should I send a Boss’s Day card to my new manager at a job I haven’t started yet?

A reader writes:

I recently accepted a new position at a different company that I’m very excited about. My start date is at the end of October, but I know that Boss’s Day is October 16. I was wondering if it would be appropriate to mail my new manager a card for the holiday.

Nooooo. Do not do that.

First of all, Boss’s Day is a ridiculous concept. (I have a whole column coming on Monday about this, in fact.)

Second, many, many, many managers agree that Boss’s Day is a ridiculous concept and really don’t want their employees doing anything to mark it.

Third, you don’t know your new manager well and can’t know if she falls in that camp or not. (Personally, if I got a Boss’s Day card in the mail from a new hire who hadn’t started yet, I’d be thinking, “oh crap, this person and I are not likely to be a good fit.”)

Fourth, it’s highly likely to come across as sucking up. You haven’t even worked for this person yet. And since she’s not your manager yet, you can’t really express appreciation to her for being a great boss, which means you’d just be marking the day in an impersonal way, and there’s even less reason to do that than if you worked for her.

So: no card.

{ 85 comments… read them below }

  1. Cynical Lackey*

    From Wikipedia “Patricia Bays Haroski registered “National Boss’ Day” with the U.S. Chamber of Commerce in 1958. She was working as a secretary for State Farm Insurance Company in Deerfield, Illinois, at the time and chose October 16, which was her father’s birthday. She was working for her father at the time. ”

    –Why is this even a thing in the 1st place?

    1. Charityb*

      Somebody felt guilty about blowing off Father’s Day and decided to make a whole lot of people’s lives slightly more complicated.

      (I don’t think this is the first letter to AAM involving Boss’s Day complications).

      1. Cambridge Comma*

        I (European countryhopper) had never heard of it before I started reading aam.
        Isn’t every day bosses’ day? It definitely is where Iwork.

      1. MashaKasha*

        Right? Can we replace all hallmark holidays with National Dog/Cat day number 1, 2, 3… and be done with it?

        This reminds me, WTH is sweetest day? I’ve never been able to figure this one out. Do I need to do anything on that day? does my SO need to do anything to me? What is the meaning of this ridiculousness? It’s next day after boss’s. I know that because I have a large calendar hanging on my cube wall right in front of my face right now. Otherwise I’d be oblivious to both.

        1. The OP*

          Sweetest Day (not sweeties day) is actually a really cool holiday that was turned into Valentines Day 2.
          It was created by Cleveland candy makers and it was a day to give candy to the poor, old, shut ins, and “invalids”.
          I donate candy every year to my dad’s nursing home. I had tried to get my work to donate candy to a local homeless shelter, but they had reserved all of the charity budget to Breast Cancer Awareness.

          1. Oryx*

            Are you from Northeast Ohio? Very few people know about the history of Sweetest Day unless you’re from this area :)

          2. Aunt Vixen*

            Huh – learn something every day. I’m from the Cleveland area myself and had no idea Sweetest Day wasn’t a thing all over the country to balance the calendar against Valentine’s day. (It doesn’t balance the candy distribution much, though, being so close to Halloween.)

          3. Muriel Heslop*

            We donate candy to our local homeless support group every October for Sweetest Day. We got our church on board, too. I love the origin and who doesn’t appreciate a sweet treat?

            1. Artemesia*

              I used to volunteer at a homeless shelter; lots of businesses give fatty, sugary foods to homeless shelters — we always had tons of cakes, pies, donuts, cookies, puddings (mostly day old stuff). Quite a few of the guys in the food line would refuse this stuff because they have trouble with tooth care and didn’t want to end up with rotten teeth — with no dentistry and difficulty keeping good oral hygiene on the street. It surprised me — with my sweet tooth an all — but candy may not be an unmitigated blessing.

          4. MashaKasha*

            Awww, that sounds much nicer than the Valentines Day 2 that it has indeed been turned into. I’ve seen ads for roses on sale for Sweetest Day several years in a row, so I just assumed it was the same thing.

      2. nep*

        All of these so-called holidays — ridiculous and contrived. I wish everyone would stop spending money keeping these stupid things alive. But hell — whatever. To each his own.
        Just — Ridiculous.

    2. NickelandDime*

      No one celebrates this. I think companies that do are probably not places you want to work.

      OP, your boss just wants you to show up on time, do great work, and make them look good. They want nothing else.

      1. Kelly L.*

        It’s on most of the calendars I’ve seen since then, usually called Patriot Day, and there are always a lot of remembrance-related things going on that day. It’s not a federal holiday (yet), but neither is Boss’s Day.

        1. Three Thousand*

          I just flipped back my desk calendar to check that. I don’t know how I never noticed it before.

        2. The _artist_formerly_known_as_Anon-2*

          Here in Massachusetts, we have a state holiday (not generally respected in the private sector) called Patriots (plural) Day -third Monday in April. It’s officially to celebrate the Battles of Concord and Lexington but until 2013 it was largely a holiday for public workers and an excuse to have a road race and a baseball game with an 11 am start. Of course, since the 2013 terror attack, it has become much more than a play-day.

          Rhode Island still celebrates August 14 – which, if you study your history – is the day the Japanese surrendered in 1945. It *was* called “V-J Day” but in deference to political correctness is now simply “Victory Day”. Some (not me – nor the general populace of Rhode Island) cry that the observance is offensive. It still will likely be celebrated, as long as World War 2 veterans are still living.

    3. hbc*

      “You coworkers aren’t appreciating my dad enough! He needs more recognition as the awesome boss he is. I mean, he hired me without any qualifications and gives me raises all the time. You guys all get the same, right?”

  2. A Bug!*

    Far as I’m concerned the only acceptable observance of Boss’s Day is in satire. “Happy Boss’s Day, sorry I didn’t get you a card”, to which your boss will laugh you with both roll your eyes at the ridiculousness of the concept.

    1. OfficePrincess*

      “Happy Boss’s Day. I got you a giant stack of reports to sign off on, with a side of bad news.”

  3. Snarkus Aurelius*

    Boss’s Day needs to go away permanently.  I don’t know why it ever started.  I don’t know what the purpose is.  I don’t know why some work environments make people participate in this.

    I do know this: gifts, if they are to flow in any direction in the workplace, flow down.  Never up.  Up is fraught with weirdness, liabilities, implications, and bad feelings.  (At my first job, this policy was outlined in HR materials, and I was so relieved when the holidays came.)

    The whole idea of people in positions of power being honored is ludicrous.  If employers want bosses honored, then it should come from on high and not down low where the pay is not as much.  There’s something disgusting about asking people who make less to contribute cash toward a person who makes more.

    1. Rebecca*

      I totally agree. One of my coworkers brought up Boss’s Day last week, and I said that gifts should flow downward in the workplace, not up, and I thought this made up holiday should go away, and wondered why or how it even got to be a thing in the first place. Her reaction? “What a terrible thing to say!” So, I’m out $4 because someone decided we’ll have food brought in for Boss’s Day. Ugh.

  4. Katie the Fed*

    I would be so incredibly weirded out if I 1) got a boss’s day card from anyone and 2) got a boss’s day card from someone who wasn’t working there yet. The very thought makes me painfully uncomfortable.

  5. MommaTRex*

    My boss is awesome, so I think it would be nice for me to remind her that I think so on Boss’s Day. A card isn’t needed to do that. A special day isn’t even necessary to do that. But maybe I’ll go on a coffee run as my treat. That’s the max that a lower-level employee should do, and that’s only if they treat more often.

      1. Lou*

        Even then I’d draw the line. I’d be like ‘sorry boss, you may think less of me but I can only afford Americanos for everyone’.

          1. nep*

            But why anything at all?
            In the case of any great boss I’ve ever had, far better to acknowledge that greatness by a) doing my job well and efficiently without needing my hand held and 2) preventing any surprises for the boss.

            1. MommaTRex*

              Of course, I agree with your a) and 2). I was talking about maybe picking up a coffee when I go on a run myself, something I do a lot and often pick up something for others (they pay and sometimes my boss treats). Sheesh. A coffee. Maybe. But coffee around here is a commodity that is given and shared freely.

    1. MK*

      If you have a truly great boss, someone who goes above and beyond for you, you can get them a card (or a present, if you want and can afford it) for their birthday or Christmas/other holiday or, I don’t know, bring them something from your holiday, if appropriate.

      1. MommaTRex*

        I say holiday/birthday present flowing upward is a big NO. Besides, I think she would prefer the compliment.

        1. MK*

          I was speaking generally; as in, if one really wants to show appreciation to their boss, they can do it in a case by case basis without imposing the pressure of an allocated day to everyone else and to all situations.

          As for presents flowing upwards, I would agree as a general rule, but again it can depend on many factors. I have occasionally bought gifts for people above me in the ladder, but a) by the nature of my job, I don’t have a boss per se, it’s more a case of senior colleagues, b) it was always because I wanted to, never an obligation, and it was received as such and c) the pay disparity isn’t great.

  6. Lou*

    What is a Boss’s Day? It sounds stupid and a bit weird lol. Do you treat them like a dictator or like royalty?

  7. Kyrielle*

    I think we should keep Boss’s Day around, rename it to Boss Day, and let everyone take the day off to go raiding in MMORPGs….

    Well, it’d be better than the current version, at least.

    1. Creag an Tuire*

      I say we repurpose it to be Talk Like Andy Samberg Day.

      Brewing coffee! LIKE A BOSS
      Eating breakfast! LIKE A BOSS
      Check my GMail! LIKE A BOSS
      Deleting p*nis spam! LIKE A BOSS

      And so forth.

  8. UncoolCat (formerly Manda)*

    I just read the title and was like, “woah, I’m gonna bet she’s gonna say ‘nooooo…'” Sure enough.

  9. The OP*

    In previous positions I’ve had bosses that I did like and wanted to do something for, like coffee or bagels. It was never required.
    My thought wasn’t so much a “thanks for being a great boss” card, but more of a “I’m really excited to be coming on board” card. I’m leaving a very toxic environment for my dream job. I am sure my excitement scewed my thoughts.

  10. Karyn*

    Ugh. Boss’s Day. We do a potluck breakfast for them every year here. I love my boss and usually get him a card, but I kind of always have this feeling of, “Y’all make $250,000 a year. Buy your own party.” I know that’s a terrible thing to think, but given that I make in one year what my boss makes in six paychecks…

    1. bridget*

      UGH. I mentioned this last year, but my last job would have a big potluck lunch where all of the support staff each brought a homemade dish and kind of … watched us all eat it. Even worse, we weren’t their bosses – we were just the lawyers at the law firm they supported. There was an admin who supported me (along with several others), but I was in no way her “boss.” I just hope that the firm paid them for ingredients and such, because on Administrative Professionals Day, I’m pretty sure that the firm just brought in some generic catering for them to have for lunch; the lawyers didn’t personally pay for and lovingly prepare homemade food. One more reason it sucked – 99% of the support staff was women, and 80%+ of the lawyers were men. It made the distinction even worse.

      1. Lionness*

        Oh gawd. That is so weird. They had to just watch you eat it? Not even share alongside?


    2. Mallory Janis Ian*

      I looked at my boss’ pay stub once, and he makes my annual salary in two paychecks (we’re paid monthly). I can only imagine getting a paycheck for half a year’s salary, and next month the other half, and having ten more still to collect. Le sigh.

  11. Elizabeth*

    We just got a “brief reminder” email from HR reminding us about Boss’ Day.

    Yeah, no.

    1. MommaTRex*

      Get. Out. That is freaky weird. I can hardly believe it, and yet, can totally believe it. Sheesh.

  12. Ruffingit*

    Last year was my first year at SUCKSMYSOULJOB and someone got a card for my boss. Since we’re a department of four including boss, I signed it. This year, I’m skipping it. I hate the guy, he treats me like crap, I’m not going to wish him anything but a slow death.*

    *ignore my homicidal attitude. Long week.

    1. Lily in NYC*

      LOL. I am so sick of signing bday and goodbye cards – we are a big office and it’s just too much because the cards are given across departments to sign so everyone is getting “signing fatigue”. I wrote “get well soon” on the last bday card because I was feeling passive aggressive. Maybe they will skip me next time if I keep writing rude things on cards.

      1. Mallory Janis Ian*

        Lol. Maybe pick a poem and write a stanza of it on each card that comes around. It doesn’t have to make any sense, and it could make you look forward to the next upcoming card so you can finish your poem and move on to the next one. Maybe some ironic synchronicities will occur.

        1. Mallory Janis Ian*

          I mean, if someone wrote, “with up so floating many bells down” or some such in my birthday card, it would give me something to think about.

  13. BananaPants*

    My boss gets 5-figure bonuses every year thanks to the work of his team – he’s bonus-eligible, we are not. So if anything, HE should be thanking US for busting our tails while he sits in his office bird watching and playing on his phone call day. Anyone who ever suggested that I should contribute to a Boss’ Day or any other form of gift to a manager would get an earful in a hurry about how gifts should only flow down, not up.

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