should I tutor my boss’s son, avoiding insincerity in a resignation letter, and more

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

1. Should I tutor my boss’s son?

It’s become known at my full-time place of employment that I have a second part-time job helping high school students prepare for the ACT exams though a tutoring service company. Recently, my boss at my full-time job asked me if I’d be willing to independently tutor his 17-year-old son in a high school make-up class that the boy has already failed. He has stated that he is willing to pay for my services if I agree.

I’m concerned about this for a couple of reasons. First, I’m not sure what this would do to the working relationship with my boss and how this could shift the power dynamic. Secondly, students that apply themselves at all shouldn’t be failing at this level, even if they don’t have much as much talent as their peers, which makes me think it’s more of a motivational issue than one of ability. If his son fails again after working with him, I’m not sure what my boss will think.

If I say no, I’m also a bit concerned about how my boss will respond. He’s not the type to lash out over something like this, but I don’t want his opinion of me to be affected by a response either way. I’m willing to help, but I’m not sure what to do.

I wouldn’t do it. There’s too much potential for problems, like if you have to deliver bad news about his kid and he’s one of those parents who doesn’t take it well, or he’s dissatisfied with the results you get, or if you have a disagreement about your rates. Your boss is the person who controls your primary paycheck and your quality of life at work, and it just doesn’t make sense to risk messing with it. (To be clear, it’s not that this will be a disaster; it could work out beautifully, for all I know. But the risk doesn’t make sense to take, particularly when the son presumably has other options for help.)

I’d tell your boss that you’re full up on tutoring clients right now but that you’d be glad to refer him to another tutor.

2. How do I avoid saying something in my resignation letter that I don’t mean?

How do I say “I wish you continued success” in a resignation letter when I don’t feel right saying that? I asked if “I wish you the best in future endeavors” would work as well and was told no, on the grounds of “You don’t care about their future endeavors” I honestly don’t care about their continued success either.

My job turned out to be a nightmare, so I started looking and was offered a new position. I’m drafting my letter of resignation and was told to end it on the note “I wish you continued success.” The job was so bad that I can’t even bring myself to write those words. What’s another way to say this? I know this sounds petty; I didn’t enjoy this job but I don’t wanna burn bridges either.

Who is telling you that you need to say any of these things at all? You don’t. A resignation letter really doesn’t need to be this fraught. It would be perfectly fine to just say this: “This letter is to confirm that, as we discussed earlier today, I will be resigning my position and January 15 will be my last day. I look forward to using my remaining time to help make the transition as smooth as possible.”

It’s true that it’s normally gracious to also say something like “I wish the organization every success,” but it’s not a requirement. (That said, sincerity is not a requirement in these letters either, so really it would make sense to just put a nicety in there and be done with it. No one cares whether you really mean it or not.)

Read an update to this letter here.

3. My boss uses a word to mean the complete opposite of what it actually means

My boss keeps using a phrase in his emails (to clients and customers) which means the opposite of what he believes it means. Essentially he’s in a customer service role and is in charge of resolving lots of escalated complaints. However, he frequently uses the phrase “I have personally overlooked the [matter/refund/issue].” My guess is that he actually means “oversee,” but I feel I can’t bring this up without looking petty. On the other hand, our customers are the type to notice this (and possibly escalate further, because of it). As far as I’m aware, English is his mother tongue; it’s not something being lost in translation. Should I mention this to him, or just overlook it?

Ha, I once had a boss who used “broach” to mean “shut down a topic,” which made for some very confusing (and entertaining) conversations.

Anyway, yes, mention it! You could say it this way: “I’ve noticed that there’s a recurring typo or auto-correct in emails that you send customers who escalate complaints — the email ends up saying that you personally overlooked the matter, when I think you mean to write that you personally oversaw it. Overlooked, of course, would mean that you didn’t do anything about it.”

(Any chance that he really does mean “overlooked,” though? Like that he’s taking personal responsibility for the mistake, saying that it was his fault, and then saying that he’s corrected it?)

4. What to say to persistent vendors demanding payment

I deal with many sub-contractors and vendors (suppliers) seeking payment. I have no control over accounts payable, nor do I have access to financial reports, but they expect for me to give them an answer right away. My boss is usually out of the office at the job sites or dealing with the project architects or what not. How should I handle persistent people demanding payment when I do not know when the expected pay-out check will be ready for them?

If your office is routinely paying late, that is crappy of them and the people persistently demanding payment are in the right. So you want to be as helpful and responsive as possible. For example: “I’m so sorry, I’ll get you an answer as soon as I can” — and then follow up with whoever has that info and then go back to the vendor with that answer. Or, if appropriate in your office, connect them directly with the person who can help them.

Also, you should alert your boss that you are dealing with regular complaints about this and ask how she wants you to handle it.

5. Getting buy-in for an unpopular change

I am coming into a position that experienced a large amount of turnover. First, a long-time employee retired and they had several different managers who did not work out and then I was hired. The employees have told me that they feel overworked and under-appreciated, and I have heard the dreaded “I don’t get paid enough for this” more than once. My employees seem to like me, as I listen to their concerns, but my employer has told me that a change they have fought against in the past is coming whether they like it or not (the addition of a duty that they are afraid will take up a significant amount of their time) and I need to smooth that transition and ensure staff buy-in.

Do you have advice for dealing with unpopular workplace changes? Advice on change in general is welcome too, as I am sure I will face more in the future.

Well, you can’t necessarily ensure staff buy-in, but you can try for it. The keys are to let people know that their input was heard and appreciated but that ultimately the decision was X, to be transparent about why the decision was made, and to be open about how their concerns about X will be handled.

For example: “I know a lot of you felt strongly that taking on X would be too time-consuming. I made sure that Jane and Fergus understood those concerns, and in particular shared your points about Y and Z. While they understood those concerns, they ultimately concluded that we’re the only place X can land right now, since Marketing and Sales are both swamped with the spring launch. So we’re going to take on X and try to make it work. However, we’ll keep a close eye on how it goes, and if Y or Z do become a problem, come talk to me and we’ll figure out how to handle it.”

(Of course, then you really need to do that last part.)

{ 416 comments… read them below }

  1. Engineer Girl*

    #2 – When I’ve left dysfunctional organizations I used the phrase “May you have the success you deserve.”
    The people that were kind always thanked me. The people that were trying to sabotage my efforts were enraged but there was nothing they could do about it.
    But really, you don’t need to say anything at all.

    1. Princess Consuela Banana Hammock*

      If it makes you feel better, OP #2, when I resigned from my toxic job I wrote, “This letter confirms that I resign my position as [position title] as of [date].” I’m not exaggerating.

      To be fair, it was also my first time writing a resignation letter, and I probably should have Googled sample language. But I had already given verbal notice and the organization was insisting on an “official resignation letter” about 1 hour before the end of my last day, so that’s what they got.

      1. Ask a Manager* Post author

        Honestly, that is completely fine! The resignation letter is not supposed to explain your reasons or go into a bunch of niceties; it’s really just to document the resignation itself, which yours did!

        Somewhere along the lines people started really worrying about these letters, but a single sentence like yours is fine. (I also want to emphasize to people — since this is another misconception — that the letter is not how you should deliver the message; you deliver the message in person and then follow up with a written confirmation if your employer requests it.)

        1. Princess Consuela Banana Hammock*

          That was kind of how I felt, and hearing that it’s ok makes me feel so much better, even years later!

          Before drafting the letter, I had given notice in person, had a long in-person conversation with the Exec Director where we went over transition and wind up, and also did a thorough exit interview (again, in person). I thought those conversations were constructive, but I didn’t think it would really help the organization or my ongoing relationship with the folks there to put my unfiltered feelings into words. It felt too much like a kiss-off letter instead of something they could use to wrap up benefits, last paycheck, etc.

          1. eplawyer*

            That is what it is for — to wrap up benefits, last paycheck etc. It is not the airing of grievances. It is not a break up letter with your boy/girlfriend. It is a simple statement documenting when you are leaving the company.

            All the other things, why you are leaving, how to wrap up projects are in the conversations you have.

            1. TootsNYC*

              Yep, it’s simply to provide a piece of paper they can put in the file, or hand to someone who has to fill out a form and need to look at something to confirm the date before they click “submit.”

        2. Mookie*

          Precisely. My written notices — nominal, because I notified my managers in person once I’d made the decision — read exactly like this. “I’m resigning, effective [here].” No one is mortally wounded or taken aback by a simple formality, politely delivered. This isn’t about elaborating or hedging to avoid terseness, it’s about providing facts as soon as you can to mitigate as much inconvenience as possible and make preparations for a proper exit.

        3. Mike C.*

          Ha! The only reason I had I write such a letter is because the most senior person around refused to get of the phone.

        4. Gandalf the Nude*

          I think a lot of people have this false comparison of the resignation letter and the cover letter, like thy’re bookend correspondence with your employers that should mirror each other in structure. So they end up rightly thinking of the cover letter as, “This is my introduction to the company where I explain why I want to work with them,” and then wrongly thinking of the resignation letter as, “This is my valediction to the company where I explain why I don’t want to work with them.”

        5. NotAnotherManager!*

          This exactly. About 1/3 of my employees are part of a usually 2-year employment stint, so I end up coaching a lot of people through their first resignation. Come and see me, go talk to your work teams starting at the top, and then send me an email memorializing when your last day will be for HR. That’s all I need; anything else is gravy. Most people do include a line thanking us for the opportunity or praising their coworkers, but that’s not necessary and certainly doesn’t reflect poorly on those who stick to the facts.

          How not to resign? Send only a hard-copy letter through interoffice mail last thing on a Friday before a holiday weekend when you will be on vacation the three days following the holiday and only leave your supervisor with four days to deal with knowledge transfer. And this was someone who, up until that point, had been a really, really good employee!

        6. Greg*

          Yeah, I almost feel weird contributing more words to a topic that shouldn’t have spawned this much discussion to begin with.

          The only time you even need a resignation letter is if the company requests one. And if they do, it’s solely for record-keeping purposes. No one actually cares what you write. Pretty much anything short of “I’m Audi, BEE-YOTCHES!” is fine.

          More broadly, it’s not the worst policy in the world to treat all of your official interactions with HR like you’re a witness testifying in court: Say exactly what you need to say and not a word more. Except that it doesn’t even matter. You could say too much and it still wouldn’t mean anything.

        7. CoveredInBees*

          I feel like people are conflating resignation letters with breakup letters. Frankly, if people didn’t fill the latter with vague niceties they wouldn’t get drunken, weepy calls from their exes late night about how “we can work it out.”

          If niceties aren’t necessary in a breakup letter, they certainly aren’t necessary in a resignation letter.

          1. Bluebell*

            I once had an employee cite “irreconcilable differences” in her resignation letter. Both HR and I thought that was an interesting turn of phrase.

          2. Misreader*

            I misread that at first and thought it said that they wouldn’t get drunken, weepy calls from their execs late at night. That would be infinitely more amusing as an episode from The Office.

      2. Natalie*

        My former silly HR department required a written resignation letter to open the job rec. They wouldn’t accept my email (“this is formal notice that I am leaving [company]. My last day will be [date].”) So I printed out the email, signed it, and sent them a PDF. That was apparently fine.

        Resignation letters don’t need to be much more than that.

        1. Not the Droid You Are Looking For*

          Oh gosh! That’s ridiculous.

          Our HR prefers email resignation confirmations, as they are easier to save an upload into our system.

          1. NotAnotherManager!*

            Yes, when I have people who resign on paper, I have to scan it and email it to HR. They prefer not to receive paper copies.

            1. Jadelyn*

              +100. Just fricken email me, please. I can print the email on my end if I need a hard copy anyway.

        2. Princess Consuela Banana Hammock*

          My organization did this, too. For some reason, having a signature was important to them (but they wouldn’t accept an electronic signature), which I don’t understand at all. It was a small group—there is no way anyone hacked my account to “fake resign.” I think people sometimes don’t fully understand record-keeping when they come up with protocols like this.

      3. K.*

        I’m not sure I’ve ever said more than that. I think when I left a role to go back to school, I mentioned that, but otherwise, it’s been basically “Effective [date], I will be resigning from my role as [title].” I’ve always resigned in person first, and it’s my understanding that the letter is for HR purposes and they don’t need reams of information.

          1. KayTee*

            Came here to say that. Anyone who stresses over what to write in a resignation letter should take a step back and remember that Nixon’s resignation literally said, “I hereby resign the Office of President of the United States.” The end.

            1. eplawyer*

              The best resignation/retirement letter that is succient and too the point, but still is kind of fun was sent by Steve Smith, Sr. of the Baltimore Ravens. Alison might not entirely approve but I thought it was one of the best ones I’ve ever read. In full:

              “This is to notify you that as of today, I, Steve Smith Sr., will no longer be antagonizing defensive backs. I am retiring from the National Football League.”

        1. Marillenbaum*

          Precisely! I left my first post-college position in May, and it was a fairly simple process: I told my boss that my last day was going to need to be sooner than we anticipated (but he still had three weeks’ notice), and he said fine, just leave a signed hard copy of the resignation letter in my inbox so I can fax it to HR. I did some light Googling, changed bits to reflect the relevant dates and titles, and got it done. It took maybe ten minutes.

      4. Xay*

        I’ve always done the same. To me, the resignation letter is just a formal notice of upcoming separation – nothing more or less. I usually have separate conversations or correspondence with my supervisors and colleagues if I want to say anything else.

      5. MashaKasha*

        That’s what I’ve written in my every resignation letter since the beginning of time.

        My coworkers and I have sent warm and fuzzy farewell letters to the team on our last day, if we were so inclined. But for the resignation letter, I’ve been told to keep it short and sweet and copy the bare minimum of people (your supervisor and your HR rep).

      6. jaxon*

        This is exactly what I’ve said in every resignation letter I’ve written. I don’t worry myself with niceties or adjectives or anything. This letter, itself, is not a tool to advance my relationships. It’s just an official notice that on [date], I will no longer be [position title.] You generate good will by giving your boss the news in a helpful manner, and doing the last two weeks of work to the utmost of your abilities.

        I don’t understand why you would ever need to say more.

    2. MillersSpring*

      Agreed. All you need to say is that you’re resigning X position and state your expected last day. If you have any planned time off before the final day, you should mention that too. If any other points came up in your verbal resignation to your supervisor, add that info too. Any niceties are superfluous. No one will judge you negatively for simply stating/confirming the pertinent facts.

    3. Freya*

      Oh I love things like that, nice work! I did something very similar when I left my last (toxic) job.

    4. ExcitedAndTerrified*

      Ah, the sincere complinsult, as my friends and I like to call them. They ought to be studied as an art form, I tell you. The goal is to offer something that can be said by you, with total sincerity, and which appears sufficiently complimentary that the other party is, in polite society, obligated to thank you… while the real meaning is actually an insult. If you do it well enough, the other party might never realize they’ve been insulted, unless someone points it out.

      “May you have the success you deserve” is a good one. Personally, I’ve always been partial to “Know that the esteem in which I hold you and your work has not changed” and “I would like to thank you for all that you have taught me; I have no doubt the lessons I learnt will serve me well.”

      Another good one is “I have never worked at a place that was so memorable before.”

        1. Venus Supreme*

          Although my resignation letter at ToxicJob was one sentence (my final day working here will be X), I did say in person, “I’ve learned a ton at this place and I will carry them with me at NextJob.” AKA, I learned how NOT to create a hell hole…

        1. Important Moi*

          I would be leery of this one because I looked it up. (I didn’t what it meant.) The definition made it clear this is an insult. Anyone who would make the effort to look it up would know. But as the letter writer, you may not care at this point! :)

      1. justsomeone*

        Ha, this is like my favorite birthday card line “I hope your day is as awesome as you are!”

      2. Greg*

        I never heard of “complinsult”, but it’s brilliant. Much better than a mere backhanded compliment (“That outfit you’re wearing is a huge improvement!”) I love how it uses a lot of big words to throw up a smokescreen around the insult.

        It also reminds me of how my friend used to use the term “unvitation”, usually in reference to casual dating situations: “I’m meeting up with my friends at the bar later tonight. You can come … if you’d like.”

      3. Princess Consuela Banana Hammock*

        I feel like this kind of shade is truly an art form (Engineer Girl’s version is soooo good). Isn’t this one of those conversational tactics in which Southerners excel?

        1. Marillenbaum*

          It really is, and there’s no shade quite like grandma shade. Once, I was in bed at noon when my nana called, and I mentioned that I just got up. She said “I’m so sorry, I didn’t realize I’d woken you up,” which is a reasonable thing to say, but delivered in her particular tone, was also a subtle condemnation that rang in my head for the rest of the day.

        1. Greg*

          “Jane Smith worked for the Chocolate Teapot company for three years, and when she left we were very satisfied.”

    5. always in email jail*

      BAHAHA I like that, I’m afraid people would immediately know I was being a bit passive-aggressive, though.

      My last resignation letter didn’t wish them luck in anything, but I did say something about being thankful for the experience and opportunity blah blah blah. What I meant was thankful for the opportunity because working there got me the job that got me OUT of there, but they don’t need to know that. The “experience” I was thankful for was the experience of navigating a toxic work environment, learning how to have difficult conversations at work, and getting a VERY good feel for the boundaries I intend to set at all future jobs.

    6. J. F.*

      I agree entirely with all the advice, but also, TRUE STORY:

      I work for a state college. When my boss resigned, first Head Honcho’s office and then HR sent my boss’s resignation letter back a total of THREE times and caused all manner of woe. This included a full month when Old Boss was in another state and yet still the boss, and Next Boss was running things but unable to make decisions, including on hiring a replacement for Old Boss or scheduling people for the next semester. I am still unclear on why it needed to say *anything* other than “Please be informed that I am resigning effective Date Here. Sincerely, Old Boss.”

      1. Candi*

        Oh for ever-lovin’ pete’s sake.

        Alison’s had a couple letters on ‘company won’t accept my rejection letter’. She’s made it very darn clear that it’s not up to them to decide whether your employment’s over in that scenario -that it’s the employee’s decision. HH and HR were just being total (insert language).

  2. Kat A.*

    #1: The tutoring company you work for might not allow you to tutor independently while you work for them because that would be like squirreling clients away from them. (You don’t want to risk damaging the relationship with both your employers.) Even if this is not the case, you could tell your boss that your agreement with the tutoring company is to go through them and that he will have to go through the company. BUT… if he does, you could still be stuck with tutoring his son. So this suggestion of mine is just something to add to AAM’s script. It could be something additional to discourage him from trying to hire you.

    1. JuniorMinion*

      This. The company I tutored through in college had this rule. One potential additional thought – give your tutoring scheduler a heads up that you aren’t available to tutor boss’s son due to conflict of interest / inability to be impartial.

      1. Pineapple Incident*

        This is a good thing to point out- if the boss can’t get the OP independently, she might go through the company itself to have her employee tutor her son. Situation hits the fan and suddenly is rife with COI problems.

    2. Artemesia*

      In addition to the obvious, the kid who is apparently a slacker (not necessarily but that is the best guess here) is going to resent Daddy’s employee tutoring him. He is already letting Daddy know what he thinks of him through his behavior (again not necessarily but father/son friction is very common in this scenario) This resentment will make the OP a poor tutor for this kid even if it were not inappropriate and dangerous to the job.

      1. Mookie*

        In addition to the obvious, the kid who is apparently a slacker (not necessarily but that is the best guess here)

        Dear lard, no. Despite what both you and the OP say, failing courses is not always down to willful laziness.

        He is already letting Daddy know what he thinks of him through his behavior (again not necessarily but father/son friction is very common in this scenario)

        What? No.

        The OP shouldn’t agree to this “offer” — that the boss is “willing” to pay for such services, suggesting that he’d prefer it be a favor, would send me caterwauling into the nighttime sky — but these speculations are not helpful in any way.

        1. Bwmn*

          While I think for us readers to speculate on the reasons why the boss’s kid is failing is problematic – the OP may have information about the school/class that makes the wariness of the kid’s issues more valid.

          Where I went to high school, failing a class was really uncommon. Sure, lots of kids struggled in all sorts of classes – but it was also a school with a fairly high level of parental/teacher involvement. So when Jimmy or Suzy was in danger of getting a C – let alone failing, there was a lot of proactive outreach by teachers and often involvement with parents. So if I heard a kid had failed even the toughest AP class – my immediate assumption was that there were *problems*. Possibly diagnosed learning disabilities, big issues at home, big issues with peers, issues with substance abuse – something. And unless I knew for sure that the reason was something like a protracted illness that had resulted in significant absences, I would have a similar concern that I was walking into a minefield or two.

          1. Countess Boochie Flagrante*

            But that isn’t what the OP said; the OP was saying that it was a motivational issue, not that it was just some kind of problem. The things you’ve listed are not “motivational issues.”

          2. Observer*

            The OP doesn’t even consider these issues. The OP writes that “students that apply themselves shouldn’t fail” Full stop. Hence, according to the OP, the boy is not applying himself and it’s a “motivational issue.”

            I know that we normally give OPs the benefit of assuming they know their situation. But, this seems to be a case where that doesn’t apply. The OP is clearly talking about generalities that he hasn’t checked out, much less seen if it actually applies to his situation.

            1. JB (not in Houston)*

              Technically, she said that students that apply themselves “at all” shouldn’t be failing “_at this level_.” That’s splitting hairs, but it’s not the same as saying that students who applies themselves will never fail. I’m guessing from this wording that there are factors that led the OP to reach the conclusion she did that she chose to leave out of her question.

            2. sstabeler*

              In this case, I’m not entirely sure it matters. It sounds to me like the OP more-or-less doesn’t take failing students at the level in question. That’s fine- presumably, the OP tutors at a different level. Assuming the OP wasn’t rude enough to say outright “your id is merely lazy” then I’m not sure it matters.

            3. Candi*

              I’m wondering if the boss is asking his employee (work situation) to tutor his son in subjects he’s failing (home situation), if he might not have boundary bleeding elsewhere that means the LW has far more information then they presented here. Makes for an interesting hypothesis.

        2. Relly*

          As another part-time tutor, I can’t +111111111111111111 this hard enough. Most of my students want to pass. And some of the ones who don’t have carefully cultivated the impression that they don’t care — because a teenager would rather be “the bad kid” than “the stupid kid.” (When in reality they aren’t either — just someone who needs help.)

      2. Tequila Mockingbird*

        Whether or not the kid’s poor performance is due to “lack of motivation,” OP is going to get sucked into the family drama if she agrees to tutor him. She’ll wind up being more of a guidance counselor than an academic tutor. Bad idea all around.

    3. I Herd the Cats*

      This to the third. It sounds to me like Boss is trying to hire you independently? (I could be wrong.) Finesse the details, but tell him you checked with your company (or can’t work behind your company’s back) and they have a rule about employees taking clients related to their workplace but they’d be more than happy to find someone else for him. And be sure to tip off your company first. If this isn’t an actual rule, it should be!

      1. Venus Supreme*

        Yup, I worked at a kids’ birthday place while in college and my contract stated I couldn’t get babysitting gigs from the families I met there! I think this is a great excuse for OP to use.

    4. Mookie*

      It depends on what agreements the OP signed (although noncompetes are de facto if not de jure unenforceable in some places), but she’s being asked to tutor subject matter for a course, not in preparation for ACTs which is what she does for her second job.

      1. blackcat*

        A lot of tutoring companies have overly broad non-competes, even in places where it is illegal. They also often have arbitration clauses in contracts. So OP1 should look carefully at her contract/employment agreement.

        1. sstabeler*

          it’s not actually necessarily overly broad- they could point out that they might want to extend the range of tutoring they provide, which would bring them into conflict.

          that, and it doesn’t need to be a noncompete agreement- it could simply be a case of moonlighting being banned, and you would get fired.

          1. blackcat*

            At least one tutoring company’s non-compete that a friend showed me declared any academic advice or tutoring either for pay or pro-bono as banned during employment and for a year afterwards. There was a specific note that employees were not allowed to volunteer or accept employment with educational non-profits or schools during employment and for a year afterwards. So that’s a non-compete and moon-lighting that is WAY overly broad. It could cover a parent helping their own child with homework! I bet they never enforced it, but I wouldn’t want to risk it.

            My friend showed me this as “Whoa, this can’t be legal, right?” and I was all like “Probably not, but I still wouldn’t sign it, particularly not with that arbitration clause there…”

            Some of the tutoring companies out there are good and reasonable (and include things like no moonlighting clauses, which I do think are fine). Some are not. Like all businesses, I suppose.

            1. sstabeler*

              hence “not nessecarily”- I was saying a non-compete or no moonlighting policy is not inherently overbroad simply by also banning closely related employment. ( in other words, they’d rather you referred people to them- which isn’t unreasonable)

            2. Parenthetically*

              And for a YEAR afterwards?! For a tutoring company?! That’s a unique level of draconian.

              1. Candi*

                When noncompetes have been dragged into court, the decisions usually fall into ‘you can’t prevent someone from making a living’. Those are mostly tech roles, but I’d like to see a company say, “no, we won’t allow them to make a living in their field after they leave our company” to a judge.

      2. Observer*

        The thing is that it doesn’t really matter if a non-compete really legally forbids the OP from taking the job. It’s still a valid reason for not taking it. It’s essentially saying “I’d like to do you a favor, but I’m not up for a legal battle with these guys.” That’s something most bosses will understand with out taking offense. And that’s what the OP really cares about here.

    5. Barney Barnaby*

      The big test prep companies tend to not allow you to take on outside students, and they also tend to not have tutoring for academic subjects (because the curricula vary so widely among schools; it’s not like teaching the GMAT or anything).

      I like Allison’s script, but the thing to add to it is a layer of professional respect for the non-compete laid out by your test prep employer. You will not go awry to discuss that you want to respect both the letter and the spirit of the non-compete. It’s the same thing as telling a new employer that you want to give your old employer two weeks’ notice: by showing that you respect one employer, the other one thinks that you’ll also respect them.

  3. Is Genevieve pronounced Jen A Veev or Zsahn Vee Ayve*

    #3 – this is always funny to me. In informal acquaintances, like people on social media, I would be quick to question or correct their use of the language. Unfortunately I find it a bit more awkward to do in relationships with this power dynamic or even with some friends, because I don’t want to look like a know it all or that I am insulting their intelligence. But if you are careful to frame it like you don’t think they meant to do it, like Alison scripted the auto-correct nod, then it’s definitely easier. I hate that sometimes you have to use infant-gloves for situations like these, but people can get their feelings hurt. lol.

    1. MillersSpring*

      Because it’s going to customers, I think the OP needs to speak up.

      But I feel ya. I have coworkers who consistently use “insure” when they mean “ensure” in internal emails. I just don’t interact with them close enough to feel like I could correct them.

      1. CM*

        Insure isn’t necessarily wrong. It’s more common to use “ensure” and only use “insure” when talking about insurance policies, but it’s acceptable to use them interchangeably.

          1. Parenthetically*

            I used to be very hard-nosed about this until I started seeing “insure” popping up in various classic literature where I would naturally use “ensure.” For example: “Mr. Wickham is blessed with such happy manner as may insure his making friends; whether he may be equally capable of retaining them, is less certain.”

          2. MillersSpring*

            Right. In today’s English, they are not interchangeable; only use “insure” if you’re literally talking about insurance.

            1. Natalie*

              Ages ago when I worked at Best Buy and had to sell those dumb extended warranties, my manager got on my case for using “ensure” correctly (that is, “make certain that”) while describing said product to a customer. There must have been some kind of corporate worry that people would think they were buying insurance rather than whatever the product legally qualified as, and for the life of me I could not get her to understand that those were two different words.

      2. Candi*

        Something I’ve done, if it is possible to do it naturally, is to use the correct word in context, or use the word correctly instead of how they are using it. Effect/affect tends to be easiest to do that with. If they don’t pick up on it, it’s okay, if they do, they have to quibble over something that is totally not a correction in context. Really. It’s not. (innocent look)

    2. Zip Silver*

      Easy mistake to make, he likely means looked over, and turned that into overlooked.

      What drives me nuts is a part/apart mistakes.

      1. Is Genevieve pronounced Jen A Veev or Zsahn Vee Ayve*

        “a part” vs “apart” drives me batty!! If someone asks me to “be apart” of [from lol] something they’re doing, I’ll gladly accept. Because between my social anxiety and my introversion, I’m sure I probably didn’t want to be a part of it! lol

      2. Emi.*

        What really gets me is over-correction type errors, like when people get bent out of shape that you responded to “Who’s hungry?” with “Me” instead of “I,” and then turn around and say “You were so kind to my husband and I.”

        1. Mononymous*

          Ugh, same.

          My other pet peeve: using “that” instead of “who” when referring to a person. Example: “Fergus is the one that usually handles the teapot order forms.” No, Fergus is a person, not an inanimate object! Please say, “Fergus is the one WHO usually handles the teapot order forms.” (Or cut out the extra words and leave it at: “Fergus usually handles the teapot order forms.”)

          1. Lissa*

            I did not learn the that/who rule until I was 30! I probably still sometimes mess it up out of habit, though.

          2. Princess Consuela Banana Hammock*

            That error, along with the “that” v. “which” error, are among the most common non-punctuation-related grammar edits I make.

            1. TootsNYC*

              There are pretty cogent arguments against the that/which distinction.

              I do find it useful, but I won’t get on board with saying that using it otherwise is wrong.

        2. Greg*

          Yeah, the point of language is to be understood. The laws of grammar have their place in formal communications, but in everyday conversation, there’s no reason to nitpick when the meaning is clear. That goes for subject/object mistakes, ending sentences with prepositions, “disinterested” (technically means unbiased, but if someone uses it to mean uninterested, you know what they’re talking about) and, my biggest pet peeve of all, “could care less”. Yes, I know you want to show me how smart you are by lecturing on how it means that there’s something you could care less about. Congrats, here’s a cookie. Now go look up the word “irony”. And then explain to me why people get so bent out of shape about “could care less”, but are fully able to appreciate similarly ironic constructions like “fat chance”.


          P.S. In the OP’s case, I agree she should speak up since the boss is actually using it in a way that could confuse customers, while also making the company look bad.

        3. Parenthetically*

          The thing that burns my biscuits is that it’s just not that difficult a rule! No one would say, “You were so kind to I” (except perhaps Lorelei Lee from Gentlemen Prefer Blondes), so why would it suddenly become correct with “my husband and” stuck in there?

          1. Princess Consuela Banana Hammock*

            I think it’s because (a) we’re bad at teaching grammar in K-12 public schools; and (b) we’re native speakers, and often spoken English doesn’t require the same fidelity to grammar rules as written English. Ninety percent of what I’ve learned about English grammar is the product of learning foreign languages (e.g., Spanish for noun objects and verb tenses; German and Swahili for noun cases).

            But it’s also hard to course correct when you’ve had grammar rules poorly explained to you and then beaten into your head. Even today, I have loads of (college+ educated) friends who haven’t figured out that the I/me distinction is determined by whether you’re the subject or object.

            1. Parenthetically*

              Oh, I totally agree with all of this. I’ve taught Latin and Greek and it’s amazing how foreign language grammar and English grammar are sort of mutually supportive. I find it really easy to teach English grammar, but the way it’s done in schools is so often just… baffling. Like an amalgamation of the worst theories and practices and timings.

            2. Hillary*

              This. I didn’t really learn English grammar until I was taking advanced French grammar in college. It came up so often that the school bookstore stocked the professor’s recommended English Grammar for Students of French even though it wasn’t on any syllabus.

              1. Cath in Canada*

                I think this is pretty common. My parents are both retired French teachers, and my Dad had more than one student complain that it was unreasonably difficult to learn French grammar “because we don’t have grammar in English”

              2. teclatwig*

                Totally. I was a major grammar geek (7th grade was diagramming sentences, totally the best!!), but I only gained a soul-deep understanding of grammar through Spanish classes.

        4. blackdog*

          And lately I’m seeing a lot of instances where people don’t even bother trying to figure out I/me and just use “myself” instead. “Please notify myself and Jane when the report is finished.” GRRRR!

      3. Jadelyn*

        The one that drives me nuts is discrete/discreet. “Please be discrete” well…I’m not sure how I’m supposed to be noncontiguous with your request, but I can try I guess.

        It’s really nails-on-a-chalkboard for me.

        1. bkanon*

          I wrote to a publisher to complain about this very mistake. They claimed they would fix it in the next edition, then attempted to say it was a US/UK English issue. Um, no. That’s torch versus flashlight, not discrete versus discreet.

      4. Emi.*

        My old youth group leader said “juxtapose” instead of “just suppose.” We corrected her (snotty teenagers, assemble!) but she kept doing it because she thought it was funny.

    3. Wakeen Teapots, Ltd.*

      I freaking love this one. It’s been too long since it has come up.

      I love it when someone sends a company email:

      “Fergus is out this week. I’ll be overlooking his work.”


      1. Mookie*

        “Fergus is out this week. I’ll be overlooking his work.”

        “No need to thank me. No, really, no need.”

    4. Sparky*

      I worked at a place that repeatedly used “verbiage” to mean carefully chosen words.
      “ver·bi·ageˈvərbēij noun speech or writing that uses too many words or excessively technical expressions.
      synonyms: verbosity, wordiness, prolixity, long-windedness, loquacity, rigmarole, circumlocution, superfluity, periphrasis”

      1. CM*

        But also:
        the way in which something is expressed; wording or diction.
        “we need to look at how the rule should be applied, based on the verbiage”

        1. fposte*

          Yup. That use is much more common in the U.S., and it’s about as old as the other (OED gives an example from the Duke of Wellington).

          1. Princess Consuela Banana Hammock*

            Yes, agreed. I’ve only heard verbiage used to refer to diction/word choice, not verbosity. I wonder if this is an industry-specific thing, though?

        1. Meghan*

          I also work for a non-native speaker and recently had to explain that “pervades” has a negative connotation, and you don’t want to use it when you’re saying something good is common in our industry. The sentence was something like “This [valuable and good trait] that pervades our industry.” NOPE

          1. Cath in Canada*

            I had a similar situation recently with a student who used “doubt” instead of “question”, as in “I had some doubts about your presentation yesterday”. I hope I did an adequate job at explaining the different connotations, because that’s the kind of thing that could get you in big trouble if you use it with the wrong person!

            1. Glenn*

              As a TA, I found that this is very common among Indian students who have come to the US relatively recently — my understanding is that, in Indian English, ‘doubt’ for ‘question’ is the common usage.

    5. Thornus67*

      I have a boss who misuses “ironic” and says “irregardless” at least once a day, each. She also “corrects” everyone to take out commas before “and” (because she doesn’t like the Oxford comma) even in situations where the “, and” is connecting two independent clauses (a circumstance which 100% of all grammarians agree is correct).

      And she was an English major!

      Drives me crazy.

      1. Elemeno P.*

        My director uses “snarky” both in the proper sense and also to mean “shady.”

        Examples from the same day:
        “I wanted to say that, but I didn’t want to seem snarky.”
        “We want to make sure that we look out for snarky individuals.”

      2. NotAnotherManager!*

        That would drive me insane. I work in legal where they are fanatical about the Oxford comma for clarity, and not using a comma to separate the two clauses of a compound sentence would make me crazy.

        But “irregardless” is like nails on a chalkboard to me, and I also had strong homicidal urges related to a former coworker’s repeated use of the “word” “fustrated”. My husband STILL teases me about this sometimes, and it’s been 10+ years.

        1. Catlady*

          Old boss at former dysfunctional company used “flustrated” and “indemlify” ALL THE TIME! The man had a college degree for hells sakes. Really nice guy, but geez.

    6. TheBeetsMotel*

      I had a boss once who would use quotation marks as a means of emphasis, where something should really have been underlined. Things like:

      Make sure this area is kept “clean”!

      (oh, I sure will! Lol)

      1. Brogrammer*

        I love seeing that on signs.

        Employees must “wash hands” before returning to work. Um… maybe I’ll eat somewhere else.

      2. Emi.*

        My greatest shame is that as a sophomore, I had a crush on a boy who later publicly defended this usage.

    7. Existentialcrises*

      A former boss used to mean “sorry for the inconvenience” but write “sorry for the incontinence.”

    8. LizB*

      I had a boss who would use the word “redact” instead of “revise” — e.g. “We’re waiting for the marketing department to redact that flyer before we send it out.” I felt too awkward to correct him, especially because occasionally “redact” actually was the correct word to use (we sometimes worked with confidential court documents), but I was never sure whether he really meant redact or revise until after I saw the finished product, when the whole point was moot.

      1. Anon 12*

        I had a boss who would become extremely flustrated. And since there were many flustrating things about that business, the word was in play a lot. I used to wonder if he really didn’t know that the word was frustrated or it was just some regional quirk he picked up somewhere.

    9. Turtle Candle*

      Many years ago, I agreed to read and provide feedback on a book written by a dear friend. (I no longer do this. I cheerlead my good friends, and provide feedback for people I know poorly or not at all, but I do not cross the streams anymore.) It was a very sweet historical romance, in which the heroine had a sister with whom she was very close (think Little Women-ish, but more of a straightforward romance), and they spent a lot of time talking about their beaus while braiding each other’s hair in the evening or whatever.

      Only she kept writing it as “Jane upbraided Cecily’s hair” or whatever, having apparently gotten into her head that “upbraid” was a fancier way of saying “braided” or “braided up.”

      So I kept getting these mental images of these sweet young women in their flannel nightgowns in their attic room, saying things like, “Oh dear sister, I am sure that you are being too modest! Master Rutherford has paid you such touching attention these past few days!” …and then pausing to shout scolding criticisms and at each others’ hair.

      (I did tell her that that was not what ‘upbraid’ meant.)

  4. Streets Ahead*

    #1 — Re: “…students that apply themselves at all shouldn’t be failing at this level, even if they don’t have much as much talent as their peers, which makes me think it’s more of a motivational issue than one of ability.”

    This doesn’t affect your question one way or the other, but in general, please don’t assume repeated academic failures at age-appropriate levels must always be a motivational issue. Learning disabilities and physiological issues that can affect learning outcomes (hearing and vision issues) can be easily overlooked by parents and teachers and go undiagnosed for years (if not forever). Either way, whatever’s going on with this kid, you shouldn’t tutor him because of the power dynamic with your boss, but as a tutor, I hope you would keep this in mind for future clients. Not that you’re in a position to diagnose or screen them, but perhaps it could be a reminder to suspend judgment, keeping in mind that there are often many factors behind academic failure that even qualified, trained observers are not always able to easily discern.

    1. Is Genevieve pronounced Jen A Veev or Zsahn Vee Ayve*

      I agree. That portion of the letter came across oddly to me. There were things that happened to me in high school, very traumatic things, that no adults in my life were aware of at the time, and it greatly affected me. I was also seen as “not motivated” when really I was dealing with a secret trauma of which I needed support and help, but was afraid to ask for / didn’t know how to ask for / didn’t exactly know what to ask for at the time. You never truly know what the causes for something is, and judging it based on your preconceived standards is harmful. You’re dealing with people, not well-oiled little robots. I was a master test taker, so I got incredible scores on any standardized testing, but I was failing classes left and right because of what I was dealing with in the dark and not because I didn’t try to or didn’t want to apply myself, and not because I was lazy or unmotivated.

      1. Relly*

        I don’t know if this helps you feel better at all — and I hope this doesn’t violate Alison asking us to move on, as I’m not meaning to castigate the letter-writer — but at my tutoring location, we’re actually encouraged to build a rapport with the students, and help them work through any resistance they’re having. Sometimes it’s as simple as a student blurting out “I hate being here, I hate this class, all my parents do lately is yell at me” — there, you sympathize, and explain that as grumpy as Mom and Dad are being, they’re probably just worried. Once they see how hard you’re working here, they’ll calm down, honest. Sometimes being listened to is all they need.

        Other times you get students opening up trauma. I’m no therapist, but I am a good listener, and Pre-Calc can wait for ten minutes while we talk about how the student is feeling, the ways in which he or she is (or isn’t) coping, and what resources are available to him or her to be sought out. (And sometimes, when necessary, info on how to get help without going through Mom and Dad. Not all parents are necessarily allies.)

        1. TootsNYC*

          I’m wondering–are you also encouraged to raise issues on things like learning disabilities, emotional or mental difficulties, vision problems, etc.?

          Not to treat or diagnose, but to send up a flare on the things you notice?

          1. Relly*

            Absolutely. We’re not, like, trained in things like “if you spot X, that means Y,” but we write notes about how the kid is doing, any patterns we’re noticing, and pass those along. Sometimes it’s just “I’ve noticed such-and-such, I don’t know what it means, or if it means anything.” Sometimes it’s “has Name ever been tested for dyslexia? Just wondering, because he keeps flipping letters.”

            With those, you don’t mention it to the kid directly — you pass it to the higher ups, who decide how to approach the parents.

            Sometimes it’s not even anything Serious so much as, “Kid did great the first hour, then completely hit the wall.” If that happens every time, maybe Kid should be here for one hour twice a week instead of two hours once.

            Anything and everything helps us get a good clear picture on how and why the student is struggling, and ways we / parents / the school can help.

        2. Countess Boochie Flagrante*

          I needed this so badly when I was in school :( I’m so glad it’s something that you’re encouraged to do!

          1. Relly*

            I did, too. :( I had undiagnosed mental health issues for most of my childhood / teenage years. It’s part of why I’m so passionate about this, and so, so glad my location has the same philosophy. Hugs to your childhood self.

      1. Mookie*

        Whoops. I responded a few subthreads above to a similar comment, so: sorry about that! Will read entire thread before contributing next time.

  5. Thefuture*

    #4: see if you can learn more on this…

    This happened to me at my current company and has NEVER happened to me before after over 15 years of working.

    Finally came out that our company was filing for bankruptcy. So be ready. We were rescued temporarily as it was chap 11 but the layoffs keep coming and I’m sure I’m next.

    1. Artemesia*

      Oh absolutely. when you see your company failing to pay bills routinely, you need to be hustling like crazy for a new job. When the end comes, it comes quickly.

      1. Amber T*

        My first job out of college was back office work at a service company (that had lots of expensive trucks with lots of difficult components). My responsibilities included “accounts payable,” but that was really just scanning any bill that came in and sending it to our CFO in the corporate office (meaning, I had no access to the checkbook to pay these, not even quickbooks to show we received them). I swear I fielded 10 calls a week from vendors. We used at least 7 different truck repair places (on 4 or 5 trucks) and couldn’t pay any of them (the reason we had so many was because the last place wouldn’t service us until we paid the rather large bill, so we moved on to the next place). Our water delivery company cancelled our account because of overdue invoices (we tried to explain to corporate that it was a nice perk but we didn’t need it, to which their response was “No, no, you need it!” then rapidly “Why were you ordering water??”). One time our utilities turned off our internet and phones, and the CEO put everything on his personal credit card to get it back up (after complaining that the company wouldn’t just accept last month’s payment, only everything that was overdue). The CFO tried to pass the blame on me for a while (“You never emailed me that bill!” while cc-ing my district manager and the CEO, to which I would reply all with the original email attached. She stopped that after a few attempts.)

        Ironically, some of my responsibilities were accounts receivable and “collections” (it wasn’t officially collections because collections laws in my state are strict), and while I did a good job in reducing the AR overdue when I first started, the CFO made multiple remarks how frustrating it was that SOME PEOPLE can’t pay their bills! I think I commented back during my last month (I had given 4 weeks of notice).

        This was on top of a corporate office that thought rape jokes were funny, made us all attend a virtual meeting the day after Thanksgiving, and *laughed* when my coworker killed himself. After four years I’m shocked they’re still up and running.

        1. Collarbone High*

          My first office job was bookkeeping at a place that was such a dysfunctional mess, our electricity went out one day and I angrily called the utility company, saying “Why did you cut our power? You said we had until today to pay our overdue bills, and I took a cashier’s check to your office this morning.”

          Turns out, the outage was caused by a blown transformer. I realized I needed to find a new job, because you know things are dire when your company a) assumes an electrical outage is due to shutoff for nonpayment and not a far-more-common mechanical problem, because the shutoff is a reasonable explanation, and b) routinely has to hand-deliver cashier’s checks to prevent utility shutoffs.

    2. Is Genevieve pronounced Jen A Veev or Zsahn Vee Ayve*

      This was really my first thoughts. If LW is getting that many calls where it is a pattern, something is definitely up with the financials and I would be keeping an ear to the ground and polishing that resume, JUST IN CASE. It could be something as simple as the person in accounts payable is terrible at their job and has been hiding it well, but I wouldn’t be too comfortable. I would keep my radar up.

    3. Sled dog mama*

      It’s also possible, but not likely, that these vendors are just calling wanting to know when they will be paid even though they are being paid in a reasonable amount of time.

      1. Observer*

        That many that it’s a constant problem? Not likely AT ALL.

        Much more likely that the OP needs to start looking for a new job.

        1. Happy Lurker*

          We have many vendors who have sold their invoices. The factoring companies call every week for a payment update. I have converted some of them to email and they call less, but the ones that are outsourced to another country call every single week. It is the same answer every week…you will be paid at terms. The worst is the call quality. I really hate VOIP plus a loud call center background chatter. I find myself almost yelling and covering my opposite ear.

        2. myswtghst*

          I’m not saying it’s a bad idea for the OP to start looking, but when I was involved with vendors, the ones I worked with did not ever seem to read the terms, and were unaware they typically were net 90 days for our org. So it might be worth looking into what the standard payment terms are for the OP’s organization to at least have a boilerplate explanation handy.

    4. Lex*

      It sounds like the OP is in construction, and in that case the calls from unpaid vendors would be more common and not necessarily indicative of a serious financial issue. Many contractors operate on a pay when paid system so if the contractor isn’t getting paid by the client, her subcontractors aren’t getting paid.

      1. hbc*

        Yes, and some industries just…work late payments as part of the expected financials. Lots of places tell you something is due in 15 days and then don’t consider it late until 30 days, so if they operate on the same kind of assumption, they’ll wonder why the heck you’re bugging them on day 16.

        I’ve also had a few service providers who operate on really short terms and aren’t great on their end. If you want to be paid in ten days, you can’t drop the paper invoice in the mail on day eight and then start yelling on day 11.

        So it’s good to keep financial trouble in mind, but it’s not the only likely explanation.

        1. Liane*

          It may be a disconnect between the vendor’s terms and how Accounts Payable does things at OP’s company. My husband used to work for an electronics manufacturer with vendors that mostly had 30 or 45 day due dates–but company policy was to treat them as being due in 90 days. NOT a good way to keep up vendor relationships.

        2. Statler von Waldorf*

          The worst industry that I’ve seen for late payments are oilfield companies. Most of the major oil companies don’t consider an invoice late until after 90 days, and they won’t even talk to you if the invoice is less than 60 days old. There’s a whole industry of small companies that do nothing other than take a cut of oilfield workers pay in exchange for paying them in two weeks instead of three months.

        3. zora*

          “If you want to be paid in ten days, you can’t drop the paper invoice in the mail on day eight and then start yelling on day 11.”

          Blerg, I just had a hospital finance department do this to me… so fun….

      2. Mreasy*

        We have 30 day terms for payment, which is very standard and indicated up front, but we work with a lot of vendors who are not used to those terms (think independent music/film creators who are early in their careers), so we’ll often get a lot of (well-meaning albeit frustrated) payment queries when the funds don’t hit their account 7 days after they send their invoice.

        1. Natalie*

          I am professional enough to not let this show when I receive phone calls, but I LOATHE getting follow up calls before the invoice is actually due. If you wanted the money within 10 days you should have negotiated that up front. Stop wasting my time!

          1. Happy Lurker*

            +100 and please don’t think because you dated your invoice 1/1, but mailed it 1/30, that it makes it due the next day.

      3. Jessesgirl72*

        And it’s “pay upon completion” with room for disagreements about what “completion” means. ;)

      4. Business Cat*

        Absolutely this. I work for a land surveyor and we frequently subcontract for various companies. Our invoices state terms of “due on receipt of invoice” but due to the system you mentioned we are aware that it may take 60-90+ days to get paid by certain vendors or counties on large projects. However it is standard protocol for me, as the office manager, to check in with them once a month to ask about the status of the payment process.

      5. Not the Droid You Are Looking For*

        My first job out of college was working marketing at a construction firm. Because it was a three person company, I was the one who answered phones, etc.

        I would answer a lot of calls from subcontractors who had failed to submit invoices but were demanding to be paid. Or guys who were half-way done with the job and wanted to be paid. Finally, what helped was that my boss started letting me have read-only access to the accounting system so that I could say, “I’m sorry, it looks like we haven’t received your invoice,” or “it looks like that job is not scheduled to end for another week.”

        1. Natalie*

          This is a constant problem with construction. I worked in property management for years, so we were hiring the general contractors, and we follow AIA standards for payment terms and documentation and such. But often the GC expected to be paid before they paid their sub-contractors but also needed paperwork from said sub-contractors to get paid by us… it was a mess, frankly.

      6. anonderella*

        This is also what I came to say – I’m a receptionist at a national general contractor construction company, and I deal with these calls pretty much daily. We can’t pay until we’re paid, so it’s good to know how to deal with these calls. Most of the time, it’s not people meaning to be rude, but they need payment. I just try to keep in mind how they must be feeling, but also with a strong STRONG mental baseline of knowing my limits on that issue. If the person who handles payment is out that day, I have to let them know; if it’s an extreme emergency, I pass on to a boss above me, because it’s not my job to handle the issue but it is my job to forward to someone who can handle it.
        Point being, if the person I’m on the phone with decides they don’t want to work with us anymore because of payment issues, that’s not my problem. If I dealt with them in a polite manner, their grievance will not be with me, but with the person who wasn’t doing their job. And if the calls happen a lot, it’s only my job to point that out to the right person, not to actually do anything about it. It can be difficult to navigate everyone’s emotions and expectations, especially when you do have a rude person screaming at you, but if you do YOUR job, you don’t have to worry about that fallout.

    5. Orca*

      My company currently has had high turnover in our AP department so though we definitely have the money things are not flowing as smoothly as they should be! So that’s another possibility, I’m an admin not in AP but have been a liason to help get payments going through lately because yes, vendors will call the person who set up the service.

      1. Ama*

        Yeah, when I had a similar payment liaison type job in academia, I had to run interference with our vendors a lot because our AP department was a nightmare combination of 30 year old technology, red tape, and high turnover. We still had to file paper forms for everything, which had to be sent through campus mail, and at least half of the time when a payment didn’t come through in a timely manner it was because the form either was lost in the mailroom completely or the payment request got separated from the invoice and then was sent back for “lack of documentation.” It was never about the money at all, it was just about really poor systems.

        By the end of my time there I was allowed a certain degree of budget access (in that I could see what payments had actually been charged to our account) which at least made it possible to be more proactive in identifying payments that may have been lost. But until I got that access, I basically had no idea if a payment was missing until a vendor called, at which point all I could do was apologize and promise to call AP for a status update.

    6. Interviewer*

      I worked in accounting for property development for a couple of years, and construction is definitely a different animal. They all wanted cash to buy materials to do the work. Or they wanted cash to pay their teams each week. Meanwhile, we got only got draws on the construction loan from the bank after certifying the work had been done. No one ever wanted to front any money, so it was a never-ending carousel of calls and draws and checks and bills. I hated those calls so much! Looking back, I can see now that my boss worked with the ones who were scraping by, but he had zero sympathy for any of them, and like your boss, he was always out of the office (pre-cellphone days), so he didn’t have to take the calls.

      You can start with reporting. Do you have an invoice aging report you can create? Find out how much is really long overdue? Then make a list of the people who call frequently, and let your boss know what’s going on. Call him to discuss it, set up a meeting, whatever it takes, and propose a system to get every single category of invoices on a regular schedule, then follow it to a T. If the subs know when they can expect payment, and they can count on you to follow it, that helps so much.

      If the problem is that your company doesn’t have the money – well, that’s a red flag you should not ignore.

      Good luck.

    7. Dora M. Meza*

      Thanks…I have a gut feeling that might be the case. I do not play a part in any of the financial aspects of the organization but I have to give the vendors/subcontractors the run around because I don’t get a definite answer. I have been here two months only but have over 20 years of experience with budgeting and financial reports. I feel that my business ethics is being jeopardized.

    1. ESP*

      As in “reviewed”? That was my immediate assumption as well. However, since the OP thinks that he meant “oversaw”, I’m guessing that the boss was saying that he personally made sure that the issue was resolved.

  6. Hattie McDoogal*

    #1, do you know your boss’ son at all? I had a similar situation in an old job (though the son was a lot younger) and I did know the kid pretty well, so when my boss asked if I would tutor him I was able to say, “Thanks for thinking of me! Knowing Junior, though, I think he might benefit from someone a bit sterner than me. I can give you the name of my old tutoring agency if you like.”

    1. TL -*

      Yup! I’ve had tutoring jobs where I 1) read the material out loud pretty much exclusively 2) explained a few things but mostly gave them a structured space to do homework and 3) did extensive explanations of concepts and materials and worked through problems with students. All of those involved students who were good kids; they just had very varied needs.
      Tutoring can vary a lot and if you prefer working with a specific type of student (which ACT prep classes may draw), a student who is struggling with a class you find very basic is probably not a good match. Whatever his struggle is, it doesn’t sound like it will match up with your patience levels for the situation, and that’s not good.

  7. CJ*

    Re #3. So English, joyously larcenous and flexible language that it is? Has this concept called “contronyms” (or “autoantonyms”) where a word has two definitions that are in opposition. Not that other languages don’t have them, but English has a LOT of them. If you think this is me leading up to say that “overlook” is a contronym? Yep. Merriam-Webster ( has the conflict with definitions 1 and 4 on the side your boss is using, and 3a-c on your side. So your boss is wrong, but he’s also right. It might be worth pointing out to him that he’s not wrong per se, but that even the dictionary is confused.

    1. Is Genevieve pronounced Jen A Veev or Zsahn Vee Ayve*

      Yes.. and no.

      I think a.) in context, even when applying the other definition it’s wrong. Because you aren’t just looking over the matter or looking down upon the matter, you are looking INTO the matter as a process of resolution. So I personally don’t feel the other definition works well for this particular scenario, although I thought the same thing about the word when I read this letter, regarding the definition(s) of the word.

      2.) I also think with English (and likely any language, but English is the only one I speak well enough, lol) when most people use a word a certain way and it is understood a certain way by the majority, it is important to remember that in speaking and in writing, lest you be misunderstood. There are a lot of words that “aren’t word” that have become words because of general use by the majority and because they are understood by the majority to mean whatever they mean.

      1. fposte*

        I don’t think the question is so much what it’s important to do in our own writing, though, as whether it’s important enough to correct other people. In general, unsolicited corrections are inappropriate, so the presumption is against a correction. The question is whether the result in this situation is enough of a problem for the correction to be important–and whether making a suggestion will get the OP into the soup with her boss.

        I agree that given the situation that OP is describing and the fact that she’s not talking about something that personally bugs her it sounds like it’s worth mentioning. I’d leave the “of course” out though–I know it feels collegial to the speaker, but it can sound really snotty to the recipient.

    2. Fiona the Lurker*

      Just coming here to say this, only not so elegantly. The sense of the expression has changed subtly; what he means is he’s ‘looked over’ it. Surely it’s possible to suggest this as an alternative ‘just to avoid any confusion’?

      BTW if we’re getting into language peeves, I knew someone who repeatedly said she’d received ‘an honoraria’. I wanted to hit her over the head with a dictionary every time she opened her mouth on the subject. Ugh.

      1. Mookie*

        I know several Valid Victorians*, myself.

        *me, I’m an illegitimate Edwardian (don’t tell Mother), so what do I know?

      2. Artemesia*

        LOL. The one that constantly had this effect on me was ‘doctorial degree.’ Used a lot in the south where they also ‘administrate.’

        1. anonderella*

          Huh? Is administrate not a word? I’m from the south, and my dictionary just says Administrate means to administer.
          I’m not going to say administer, because, being from the south, it reminds me too much of the word minister, and makes the word administer feel clerical (as in clergy) to me.
          Maybe I missed your point, but it seems to me that either use is fine?

          1. anonderella*

            aha, looked at a different source – apparently my first source is the only one that thinks it’s a proper word, haha.
            I think it’s an incorrect form of the verb, that is becoming a ‘valid’ word through popularity. Thus, in my native population, it’s an acceptable word. But honestly, it would never occur to me that it isn’t a proper word upon hearing. If that’s the word we’re taught, that’s what we’re taught. It also makes more sense out loud; an admini*strat*or is someone who admini*strates*, not admini*sters* – again, my ears hear MINISTER over admin-anything.
            I *do* have to regularly remind my SO that it’s not *brang* (from to bring) or *boughten* (from to buy), and he’s from the midwest. Oy, the grammatical crosses we bear : )

            1. Princess Consuela Banana Hammock*

              I was going to say, isn’t administrate similar to “ineptness” or “literally”? I.e., ineptitude is the adjectival form of something inept, but ineptness has become a word through misuse. Or how “literally” is now defined to also mean “figuratively” because of its frequent misuse.

              Although, arguably, if a word has meaning and that meaning is understood by the listener/reader it becomes valid/grammatical. The dictionary just captures the shift.

          2. Elizabeth H.*

            The comments didn’t refresh for me for some reason so I didn’t see this before I posted but I now realize it’s the administer/administrate issue. I do identify as someone who likes being slightly more precise/traditional with language but I kind of feel like in standard English usage administer has become more frequently associated with administering something to someone (administered his placement exam, administered her oath of office, administered the ointment to her dog 2x/day, administered the recommended course of treatment blah blah blah). But “I administrate the travel grant program” strikes me as a little more immediately comprehensible than “I administer the travel grant program” for example.

        2. Elizabeth H.*

          How was administrate being used incorrectly? I would use it as a verb occasionally although it’s somewhat imprecise and a little office-speak-y, it still makes sense to me to use in some contexts.

      3. Emi.*

        Someone at my alma mater once referred to a female graduate as “an alumni.” Noooo. If you can’t keep track of Latin endings, just say “alum” and “alums.”

        1. Parenthetically*

          A local high school’s alumni bumper stickers ALL say “Proud Malaprop Alumni.” It soothes my crabbed, shriveled grammarian’s heart, however, that the large all-girls Catholic school bumper stickers say “Sacred Heart Alumna.”

          1. Marillenbaum*

            I assume they do this because it’s simpler than having stickers that say “alumnus” or “alumna”, but it is so annoying!

          2. Emi.*

            Oh, I would’ve assumed that was intended as a plural, like “Townville Raiders,” since you do use the “masculine” form for mixed-gender groups in Latin.

              1. Elizabeth H.*

                Right, but plenty of bumper stickers list groups, I suppose to signal the affiliation in general rather than having to say “I, an individual, am a member of the group.” Like your sticker would say “Northwestern Wildcats” not “Northwestern Wildcat.” I do see the point though.

          3. ancolie*

            I went to an all-girls Catholic high school and we are (individually) referred to as “alumna” and receive the “alumnae” newsletter.

        2. Princess Consuela Banana Hammock*

          Isn’t part of the problem that “alumnae,” when pronounced properly in Latin, is similar to the correct pronunciation of “alumni”? I don’t know b/c I don’t speak Latin, but I’ve had multiple people who took high school Latin say that the common American English pronunciations of those words do not match their actual Latin pronunciation.

          1. Elizabeth H.*

            Right, “alumnae” and “alumni” are pronounced the same in modern English usage (the final vowel sounds like “eye”) but in Latin, only “alumnae” is pronounced like that, “alumni” has its final syllable sound like “ee.”

      4. myswtghst*

        I think your first paragraph is dead on. It’s less about boss being wrong, and more about how some people might interpret the wording differently than boss intends.

    3. Talvi*

      I personally love the ones that are regional/dialectal. Like how “quite” in American/Canadian English means much the opposite of how it is used in British English (or so I have been told; I cannot personally verify the veracity of this claim).

      Another is the use of “table” (as in, to table a bill) in the US (where it means to suspend a bill) is precisely the opposite of how it is used in Canada (where it means to introduce a bill) – this little tidbit ended up in a footnote in my thesis to avoid potential misunderstandings (one member on my committee was American and there was some confusion before I realised this was the source)!

      1. Parenthetically*

        I (an American) was married to an Australian for many months before I realized that, to him, “quite” softens a word’s meaning. In America, “quite good” means “very good,” because “quite” is an intensifier. In Australia, it apparently means, “sort of good,” which BLEW MY MIND.

        1. paperfiend*

          OOOOOH. That explains why my high school English teacher (at an American school, but in Singapore) told me off for using the phrase “quite good” to describe something… I meant “very good” and she probably interpreted it as “not really good”. Now 20 years later, I wish I could go back and explain what I meant…

        2. Princess Consuela Banana Hammock*

          Yes! They way that it was explained to me was that “quite” means mediocre/average/sufficient-but-below-expectations, etc.

    4. bridget*

      Yeah, although I think the usage the boss employs is so uncommon as to render it at least functionally wrong, this tidbit might help him save face and help the OP present it in a less awkward manner. OP can present it as “maybe choose a different word just to avoid confusion, because our clients might not know which version you mean!” rather than having it sound like “how embarrassing you are SO WRONG.”

  8. Kathlynn*

    I’ve been there, where I think I’m using a word correctly, for it to turn out I had it completely wrong. Somehow I thought epitome meant ‘worst example of’ not “a perfect example of” a particular quality or type.
    I don’t know how, but this lasted until I was in my 20’s. I was using it wrong all through highschool.

    1. Marvel*

      Boy, I know exactly what you mean. For a looong time as a teenager I was convinced that “bane of my existence” meant “thing I love so much I couldn’t exist without it.” My friends were very confused when I went around telling everyone that chocolate was the bane of my existence.

    2. Doodle*

      It could be because “epitome” is often used in phrases with negative words? Epitome of evil, etc.

      This American Life re-ran their “Kid Logic” episode a couple of weeks ago — the last segment is about kid misunderstandings that mysteriously persist into adulthood. Two of the word usage ones that I loved were that “x-ings” (as in “Deer Xing,” “School Xing,” etc.) were pronounced “Zings” because you’re supposed to hurry across and that “misled” is pronounced “mizzled” and is the past tense of “misle,” meaning, of course, to mislead!

      I think we all have these — just a matter of when and how embarrassingly they get corrected!

      1. Marche*

        I’m finding this hilarious because I read that as “deer zing” and “school zing” and wondered why it was making no sense.

      2. NW Mossy*

        Mine was not realizing that etc. stood for et cetera, and once pronounced it “e-checked.” My teacher at the time was rolling with laughter after that one.

    3. Trout 'Waver*

      I grew up thinking the same. I avoid using ‘epitome’ still have a negative connotation to me, even though it shouldn’t. I also encountered the word much earlier in reading than I heard it spoken, so I still scan it as ‘ep-e-toam’ instead of the correct pronunciation. Molecular biology and the word ‘epitope’ haven’t helped that any, either.

      Your post reminded me of another misuse of a similar sounding word. I was at a religious service, and they had a children’s lesson. The youth minister asked the kids if any of them had ever hand an epiphany. One 7-year old kid volunteered, “We used to have an epiphany, but Mom made us get rid of her.”

      1. MsChanandlerBong*

        My pastor once said the disciples were “prostate with grief”.” Now, I KNOW he knows it’s “prostrate,” but it came out the wrong way, and I nearly bit off my own finger trying not to laugh out loud in church.

    4. Emily, admin extraordinaire*

      I thought “condone” meant “disapprove of” for the longest time– well into high school. No idea how I got the idea in the first place!

      1. Kathlynn*

        I really feels like it should be disprove of. Probably because of condemn, idk. I always have to remind myself that it means to approve of.
        It could also be because we often use it in a negative way, that implies “approving of something one shouldn’t”. Like condoning abuse/abusive behaviors.

    5. Jaguar*

      I keep using erstwhile when I should be using earnest. I’m at the point where I know it’s completely the wrong word, but I’m not going to be clear of it until I can convince myself of erstwhile’s actual meaning, and for whatever reason, what the word actually means always slips my mind. If I can’t remember what it means, it means anything I want it to mean, right?

  9. Marvel*

    #1 – Yeah, I wouldn’t tutor my boss’s kid–and I have a fantastic relationship with her and know her to be an uncommonly reasonable and fair person, so it’s got nothing to do with personality. It’s just too big of a conflict of interest, and people get weird when it comes to their kids.

  10. anoneem*

    My boss often uses the phrase “the cruxt of the matter”… confusing crux and crust? This is verbal though and I have no idea whether I should correct him or not.

    1. Al Lo*

      When I worked at Starbucks, all the to-do lists and labels by one specific person mentioned the “milk crafts”. Drove me nuts. I thought it was just a verbal thing, mispronouncing “carafe”, but apparently not.

      1. anoneem*

        That would hurt! If you hadn’t said carafe I never would have guessed what “craft” was supposed to be.

        1. Al Lo*

          So painful! As was my sister’s boss who “alphatized” things and my friend who got “fustrated”.

          1. Fraunch*

            I personally hate “flustrated”, though I know some online dictionaries think it’s a word. I know some people use it to me “Frustrated to the point of being flustered”, but most people who use it just don’t know they’re trying to say “frustrated”.

            1. Dust Bunny*

              Guesstimate. We have “guess” and “estimate”: We don’t even need “guesstimate”!

              1. LBK*

                I use “guesstimate” when I mean an estimate that’s based purely on gut feeling and not any kind of drawn conclusion based on available data – essentially to contrast with an educated guess. The doubling down on the uncertainty is meant to indicate the low level of confidence in whatever I’m providing.

                1. fposte*

                  Yeah, I think that anchors in the fact that “estimate” is actually a formal projection in a lot of fields, so it’s a way to preclude that kind of binding certainty.

                2. Princess Consuela Banana Hammock*

                  Same—I always thought that it was ok to use, along with flustrated, when used for these specific meanings.

              2. Lissa*

                A lot of these, too, are fine in casual language — I might say “flustrated” to my best friend, but not in a work email! Same with “guesstimate”.

          2. Parenthetically*

            An acquaintance of mine did not differentiate between “character” and “caricature,” nor between “idea” and “ideal.” They were absolutely the same words in her mind, to be used interchangeably.

      2. Is Genevieve pronounced Jen A Veev or Zsahn Vee Ayve*

        I have a friend who says that people “go limb” when she means “limp” and she even writes it. She has a few others as well that I can’t think of offhand. I try to use the correct spelling and/or pronunciation or WORD around her as much as possible but it doesn’t stick with her, lol!

    2. Nic*

      People who tell me “We need to conversate about that” rather than “have a conversation” drive me nuts. It’s becoming common use in some of the areas around me, and I cringe so hard.

      1. Princess Consuela Banana Hammock*

        Do you think it’s because of the rise of its use in pop songs?

        I have a friend who uses “conversate” as an obvious joke (kind of like joking that you’re not “overwhelmed” but just “whelmed”), but I think she’d be horrified if people were using it sincerely.

      2. Anon for this*

        How do you feel about the song “Luxury” by Jon Bellion?

        Do people think “converse” isn’t a word?

        1. Princess Consuela Banana Hammock*

          Maybe they think it’s a shoe? ;)

          (I think most people know/use “converse” as a noun, not a verb)

    3. ExcitedAndTerrified*

      Where it’s verbal, I’d be a bit leery of correcting him on it, at least on the definitions of the words. There’s the distinct possibility that he may never have learnt to sufficiently differentiate between the “x” and “st” sounds when speaking them aloud.

      1. Turtle Candle*

        Yep. One other place I see this is in the ‘axt’ for ‘asked’ and ‘expresso’ for ‘espresso’ pronunciations–to some degree that is frequently a function of accent rather than a mistake. (A number of accents in American English, and possibly other Englishes as well, frequently alter a sibilant fricative + a stop into a stop + sibilant fricative + stop–I’m pretty sure that’s a fairly common pronunciation drift in a lot of languages, actually.) I’d tread carefully around that kind of thing because critiquing someone’s accent gets rapidly into dodgy territory. Better to stick to things where it’s a misuse and it’s potentially misleading, as in the LW’s case.

      2. anoneem*

        That’s a fair point! I’ve known people who said “aks” instead of “ask” for example, and just couldn’t manage it any other way. I don’t think that’s him but I definitely would not wish to offend.

    4. PB*

      My last boss always told people to “keep tract” of things. As in, “The time system is down, so just keep tract of your hours.” I drove me nuts.

            1. AcademiaNut*

              Neither have I. But I have worked in places that used SQUIDs (superconducting quantum interference devices).

            1. SusanIvanova*

              They used to be used in mining and when firing cannons. Ever see Mythbusters when they’ve set an explosive and it hasn’t gone off, and now they’ve got to worry about it potentially going off later? A damp squib doesn’t go off when planned but may go off later.

          1. Rat in the Sugar*

            Is that used as a metaphor on y’all’s side of the pond or did you literally have wet fireworks in the office??

            1. Marzipan*

              It’s a metaphor for something underwhelming, e.g.: “That big announcement at today’s staff meeting turned out to be a bit of a damp squib.”

        1. NewHerePleaseBeNice*

          My office mate used to have a monthly task to print out and post cerstificates to all the people who’ve finished their courses that month. She then decided it was too boreding a task for her so she got the other secuterry to do it.


  11. Maxwell Edison*

    #3 – I think your boss is my spouse. I’ve never known anyone else who could mangle meanings like that.

      1. fposte*

        Aaaand I just learned that she isn’t right now. Not that it makes a ton of difference to the song, I suppose.

        1. Emi.*

          I always thought “metaphysical science” just meant let’s put in something that sounds super highbrow and intellectual.

      2. Maxwell Edison*

        I’m always inordinately happy when someone catches the reference. Abbey Road needs a re-listen soon; it’s a perfect album (if you leave off “Her Majesty”).

  12. Susan*

    #2 – I wouldn’t worry about being sincere in this context. Your manager is not going to read anything into it other than you trying to be polite. She’s not going to think, “Wow, I thought Jane hated it here, but based on this resignation letter saying that she wishes us continued success, I guess she actually loved it!” If you do choose to include some kind of pleasantry, don’t worry too much about the exact wording. I don’t see anything wrong with saying you wish them the best in future endeavors. Again, nobody’s going to look at that and say, “What a jerk! I can’t believe she said she wishes us the best in future endeavors instead of wishing for our continued success!”

    Even though this job was a nightmare, there is some value in taking the high road and being pleasant on your way out, because that is the last impression you will make at this company. You never know when your path will cross with these people in the future.

    1. AnonAnalyst*

      This. I have to wonder if the advice OP received was to avoid saying anything that was obviously insincere, rather than adding in some polite pleasantries. I wouldn’t include four effusive paragraphs on how much you loved working there and how distraught you are to leave; THAT would seem insincere. But adding in a sentence about appreciating the opportunity or wishing the organization continued success? Totally fine. Nobody is going to scrutinize it that closely or have ongoing discussions about whether or not you really meant it.

    2. LBK*

      Totally agreed – I think it’s understandable to feel like you can’t even bring yourself to say that when you don’t mean it, but I guarantee no one is going to read that much into it.

      1. AM*

        Hi, OP #2 here. Thank you so much for the advice, I really appreciate it. I guess my biggest concern in wishing continued success is with my boss. He is VERY literal and I was worried it would open up a discussion that I didn’t want to have. Something along the lines of “If you want us to succeed, why would you leave then?”. I know it sounds crazy but he’s the type to do that. I haven’t yet spoken to him, but did give verbal resignation to my supervisor (1 step below boss) and that went well. Didn’t even ask for a letter, but I have one now in case he may need it.

        1. LBK*

          Gotcha – if you do know that he’s the more literal type, then I can totally understand being cautious about your wording. In that case I agree with Alison’s approach to just keep it to the facts of the situation: you’re resigning, here’s when it’s effective. Think of it more like a form you’re filling out than a letter.

        2. Troutwaxer*

          I think what’s happening here is that people are confusing the “resignation letter” one sends which announces the date and details of the resignation with the “it was a pleasure to work with you” letter one might send on one’s last day in the office. One can certainly add a pleasantry, such as “I wish the company continued success” to a resignation letter, but it is not required.

  13. Chaordic One*

    #5 Ah, yes. Change management. This gives me flashbacks to my old job at Dysfunctional Teapots, Ltd. (I think I have PTSD or something.)

    The OP really seems to be caught in the middle between her employer and the people she supervises. No wonder there have been several different managers in the short time before she took the job. If her employees already feel overworked and under-appreciated, and if the additional duty does indeed take up a significant amount of their time (which it sounds like it will), it is certainly understandable that they are pushing back.

    The employer is not giving the OP, or the people she supervises, the support they should be getting to do their jobs. Back at Dysfunctional Teapots I never had the sense that my concerns were relayed through my supervisor to the higher ups who really made the decisions, so I hope the OP will make it clear to her employees that she has indeed communicated their concerns to the powers that be. (I think my supervisor was afraid that it would reflect badly on her, if she raised the concerns of the people who worked on the front lines, and so she kept quiet about them.)

    When X doesn’t work, and a few balls get dropped because the employees are already overworked, perhaps the OP will have the ammunition you need to convince her supervisors to hire a couple of more people. I also hope the OP won’t be too hard on her employees if and when that happens because it is almost inevitable.

    I hope that your employees will be able to find other jobs, before or instead of your employers throwing them under the bus. You might want to start looking for another gig yourself. I think the high turnover rate is an indication of bad management at the upper levels of the company.

    1. Ask a Manager* Post author

      Hmmm, that seems like a leap from what’s in the letter! It’s certainly possible, but nothing in the letter is conclusive about that kind of thing.

    2. MK*

      Or the director who retired was incompetent and the staff is underperforming and the reason there has been a lot of director turnover is that the OP’s predecessors didn’t manage to turn things around and quit in frustration.

      Reading the letter, I am confused about the OP’s stance in this. There is a lot about how the employees feel and that she listens to them and tries to smooth things over, but is she actually evaluating the complaints? Are these people in fact overworked and/or underpaid? Will the addition of X make their workload unmanageable or is it simply something they don’t want to do? Are they truly underappreciated or is there not much to appreciate in the first place?

      My point being, not only we don’t know what is going on, the OP doesn’t seem to have considered what is going on either, except trying to get the staff to like her.

      1. nofelix*

        “but is she actually evaluating the complaints? Are these people in fact overworked and/or underpaid?”

        Yeah this was my immediate thought. And are these changes happening industry-wide or just in this company?

        1. ch-ch-ch-ch-changes*

          Hi everyone! OP here.
          Chaordic One, I agree that some dropped balls will probably happen and will give me the ammo I need to hire more staff but the big issue is addressing this change as it is coming down from the board. However, I agree with the board that the change will make our users happier so I want to make it work.
          Right now, I am looking at the tasks employees are being asked to do and evaluating possible solutions to the issues they have raised. I have simplified and streamlined some processes and it sounds like a majority of concerns that I was made aware of when I started were because the previous manager lied and didn’t listen to employees (But that’s a whole other hornet’s nest). It sounds like my employees want to be recognized for the work they do (who doesn’t?) and are worried that this new step will take them away from the parts of their job they enjoy doing, which is understandable.
          As a nonprofit, my hands are tied as to how much money I am permitted to offer my employees. I advocate for them every chance I get because they are doing great work and give credit where credit is due but I’m new so I can’t rock the boat too much yet.
          Thanks so much for your advice. I’m working on alleviating their concerns by evaluating the problems they have and providing any solutions I can find.

      2. Artemesia*

        good point. I once consulted about a division that was viewed as very unproductive and it was unproductive. The workload had fallen over time but the habit of endless whining about how much work they had to do was ingrained. On top of that the different office functions were stressed at different times of the year so a sensible approach would be cross training so they could back each other up during rush times; they resisted that; too hard and they shouldn’t be expected to learn these complicated (not) things. All this was encouraged by an undermining employee who was resentful not to have been made director. The fact was, they were underemployed and once we removed the pot stirrer and provided sufficient support for cross training, things worked very smoothly. So maybe the OPs employees whine about being overburdened because they don’t work very hard and hope to keep it that way. I think we all know people with little to do who complain constantly about how overworked they are.

      3. Turtle Candle*

        Yes, to me the way this should be handled depends on whether the employees are genuinely already overworked with insufficient appreciation, or if they’re not working as effectively as they ought (whether because they’re mired in bad processes, or they lack resources necessary to work more efficiently, or they’re slacking–I don’t usually jump to ‘sounds like the employees are slacking’ but in the real world it does in fact happen).

        If it’s the latter case, attempting to improve the efficiently and productivity of the department makes sense, whether that’s improving processes or getting better resources (like improved software or etc.) or managing them better. But if it’s the former, if they really are already up to their eyeballs (and feeling underappreciated) and this is just one more thing to drop on the pile, it needs to be handled with more delicacy. That might be showing appreciation for them (ideally monetarily, but by giving them flexibility in other ways if that’s not possible–PTO, increased schedule flexibility, etc.–and by making it clear that their work is valued and that they aren’t just the extra workload dumping ground). It might be pushing to hire more people. It might just be being sympathetic.

        I’ve been in both positions. When I worked a tech support job, I was initially in a department that really could have done better (and, with better management, did–we weren’t slackers, but we had terrible processes, outdated software, and management that was so hands-off that we genuinely weren’t clear what our priorities and goals were supposed to be. A management change brought in someone who improved the processes, successfully lobbied to get us better remote desktop and virtual machine software that made our jobs sooooo much less frustrating… and made it clear that he expected us to step up, too. And we did. (And we got rewarded with bonuses for blowing our new, clear goals out of the water at the end of the year.) In that case, the problem wasn’t ‘we can’t handle the workload,’ but ‘we don’t actually have a clear idea HOW to work efficiently enough to handle the workload because we aren’t being well-managed.’

        But I’ve also worked in an understaffed department that was doing very, very well indeed, working at high efficiency and very effectively–we got praise for it, even–and then two people quit (for reasons unrelated to the quality of the department–one got a book deal and the other got a chance to do her dream job in aeronautics) and we were assigned two new, MASSIVE products. We went from ‘working hard, working smart, staying on top of things’ to ‘working hard, working smart, drowning.’ And for a while, there was no real support beyond ‘you can do it if you just try harder!’ and recrimination if something fell through the cracks, even though our workload had increased by 1/4 at the same time our staff had decreased by 1/6. The mood of the department tanked, and we went from being enthusiastic about new challenges to being, well, kind of disaffected. We started pushing back when even more new big projects were assigned (but no hiring was being done), and got the ‘don’t have a bad attitude’ talk. It did eventually get fixed (our manager finally got through to his bosses that we had to either have some projects taken away or hire new people, because even working a lot of overtime it was functionally impossible for us to keep taking on new projects without dropping any old projects or hiring indefinitely, and we hired more people, and we shed some projects), but I will admit, seeing more and more work get dropped on us with a “keep a positive attitude and just work harder!” thing when we already were working very, very hard and very smart and were still dropping balls because it was just too much… was devastating for morale. Had we even heard a “yeah, it sucks, and here’s what you can safely triage, and we’re trying to hire, hang in there, you’re doing great with the resources you have” would have made a huge difference. (Some extra vacation at the end of the horrific crunch would have, too, I’ll freely admit.)

        So yeah, I’ve seen both from the inside, so I know that sometimes it’s ‘this group isn’t working as well as they could’ (and honestly, even as the employee on one of those teams, I could see it once realistic goals and management had been set before me) and sometimes it’s ‘no really, they have as much work as they can handle or possibly more, if we’re going to drop more on them we have to either triage out some less-important projects or hire more people, or both, because their capacity for tasks is not infinite.’ I have no idea which position the LW is in, but I can say that it really does make a difference.

        (Side note: I assume that the LW’s employees are exempt, but hands-down the worst morale I’ve ever seen was on a team that kept having extra stuff assigned to them but who were forbidden on pain of firing to take overtime, because they were non-exempt and it would cost money. So when they genuinely had more work than they could do, they had really no good options. I know they felt very set-up-to-fail, and were intensely bitter about it. I doubt that’s the case here, but wanted to flag it in case these employees are non-exempt and prohibited from OT.)

  14. Grrr Argh!*

    I once worked with a client who would swear a lot, and then say “excuse the pun.”

    English was definitely not his first language.

    1. Grrr Argh!*

      And I just remembered this one: when he was new in the job he worked on a project where he encountered a very industry specific word. He assumed they spelled it wrong, so being the helpful guy that he is, he went through all the documentation and “fixed” the spelling. The next day out lical grammar nazi made him change everything back.

      Awesome guy. One of the best people I ever worked with.

      1. always in email jail*

        That happens to us too. We have to use the word “materiel” instead of “material” in some contexts, and EVERY.SINGLE.TIME. there’s a new hire or an intern they feel obligated to go through my powerpoints and change it

        1. fposte*

          See also: “ordnance” and “ordinance.” I’ve gone round with people on that one a few times.

          1. Princess Consuela Banana Hammock*

            YES. I have had to correct this one multiple times, to the point where I finally had to screen capture the definitions from 5 different dictionaries (the person was higher up and didn’t want to click the links I’d provided). People are ridiculous, sometimes, when they think they’re right.

    2. beetrootqueen*

      That was a joke from a TV show though. Can’t remember what it was but by the guys from little Britain after every sentence this guy said he’d say that. Are you sure it’s not from that

      1. Grrr Argh!*

        Weird coincidence.
        I can assure you it really happened. And this guy’s knowledge of English was very basic, so it’s highly unlikely that he wad imitating some Briish comedy show.

    3. Gabriela*

      I once had a boss who was not a native English speaker who, although he had excellent pronunciation would say things like, “you and I- we skin our cats differently” and “when the cat is away, the mice- they will have a party”

      1. the gold digger*

        My boss – non-native speaker, makes me laugh. He says “we are shooting ourselves in the head with that one!” and “Hey! I have been on the rodeo before!”

        He also asked me, when I said he was just like Lucy and the football, “Who’s Lucy?”

        He is super smart, very well educated, and has been here since he was 15, so sometimes, I think he is pulling my leg. But he is completely deadpan about it, so I never know.

        1. Chaordic One*

          We had former co-worker who would use the expression, “you’re pulling my hair,” instead of “you’re pulling my leg.”

      2. Emilia Bedelia*

        These are fabulous.

        I had an adviser once who would say “thinking loudly” instead of “thinking out loud”… it was a minor thing, but we loved his turn of phrase.

        1. Emi.*

          I was crushed when I discovered that the opposite of reading out loud, reading “inside-saying-ly,” was something that my siblings and I had made up.

      3. jb*

        I’m hearing those in Michel’s accent from Gilmore Girls.

        “You know what happens when you assume.”
        “Something about a donkey.”

      4. Elizabeth H.*

        I love these little expressions you pick up from non native speakers. Russians tend to say “For example” a lot as a sentence starter (I know it’s also a normal and possible sentence starter in English, but in Russian I mean it’s REALLY a lot, like just to introduce a thought that is not an example of anything) and I start doing it too after talking to someone.

        1. MashaKasha*

          My second year in America, I translated a Russian expression directly into English when talking to a coworker. He and I both had preschool-age sons, and he was complaining about how his son would never sit still, always want attention, wear them out and such. I said, “aw that’s got to be tough. Mine just sits there quietly and plays with himself”. I had no idea what I’d said. But the look on the coworker’s face kinda indicated to me that it may not had been what I meant.

          1. Cath in Canada*

            A former colleague from Sweden once spilled some moisturiser on her clothes, and shouted “oh no! I have creamed my jeans!” very loudly across the lab.

            The same person walked into a snowboard rental place in Whistler once and asked for a strap-on, instead of a strap-in.

            Both times, I was the person who had to explain why everyone was laughing…

        2. Kj*

          I have dwarf goats and one of my co-workers from another country calls them “elf goats.” It is adorable and I have sworn my next goat will be named Legolas.

      5. Turtle Candle*

        I had a boss who was talking about how we had to have ‘a come-to-Jesus meeting’ with some of our industry partners who weren’t holding up their end of the agreement… only she got the idiom slightly inside-out and said “Those vendors, we have to send them to Jesus.”

        Which I’m sure would have succeeded in scaring them straight! But we gently corrected her as to the use of the idiom.

    4. MashaKasha*

      I might start using this! “Why, you little #^&*ing %^&* of ^^^ness! Pardon the pun.”

      I might even throw in “pun intended” once in a while, to change things up.

  15. Accidental Analyst*

    #4 I’ve been in a similar position before. The complaints about late (we weren’t allowed to call it non) payment got worse. Measures were put in place to track what was actually being paid vs what we were being told was being paid. Vendors started getting abuse to staff. Staff started refusing to answer those calls. A very sweet person volunteered to be the liaison. And ultimately the company folded.

    So the most important thing you need to work out is, is this happening because the company is slack or because the company can’t meet its obligations. If it’s the former that’s not good but you might be able to work with your boss to improve processes and communication. If it’s the latter, ramp up your job search.

    What helped our very sweet person was the fact that the vendors knew she was genuinely trying to get them paid. If she couldn’t get a response from someone she let them know. If she couldn’t confirm a pay date, she’d let them know and keep them posted. Contrast this to the person who made promises they knew they couldn’t keep…

    Good luck getting through this. Be kind to yourself

  16. Myrin*

    The general situation in #1 can be done – my sister tutors her boss’s son and it’s went completely fine so far. But the two situations are probably too different in their details to be really comparable; the son is just not quite up to par/would like to be better, there is no real failing of any kind involved; my sister doesn’t work through an agency but independently; her boss is kind of a fan of hers and is unlikely to react negatively even if things aren’t going well; the tutoring is actually going well so there’s happy people all around; this is a supermarket setting so rules and expectations and relationships are different from a regular office anyway. So, yeah, it can be done successfully but the details of #1 have me leaning strongly towards No.

    1. TootsNYC*

      “the boss is kind of a fan of hers”

      Several times, Alison has fielded a question about hiring a subordinate or colleague outside the office, and she always advises against it. Sensibly.

      But there’s a part of me that can TOTALLY see why a boss might want to hire a trusted subordinate. You know their work, you know you can trust them, you’d like the chance to increase their earnings, etc.

      It’s just so tricky, though.

  17. Myrin*

    #3, I’m laughing because I’m ESL and the literal translation of “oversee” into my language is the word that means “overlook”. Very confusing and it took me an eternity to actually really internalise it. However, if, as you say, your boss is a native speaker, that’s obviously not an excuse for what’s happening here; not really helpful for your particular situation but I found it amusing that this is actually a “false friends” scenario with regards to other languages.

  18. Yami*

    For #3, it might help to point out that it’s a fairly common mistake. I’ve never gotten them confused, but I listen to grammar podcasts sometimes and apparently it’s common to get them backwards or mixed-up frequently, even among native speakers. I guess it’s because “look” and “see” are very similar words, if not quite synonyms, and if you learn the two phrases in short succession, you might struggle to remember which is which? Anyway, I usually find it goes easier to tell people they made a mistake if you can point to evidence that it’s really no big deal, lots of people do it.

      1. Princess Consuela Banana Hammock*

        I like Grammar Girl, Grammar Grater, A Way With Words, and 6 Minute Grammar.

  19. Catalyst*

    Re: #4
    I would not jump to the conclusion that your company is going bankrupt (I note this because there are a few comments above that make it sound that way), it may be a possibility, but not the first conclusion I would draw. I have worked for many companies who paid late on a regular basis for cash flow (read: not paying interest on a line of credit) reasons. It is literally their policy, and they are in good financial health, have been for decades actually.
    That being said, if you are not in the accounting department (AP specifically) you should route these calls to them, they are the only ones who can tell vendors when they will be paid. And as someone who worked in AP for many years, I always found it frustrating not speaking directly to the vendor about payment, it is just so much easier to speak to the person who you are paying and explain what is happening (I’m not saying you are doing anything wrong, just that I’m sure you hate being a go between as well). Now, if your vendors are saying AP is not calling them back/responding, definitely bring this to your boss so they can follow up with whoever is in charge of AP, because that would definitely be an issue.

    1. Natalie*

      Yes, this is what I came here to say. It sounds like the OP is just saying “you’ll get paid” to get these people off the phone. Unless you know (directly from your AP department) what the hold up is, that can cause more harm then good if there is a real issue that isn’t being resolved. I’ve done AP as part of my job for a long time, and there are plenty of things that will delay payment besides financial insolvency: aging (holding invoice until due date or longer), missing required paperwork from vendor, work is incomplete or unsatisfactory in some way, AP department never got the invoice, etc.

    2. Workfromhome*

      This is good advice for more than one reason. Yes AP is often the end source of the answer anyways . The OP probably needs to pass this on to AP to get the naswe anyways so why not cut out the middle man. But in the case that its not AP simply being slow or missing these payments and its someone else’s responsibility (sales promising something that isn’t true), someone not doing their job etc etc having complaints go direct gets more immediate results.

      I dealt with similar things in old dysfunctional job. I would often get customers call me because technical support told them their issue would be resolved and didn’t or said we’ll get back to you within x hours and didn’t. I had no direct access to any systems to tell them anything and even when I did the support reps were so poor at documenting the issues that I couldn’t tell the customer anything. As I wasted hours being the middle man with support often asking for me to get more information from the customer.

      After multiple failed attempts to get technical management to resolve this problem I simply started to give the customers the manager’s direct phone/email contacts. After all I was putting them in contact with the person who could address their issue without a middle man. There were some very unhappy mangers complaining that they shouldn’t have complaints come directly to them and that there was a complaint line etc.
      BUT I did not have to deal with the calls anymore. Once the manager had to actually deal with these customers he was forced to take action if he wanted the calls to him to stop.
      It may not sound like the best thing to do (and YMMV) but the best thing for the customer is to get their issue resolved and if having you involved does nothing but slow the process then the issue needs to be handled by someone who CAN solve the issue. I think its one of those instances where “its not my job or I have no ability to impact this” is appropriate as long as its followed by “Let me put you in direct contact with someone who can>

    3. AnonAnalyst*

      If the OP’s company has an Accounting department, then she should absolutely be fowarding these calls to them. But I got the sense that this might be a super small office and only OP and her boss work there. If Boss is the one responsible for handling payables, OP might still be caught in the middle since he’s frequently out of the office.

      1. LBK*

        Yeah, I couldn’t tell from the letter what the OP’s role is and how these calls are ending up coming to her in the first place if she’s not in a position to be answering questions about AP. I got the sense maybe she’s an admin for the accounting manager? In which case I think it would be reasonable for callers to expect that she’d have more info than it sounds like her manager is willing to share.

        I agree with Alison’s advice that the OP should go to her boss and ask what to do when these calls come in. Most likely the manager will say to just forward them to her VM, or maybe the OP will be able to get access to the AP records to be able to answer those questions (although I think that’s less desirable as it makes her more accountable for something she can’t actually control).

    4. Dora M. Meza*

      Your last sentence is exactly my scenario. Except my employer is the AP Dept. It is a small organization.

    5. Mona Lisa*

      I was going to say this as well. I had a vendor once who kept hounding me for payment even though I told her that the university’s AP paid checks on a bi-weekly basis so it would take two weeks plus whatever mailing time from her invoice submission. She wanted her money sooner because she was in the process of buying a house (?) and expected a few day turnaround for each invoice she sent me. I finally got a point person in AP to talk to her, and that person became the vendor’s go-to in the future.

  20. Jen*

    #1. If you’re hesitant for any reason, say you’re full but refer him to someone else good.

    I’d have done this for any of my bosses, but I’ve always had a very good working relationship.

    1. CM*

      I’m wondering why the advice is to say she is full, rather than to just say outright, “I’d prefer not to mix my tutoring clients with my work here, but I’d be happy to refer you to another tutor.” I feel like the “full” advice might make the boss think that tutoring his son isn’t a priority for her, but the real reason is pretty easy to understand.

      1. Emi.*

        Yeah, just be straightforward. This isn’t an offensive or irrational reason to turn down work.

      2. Paige Turner*

        Yeah, and if the boss happens to know/suspect that OP’s schedule isn’t full (OP mentioned wanting to add more clients, etc), this wouldn’t work. Also, boss might say something like, “Put me on your wait list for when a spot opens up in your schedule.” I agree that it would be best for OP to cite conflict of interest or similar as long as she feels like boss would handle that reasonably well.

      3. Muriel Heslop*

        I agree that being honest is best. I have friends and neighbors ask me to tutor and I always decline on the basis of preserving the relationship. Please do refer your boss to either your company or a person you know that you think would do a good job (if you know one.) I have a few colleagues that I consistently refer to for this and it works out well. If the student in question is known to be under-motivated or uncooperative, I refer them to a local tutoring business.

        Good luck!

      4. Princess Consuela Banana Hammock*

        Couldn’t you also just say that you’re not able to take on Boss’s son right now, but here are referrals?

  21. always in email jail*

    Is there a reason you didn’t recommend that LW #1 address the fact she’d be mixing her primary and secondary work life head on? I recall a letter where someone who did pet-sitting (maybe it was house sitting?) had their HR person solicit these services, and they were advised to answer something along the lines of “I have a personal policy about not mixing the two”. I’m just genuinely curious about the difference, is the power dynamic at play?

  22. animaniactoo*

    #1 – if you’re tutoring test prep, a good “out” is telling him that you are unlikely to be the *kind* of tutor his son needs to pass a class. Since there are, in fact, different skill sets involved in each kind of tutoring. Most people can do both, but many specialize and it’s fine to let him think that you’re one of them.

    1. Artemesia*

      The problem with reasons is that they invite push back and argument; having a policy about not mixing work lives is clear and doesn’t invite argument.

      1. animaniactoo*

        Having a policy about not mixing work lives is also a reason, it’s just a different reason and can invite just as much pushback (depending on the how reasonable the other person is). However, the basis that you’re not the right kind of tutor is giving them a reason to not want you to do it anymore if they are the kind of person to resist your “no”.

    2. Bananistan*

      Yeah, I was going to point this out. I had both kinds of tutoring in high school– SAT and normal class– and they were completely different. Hopefully OP can say, “I actually don’t tutor for classes, but here’s the business card of someone who does.”

  23. Sibley*

    #4 – I’m an auditor, and have be in the guts of many organizations processes and financials. There are 2 main reasons why vendor payments are consistently late:

    1. The AP function has big problems
    2. The organization has cash flow problems.

    If it’s #2, I’d start looking for a new job.

    1. Sibley*

      Edit – someone else posted about a company that had a policy of always paying late. That can happen (and I’ve seen it actually), but it isn’t good business practice because a) you don’t get any early payment discounts and b) you risk angering your vendors.

      1. (different) Rebecca*

        I worked for a company that was a distributor, and one of our ‘customers’ had a 6 month payment backlog on a stated net 45. I mentioned to my boss that we should refuse to deliver to them until they were current and he had the gall to say “They’re one of our biggest customers! We can’t do that!” To which I replied, they’re not a customer if they’re not paying us.

      2. Dora M. Meza*

        I have actually had many of the vendors state that word of mouth locally is that we don’t pay and that concerns me. I am taking Business Management courses and I know something is not right. I feel very uncomfortable having to come up with things to say as to why vendors have not been paid.

        1. Natalie*

          Oooooh, in that case I might start looking for a new position. That’s a big difference from being a consistently slow payer or being stringent about documentation requirements.

          For whatever it’s worth, I would stop trying to “come up with things to say”. Don’t editorialize, but don’t excuse either – I do AR as well and we can always smell BS, especially from someone with a bad reputation in the industry or a clear history in our system of late/nonpayment. Pick a neutral line that communicates a) you’re sorry, b) you’ve done what you personally said you would do (passed the message along, followed up with boss, whatever) and c) what you can do now is X.

          If people are complaining, stick with simple validating statements like “I understand.” Again, don’t make excuses, don’t make promises. And if people become abusive to you, you do not need to stay on the phone with them just because they have a real complaint. Politely but firmly and quickly end the conversation.

          1. Catalyst*

            I totally agree with the ‘not coming up with things to say” thing, when I worked for the company that we paid late as a policy, I was up front about it. We pay 30 days past due, we always have, please look at our history, it is out of my hands. It was surprisingly effective but I think it was because I was obviously not BSing. We did of course have certain vendors that were integral to our business that we paid on time.

        2. Statler von Waldorf*

          Yeah, you need to start job hunting. Natalie’s advice is spot-on. Don’t “come up” with things to say, just stick to the facts. In my experience, your professional reputation will take a hit working at a company that doesn’t pay it’s bills. There is also the joy of wondering if someday you will be the person who wants to get paid but isn’t. Between those two factors, I wouldn’t stay there for long.

  24. blackcat*

    #1, this language raised a flag for me “He has stated that he is willing to pay for my services if I agree.”

    If he put it that way, I’d be more concerned–because he’s viewing paying you as something he’d be “willing” to do and the task of tutoring as an extension of your regular job and/or a favor. If, instead he said “I’m happy to pay you your regular rate” then I’m less worried–that indicates he is thinking of you as a professional tutor, who gets paid a fixed rate. This could just be how you wrote it up (in which case, ignore this comment!) or it could be indicative of a bigger problem around boundaries.

    Even if the boss is being great about it, I agree on not tutoring the kid. You can refer your boss to other tutors (both companies and listing services like University Tutor), and lots of people above have good reasons to give the boss for why you won’t tutor the kid.

    I do tutor for friends and family, though very carefully. For friends, I sometimes offer a discounted rate or barter (I tutor the kid who shovels my driveway in the winter, we call it even. But I really like the kid and his family couldn’t afford my rates). I tutor for family very infrequently, and I refuse payment. My family, though, always offers to pay. This works because I trust and like my family–it is often not the best idea.

  25. shep*

    #1 – I tutored for several years through a franchise, also teaching SAT and ACT prep courses. Personally, I would have no qualms politely declining this request. Like you say, my fear would be that his grades would not improve after working with him, and it would affect my working relationship with my boss. Even if the effect were slight, I’m sure there’d be some element of change there, and I wouldn’t want that.

    I had excellent students who showed marked improvement, and I’ve had students who were clearly only there because their parents thought we could magically turn their disinterested C-average student into a top-percentile college admissions test scorer. In my experience, there’s really no way to tell what type he is until you work with him, and I wouldn’t want to risk that.

    As others have said, if you’re tutoring for a company, you may have a non-compete agreement in place with that company already that prevents you (conveniently) from taking on clients outside of the company. Or, as animaniactoo above has suggested, you might tell your boss that since your specialty is in test prep, you don’t feel equipped to help in this particular case.

  26. Rebecca of Sunnybrook Farms*

    If it makes you feel any better #3, my husband says “tangical” when he means tangential. Repeated correction has done no good. Also, for some reason pronounces assuage, “a-sausage”. But I think that’s more of a verbal thing :)

    1. Maxwell Edison*

      I have certain words that I pronounce incorrectly to help myself remember the spelling. For example, I pronounce HIPAA as “hip-AAAH” to help me remember that it’s two As and not two Ps. But I don’t do that in front of other people.

      1. Princess Consuela Banana Hammock*

        I have done this with too many words to count (it’s the mismatch between reading a word and hearing its pronunciation). I finally bought You’re Saying It Wrong, which has been so helpful.

      2. first comment it's a doozy*

        I always think “quin-oh-ah” when I type out quinoa. I know it’s “keen-wah” but that’s not going to translate into my hands when I’m writing it.

    2. Sibley*

      For a very long time, I could not say “specific”. The closest I could get was “pacific”, which is an ocean. Eventually, my tongue figured it out. I did have some speech therapy when I was young to help with some specific issues I was having. I assume “specific” fell into that category and wasn’t covered during the therapy.

    3. HannahS*

      I worked at a museum with a woman who would reply to interesting comments from visitors with, “Well, that’s a great little timbit.” Meaning tidbit, like a small piece (of information). I never corrected her because I thought it was so charmingly Canadian.

  27. Marcy Marketer*

    #1 I definitely wouldn’t tutor the child of a supervisor. I have worked with family members on their college essays, and I can tell you that working with their parents was the hardest part of the equation. They were always pushing me to basically write it for them, or “motivate” them to write more. Things were pretty tense for a while and it wouldn’t have been too comfortable to go to work every day with them. I had to give several reminders that the students’ work is a reflection of their abilities, and I needed all the work to truly be their own. Plus, and I forget how I worded it, but I basically said that if the student wasn’t motivated to write the essay, maybe he’d be a better fit at a less competitive school. I definitely said it more nicely than that but yeah. It was rough, and I wouldn’t want that awkwardness at work every day.

    If I were you, I’d apologize and say you have a policy about working with children of friends, family, and coworkers, but that you know some other great tutors you’d be happy them to.

  28. Meghan*

    #1 As someone who worked for a tutoring company teaching test prep for many years, I would be extremely surprised if you were allowed to take on independent clients. Most tutoring companies require you to take all clients through the organization and sign a non-compete. The competition between companies can be fierce and they are rarely OK with you using their curriculum outside of the organization. You should check your handbook on this because it could give you an easy out. Just refer your boss to the company you work for. But do not, under any circumstances take on this student. I’ve seen too many parents with unreasonable expectations blame tutors for their kid’s failure. Stay far, far, far away from this.

    1. shep*

      “I’ve seen too many parents with unreasonable expectations blame tutors for their kid’s failure. Stay far, far, far away from this.”

      Exactly this. Meghan hit the nail on the head with what I was trying to say above.

      1. sstabeler*

        one obvious caveat- it’s most accurately a mismatch between tutor and student, not being either entirely the tutor’s fault, or entirely the student’s fault. (what I mean by that is that there are some tutors that are good at handling recalcitrant students, and some that are better at handling students that simply need extra tuition, rather than being uninterested. A tutor that’s good at breaking things down to make them easier to understand is going to struggle with a student that just doesn’t care- conversely, a tutor that is good at getting a student actually interested in the subject would not nessecarily be able to help someone who can’t actually understand what they’re getting at. (and, of course, there ARE students who, through no fault of their own, just plain aren’t very good at a subject- for example, no matter what my parents tried, my handwriting is utterly illegible. I’m just plain crap at it.)

        having said that, it’s true enough that if a tutor doesn’t believe they can help a particular kid, they should stay well away. It’s just it’s not always fair to say the student is “at fault” in the sense of being lazy.

        1. shep*

          I agree with this theory; I mainly just meant that it’s a good policy not to tutor friends’ or coworkers’ children.

          (Also, in my experience, when I have a student in SAT/ACT test prep who is reading at a fifth grade level, I’m sorry, but I can’t magically fix your child’s SAT/ACT scores in eight weeks like you think I can. That’s more of the “unrealistic parent expectations” I’m thinking of, which was very and unnervingly common.)

          1. Kj*

            Yeah, I tutored for a while and I was always shocked at the parental expectations- they were not at all reasonable. Most of my students were not native english speakers, coming to the states at school-ages- the SAT is hard enough on native speakers, your non-native speaker is not going to get an 800 verbal except in very rare cases. I can try, but you’d be better off if your kid writes a great essay about his or her struggle to learn english for his or her college application.

            Also, parents, colleges KNOW when the essay wasn’t written by the student. And I am not going to write your kid’s essay for them. Nor am I going to “edit” it to the point where his or her voice is lost completely.

        2. anonderella*

          was this supposed to read “and some are better at handling students that simply need extra attention” instead of “extra tuition”? or extra “tutoring”, perhaps? Just trying to understand, sorry if I’m wrong about it being a mis-word!
          I was absolutely a recalcitrant student, btw; also in a school that valued discipline over education, so I feel like I am so much at a disadvantage than my peers from that time now, as I am very capable of handling conflict and arguing well, but I don’t have the grades to get on anybody’s radar job-wise.
          Ironically, the end of my school days seemed to put a stop to my recalcitrance; never since have I known so clearly who I was, or what I was against.

          1. sstabeler*

            bit of both, really- what it was meant was where the kid just plain needs help, rather than it being a case of the kid not bothering to do the work.

        3. Meghan*

          The biggest issue I came across as a tutor was kids who didn’t read outside school assignments (and even then, usually just Cliff Notes). I can’t teach a kid critical reading skills when they don’t read books. I can teach your kid algebra they don’t know, and I can probably get them better at grammar, but I can’t make a kid who hasn’t read a better reader. But also, there were times I was tutoring a kid who was scoring mid-500s across the board and the parents wanted them to get into a school that expected 700s across the board. No tutor was going to be able to make that happen.

          So yeah, what shep said.

        4. Observer*

          There are a LOT of different types of unrealistic expectations – mismatch between tutor and student, kid who doesn’t give a hoot, kid who CAN’T, kid with other issues that make all of this irrelevant. Regardless of which one it is, for the tutor who gets blamed, it’s just a mess.

          1. Troutwaxer*

            Maybe the appropriate thing is to tell your boss, “I have a non-compete, but I’ll happily talk to your kid and see what they need, then pass them on to the right colleague.” That way you can be seen as taking a little interest and giving an evaluation and you can head the kid in a good direction but you can’t fail at the task and you don’t have to discuss the kid’s faults with your boss.

  29. regina phalange*

    #1 – Not the same thing, but I used to babysit for my old boss because we used to live within walking distance of each other. Although I use the term babysit very loosely, as the deal was they would put the kids to bed before they left and I would be there in case the kids woke up and needed me for any reason. But in looking back, things could have gone haywire and then I would have wished I said no.

    1. Lissa*

      I read this as”I used to babysit my old boss” and was thinking of all the potential awkwardness that could come from that! It could be its own letter. “Help! The awful child I babysat as a teen is my boss now!

  30. The_artist_formerly_known_as_Anon-2*

    #2 – this can be tricky. I’ve had to make unfriendly resignations – stating the reasons (money, was disrespected in negotiations, unpaid expenses, etc.) – did so without thinking that it could affect a recommendation later on down the road.

    Another time I resigned – because it was apparent my department was going to be eliminated. When I gave my verbal notice, I was asked if I’d consider a counter-offer, I said, yes, if it’s tangible either in the present or immediate future – and the “counter offer” was, I was to be laid off in eight months, and if I agreed to stay on until I’m laid off, they’ll give me three weeks extra pay! Yeah, WOW! When I did submit my letter of resignation – it was “the uncertainties of the longevity of my current situation, which were verbally confirmed.”

    I had also been passed over for what would have been a more certain position three weeks before, which had convinced me to start looking — and no one, including my manager, was surprised at my departure.

    My last resignation (21 years ago) was a bit more touchy. I had been in a long, protracted period in which I should have been promoted to a higher grade but wasn’t. Then I resigned and the promotion was already prepared, the counter was already written up. I accepted the counter and stayed another six months. When I did leave, I asked my manager for guidance on the res letter – and agreed to say that a forthcoming office move was one reason, the other (accurate) was that I was going to be going into an IT specialty that I wanted to work in.

    I did, say, however, in the exit interview – that the “no promotion unless you put a gun to our heads” was a dumb policy – because you have lost a lot of good people through that, and I probably wouldn’t have listened to this other company had I not had to force the promotional issue.

    1. AM*

      Thanks for the advice, it is very helpful. This does bring me to another question though; how should I address the issues for why I’m leaving? I don’t want to insult anyone, leading to me not having a reference later on. I like your direct route. This is my first career job out of college so I’m not sure how to handle this situation.

      1. Observer*

        Don’t. If you have an exit interview, and can trust the people to be discreet, then you can tell them what was bothering you and what the issues are. Otherwise “new opportunities” is what you stick to.

      2. AnonAnalyst*

        You’re in the best position to judge whether giving that feedback to your employer will be well received. If you think your employer won’t be open to hearing anything negative, you can just keep your reasons vague and high level – like, “oh, this great opportunity just came up and I couldn’t refuse!” or “There wasn’t anything wrong with [Current Company], but this new opportunity is just a better fit for me all around and more in line with my long term goals.”

        Generally, I try to share the reasons (professionally!) I’m leaving a company because it gives the company some concrete issues to address to try to improve retention (if they can). I’ve been lucky that most of the companies I have worked for have genuinely wanted my honest feedback, so they were just happy I was willing to give it and didn’t hold anything I said against me. Having said that, I am getting ready to leave the company I work for now, and I may not share the real reasons I’m moving on with the company because I’m concerned that it will impact my reference from this company in the future (they take everything personally and have weird ideas about loyalty).

        1. Troutwaxer*

          Loyalty? First of all, that’s a two-way street, and second, there are 200 million jobs in America; you have not done anything special by employing me!

  31. Zhook*

    #3 my boss uses ‘fetish’ to mean ‘pet peeve’. Our workplace is such that we all chipped in to explain the difference, with examples.

  32. Statler von Waldorf*

    #4 – One of the worst jobs I had was working as a bookkeeper at a company that was circling the drain. The constant calls for payment was bad, what was worse was every two weeks I’d wonder if our paychecks would clear the bank. I was effectively hired to get blamed for the owner’s financial mismanagement. That job was so soul crushingly bad that I found getting committed to a mental health institution was a huge improvement.

    I’d talk to your manager, and see how your manager wants you to handle it. When you are having this conversation, pay close attention to the subtext. Is there a clear sense that there is not enough money to pay all the bills? Run for the hills. If the subtext is more disorganized than broke, that’s less of a red flag. It could also be an industry standard, which wouldn’t be a red flag at all. So I wouldn’t panic yet, but my eyes would be wide open.

    1. MsChanandlerBong*

      Sounds like my father-in-law’s company. His sister worked there for years, running the office, handling customers, doing the bookkeeping, etc. As the person doing the books, she knew very well that there wasn’t enough money to cash her checks when she got them, so she would hold on to them for weeks. At the time, she took care of her sick mother, so she didn’t have to worry as much about bills (she contributed to the household, but her mother paid some of the bills, so she didn’t have to pay them all on her salary). When her mother passed away, she could no longer afford to hold her checks. She quit and went to another company. Of course, the narrative is “Aunt Petunia really screwed us by quitting,” not “We couldn’t manage our money properly if you held a gun to our heads, and Aunt Petunia was never able to cash her checks on time.” The sad thing is, it IS a matter of mismanagement. They generate millions in revenue every year, but instead of taking a smaller salary when business is slow, my FIL takes a huge salary and all kinds of bonuses, and then there’s no money to pay decent wages or hire employees to handle surges in demand. I’ve helped out in the office a few times, and I’ve had to put off vendors looking for payment/utility companies wondering if they were going to get paid any time soon.

  33. KayTee*

    #4: I work as a contractor for a company that has many, many payment issues. All I can suggest is definitely don’t lie about it. When the payment issues are so persistent, it’s a fair assumption that everyone is aware of it, talking about it, and knows that any excuses are BS. (I’ve never worked at a place where people regularly discussed pay before, but this place has sometimes been so dysfunctional that we all started talking to figure out how many of us were getting a run-around.) So after a while it would be better to just say “Let me get back to you” “I don’t have an answer on that” or “Nobody’s given me an update on that” than to say things like “A check is in the mail” when you know it’s not. Repeatedly lying just makes you look disrespectful or condescending because we’re not stupid.

    On another note, if you’re fielding all these calls and have no ability to change it, you may want to reconsider where you work.

  34. Observer*

    One thing – no matter how your boss wants you to handle it, and no matter what he says, DO NOT LIE. If for no other reason than it’s going to come back to bite you, as others have mentioned. Polite, as helpful as you can be, whatever else your boss wants, but always as truthful as you can be and never something you know not to be true.

    The pressure to engage in “little white lies” can be very high, but you wind up paying a real price for it in this kind of situation.

  35. MashaKasha*

    So for #2, I once worked with a guy who got escorted out the door minutes after sending out his resignation letter, specifically because of how he handled his resignation letter. He’d meant to give a two-week notice, and was not happy to have to leave two weeks early. Here’s what he did wrong (from what I remember – that was back in 2000).

    – He sent it to the entire division. We are talking a couple thousand people in multiple locations across North America. We are also talking everyone up the chain, up to and including the CEO. This guy had just started working at the company a year ago in a programmer/analyst position and nobody had any idea who he was.
    – He made it more verbose than it should’ve been and somehow conveyed the message of “you guys suck, I found a place that sucks less, so I’m leaving you and going there”. Don’t remember the specifics, like I said it’s been a while.
    – He also named a teammate in the email and told everyone (2000+ people including the upper management) to “please start reaching out to him for all of your teapot problems”.

    Somehow all of this combined led to the management deciding that the guy needed to leave, like, NOW.

    IME, a resignation letter needs to go out to as few people as possible, and convey two pieces of information that are relevant to the business. 1) that you are leaving, 2) your last day. That’s it. All business, nothing personal.

    1. Gaara*

      It sounds like he also resigned by letter? Which is an additional mistake — it’s a housekeeping thing you do after you have already told your boss, in person, that you are leaving.

  36. BookishMiss*

    #4 – I once looked at a supervisor who continually misused a word, and, completely deadpan, told him, ‘you keep using that word. I do not think it means what you think it means.’

    We had a severe giggle fit and conducted the rest of our shift in Princess Bride quotes. You might try addressing it with humour, if you have that kind of rapport. Worked for me, and it’s one of my favorite memories from that place.

    I also had a manager (same place) consistently discuss ‘servicing the members.’ Much eye contact was avoided, much laughter happened later. None of us had a rapport that would let us address it…

  37. HannahS*

    Don’t do the tutoring. I tutor, and my boss asked me to tutor her daughters and it caused me a lot of stress. We couldn’t agree on price, she lives majorly out of the way, she laid a pretty passive-aggressive guilt trip, she underpaid me by accident…no joke, this was over the course of two days only. That evening I wrote a polite email telling her that I wouldn’t be able to tutor the girls and then a few hours later she sent me an email informing me it wouldn’t work out. Then I felt like, “You can’t dump me! I already dumped you!” even though I know she’s just disorganized. Yeah. It didn’t endear us to each other.

  38. Liz*

    Letter 1: When I worked as a tutor, there was a non-compete clause. Even if you don’t have this, you could cite this as a reason.

    1. SpaceySteph*

      I saw this mentioned upthread as well. I think that this just opens the door for more bargaining on the part of the boss– “what if you do it for free as a favor to me, then?” or “what if I go through your agency and request you?” etc. Even if the non-compete rule is true, it seems like AAM’s wording leaves less room for that kind of debate.

  39. OP3*

    OP 3 here
    Many thanks to everyone who has taken the time to respond to my dilemma. Since writing, I noticed (completely by coincidence) that our work’s version of Microsoft Word lists “overlook” as a synonym for scrutinize. Which I was really surprised about, as it’s not a usage I have been familiar with before now. Even though language develops over time, as far as I can tell most people still assume “overlook” means to forget. But now, I feel even less inclined to point it out to my manager, lest he use the Microsoft listing as proof. I mean, who am I to argue with Microsoft?!

    1. animaniactoo*

      It’d be pretty easy to say “I think this word is commonly misunderstood, for clarity’s sake, you might be better off with “overseen” or “examined”.” and they’re you’re not arguing with whether it’s technically correct, you’re just discussing common usage and making sure that the people he’s getting across what he’s meaning to say.

      1. Turtle Candle*

        Yep. “That word has a couple of different meanings, some of which aren’t at all what you intend. It might be better to use [alternative]” is a great, non-judgmental, polite way to suggest this, even if technically it can correctly be used in multiple ways. (I have these conversations all the time, since my work is such that it’s more important to be clear than correct. It’s nice to be both, but if I gotta pick one, it’s clear.)

  40. EmmaLou*

    #3 It isn’t a mistake though. One of the meanings of “overlook” is indeed: “superintend, oversee.” It’s not a common usage, but it is a correct one. So perhaps suggest that most people see it in its most common usage of “ignore”, while recognizing that he is still technically correct.

  41. ladydisdain*

    A former boss would send out this sheet listing the expectations for when big bosses are in town.

    Unfortunately he referred to ’emasculate’ landscaping.

    After a couple of times I had to tell him. My vicarious embarrassment wouldn’t let it continue.

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