am I too generous with my employees?

A reader writes:

I care about my employees. A lot. I pay people significantly higher than average salaries. They get treated to generous benefits, bonuses, random gifts, and I’ve even paid for employees’ honeymoons. Several times throughout the years when someone had a personal emergency, I gave them money – sometimes thousands of dollars. I do it because I grew up near the poverty line and saw my parents endure horrible, manipulative employers. I feel like I have a moral responsibility to look after the people who work with me.

I’ve established a strong personal friendship with many employees. A lot of other times, though, people don’t seem to care. The most recent example is an employee whose daughter had a medical condition. I gave him extra paid sick leave, reduced his hours to part time but continued to pay full time wages, and paid for all expenses not covered by insurance. At the time he was moved and grateful. Then as soon as his daughter recovered, he resigned without notice. As he quit during the busiest season of the year, I pleaded with him to work his notice period at least. He declined, saying he would miss out on cheap fares to go overseas. He then later went to work for a competitor, even though that’s against his employment contract.

I don’t expect somebody to work for me forever because I gave them extra money. But this hurts on a personal level because I’ve treated my employees far better than the average employer. I know every business owner experiences staff problems. Would it be less of a pain in the neck if I simply stopped being kind to my staff and have no expectations? I’ve been told I’m overly generous and I should be more calculating. I wonder if that advice is correct.

That’s really tough. You sound like an incredibly kind employer. I think, though, that you’re expecting certain things in return for your kindness that might not be reasonable to expect.

Here’s the thing about being generous with your employees like this: It will make many people much more loyal to you and invested in doing a good job — but not all. It will help you retain some people and generate significant goodwill with them — but not all. You’ve got to be comfortable with the idea that not everyone will respond the way you’re hoping they will; humans vary widely in their reactions, and everyone brings their own baggage and assumptions to interactions with their employers. But if most of your employees seem to appreciate your efforts, focus there.

That said, if you’re seeing widespread evidence that people don’t care about the generosity you’re showing them, it does make sense to pull back on some of it. Just make sure that it’s truly widespread, not just the responses of a few. Sometimes a bad reaction from a few employees can sting so much that you start to feel like it’s more widespread than it really is.

Aside from that, though, it’ll be better for you and your employees in the long run if you remember that these are still employment relationships, not personal ones. Your employees need to be able to put their own interests first, which might mean leaving at an inopportune time or right after you did something especially generous for them. You don’t want people staying out of a sense of guilt, or turning down a truly great opportunity out of obligation. (To be clear, it’s not OK for someone to leave with no notice or violate an employment contract — but I’m assuming that most of the time when you feel unappreciated, it’s not so extreme.)

Read an update to this letter here.

{ 213 comments… read them below }

  1. MariaTeapot*

    Well said, Alison. I think it’s important to make sure the gifts that they’re giving are structured and fair too. Nicely said.

  2. Hello...ello...ello..ello..llo..llo..lo*

    I have to be a little honest here… while on the surface all of this sounds great I’m a little worried that you are expecting an emotional return from your employees that is either inappropriate or unrealistic.

    In other words, be generous and fair if that’s what you want to do, but don’t expect anything in return. Otherwise you’ve turned the generosity into a transaction and obligation.

    1. Snark*

      This is kind of where I’m at. On the one hand, it’s so refreshing to read about an employer who’s being generous and not entirely mercenary with their employees. That’s great. Don’t feel like you shouldn’t. On the other, I feel like random gifts and honeymoons should be regarded as gifts and tokens of appreciation, not a quid pro quo. If you feel that you can’t do that stuff for employees without considering itan obligation for which they need to reciprocate, I think you should rein it back. The employee who quit was pretty unprofessional and I think LW had certainly earned and merited him working out a generous notice period, but the employment relationship is fundamentally and rightly transactional and either party can decline to continue it if it’s not working out.

      My parents owned a business for many years, and I watched them cultivate warm and mutually rewarding relationships with employees and partners. They did a great job of looking after people and giving a fair and reasonable deal. But it was, at heart, a professional business relationship, not a family or a group of friends.

      1. Justme, The OG*

        Agree. I know that the company Boxed pays for employee weddings and college for the kids of employees. And sure, it goes a long way towards employees feeling like they matter to the company and CEO. But noting should be expected in return other than that employee doing their job.

      2. Jen S. 2.0*

        +2. Being a great and generous employer doesn’t mean people have to stay forever or put the company before themselves and their families and their needs. Be a great and generous employer because it’s the right thing to do, not because you think it will create obligation to be anything other than a great employee. If there’s anything you’re doing that you think should be creating an obligation beyond “be a great employee,” or that has strings attached, pull it way back. These are your employees, not your friends or family.

    2. zora*

      Yeah, I like what you are saying. Is it Miss Manners who says that giving a gift should be free of strings? Usually in reference to thank you notes, but I think the concept works here.

      If you are giving so much to your employees that you are really hurt and upset when they don’t respond the way you want them too, maybe you are giving a little too much? Can you think a little more about why you are giving these things? If it’s really a gift, your reward should be in the giving. If you are expecting something specific in return, it’s not really about the gift, it’s about your feelings.

      I don’t say this to be harsh at all! I just think it’s worth thinking about your own feelings a little bit and where they are coming from. And as Alison said, if the majority of your employees are appreciative and loyal, then focus on them, and the good feelings! And try to let the frustrated feelings roll off your back.

      And my last thought, is there a middle ground? If you just cut back a little bit, would it feel less hurtful if someone didn’t appreciate your generosity? Like, giving the work related support (salaries, PTO, etc) but not giving so much additional cash (honeymoons, etc) and keeping that money for something that does make you feel good. Giving it to a charity, or spending it on your family, or using the money to buy things for the office that current employees get to enjoy?

      Just some thoughts. You sound like a lovely person, and I wish you all the best!

      1. Liz*

        I don’t see it as an unexpected string to expect an employee to work out his notice period, especially during the busiest season.

        It seems even more reasonable to expect at least the minimum notice, not leave you in the lurch, when you paid his medical expenses and gave him lots of paid time off but that’s me considering basic politeness.

        1. Luna*

          You are right about the notice period (and the fact that he went to a competitor in violation of his contract), but the expectation should be based on professional norms and the employee’s contract, not on the fact that the OP chose to give him extra personal perks.

          1. JB (not in Houston)*

            Yes. This is a business, these are professional relationships. If paying hospital bills makes the OP expect more than professional norms require, the OP shouldn’t do it.

          2. zora*

            Exactly what Luna said. The notice period should be because of the job, not because of the extra support the boss gave.

    3. HRish Dude*

      Weirdly, I was reminded me a lot of the “nice guys” who buy women gifts and do them favors and then expect that all of this “generosity” will somehow result in a relationship. I recognize this is a giant leap from what is in the letter, but it seems to come from at least the same family of concepts.

      1. Middle School Teacher*

        Agreed. On the surface it’s super nice, but on another level it’s a little… scary.

        (However, full disclosure: I was in a relationship like that so I’m admittedly a little sensitive to this kind of thing. It’s possible I’m reading more into it than what’s there.)

        1. headache on a plane*

          I think it might be more complicated than it appears, but I would say scary seems a bit far. Sorry to hear you had a rough time previously.

          1. Middle School Teacher*

            I honestly couldn’t think of another word. Creepy? Weird? I don’t know. (Plus I was trying to not offend the OP. I don’t think they’re creepy or weird or scary, but having been in that situation from the other side, it is all of those things.)

            1. Emily Spinach*

              I think at least overly-involved. It’s generous and I’m sure greatly appreciated by most if not all staff, but I don’t know, paying for employee honeymoons is really personally involved!

      2. The OG Anonsie*

        Hah! You know, all the toxic workplaces I’ve been in had that exact attitude and I’ve never noticed the parallel. “We gave you this job, it’s an opportunity for you that we have so generously given, and unless you work yourself to the bone and never ask for anything else in return then you’re being ungrateful and trying to take advantage of us!”

        1. Natalie*

          And the attitude doesn’t even have to be present in the owner. I could see this kind of excessive gift giving having that affect on the employees’ thinking even if the owner has totally altruistic motives.

        2. Mediamaven*

          Yes, but on the flip side, if your boss wasn’t generous that would be an issue too. I agree with all the feedback in this situation but I’m also sympathetic to this boss because she truly is trying to be the best boss that she can and going above and beyond. I hardly think piling on her makes sense.

          1. The OG Anonsie*

            Oh yeah, the toxic workplaces I’m describing there would have never given an extra inch on anything no matter how great your need was. I’m saying that weird Nice Guy attitude is actually really present in a lot of workplaces and I never thought of it that way!

      3. Daisy*

        I thought that too, there’s some really off logic here. ‘I’m so nice and generous, but one person didn’t give me what I wanted in return, shall I stop being nice and be calculating?’ Well… in that case you were always being ‘calculating’.

        1. Ego Chamber*

          Hard disagree. It’s not necessarily calculating to feel taken advantage of when you’re generous with people and then someone can’t even manage the bare minimum of social niceties (and in this case also broke a contractual obligation) in return.

          LW would be justified in being upset about this even if s/he hadn’t gifted the employee anything, so it’s not that strange that the gifts are adding a little more salt to the upset.

      4. Ego Chamber*

        “Weirdly, I was reminded me a lot of the “nice guys” who buy women gifts and do them favors and then expect that all of this “generosity” will somehow result in a relationship.”

        I agree with the “weirdly” part because this analogy doesn’t work for me at all. LW is complaining that an employee left without giving notice and then broke the contract he had with LW’s company by going to a competitor.

        If you insist on a relationship analogy, that’s less like being upset that a woman didn’t put out after you bought her a couple drinks and more like being upset that you went out on a date with someone who left without saying anything halfway through dinner when you were being a perfect gentleman (and I mean gentleman, not a “nice guy”).

      5. Elsajeni*

        Yeah, I don’t think it’s exactly the same, but I do notice that the OP says she’s developed a “personal friendship” with some employees, apparently based partly on being a generous manager. I think part of what’s happening here is that she’s blurring the boundaries between work relationships and personal friendships, and maybe expecting that being generous — EXTREMELY generous — with pay and time off will earn her a level of personal friendship and loyalty that isn’t really reasonable to expect from your employees. (Not specifically in the case of the guy who left with no notice and then violated his non-compete — that guy is violating workplace norms, too, not just personal-friendship norms — but more generally, since she says that’s just the most recent example.)

    4. Manders*

      This is a great point. I’d also add that while gifts usually make people feel good, if the gift-giving is based on random tragedies or life events, some people will find that unfair and they’ll leave for a place with a more logical bonus structure. It also invites comparison if the gifts aren’t exactly even each time–if Miriam got her whole two-week honeymoon to Japan paid for and Joe only got $1,000 in cash, even though you were still generous with Joe, he’s going to feel slighted.

      1. Where's the Le-Toose?*

        Agreed! And the randomness also leads to the unintentional lawsuit, at least here in the U.S.. Miriam happens to be a 32 year old Catholic Caucasian woman. Joe is a 55 year old Latino Muslim. Joe not only feels slighted, he thinks it’s because of his age, or his race, or his religion, when that was never the OP’s intent.

        I would ask the OP how these “gifts” are funded? If the honeymoon, etc., was paid as a business expense, then taxes should have been taken out and giving an employee a bonus based on criteria other than performance at work is going to be difficult for a lot of employees to tolerate. If the OP personally paid these amounts, then as others have mentioned, there are a lot of other worthy causes to donate money to. Getting a lavish personal gift from my boss would make me really uncomfortable. Honestly, if I got cash, I would probably take it, but if it was a $3,000 watch, I’d return it. Because the next question always would be “hey, how come you never wear that watch I gave you?”

    5. MLB*

      Agreed. While she believes she’s being generous, she’s actually crossing a line IMO. Paying for employee honeymoons? As an employee I wouldn’t feel comfortable accepting something like that from my employer. She should stick to being flexible as needed for employees schedules, but she needs to stop with the gifts and money. And I say this as someone who’s manager is a true friend (not just someone I’m friendly with).

      1. BPT*

        Agreed – it’s great to be a generous workplace, but personal gifts (and the expectations that come along with those) seem to be a little more inappropriate to me.

        Being flexible with vacation time? Giving additional time off during sickness or emergency? Paying above average wages? Giving good bonuses? Paying medical expenses? All great things.

        But paying for people’s honeymoons would make me feel a little uncomfortable on the receiving end. If it’s from work, I’d be wondering – they’re paying for this vacation. Is it appropriate for me to get a massage? Order a really expensive meal? If you’re just paying it by way of a bonus, that still seems unfair to me to other employees who don’t go through these milestones. I worked for a place where my (already very highly paid) bosses got raises when they got married, bought a house, and got divorced. But when I was there picking up the slack from them being out because of these things (and generally picking up their slack in general), I got no raises. Pay should not be based on your life circumstances but on your actual work.

        I would say set up a yearly bonus system that you give out based on merit. You’re still being generous, people feel like they’re actually earning the money, and they can use it for whatever they want.

        1. beanie beans*

          Exactly all of this! Treat your employees well *as employees* not as friends or family. The honeymoons and I’d say even the medical expenses go a little too far.

          Generosity with vacation, sick leave bonuses, and things directly related to work (fair workloads, flexible hours, reasonable expectations, good management, etc.) are much more important to me in an employer.

        2. Boots*

          It does suck as a single and/or child-free person to see a company bend over backwards for only some life circumstances. My husband’s job did things like: let employees who were parents leave early for games or plays, “accidentally” not count a sick day when their kids had the flu, etc. Meanwhile, my husband was caring for a sick parent, and got nickel-and-dimed every time he had to leave twenty minutes early to take her to a neurology appointment.

          He and I have talked several times about how companies who sell themselves on being “family friendly” really only mean “child friendly” because we both have always gotten hassled for having to handle elder care.

          1. Quickbeam*

            This. Story of my life. I’ve covered hundreds of maternity leaves in my 40+ year career, not one thanks you or a nickel more. Double the work. At my current employer, parents have flex time, work from home benefits, very easy going start and stop times. Not the rest of us.

            1. Beaded Librarian*

              I had an ex whose employer was great about him taking all the time off he needed to help with his cancer stricken mom, but when he had a seizure and broke the back of his shoulder? They were hassling him for how soon he could come back, which based on long term problems he ended up with on that arm I’m pretty sure was too soon.

      2. Plague of frogs*

        I came here to say the same thing. I would only be comfortable accepting money from my employer that is part of my compensation. A sizeable personal gift would make me really uncomfortable.

    6. Nanani*


      Keep it professional. They are not your friends, they are employees. They are not your family, they are employees.

      There is still a power dynamic in your favour.

    7. The OG Anonsie*

      I wholeheartedly agree with this. Providing good salaries, benefits, and flexibility to your employees will bring in and let you keep good people. It encourages productivity, makes people happier, and makes them the much more likely to be cooperative and helpful to you when they can be. You should do it for these reasons.

      You should not expect to get a close personal, emotional response as your return on this investment.

      In fact, I think framing it as generosity is part of the problem– thinking of it as your personal generosity does imply that the correct response is a personal/emotional one. What it is really is part of the compensation you provide to employees, which is an investment that gets you a good workforce in return. It’s a business decision for which you will get a business return.

      1. Jesca*

        I like what you say here.

        But I will add that not all compensations offered by the employer come with “no strings attached”. For instance, almost every company I have worked for that offers tuition reimbursement has tons of strings attached. Usually these strings consist of a commitment to working for the company for at least 2 years after the last class was paid for by the company. Otherwise, you have to pay the company back. So, OP, I would not drop your compensation intensives, but I would take The OG’s advice and definitely remove yourself more emotionally from it. I would also recommend putting some things with definite stipulations (as in, make a handbook with some clear guidelines in receiving those extra benefits) as other backlash may occur like being accused of favoritism if some employees think you treated Wakeem better than Jane while in similar circumstances.

        1. Jen S. 2.0*

          To me, the difference is that you know the conditions going into having a company pay for your degree, and you have the realistic option to decline. You could pay for your degree yourself if it’s THAT critical that you not stay with the company for 3 years afterward, or whatever. In the case of the sick leave here, the employee can hardly say, “Oh, no, my daughter is very sick and the medical bills are piling up like gangbusters, but I’ll just quit my job instead of taking these extra two weeks that you’re offering.”

          That goes double because the expectations only became clear after the fact, when the employee tried to resign. The employee had no idea what the strings were when he accepted an offer made in an emergency moment. Yes, the employee should have handled his resignation better, but the extra sick leave wasn’t the catalyst for that.

          1. Ego Chamber*

            “That goes double because the expectations only became clear after the fact, when the employee tried to resign.”

            Not really. Expecting a typical notice period and expecting employees to not break contracts are pretty much bog-standard, even at jobs that don’t go overboard handing out extra money and time off, so it’s not really fair to refer to standard expectations as “strings.”

            I think LW is taking the employee’s unprofessional behavior harder because of the gifts s/he gave to staff (and that reaction is a good reason to reassess that behavior), but I don’t think it’s unreasonable for LW to be upset about an employee who was unprofessional and broke their employment contract.

            1. Safetykats*

              I’d like to point out, because there has been a lot of discussion about what is a “standard” notice period, that in most of the US (if that’s is where this company is located) the legal standard is at-will employment. You do not owe your employer any notice, and they can also remove you from your job with no notice. Yes, people generally provide two weeks, but that’s a courtesy, not an obligation.

          2. The OG Anonsie*

            I agree, there is a pretty big distinction in my mind between accommodating employee’s needs and giving them additional perks or bonuses. That distinction isn’t as solid for a lot of people, though, where the fact that most workplaces are extremely unaccommodating makes them feel like providing that reasonable level of flexibility is a nice perk. And whoo boy, getting a holiday party is not the same as being able to get a flexible schedule around an illness.

        2. The OG Anonsie*

          Right. It’s not that there are no strings, it’s that the strings are business related and not personal.

      2. Mints*

        Yeah, I think the goal should be “be the best boss ever” not “meeting all of my best friends at work”

    8. ContentWrangler*

      I agree. While the OP is obviously incredibly generous money-wise with their employees, I was very concerned by the end of their letter where they ask if it would be easier to just “stop being kind” to their employees. I’m sure many of their employees have appreciated the financial gifts, but that is not the only way to be kind to employees. Be a good boss, be fair, offer guidance and mentorship, support advancement – there are so many ways to be kind to your employees that don’t involve personal money. Maybe if OP focuses on building employer-employee relationships that way, they’ll feel less betrayed when someone does a normal thing like leave their current job (though of course in this instance, the specific person was inconsiderate to leave without notice and possibly illegally breaking their contract)

  3. CBH*

    OP Alison said it best.

    On a side note, I would also like to point out that you go above and beyond for your employees. That’s a great thing. Technically you should not expect things in exchange but I would also think your employees would realize (hopefully) what a good deal they have with you. I personally think some employees will be under the impression that all companies are like this and will be shocked to find out that most aren’t. While one can be cordial I would think they indirectly burned a bridge. They owe you nothing, but should appreciate it and shouldn’t be shocked when reality hits about the green grass on the other side of the fence.

    1. Chatterby*

      Agreed. If they were new to work world when they were hired, they likely think this is just how things are, or that the normal company they worked at before this one was ‘bad’.
      If it’s a truly great place to work, the LW will see above-average retention rates, and a more frequent than normal rate of former employees trying to be rehired.

      1. CBH*

        Chatterby thanks for responding to my post. I keep flip flopping on this issue – see below – but I think you summed up what I was trying to say perfectly

      2. designbot*

        That’s a good way to look at it–on average, does it net you the intended effect? On average, are your employees more dedicated, longer lasting, etc? Likely there’s both extremes here, the seemingly ungrateful and the incredibly attached people who intend to work for you for life. Neither should be taken as representative of the whole.

    2. CBH*

      OP reading some of these comments makes me rethink my statement.

      I think you are being a little too generous, too invested, but your heart is in the right place.

      If someone chooses to accept (as in you are not forcing a financial gift onto them), then I think you need to not expect something in return. It would be nice for a recipient to show appreciation – such as in your example not quitting during a busy time, but it is not required.

      If financial assistance is a known company benefit that someone can rely on, a safety net, something to expect as compensation, and someone comes demanding help then I stand somewhat by what I said before that your assistance is generous and employees may not realize that it is not common at most companies.

      I found this post conflicting. OP’s heart is in the right place and he may even be using this to form some sort of loyalty or friendship, but it’s a bit much and puts people in awkward scenarios. I’m sure I’ll want to adjust my opinion after reading more comments…. I keep picking up on things that change my opinion!

      1. The Cosmic Avenger*

        This thread has helped me figure out what was bothering me.

        Rescuing people single-handedly is something usually done by family, or in unusual instances, dear/best/lifelong friends. As an employer it’s more appropriate to provide pay and benefits so that employees are capable of taking care of these things themselves. And even then, whether they’re employees or family, even when given the resources some of them will not prepare for the worst, and will be in trouble if they have one large misfortune or a series of smaller ones. Those who had the opportunity and didn’t prepare need to learn the hard way how to be a boring, responsible adult and buy insurance, and have an emergency fund, etcetera.

        I know not everyone can do that, but if your employer is very generous you probably have a better chance than most of being prepared. We generally live a very middle-class life so that we can retire early, and because of that we’ve recently reached the point where we can actually splurge a bit and still be extremely prepared for financial disaster.

        I don’t want to discourage the OP from being compassionate and generous, but I think it might be kinder to their employees if they were more systematic and less personal about it. If the generosity is predictable, it is easier for employees to plan their lives accordingly, while not making this such a personal issue for the OP.

        OP, you might want to consider directing that generosity towards charities that help people in crisis, and then any employees who are overwhelmed can be helped by those organizations, but regardless of how your employees fare, you’ll be helping those in need. I know my charitable donations are directed partly by my interests and deepest sympathies, there’s nothing wrong with that.

        1. Yet Even Another Alison*

          I think what you wrote Cosmic was what was mulling around in my head but you said it so well. For example, letter writer, channel your extra money into getting a really top notch healthcare insurance provider (if you don’t already) and pay 100% for the premiums for employees and their families. Load up their HSA accounts with contributions toward deductibles. Pay the premiums on life insurance for 7 X the employees’ salary. Pay the premium for AFLEC like insurance for each employee so if the crap really hits the fan with their health, they don’t have to pay out of pocket for household services and the like while they are healing. Place 15% of the employees earnings into their 401K vested immediately. Or give them a chunk of cash, and many options, that will enable them to customize their benefit package to their needs. I think this is the cafeteria style. This will help employees help themselves, not be so personal, but demonstrate, at least to someone like me who has experienced and seen the best and worst (and even the best was not as good as described above in terms of remuneration) that you want to be considered a top notch employer. Within the realm of employers – you likely will be tops.

          1. CBH*

            Yet Even Another Alison you nailed it. I couldn’t think of a solution but you nailed it.

            First I have no issue with a company stepping in to help with something that even the most prepared can’t be prepared for. I keep thinking of the AAM posts about helping the coworker whose infant child was in NICU or the OP who needed a service dog (but ended up not needing it!). I agree with a community/ company helping out. I think the OP for this letter has their heart in the right place but is looking at this as a) helping out emotionally, but b) as a way to buy loyalty. I think in doing so the results have been polar opposites – those who appreciate it and those who think it is an automatic benefit and right. That leads into my original post discussion about employees thinking all companies are like this and would be shocked to learn they aren’t. It’s great that the company / OP does care so much about the employees.

            But I think you point of getting top noch benefits in healthcare, 401K etc would give everyone the best of both worlds. You would gain loyalty with such amazing benefits. If someone wants to leave it’s their new task to find a company with benefits to match – that will be hard! This would also give OP the chance to “donate” in such a way that would be fair to everyone and free up the financial burden employees would experience for most of these instances.

          2. Mints*

            This is why I only briefly watched “Undercover Boss.” The CEO would be so touched by the sob story of the hourly worked, and would buy them a new car/pay off debt/buy them a vacation/start a college fund/whatever. But they would never raise wages or improve insurance coverage or increase sick time.
            I resent this because I’m quiet/reserved/shy but also grew up poor. I wouldn’t be the person sharing struggles, even if there was a chance it would it would generate charity.

  4. Woodswoman*

    As Alison points out, your relationship with your employees is a business relationship. While you may become friends with your employees, that’s secondary and it’s not reasonable to expect them to stay if they have another professional opportunity.

    Your desire to take care of your employees is great. I have been fortunate to work at places where management cared about me. As one example, I had a sudden extended illness and many of my co-workers donated their accrued time to me so I wouldn’t face financial hardship when all my sick leave ran out. But that didn’t mean I should stay there forever. When I moved on to a new job, they all wished me well and I remain friends with many of them years later.

  5. Detective Amy Santiago*

    I am confused. Why was he going overseas? Did he just up and quit to take vacation?

    It might be worth consulting a lawyer to see if the employment contract is enforceable though.

    1. Jesmlet*

      The way they parted ways really confused me. There has to be something else going on here… If OP truly is paying higher than this employee would receive elsewhere and is this generous, there must be a substantial issue somewhere else in this job that would cause someone to up and quit like this.

      I’m wondering if OP is this generous not just for moral reasons, but to also overcompensate for less ideal aspects of the company/job. The only other reason I can think of for leaving a job that’s otherwise great is there was no room for development. Did he get a better title there?

      And yes, look into enforcing that contract. Don’t let people take advantage of your generosity. He knew what he was doing. These are not your friends or family, they’re your employees.

      1. AnotherAlison*

        This is what I was wondering. Markets shift. Could what the OP thought was generous pay now be standard? That still wouldn’t likely offset the extra perks (gifts), but some people would be uncomfortable with that (me). If you wanted to give me a performance bonus, or even a bonus because the company did well, fine, but I don’t want someone else selecting specific things to buy for me. If I could get a job with similar pay and no personal weirdness, I would do it.

        The title bump could be another reason, as you mentioned.

      2. Uyulala*

        I’m glad I’m not the only one whose thoughts went there. Very strange if they are moving to a competitor for less money/benefits (unless it is part of a location move or something).

      3. Luna*

        Yeah the development issue was one of my first thoughts. Having a good boss and nice perks is great, but for a lot of people the best workplaces are those that allow employees to grow, learn new skills, and move up into higher positions.

      4. Tuckerman*

        I was wondering if this is low wage type work (e.g., a barista who makes significantly more than the going rate might still only be making $13/hr). If the owner has a very successful business and the cost of labor is low, it probably isn’t too difficult to give bonuses or temporarily pay full time wages for part-time work. However, that doesn’t mean the employee can make ends meet on that wage (and occasional generous bonuses). Just a thought.

        1. Jesmlet*

          I think the “went to work for a competitor” aspect makes this unlikely as I don’t think a place like Starbucks would include a non-compete in their employment contract (same with most other low-skill/wage work). There aren’t really any trade secrets to steal for the other company that would have any impact, and a low-wage employee would almost never have the reach to send it higher up.

          1. CorruptedbyCoffee*

            Ha! You say that, but I worked for jimmy Johns in college and they have a non compete you have to sign when you get hired there. Can’t work for a competitor or “related industry” for 2 years after leaving.

            1. Tuckerman*

              Wow. That’s an intense non-compete! I wonder if it’s up to the franchise owner or if it’s a corporate thing. (I think JJ is a franchise?)

            2. JeanB in NC*

              I’m pretty sure that’s unenforceable. I’ve heard about their non-compete before and it’s just ridiculous for a fast-food place to say you can’t work at another fast-food place (“related industry”) for 2 years.

    2. Lynn Whitehat*

      I bet he accepted another job with the intention of taking vacation between jobs. But then the new job wanted him to start soon, and there wasn’t time for him to work out his notice and also take a vacation before the new job.

  6. Rachel Green*

    Receiving all that money from my employer would make me very uncomfortable. If my boss was paying for my honeymoon, it would make me second-guess all of my expenses on the trip. And isn’t there some kind of issue here about giving your employees thousands of dollars? Would that money be considered taxable income?

    Personally, I think OP is being way too generous. If you already pay your employees above average salaries, why are you also paying for honeymoons and medical expenses? If the insurance you’re offering to employees isn’t sufficient, then why not change the plan(s) that you offer? I also agree with MariaTeapot above, that the gift giving and money giving should be structured and fair. How do you decide which vacations you will pay for? Or who gets money and how much?

    1. C.*

      Agreed. OP, it is kind of you to do this, but it’s also the sort of thing I would expect from a family member, not someone I work for. If my boss did this, I would be waiting for another shoe to drop, like getting a bill for those costs if I chose to go to another job.

    2. Tableau Wizard*

      Yes! this was my first thought too. I would be so uncomfortable by that.

      I think it’s incredibly generous, but I would feel like I’m taking advantage, especially if it’s not evenly distributed among the staff.

    3. Antilles*

      In usual cases, gifts are not considered taxable income (hence why most couples don’t have to report all the cash they get as wedding gifts). However, since this is coming directly from her employer, I’d expect that it would get counted as taxable income…since otherwise it would be a blatant loophole for companies to exploit.
      That said, the couple still ends up way ahead – yes, you get hit with an extra $400 on your tax bill next April, but the $1600 you *aren’t* spending on the plane tickets since OP bought them more than makes up for that.

      1. Natalie*

        You’re correct. Cash or cash equivalents from an employer are considered income no matter what the amount, and non-cash gifts are considered income if they are above a “de minimis” amount (not set statutorily, but in practice fairly low). An employer who still wants to give a gift can gross it up to account for the taxes, meaning they hand the employee $1,000 but record and report the gift as $1,000+ the required taxes and they remit that withholding just as they would with pay.

          1. Natalie*

            Accountant, so I’m making use of the very dull tax class I had to take. But I have processed payroll. :)

        1. The OG Anonsie*

          But whaaaat if the employer pays a bill directly for you? Like what if the LW didn’t just give that employee cash, but they wrote the check directly to the Sandals or whatever.

          It could go either way, but when I first read the letter my immediate assumption was that the LW purchased whatever was included in the honeymoon (airfare and hotel or whatever) and gifted it to the employee.

          1. The OG Anonsie*

            Oh man, or what if it’s one of those honeymoon registry things where you’re kind of giving cash to the couple but it’s through a third party and that third party actually holds the money and makes the bookings so the couple never has the money themselves?

          2. Natalie*

            That would be considered a non-cash gift, and since it’s definitely above the de minimis threshold it’s still taxable.

            1. Natalie*

              Just as a general rule, if you can think of a way to give money to an employee that seems like it wouldn’t “officially” count as income, the IRS has almost certainly already encountered it and decided it is actually income. That doesn’t mean you’ll be caught or even be in too terribly much trouble if you are caught, but it is still not allowed.

              1. The OG Anonsie*

                Right right, I assumed there had to be a rule here but was perplexed as to how it would work. So essentially, you owe taxes on the monetary value of the thing purchased if it’s over the threshold?

                Is the monetary value determined by the actual amount spent by the employer rather than the value of the thing on the market? And does it matter if the thing being given is provided in some way by the company as part of their business? I’m imagining a scenario where they give you something that they can obtain at a steep discount (or no cost) due to the nature of the business.

                For example, being given a vehicle that used to be part of the company’s fleet but is being retired. Does the employee (or employer?) owe taxes on the value of the vehicle? Or how employees of airlines can get tickets that hooooly crap I just realized that’s why the policy is that you can fly for “free” as an airline employee but you have to pay the taxes and fees associated with the fare at the time you book it. Lightbulb!

    4. Luna*

      Yes, while I think the OP has good intentions and it’s not wrong to want to look out for people, that should be done in the form of high salaries, good insurance benefits and vacation time- and only that. Working out a way to help an employee dealing with a personal or family medical crisis is great and I think more employers should do that (not pay for the treatment, but working out a different schedule or leave of absence if needed is fine IMO).

      But paying for things like a honeymoon or personal bills would make me uncomfortable too, and it might be unintentionally creating resentments among the employees- what about those who aren’t married or were already married when they began working here? Maybe others are also going through family or personal problems and expecting OP to pay for it because OP has done it for others, and they get mad when that isn’t the case. That might not be fair, but if there is an environment of heightened expectations then it is easy for people to feel let down or resentful when those expectations are not always met.

      1. Troutwaxer*

        This is exactly my thinking. If you want to be generous give the best possible pay and benefits, but set a standardized limit on bonuses and gifts such that you won’t be upset or angry when one of your employees does the very normal thing and takes a job that might be more in line with their personal interests, moves because a spouse had to move, goes back to school, starts their own business, leaves to raise a child, etc.

        As for the exact employee you’re complaining about, if an NDA is legal and applicable to their move, you should probably enforce it, but I’d consult a lawyer before you make any decisions.

        Also, is it possible that you oscillate between being very generous and being a difficult boss? Look in the archives for stories about difficult bosses. If you recognize yourself perhaps you have some personal work to do, because employees value a stable and calm environment far more than they value the occasional gift.

      2. Willis*

        Agreed. Also, it may inadvertently become a system that provides greater rewards to employees who are more apt to talk about personal aspects of their life than other are. It’s great to be accommodating in cases of crises or of big life events like a wedding or new baby. But, like Luna said, other employees may be going through family, health, money, etc. problems that they don’t want to discuss with the office. Generous salaries, bonuses, and benefits seem more appropriate than lots of gifting, and keeps the focus on the business relationship side of this.

    5. EditorInChief*

      Me too. I would be so uncomfortable with an employer having that level of involvement in my life that I would start looking for another job. It seems like they’re trying to buy my loyalty. OP you frame it as being generous, but obviously there are string attached based on your reaction to the employee leaving.

      1. essEss*

        I would be really squeamish about my employer having that much involvement in my personal finances that I’d be looking for a new job as well.

    6. Esme Squalor*

      I completely agree. I think the letter writer’s heart is in the right place, but I would also be extremely uncomfortable having professional and personal lines blurred in this manner (referring specifically to gifting a honeymoon to staff). I like to be compensated fairly for my work, and I wouldn’t like to feel like financial exchanges flowing from my employer to me are ever a “favor,” especially one that needs to be paid in gratitude-fueled workplace behavior. If I observed this happening in a workplace, I might take that as a sign that I’m not a good cultural fit and start looking elsewhere.

      1. Anon.*

        Honestly, if I was having medical or whatever thing going on I wouldn’t mention it at work. I hate drama and I dislike being the topic of conversation. I think it would be inevitable that I’d start resenting the extra financial help my coworkers get. Eventually, I’d find other employment. I’m not saying that’s right, but I know myself and despite my best intentions, that’s what would happen.

        1. Mallory Janis Ian*

          Same here. At a previous job, there were two coworkers who discovered that our then-dean was a sucker for a sob story, and they could get what they wanted at work by making him feel sorry for them. It became common knowledge that he would reverse decisions that he’d made based on them crying in his office about their bad childhoods. Others of us had had rough childhoods, too, but we didn’t try to cash in on them by convincing the dean that we were too fragile and delicate not to get our own way at work.

          I’m not saying the OP’s employees are lying or manipulating the situation, but the situation seems rife with opportunity for employees who are more open and vocal to receive numerous instances of financial help, while employees may be more circumspect or don’t want to be seen as assistance-grubbing.

    7. Lady Phoenix*

      Yup. I agree. It is nice to paid well beyond for all my work and especially wonderful that my work has my back during an emergency.

      But the moment they start paying my bills outside of insurance or paying non work personal expenses like a honeymoon? Oh hell no!

      It is kinda like that one dude you may have started dating (or maybe haven’t even dated but thought anout dating… or just a dude who you might be friendly with) who starts dropping tons and tons of money on you. Like gives you expensive presents, takes you out at expensive restaurants, helps pay your expensive bill… Yeah… and those dudes then tend to ask to go steady/marry/fucking.

      People don’t like that because then they feel like they are OBLIGATED to have a far more personal and intimate relationship than they want.

      I bet the dude left without notice because exactly that: you paid his medical bills, he felt disturbed, so he ran for the hills before you could pressure him into something he didn’t want in the first place.

      1. Matilda Jefferies*

        It is kinda like that one dude you may have started dating (or maybe haven’t even dated but thought anout dating… or just a dude who you might be friendly with) who starts dropping tons and tons of money on you. Like gives you expensive presents, takes you out at expensive restaurants, helps pay your expensive bill… Yeah… and those dudes then tend to ask to go steady/marry/fucking.

        I did date that guy, and he turned out to be incredibly manipulative and controlling. He wanted to get married before we’d been together for six weeks, and was talking about having babies not long after that. I was not interested in any of that at the time – and not with him, regardless. It was not a happy relationship.

        OP, this is not to say that you are being manipulative and controlling. But is it possible that your employees perceive it that way, regardless of your intentions? I’m agreeing with some of the others that the honeymoon does indeed feel too generous as a gift from an employer, and it would make me uncomfortable as well.

        I think if you want to continue doing this, you should plan and document a formal bonus structure. Keep it fair, and work-related, and make sure you’re transparent with your employees about how it works. You don’t need to scrap it entirely, but I definitely think you should be more strategic about it.

      2. Esme Squalor*

        This is an apt comparison. Also: that episode of The Office where Michael gives Ryan an iPod.

        OP, if you want to keep your employees from struggling financially, and you’re truly not in this for the beholden feelings, try setting up an employee hardship fund that comes from the company and not you personally, and has a formal application process attached. That will be much more appropriate and still extremely generous.

    8. Yorick*

      Yeah, honeymoons in particular seem off to me. Is OP paying for all newlywed employees’ honeymoons? I assume not, so how are the lucky employees chosen? What about people who were long married when they started work there, do they get long romantic vacations too?

      Medical expenses seems different, as it’s about compassion and helping employees with unexpected expenses, but that can be tricky too. What if someone has huge expenses for a medical issue they wouldn’t feel comfortable disclosing, for example? What if someone hasn’t needed to take much time off for their kid’s illness and hasn’t realized they should tell the boss about the issue?

      It sounds like these must set up a situation where people closest to OP are getting extravagant gifts, which is really unfair.

    9. Nita*

      Yup. Giving money to employees for personal expenses seems to cross some kind of boundary. Paying a high salary is awesome. Allowing extra leave in time of emergency is awesome, but maybe it’s better from a legal/fairness perspective to have policy to that effect on the books, than to decide in the moment someone gets that leave (and someone else who hasn’t shared their personal troubles with you, doesn’t). Funding honeymoons? A little too personal IMO, but again, if you really feel that should be a perk, it should be a policy. Or maybe personal gifts like that should be replaced with a regular bonus for the entire team. Being treated well by one’s employer should not depend on who has the most dramatic life event. It should be fair.

      I don’t think that not going ten extra miles for your employees equals having “no expectations” of having a good relationship with them, or of being a great boss. That’s a very all or nothing way of seeing it. You just have to be more conscious of the fact that you’re already doing a lot for them, but some of the things you’re doing may go overboard and actually create problems. And that to be a decent boss, you do not need to be the person that takes care of their every need. Medieval fiefs and company towns are things of the past, and I think most people want a little bit more distance between their professional and personal lives.

      1. Rachel Green*

        “Being treated well by one’s employer should not depend on who has the most dramatic life event. It should be fair.”


      2. irritable vowel*

        Funding honeymoons also gets dangerously close to discrimination territory – while same-sex couples are allowed to legally marry in the US, they are not universally protected against discrimination in all states. So, some couples may choose not to marry if this company is in a state where they worry they might be fired for asking for spousal benefits. A gay or lesbian employee who didn’t feel comfortable announcing their marriage to the office wouldn’t get the same perk from the boss of having their honeymoon paid for. It also could be seen to discriminate against older employees, who are more likely to already be married — the honeymoon gift disproportionately gets distributed to younger employees.

        1. essEss*

          I’d be unhappy if I was a single employee to watch other employees get thousands of dollars in bonuses simply to go take a vacation after their wedding.

          1. WellRed*

            Me too! I am still irritated by our office manager/HR person’s comment when I jokingly asked when it was my turn for a shower (after several baby/bridal showers, all of which I cheerfully participated in).
            “When you get married or have a baby.” Cause, nothing else matters, I guess?

    10. AndersonDarling*

      I’m all for adjusting schedules, providing extra PTO in emergencies, having generous benefits and salaries, but giving money crosses a line. It’s not clear if the OP is using personal funds for gift giving or if it is the company funds. I don’t know which one would be worse.
      If I was given a huge sum of money for medical expenses and found out is came from the corporate accounts, I would run too. I don’t know if it would be illegal, but it’s scandalous enough that I wouldn’t want to be around when an audit is done.
      Stick to being generous with benefits.

  7. CatCat*

    OP, you sound very kind, but overly invested on an emotional level. Alison hit the nail on the head in the article when she said that “it’ll be better for you and your employees in the long-run if you remember that these are still employment relationships, not personal ones.”

    The example departing employee, who I’ll call Fergus, did not behave professionally when departing without notice and violating the employment contract. That reflects on him, not you. “Geez, Fergus behaved unprofessionally” is really the mindset to have rather than, “Geez, Fergus needs to care more.” And if Fergus is an outlier in terms of behavior when departing, treat it as such, an odd outlier.

    Also, some people may be uncomfortable with the gifts. Generous pay, benefits, bonuses, and flexibility during difficult times are earned and in line with employment relationship, but lavish personal gifts (honeymoons!) may feel awkward for an employee to accept from their boss. So when people don’t seem to “care,” it may be that they just feel weird about some of it. You have a generous heart, but so generous in some respects that it may be an odd experience for an employee.

    1. Luna*

      Your third point is really important- the salaries and benefits might be more generous than what is offered by other companies, but it is not a “gift.” This is what the company agreed to give employees in return for their work, it is a legal contract that the employees are rightfully entitled to and they shouldn’t be made to feel guilty for accepting their paychecks.

    2. Squeeble*

      Agreed on your point about the departing employee, and I kind of wonder if OP’s generosity played a part in him acting more cavalier about his departure than he would have otherwise. I’m not suggesting OP shouldn’t be so good to her staff, but it’s possible he took that as kind of a carte blanche to do whatever was best for him because he assumed she’d be completely fine with it.

  8. irritable vowel*

    Having been on the receiving end, I will say that it feels really uncomfortable to receive gifts that are transactional, which is what this could feel like to some people. It can also be difficult to turn down gifts, especially in relationships where there is a power dynamic. OP, you may see your generosity as paying it forward, which is kind of you. But you’ve also made it pretty clear that you have expectations tied to your gifts – and it’s not unreasonable to assume that at least some of the people you’re giving these gifts to are aware of this. I agree with what Alison has told you, and I would add that I think you should make it *extremely* clear that these gifts are totally optional and that anyone who feels uncomfortable accepting them should feel completely fine declining, with zero effect on their standing as employees.

    1. AndersonDarling*

      Yeah, if my boss gave me $3,000 for a vacation, I’d know that something was expected in return. A gift that large doesn’t buy loyalty, it buys silence/influence/favors.

  9. Interviewer*

    Have you done any due diligence on your industry to find out how your company’s turnover stats compare to your city, region, or industry as a whole? Perhaps your generous benefits are more effective at staff retention than you realize.

  10. Samata*

    Generosity aside, I do think that I would be peeved if an employee left with no notice and then I found out he went to work for a competitor – in direct violation of a contract.

    OP – I think you are genuine in your hopes to help people but I also think you might have some soul searching to figure out what you are specifically looking for in return. Is there a way you can be generous with your funds that don’t involve your employees? Or is there a way that you can makes their lives easier without directly writing a check to them in a time of need? The flexibility of working PT while getting FT pay sounds amazing and I would be appreciative of that but feel awkward if you picked up medical bills not covered by insurance. And, what if you have an employee who never goes through a tough time – do they get a bonus? How do you make sure it’s fair?

    Before I get piled on for saying people deserve money who don’t need it I am simply saying is there anyway employees who aren’t in need of medical/financial or don’t plan to get married or take a honeymoon can utilize this unwritten but often used “benefit”?

    1. Rock Room*

      That last paragraph is what I was thinking. If it were me, I probably wouldn’t think too much about people getting extra money for medical bills, but as I am not married and don’t plan to be, I would be a bit irritated that other people got free vacations and I didn’t.

      I agree with everyone who has said that great insurance (possibly with 100% of premiums paid), great benefits, a good salary, and perhaps a structured, work-related bonus in addition to flexible policies re: PTO would be the best way to handle this.

  11. DM*

    My two cents: Yes, you’re being too generous. Paying above-market rates and providing generous health benefits and adequate time off is awesome. You don’t need to pay for honeymoons (and I’d say you frankly shouldn’t) or give personal loans. If you want to provide your employees with extra perks, make them policy-driven perks with specific criteria and paid for by the company. Make sure that employees know that if they quit without notice, absent extraordinary circumstances such as a serious health issue, etc., that that may mean they are ineligible to return to the company and that you may disclose that for any reference checks. But otherwise, don’t penalize good employees who are grateful for the occasional bad apple or two.

  12. Chatterby*

    Enforce his contract and tell HR to give the damning reference of “He left with no notice during the busiest part of the year and broke his employment contract to work for a competitor” to whomever calls to confirm his employment period. It is 100% true and does not use biased language.
    Then mark him as someone to never rehire.

    1. Catalin*

      The employee certainly misbehaved, but…
      LW, you sound like a perfectly lovely, kind, gentle and generous person. People with that much heart sometimes inadvertently (and undeservedly) cause/let people walk all over them. Was there any way departing employee may have gained the impression from you that leaving without notice and working for a competitor would be fine to do?

      Like the LW earlier today (campus drunk coworker), it is incredibly hard in certain situations to be confrontational or to set (reasonable!) boundaries.

      I honestly don’t know if you’re ‘too nice’ or emotionally overinvested, but could boundaries and clear expectations be a part of the overall problem?

  13. Millennial Lawyer*

    OP, I commend you for treating your employees so well. As an employment law attorney (defense) I’m aware that’s not always the case.

    Perhaps reframe your thinking about this about consider how your behavior impacts the workplace as a whole and you as an employer – does it help retain great talent? Does it create a positive environment that people enjoy coming to work to? Does it make what *you* do feel special and rewarding to give back like that? If so, there’s no reason to dial it down because one person doesn’t want to be a part of that (and an employee saying they are violating a notice policy for “cheap flights” and then violating their contract doesn’t look good for this person).

    On the flip side, there may be reasons totally unrelated to how you are as an employer that made this person want to leave so suddenly/violate their contracts or will make a person want to leave in the future. I can see a situation where someone really appreciated their benefits/employer but had to get out of there because they were being sexually harassed, bad experience with a lower level manager, poor mechanism for reporting incidents, or something else toxic or unfair in the workplace (or in their personal life!) that your generosity wouldn’t fix. Or just another type of life change outside of the workplace purview. Of course there’s no reason to assume that from your letter, but I thought I’d throw it out there just in case.

    1. Millennial Lawyer*

      Also want to add that “random gifts” and paying for honeymoon sounds like a bit much… the generous benefits are enough.

  14. Anony*

    A gift should not have strings. If the gifts are coming with the expectation that they will engender extra loyalty or obligations, the gifts should stop.

  15. Rincat*

    I agree with the others that have asked about how the monetary gifts are doled out in a fair manner. My thought is, if you want to give your employees money beyond their salaries, make them merit-based bonuses that are taxed as part of their salaries, and leave it at that (or offer better health insurance, or flexibility, etc.). No honeymoon gifts. No loans for emergencies. I just see this becoming too fraught – others have pointed out that this could make your employees very uncomfortable because of the power imbalance.

    Also, I dislike the idea of giving employees money for specific purposes. My example is that my grandparents very generously gave me $1000 when my daughter was born. I was very thankful and relieved, because it helped offset my medical expenses. I later found out that they were expecting me to open a savings account for her and were miffed that I didn’t. I was really bothered that their gift came with expectations (and I also was prioritizing not going into debt over medical bills at the present time). Your employees are thrilled to have high salaries and bonuses, but please let them use that money as they deem best for their circumstances.

    It’s great to be generous – it really is! You don’t need to be “calculating.” But just make sure you are being fair and setting good boundaries to protect yourself and your employees.

    1. Manders*

      I agree. OP’s idea of giving out so much money is coming from the right place, but it’s created an odd system where people may be more likely to be given a bonus for having a personal tragedy or a big, uncontrollable life event than for producing great work.

      Also–was the employee’s flexible schedule taken away when his daughter’s health improved? That’s the problem with certain kinds of generosity: people often react more strongly to a perk being taken away than they do to getting the perk in the first place.

    2. Anonymous Educator*

      Yeah, it doesn’t really make sense to say “You have a family emergency? Here’s some money. You’re going on your honeymoon? Here’s some money.”

      You either pay them a fair wage or not. Let them decide what they want to do with the money.

      I do believe the OP is coming at this with good and even generous intentions, but the best thing to do is just give fair and higher-than-market-value salaries, and then let employees take care of themselves.

  16. Lobbyist*

    What I do for great employees is try to make it hard for them to find a better job. Because I realize that if they can find a better job then it’s in their interests to take it. I don’t want to keep them because they are my friends (or worse, my family — they are not), I want to keep them because the job meets their needs. So what that means may be different for different people — one wants more flexibility, one likes recognition, everyone likes money. I try to, within reason and within the needs of getting the work done, give them what they want in terms of work, challenge, travel, public speaking, professional development, etc. and then if they can find a better job good on them! I’ve had a boss that didn’t pay well, didn’t provide recognition, was overly critical about small details while missing the big picture but thought we were a work “family” because he invited us to parties (not at work time, on unpaid free time) at his house! No, I’d rather let my employees use their free time how they want. I can make their work time as productive and meaningful as possible and try to keep them that way.

    1. Rincat*

      This is a good point – money is certainly nice but if my job is not challenging, I’m not learning and growing professionally, then I will likely leave for something else, no matter how good the perks are. I had nearly full-time telecommuting at my last job…but I had terrible management and it burned me out, so I left. Now I come to an office every day, but I have wonderful bosses and a great environment. I had even gotten a really good raise (like 20%) at one point at the old job, but it still wasn’t enough.

  17. Lady Ariel Ponyweather*

    There seems to be some text missing at the end of the second paragraph (or am I just reading it wrong?):

    As he quit during the busiest season of the year,

    OP, you’ve got some great advice and I don’t have anything to add to that, but would like to say that you sound like such a good and decent person. I wish we had more employers like you in the world. Hope you can come to a resolution that works for you.

    1. ThatGirl*

      I think that was supposed to go with the beginning of the next paragraph:

      “As he quit during the busiest season of the year, I pleaded with him to work his notice period at least.”

    2. Murphy*

      I think there’s just an accidental line break there, because the next words make sense as an end to that sentence.

      1. Lady Ariel Ponyweather*

        Oh, I see it now! Thank you both for that, I couldn’t figure it out, no matter how many times I read it. Probably a sign more coffee is needed.

  18. KayEss*

    The worst boss I ever had was incredibly “generous”–in that she handed out gifts that were both expensive and also weird and occasionally self-serving, without any consideration for the recipient. For example, a story that was thrown around the office from before I arrived was the time she gifted expensive spa packages to all the female employees… BUT they had to use them all together, with her, as an hours-long “girl time” excursion, during which she pressured them to buy more expensive services out-of-pocket. She would provide beer for the whole office, and when she found that I don’t like beer but will occasionally drink hard cider, she went out and got an entire case of hard cider–and then got palpably annoyed that I didn’t drink it often or fast enough. Basically, she had zero sense of boundaries and was a nightmare to work for. She also took anyone leaving as a personal betrayal.

    I don’t get the sense that OP is that kind of awful, but I’m sure my former boss also thought she was just being generous with perks for her employees and that we were all friends, how dare we abandon her in her time of need, etc. Maybe that one guy burned a bridge with OP and it’s okay to feel that way… but in general, employees don’t actually owe you anything beyond basic professional norms and the work you hired and pay them for.

    1. JeJe*

      I’m with you on this. This whole thing any paying for medical expenses and honeymoons made me super uncomfortable. I think it’s the lack of boundaries involved. Just give people bonuses and don’t concern yourself with how they’re used.

      Also, no-compete clauses might be the industry norm in this case… But they are terrible. I hope more states outlaw them.

      1. clow*

        yes! non-compete clauses make me question if I want to work for a company. It is like they feel they own you, no one has the right to tell you where you can work when you leave employment.

        1. JeJe*

          Unfortunately, you don’t usually find out about them until your first day of work at your new job.

          1. Natalie*

            Hopefully one of the actual attorneys can confirm, but I believe introducing unnecessary pressure into a contract situation (like presenting someone a non-compete for the first time on their first day) can void the contract.

    2. Guacamole Bob*


      How many letters have we had from people with variations on themes of “my boss is pissed that I quit, am I wrong that employers shouldn’t expect total loyalty at the expense of my career?” or “my employer plays favorites and has no boundaries” or “my employer did X nice thing and now I want to leave – is that ok?” or “my boss acts as if we should be grateful to have our jobs at all.”

      OP, you probably are a wonderfully generous boss, but it wouldn’t hurt to take a step back and ask yourself if you could unintentionally be like some of the bosses from some of the letters here. Any of the above *could* be the case based only on what you’ve written. Hopefully not, but some soul-searching might be in order just in case.

      1. DM*

        I don’t see that being the case here. I think any reasonable boss would be a bit peeved if someone quit during the busiest time of the year, with no notice, to go work for a competitor (in violation of an employment contract –assuming that’s a legal and enforceable provision in the jurisdiction).

  19. Justin*

    You seem like a nice person. You are probably expecting too much, adding strings to gifts as others have said.

    I wish you happiness.

    1. Rachel01*

      I’m wondering if OP is just realizing that he/she might have expectations in regards to the gifts, extra cash, etc. I know I have done something for someone in kindness, than later on feel slapped if they are not willing to do so in return (real rare), but it has happened.

      Just being human we have expectations, some that are unwarranted. This letters shows that the OP is doing some serious self evaluation in regards to this.

  20. anon in ny*

    While I agree that you have good intentions, look at it another way: What if you had an employee who had no medical expenses/honeymoons/etc coming up and you are not lavishing them with gifts. Do the other employees know how much money you are spending on others? This inherently creates an imbalance and I may feel slighted if I were not “in need” while my coworkers got extra money for no reason other than need.

    I agree that bonuses/extras should be merit-based as others have suggested.

    Plus, what industry are you in that you have so much extra money to give to employees? As an employee, I would also worry about becoming financially insolvent if you give so generously. What happens if you lose a major contract and can no longer be so generous?

    It may be uncomfortable to stop this habit but you really must for the sake of your business and fairness to employees.

        1. Rachel Green*

          That was my assumption as well. It sounds like OP has complete control over salaries, benefits, bonuses, etc.

    1. Rusty Shackelford*

      While I agree that you have good intentions, look at it another way: What if you had an employee who had no medical expenses/honeymoons/etc coming up and you are not lavishing them with gifts. Do the other employees know how much money you are spending on others? This inherently creates an imbalance and I may feel slighted if I were not “in need” while my coworkers got extra money for no reason other than need.

      Yes, this is what hit me immediately. If I worked for you and wasn’t getting married, or wasn’t in need, would I feel like others were being rewarded by our employer for something that wasn’t work-related at all? I mean, it’s really lovely that you want to help your employees, but you do need to think of them as employees, not friends, and keep your rewards work-related.

      1. AndersonDarling*

        I’m worried that the gifts are going to the top executives and the actual staff aren’t even acknowledged when they are in need. It’s sad how often a CEO will say “employees” but what they really mean is “Those 4 people I talk to every day. All those other people are grunt workers who don’t count.”

  21. Jady*

    I would say the honeymoon part is maybe a little too much and you may be a little too emotionally-invested.

    But I think everything you’re doing is amazing and I’d encourage you to continue. There are so few companies that treat their employees well, it’s refreshing to hear about such an amazing environment.

    You should definitely examine your retention/turnover rates. I would be baffled if this didn’t have a significant impact in both… unless the job they perform is skinning live cats or something else unspeakable.

    PS Can I send you my resume? Thx

  22. MV*

    I agree with what many people here are saying, don’t get overly invested in employees being grateful or thankful.

    I do get that….but it seems very cold hearted and thankless that when asked for a professional courtesy like serving out his notice period this employee said no. And that No wasn’t because their daughter’s medical issues necessitated it, it was because he could get a cheaper flight (for a vacation?). And to do this after you’ve been paid a full time salary when you have been working part time hours? I am sorry but that does strike me as….ungrateful isnt quite the word but something like that. Its not like the OP was asking him to stay for months or anything more then basic professional courtesy.

    I have a medical condition that can reqiure a lot of long appointments and can flare up. My work has been SUPER accommodating when it comes to teleworking (I work 2 days a week always but at times I can’t drive at all), time off for appointment, etc. They have been very generous with all of us as well (good benefits, salary, perks). I am thankful and it makes me very loyal to them. But even if it didn’t if my employer asks a very reasonable thing of me on my way out I am going to do it. Sure work is not personal but to screw over someone that has treated you well, even in the professional world, makes the person doing the screwing look very bad.

    1. Mediamaven*

      This is so wonderfully put – I’m glad you posted it. While I think this poster is too generous, I don’t think her expectations in exchange for providing a really generous and kind work environment are as out of whack as what people here are insinuating. If you provide a positive work environment with lots of perks, it’s completely natural to expect a heightened level of loyalty and respect in return. That isn’t unreasonable. She likely has to work on removing her personal feelings from it (I’m a work in progress here too) but as a boss, you do nice things in the hopes that it fosters a mutually respectful relationship and that it helps with employee retention.

    2. Letter Writer*

      Thanks. This sums up how I feel.

      I definitely don’t expect someone to pass a great career opportunity or whatever. I do expect people to abide by their employment contracts. I would expect this even without all the extra stuff… But if it occurs after I’ve gone out of my way to accommodate a personal issue, it stings even more.

  23. Scott*

    While it was highly unethical for the employee to not give his two weeks’ notice so he could better extract paid leave and gifts from the writer, especially when giving notice would have been critical for covering his role in the peak season he wasn’t planning to be present for, those were given without expectation of something in return.

    Of course, acting in bad faith like that means that they now have the type of relationship in which it would be perfectly normal to retaliate for his lack of notice and violation of non-compete clause.

      1. Letter Writer*

        I could sue him but it would be at a great expense (legal fees, time) for basically an order saying “hey don’t work there for x months.”

        But by the time the legal process is under way the stand down period would be already over. So I wouldn’t even bother going down this route.

        1. WellRed*

          Sometimes (US here) it’s enough to just notify the new employer that he’s under a noncompete and that works the problem out. But, I don’t blame you if you don’t want to bother.

        2. RTFM*

          You can also sue him for those legal fees, whatever business you can verify you lost because of him, and the extra overtime/temp work, etc. you had to shell out for. And here’s why it’s worth it: you’ll never have to worry about someone pulling that again.

  24. stitchinthyme*

    Unfortunately, the days where it was at all common for a company to try and take care of its employees are long past. In the 20+ years I’ve been in the work force, I have not encountered it a single time, whether I’m working for a large company or a small one, so my philosophy is basically, “The only person who will look out for my best interests is me.” I’m not sure how easy I’d find it to adjust to any other mindset after so long; while I’d definitely be grateful if my company did these sorts of things, I’m not sure I’d feel obligated to them for it.

  25. designbot*

    I would take a look at all those extras in relation to the total compensation. What if instead of windfalls at certain life events, they just got paid more for the work they do?
    I used to work for an organization that was known for incredibly generous raises… but the day to day compensation was deflated because of it. And those bonuses were taxed at a higher rate than our regular salary, so it felt like what we saw listed as the bonus and what we actually received didn’t line up at all. Also, if one employee has multiple kids, weddings, life events, and another employee doesn’t, is the latter less deserving of your generosity?
    I don’t mean to nitpick, because at the end of the day generosity is great in whatever form it takes. I just wonder if it’s not being appreciated by all, is there something in the manner of it that might be contributing to that, and that’s where I’d start by looking.

      1. Naruto*

        Same here. I get above market compensation, probably, after bonus. But because it’s so bonus heavy, it feels unpredictable and uncertain, and it feels like I’m doing less well from paycheck to paycheck. My employer could buy a lot of goodwill by increasing out base salaries and then paying less in bonus — even if the total compensation (after bonus) were less. It’s remarkable to me that they don’t do that, honestly.

        1. designbot*

          Exactly–if I have to put off fixing my car or paying my registration until bonus day, the balance is off. There may be a perception that you should be able to take care of your ill relative or your kid’s wedding without this seemingly outsize generosity by the boss, because your salary should be able to cover life events.

    1. Natalie*

      Just a point of fact as this is a common misunderstanding, bonuses are not taxed at a higher rate than salary. They can be *withheld* at a higher rate, but your overall tax rate is determined by total taxable income. It doesn’t matter how that income is labeled when you receive it.

      1. designbot*

        My point was, you get a smaller check at the end of the day. They say, “but we gave you a $4,000 bonus!” but when you only see $2,000 of it, that rings hollow. If that same $4k was distributed through salary, you’d see $3k of it and appreciate it more.

        1. Natalie*

          Right, that’s the larger withholding. It doesn’t change how much tax you actually pay, though – assuming everything else is the same, you will pay the same tax on $80K in salary or $40K salary and $40K bonuses. In the latter you have two lump sum payments, the bonus check itself and your tax refund when you get the excess withholding back.

          1. Sometimes yes, sometimes no*

            But the two events are asynchronous. What you see at bonus time is a check with a LOT withheld. It may wash out at tax time, but in the mean time, the boss is feeling super generous and the employee is feeling underwhelmed or like the boss’s impression of his generosity is overinflated.

            I think it’s more about psychology and perception than transactional reality.

            1. The Other Dawn*

              Exactly. It’s bonus time here. While I give my direct reports as much as I possibly can every year, what they actually get in-hand is about 60% of what I awarded them. When their bonus is $4,000.00 and they only net about $2,400.00 or less, it’s disappointing for them. They’re not thinking about how much tax they pay for the year, but how much came out of that $4,000.00 check.

            2. Natalie*

              Absolutely, I’m not saying the higher withholding isn’t a real factor in someone’s budget or their perceptions. The misconception I have personally run into when doing payroll (a ton, seriously) is that bonuses are actually taxed more, and the initial wording was ambiguous enough to make it seem like that was present here. That’s the only thing I was speaking to.

  26. Naruto*

    I think you’re making this too personal, and so in a way, you are being too generous: you’re giving them all these extra, random, personal gifts. How about, instead, you give try to be more generous as an employer rather than personally? So: give them better base compensation; give them better bonuses. Take the money you’re using on honeymoon gifts, etc., and put it toward that.

    I also think you’re taking their actions too personally. People leave jobs. This is fine! The person who gave no notice and breached a noncompete agreement is being unprofessional. There’s no need to worry about whether they’re also betraying you personally; they’re behaving poorly even just as a professional. It will probably hurt less.

    Also, ask yourself why someone would leave your company for a competitor. It’s possible that this weird personalization of yours is making them uncomfortable. It’s also possible that you think you’re beating the market on compensation and benefits, but you’re not, and this sort of “extra” stuff you’re throwing in doesn’t change that fact.

  27. Ms. Ann Thropy*

    None of the employees was uncomfortable enough to turn down the money. Presumably OP didn’t force the money on them. Why is none of the wrong in this on them?

    1. Esme Squalor*

      I don’t know about you, but I would have difficulty turning down a gift from my employer. It would just be too awkward due to the power imbalance. I’d also worry about offending them in doing so, especially if my refusal had any flavor of feeling that the gift was inappropriate–it would be mortifying to be put in the position of instructing your employer on appropriate workplace behavior, and there’s no way that would just blow over without a problem. Also, the people offended by these gifts the most may not be the recipients, but the people NOT receiving lavish presents.

      That said, it’s perfectly possible that none of the employees have an issue with the letter writer’s gifts. But at the end of the day, it’s always on the employer to adhere to appropriate workplace behavior, and if employees elect to not police their employers, that’s completely fair and understandable.

    2. Danger: Gumption Ahead*

      I don’t know that there is any wrong on anyone in this. Employer offered to pay for things and employees accepted. The issue is the employer’s emotional reaction to people leaving after accepting gifts and only the employer has to power to change that

  28. SallytooShort*

    Taking this from a totally different angle, you could also see this investment in employees pay off even if they leave you. I don’t know what business you are in. But if they end up in-house to a company you could service they will always have a good word for you. If they end up at a competitor* they might be able to refer you if they have to turn down a client (this happens with some industries where there are conflicts between clients or they are just too full.) There are a million other ways a strong network base who always remembers you fondly could pay out in the end. Even if they don’t stay with you forever.

    *In a right way. I am NOT condoning the person breaking the terms of his employment contract

  29. Bea*

    This hits home as an employee who becomes incredibly protective of employers. I’ve seen my former employers taken advantage of by some over the course of my career but in the long run the ones you keep forever will be worth it. I still do things in new jobs because I’m invested in being great in honor of everyone who invested in my success.

    It’s absolutely one of those things you can’t go into it expecting they’ll be loyal and grateful to the very end. Anyone who leaves you in the lurch and bounces at a bad time still most likely be better off out of your life and business, they’re easily replaced by someone who will be thrilled with your kindness.

  30. Tretinoin Newbie*

    Yes, you’re being too generous. If you’re paying well, offering ample benefits, awarding bonuses FOR good work, and treating your employees with respect, that’s enough. As others have wondered, how are you rewarding those who don’t have issues or some type of life event?

    Diatribe: I know this is my personal bias, and I will write it anyway. It’s annoying that those with problems seem to get all the attention or help. Especially when those problems are because of their own bad decisions (not talking medical here). Can’t pay your rent, here you go. It doesn’t matter that you went on a cruise last month or get your mani/pedi every two weeks. Can’t pay your mortgage, here you go. It doesn’t matter that you bought ‘too much house’ for your income. Can’t buy food for your children, you’re eligible for this or that. It doesn’t matter that you knew you couldn’t afford more mouths to feed two children ‘back.’ Can’t pay your credit card bill; there’s a program where credit card companies have to write it off. And so on, and this help comes from sundry programs and/or individuals. A question was posed recently about how one would spend lottery winnings. I would help those who seem to need no help ( i.e., those who don’t earn a lot, but pay their bills on time, those who purchase homes commensurate with their salary, those who go to work everyday, but can’t afford to purchase a car). In other words, I would reward people who are trying to be responsible members of society, but need help. Ok, enough. Commentariat : please don’t respond to me saying that ‘ it’s not the children’s fault’ or anything along those lines; I know that, and it still PMOff.

    LW, you sound like a grand human being, but some don’t appreciate kindness. In fact, they may see it as something to take advantage of, and you end up feeling lousy. Stop it, and simply be an awesome employer, nothing else.

    1. Bea*

      My response to “how to spend lottery winnings if you never had to work again” is always “keep working because I love my job. Take minimum wage and give the rest of my salary to my co-workers.” they deserve more. Everyone could use a few extra an hour in my experience.

  31. Rachel01*

    I would cut back. Forget about honeymoon expenditures, etc. I’m single and plan to stay that way, if I saw my employer paying for honeymoons, and I wasn’t getting a paid vacation I would feel left out and slighted against.

    I would limit yourself to yearly bonuses, maybe bring in a massage therapist one day a month. Since you are paying them above industrial standard I would limit the amount of extra cash you give them. There are ways that you can show appreciation without going overboard.

    As an employee I would love it, but it would make me feel an obligation to do more for the employer than was required by my job. One would be never leaving, passing up on a job elsewhere that would offer more professional development, etc. If you were paying for specialized training, that would be one thing where you could require that they remain in your employment for a minimum of six months or a year upon completion of it, or be required to reimburse you.

    I am also afraid that your employees might take advantage of your generous nature. My father had an employee whose son was paralized in a ATV accident. He had only six employees, and this was his first year running his own business. It was a hardship but he paid her medical insurance for 3 months while she didn’t work. He was terribly upset when she came back to work for a few days and than submitted her resignation. He felt like he was taken advantage of. (She had received a large settlement from the insurance company; he should have been expecting the resignation).

  32. The Other Dawn*

    I think OP is a bit too generous. Better pay, good insurance, generous time off and bonuses are great and every employer should do that; however, paying for honeymoons, tuition for employees’ kids, personal gifts, etc. seems to be over the top. I’m not necessarily saying don’t do it, but I wonder: do people stay because they get all these goodies and see dollar signs, or because they like their jobs, the boss and the company and the generosity is just the cherry on top?

  33. Globetrotta*

    Assuming pay and benefits are already generous, would there be a downside to some sort of crisis fund, where employees could request extra assistance in case of hard times not met or fully covered by health insurance, leave, life insurance, etc.? Maybe even allow employees to pay it forward, sort of like a leave bank?

  34. Letter Writer*

    LW here. Thanks for posting my question, Alison. I learn a lot from your website and I appreciate your thoughtful response to my dilemma.

    I agree with your advice. But having human emotions I also can’t help but feel hurt in instances like these. And honestly, yes, there is an element of “how can you behave so atrociously after I went out of my way to help you?” The easy answer is to stop being nice and have nothing other than professional expectations. But whenever I hear someone’s struggling my instant reaction is “What can I do?” I have a hard time doing nothing when I know I have the resources to give some relief to those who do not.

    I’m not sure what the solution is to that.

    Also, some clarifications:

    *Honeymoon: when two employees started dating, I jokingly said if they got married I would pay for their honeymoon. From then it became an unofficial “perk” – if you met someone within the company and got married, I offered to pay for their honeymoon. All three couples were long term employees and had a personal friendship with me outside of the workplace. I certainly didn’t get the impression they thought it was creepy or inappropriate. If they expressed such sentiments I would not have paid for it. There is no obligation to accept.

    *Enforcing the terms of the employment contract would require a time consuming lawsuit and expensive legal fees. I wouldn’t go down this path. I trust the staff to be professional and give proper notice. When they don’t realistically there isn’t much I can do.

    *I do not reside in the US so the comments about tax don’t apply.

    1. Rachel Green*

      When someone is going through a hard time, you are already helping them by being a good employer and offering generous salary, benefits, time off, etc. There’s no need to go above and beyond by paying for everything.

      Regarding the honeymoons: I think it’s inappropriate to pay for these trips, because it’s only a “perk” you’re offering to “long-term employees” you have a “personal relationship” with. You’re also encouraging and rewarding romantic relationships in the workplace. It’s also very unfair because those who are single, already married, or getting married to someone outside the company are being left out.

      1. Letter Writer*

        I appreciate what you’re saying, but I disagree. This is six people who got married out of the hundreds who worked with me over a period of 20 years. Also, all the managers already receive personal travel allowance as part of their remuneration package. So paying for honeymoon flights and accommodation is not unusual in the context of all managers receiving travel perks already on an annual basis.

        My question here is also about being overly generous with my staff and not whether or not I should pay for honeymoons specifically (last of which happened ten years ago), so I would appreciate if we can agree to disagree and go back to the main topic, thanks.

        1. FYI*

          But paying for honeymoons IS being overly generous with your staff. It’s the same thing. It IS still on the “main topic.”

        2. caryatis*

          You’re effectively paying employees who choose to get married while they work for you more than those who are single or already married. That is clearly unfair and I bet it’s pissing off a lot of people.

        3. Dono Vorrutyer*

          Whoa. You are paying more to employees who get married to other employees, while they are working for you, than to still single/already married employees. That is extremely generous to that handful of employees, but really unbalanced for everyone else.

        4. Scarlet*

          Hum, of course it’s unfair to give perks specifically to employees who are also your friends. You can “agree to disagree” all you want, but don’t complain if it breeds resentment from the other “non-friend” employees.
          Of course, your friends were ok with it, but I’d be curious to hear what the other employees had to say about it.
          Treating some of your employees differently based on a personal relationship is a pretty serious breach of professional norms.

    2. MommyMD*

      You are way too personally involved with your employees. There is a lack of boundaries that one day can have serious consequences. Not only legal, but personal. You have no idea if right now one of your quiet employees is seething inside about all this inequity. Workplace violence is a real thing.

      You are their boss. Not their father or their best friend.

    3. SallytooShort*

      I think the employee who left without notice and broke the terms of his contract is just plain wrong. Hopefully most people aren’t like that.

      Some people will leave who don’t do it in the wrong way. And I wouldn’t look at that as a betrayal. I would see this person as a potential asset in a lot of other ways.

    4. beanie beans*

      I appreciate that you’re asking “what can I do” when someone is struggling. I think the transition to being a little less generous might be tough since you’ve already been giving so much in the past, but I think it’s possible.

      Maybe the answer to “what can I do” is to keep doing some of the non-gift related things that you’re already doing – being flexible about time when people need it, continuing to offer good salaries and bonuses, being an understanding boss when people are going through a difficult time. These are all huge for employees and by themselves might retain good employees longer.

      And yeah, start transitioning away from encouraging coworkers to date… The way you’ve worded it sets you up for a lot of unbalance and potential conflicts in the future if the relationships don’t work out. Treating employees well also means treating people fairly and equitably.

    5. Competent Commenter*

      It’s so nice of you to join the conversation, Letter Writer. I just wanted to respond to your comment that the “easy answer is to stop being nice and have nothing other than professional expectations.” That’s very black and white thinking and it sounds like it comes from a place of pain over past experiences. There’s lots of room for nuance. Your impulse to help when someone is hurting is wonderful. Just try channeling it a little differently so that boundaries are clear.

      Also, exploring your point further, we’re not responsible for helping everyone to every possible degree. It’s okay to help a certain amount and not further. It’s not being mean; each of us deserves the autonomy of choosing when to accept help and solving our own problems. If you help people within a professional context through providing a great work environment, benefits, etc., you’re already helping, and you’re making the world a better place.

    6. Natalie*

      Somebody upthread mentioned the concept of a hardship fund with an actual application process. I know that might sound a bit bureaucratic, especially for a small business, but it could potentially provide a way for you to help people in a jam while removing the potential for (real or perceived) favoritism.

    7. Mediamaven*

      As a boss myself, I hear you. It’s nice to assume bosses aren’t human but we are, and in many areas of life outside of the professional environment you do nice things for people with the hopes that it fosters a mutually beneficial relationship. It’s challenging and difficult to remove feelings from the workplace when you want your staff to enjoy coming to work every day. I’ve been there, so I sympathize with how you are feeling. I definitely am not as generous as you but I’m taking this year to reevaluate all of the extras I provide because it doesn’t seem to impact employee retention.

    8. JB (not in Houston)*

      You have to be able to get some professional distance if you are going to keep offering these perks. It’s ok if, at first, your initial reaction is to feel hurt when something like this happens. But if you want to keep offering those kinds of perks, then you need to find a way to not take things personally. Yes, you have human emotions, but we all have human emotions that we are expected to keep in check in the workplace.

  35. Anonymouse*

    I think the spirit of your generosity is amazing, but the execution can cause hurt feelings and resentment. For example, what about the employees who do a stellar job, but don’t happen to have any milestones or life events on the horizon? Are they being fairly compensated compared to the employees you’ve given extravagant gifts to?
    Also, you’ve blurred the lines so much that your employees won’t know when they’ve crossed it, like your employee that left abruptly. You’ve been so generous giving him time off, how was he to know that your generosity didn’t extend to being ok with no notice period?
    You can be generous in a way that gives your employees peace of mind and gratitude: performances bonuses, paid time off as defined in your employee handbook, excellent health benefits, etc, and I think you’d all be better off in the long run.

    1. MommyMD*

      Agreed. And I think LW needs to delve deep to see where this compulsion is coming from. A need to be “friends”? To be the “best ” boss ever? This is unhealthy behavior for everyone involved.

      1. The Other Dawn*

        That’s what I was wondering, too. He doesn’t mention personal relationships, but what were his friendships like when he was younger? Did he feel like he needed to be very generous in order to keep friends? Were friendships one-sided?

  36. JoJo*

    So leaving without giving notice to an employer is a sin, but it’s okay to fire an employee without any notice? Hypocrisy much?

    1. Natalie*

      Since the OP says upthread they’re not in the US, it’s entirely possible that they do have to either give their employees sufficient notice or pay out some kind of notice period.

    2. Augusta Sugarbean*

      Of course it’s okay to fire someone without notice. There are plenty of legit reasons why you’d fire someone immediately. If someone assaults me in the workplace, why should they get to work out two weeks?

      But assuming a non-emergency situation like a performance issue, I think the counterpart to two weeks’ notice is being put on a PIP and given a chance to improve before firing.

  37. MommyMD*

    Yes. You are crossing many personal boundaries with your staff, over and over. And it may be viewed as being unfair to other employees. Which it is. Be a decent boss, offer decent PTO and provide a functional work environment. This singling people out and throwing money at them is going to backfire very badly one day. At the end of the day, you are their boss. Not their best friend. Some counseling may be in order to find out why you feel compelled to do this.

  38. Competent Commenter*

    OP, you sound like a very nice person who is trying to do the right thing. You certainly don’t need to be more calculating. I hope that the feedback you’re getting shows you instead that there are different ways of being nice, and that in the context of a work relationship, it’s best to be nice in a professional way, rather than in the way you’d be with family or friends. It’s actually nicer, because by blurring the lines you are almost certainly making some or most of your employees uncomfortable even though you’re meaning the exact opposite. So instead of thinking of being more calculating, think of it as being even more considerate than you already are.

    So, I really like the advice to improve your health insurance plan, fund life insurance policies, PTO, etc., to basically maximize all the normal benefits that employees might expect. Keep it professional. It’s so much more comfortable, reliable and transparent for everyone involved.

    I’d also add that in addition to worrying about someone expecting something extra in return me if I get a huge gift such as a paid honeymoon, there are other ways it would make me feel uncomfortable. Accepting those kinds of gifts would make me feel like a bad person because by blurring the professional-personal lines, you’d making me also blur those lines, and I don’t like that, and don’t want to be a person who does it. And also, I know from past experience that if big gifts are in the offing, I start to feel very acquisitive. I want those gifts. I’m thinking about them, and wondering if I’m doing something that will get me a gift. If I mention that I need a new car, will I get one? Should I mention it? Oh yuck, I mentioned it. I feel sleazy, but I just couldn’t stop myself. And then if I get the car, what kind of person does that make me? If you’re an ethical person, this dynamic just doesn’t feel good at all. It didn’t even feel good when the dynamic was with my difficult grandmother, and it would feel worse if it was with my boss. It might even make me resent or dislike my boss, which would be rough since my boss is so nice. It’s a mess.

    Channel your impulses differently, and keep being the good person you are. :)

  39. e271828*

    LW, it sounds like your impulse to shelter and be generous goes way back into your own past, and you need to confront and control it and channel that impulse appropriately.

    Others have remarked on the unfairness of paying for honeymoons for some employees, on the uncertainty your generosity creates, on the silent burden of expectations of emotional return. You cannot buy love with money. You cannot rescue everybody from everything. You are the boss and you can best earn your employees’ respect and loyalty by being an excellent boss. Do not overpay; you’ll look like a poorly-informed sucker. Do not lavish gifts and assistance on some employees but not others. You’re creating a situation with erratic rewards and that is going to go toxic (may already have done, if your employee felt it was okay to walk out after you’d paid out so generously).

    Ways to channel this impulse appropriately include: bonuses, if at the end of the year the company’s work has merited them; a hardship fund with an application process and a committee (not just you deciding); local community charity activity; solidly top-of-the-line standard benefits, and scrupulously fair and egalitarian salary and employment practices.

    Best wishes to you, and I hope you can focus on being a good boss, the best boss you can be, going forward. That’s what they really need from you.

  40. Letter Writer*

    Hi everyone, me again.

    Thanks again for everyone’s comments. It’s given me a lot to consider and reflect on.

    Another episode that comes to mind: One of the managers, Fergus, resigned last year. He was going to start his own business in an area with zero experience, and his business plan sounded…dubious. I was worried about how he was going to support his family so spent a lot of time talking through his plans, pointing him out to various resources, etc. He gave a six week notice and asked to work part time so he could focus on his business set up. I agreed, and also offered to continue to pay him for three months on full time wages after his last work date, as a thank you for your service.

    Bizarrely, Fergus began telling people: “I don’t want to leave this place. I went on holiday for two weeks and when I came back [Boss] said I had to go and that she’d already found a replacement. I’m devastated this happened after working here for so many years.”

    I was truly dumbfounded. Besides this making me look like a jerk, we have strict employment laws where this kind of accusation could cost tens of thousands of dollars. Normally an employee who makes this threat would get a pay out, even if untrue, just to avoid a costly legal battle. I wondered why Fergus said this – was he trying to get more money? Was he worried about his business and wanted to find a way to come back without losing face? I don’t know. When I confronted him he started crying and said he doesn’t know why he said that.

    To reiterate, I don’t expect employees to stay working with me forever, or pass up on a good career opportunity elsewhere, or work with crappy pay in return for random gifts. There’s been several ex-employees who moved onto bigger roles after their experience working at my company, and I’m really happy for their success. I still keep in touch with a lot of them.

    But the fact that I spent so much personal time coaching Fergus, offering him extra pay so he wouldn’t go into debt while his business was starting up….wow. I was really upset he started spreading rumours. My expectation, I suppose, is that people don’t behave like jerks after I help them out. Is that unreasonable?

    1. Tretinoin Newbie*

      No, it’s not unreasonable, but since you say they ARE being jerks after you help them out, please stop it for your own sanity.

      Some of your employees may feel as if you ‘owe’ them, and your help/gifts are ‘what you should do.’ Ughh These employees will not display much gratitude or loyalty, and that seems to be what you want.

      Some may be grateful, but they are not expressing it in a way that resonates with you. Haven’t you read The Five Love Languages?! :))

    2. Manders*

      That’s incredibly weird behavior on Fergus’s part.

      This might be hard for you to suss out as the business owner, but is it possible that there’s a toxic situation going on in the company that you don’t know about? Have you noticed turnover and bad behavior across the board, or just in a few departments? You’ve talked about having long-term employees you feel close to, so you might have a problem on your management team that employees feel like they can’t bring up with you because you’re giving them the impression that you’ll do anything to protect your friends.

    3. Pollygrammer*

      I wonder if your support meant Fergus felt he ~had~ to commit to his business plan when otherwise he might have (rightly) second-guessed himself? I’m guessing there was a point in time when he genuinely didn’t want to leave, but felt he had already made his bed–and that was a bed you helped him make both personally and financially.

      He was absolutely a jerk, and you definitely meant well, but your extreme support of his maybe-less-than-practical dream may not have ultimately been a good thing for either of you.

    4. FYI*

      Yes! It is in fact unreasonable! There is a level of enmeshment here that throws the balance way out of whack in your relationships. If Fergus wants to start a business, let him figure it out. He is a grown-up. Haven’t you ever heard that parable about the kid who “helped” the bug struggling to get out of its cocoon? The kid killed it, because the struggle was just what the bug needed to grow big, beautiful wings. No struggle, no wings.

      I say this with kindness, really: You don’t need to help everyone. The “help” you’re describing is waaaay over the top. Three MONTHS of full-time pay AFTER his last day?! No. Sorry, but there is something else you’re trying to work out here.

    5. Lilo*

      You sound like a nice person, but I think this is too much. You were trying to mentor someone in his process of leaving his company and offered him extra pay to leave?

      Pay people for the work they actually do. That’s fair. Setting up donations for people with serious health or financial issues? Fair.

      Throwing extra resources for people out of luck (they met at work) or because they’re leaving? Too much. There’s a line between being a good employer and going over board, and I think you’re going overboard. I agree with the poster above who suggested channeling your efforts into a charity or similar. That keeps professional boundaries firm and makes sure your money goes to people who actually need it, instead of Ferguses.

  41. Woahh*

    I kind of think if you’re going to be that nice you also have to be equally tough- which means when someone leaves in a shitty way and works for your competitor against their contract, you enforce the penalties.

    Also, don’t impoverish yourself for other people. Wounded healing isn’t a great way to go through the world, if you’re doing aspects of that.

  42. Pollygrammer*

    OP: I think your impulse to help is fantastic. I’m wondering, though, if you can channel it towards people in need who aren’t your employees?

    There are lots of ways to be charitable that still involve personal interaction. I’m thinking, for example, of programs that will share underprivileged kids’ Christmas wishlists; participating in something like that is very personal and very rewarding. Get involved in helping with medical expenses for families in need. Adopt a mentee or five from a local community college. Or even buy coffee for a bunch of people in line behind you.

    Things like that will keep your desire to help people out of the workplace, and away from potential ingratitude from your employees, which sounds really painful. You definitely have my sympathies.

    1. Willis*

      Yes! This is what I wanted to suggest. Being charitable is great and so is being a generous boss/business owner. But it’s weird to be giving giant gifts (honeymoons, months worth of salary to someone who quit, etc.) to employees. Why not find organizations dealing with issues you care about and give your extra money or time through a channel that’s already set up for that purpose? You can still have generous pay, bonuses, benefits, etc. without the gifts for employees. Keep your work relationships on a business level.

  43. Diamond*

    I’ve never known a company to pay for honeymoons and personal things like that, I honestly find it really bizarre! I’d stick to business-related generosity (wages, bonuses, benefits etc).

  44. FYI*

    Too enmeshed, OP, sorry. I’m not calling it “too generous” because OP clearly states that the payouts are to compensate for a sense that his parents were screwed over. It’s just best to work that stuff out separately and not proxy it into the current staff dynamic. There’s no way to fix what went on with your parents — and the current dynamic is inherently (and grossly) unfair to staff who have no major life events to “fix.”

    1. caryatis*

      > the current dynamic is inherently (and grossly) unfair to staff who have no major life events to “fix.”

      I agree! I’d be pretty pissed off if my coworker got a lavish gift like a honeymoon and I got nothing. There’s a reason why bonuses are generally given to everyone at the same time of year.

  45. Memory Lane*

    This situation made me reminisce about my ExBoss from Dysfunctional Job. She made certain gestures of generosity, telling us she gave us higher-than-market salaries, happily informing us about bonuses, telling us we had been given a generous leave policy, being flexible with unexpected life events that required leave from work–all the while trying to establish/expecting personal friendships with her employees.

    In actuality, our pay was still low enough that made it hard to find housing in a high cost-of-living area, bonuses were sporadic and never more than a fraction of month’s rent, our leave was the bare minimum required by law and pretty stingy and she gave us no schedule flexibility (which would have been one of the easiest benefits to give especially since we were a non-profit), and we had to persuade her to include a dental plan in our health insurance. On a personal level, she gossiped about all of us and shared our personal information with all other staff, tried to sow division and distrust between employees, was capricious in her decisions and changed her mind on important matters all the time.

    She thought she was being super generous and kind to us, and expected us to be docile trusting automatons in return, forever grateful and indebted to what she thought was generosity and wise management. Everyone was desperately job searching. A couple people had been the targets of personal attacks and direct abuse; they both left with less than a week’s notice.

    LW I’m not saying this is you. A lot of others have pointed out how cash or in-kind gifts create problems because of power dynamics and real issues of fairness, so I won’t repeat their comments. I will say: keep being generous with wages, be generous with benefits and whatever else that everyone can use and have access to regardless of marital or child status.

    But be careful that you don’t let your perception on how generous you’re being color over the ways that employees are treated.

  46. GreenDoor*

    The OP also needs to take care that generosity doesn’t turn into getting used. The extra time off packages or cash gifts should be rare. OP shouldn’t get to the point where they feel they have to fund/solve/invest in every employees’ hard times. And you don’t want a situation where people start assuming they’ll get extra sick leave or pile of cash. You’d also want to avoid infighting like, “You gave Jane $1,000 for her problem but you’re only giving me $500. Do you like her more than me??”

    I agree with Allison that being thoughtful and doing your best to accomodate the personal needs of your employees is a great way to keep morale up and retain great staff. But don’t get used and abused in the process!

  47. Safetykats*

    I know I’m dating myself here, but I’m reminded of the Friends episode where Rachel, Joey, and Phoebe can’t afford the concert tickets. It might feel good to be the one with all the money, magnanimously handing it out to those less fortunate, but that doesn’t mean it feels good to the folks on the receiving end. In fact, it would probably feel better to most employees to have better well-defined benefits, or a higher salary, or a predictable bonus program, than to be beholden to or dependent on the generosity of the OP. The kind of gifts being given set up the expectation of something beyond a normal employer-employee relationship, and while the perks might be nice, it’s got to be uncomfortable for a lot of employees. I can see how someone might wind up just wanting to get away – from what is perhaps an overwhelming sense of obligation, if nothing else.

    That doesn’t justify the employees actions, but I think it makes him only human.

  48. Nik*

    It is difficult when an employee seems ungrateful when you have done all you can to be the world’s greatest employer. But I wholeheartedly support your generosity. For every ingrate you will have several who will be loyal, especially those who know how stingy other employers can be. Guess who will have the most tenured, knowledgeable, and valuable employees? You, of course! I sense you already know what is best for your company’s long term health and it isn’t being like all the other employers out there!

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