I’m dating my boss — can I fix his conflict with another employee?

by Alison Green on March 23, 2022

A reader writes:

I work part-time for a small company owned by my domestic partner, Sam. We were together before he started the company about 10 years ago and it mostly works out for everyone because we have our own areas of work. Everyone who works there, including myself, is a 1099 contractor due to the nature of the work (actors/musicians).

Yesterday I asked an artist (Doug) if he would consider swapping out of a gig he had booked at another company to help us out. I never ask this of any of our artists unless it’s a true emergency, and I was careful to word it so that he knew if it wasn’t possible, it was fine. I’ve known him for years, and since I am always quick to say yes when he needs to skip rehearsals to work for higher paying jobs, it seemed like it wouldn’t hurt to ask.

He responded by sending me a long email explaining how offensive my request was since Sam hasn’t paid him for his last month’s jobs. I was caught off guard because I had no idea. In fact, I remember Sam telling me the check had bounced and asking me to bring it in-person to give Doug at a rehearsal … but Doug called out sick that night so I couldn’t. I didn’t hear any more about the check from either of them and figured they had sorted it out since they talk almost weekly about an arrangement where Doug uses our rehearsal hall for free.

Sam was cc’d on Doug’s email to me, and I was at my other job so I didn’t respond right away.

Unfortunately, Sam saw it and responded quickly and with a fair bit of defensiveness. He told Doug that Doug should have reminded him about the check since they speak so often. This escalated the situation and the two of them went back and forth over email, ramping each other up until Doug announced he would no longer work with us. This is devastating because he is a friend of mine and is also crucial to several upcoming events.

Sam, who does have a touch of a temper, has been vacillating between large waves of remorse and anger. He has decided the remorse he feels is only because of *my* reaction to the whole thing (I told him he handled it poorly) and that it isn’t true remorse since he still believes he did all the right things and Doug was out of line. He doesn’t feel like he can reach out and talk to Doug since he still thinks Doug was in the wrong. There’s a bit of trauma on both sides because Doug accused Sam of being “manipulative” by asking him why he didn’t just remind him about the money. Meanwhile Sam keeps asking me, “And when am I allowed to have feelings of my own and not get walked all over?”

I am directly impacted by Doug’s absence, as well as what this may do to our reputation if he only tells his side of the story to the small community of artists in our city. What can I do to patch things up? Can I reach out even though he says he’d done talking about it? What can I say without throwing Sam under the bus (even though I think Sam and Doug are both equally to blame for all the escalating that went on in the email thread)? I feel awful because if I just responded to the first email and deescalated things, I don’t think we’d be in this situation.

You are blaming yourself for something you didn’t cause, and trying to take responsibility for fixing something that isn’t yours to fix.

“I feel awful because if I just responded to the first email and deescalated things, I don’t think we’d be in this situation” is upsetting to read. Sure, if you’d happened to see the email earlier and responded before anyone else did, maybe you would have deescalated things. But you’re not responsible for Doug and Sam getting into it with each other in the way they did, and you shouldn’t need to be glued to your email in order to prevent altercations like this. That’s not your job, and it’s not reasonable to expect of yourself. I’m sure you wouldn’t expect it of someone else if they were in your shoes.

Frankly, it sounds like Sam is most in the wrong here, since he’s responsible for what started all of this — not paying someone for their work (a bounced check is non-payment) and then not bending over backwards to ensure they were paid as quickly as possible once he realized there was a problem. I get that he and Doug talk often enough that it probably didn’t feel urgent to him — but as a manager, Sam needs to take other people’s money seriously, even when he thinks he has some grace because of their relationship. Should Doug have followed up with him about it? Sure, that would have been helpful. But this was Sam’s responsibility and Sam is the one to blame for not ensuring it was fixed.

Moreover, once he realized Doug hadn’t been paid yet and was upset about it, Sam should have apologized profusely and assured Doug he was taking care of it immediately. It’s worrisome that his instinct wasn’t to do that and instead was to argue with Doug — Doug, the person he still hadn’t paid! Doug, the person who was rightfully upset about still not having his money and who was drawing reasonable boundaries around his labor!

Ideally you wouldn’t play any role here. It’s not your mess, and it shouldn’t be on you to smooth it over. But if you feel you need to do something, you can try telling Sam he’s wrong. And you can call him out on asking, “When am I allowed to have feelings of my own and not get walked all over?” … and point out that someone insisting on getting paid is not “walking all over him” and no, he shouldn’t be having hurt/defensive/angry feelings about someone setting reasonable boundaries around their labor when they still haven’t been paid. You can also encourage Sam to work on removing his ego from situations like this, because it’s (a) preventing him from seeing things clearly and (b) harming his business by causing drama and disruption. (Also, has Doug been paid yet? If not, another thing you can do is tell Sam that needs to happen ASAP.)

Please do not contact Doug to apologize on behalf of Sam or to try to convince him to change his mind. Doug drew reasonable boundaries and they should be respected.

Beyond that, it would be worth looking at whether your personal life is overly entwined with your work life! I realize that’s very, very common in the arts … but wouldn’t your quality of life (both at work and at home) benefit from some professional separation so that you don’t feel you’re responsible for Sam’s work decisions or worry that how you’re perceived is tied up with how he’s perceived? That would be true in any case where you’re involved with the boss, but it’s especially true if your partner has a temper … and especially if you find yourself trying to smooth over the effects of that temper. The more separation you can put between your professional lives, the happier you’re likely to be.

Read an update to this letter. 

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{ 218 comments }

{ 218 comments… read them below }

  1. Ask a Manager* Post author

    Hey all. There’s a lot of temptation with this letter to give relationship advice, which isn’t what the letter writer came here looking for. Please do not leave comments telling her to leave Sam or calling someone she loves “awful,” etc.; we do not have the full picture of their relationship (nor should we on a work advice blog) and that’s not likely to help her at this particular moment in time. Thank you.

  2. Chairman of the Bored*

    This is Sam’s fault and Sam’s problem to fix and/or deal with.

    Pay your contractors on time, if something goes wrong with that resolve it immediately without expecting them to remind you about it or otherwise pursue the payment they are due. If business fail to do this the contractor is well within their rights to tell the client to get stuffed and refuse to help you or work with them in the future.

    Doug is doing nothing wrong, LW shouldn’t get involved at this point.

    1. KayDeeAye*

      Yeah. Just…do what you can to get Doug his money. That’s the most important thing here. If Sam and Doug can work out their differences *on their own*, great. But first, Doug has to get his money!

    2. Ash*

      Seriously. The issue of paying someone what they’ve worked for doesn’t magically disappear because they called off one day. It’s not like you have one precious opportunity to have this important conversation and if you don’t, it’s ~gone forever~. Pay people what they work for. And don’t put *them* in the position of having to ask for their payment when you know it’s due. This issue is so uncomplicated that I really don’t blame Doug for simply dipping, especially if he has the means to do so. What a mess.

      1. Zombeyonce*

        I also wonder if this is the first time a check from Sam to Doug has bounced; this may have just been the last straw with Sam’s belligerence compounding the situation. If that’s the case, Sam is even more in the wrong for not fixing it immediately.

    3. Cait*

      This makes me think of the letter where the boss (OP) was upset because a wrongfully unpaid employee was complaining that they weren’t paid. It boggles the mind that people think employees/contractors need to just be grateful they’re working and shouldn’t put so much stock in things like, y’know, being paid for that work. Sam is so so so so in the wrong.

      3. Lily of the Field*

        That is honestly one of my favorite letters, just because of the sheer effrontery of the LW. I mean, come on; this employee was not being paid for like two months, and the LW was offended that the employee was upset! I just can’t even sometimes.

        1. Dr Sarah*

          I know! And the sheer hypocrisy of complaining that the employee wasn’t being financially responsible, when the company was repeatedly screwing up with paying the money they actually owed! I mean, *someone* is clearly being financially irresponsible in that scenario… but it ain’t the OP.

    4. Falling Diphthong*

      Pay your contractors on time, with checks that don’t bounce.

      If you intend to hand someone a check when you see them Tuesday, and then you don’t see them Tuesday, put the check in the mail on Wednesday.

      “You didn’t remind me enough times that I still haven’t paid you for the work you did two months ago” is… Yeah, not how you get me to agree to another gig.

      1. Elizabeth West*

        Yes, and then LET THEM KNOW. “Hi, we missed each other on Tuesday so I mailed your check on Wednesday to X address. Please let me know when you receive it, thanks.”

    5. TinaTurner*

      What struck me is LW being so sanguine and blase about the check BOUNCING. That makes me think it’s not such an unusual occurrence. OR that it’s the attitude there — not taking it very seriously.
      It’s not about the personal relationship here, it’s about the attitude toward workers.

      1. Marzipan Shepherdess*

        Yes, that jumped out at me, too! “Sam” does not sound very professional (or very mature), and it also sounds as if that business could be in very real financial trouble. Keep your ears open, OP – this just doesn’t seem to be a very stable situation.

      2. Letter Writer*

        Sorry, it bounced back to us because Doug moved and didn’t update his address with us.

        1. Ask a Manager* Post author

          Whoa, wait — that is not a bounced check! Do you just mean the mail was returned to you? Bounced check means there were insufficient funds in the bank when he tried to cash it, which is a much bigger deal.

        3. Brightwanderer*

          Oh, that changes things a lot – to the point where I wonder if it’s worth Alison editing the letter or making a note? Just looking at the comments it’s clear that the consensus understanding of “the check bounced” is “the person who wrote the check didn’t have the money to honour it”, and places the blame squarely on the issuer.

          2. MsM*

            I feel like the problem still lies with Sam if the check was returned directly to him and he did nothing about that because Doug didn’t bother asking. If Sam *tried* to get an updated address and Doug didn’t respond, that’s different. Or if it just vanished into the postal network somewhere and Doug never followed up…although even in that case, I feel like Sam should be on top of cash flow enough to reach out and see whether Doug got if it hasn’t been cashed within a certain timeframe.

            1. MCMonkeyBean*

              Sam didn’t do nothing though, he apparently had OP bring a new check to a rehearsal Doug was supposed to be at but then Doug was out sick so didn’t get that one either. I can’t tell from the letter whether or not he knew that check didn’t make it to Doug, or if at that point he thought it was taken care of.

              To me it doesn’t sound like any one party acted egregiously before this blowup, and based only on the information in the letter I would have to agree with Sam saying that Doug should have reminded them that he hadn’t gotten that check yet. But I would also agree with Alison that Sam should have also been more apologetic and promised to fix it ASAP even if he didn’t think he had done anything wrong because well, money is important to people who work for you!

              I am curious whether payment is a chronic issue or not because to me that has a huge impact on who is being more unreasonable. If this is a one-time occurrence then it seems like a bizarre overreaction for Doug to get that made at OP and say it is “insulting” to ask whether he is available for more work due to this one-time thing. If it’s a chronic issue then he had probably reached the end of his rope.

          3. pancakes*

            That’s the dictionary definition of a bounced check, and the legal definition as well. Commenter consensus isn’t nearly as authoritative! I’ve encountered multiple people here who thought a “cold call” means an unscheduled one, and one of the letter writers in another post today described herself as a “busy body” when she seems to have meant she likes to keep busy.

        5. Boof*

          That changes things quite a bit in my mind; if the employer has made at least two attempts to pay and has been unsuccessful because of factors on the employees end, the ball does start shifting to the employee to address how to actually pay them; still sam would do well to put personal feelings aside dealing with employees in a professional capacity and keep the focus on just getting things done rather than a blame game

    6. Lucille Bluth*

      But the OP was supposed to deliver the check at rehearsal, Doug wasn’t at rehearsal, and they apparently didn’t do any follow-up to confirm that Doug hadn’t received the check? Why didn’t OP tell Sam that Doug still needed his check? That would have solved the whole situation.

  3. Dr. Rebecca*

    Yikes on bikes. OP, I’m going to differ from Alison’s response a bit–you say you couldn’t give Doug the check because he called out sick from that rehearsal, so…have you been walking around with this guy’s paycheck in your (metaphorical or actual) pocket for a while now? Presumably you’ve *also* seen him since, why didn’t you pass the check then??

    1. Ask a Manager* Post author

      I don’t think that’s the case since she said she assumed they’d taken care of it themselves; I don’t think she’s had the check the whole time.

      1. Dust Bunny*

        But OP doesn’t say that they told Sam about it and handed the check back, so . . . did OP just assume that Doug would take this up again when he still wasn’t paid?

        2. EvilQueenRegina*

          Could have been that OP knew Doug had called in sick before setting off, so never actually took the cheque to the event.

          1. Lea*

            It seems like somebody should have simply texted Doug, told him the check was at the office to be picked and found times that work.

            I truly don’t understand why this wasn’t done

            1. Starbuck*

              Likely there’s no “office” or place of business that’s staffed or set up in a way that would make this possible. They are bouncing checks after all, which is a huge yikes!!

              1. CatPrance*

                Well, no — what OP explains above that what was meant was that he’d moved and the check “bounced back” to the return address (theirs).

                When I first saw “bounced check,” I thought huge yikes, too! But it was a different situation.

              2. Kal*

                Even if they have no set office or such, a text or message would still have fixed so much of this. Something like “Hey, I have your check, let me know when you can meet up to pick it up or I’ll bring it to our next meeting” coming from Sam would be enough to make sure Doug knew that its not an issue of it being forgotten or withheld in any way, just a matter of the logistics of meeting up, to prevent this sort of stewing. (Though I personally suspect that this one late check was not the only issue here – it wouldn’t normally be enough for this sort of outburst.)

                But none of that changes that I absolutely agree with the advice that the LW should stay out of it and let them deal with it between them. Since Doug being unavailable affects their work, I would suggest trying not to hope that it will be fixed. It sucks to suddenly lose a worker that was booked for things, but it could have happened due to an illness or a family emergency or all sorts of reasons, so it makes sense to treat it the same way as if one of those things had happened.

                And veering more into the relationships side of this conflict – if LW is hanging out with Doug, since they are friends, studiously avoid discussing it at all, and just say that it is between him and Sam if Doug does bring it up. And if Sam is unhappy with hearing LW’s opinion and advice on the situation, do the same with him. And that leads back to the other part of the advice – knowing that this is how Sam has handled this workplace conflict, do you want to still be working there? Do you want to instead focus on your other job or look for extra work elsewhere so that you don’t have to be in a position where its so hard to sit back and watch this all go down, or to make sure the income for the household is more diversified so that business decisions Sam makes don’t feel as dire for the household’s budget? Whatever the answer to those questions, taking the time to figure out what you want can help you feel more control without giving in to the urge to try to fix everything on Sam’s behalf.

        3. Myrin*

          “But OP doesn’t say that they told Sam about it and handed the check back”

          I think that’s pretty strongly implied though, isn’t it? It wouldn’t make much sense for OP to think Sam and Doug would sort this out between themselves if she had let Sam believe that Dough had received the cheque that night. OP blames herself for not immediately responding to an email, do you really think she wouldn’t have mentioned if she had forgotten to mention anything about the cheque?

          This whole thread reads astoundingly nitpicky in a “Spell out every single step you took!” kind of way.

          2. Triplestep*

            This isn’t nit-picky. My brain actually paused at this point when reading the story and I thought to myself “Well, what happened to the check?” I hadn’t even gotten to the end yet where everything blew up! It’s an important detail, especially if Sam thought Doug had been paid.

            The advice here really should not have been “Don’t get involved in this dispute” but “Don’t offer to bring checks to other employees or do anything that only their managers or the business owners should do.”

            2. Myrin*

              Again, literally nothing in the letter indicates that Sam thought Doug had been paid.

              I feel like we have to agree to disagree on the importance of this detail – it’s one detail of about-equal-importance-to-several-other-details to me and others whereas it seems to be the crucial point to you and others.

              But most of all, I really feel like I need to reiterate: “OP blames herself for not immediately responding to an email, do you really think she wouldn’t have mentioned if she had forgotten to mention anything about the cheque?”. If we’re looking only at the cheque part of the letter, this is really the thing that seems like the salient point to me.

              1. Ask a Manager* Post author

                Agreed, thank you. If that’s not obvious to others, I’d ask that you at least accept that it’s an unknown, it’s been flagged, and no one needs to keep criticizing the OP for it (especially because it’s highly likely that if she weighs in, it’s going to turn out she did indeed let Sam know).

        4. Cj*

          I assume that he called in sick before the OP was ever in possession of the check, so she never had it on her.

        5. Medusa*

          Why would OP need to go into this level of detail for this letter? We can fill in the blanks and assume that they told Sam that Doug wasn’t there

        6. MCMonkeyBean*

          Yeah, it seems like maybe there was a lot of assuming from all parties about something that could have been cleared up very easily.

      2. Just J.*

        I agree with Alison. One would assume that the OP would not have written in if she were given complete and absolute authority on delivering the check to Doug. I read this as, she was asked as a favor to deliver the check, which she was not able to complete. She gave the check back to Sam to deal with.

        I also don’t think that the OP would have written in if she were the accountant or bookkeeper. If so, she would have taken care of this. Since it didn’t get taken care of, I am assuming that Sam handles the books.

    2. lizesq*

      This. Sam delegated this payment to OP, OP missed the first opportunity and just thought… what? Doug doesn’t need to get the check you’ve had for a month because he missed a day? There’s responsibility on the OP there too; they literally were giving the job of getting the check to Doug!
      Also, if Doug has been using your rehearsal space for free, I kind of get why Sam is annoyed that Doug couldn’t just say something about what’s owed to him.
      Sounds like you all need to be better at communicating.

      1. The OTHER Other*

        I think that vast bulk of blame here has to go to Sam. OP was not “literally given the job of getting the check to Doug”, it was a favor, an unable to be done because Doug wasn’t there that day. It’s Sam’s business, he hired Doug, it’s his responsibility to pay Doug, no one else’s.

        I can’t agree that it’s an employee’s responsibility to repeatedly remind an employer to pay them. Bouncing a paycheck is a BIG deal! Doug is absolutely right to be pissed about it. But while I agree he could/should have said something, it’s understandable why he wouldn’t–Maybe he doesn’t want to make waves with his employer, plus it’s awkward to ask people for money owed.

        This could definitely damage Sam’s business, but that’s a natural consequence of first bouncing someone’s paycheck (did Doug get hit with fees for that? Probably!) and then blaming them for not reminding them about it. Paying your people needs to be a high priority, failing to do so is the hallmark of a failing business, and for good reason.

        I hope Doug gets paid, including for any bounced check fees, and not with another dubious check, either–in cash, or a cashier’s check. He deserves an apology, also, but all this needs to come from Sam, not OP. But it sounds as though Sam is digging in his heels.

        1. Humble Schoolmarm*

          OP clarified above that the check didn’t bounce as in insufficient funds. It was sent in the mail but didn’t arrive because Doug had moved. Not to say this makes Sam any less responsible for making sure it got there in the end, but at least there are no fees involved.

          1. CatPrance*

            And there wasn’t any carelessness about bank balances or inadequate funds to cover Doug’s pay.

            And the issue with the address change may not have been Doug’s fault, either. I’ve had really peculiar things happen with my mail when I moved and gave the Post Office a forwarding address.

      2. Jennifer Strange*

        Saying “Hey, you’ll see Doug before I do since he’ll be at rehearsal tonight, so bring his check to give him” is not the same as saying “Hey, I’m assigning you the task of getting Doug his check.”

    3. Fugnuggets*

      I read it was more like the check wasn’t actually written out since Doug called out sick that day (which he would have done in advance).

      2. Antilles*

        I don’t see how that matters. When OP agreed to get Doug the check, that means you get Doug the check.
        If he comes in that evening, you grab the checkbook, write out a physical check and hand it over. Easy peasy.
        But if Doug calls out sick, then guess what: You still need to get Doug a check. Email/text him and ask how he wants it delivered, THEN you grab the checkbook, write out the physical check, and get it to him.
        Especially since the previous check to Doug bounced (!), you really need to do whatever it takes to get that check in his hand.

        1. Ask a Manager* Post author

          Unless there are details left out of the letter, this isn’t on the OP. If Sam says, “I need to pay Doug and you’re going to see him tonight so could you give him the check?” and then Doug isn’t there, the obligation to find another way to pay Doug has not been transferred to the OP. Her only obligation is to let Sam know he wasn’t there and so she couldn’t hand him the check. Then it reverts back to Sam to handle.

        2. kiki*

          I don’t agree. OP volunteered to give Doug the check because she would be seeing him that night in person and Sam wouldn’t be. Doug wasn’t at practice, so OP was really just responsible for conveying to Sam that she wasn’t able to give Doug the check that night and the task would resume ownership by Sam. She volunteered for a one-time favor because she would be in the correct place to do so, not permanent ownership of the task.

          1. Humble Schoolmarm*

            I think this is one of those areas where things get blurry because of the work/personal overlap. It isn’t clear (maybe not even to OP and Sam) whether this is a “My partner asked me to do them a favour for convenience, but it turned out that I couldn’t” or “My boss told me to get this check to the contractor asap”. Both seem equally plausible in this situation, but make a huge difference in terms of how responsible OP should probably feel.

        3. What the Jorts?*

          >>>When OP agreed to get Doug the check, that means you get Doug the check.
          If he comes in that evening, you grab the checkbook, write out a physical check and hand it over. <<<

          If you're Sam, yes. Sam owns the business. OP does not, and presumably has no authority to sign checks on the business/payroll account. It's on Sam to ensure that Doug is paid.

      3. Letter Writer*

        Yes, this. The check that came back to us due to Dough changing addresses was cancelled. A new check wasn’t written the night of rehearsal because he called out sick and he was meant to get a check at the next show.

        1. Cthulhu's Librarian*

          Letter Writer, assuming the best of intentions here, Sam forgot to pay Doug after having not cut the check when Doug wasn’t at a rehearsal.

          Mistakes like that do happen. But Sam’s response to that mistake needed to be “I’m terribly sorry that happened Doug, I’ll send you the check by next day mail. Can you confirm your address for me?” He doesn’t get to have emotions beyond remorse in this case, because he has failed to meet his obligations to a contractor. The contractor was angry? Doesn’t matter, Sam can’t feed back into that, because HE IS IN THE WRONG.

          A check is an admission of a debt that you owe someone else, and when it doesn’t get delivered, or can’t be cashed, there is no distinction on the side of the person it was made out to between whether you are choosing not to honor that debt, or are unable to do so. When a bad check situation goes on this long, it is natural for the wronged party to assume you are wronging them intentionally.

          Maybe that’s what you need to say to Sam?

    4. SomebodyElse*

      This was my question rereading the OP, it really isn’t clear what happened to the original replacement check.

      I could see the LW, giving the check back to Sam and saying “Hey I didn’t see Doug tonight so wasn’t able to get this to him.” then yes, I agree that Sam should have contacted Doug and gotten the money to him somehow.

      But if the LW didn’t see Doug that night and didn’t mention it Sam. Then yeah, that’s not great and Doug wouldn’t be wrong to be as upset as he was.

      With both of those scenarios though, I think this doomed to be a drama-rich environment. And my advice would be to just step well away from Sam and Doug’s argument. Yes you may have unwittingly started it with your request to Doug, but it veered far far away from that topic with Doug’s initial response. If you worked in an office with a boss who was not your partner and a similar scenario played out, you’d have no standing to get in the middle of it.

      At most the only thing you can do is respond once with something along the lines of “I apologize if my request came across as insensitive, I wasn’t aware there was still an issue with your check. I can understand how my request was not ideal in this situation” since you do seem to be sorry you accidently lit this fuse.

    5. MistOrMister*

      OP says: “I remember Sam telling me the check had bounced and asking me to bring it in-person to give Doug at a rehearsal … but Doug called out sick that night so I couldn’t. I didn’t hear any more about the check from either of them and figured they had sorted it out…”. Granted, I am making some assumptions here, but based on what OP has written, she seems very conscientious. So my read of this is she never actually had the check in the first place. Because otherwise why would she say 1) she didn’t realize Doug hadn’t been paid and 2) she thought Sam and Doug had handled the payment if she knew she’d had the check in her possession the entire time? In that case, I would imagine OP would have emailed Sam and Doug both apologizing and saying she had the check and forgot to follow up and get it to Doug. I suppose it’s possible OP could have been holding the check the whole time, but that seems improbable based on the information in the letter.

    6. Shirley Keeldar*

      Honestly, both OP and Sam read to me as pretty cavalier about Doug’s payment…but Sam has the greater culpability since he’s the one who actually owed the money.

      OP, I’m also in a creative field and the dismissive attitude of people who are happy to take my work but slow and inattentive about paying for it is so painful and aggravating and humiliating; you have no idea. Nobody should have to beg or nag for payment that’s due to them. Nobody should act surprised or insulted that someone wants to be paid for work. And both of those things happen All The Time.

      Doug’s right. Sam’s wrong. Sam can have all the feelings he wants about that (it’s embarrassing to be caught in an error, I get it), but his feelings don’t make him any more right.

      1. Falling Diphthong*

        Nobody should have to beg or nag for payment that’s due to them.
        This. OP, this is why Doug doesn’t want to work for you anymore. Immediately paying him, combined with an apology, might salvage something. Asking him to empathize with you or Sam while he still hasn’t been paid just isn’t going anywhere.

        1. Letter Writer*

          Hey! OP here!
          To clarify some things:
          1. The check didn’t bounce as in a faulty check. The check bounced BACK to us because Doug had changed his address so the payment didn’t go through.
          2. Doug got paid within hours of sending his angry email. A check was written out and left at the box office for him to pick up.
          3. Sam wrote an email saying where his money would be and that it was 100% Sam’s fault and he apologized profusely. But he also asked why Doug just hadn’t mentioned it until now since they talk all the time.
          4. Since that check came back to us Doug ALSO rec’d payment for another project from Sam but it was hand delivered. So it’s not like we’re withholding payments… and we both thought it was weird that Doug didn’t say anything THAT day either about the older payment that was outstanding.

          1. TreeFrogEditor*

            Hi OP! Thanks for engaging and offering clarification! The “check didn’t actually bounce” thing makes it much clearer why you/Sam felt like more of this situation fell on Doug’s shoulders.

            To me, it feels like you’re struggling with two conflicting impulses: A) wanting everything to be peaceful again and for Doug to keep working with Sam’s company, and B) wanting Sam and Doug to each acknowledge the ways in which they were right/wrong in this situation (Sam didn’t handle this well and should have been more proactive in paying Doug, but it WAS kind of weird that Doug didn’t follow up, etc. etc.)

            The problem is that B) isn’t realistic — rehashing exactly who is more in the right in which context isn’t super productive at this point. And as AAM wrote in her response, A) isn’t really in your control — about the most you could hope to do is encourage Sam to smooth things over with Doug, if Doug is important to the business. That’s frustrating! It makes total sense to me that you’re looking for ways to positively influence the situation, since you’re so close to both parties. But I’m really not sure you can.

          3. Nonny Mouse*

            Re item #1, it might clear up some confusion to say that the check was returned as undeliverable. :-)

          4. Shirley Keeldar*

            OP, thanks for this clarification–it makes a huge difference that the check wasn’t actually returned for insufficient funds. I retract some of my harsh words. I was definitely influenced by the time a client’s check bounced (really bounced) and they repeatedly promised me a new check but never sent it, robbing me of a fee I really needed. In what you describe, there’s definitely more to the “faults on both sides” narrative that you presented–although it does seem to me that there’s not much you can do at this point.

          5. RagingADHD*

            When the check was returned undeliverable, the correct thing to do was to reach out proactively to Doug and make sure it was left at the box office (or wherever) to pick up, or be hand-delivered. Why did none of those simple solutions occur to Sam BEFORE Doug sent a nastygram about it?

            Does Sam not reconcile the bank statements? How does he not know that there are outstanding, uncashed checks floating around for over a month, and why isn’t he chasing them down?

            It’s good that the check didn’t actually bounce at the bank, but the whole story still points to very sloppy business practices. It’s actually rather surprising that the company isn’t bouncing checks right and left if Sam is so lackadaisical about the bookkeeping.

    7. June*

      I’m also wondering why OP didn’t follow up with the check. I don’t blame anyone for being upset that they were not paid.

  4. Amber Rose*

    You’re allowed to have feelings… but not about normal business transactions. Professional work is not the place to whine about your feelings. Especially when you made the error.

    Sam sure likes to blame everyone else (you, Doug) and refuse to take any responsibility for his own actions. Makes me wonder how that plays out in all the rest of his relationships and interactions, professional and otherwise. OP, do you often feel like you have to apologize for his behavior or take responsibility for what he’s done? Because that is a super flashy red flag.

    1. prismo*

      Right? I know this is a professional advice column, not a personal one, but yeesh. This made me worry about their Sam and OP’s relationship for sure. Definitely seems like a dynamic where she’s very kind and takes responsibility for Sam’s emotions, including his “temper,” and he takes responsibility for nothing.

      1. anne of mean gables*

        OPs statement that he “does have a touch of a temper” definitely made me make the Chrissy Teigen “yikes” face.

    2. Atalanta0jess*

      You can even have feelings about normal business transactions! You just can’t act on those feelings in a way that is totally jerky. (As you probably shouldn’t in other realms of life…) All feelings are ok, IMO…but all actions aren’t…

    3. Everything Bagel*

      Yeah, regardless of why Doug didn’t get the check, Sam didn’t make things right as soon as he knew. Sam’s feelings don’t really matter here, and all of his comments seem to be defensive when he knew or couldn’t admit he didn’t handle this right. Whether or not Doug continues to work for him, Sam needs to pay him that last check.

    4. Anne Elliot*

      This is actually a point I have had to reinforce repeatedly to teenaged daughters: I may point out that they have behaved badly, or failed in their responsibilities, or need to adjust their attitude/behavior (all falling under the umbrella “got into trouble”), and they want to re-focus that conversation on the fact that being chastised or corrected for doing something wrong makes them feel bad. “Can’t I just feel my feelings?!?”

      Yes. You can. You can feel your feelings while also fixing what you screwed up and/or dealing with the consequences of your actions. I also find it important to ask them to reflect on whether they feel bad because they did something wrong, or whether they feel bad that they got in trouble for it.

      1. Elizabeth West*

        Commenter TootsNYC posted something similar here a while back. The comment was also about kids, but I think it was really good advice in general for work. I saved it:

        TootsNYC
        June 25, 2018 at 1:08 pm
        One thing I said to my kids when dealing w/ situations in which their emotions were coming out inappropriately is this:

        You can feel what you want to feel. But it is not appropriate to express it. Other people don’t want to have to deal with all your emotions leaking all over the place. It’s not their job to deal with your emotions–that’s YOUR job. It’s rude to make other people give up their time and energy to deal with you like this. Now you need to figure out how to handle the expression of your emotions so that you aren’t dumping them on everybody else.

        My feeling is that Sam needs this.

  5. Office Lobster DJ*

    It sounds like Sam does just fine having Feelings of his own as it is, tbh.

    OP, the only role I see for you here would be if Sam didn’t know Doug was out that night and thought you had handed over the check. Even then, a sincere apology and dropping everything to get Doug paid would be all that was required of you. If the guys didn’t talk about it between them, that’s not your fault. Otherwise, both of these guys sound like they are enjoying revving each other up, and that’s their choice, I guess.

    1. Freelance Anything*

      ‘It sounds like Sam does just fine having Feelings of his own as it is, tbh.’

      +1

  6. Neurodivergentsaurus Rex*

    Oooof. You didn’t ask for relationship advice so I won’t give any, but I would definitely be reconsidering whether you want to keep working for your partner’s company. He doesn’t seem like the greatest person to be in business with.

    1. Not Tom, Just Petty*

      I agree. OP is asking how to make the business world easier to navigate for Sam, but does OP have a ready list of ways s/he makes the rest of the world easier for Sam?
      OP is not surprised that Sam blew up on a contractor. “He has a touch of a temper” is like “a little bit pregnant.” OP told Sam what he did wrong, good, but is now trying to clean up the mess.
      If OP were Sam’s admin assistant getting serious pay for this, hey, OP, you do you. Want to be a professional parent for a “generius” (a field specific genius who acts rashly then makes amends with cash and perks)? Go for it.
      But this a part time gig with your partner. And you are far too involved. Everyone is friends. Doug uses the studio for free. Sam pays with checks instead of direct deposit. You hand people checks.
      Please think about stepping back from working there and just being a partner and friend. It will be best for you.

    2. Pocket Mouse*

      Similarly, I wonder if OP feels inherently involved or that the interaction between Sam and Doug reflects on her professional role *because of* their personal relationship with Sam. It’s a pattern that OP may be falling into – women are often implicitly tasked with maintaining their male partners’ relationships, which is unhealthy in general and doubly so in the workplace.

  7. STG*

    I don’t like how flippant Sam is regarding a bounced check for payment to an employee. People leave employers for far less serious issues.

    1. Eldritch Office Worker*

      People pursue legal action against employers for far less serious issues! This is super concerning.

    2. The OTHER Other*

      That really bothered me, too. OK maybe this is a small business, and mistakes happen–but in every case I’ve heard a bounced paycheck is part of a long tale of woe. Often preceded by delayed paychecks and followed by business closure and owner disappearance.

      In the restaurant biz it’s a tale as old as time, and probably for performing arts gigs also.

      1. Orora*

        Yeah, as a part-time performer, I’m not shocked about a bounced check. It happens. Especially if the “business” hiring you is a producer of events who is basically a one-person show and living check-to-check themselves. I work with producers who produce at different venues and the venues each have different policies for paying performers. Sometimes the producer has to front money to pay the performers on their terms before they get payment from the venue/event. If the producer doesn’t have the ready cash, the check will bounce. It’s not an ideal way to run a business, but it happens.

    3. fhqwhgads*

      OP clarified it didn’t “bounce” in the sense we all seem to have thought. It failed to be delivered because Doug’s address changed. I hope Alison notices that comment and edits the original post or else everyone’s going to be misunderstanding that aspect of the letter.

  8. Dust Bunny*

    Yeah, this can be deescalated by paying Doug and apologizing profusely for letting it fall through the cracks, and then not letting it happen again, and that’s entirely on Sam.

    Sam sounds kind of high-maintenance, TBH.

  9. ferrina*

    So many red flags about Sam. Beyond the obvious (getting mad at an a contractor who wants to be paid) He: 1) blames you for his “remorse”, 2) refuses to acknowledge any wrongdoing, even that he made a mistake in not being on top of his finances (failing to pay a contractor in a timely manner) and 3) responds to a pretty standard disagreement as “not being allowed to have feelings”. Add into that you feeling like somehow this whole disagreement is your fault because you somehow should have stopped Sam’s outburst before it happened. You are not responsible for another person’s actions.
    I’m not so worried about the work situation- I’m worried about you, OP. Sam sounds manipulative and awful. Are you sure this is the kind of relationship you want to be in? You sound like a sweet, empathetic person who deserves better.

    1. Not Tom, Just Petty*

      I agree so much. OP is so inured to Sam’s manipulation, the go to, blame others is just a knee jerk reaction. This is not on Doug, even if he “uses the studio for free” and “we are all friends” and particularly, “ramping each other up.”
      I feel OP realizes that Sam is not right, and comes very close to saying it, then writes, “how do I fix it?”
      And that worries me.

    2. DANGER: Gumption Ahead*

      ^^^THIS!! Sam’s first check to Doug BOUNCED and Sam’s angry/having feelings???

  10. A Mom but Not Your Mom*

    OP are you sure this isn’t a sign of larger financial problems? Bouncing people’s paychecks and then…. just not following up is not a sign of stellar financial management. Bouncing one check can happen to anyone, but just not bothering to pay someone who has done work for you is a big deal, and the defensiveness about it makes me wonder how long before you are working for no pay as well, and just expected to take it because it would harm your relationship to insist. If Doug hadn’t asked again, would he have been paid? (HAS he been paid?) Your boss says he would have taken care of it if Doug reminded him, but Doug reminded him and instead of taking care of it, he went off on Doug. Nothing here is a good sign and I’m worried about you, OP!

    1. Rainy*

      I’m with you here–a bounced paycheck is not something to handwave off as a non-problem, and if that’s the owner’s position, the business is definitely either in financial trouble or legal trouble, or both. (Probably both.)

    2. Freelance Anything*

      This was my first thought, honestly. I have wider concerns regards this businesses financial situation.

      1. alienor*

        Back around 2007 or so, I would occasionally do a little light office work on the side for a relative who owned their own business. About three out of every four checks they paid me with bounced, to the point where I would deposit them like I was pulling a slot machine handle–“Let’s see what happens this time!” Sure enough, the business crashed and burned spectacularly a year or two after that.

    4. quill*

      Yeah, OP – even if everything seemed to be going swimmingly at this company, I would be wary of both you and Sam depending on the same small arts business for income. It sounds like you also have another job, but that it might not be enough if, for example, the business went under.

      The check bouncing is not a good sign for business stability.

    5. Loosey Goosey*

      Yeah. I get the an arts organization might operate on a shoestring budget, but bouncing paychecks should not happen. And if it does, the company owner should be VERY concerned and apologetic and make it priority #1 to get their contractor(s) paid. I’d be very worried if my paycheck bounced, and then royally pissed off if it seemed like the owner didn’t care about fixing the issue asap. Sam is 100% in the wrong here and his “little bit of a temper” is bad news.

    6. JuniorB*

      I work for a bank, and typically a depositor can deposit a bounced check one more time. So if a new check is required, it likely means that Doug (or Doug’s bank) had already tried to redeposit the first one. Not a good sign.

    7. TrixM*

      And while this might sound a little overwrought, I hope there are not any more serious financial issues that Sam is hiding from OP.

      I have friends who are a couple and one of them is a professional in a creative industry. She invested in some very expensive equipment to expand her business, but for some time, did not get contracts that leveraged that equipment or the higher rates she could charge for it. However, of course, it still needed to be paid for.
      It turned into a terrible cycle of her shuffling money from here to there in an effort to cover the earnings gap, including additional fees for short term loans. Due to embarrassment, she hid it all from her partner, who only tangentially involved in the business. The partner was temporarily earning less while working on her own project, in the expectation that there was no problem with the previously-good cashflow in the business.

      Unfortunately, after the best part of a year, it all came crashing down and it took help from partner’s (fortunately well-off) family plus more debt and some years to get themselves out of the hole. The original finance arrangements for the equipment had been via a legal-but-dodgy arrangement too (not unlike a bad franchising deal), adding to the complexity of sorting it out. Thankfully, the equipment did more than pay for itself in the end, she is very successful in that aspect of the business, and the family’s finances are more than healthy now.

      I really hope something like that isn’t bubbling under the surface, but if it is, it could also explain some of Sam’s general demeanor plus his outsized reaction and defensiveness about the situation. If it is something like that, he probably wasn’t intending to rip off his buddy, but it’s easy to forget the smaller things – paying friends might seem a little less urgent than other creditors – if you’re re-enacting Mickey Mouse’s plight in the Sorcerer’s Apprentice.

      Either way, he should make his apologies and sort it out asap, because this is exactly the kind of thing that gets around very quickly in an small industry that runs a lot on good will.

  11. Have you tried sparkling at it?*

    I’m not sure “domestic partnered to” is equivalent to dating. I don’t know a shorter term for it (to switch out in the title bc I know that has to be short) but you also said they’re dating in the advice text.

    I say this as somebody with a domestic partner, and our relationship gets erased in all kinds of ways, from “roommate” to “friend” to “dating”. We chose to be domestic partners for a reason.

    1. Dust Bunny*

      I don’t know that the specific degree of partnership matters here, only that the LW is intimately involved with their boss and apparently feels more personally invested in and responsible for him than one might if one were just an employee.

      1. Have you tried sparkling at it?*

        I don’t think it affects the advice here at all. I just care about the language used. It might be nitpicky, but it’s something that affects my life in a million small ways, that occasionally add up and become big ways. (For example when my insurance stopped covering my partner because somebody misinterpreted “domestic partnered” as dating, despite the fact that the policy explicitly covers domestic partners.)

      2. prismo*

        I think a matters a bit, in terms of their level of involvement. Domestic partners is basically equivalent to marriage so I think her concerns about his reputation affecting hers, etc., are much more realistic than they’d be if they were casually dating. It also means it’s harder for her to just walk away from the situation and implies their finances are entwined in a way they wouldn’t be if they were dating, so his business decisions have a bigger effect on her than they would otherwise.

        1. Velociraptor Attack*

          This is the big thing for me.

          My husband and I work in pretty different industries but there’s some overlap in terms of professional networking and we’re both pretty acutely aware that our professional reputations can easily impact the other. So I don’t think she can just walk away and say well not my circus, not my monkeys.

    2. Rosemary*

      Came here to say the same thing. “Dating my boss” has different connotations (to me at least) than someone who works with their long term partner (essentially their spouse).

      1. Coenobita*

        Right, I saw “dating my boss” and my first thought was “oh no, don’t date your boss!” – but actually, I think the situation is more analogous to “working for the family business,” where it’s normal/expected for people with close personal relationships to work together.

    3. Purple Cat*

      I don’t see where Alison used “dating” in the advice text. Was it edited?
      I get your concern on not minimizing the relationship, but it’s tough to complain about the headline while simultaneously acknowledging you couldn’t find a good alternative.

      1. Ask a Manager* Post author

        Yeah, I changed “dating” to “involved with” after the comment pointing this out. But yeah, I have no idea what else would work for the headline. As someone pointed out below, “partner” in the headline would sound like business partner.

        1. L.H. Puttgrass*

          “Can I fix my domestic partner’s conflict with another employee?”

          It’s not as punchy as the current headline, but at least it doesn’t use the word “dating.”

        2. Web Crawler*

          Maybe “involved with” works for the title too? Or “My boss is my domestic partner –” for the first bit?

          “Dating” feels a bit misleading, considering that the first line says “domestic partner”.

    4. Tiger*

      I agree with you, for the record. I think it must have been edited in the text (it says they’re “involved” and calls them “partners”- doesn’t mention dating).

  12. catsamillion*

    As a creative person who often does gig work/one-off jobs similar to what is described here, I would also never again work with a company that bounced a check and then got rude when I pushed the issue of payment. This could be a major reputation issue for this business, LW!

    1. Everything Bagel*

      Good point. Sam is concerned about Doug’s point of view getting out, but Doug’s point of view is the fact that Sam bounced a check and then didn’t immediately see that Doug gets paid. What other way is there to look at this? Sam’s defense that Doug should have reminded him is not a great reputation to have even if Sam is going to use that defense.

    2. Orora*

      YES! I’m a part-time performer, too. This is not a good look for Sam and the business. I know many artists that refuse to take gigs with producers/agents based on the professional interactions experienced by other artists. Bouncing a check was not ideal, but most folks would give you the benefit of the doubt if it only happened once. It’s forgivable. Sam being confrontational on top of the bounced check would be a big red flag to me as a performer that this is probably not a business that I want to work with.

      OP, be clear with anyone who asks that this is between Sam and Doug, and you are not involved. Be clear that this is a business matter between two adults and (as much as possible) don’t take sides.

    3. tangerineRose*

      I figure Doug is going to tell a lot of people about this, and they aren’t going to want to work for this company, either.

  13. lunchtime caller*

    I do think both the guys involved here brought way too much emotion to the situation, but Sam is by default more in the wrong since he was the one who owed money. I do plenty of work as a contractor and there have been times where recurring clients are late on money and ask me for more work, and I just explain that I’m unable to take on more from them until I receive payment on the old work. You have to track your own money carefully as a contractor because no one else cares as much as you do–I give a tiny grace period once my invoices are past due, but then I go knocking and explain simply that my records show X hasn’t been paid, can they please look into it, etc. There’s no need for a long email about how offensive something is–it’s just “pay me, thanks” in increasingly annoying but still friendly ways until you get paid, and then a simple rejection of future work if it keeps up.

    (but again, all that said, Sam needs to revamp how he sees his business–meaning take it much less personally–immediately)

  14. Sunny*

    Wait, OP didn’t pass on the cheque to Doug, and then did… nothing? I was surprised Alison didn’t pick up on this detail. Lots of missing info here. Like, did OP inform Sam that they hadn’t completed the task? Or tell Doug that there’s a cheque waiting next time they come in? This seems like a major ball to drop.

    All this on top of a cheque bouncing? That’s a major red flag and it seems Sam (and by extension the OP) isn’t taking this nearly as seriously as they should. No one paid Doug, and no one made sure that this was dealt with after the cheque bounced. Of course Doug isn’t going to work for you again, and of course he’s going to warn others.

    If this is all true, then I think both OP and Sam need to take a hard look at how they treat the people who do paid labour for them. I also wonder, based on Sam’s reaction if there isn’t something bigger going on, because to me, bounced cheque + anger at request for payment adds up to the business being in trouble.

    That said, I agree that Sam’s reaction is his to manage, and the OP isn’t responsible for two grown men having a tantrum on email just because she didn’t reply right away. Just there’s some missing details and maybe some bigger issues for OP to probe.

    1. WellRed*

      Sure the middle part of this whole nonpayment chain is vague, but the crux of it is, the check bounced, which it shouldn’t have, and then Doug(ie boy) a. Blamed Sam and b. Blamed OP.

    2. MistOrMister*

      My read of it is that OP never physically had the check in the first place. They said they couldn’t pay Doug because he called out and that afterwards they figured Sam and Doug had handled it themselves. I don’t think a reasonable person would take a check, not pass it on, not inform the owner that it hadn’t been passed on, but then expect the other parties were both aware of the nonpayment and were handling it. I think that also would have factored into the argument between Doug and Sam. Given how mad Sam got, I would think he would have told Doug OP had his check the whole time and it’s not his (Sam’s) fault Doug didn’t get the check. At least, that is what I get taking the letter at face value. I suppose OP might have had the check this whole time and just not have said so in the letter, but that seems unlikely. Because at that point the letter would be “I accidentally held smeone’s paycheck and now everyone is mad and how do I fix it” which would need different advice. Also, the business is Sam’s, so the other employees are not OP’s employees and at the end of the day, it isn’t her responsibility to make sure everyone is paid.

    3. Velociraptor Attack*

      Also, there was likely a bank penalty for Doug tied to the first bounced check…

      1. Carol the happy elf*

        My first boss was a doctor who was merging with a retiring doctor’s big practice. They changed banks, and several of the other practice’s staff took the lump payouts, retired, etc. The bookkeeper was new, and (pre-computer) had the wrong check folder, so our checks all bounced because the old account had been closed.
        My boss moved all his non-urgent appointments, changed the “can’t waits”, and figured out what the bounced checks had cost US in overdraft and NSF fees. He tripled that amount, and wrote each of us multiple copies of hand-signed letters each apologizing for HIS error, called each of our banks and credit unions, (there were over thirty employees involved)
        and had groceries delivered to our homes (pre-DoorDash) AND gave us gas money to make up for all the driving we might need to do. (Gas had recently gone through the roof, and it cost $11.50 to fill my 1968 VW Beetle!)
        Additionally, he made sure there was a catered lunch for the whole next week. With boxes for leftovers.

        THAT, boys and girls, is how you make amends for stiffing an employee.
        Not possible for Sam? Well, that’s still the bar to aim for.

    4. Beany*

      My read is that the first check bounced, and OP had either (a) a new check, or (b) some other form of payment, presumably cash, which they weren’t able to hand over to Doug.

  15. Sam is Not OK*

    Not addressed in the answer, but a lot of Sam’s behavior is abusive. If this is how he also acts at home, you need to break up with him. The National Domestic Violence Hotline can help you find safer ways to exit if you need help: 800-799-7233.

    1. ferrina*

      Thank you for adding this. This flagged as abusive to me as well. If you’re not familiar with emotional abuse, it’s a very real and very damaging pattern of behavior. It generally does not resolve and does not get better. Like physical abuse, there’s often a love-bombing faze involved immediately after the abuser acts out or when the abuser realizes that their victim is starting to pull away.

    2. Brightwanderer*

      I don’t agree with this take at all. A lot of Sam’s behaviour is on a common spectrum of behaviour that can vary from “difficult to be around sometimes” to “abusive”. Under specific circumstances, with specific other factors in play, it would play into and enhance an abusive situation, but to call it abusive, with zero other context, strikes me as inaccurate and unhelpful.

    3. MistOrMister*

      It wasn’t addressed in the letter b/c, as Allison pointed out, this is a work advice blog and she doesn’t want us trying to dissect OP’s relationship. There is absolutely not enough information provided in this letter for any of us to be able to say Sam is abusive and it’s not helpful to jump there.

    4. voice of experience*

      Thank you for sharing this. I didn’t think my relationship was abusive until I got a black eye, and that hotline helped me a lot in leaving. After I left, I realized a ton of things I went along with to make my partner happy really were manipulative and abusive. You never know what’s under the surface of a relationship unless you’re in it, and sometimes not even then.

  16. Wisteria*

    The fact that you work for your partner is incidental. There is a conflict between the CEO and a 1099 employee at a place where you are also a 1099 employee who has a role dealing the other 1099 employees. Ideally, Sam would come to his senses. However, since he is not, as an employee of a very small business who handles scheduling and other tasks with the other employees, you have standing to play a part in resolving the conflict. And while you shouldn’t have to, there is no harm to doing so. There is direct benefit to you of resolving this conflict with Doug, so don’t let what “should” happen in an ideal world interfere with what can happen in the real and somewhat-less-demarcated-than-you-might-prefer world. Have a word with your boss about how he should pay people on time and remind him of the benefits of having Doug as part of the business and the long standing relationship they have built up. If possible, it would be a nice touch if you and Sam went in person to hand Doug a check (I would actually do cash since the last check bounced) and when you hand it over, have a conversation with Doug about how much you value his contributions to the business and the relationship you have with him. Even Fortune 500 companies run on relationships, and small artistic businesses even more so. You didn’t cause Sam and Doug to over-react, but being part of their resolution helps you as much as it helps them, so do what you can.

    1. SM*

      There is no such thing as a 1099 employee. If the LW is an employee, Sam needs to employ them. The artists may legally be contractors, but without knowing more it’s hard to say. From what we know about Sam, I’d say there’s a chance other illegal employment practices are happening, which LW should be aware of because they appear to be the one engaging the non-employees in work on Sam’s behalf.

  17. Carrots*

    It’s kind of offensive to call this relationship “dating” in the post title. They have been partners for over 10 years! That’s more akin to a marriage. Dating is when you are just starting out, before you become official.

    1. anna-ish*

      I don’t know what other word would capture it in a headline, which needs to be short. “Partner” will sound like business partner.

      1. Have you tried sparkling at it?*

        If this isn’t something that affects you, you might not know how grating it is to hear your relationship get misinterepreted day after day. It’s absolutely something to speak up.

          1. Web Crawler*

            I’m not OP or the commenter, but I do have a domestic partnership. And the small things like this letter are something that’s easy to walk away from, but it all adds up over time to a culture of erasing domestic partnerships that’s very difficult to walk away from. And that affects my life in tangible ways. For example, options in official forms that make me choose between single and married, where my answers affect my income or benefits in ways that I can’t always predict.

          2. Have you tried sparkling at it?*

            That’s where privilege comes in. Because it is personal, in the sense that the public perception of domestic partnerships is what kept my partner from getting covered under my insurance (despite official policy), keeps her job from recognizing our relationship at all, and makes people assume time after time that we’re not committed to each other.

    4. breamworthy*

      Maybe this perception is partly depending on where folks live. It feels like minimizing the relationship to me as well. This is relevant because if the business is in financial difficulties, she could be legally affected by that in ways she wouldn’t if they were just dating. Where I am, they would legally be considered married. Common law here happens automatically after a couple of years (sooner if you have kids together) and is legally indistinguishable from marriage. It’s also really common for long-term partners not to be officially married. My husband and I have lived together for 17+ years but never had a wedding ceremony, and no one would ever call him anything other than my husband or say we were dating rather than married.

    5. Alpacas Are Not Dairy Animals*

      Ok, no. I’ve been with my partner for twelve years and we’re not married because I very specifically do not want to be married, it’s an institution I find objectionable. We’re not ‘akin’ to being married. We are dating, no matter how long we decide to do that.

      1. Nopetopus*

        And that’s totally fine for you and your relationship! But some of us who are domestic partnered and also disagree with the institution of marriage don’t prefer to be referred to as “dating” one another and do view it as akin to marriage in the sense that this commitment is for *life*, myself and my partner included.

        “In a relationship with” would even be a better alternative here (in the letter, not in your relationship!) as it implies something more serious than “dating,” which often implies a temporary thing.

  18. bee*

    So this whole situation is definitely Sam’s fault but as a freelancer I am a little side-eyeing Doug here. There’s definitely a pretty standard series of escalation when a check is late/wrong, and going from no follow up (especially when you’ve interacted regularly with the person who owes you!) to a complete blow up feels like skipping a ton of steps, and many opportunities for resolution.

    And yes, places always Should pay you on time and you Shouldn’t have to follow up, but in my experience that is often not the case, and I would expect a stronger and more professional sense of self-advocacy from Doug. Which does not exculpate Sam! But… it’s weird.

    1. Just J.*

      This. I am self employed too. I know who has paid me and who has not and how many days out its been. In my industry it is also very common for a sub-contractor (me) to not get paid until the main contractor gets paid. Sometimes all of that takes a while. 45 days out for payment is typical. But after 30 days, I start sending the reminders. I’m side-eyeing Doug a little as well…..but am assuming the blow-up is a result of longer standing issues……

      1. bee*

        Oh, yes! The idea of longer standing issues between Sam and Doug totally clarifies my odd feeling— I’m guessing that, due to past issues, Doug had reached a place of “I’m not gonna beg Sam for my money. HE has to bring it up.” And so all the in person interactions were just making Doug angrier and angrier. This doesn’t change the advice, but it does reinforce for the OP that this isn’t something they can blame on themself. Sam did something that deserved anger, and Doug was looking for an opportunity to be angry. Replying earlier wouldn’t have solved this, and if it’s going to be resolved, it has to be between Sam and Doug.

    2. Colette*

      Doug would have followed up with Sam, who is not the one who wrote in. It’s possible he’s followed up multiple times. (Sam implied Doug didn’t follow up, but it’s possible that Doug actually did.)

      1. MistOrMister*

        This would make Doug’s blow up make more sense. But since OP says Sam was insisting that Doug should have followed up about the missing check, it makes me think Doug didn’t say a word about it during their calls with Sam. This situtation is just weird. Doug and Sam both seem to be behaving like big babies.

        1. Colette*

          Or Doug followed up, Sam made excuses and promised he’d get the money, but didn’t consider that Doug followed up “enough” to get paid.

          1. Falling Diphthong*

            As a freelancer, this is where I land–Doug follows up, but not yet in the exact unknown-yet-perfect way that would result in a check that doesn’t bounce.

    3. Starbuck*

      It’s not just that Sam is late with payment…. he wrote a check that bounced! He doesn’t even have the money to pay Doug! And don’t most banks charge you a fee if you try to deposit a check and it bounces? That’s a whole extra insult. Did he even apologize or acknowledge when that happened? Doesn’t seem like it.

      My guess, the blow up happened because this is not the first time Sam has failed to pay Doug in full or on time.

    4. Student*

      The OP is not necessarily in a position to know whether that’s really how Doug handled this, though. It’s possible that Doug had gradually been escalating with Sam in an effort to collect payment. I know Sam said in a email that “Doug should have reminded him about the check since they speak so often” but given the way Sam handled all of this, I’m not sure he’s the most reliable source on the matter. At minimum, if that was the issue at hand, I’d want to hear Doug’s side of it before jumping to conclusions about how he handled it.

      The defensiveness from Sam, in particular, would make me concerned that it’s a cover for some more substantive issue. Getting defensive is meant to tweak everyone up emotionally and meant to misdirect away from the core issue of pay. In Doug’s shoes, I’d be worried that there’s some serious business issue hiding behind all of Sam’s anger at the root of why I hadn’t gotten paid.

  19. I WORKED on a Hellmouth*

    Um. OP? Does Sam do this kind of thing a lot? How often do checks bounce? Is he often defensive when someone points out something important that he has messed up? How many “feelings” does he spill on to people who work for him? And… how much guilt/responsibility for his feelings and actions does he typically assign to you? Because… none of that is good, OP.

  20. Omnivalent*

    So Sam bounced a check and then blamed the guy whose pay he bounced for not ‘reminding’ him to fix the problem? And in 2022, Sam couldn’t manage to Venmo or otherwise direct-pay Doug – or even to express mail the check – the literal only option for making good was to physically hand him a paper check? Unless you are all in the year 1990 and sending this advice request to us in 2022 through a rip in the space-time continuum, this isn’t a simple mistake by Sam. This is Sam stealing people’s labor in order to make his own numbers add up.

    You shouldn’t do anything, because you can’t fix this. Sam chose to bounce a check, not make good on it, and then get defense and combative. That’s going to affect your business in the community because IT SHOULD. Knowing that Sam doesn’t pay on time, drags his feet on making good, and then is an ass about? That’s information anyone wanting to do a gig SHOULD know in deciding whether to work with your shared business.

    1. Unaccountably*

      This is exactly what I was going to ask. Why does Doug have to be there in person to be handed a physical check? The money should be coming out of a business account. That account isn’t associated with any other payment methods? Sam can’t pay bills from it electronically? He doesn’t have Doug’s address from the 1099 forms so he can put the check in the mail?

      OP, it sure sounds like there is some doubleplus ungood financial shadiness happening at this company.

      1. wordle clone of the day*

        Even I, with my non-business account, can tell my bank to send a check to this person at this address at this date.

    3. Christina*

      My thought as well. I pay contractors via 1099 all the time. When I make a mistake, I go out of my way to get them the money – once I drove two hours out of town to hand someone a check because I didn’t have a bank account on file for them and I overlooked the payment – mail would have taken up to two days, so I drove. But honestly, most people are paid via direct deposit and I have multiple means of getting people money if I need to.

      It sounds like some of this is on Doug – that he didn’t update his address and wasn’t available when Sam had the check on him. But then Sam needs to be on the phone and emailing Doug with “I have your money, how can I get it to you.”

  21. Michelle Smith*

    I don’t know, I think if you still want to have a relationship with Doug or just want to do the right thing now, there’s no harm in reaching out and expressing that you didn’t realize he hadn’t been paid when you made the ask, you are appalled he wasn’t, and then ask him if he’d prefer to receive the money in the mail or to pick up the check in person. And make sure it happens immediately. He needs to get paid and you’d probably prefer to do that now rather than after he wins a lawsuit and the business is responsible for his back pay plus damages. And then you personally make sure it’s done so that he doesn’t have to interact with Sam ever again. Definitely no need to apologize for something that isn’t your fault or to try to cover for Sam or get involved in something where clear boundaries have been set. If he doesn’t respond or tells you to pound sand, send the check to his last known address and pay the extra money for proof of delivery.

    1. desdemona*

      I came here to say this – OP, by saying nothing, it may look like you agree with Sam.
      Keep telling Sam how you feel about what happened – and then also do what Michelle Smith suggests, and reach out to Doug to explain you had no idea, etc.

    2. Bagpuss*

      I think the apology part is great. The arrangements to get he money to him are presumably in part dependent on Sam – OP may not have access to the funds or be able to make those offers without Sam’s authority, unless she pay Dog out of her own pocket which she should not be doing.
      In that case, she could ask him his preference and say that she will pass that information along to Sam to arrange the payment / sign the check / whatever is needed

    3. Colette*

      I agree that apologizing is a good idea, but strongly disagree with getting more involved than that. This is Sam’s problem to handle.

  22. Ginger with a Soul*

    Sam behaved badly, full stop.

    The amateur psychologist in me, though (who has just reviewed the commenting rules to make sure this abides by them), wonders if in Sam’s head he was playing the role of White Knight in his response to Doug’s “long email explaining how offensive [OP’s] request was”. In other words, he may have viewed his response as, “Hey, leave her out of this! If you have a problem with me, you need to take it up with ME!” This could also explain why he has been resentful of OP’s telling him he was in the wrong; he may have expected a “My hero!” response.

    Since the commenting rules request such conjecture to be actionable, if OP thinks this might be the case, OP could directly ask Sam, “You responded pretty harshly to Doug; did you feel like you needed to stand up for me?” (And then, if receiving an affirmative response, OP would need to decide how to respond to what is essentially a patriarchal mindset: “I appreciate that you wanted to protect me, but I can handle a critical email” or some such)

    Of course, this is just conjecture and none of it excuses the behavior. Alison’s prescription (Sam should apologize to Doug and pay him) remains valid, regardless of Sam’s motivation.

    1. Brightwanderer*

      Oh, that makes a lot of sense to me. I definitely think it’s worth OP keeping in mind.

    2. Bernice Clifton*

      Or Doug might have thought the LW was asking on behalf of Sam, because Sam thought Doug would say no to him directly.

  23. Wildcat*

    This is entirely on Sam and he needs to make changes.

    1. Bouncing checks is very bad. The fact that Sam was also unaware he had outstanding pay obligations is also very bad. He needs new accounting systems/management. Sloppy accounting is never good.

    2. When you’ve messed up, you need to own it. Feuding with artists, especially when you haven’t paid them, is going to give you a bad reputation. What Sam should have done is immediately apologized. It also would not have been out of line to pay an additional fee for the delay/bounced checks. If Sam works with businesses, they will often automatically have penalties for this and artists should be no different.

    Sam needs to fix things, mostly because it’s the right thing to do but also because this stuff will absolutely harm his business.

    1. Be kind, rewind*

      Yes to your second point.

      OP, you want to help? Encourage Sam to pay Doug a not-insignificant proportion of his missed check ON TOP of what he’s owed, with a sincere apology and offer to repair the relationship. This is Sam’s responsibility to fix, and Sam has to make a good faith effort to admit their own fault in this situation and make amends.

  24. Mehitabel*

    Sam is 100% in the wrong here, and he owes Doug a big and extremely sincere apology for 1) bouncing the check, 2) not fixing the issue immediately, and 3) acting like the victim in all of this. If the LW wants to do something to fix this, the thing she can do is to tell Sam to get over himself and behave like an adult.

    Period.

  25. Ambie*

    Sam’s fault. I would definitely be upset about not being paid on time, then not being paid at all. If after that my boss put the responsibility on me to follow up, that’s a huge red flag and a total lack of accountability. As an employer Sam should have been mortified the check bounced and Doug wasn’t paid on time. Sam should have made sure himself this was resolved.

  26. I've Escaped Cubicle Land*

    1 bounced check means from now on you pay me in cash or certified funds. Period. Full stop. And if I incurred a bank fee due to the bounce check you’ll reimburse me for that too before I work for you again. I know artists/musicians are a whole different realm but still, getting paid accurately and timely is pretty basic.

    1. 867-5309*

      Given that they had the money immediately, I wondered if the error was on the side of Doug’s bank?

      1. Velociraptor Attack*

        If the check bounced, that wouldn’t have been an error with Doug’s bank.

      2. RagingADHD*

        If they had the money immediately, they could have done one of a million kinds of instant payments, or withdrawn cash to pay Doug. I have a feeling they are relying on paper checks precisely because they take longer to process, while Sam does some juggling behind the scenes.

  27. Karia*

    Has Sam considered hiring someone to handle the financial aspect? Even if it’s just someone on a contract basis, to ensure payroll and payment disputes. Emotion needs to be taken out of the equation here.

  28. Putting in my two cents*

    If you are trying to smooth things over and still get this guy to work with you in the future. First, get him the funds he is owed ASAP. Then you could offer to pay 1/4 or 1/2 the fee up front for the next event or next few events to restore the fiscal confidence (if that is within your power to do) and rebuild the business relationship. I agree that Sam should apologize, but it sounds like a spat between friends that was complicated by business. As this seems more like a relationship issue between the two of them I don’t necessarily think it’s out of line for you to speak with your partner about mending his fences with this guy. I think you could point out that Doug doesn’t want to feel like a debt collector whenever they hang out, but that the non payment could be stressing his finances which caused him to react the way he did. I don’t think you should apologize for him or act as the go between. Keep your role strictly about the business and business relationship if you can.

  29. MEH Squared*

    This is on Sam. It sounds as if Doug is at BEC levels with Sam, and I don’t blame him. You don’t mess with someone’s livelihood. Sam’s attempt to make himself into the victim is worrying (and distasteful). Doug should not have to repeatedly bring up he hasn’t been paid. He should, you know, just get paid.

    But this is not on you, OP. You should not be in the fray at all, and it’s worrisome that Sam wants to pull you into it. If you want to explain to Doug you had no idea in order to maintain the relationship, feel free. You would not be throwing Sam under the bus, though he may feel that way. Otherwise, you can step aside and let them work it out themselves.

  30. Observer*

    The main thing you need to realize is that there is no way to make Sam come out looking like a reasonable boss as the story stands. The two of them are NOT *equally* wrong. Sam is the primary person at fault here, and his acting as though someone demanding his pay is “walking all over him” says that he does not get his BASIC obligation as an employer.

    The ONLY way to do any level of damage control is to make sure that Doug gets pain TODAY. It won’t entirely solve the problem, but it’s the baseline you need. It’s also the only thing you have any standing or ability to address.

  31. Keymaster of Gozer (she/her)*

    Boil it down to the basic hard facts, like Alison did. You asked a guy to do some work for you, he pointed out he still hasn’t been paid for the previous work he did and thus isn’t inclined to work without payment.

    That’s entirely fair!

    The whole people getting angry and ‘how do I smooth this over’ bit is occupying a higher priority in your head than it should. As to what you can do, concretely, is get the guy PAID and if possible an apology from your partner for forgetting to pay them.

    Don’t ask if this’ll make everything better and if he’ll work with you again after though. When it comes to people not getting paid for work there can be a total breach of trust from that point on that’ll be very hard to reform.

    Suggest payment and an apology and then back away from the entire thing. There’s no point stressing yourself out over a mistake you didn’t make and can’t fix.

  32. 867-5309*

    While I agree Sam had zero standing to go off on Doug, I do wonder if OP told Sam that she had been unable to give check his check at rehearsal? Has Sam thought this entire time that Doug HAD been paid?

    My comment is in reference to this line in OP’s letter, “In fact, I remember Sam telling me the check had bounced and asking me to bring it in-person to give Doug at a rehearsal … but Doug called out sick that night so I couldn’t.”

    1. kiki*

      I do agree that this is relevant, but even if LW hadn’t communicated with Sam, Sam owned the task and should have checked in with LW or looked at their account balance to see if the check had been cashed. Things happen and maybe this was just a messy period of miscommunication, but I don’t like Sam trying to shift blame to LW and/or Doug. Ultimately, Sam is responsible for ensuring Doug is paid. If he took responsibility for the error, ensured Doug received his check (with interest?), and apologized, I bet the conflict would be largely resolved. But instead Sam is focusing on whether or not he should be blamed. Owning a business ultimately means the buck stops with you, and if Sam doesn’t like that, he isn’t ready to be a business owner.

      1. Be kind, rewind*

        Exactly. If this were the case (Sam thought OP paid Doug), the response from Sam to Doug should have been “sorry for the oversight, I’ll get that fixed” and not “not my problem.”

      2. 867-5309*

        Absolutely. I do not think Sam is in the right here – AT ALL – but just wondering if part of his anger is actually at OP for not telling him that Doug never got his check? Again, not excusing Sam, just looking for a bit more info.

  33. kiki*

    it mostly works out for everyone because we have our own areas of work

    One thing a lot of people don’t consider before they become romantically involved with somebody they work with is that other employees and clients may start to see you and your partner as a unit in business activities. Even though it doesn’t seem like LW’s job has much to do with payment responsibilities and monitoring that, Doug thinks LW would be aware that Sam has not paid him. That makes it a lot harder for LW to get her job done than it would be if she had no personal ties to Sam. It can suck to be held responsible for your partner’s work shortcomings that you knew nothing about and it can damage the relationship and the business. If I were in LW’s shoes, I would consider leaving to work somewhere my domestic partner’s work wouldn’t impact mine.

    1. RagingADHD*

      The other contractors are even more likely to see them as a unit if OP takes responsibility for Sam’s mistakes and Sam’s communication issues. The more smoothing and fixing OP does, the more they are seen as a unit — because that’s how they’re acting.

  34. Spicy Tuna*

    My domestic partner of 18 years and I own a business venture together. We started it after we got together. I do not like how he conducts business AT ALL. He does not like how I conduct business AT ALL. The reality is that both of us have flaws / faults in how we communicate with and treat vendors and clients. The “correct” way is probably somewhere in between both of our styles.

    When you combine business with your relationship, things can get messy! I have found that the way to work most effectively together is to NOT take anything related to our business personally. If I screw up, I own it. If I disagree with a decision he makes, I do not make my reaction to it personal.

    All that said, I do think the OP did drop the ball a bit on Doug’s payment. Like other posters have said, contractors / employees can let a lot of things go, but not when it comes to money!

  35. ecnaseener*

    Just to hammer this point home, LW……it is super duper not your job to prevent Sam from sending rude emails. If you had *actual information* that might have de-escalated the situation (such as “oh gosh Doug that’s actually my fault, I forgot to tell Sam I hadn’t given you the check” [still Sam’s job to ask LW, but whatever]) then that would be one thing, but it sounds like you just feel guilty that you didn’t get a chance to save Sam from himself?? He is just as capable of sending a polite, professional response as you are, he CHOSE not to.

    1. Bernice Clifton*

      This is exactly what I was coming to say. It took me a looooong time to realize that just because I was involved in a situation where Person A pissed off Person B doesn’t mean that I need to assume guilt when I did nothing wrong.

    2. kiki*

      This! Sam is the business owner! He can definitely send polite emails all on his own if he felt so inclined. I have no doubt the LW would have handled it better if she would have responded to the email first, but that isn’t actually LW’s fault or responsibility.
      I’ve noticed this thing that happens a lot in business where a man with a lot of ideas is in charge but only because other people (often women) are coddling him, protecting him from his own actions, and actually executing on ideas and nitty-gritty details like ensuring everyone is paid. If I were LW, I would check in with myself and observe Sam: have you been intervening so much on his behalf that he doesn’t really know how to do his job on his own? Would it benefit both of you if you took a step back from supporting him so he can learn on his own, even if it causes issues with Sam’s business?
      I’ve noticed this a lot in my field which is male-dominated (software development). I’ve had to learn to interact politely and graciously with people because I am a woman of color and life wouldn’t let me not learn that. A lot of dudes make it all the way to leadership roles without learning how to kindly get what you need. Often because they lean on people like me to do that part of *their job* for them. I’m trying to learn how to stop filling in for them and make leadership consider that, hey, maybe actually *I * should have that dude’s job if he can’t do major parts of the role that I’m doing for him.

  36. wordle clone of the day*

    So, like, a bounced check is the giver’s fault.

    Does Sam have the money to pay Doug?

    I have many concerns here.

  37. knitcrazybooknut*

    Hey OP, this is tough. But even if Sam won’t apologize to Doug because he wants to save face, he may want to apologize in order to save his business. You could point out the business repercussions that this defensiveness will cause, and talk about the professional behavior that’s necessary even when you are upset in the normal business world.

  38. Sunny*

    OP – I think Alison’s suggestion to look at distancing yourself professionally from Sam is a good one. Presumably your relationship is more important than continuing to work at this business, right? I would maybe give him time to cool down from this instance and then try to find someone to cover your responsibilities.

    Alison – Not relevant to the letter but there may be a coding issue with the website. I have noticed on both mobile and desktop when I collapse comments, they will reopen again as I scroll down the page (but the little arrow below the main comment still shows them as collapsed). Not sure if others are having this issue but thought I’d mention it!

    1. RagingADHD*

      The collapse – springback thing started happening after the latest update to the advertising system.

    2. Dr. Rebecca*

      THIS HAPPENS TO ME TOO, ALL THE TIME! I’ve reported it as a tech issue several times, but it’s still doing it.

  39. anonymous73*

    As an employee, it’s not my job to remind my employer to pay me. Period. And there seems to be a history of something between Sam and Doug because it escalated so fast. This is not your issue to fix. If either of them asks you to get involved, let them know that you won’t be getting in the middle of it.

  40. Sylvia*

    In my organization, a lot of employees are underpaid and a late paycheck–even by just one week–would result in their electricity being shut off and feeding their families from the local food pantry (some of them have to do that already, even with a paycheck). So when someone comes to me for help because they didn’t get paid, I drop everything and make their money my first priority. I feel like it’s a good practice no matter how much an employee makes.

    Going forward, I would make paying contractors/employees a priority, even if they are personal friends. If a paycheck bounces, then the owner/manager needs to get in their car and drive a new check over to the employee’s house ASAP. If that’s not possible, then let the employee know exactly when they can expect that check and how it will be delivered, communicating every step of the way. It might help the situation with Doug if Sam were to 1) apologize, and 2) acknowledge that the situation shed light on the problems with the current payment policies, and make changes to it because he values the contractors and their work.

  41. Falling Diphthong*

    OP, a few years ago a large company for whom I often work bounced checks to me and several other freelancers–someone drew them on the wrong account. When my boss figured it out he immediately alerted everyone affected and issued replacement checks for the original amount plus any bank fees do to the bounced check. This was about $7 in my case.

    Just before tax time the following year, I figured out that my totals and theirs were off by this $7–they’d classed that as income rather than a reimbursed expense. It was a small amount, it was almost 4/15, I didn’t make a fuss and paid the taxes on the $7.

    But I am still salty about it.

    “Sometimes you pay people and the check bounces, life happens” is so much NOT what anyone to whom you owe money wants to hear.

  42. KatieP*

    In addition to Allison’s response, this would be a big red flag for me. It may be because I work in a financial area – bouncing checks and disregard for the finances of another individual (or the failure to uphold his end of the agreement) would make me very concerned about the future of my relationship with Sam.

  43. JS*

    Doug received a bounced check, went weeks of not getting paid, got yelled at after putting up reasonable boundaries, and never got an apology. Those are huge red flags for working with Sam. Red flag, red flag, red flag! Doug can’t be blamed if he warns others. Those are the consequences of burning business and personal relationships.

  44. RagingADHD*

    What “side” of the story do you think Sam or you could tell to the community that would mitigate what happened here? You and Sam seem to have gotten all consumed with the emotional sturm and drang here, and you’re ignoring what actually happened.

    1) Doug’s check bounced! This is not okay. This is never okay. Your company has major problems with its business practices.

    2) Then Doug never got his replacement check. Also never okay. You don’t f*** with people’s money. It doesn’t matter if he called Sam everything but a child of God. You pay people what you owe.

    3) Then you asked him for a favor, because there is apparently no internal communication between you and the owner/your partner. Again, terrible, shoddy business practices.

    4) When Doug said he wasn’t doing any more favors because he hadn’t been paid, Sam threw a tantrum about how it was supposedly Doug’s fault? Now the company is moving from bad business practices to terrible personal practices.

    All Doug has to do is tell the truth, and any artist with an ounce of common sense (or any other options) will be extremely leery of working with you — rightfully so. Clients who care about working with a well-run operation will be leery of you, too. The only way for you to present some other “side” of the story would be to lie through your teeth.

    I’ve worked in the arts, and seen plenty of companies go from promising and relatively stable, to chaotic and unreliable, and from there right down the toilet. The quality of talent they can attract goes down, which then impacts the quality of jobs they can book. If you have any kind of ownership stake in the company, you need to get Doug his check ASAP along with a profuse apology, and get some better systems in place to ensure this doesn’t happen again.

    If you don’t have an ownership stake? Leave Sam to deal with his own responsibility in his own way, and go find yourself another source of part-time income. You will need it very soon.

    (On a side note, since you say Sam is your partner, maybe take a look at how he reacts when people give him legitimate criticism or boundaries. You should take that seriously under advisement and proceed accordingly. Do you often have to lie or cover for his mistakes? Do you make a lot of excuses for the way he treats people? Do you make excuses for the way he treats you? )

  45. Hell in a Handbasket*

    OP, it seems like you care about Sam’s business more than he does. You’re worried about the impact of Doug’s absence and the business’s reputation in the community — but if Sam, the owner, doesn’t care enough about those things to get over himself and apologize…then it’s certainly not up to you to fix any of it.

    1. TiredMama*

      I disagree some. Her relationships with other artists and professional reputation are tied up in this.

  46. eisa*

    Nothing to add regarding the letter itself, but I found the headline misleading : “I work part-time for a small company owned by my domestic partner, Sam. We were together before he started the company about 10 years ago” , that’s basically a family-run business. “I’m dating my boss” implies something quite different.

  47. Nonny Mouse*

    “You are blaming yourself for something you didn’t cause, and trying to take responsibility for fixing something that isn’t yours to fix.”

    I want that cross-stitched on a pine-needle sachet.

  48. TiredMama*

    I suspect you know this, OP, but Sam is the one in the wrong and he is the only one who can “fix” things. You can try to salvage your friendship and professional relationship with Doug, but that is it. I also suggest that you consider your role in the business. It sounds like you are sort of half in and half out of administration, and I can see why that is easy to do, but it does not appear to be working (the check, the schedule change, etc.)

  50. Koala dreams*

    1. If you and your partner owned the business together, I would say you needed to sit down, straight out the finances and come up with a better system to pay people on time. Depending on your involvement in the business, you might still want to do that. Different families treat business matters differently, so it’s impossible for an outsider to say. (As you are a contractor I’m assuming you aren’t in a role where it would be your actual job, although perhaps I’m wrong.)

    2. Not paying on time, especially not paying people who work for you on time, is a warning sign for financial instability. Also, it’s not necessarily a big difference between not having money to pay people or being too disorganized to pay people when your business depends on your good reputation.

    3. More to your situation, it can be especially difficult to depend financially on a family business you don’t own. It’s natural that you care a lot about the family business, but you also need to care a lot about your own, private finances. What can you do to protect your own finances?

    4. Although I agree that you should always pay what you owe, I don’t think the situation is unusual. A lot of people wait for the bill to pay, and if they don’t get the bill and don’t get a reminder they simply don’t pay. From the other side, to refuse to do more work until you get paid is a common response to clients who pay late. Similarly, a vendor might refuse to ship more orders until the previous orders are paid in full. It’s standard business practice.

  51. A Feast of Fools*

    Oof. Sam sounds like my ex, with whom I co-own a small business.

    He gets offended and takes things our employees do personally. I am ALWAYS saying to him, “There are no feelings in business.” As in, this is a business transaction, not a personal relationship. We aren’t a family, our employees aren’t our children or our friends.

    He has been offended when an employee shows up late. I’ve had to say, “The employee didn’t show up late because he disrespects you, he’s late because something happened. And, hell, even if it was a power play on the employee’s part, it’s a pretty dumb one and why on earth would you waste a single second being offended over something dumb?”

    Because I’m a co-owner and not a part-timer, I at least have the authority (and the direct financial interest!) to act as our HR department and coach my ex on how to behave professionally, intervene on the employees’ behalf, and let them know that if they have an issue and feel like they’ve met a dead end [or, really, a black hole] with Ex, they can text/call/email me.

    If the OP’s situation happened in my business, I would flat-out tell Ex that he was in the wrong, that we have a legal liability to pay people for their work, so the onus is on us to make sure they get their checks. Their *good* checks. Ones that won’t bounce. And that his feelings don’t mean sh*t if no one will work with us. “Do you want to act on your feelings or do you want to have a profitable business?”

  52. Evvie*

    Woof, I almost wonder if this isn’t a theatre I used to work at. A check bouncing would have been a good day for them, and people literally auditioned for them to simply see if the rumors are true (and would turn down gigs if offered–my area doesn’t exactly have a thriving arts scene, either).

    They got publicly me too-ed (and worse) pretty hard a couple years ago and are still open. Of course.

    If you can’t pay, you don’t hire. But this is not at all on the writer and strictly on the person who runs the theatre.

    I know the OP isn’t asking for advice, but I this is a protect your butt: Keep these emails. Especially if ANYONE who works there is union. You don’t want to look like you’re hiding anything. On the off chance this happens again, I’d chime in with “this is the first I’m hearing of this issue and since it’s outside my job responsibilities, I am exiting this conversation.” You lose plausible deniability over having seen the emails, of course, but at least you have in writing that you didn’t know AND it’s not your job to know.

  53. Spritesoda93*

    I just wonder if OP was told to give the cheque to the performer in a professional sense as they are the one who deals with the finances or a personal favour to the one that they are dating.

    If it’s their job they need to do better about doing it and if it was only personal there needs to be a better system for paying people

  54. Boof*

    One slight quibble with the advice; i believe feelings are what they are, and aren’t specifically “wrong” or “right”. (The logic may be wrong, the facts or assumptions driving a feeling may be incorrect, the feeling may be disproportionate, unjustified, or problematic; but they exist and generally won’t immediately go away even if the person having them tries to dismiss them). One can’t really argue with feelings.
    Instead perhaps emphasize that Sam can feel whatever he needs to feel but the professional thing to do is pay people on time, and make any mistake or delay in pay a top priority to fix; so to be a good boss he needs to put his personal feelings aside while dealing with employees in general – and n this particular case it would mean apologizing to doug for the delay. Lw, if you are his second in command it would be ok to offer to do it for sam but sam HAS to agree and be on board with it

    1. RagingADHD*

      Feelings come from thoughts and perceptions. You feel what you feel, but the root attitude/thoughts (such as entitlement, selfishness, etc) can most certainly be incorrect or even morally wrong.

      If Sam has convinced himself that Doug is the one at fault here, he is very much mistaken. If he thinks Doug owes him an apology for wanting to get paid, he is way out of bounds.

      1. Boof*

        Lw also clarified that by bounced check they meant it “ bounced back to us because Doug moved and didn’t update his address with us.” So I think it’s a little more understandable that the onus starts being more on doug to give them a way to get paid

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