees were expected to be Perfect Working Machines with No Problems Ever to slow down the pace of Work. Who knows.

        Regardless, yeah, I’m with you and everybody else on most halfway decent bosses understand that sometimes Shit Just Happens.

        I also hope your sibling stays safe, OP2.

      2. Expelliarmus*

        I wonder if OP’s friend read some other AAM (or AAM-like) advice that said to be careful about sharing personal info, and they’re applying it to way more situations than it should be applied.

        1. I Wrote This in the Bathroom*

          Or they are new to the country and base their advice on their experiences in other countries that have (even) less labor laws and protections than the US does? All of the harebrained advice I’ve received on the job was from my fellow immigrants. And I get it. Back in Home Country, I was at one point working as a contractor, was offered a FT position one day and then had the offer yanked on the spot because I disclosed to my manager that I was five months pregnant. This was totally legal and normal in Home Country at the time – there were no labor laws to speak of, a job ad asking for candidates “no older than 35” or “men only” or “an attractive woman age 18-25” was a normal thing that shocked no one (first two would typically be for IT jobs, last one for an admin job). Then people leave there, come here, and assume that the workplace policies will be the same, except maybe stricter because there’s more money being involved. And that assumption is extremely wrong.

    3. metadata minion*

      Agree, agree, agree. I’ve been through several major life things at my current job, and my supervisors have almost across the board been awesome about it. A decent human being will want to help someone who’s struggling rather than penalize them for it, and even a stereotypical soulless capitalist boss would be shooting themself in the foot if they fired someone for going through a rough spot. An excellent employee who gets help and support during a difficult time will likely be loyal, and will almost certainly go back to being an excellent employee after the rough spot is over.

      There is certainly a point at which giving constant updates on what you’re going through becomes oversharing, but LW, every 4-6 weeks or so sounds absolutely reasonable to me.

      1. Irish Teacher*

        Absolutely. I had thyroid cancer two and a half years ago. At the time, I was not yet permanent in my job and had to go through another interview the following summer to become permanent. I got nothing but support from all those in authority. The deputy principal (who I only told that I had to have surgery) told me, “the job comes a long way down the line after your health” and the head of my department told me if I wanted a day off, to just text her and they could just cover the classes within the department.

        When I went for my re-interview the following summer, the principal asked if I were OK to come back, given that this was the first covid lockdown and once I assured her that my doctor had said I was at no particular risk, that was the end of that. If “I am recovering from cancer” didn’t discourage my boss from giving me a permanent contract, I don’t think “I have a sibling in Ukraine” would.

        I think some people get a bit caught up in worst case scenarios or take the advice about not making yourself too vulnerable in front of your boss a bit too literally. It might be oversharing if somebody told their boss “I’m so worried about my sibling in Ukraine that I haven’t been sleeping and I’ve an appointment with my doctor and I’m hoping he’ll give me a perscription for sleeping tablets, because I really can’t go on like this. My head’s all over the place and I can’t concentrate on anything because I keep imagining the worst case scenario and when I do sleep, I get nightmares about what might be happening to them” and certainly in a new job, it would probably be best not to go into that level of detail, although it would depend on the boss and the relationship one has with them, but just giving the facts and letting them know it’s stressful for you seems perfectly reasonable to me.

    4. anonymous73*

      100% We’ve been seeing a lot of bad advice from friends of LWs lately. Not everything is black and white. I have some managers in my past who I’ve shared personal things with and others where I was more tight lipped because I didn’t trust them. While there are certain things you shouldn’t ever do outside of the RAREST of circumstances (like telling your manager you’re job searching), most times it’s about trusting your gut and adapting in the situation. But yes, we are human and outside life things are going to affect our work sometimes, and if my manager is someone who’s going to hold that against me, I’d be looking for a new job ASAP.

      1. BethDH*

        I think early in your career it’s common to extrapolate from one experience — and we sometimes punish the people who don’t catch on to unspoken rules from one example too.
        There’s definitely a learning curve about what level of personal detail is appropriate at work and part of what you learn is that it isn’t a blanket rule and how to navigate that.

        1. nona*

          Or they’re only seeing TikTok (or Reels or facebook whatevers) advice snippets that make blanket statements instead of getting into the nuance of the various considerations.

        2. fueled by coffee*

          I also think we’re reading an advice column where people write in with *problems* they are having at work, so unreasonable bosses tend to be overrepresented. There’s some selection bias happening here.

          1. Don Joe*

            I think so too. No one is going to write in to AAM just to say everything is great unless it’s like for an update.

    5. I Wrote This in the Bathroom*

      Came to say that OP’s friend is being overly cautious, and is describing a (hopefully fictional) management of a company that I would advise anyone to avoid working for. When I was starting my career in the US as a new immigrant, with my only prior work experience being from my home country, I sometimes received unhelpful advice like that; basically boiling down to “if you don’t pretend hard enough that you are a robot with no personal life or needs whatsoever, you will lose your job/tank your career”. 25 years and six corporate jobs later, can confirm that this is blatantly untrue.

      OP, my sons’ family on their father’s side is in Ukraine. I loved that family when they were my in-laws and miss them terribly. They are safe at this time, but it is nerve-racking even in a situation like mine when they are not really close relatives. ANYONE can understand and empathize with how it must feel to have a sibling in a hot zone there. You did not overshare. Either way, I am sure it is better for your boss to know that you are stressed and distracted for a very serious and valid reason, than to think that you are acting stressed and distracted for no reason that he knows of.

  15. I'd Rather Be Eating Dumplings*

    Re #4: definitely confirm with your boss before talking to the interns. It’s possible that the dress code has relaxed de facto but as people start coming back in there are plans to tighten it up again.

    Also if possible (depends on the company, I suppose) there might be a benefit to just a brief ‘heads up’ on the dress code change in a meeting or email?

    Interns tend to get a lot of feedback from many different people and ideally they wouldn’t be in a position where they’re getting conflicting instructions from different staff….and definitely they don’t want to be in a position where they think they’re clear to do something but other teams or staff are viewing them as not participating in the culture or not following rules.

    1. GythaOgden*

      Yup. There was definitely a point where my boss asked me to go back into black shoes rather than coloured trainers; she gave me a dispensation for my healed broken ankle but I needed to get black trainers. (Not too expensive after the £150 I spent on the proper running shoes that properly supported my feet, and smart-comfortable enough that I can wear them to anything else that requires more formal shoes).

      I would say that there’s been no bright line on what we can do/not do at reception on very slow/empty days (like today) but it’s a matter of reading the room carefully and being able to pivot. I was allowed to do something, then I kinda sorta got away with it if there was literally no-one in reception, then it became a bit difficult to sustain with a straight face with more people coming in, at which point I took the sketchbooks and airpods home and accepted playtime was over. It’s annoying, given that even on busier in-office days reception is not called on for very much and there’s none of the ‘coachloads’ coming in for meetings like in the Before Times, but it’s also not a hill I want to die on.

    2. WellRed*

      Yes to your entire 3rd graph. The biggest problem is the coworker who had no standing to say anything.

      1. Dawn*

        From my read of the situation, the coworker told them exactly what the dress code says – which if they’re doing orientation/training is literally their job.

        This wasn’t a case of misinformation. The interns were being given the facts as written.

      2. I'd Rather Be Eating Dumplings*

        I think that’s why there’s value in updating staff if the dress code has really changed. The nature of internships is often that many people will proactively offer feedback, even if they’re not formally managing them.

        1. Dawn*

          For sure, but I’d also wonder in this case if this isn’t expected to be a permanent change. Like, staff are being given allowances NOW that may or may not persist when we’re further out from everyone working from home.

  16. Gnome*

    Op 5

    Consider that the bigger expenses – hotels, taxis, flights, etc. -ay feel different from the smaller more public ones (restaurant bill). Part of this may be because of how publicly the smaller ones show up. But those are also easier for people to cover. So people might be ok picking up their meals, for instance. So as Alison said, pay attention to cues.

    It’s not unusual for one person to book a group of rooms, but it could also be a kindness if the person who did NOT book has something to do during check-in, even if it’s just checking the fliers for local eateries in the lobby.

    Also, things like not eating as a group, getting hotels with a continental breakfast, or having a group stop at a local grocery store can reduce out of pocket costs. When eating as a group, you can cover the tab “to make it easier on the servers” as compared to separate checks.

  17. Irish Teacher*

    LW2, I think it would be kinda weird NOT to mention it to somebody you are working closely with if you have a sibling in Ukraine. I think if your boss found that out later, he’d wonder why you’d made no mention of it, as it’s kind of a big issue at the moment. One of my colleagues is married to a guy from Poland and she mentions stuff like his mother is near the Ukrainian border, so they are trying to convince her to come and stay with them because they are afraid things will spill over. Not mentioning it would seem to me like you were deliberately keeping it from people for some reason, which would seem a bit odd.

    Perhaps it’s different where you are, but certainly here in Ireland, Ukraine was a regular topic of conversation earlier in the year. When their prime minister addressed the Dáil (our parliament) via video link, somebody turned on the TV in the staffroom so we could watch it (I…hadn’t even known that was a real TV. I thought it was just a screen for announcements or something or that it was broken as this was the only time I ever saw it used; a couple of my colleagues said if they knew it actually worked, they’d have put it on for big sporting events!!), we got lists of Ukrainian phrases when we had some Ukrainian students joining the school, the parents of our Ukrainian students came in and made Ukrainian food for the staff, etc. I think it would be a bit odd if during any of the conversations, somebody avoided mentioning “oh, my sibling is out there.”

    Not that anybody is obliged to give any information about their personal lives, but…I’d certainly expect a “why didn’t you TELL us?” if somebody found out later and hadn’t been told.

    1. Jellyfish*

      While I don’t think OP2 overshared at all, I can see where the friend is coming from. I’ve had a boss who loved an excuse to gossip about their employees, a boss who maliciously used any scrap of personal information against people, and a couple bosses who weren’t vindictive but still negatively swayed by any sentiment that wasn’t, “I love this job and am 100% committed to it and nothing else!!!”

      While the friend’s framing is pretty dramatic, sometimes there’s a significant gulf between how a good supervisor should act and what real ones do. If the friend recently got screwed at work or saw someone else harmed because they shared personal information, the warning makes sense. My current boss is great and would probably be very supportive of any major personal struggles, but I’m not ever planning to find out for sure. Once burned (or four times….), twice shy.

    2. I Wrote This in the Bathroom*

      Not that anybody is obliged to give any information about their personal lives, but…I’d certainly expect a “why didn’t you TELL us?” if somebody found out later and hadn’t been told.

      Can confirm, I once had my work teammates be mad/upset at me because I’d gone through a major life event (divorce) without saying a word to them. They were hurt when they found out. Their reaction was exactly like you describe – they felt I’d deliberately kept it from them. Mind you, I kept my manager and the HR/legal in the loop, for reasons of paperwork, PTO etc. I’m in the US, Northeast Midwest. People certainly still are aware of and worry about the war, even if they no longer follow it closely.

  18. FashionablyEvil*

    #3–I’m also in favor of not disclosing since you haven’t even applied to grad school yet, but I do work in a field (contract research) where it would be very normal to share your grad school plans pretty soon upon joining and no one would think anything of it. (We do generally hope to get 2-3 years before folks head off to school, but sometimes it’s only a year and that’s just part of how it goes.)

    All that to say that knowing your field can help you decide when to share your plans about grad school.

    1. Charlotte Lucas*

      Yeah, I worked in retail while in college & while making my grad school plans. It was a part-time job, & nobody thought twice about it when I took time off to take the GRE, etc. Because unless you were management, you didn’t expect to be there forever.

      But I wouldn’t bring up plans over a year in the future in my job interview.

    2. Womblin*

      I agree, but it could be worthwhile asking a general question on benefits and finding out if the company offers any tuition reimbursement…I think if they do it could also be an indicator of how likely they are to support your continuing education while keeping you employed. That’s not to say companies with no tuition reimbursement won’t support you, but if they do…I’d feel a bit more confident.

    3. Alan*

      My daughter was in this position and kept it vague. “I’m thinking of applying to grad school at some point.” They were disappointed when they found out that she had actually applied, been accepted, and was leaving, they tried to get her to keep working, but she left with no hard feelings. A lot of employers value education. They get it. I can’t imagine turning down an otherwise good employee who might leave for grad school because (A) that ambition might actually make them a better employee, and (B) people’s plans change all the time. They might decide not to go, or we might hire someone else who left without warning.

  19. Doctors Whom*

    #5, my first instinct is to tell you to check in with whomever is responsible for travel expenses & reimbursements at the company to see how it needs to work if you were to cover some part of expenses for a junior employee. (Where I work we travel on per diem – if I want to pick up a meal for someone else I have to then claim actual expenses for each meal that day instead of the daily rate AND the person I pick up for needs to know not to claim per diem for the associated meal.) We also have the ability to cash advance travel expenses and this helps keep all the expenses aligned to the individual human – with sufficient notice, our financial teams prefer this so that they don’t have to deal with verifying expenses across multiple expense reports. And, it’s private. Only the traveler, finance team, and the admin know about it. So before you do anything, I’d learn how it needs to work to figure out what might be best to offer.

  20. I should really pick a name*

    LW #5
    At the end of the day, you can’t change how someone feels.
    The approach that Alison suggests is a good one, but some people just have it in their heads that having someone else pay for something is shameful, and there’s only so much you can do to change their minds.

    It is a work expense. It is entirely reasonable if you’re not able to cover it yourself.

    1. River Otter*

      Yes. You can be matter of fact, but the truth is that how someone feels is mostly about their own take on a situation and not about what you say. Take for example, yourself. Your bosses and seniors were matter-of-fact and did nothing to imply that you were somehow deficient for not being able to afford to front the expenses, but you still felt terrible about it due to your own beliefs about The situation. Just be as matter of fact as possible and be kind to yourself regarding any possible lens that a junior employee places on your words.

  21. anonymous73*

    #1 Be matter of fact and direct. Just because they’re your bosses doesn’t mean you can’t stand up for yourself. In addition to what Alison’s suggests, I’d also question why they’re forcing you to change your time line when you booked your trip before the other employee. And if they won’t cover you in another hotel, just tell them that you won’t be able to use it because of the financial burden. And I would start looking for new job. People make mistakes, but when they make THEIR problem into YOUR problem, that tells you everything you need to know about how they feel about you.

    I rented a beach house from a cousin once, and he wrote the date down wrong and ended up overlapping the last day of another family’s week with the first day of our week. So he arranged for us to stay in another house for the first night because it was his fault. Yes I know it’s family, but THAT is how you handle a mistake.

    1. ceiswyn*

      The reason the OP is being forced to change is that the other guests aren’t employees, they’re paying customers.

      Admittedly the OP’s boss doesn’t actually say that’s the reason, but the setup seems to be that the property is an AirB&B rental, it’s just that employees can rent it for free. So it seems very likely that the OP’s boss would rather disadvantage an employee for free than disadvantage a paying guest and lose income.

        1. ceiswyn*

          It certainly doesn’t change the fact that the owner sucks and OP needs to look for another job (if they aren’t already). But since there’s no evidence that this is a ‘one employee vs another employee’ situation, but almost certainly an ’employee vs paying customer’ one, I don’t think there’s anything for the OP to gain by questioning why they’re the one being displaced, and it will just distract from the key message of ‘you are causing me to lose $$$, how are you going to put this right?’

      1. kiki*

        Yes, but I think a conscientious and decent person should realize that prioritizing the other group isn’t actually free, it’s that the cost right now is being paid by LW and their group. If this is a small business, I feel like it’s possible the owners aren’t putting together that offering this perk to employees means the expectations are higher for prioritizing your employees’ experience, even if they get a more lucrative offer from another customer.

        1. ceiswyn*

          I agree, and the OP needs to concentrate on getting that across rather than asking why they’re being bumped.

    2. Hiring Mgr*

      Ideally yes, but considering the owner is a struggling/failing business and that this has already happened once before this, AND as others have said it’s likely because they found a paying customer, I doubt they will be handling it as you suggest

  22. sb51*

    LW#5 if you’re worried about it being awkward to offer for junior people, another thing to mention is that “some people like this because they earn points, and some people would just rather not deal with getting reimbursed”, which can let the junior people feel like you’re both doing each other a favor — you’re letting them avoid any issue with low credit limits (or whatever) and they’re letting you earn the points.

    Also, be super clear about what the company will/won’t reimburse for in any cases where they’ll be putting it on their own card. I remember the first grad-school conference I went to, where I didn’t sign up for the pricey banquet because it was well over the $ allowed for dinner, and then my advisor and everyone asked why I wasn’t going that evening, and when I explained they were startled because that was a “conference function” and of course it would be reimbursed. (And the only reason I was even able to swing the hotel/plane ticket was that I had the privilege to have parents able to get that kind of credit limit and a good relationship with my parents such that I had a joint card while I was a student for just these sorts of issues.)

    1. BethDH*

      That mention of the conference dinner you didn’t attend brought back so many memories of my own experience. I did exactly the same thing.

    2. fueled by coffee*

      *Stares in faculty members who (pre-Covid) required us to attend dinners and happy hours and would then insist on splitting the check evenly*

      *also stares in my department not reimbursing us for conference registration fees until we’d returned from the conference, even though they need to be paid months in advance*

      *also stared in needing my parents to co-sign on an apartment for me because my credit score dropped from having too many travel-related expenses on it relative to my credit limit*

      I will say that my department is very good about letting us use the department credit card for booking flights, but oof, even split 4 ways, hotel rooms in New York and San Francisco and Toronto are pricey.

  23. Pocket Mouse*

    #1 – The restaurant owner and his wife (or, the restaurant business and the AirBnB business) are separate entities, and I think that’s being glossed over a bit. There are two scenarios: One, the restaurant’s owner and the owner’s wife do not have a communicative, mutually respectful partnership as they each run their own business, the owner’s wife disregards promises made at the owner’s business, and the owner cannot or does not advocate effectively for you and other restaurant staff in his wife’s endeavors. Two, the owner and the owner’s wife have jointly agreed that paying customers for the rental supersede any promises made to you and plans you have made accordingly. In the first scenario, the owner may be convinced to reimburse your expenses for the flights or alternate lodging. In the second, not gonna happen. They just don’t care about your plans or their own integrity enough.

    Either way, this is not a perk you can count on, unless and until restaurant employees are able to book the rental through AirBnB with a 100% discount code. Whether or not the restaurant owner sets you right, you have standing to push for this method based on your experiences to date.

    1. Alan*

      My experience with AirBnB (and the reason that I will never again book with them) is that the owner can still opt out with no penalty. We were left hanging when we booked an AirBnB for a college graduation, where there was very little lodging available. The owner simply waited until shortly before the graduation and then cancelled. We had no recourse. AirBnB was not helpful, and the owner just encouraged us to book with them another time. This and other issues mean that AirBnB is dead to me.

  24. ABCYaBye*

    LW1 – The one other thing you could ask for, beyond what Alison has suggested, is that the owner pay the fees for changing your tickets. That’s not a perfect solution by any means, but it might be something that is actually going to happen. I fear that you won’t get the costs for elsewhere or the cost of the tickets reimbursed to you, so this might be the “least” they can do.

    1. kiki*

      Yes, unfortunately I’m getting a sense the owners will be resistant to refunding you the full amount (even though I think they should have offered to do so already). I’d ask for the full amount, but keep this in your back pocket to ask if they aren’t willing to fully refund you.

      I’m sorry you’re in this situation. A work perk should never become something that ends up costing employees

  25. BeenThatDoneThere*

    I know it sucks for #1, but I don’t think you can really ask for the owner to reimburse you for your tickets or put you up elsewhere. It’s not fair, but I look at this like traveling space available if you’re an airline employee. Sometimes you get stuck, and in some cases, you have to eat tickets yourself when the stars align badly.

    Put yourself in the owner’s shoes. You offer a substantial perk to your employees (that you have NO obligation to) whatsoever. Yes, they made a (bad) mistake, and the NICE thing would for them to offer to make it right, but asking for it would seem to be inappropriate. And you’re not really “out” money. You can STILL go on that vacation; you would just need to pay for lodging like you normally would on ANY vacation.

    In effect, you are asking for them to lose money so you can take a vacation that any normal person would have to pay for anyway. If I was an employer and somebody said this to me (even though it was my mistake), I would be offended and most certainly would never offer them this ($1000+) perk again. It’s really not fair to ask them to lose money to subsidize your vacation when they were trying to do something nice for you in the first place.

    My recommendation is to eat it, have your friends chip in and get a place in Florida. If you’re not willing to do that, eat the cost of the voucher conversion.

    1. Lab Boss*

      OP1 *is* out money, though. At minimum they’re out the cost of lodgings, and they may even be facing a situation where if they couldn’t stay in that house they’d never have booked the rest of the trip- like if there’s no other lodging they can afford that’s in the same area as what they planned to do.

      Something presented by a boss as an official work perk is never just a “favor” or “something nice.” It’s a calculated move to improve employee morale/retention, and that’s true even if it seems extremely generous or isn’t a standard form of compensation like salary or PTO. In the case of free rides on airlines, the terms and conditions are spelled out well in advance. Presenting something as a guaranteed perk and then withdrawing it after the employee has made other financial commitments is terrible move.

      1. GammaGirl1908*

        Also, I expect that LW1 might have chosen to go elsewhere if these lodgings had not been offered. That is, they talked the friend group into going to Florida at this discount, but if they had been going to pay full price, they would have preferred Acapulco or Jamaica three weeks earlier AND gone for cheaper. They very well could end up paying full price for a trip that no one would have chosen. Budgets make a lot of our choices for us.

    2. Pocket Mouse*

      I see what you’re saying, but I disagree. The offer of a free stay has been made part of the promised conditions of employment in management at the restaurant. Therefore, the restaurant owner should make sure it, or something comparable, is available just like any other promised benefit of such employment. The certain thing is that employees should never be out money in an attempt to access a benefit that they can’t actually access due to an issue that arises (intentionally or not) on the part of the party administering the benefit.

    3. ceiswyn*

      The OP is going to have to either lose money changing the flights, pay for the flights but not go on holiday, or (if even possible) pay a lot for accommodation elsewhere. By any standard, they are ‘out’ money.

      Nor is there any indication that the perk only exists if paying customers aren’t using it; it would be useless if it were, given that it’s so far away and the OP would in that case be unable to make plans more than a few days out.

      If the worst case is that the owner is offended that the OP actually wants to *use* the perk they’ve been offered, and refuses to offer the OP the opportunity to get their holiday cancelled at short notice ever again, that’s… not much of a worst case.

      1. BeenThatDoneThere*

        The “worst case” is that the OP will burn ALL the capital she/he has with the owner. Like I said, the “nice” think for the boss to do would be to pay. But this sounds like a small business owner who owns the restaurant and the AirBnB. Asking them to lose (literally) thousands of dollars by either paying for the airfare or paying for other lodgings (especially when they have said the OP can use the property at a later time) is not realistic for a small business owner.

        I could see *maybe* asking the owner to eat the cost of the rebooking fee. But that will still burn capital. I guess it depends on how long the OP will be at the job, or whether she/he cares about it. This “perk” (as poorly managed as it is) is likely worth thousands of dollars (I just booked a week in Florida for over $2k). I *guarantee* that the OP will never be offered this $2k perk again, if she/he asks the owner to lose thousands of dollars to subsidize the OP’s vacation. If I was the owner, and the employee asked that, I would be very unhappy, and (let’s be honest) would look at the employee in a different (and negative) light going forward.

        The OP can certainly “ask” for these things (especially to be reimbursed or to split the rebooking fee), but doing so will likely cost more in the long run, both in terms of career opportunities and the inability to ever use this “perk” again.

        The question is “is it worth it?” If I was the OP? My answer would be “no”, and I’d eat the change fee myself and book the house for another time.

        1. ceiswyn*

          If it is not realistic for the owner to lose literally thousands of dollars by paying for their own error, it is doubly unrealistic to expect the OP to lose that money to pay for someone else’s error.

          A ‘perk’ that is costing the OP money in order to *not be able to use it* is not a perk. And if the owner is unwilling to make right any part of the inconvenience and expense that their error has caused to their employee, then the light in which they view the OP is rather less relevant than the fact that they have poor management ability and poor principles, and the OP should get out as soon as they practically can.

        2. ceiswyn*

          (And the OP has already booked the house for another time once, so how many times should they ‘eat’ the fees and inconvenience?)

        3. Paris Geller*

          asking them to lose (literally) thousands of dollars by either paying for the airfare or paying for other lodgings (especially when they have said the OP can use the property at a later time) is not realistic for a small business owner.

          I can’t say I have any sympathy for this small business owner. If it’s unrealistic for them to lose thousands of dollars because they run a small business, it’s even MORE unrealistic for that owner to put the cost on the EMPLOYEE. The owner offered the perk. They have an ethical obligation to make things right. It’s not the OP’s fault the owner is apparently bad at being an AirBNB host since they can’t even prevent against a double booking.

        4. Pocket Mouse*

          Are you really more concerned about a small business’ finances than and actual, living human being’s finances? Especially when the small business effectively offered to put their (potential) money toward a purpose then reneged, and an actual human being made plans based on that promise? This is such a weird take that you have me wondering if you’re the restaurant owner’s wife.

          1. WellRed*

            We have no idea whether or not the Airbnb is doing poorly like the restaurant. Zero. Zip.

          2. BeenThatDoneThere*

            Again, I understand the employee’s position. Absolutely. This sucks for everyone involved, especially her/him. But the average franchised restaurant owner makes $100k per year. These folks are usually not “rolling in dough”. This isn’t Apple we’re talking about.

            I feel for the OP. But in the real world? Going to a “mom and pop” who own a small business, and asking them to eat thousands of dollars to (in effect) to effectively subsidize an employee’s vacation (which would be the case to ask them to pay for other lodging) will DEFINITELY alienate them. And (in the real world) that will come back to haunt the employee.

            And even in the case that the *employee* can make a case that the owner has an obligation to *her*, there is no way in the world that the owners should have to pay a dime for the OP’s friends. You can’t expect them to pay for the vacation of *somebody they don’t even know*. When you book a free anything, there are some risks you simply accept. AGain, imagine the OP was an airline employee using “buddy passes” for her friends and they all get bumped off the flight. That’s what happens sometimes, and it would be beyond ridiculous to think the airline would pay for *their* tickets on another carrier.

            That’s why I asked about how much the OP cares about the job. If she doesn’t CARE about harming her career there (if it sucks, she may not), then it can’t hurt to ask. The owners may pay for the tickets, and the OP leaves before it can come back on her. If she *does* care about the job, then the question is whether her future with the company is worth eating the tickets.

            Again, the question isn’t just about what’s “right”, but what’s *practical*. This was definitely a screw-up by the owner’s wife. No questions at all. And the OP got the short end. The question is whether it is worth the inevitable blowback and damage to the relationship (even thought it is undeserved) of trying to get the owner to pay out of pocket.

            1. pancakes*

              Anyone who would feel “alienated” by their own guest in their rental property simply asking them to consider covering the cost of their own mistake in having double-booked it is worth alienating. That’s a weird and misplaced sense of entitlement. The owner isn’t entitled to be as unreliable as that without consequences. And people don’t have to be “rolling in dough” to be responsible for their own actions. This is someone who owns a second home. If they can’t afford to reimburse people who’ve arranged to spend time there when they double-book it, they need to become careful about not doing that.

              When airlines over-book planes, they do have to compensate the passengers they bump. The amount of money those passengers are eligible for varies; it looks like it’s $1350 for Americans and $700 for Europeans.

            2. Just Another Zebra*

              When an employer offers an employee a perk, it should never result to the detriment of the employee. Full stop. Because of mismanagement, OP1 is out money and time. You’re so concerned about how the boss might perceive OP… but think of how OP is perceiving their boss! Think of how the rest of the management team is perceiving the boss! This person already asked them to change their booking once, and is now asking them to do it again – at the OP’s loss, mind you, while the boss gains the rental rate from the new renters (who booked after OP). This whole situation seems off.

            3. Paris Geller*

              But the average franchised restaurant owner makes $100k per year. These folks are usually not “rolling in dough”

              . . . SO? I’m guessing the OP makes a lot less than the owner, and now they’re out the money. You can say they would be out the money anyway if they paid for their own vacation that they planned, but there’s a good possibility they wouldn’t have planned this trip and be willing to spend SOME money if the accommodation was not there.

              1. Pocket Mouse*

                They evidently had enough dough to spend on a second property in the middle of a truly wild purchasing landscape, so they had some to roll around in. If they did not have enough dough to do that *and* offer time in that property to restaurant staff, then they should not have offered time in that property to restaurant staff.

                BeenThatDoneThere, your head’s in the wrong space and I find it baffling that you can only seem to see the owner’s POV, but not even with the full scope of what the owner independently *decided* and *promised* to staff— you’re making it seem like OP is asking the owner to pay for a vacation out of the blue, and that is just so not the case. Party A made a commitment under zero duress, and when Party B made plans based on that commitment, Party A reneged and Party B is left with a significant monetary loss. Party A is responsible. Party A might be terrible people and not make it right with Party B, but Party B will have done nothing wrong to point out the harm and ask that it be made right.

            4. Very Social*

              But the average franchised restaurant owner makes $100k per year.

              Are you… implying that’s a small amount of money? And suggesting the OP makes more than that?

            5. biobotb*

              It’s so weird that you’re so worried about someone you think is making $100k per year spending a couple hundred or ~$1K to make their mistake right with an employee, but brushing off the employee’s concerns about having an unexpected several hundred dollar expense. Do you think the employee is making more than the business owner?

            6. Betsy Devore, Girl Sleuth*

              “Going to a “mom and pop” who own a small business, and asking them to eat thousands of dollars to (in effect) to effectively subsidize an employee’s vacation (which would be the case to ask them to pay for other lodging) will DEFINITELY alienate them. And (in the real world) that will come back to haunt the employee.”

              *It was the owners’ idea.* They said “As a perk, we’re letting you spend a week in our timeshare, free.” “Okay; I usually take a stay-cation or go to my friend’s place in Long Island, but I’ve never been to Florida!” OP would not have booked the tickets if her employer hadn’t given her reason to think she would be using them.

              This is giving me childhood flashbacks to my dad saying “No, I said I’d play chess with you *if* there was nothing good on TV.” Truth being, he’d forgotten he’d even promised me. But in this case, it’s not even the principle, it’s the money of the thing. As someone said upthread, if OP had known at the start that she would have to give way to any paying guests, she very likely would have declined the privilege, and saved the money and aggravation.

        5. bamcheeks*

          I *guarantee* that the OP will never be offered this $2k perk again, if she/he asks the owner to lose thousands of dollars to subsidize the OP’s vacation

          This is really terribly entitled! Nobody forced the manager to offer it as a perk. And by describing it as a “perk”, they suggested it was part of the employee’s compensation. It is not reasonable to withdraw that *after* the employee has booked flights, and it is not reasonable to look askance at the employee for not wanting to absorb the cost of their poor organisation.

          A manager who offers a “perk” to their employee is not doing them a favour as a friend: it is automatically part of the business relationship. I am sure the manager was quite happy for the employee to regard it as a part of their compensation and hoped that it would be a factor in their employee choosing to remain with the company. If you want the upside of offering a perk as a company owner, you need to actually handle the downside professionally as well.

        6. Emmy Noether*

          I think you’re comparing the wrong situations. Let’s look at it from another angle. If the airbnb had not been double booked, then OP would have paid X$ for airfare for a vacation. Boss would have neither gotten nor spent money.
          Boss: 0$,
          OP: -X$

          Now, boss presumably has paying guests. He is getting Y$. Employee has the choice of either paying X$ for no vacation, or paying approximately X+Y$* total to get other accomodations. So employee is out either X or Y, and boss actually GAINED Y$ compared to the other situation.
          Boss: +Y$,
          OP: -X$ or -(X+Y)$

          To make it right, boss should pay those Y$ towards an alternative accomodation. In which case boss is back to 0$ (not out anything), and employee is back to paying X$ total. This would put everyone back into the financial situation of the deal in the first place.
          Boss: 0$,
          OP: -X$

          Your point of view only works if “boss gets income from airbnb each week” is the baseline you’re comparing the situations to. But then he shouldn’t have offered this perk, because it was always going to mean he was “losing out” on money. The baseline has to be the OP getting their offered perk as planned.

          *I realize it may be hard to get anything for Y$ this late. That may change the total calculus, but not the fact the the boss is gaining money here.

    4. kiki*

      You offer a substantial perk to your employees (that you have NO obligation to) whatsoever. Yes, they made a (bad) mistake, and the NICE thing would for them to offer to make it right, but asking for it would seem to be inappropriate. And you’re not really “out” money. You can STILL go on that vacation; you would just need to pay for lodging like you normally would on ANY vacation.

      I see what you’re saying here and I think this is probably how the owners are thinking about it, but when a business owner makes something a perk of employment, there’s a higher obligation to ensure the employee doesn’t lose money if they accept that perk. And the LW is really “out” the money. It sounds like they couldn’t afford to take that vacation if not for the free lodging and now their money is eaten up by airline vouchers they’re unlikely to use.

    5. frame*

      „If I was an employer and somebody said this to me (even though it was my mistake), I would be offended and most certainly would never offer them this ($1000+) perk again. It’s really not fair to ask them to lose money“

      i sincerely hope you’re never an employer because this is a terrible analysis. will you also be offended when someone requests PTO or a raise?

      1. The New Wanderer*

        How is it okay for the employer to ‘ask’ the employee to lose money instead? “Yeah, we promised you could stay for free but now that you’ve committed financially, we’ve changed the deal.”

        In a similar situation – we arrived to find our rental was double-booked, and the very apologetic owners paid for a replacement rental for us. That’s part of the cost of doing business: if the business makes a mistake it eats the cost, it doesn’t deny responsibility or pass the cost along to the customer (if they want to retain positive ratings/continued business, that is!).

        1. hamburke*

          My family – parents, siblings and their families – rented a beach house a few years ago. My sister arrived first to find out that the house has been sold to new owners and reservations hadn’t be cancelled but weren’t being honored. My brother-in-law called the real estate agent listed on the sign, and before we arrived 4 hours later, our party was put up in another house that had a cancellation (ended up being one we stayed in before and would have picked if it had been available when we booked).

          But it does give me anxiety even though it was made right – we’re planning another family trip in a few weeks and I’m not looking forward to being the first there.

      2. Lab Boss*

        Telling OP to accept the first screwing-over because complaining about it might further anger their boss, is like saying OP should be happy to work for Darth Vader: “I have altered the terms of the deal. Pray I do not alter it further.”

    6. I Wrote This in the Bathroom*

      “I would be offended and most certainly would never offer them this ($1000+) perk again.”

      Then it’s a good thing that OP (and probably OP’s coworkers who’ve also already been burned) do not want to use this perk again. This way they won’t be in an awkward position having to explain why they are turning down the quasi-perk.

      “And you’re not really “out” money. You can STILL go on that vacation; you would just need to pay for lodging like you normally would on ANY vacation.”

      I somehow have a suspicion that OP wouldn’t have booked a vacation in that location on their own, if it hadn’t been tied to this perk. BG: stupidly bought a timeshare in 2001; tried using it with then-husband and 2 kids; found out that, out of their advertised “thousands of properties worldwide”, the ones that we could book with the amount of points we had, were all actually scattered around Florida, all in places we wouldn’t have visited otherwise (e.g., we were thinking Miami and were instead offered North Hollywood). The properties turned out to be rundown and badly maintained, my husband didn’t get any sleep at the last one we stayed because the ancient carpet in the room triggered his allergies, etc. The “perk” that we’d bought for our family to have better vacation options, turned out to be a burden and an obligation to go on a crappy vacation every other year so as not to lose the points. I was lucky to sell it, for less than 10% of what we’d bought it for, just before the 2008 crash.

    7. Just Another Zebra*

      I’m sorry, but this is terrible advice. A company I work with offers perks to their customers, one of which is a rental home in Myrtle Beach. My family booked a week vacation using this perk, paid for plane tickets, dinner reservations, the works. Got a call 3 days prior to leaving and was told the place was double booked. They found us another place to stay and covered the cost, paid for some of our airfare (I think 25%) and issued a Visa gift card for $200 to cover a nice dinner out on them. They made a mistake, and they corrected it. If these owners don’t make OP whole in some way, that says a lot about them. None of it good.

      1. MEH Squared*

        Agreed. And the doubling down from the OP on this thread makes it even worse. The boss/boss’s wife offered a ‘perk’ that they have rescinded without so much as a ‘sorry’. And the boss did it twice, which indicates to me that they’re putting paying customers before the restaurant employees. Which, fine if they explicitly said it ahead of time–but it doesn’t seem they have.

        If the owners can’t afford to eat the costs of a cancel THAT THEY DID TWICE, then they should not offer it as a perk.

        1. biobotb*

          Plus the perk isn’t even just rescinded–the OP will be worse off than if they’d never tried to use the perk!

    8. Purple Cat*

      Wow, this really comes across as a “blame the victim” mentality.
      LW is absolutely out money. Let’s say she could only afford a $1,000 trip. Because the lodging was free, she booked a trip that required plane tickets. Now she has tickets to a place she can’t afford to stay, because her manager deliberately screwed her over. If a true business had double-booked her, they would make it right on their own dime. That’s what the manager should be doing.

    9. pancakes*

      Eh? This isn’t “the stars aligning badly”; this is a business owner who double-books their second home in order to maximize the money they make from it, with apparently no regard for the plans their employees make (and the money they spend) in reliance on the schedule the home owner gave them.

    10. HBJ*

      This isn’t the same at all. I’ve actually been in the airline employee situation and had to rearrange plans. As an airline employee, you know up front that the tickets are subject to space available. You are going standby. The airline does not guarantee you a seat on your chosen flight.

      LW was promised space. If they were told up front “your reservation is subject to change if we get paying customers,” then that would be the same as the airline situation.

    11. biobotb*

      It’s inappropriate to ask that a perk actually be a perk? If the OP is out hundreds of dollars, then this isn’t a perk. And you’d be offended if someone asked you to correct a mistake you know you made?? Wow, just wow. But yeah, if you want your employees to shoulder your mistakes, then you shouldn’t offer “perks” that aren’t.

    12. Betsy Devore, Girl Sleuth*

      Seems to me that some (not all) employers, when they offer a perk, they’re really saying “You’re bound to have noticed that we pay you slightly less than our competitors for the same work. In order to keep you from leaving us for one of those competitors, we’re going to offer you a fabulous amenity! That you can’t get anywhere else! Of course, we either are or have ties to the people in charge of this amenity, which means it doesn’t take nearly as much out of us as paying competitive wages would, and that’s also the reason you can’t get it anywhere else. So take it and be happy, ‘k?”

      *If* the boss gets offended, they shouldn’t. It’s not as if OP #1 sidled up to the boss and dropped hints about the boss’s timeshare. Boss offered, OP accepted *in good faith*, and now she’s out hundreds of dollars for airline tickets she can’t use. I think she’d rather have the money and not have the vacation.

  26. Person from the Resume*

    I don’t talk about the situation all of the time, but my boss has asked about them a few times and when there is a major situation change, like leaving a combat zone or going back into a combat zone, I will mention it to him (probably once every 4-6 weeks).

    In this case your friend is wrong. Once every 4-6 weeks is not very often at all. It’s something that on your mind understandably. So frequency is not a problem. It could be too much if you spoke about it every day all the time. But you are not.

    It is personal / not work related, but we’re not automatons and we’re expected to be human and have human concerns. Mentioning this one very occassionally as you do is fine. There’s no reason for concerns about siblings in a war zone have to be off limits; although, yes there are some topics that should never should be discussed at work, but this isn’t one of them.

  27. Dawn*

    #4: From my read of the situation, the coworker told them exactly what the dress code says – which if they’re doing orientation/training is literally their job.

    This wasn’t a case of misinformation. The interns were being given the facts as written. Your coworker’s information might be colloquially out of date, but you probably shouldn’t be lambasting them for informing the interns correctly of company policy.

    1. Dawn*

      And who knows? They’re interns. It could well be that they’re going to be held to a different standard than senior employees.

  28. Erin*

    LW5: I had this same thing happen to me in the early days of my career. I had very little room on my credit card to assume expenses and then be reimbursed (and the process took a loooong time).

    My manager could tell that I was embarrassed to bring the money part up to him, and he very kindly offered to have me use his corporate card to book my travel/hotel/any up-front expenses. He also must have been lobbying for the corporate card situation to change in our company, because two things happened on/after that particular trip: other senior co-workers who were on the trip made it easy for me by just asking for the bill at restaurants and paying for the group & telling the junior employees to be sure to have any room charges/etc charged to them. Also, about 9 months later, the company revamped the corporate card policy to include everyone who travels or entertains.

    Please just be proactive about approaching junior associates with the costs of business travel. It made such a difference to not feel stressed for addressing a matter that nobody needs to be embarrassed about.

  29. Person from the Resume*

    LW4. I agree with Alison’s answer, but you should at least run it by your boss. Is the dress code actually relaxed or are some folks disregarding it? And if it is truly/officially relaxed then your coworker needs to be informed that he’s giving out incorrect information. If you don’t want to tell your coworker for some reason your boss can tell him.

  30. Emmy Noether*

    #5 Anecdote time:

    when I was a new grad student, bright-eyed and bushy-tailed, I got invited to present at a conference (awesome!), BUT I had to float the flights, the hotel, and the conference fee myself, and the university was notoriously slow to reimburse (less awesome).

    My supervisor must have seen my facial expression and gently and discreetly pulled me aside before the trip to ask if he could loan me some money. Now, I probably could have pulled it together with a loan from my parents, but it actually felt less embarassing to accept the money from him. I made darn sure to pay him back as soon as the reimbursement came through, and gave him a heartfelt thank you note and chocolates as (jokingly) “interest”. Still grateful to that guy and his kind heart!

  31. Madame X*

    It looks like the boss is prioritizing renters who will pay to stay at the Air BnB. I understand how they convinced their employees that a “free” AirBnB is a perk, but i don’t understand how this perk is a benefit is to the boss if they have not intention of honoring it.

  32. A*

    OP#2 – I recently finished a professional degree and plenty of classmates (myself included) didn’t disclose to their employer before a new job offer or even a promotion at a current job within the application cycle. Reasonable bosses were disappointed, but generally understanding about education and it didn’t burn any bridges. Less reasonable bosses were… not going to handle resignation well anyway.

  33. Veryanon*

    OP1: Something tells me that the vacation home will conveniently never be available no matter what dates you pick. It sucks, and hopefully you can get the owners to reimburse you at least some of the money you spent on air line tickets, but I think you have to chalk this one up to a lesson learned. Ugh.

  34. JayReal*

    OP2: Sometimes sharing can be helpful too. I had a very, very stressful personal situation going on in December into January and was constantly butting heads with my boss (for info he’s not a great boss, micromanages etc. but this was more then dealing with that). After a particularity bad day I pulled him aside the next morning, apologized and gave him the 100′ few of what I was going thru personally and that it was affecting me at work. Which it was, making a not good situation worse. He was very understanding and it helped clear the air a bit with us. He didn’t need the details just an over view (a very, very sick child and 5 family/friend deaths around Christmas).

  35. Student*

    OP #3: As AAM says, don’t disclose things now. Additionally, I want to make sure that if you do go to grad school, you look into whatever their rules are on freelancing/working during the grad school program. These rules vary wildly by profession and school and often by advisor.

    When I was in grad school, one of my fellow grad students was tutoring undergraduates on the side. His tutoring gig never interfered with our grad school studies or normal duties. However, our advisor (person in charge of our research and whether we graduate) overheard him chatting about tutoring one day. Our advisor immediately demanded he stop all tutoring. The advisor referenced a rule from our grad program that required grad students to get any outside employment signed off in writing from our advisor and the grad program’s higher-up administrators, and threatened to have this grad student removed from the program and yank his research funding if he didn’t comply.

    Not all grad programs work like this, but a lot of them expect you to devote most of your time to the program. Many of them, especially ones that come with funding and/or teaching responsibilities, will have mechanisms in place to try to block or limit you from outside work so they can monopolize your time. And, if you’re in the US, grad students are not fully protected by US labor laws – on some labor law issues, like unionization, eligibility fluctuates with whichever political group is in charge. On other issues, like minimum wage laws, overtime laws, and exempt vs non-exempt status, the Department of Labor just asserts that grad students don’t count. So, you have little to no recourse if you run into grad student program restrictions or exploitative labor expectations, other than hiding your side job from your advisor and hoping you don’t get caught, and finishing your degree as fast as possible.

  36. kittybutton*

    OP5, I would modify Alison’s language to not include reference to the person being junior. You could say “A lot of people prefer not to use their personal credit cards for work, but unfortunately, we do not have access to corporate cards. If you would prefer to book your travel on my card, just let me know, and I would be happy to do it.” You could even add “I do the same for a couple others on my team.”

  37. LegalEagle*

    OP2, my mom is in Ukraine now working in relief efforts and before she left I wasn’t sure if I’d share it with my boss and coworkers. But (as you know) having a family member in a war zone occupies a fair amount of your thoughts, so I ended up bringing it up in a check-in with my supervisor, and it’s come up once or twice since. I’m glad I ended up sharing, mostly because my team was really supportive, and it’s nice to have other people sending my mom good thoughts.

    Sending your sibling good thoughts now too!

  38. Connor*

    OP3 – You may find that the job is great and you could go to grad school online or part time AND the job might even have some reimbursement program you could take advantage of. I did an online MBA in 2 years while working full time and they covered 5k a year.

  39. MD*

    LW2, I have family in Ukraine and I actually struggled a lot, still do. My job requires concentration and careful decision making and, frankly, it just wasn’t there when my family were under constant missile strikes and even now it’s not that great.

    My boss was absolutely great – they arranged a large amount of compassionate leave and also adjusted my projects so that I would not be on a critical path for many things and could safely take a day off without affecting time-sensitive tasks. The latter adjustment, by the way, is something I wanted. In my current situation I felt that I risk letting my team down if things go wrong and I need to take time off on a short notice, or even just have a sleepless night because of the worry and end up struggling to finish something time-critical. I can see your friends generic worry around “they will not give you more responsibility if they think you cannot cope” but it is also important to be honest with everyone as to how much you can realistically cope with.

    It helped that I am in the UK where there are various protections and also that I was a consistently high performer before that happened. Still, even while on probation, as long as your boss seems reasonable I would recommend telling them. Things can go wrong and it’s better for them to have the context and understand that if you are distracted sometimes, you have an external reason for that, it’s not just carelessness.

    If you are actually doing well, this is awesome, I am so happy that it’s the case. But then you can be explicit about that, too, along the lines of “while I am under stress, I find that concentrating on work distracts me from my troubles and I am able to perform well, so I’d like to keep or increase my current responsibilities. Please let me know if you notice any problems so that we can discuss them”. That’s what I used in 2014 when my brother was in the war zone (and eventually injured and undergoing surgery). Everyone copes differently and good bosses will appreciate being direct with them about your life context and what you need from them to help you achieve best results at work.

  40. Raw Cookie Dough*

    OP#5, in addition to making the offer, you should also let these junior employees know that you also had expenses covered by a higher-up when you were in their position. This way, they’ll know it’s ‘generational’ and that would help erase any weirdness. It’s nice of you to be concerned about this.

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