how do I manage an employee who doesn’t need the job?

A reader writes:

I have a very small company with only two employees plus my business partner and my wife, who does the accounting. The most senior of my two employees is Jean, whose husband is a very highly paid professional and her family is wealthy. Before working for me, she dabbled but had never had a real job.

Jean is quite brilliant, but has made it clear several times in the four years she’s been with us that she doesn’t work for the money, but works because she loves the job.

I feel that we have no leverage over her at all. Recently she decided that she wanted to be home with her teenage children for a whole month before one of them goes out to boarding school, and she announced that she was taking a month of unpaid leave. I realized that had I refused, she would have simply quit, and that would be disastrous for the business because of the institutional knowledge she holds and all our clients love her and always sing her praises. We would also probably have two hire two people to replace her, because she’s very versatile (graphic design, copywriting, strategy, account manager, etc). This situation makes me uncomfortable and I don’t know how to go about it. What do you think I should do?

You should manage all of your employees as if they don’t “need” their jobs and have other options — whether those options are family money or the ability to go out and get another job with their skills.

There are two reasons for that:

1. Assuming you’re hiring good people, it’s very likely they do have other options. It might be a pain for someone to leave and find another job, but generally it’s something people are able to do.

2. Using someone’s paycheck as your primary leverage might be effective in the very short-term, but it’s rarely a way to build or retain an engaged, invested staff in the long-term.

The way you motivate someone who doesn’t need the money is the same way you should motivate people who do need the money: by giving them meaningful roles with real responsibility where they can see how their efforts contribute to a larger whole, giving them an appropriate amount of ownership over their work and input into decisions that involve that work, providing useful feedback, recognizing their contributions, helping them feel they’re making progress toward things that matter to them, and — importantly — not doing things that de-motivate people (like yelling or constantly shifting goals or generally being a jerk).

It sounds like your concern is that Jean might feel she can do whatever she wants, including things like just announcing she’s taking a month off rather than asking (and not giving you any real choice if you want to retain her). And maybe you’re worried about how else that could play out — for example, what if she decides she’ll only stay if you fire Client X (or Employee X) or if you use her sister’s catering business for the office party or if she can work just three hours a day and wear a sparkly dragon outfit to work.

But the thing is, everyone who works for you has deal-breakers, things that they’d leave over if they don’t get what they want. Jean probably just has more of them than other people, because she doesn’t need the paycheck. The choice for you, though, is the same as it would be with any other employee: you’ve got to decide if what she wants is something you’re willing to accommodate in exchange for being able to keep her working for you.

The best thing you can do, for both you and Jean, is to be very clear-eyed about what you are and aren’t willing to work around. That doesn’t need to start as an absolute statement of “You cannot do X”; it usually should start as a conversation — something like, “I know that taking a month off is important to you. I’m concerned about the timing because we won’t have a way to cover Y while you’re out, and I’m concerned that we’ll be setting a precedent where if we approve it for you, we’ll have to approve it for others. But at the same time, you do great work and we want the job to be one that fits in with your other priorities in life. Is there a different way we could handle this so we’re both getting what we need?” Who knows — maybe Jean will say she could still handle Urgent Thing Y from home that month, or come up with another solution that makes it more workable for you. Or maybe she’ll say no, this isn’t something she’ll compromise on. If that’s the case, then you’d need to decide if it’s better for your business to have her away for a month or to lose her entirely.

And that’s always going to be a complicated question because you employ other people. They’ll be watching what Jean gets to do and potentially feeling resentful if she has a different set of rules than everyone else. So you need to factor the impact on other people’s morale into the overall calculation you make about what’s right for your business.

But the point is to have an honest conversation with Jean when this stuff comes up — here’s what she wants, here’s what you need, and is there a path forward that works for everyone? If there’s not, that’s okay.

That part — the “if there’s no path forward, that’s okay” part — is really, really important. Right now it sounds like you feel held hostage by Jean — that she can do whatever she wants and you have to accept it because it would be disastrous if she left. That’s a bad place to be, and you can’t stay there if you want to run things effectively. Jean will leave at some point, because all employees leave at some point. If that means you’ll have to hire two people to replace her because of the amount of work she does, start planning for that now. If your business relies on having one magical person who does the work of two people, that’s not sustainable no matter how committed they seem — because things change. People get sick, are hit by buses, move, take on new family obligations, get better offers, change their goals in life, etc.

Similarly, if Jean’s institutional knowledge isn’t documented anywhere, make it a priority to change that. If clients love her and would be upset if she left, start building your network of other people with great client service skills so that you’re not starting from scratch when she leaves (because again, she will leave at some point). Your business plan can’t be “keep person X at all costs” because that will always, always fail at some point.

And this isn’t just about Jean. The best thing you can do is to assume everyone will leave at some point and plan accordingly, and get in the habit of having honest conversations with all of them about what you can and can’t do to accommodate the things they want from their jobs and the company. The framework you want isn’t “how can we keep this person/control this person at all costs” but rather “let’s see if we can figure out a way for our interests to continue to align.”

{ 355 comments… read them below }

  1. quill*

    I think there may be a little more wrong than just your relationship with Jean if your thought is that you need “leverage” to manage an employee.

    1. Jean*

      Yeah, that jumped out at me too. Sounds like this OP only feels comfortable with a firm upper hand that they can exploit at will. Yikes.

      1. cubone*

        lol, I very much agree with your comment, but it’s very funny to imagine you are the Jean in question popping in here innocently

        1. Former Child*

          And Jean could get hit by a bus, so there are lots of reasons to act on this. Like, ask if she’ll train an “assistant” — esp. when she’s gone. She’s inviting you to hire someone to learn her job, since she’s taking off a month.
          Then, work on helping that person make Jean less “irreplaceable.” Treat it as you helping Jean as well as being a temporary necessity.

          1. Okay, great!*

            This is a good idea. The OP might just not know any other way to view employee/employer relationships than a “leverage” situation. That’s what this sight is so good for! Explaining all the possibilities, and bringing out the human side of work.

        2. Jean*

          Lmao, I totally whiffed that. I am not the Jean from the OP, although I’d be lying if I said I’d never fantasized about being an employee who held all the cards in my relationship with my employer.

        3. Amethystmoon*

          Everyone should have at least one person who can fully cover for them when they’re gone. I have had two jobs now where I didn’t have that, because they didn’t have the skillset, and I felt like I could never take vacation time more than 1 or 2 days, at most. I think the key is to tell Jean that she should be able to feel like she can be gone for a couple of weeks, but there is someone who knows how to do her day-to-day job duties also. If that requires training and/or documentation, that’s normal. But everyone should be able to use their PTO time.

          1. PollyQ*

            Even having the tasks spread among a couple people is a good enough backup plan. But a situation where the business would be devastated if one employee leaves needs to be dealt with immediately.

          2. Tiny Soprano*

            This never really happened at one of my old jobs (where I was the sole receptionist at the main office for an engineering firm and my manager was about as effective as a tomato with googly eyes), so I took it upon myself to update EVERYTHING. How-to’s on every aspect of the job. Updated lists of vendors, contacts, who dealt with what, the lot. It came in handy because I ended up having to suddenly take a month off for glandular. I would love to say that they learned about the value of cross-training and having enough staff to properly cover admin after that, but alas…
            Tl;dr, I 100% agree. It’s a smart business move to know you have emergency coverage.

      2. Meep*

        I know someone like this. She would constantly make me feel like I was on the brink of being fired for minor mistakes – be it mine or hers. Safe to say I am now being treated for PTSD. OP is the worst.

      3. fhqwhgads*

        I think that’s reading a bit much into it. I took it more like, normally if an employee said “btw I’m taking a month off unpaid, see ya”, the manager would be all “wait, what? that’s not a normal thing to just announce”. And it’s not a normal thing to just announce because most people might wonder if they’d be fired for doing that. But OP feels like this person has no concern about being fired because she doesn’t only not need this job, but she doesn’t need any job. That’s what I think they mean by “leverage”, they’ll never get her to stop doing a thing by saying “we’d need to let you go if this continues” because her immediate response very well might be “ok, bye then”. To part ways may actually be what’s best for both, depending on what the “thing” is, but they probably feel icky that any minor thing you could normally just tell someone “hey stop” and they would, with this person feels like it’s suddenly amped up to possibly parting ways over.

        1. Gene*

          Yeah I agree that OP’s wording was unfortunate, and I can see laughing at the “I have no leverage to exploit my employee!” thing, but I can see it being an issue if she did just suddenly announce a month-long leave with not enough lead-time to figure out how to cover her. Doing shit like that can create a lot of stress for your coworkers (or in this case, the one other employee) who weren’t necessarily planning to have to work overtime covering you for an entire month. It’s unclear from the letter though if this was a super sudden announcement or if she gave them enough time to plan.

    2. SheLooksFamiliar*

      Agreed. OP’s comment of ‘I feel that we have no leverage over her at all,’ really bothered me, and sounds manipulative or, at least, a power stance.

      1. AnonEMoose*

        Right? I immediately thought of the person on Fox News who recently suggested stopping unemployment benefits so that people would be forced to go to back to work under whatever conditions, and compared it to the way military dogs are only fed at night, because “a hungry dog is an obedient dog.” Absolutely nauseating.

      2. Amaranth*

        I read it more that OP feels like they have no way to manage Jean because there is a perceived power imbalance in Jean’s favor. I’m curious though, since this is Jean’s first job and OP is treating her like a unicorn, she might think OP’s accommodation is normal. OP could also look at this month as an opportunity to have other team members pick up Jean’s work, reach out to clients who might never talk to anybody else, and even trying out a graphic designer or two for small jobs. If they keep giving Jean all the work, then of course they’ll have trouble if she ups and leaves.

      3. Allison*

        Right, I don’t like the idea that people will only do their jobs well, and follow the rules, because they’re afraid of the food and/or housing insecurity they’d face if they were suddenly fired.

      4. MassMatt*

        Yeah, I don’t want to pile on the LW, but the notion that you need to have “leverage” over an employee in order to manage them makes me think of, serfdom, sharecropping, indentured servitude, and company stores in mining towns. All those employees are highly leveraged, no doubt, but it’s not an employment model we should be striving for.

        TBy the LW’s own admission, the person they’re complaining about does a great job, and would take two people to replace her. Sounds terrible! OK, she announces she will be taking a month off (unpaid). You can fire her, but you say that would greatly damage the business. I guess if her flexibility really bothers you, you can start looking for replacements, with no guarantee they will do as good a job as she does.

    3. Czhorat*

      That was my initial thought as well, but .. I kinda see the point in the example given.

      Most employees wouldn’t just *declare* that they were taking a month unpaid leave. That’s a lot of time, might impact the business, and should be a request. It feels as if there’s a power imbalance in favor of the employee. I totally understand that the power imbalances usually go the other way, but that doesn’t mean it isn’t at all problematic.

      It might be frustration and slightly poor wording, IMHO.

      1. Nesprin*

        Meh, a friend once declared he was going to take 3 mos off to go backpacking. And his company recognized that outstanding electrical engineers were incredibly rare on the ground and gave him the leave. He’s now been working at that company for the better part of a decade, because keeping good employees with rare skillsets happy is a smart management decision.

        It sounds like OP has 3 problems: 1st, Jean is the only one who can do thing X, 2nd Jean occasionally takes long leave and 3rd OP has some resentment to the fact that she doesn’t have Jean over a barrel. Problem 1 is potentially fixable by crosstraining. Problem 3 is fixable by realizing that if Jean really does walk on water, giving Jean leave is cheaper than finding Jean’s replacement. Problem 2 is fixable by rephrasing Jean’s leave/flexibility as part of her non $ compensation.

        1. allathian*

          Yeah, that’s fair. It still doesn’t address the last problem, namely the effect on the morale of other employees. To be fair, that’s probably more of an issue for me, because in my working environment, it’s illegal, or at least breaches our collective agreements, to offer one employee better benefits than another person in the same position and with the same seniority. Things like the number of vacation days and base pay normally leave very little if not zero room for negotiation. I have more vacation days than my manager, because I’ve been working for the public sector for longer than she has. Performance bonuses are a different matter, and are in practice one of the few ways employers can reward people who’ve gone above and beyond.

      2. BRR*

        I can give the LW some benefit of the doubt on wording because I can understand how one might feel it’s difficult to be a manager in the situation. But it sounds like the business is actually lucky to have Jean and it sounds like they wish they were entitled to Jean instead of lucky. If Jean has irreplaceable institutional knowledge, is beloved by clients, and would take two people to replace; I’m going to make a strong guess that Jean’s position is underpaid. And therefore the business is lucky that Jean doesn’t need to work for the money because otherwise Jean probably would be looking for a new job.

      3. Gaggle*

        We’ve hired several new employees recently who previously were in retail or restaurants who *informed* us that they would be out of town xyz dates and would not be working. With our employees, it’s definitely been a case of they’re not familiar with the norms of working in an office AND they tend to know that we’ll try to accommodate because of recent turnover. I imagine that Jean is basically the same: she’s not familiar with the norms, she knows she is a valued employee that they want to keep, and it’s not the end of the world if this ends up being a dealbreaker for her employer.

        1. Zudz*

          Informing my employer when I will not be working seems like the appropriate way to make use of PTO.

          1. PollyQ*

            Disagree. Many jobs require a certain number of people working on any given day, or have periods where it needs to be “all hands on deck.” It’s entirely normal IME to need to clear specific days to be taken as PTO.

            1. Frank*

              A lot of the reactions here – as well as in the letter – seem to be that Jean isn’t performing the ritual of deference to her employer that the manager feels entitled to seeing from her.

              In reality, most employees should have the autonomy to “declare” their intentions for time off (with appropriate notice, of course). It’s your time; you earned it; you should be able to use it at your discretion. Employers can anticipate crunch periods where time off can’t be accommodated and let employees know those dates in advance – but outside that, approval should be a formality. There should be zero attitude and resentment around this. The norm of having to ask permission to use your own time when you need it is infantilizing, and many in the U.S. don’t notice unless they become self-employed and get to experience making their own schedule.

              1. Jess*

                This has been a slow dawning for me over the last year and a half as I transitioned to self-employed consulting. I just inform my clients when I won’t be available. I structure my own days. Interviews have also begun to feel less fraught as I frame them as “what I can offer you” rather than “please please hire me”.

                It’s been a major shift, and a positive one. I own my time, and I sell some to my clients.

              2. California Dreamin’*

                This is different, though. She announced she was taking unpaid leave. That’s not the same as taking your own PTO that you earn and have every right to take. I’m not sure you’re entitled to just decide you’ll be taking extra time outside that. I’m self-employed and can completely decide when and how much I work in a year. My husband as an employee can’t just say he’ll be taking all of August off and expect his employer to necessarily accommodate that.

              3. Not So NewReader*

                What about deference to the needs of a business that provides people with income for food and shelter?

                OP, how does her time off mesh with the business needs? Is this your IN-season and she flies the coop for a month? I don’t see anything wrong with asking her to check with the business needs before asking for large chunks of time. I am concerned that you feel so held hostage to this person that you can’t ask.

              4. allathian*

                Yes, I agree with you. Granted, I’m not in the US, so much of the discussion doesn’t really apply. By US standards I get a lot of time off. My manager expects me to respect our crunch periods by not taking a vacation then, but I’m not expected to work if I’m sick even if there is a crunch period. Other than that, I’m expected to plan my vacation periods with my close coworker (we cover for each other) so that we aren’t taking the same days off, unless the one who’s supposed to be working needs sick leave. If that happens, it’s the responsibility of our manager to either organize some sort of coverage (by outsourcing our job) for the most urgent tasks in our queue, and by informing other customers that they’ll have to wait. I’ve never been recalled from vacation because my coworker’s been sick, although my manager has the right to do that. It’s one of the reasons why some people who’ve been recalled from vacation once too often always want to travel internationally during their vacations, given that they’re much less likely to be recalled because the employer would be required to reimburse any extra costs incurred by rescheduling the return.

                That said, it’s one thing to expect that earned vacation days can be used more or less at one’s own discretion, completely another to expect to be granted unpaid leave just because you want it.

              5. RebelwithMouseyHair*

                In France, we have minimum five weeks paid leave, at least one of which is to be taken during the winter months. Employees must be allowed to take at least two weeks off in one block if they want. The employer is not allowed to prevent employees from taking their five weeks off, but has the last word as to when they take it off.
                So you do sometimes get silly situations like that of an accountant I worked with: her boss refused to let her go skiing in February, because he wanted that time off, then she still had two weeks owing in May, that needed to be used up by the end of May. What with there being at least three public holidays in May, she managed to eke her two weeks out into nearly three. May being the busiest month of the year, the boss was not pleased, but he had to let her take her leave then.

        2. Grown-Arsed Adult*

          I’m with Zudz. If I have previous engagements scheduled when I am hired, my first move is going to be to inform you that I will be using my PTO on those dates, so you/we can make plans to address that. If I’ve got training, trips or medical issues planned out that far in advance that I feel the need to inform you of (rather than simply just rescheduling, chances are good those are either non-negotiable or difficult/impossible-to-reschedule dates (tickets purchased, fees paid, appts made, other parties traveling/taking time off at the same time to be together, etc.) It’s something I’ve done before with few to no issues, most amounting to, “that’s going to be a bit of a crunch time due to the Chocolate Tea Pot launch date, so we’ll need you to be checking in/available to take meetings while you’re gone to handle x, y, and z”, or “since that falls during our big sale, we’ll need you to train another employee to handle your critical tasks, and we’ll want you to make up the hours when you get back.” I don’t think I’ve ever had a leave issue come up we weren’t able to figure out a way to handle.

          If you feel that allowing your employees to behave like adults who have the right (and the responsibility) to prioritize existing appointments, commitments, and claims on their time/money that they had before they even met you goes against your workplace norms, and that you felt you had to “allow it” in those instances because of recent turnover, the reasons behind the turnover that are your problem. Not your new hires.

          1. doreen*

            I’m not sure if you’re talking about informing your new employer of your previous engagements during the interview process ( which is really more of a negotiation) or informing them of these commitments weeks or months after your started the job. It’s one thing to say it during the interview process , where if the timing or amount of time of just doesn’t work for the employer they can adjust your start date or tell you that taking that time off isn’t possible or just not offer your the job. It’s entirely different to start a job in May without mentioning any pre-planned time off and then announce in June that you will be out the second week of July. I think Gaggle was talking about the latter example, although I could easily be wrong.

            1. allathian*

              I agree with you, although I’d bring that up during the offer stage, like I would any other accommodation request. That is, if I really wanted the job. If I’m approached by a recruiter and only apply to keep my interviewing skills sharp, I might bring it up earlier if I’m not really looking to change jobs.

        3. feral fairy*

          I’ve worked in retail & restaurants and I have never been able to just announce that I will be away for certain days. Within the service industry it is a widespread practice that you have to request time off pretty far in advance and that there are certain periods of time where no one can have time off like during the holidays. I wouldn’t assume that this is because they worked in retail/restaurants. It kind of sounds like you need to be clearer about the policies of requesting days off and securing coverage. Whenever I’ve started a new job this has been part of the orientation.

    4. TimeTravlR*

      That really set the tone for this letter, didn’t it? Alison did such a great job in her response though! So diplomatic!

    5. PT*

      I don’t know though. We had this problem at a place I worked with very low-performing employees that was short-staffed. Some of them very much took the attitude “we’re short staffed so you can’t do anything to me.” They were mostly part-time entry level employees, but they did require a week of training before their first day of actual work, and they knew that onboarding a replacement wasn’t super easy. So the ones who wanted to be jerks, were in a game of chicken with management where they would do as little of their job as possible knowing that we were between a rock and a hard place in our ability to replace them.

      Without the leverage of being able to go through the corrective action procedures that HR proscribed (verbal, written, 3 written warnings were termination) it was really hard to corral them into doing their jobs.

      1. The_artist_formerly_known_as_Anon-2*

        Progressive discipline can also backfire when it’s carried out on a GOOD performer. He/she throws up his or her hands and says “I don’t need this s**t!” and responds by walking out.

        1. Analytical Tree Hugger*

          Genuine question: If they’re a good performer, why would they be in the disciplinary process?

          The only scenario I can come up with is poor management (i.e., not recognizing a good performer and dinging them on stuff that doesn’t matter). Good performance isn’t just about output, so a good performer shouldn’t need to be disciplined.

          1. The_artist_formerly_known_as_Anon-2*

            “Genuine question: If they’re a good performer, why would they be in the disciplinary process?”

            Genuine answers –

            1) As you said, poor management.

            2) Often, a manager is concerned about a “prime performer” , getting, to use an old expression – too “uppity” about his/her position and has to be “put in his place”. In other words, doing this to your top performer sends the message out to others ….

            3) A manager may also fear for his/her OWN position – Mr/Ms. Good Performer may excel so much that “Bad Manager” becomes vulnerable.

            4) Economics. The best performers generally (but not always) are paid at the top of the scale. Driving your best talent out the door does cut the efficiency of your organization, but it does save you money (usually). And it may lead to increased head count .

            It usually backfires on a bad manager. The best employees often don’t put up with such s**t and bolt.

            1. quagmire*

              I remember at my last job, our raises were based on like a point system for our reviews. They didn’t want to give anyone the highest raise, so they spent the entire review telling me that I spent too much time “off task” and I needed to be more focused like my coworkers.

              Except they also had to admit in another section of the review, based on actual metrics, that not only did I exceed the expected output for the department, I was doing twice more than the next most productive person, with the same rate of errors.

              So I goof off too much and should be more like my coworkers, and that’s why I don’t deserve a fair raise, but also I’m working harder than anyone else in the department? Guess who managed to immediately stop goofing off AND also stop trying.

    6. generic_username*

      I’m choosing to read this as if it was poorly worded. Salary is a bargaining chip for employers (offer more so you can attract better people) in managing an employee and it generally is the most powerful one they have. Because Jean doesn’t need the money, suddenly that bargaining chip isn’t effective and LW doesn’t know what other bargaining chips they have.

      1. AnonEMoose*

        Maybe…but with people seriously advocating, unashamedly and in public, that if we let people go hungry they’ll be obedient workers…it feels pretty gross.

        1. generic_username*

          Fully agree that this is gross. I don’t watch Fox News and hadn’t seen that comment before writing my comment. I’m hoping that LW wasn’t thinking of it in that way.

          Also, not to digress, but the idea that people only work for money is such BS and fuels the mindset that we need to diminish or remove unemployment income and welfare options to spur people into work. Plenty of evidence exists that people with bigger social safety nets are actually more productive/better employees because they can be motivated intrinsically instead of being motivated by the desire not to starve or become unhoused.

          1. AnonEMoose*

            Full disclosure: I don’t watch Fox either, but saw the clip from a current events YouTuber that I do watch fairly regularly.

            And agreed on the idea that people only work for money…I’ve been in that position, and frankly, I did the bare minimum and hated it. I’m not at all surprised that people who…::gasp:: feel valued are more productive/better employees. I know I am!

          2. Koalafied*

            Agreed. I often think that we’d see a lot more people changing careers mid-way through their working years if we had a robust safety floor. The way it is now, entry level positions in most major cities do not pay living wages and have their lower ranks staffed mainly by disposable 20-somethings sharing a dilapidated loft with 3 roommates to squeak by. Once someone has clawed their way into a position that actually affords them an independent life or ability to start a family, going back to living in squalor with multiple roommates is typically off the table, which takes trying a new path off the table along with it. But I’m sure that a lot of people who are fed up or burned out or disillusioned with their current career would be willing to take a temporary pay cut if it the cut could be made up with belt-tightening around luxuries like streaming services and dining out at nice restaurants and buying front row concert tickets and the like, instead of blowing up their ability to house themselves.

          3. Mina, The Company Prom Queen*

            It’s funny because on the one hand, employees are supposed to act like money isn’t important, that they are working for the love of doing spreadsheets, TPS reports, or llama grooming, not because of money. But when that is actually true, the employer resents it and complains that they have no leverage over the employee.

        2. The_artist_formerly_known_as_Anon-2*

          Ah, you’re not familiar with late 19th-early 20th century industrialism. Read up on Frick, Bessemer, etc., how their labor practices would make anyone today want to throw up.

          Well, not everyone.

      2. Happy*

        Salary can still be an effective bargaining chip for people who don’t need the money. That’s the main way that businesses show whom they value, so increases in salary make people feel supported and valued even when they don’t need the money.

        1. Autumnheart*

          Seems to work pretty well when it’s executives being paid millions. I feel fairly certain that’s more money than those individuals “need”, and the justification is always “We need to pay those salaries in order to attract and retain talent”.

      3. Canadian Librarian #72*

        Salary isn’t a “bargaining chip”; it’s compensation for services rendered. WTF.

        1. generic_username*

          Salary amount is indeed a common bargaining chip. Particularly in salary negotiations. Or merit raises. Or bonuses. I think you’re misunderstanding my use of “bargaining chip” here. Other bargain chips in my mind: extra vacation time, free lunch, gym membership, flexible schedule, remote work opportunity, interesting work, corner office, etc…. Essentially, it’s what is in the boss’s toolbox to keep an employee at their company.
          LW may feel that no matter how much money he offers Jean to stay and work that month, she’ll leave if he says no to the month off (which is why the salary isn’t an effective bargaining chip – she’s literally bargaining away her salary for more time off). This is why Allison’s advice is spot on – he shouldn’t be treating this employee as any different from anyone else because everyone has a line in the sand and there’s no guarantee anyone will stay. If he is unable to give Jean that month off and she won’t work with him, then it isn’t a good fit for either of them. The problem for LW boils down to never even having that conversation for fear of Jean leaving

    7. Well...*

      I sometimes find it chilling how close many people’s sense of power dynamics between employer and employee is to slave labor.

      1. Gerry Keay*

        There’s a reason Marxists call working our current capitalist system “wage slavery.”

      2. Que Syrah Syrah*

        Admittedly, a small part of me is kind of relishing in this a bit. I think a LOT of employers would benefit from having the tables turned on them this way once or twice in their careers – where suddenly it’s the employee who’s holding all the cards instead of you, or at the very least holding the same amount of cards you are. It will help develop empathy – now you know what it feels like the vast majority of the time for the people under you.

        I know the traditional working dynamic is “you (the employee) must accommodate me,” but in reality, it doesn’t really always play out that way, especially when someone is selling their skills to you. Sometimes you’re going to get someone super valuable where you are going to lose some of your one-sided power over them, and it’s moments like that where it becomes clear that you’re not actually inherently entitled to be the one who holds all the cards just by virtue of being the employer. This is a business relationship and you’re trading things you both want with each other. Sometimes that’s going to be more egalitarian than what you’ve been taught to expect.

    8. Becca Rosselin-Metadi*

      Same-as soon as I saw “leverage”, I thought pay is not leverage. It’s paying the employee what they’re worth.

    9. NeutralJanet*

      I feel like this whole thread is jumping to the worst conclusion–even if you love your job and you have a great manager, you’ll sometimes have to do something unpleasant because it has to get done, and if OP gets the impression (rightly or wrongly) that Jean is only holding this job because it’s fun and she likes it, it’s a fair worry that she won’t do the parts of her job that she doesn’t want to do. For most of us, we work at least partially because we have to, so we do the unpleasant part of our jobs anyway; if Jean doesn’t have to work, then that motivation is gone. “Leverage” might not be the best word there, as it does imply something a bit unsavory, but the thought really isn’t that bad.

      1. AnonEMoose*

        Maybe. But that’s not what the OP said, and expressing it as “leverage” feels more than a bit unsavory. Wording issue? Possibly. But everything I’ve said is based on what the OP actually said, not on what she might have meant, and I feel like that’s fair.

      2. Tinker*

        I’d suggest that, actually, the thought is ultimately in fact that bad.

        A person whose lifestyle isn’t dependent on their job can still be motivated by satisfaction in doing a difficult yet necessary thing, the desire that an unpleasant thing be done, the desire to help people they like, the desire to enable the work that they do find fun, or the prospect of no longer being allowed to do the job that they enjoy. The missing piece of leverage if firing the person won’t wreck their life is not being able to wreck their life if they don’t obey you — and I’d say leaning on that, especially to the exclusion of focusing on those other motivations, is in fact properly viewed as unsavory.

      3. Nothing Rhymes With Purple*

        Other motivations to do the unpleasant part of one’s job:

        1) a feeling of responsibility. It has to be done so we do it.
        2) earning a feeling of accomplishment. even though it wasn’t fun we got it done!
        3) being an adult who knows that even pleasant things have unpleasant parts.

        Why should we assume that only managers and up are capable of these motivations and anyone below can only be motivated by the stick of penury?

        1. allathian*

          Yeah, that’s a pretty depressing view of humanity.
          Sure, if you’re living from paycheck to paycheck and constantly worried about losing your home or suffering from food insecurity, keeping your job under any conditions is probably pretty high on your list of priorities. But other than that, many people do get more out of working than just the paycheck.

      4. NeutralJanet*

        Plenty of managers write in saying that they have problem employees that they aren’t allowed to fire for political reasons, or because they don’t actually have the power to fire people, so the employee doesn’t have the impetus to improve. Is that significantly different from this situation? Of course, plenty of people have motivation to do the unpleasant parts of their jobs besides money–if Jean doesn’t actually need to work to survive, then she presumably has motivations other than money–but I also just don’t believe that none of you have work that you would be unwilling to do unless you were paid a lot to do them.

        1. Nothing Rhymes With Purple*

          Is that significantly different from this situation?

          Of course it is. Being prevented from being rid of a problem employee by external factors is very different from having an employee who cannot be caused emotional distress by the threat of being fired. LW can totally fire Jean, they just can’t bring her to despair and thus abject obedience by threatening to do so.

          Also, the threat of firing is not the only reason an employee would want to improve — it isn’t only business owners who are capable of wanting to do a good job. Guiding people only by stick with absolutely no carrot does not tend to produce lasting results or loyalty.

          I also just don’t believe that none of you have work that you would be unwilling to do unless you were paid a lot to do them.

          If our lived experiences don’t fit into the size of your imagination, that doesn’t make our lived experiences impossible.

        2. Tinker*

          A manager who has a problem employee they aren’t allowed to fire is indeed in a similar position to an employee who has a problem manager and can’t afford to quit, and I would say that both of these cases are undesirable. Hence, I think it’s good that LW isn’t actually prevented from firing Jane — they list reasons why they don’t want to, but there’s no indication that they actually cannot — and I think it’s good that Jane is able to quit if she finds the situation disagreeable.

          What LW is less free to do is to threaten to fire Jane in order to keep her in line but still be assured of keeping her around. I’m rather struggling for analogies to that situation that aren’t abusive relationships, possibly because, to be blunt, this is a description of the core power dynamic of an abusive relationship.

          As to your last point: I am, as it happens, trying to get out of a job in which I am miserable and not particularly useful — miserable in large part because I am not particularly useful, actually — and ‘leverage’ has indeed been a major obstacle to getting out — I haven’t felt like I could risk a change up until recently because I’m financially dependent on my income, I’m conscious of potentially being impacted by bias (I’m trans, for instance, and during some of the worst periods at this job I would have had to interview with any new companies as a visibly trans person who didn’t read consistently as any gender), and my confidence in my ability to do good work has been severely undermined by working for this company. So, yeah, you’re right, if it weren’t for leverage I would probably not be working here today. I don’t consider that a good outcome.

        3. JB*

          Yes, it is very different, because if Jean’s performance is that negatively impacted by her financial indepenence, LW can – in fact – fire and replace her.

          The fact that LW considers her ‘irreplacable’ indicates the position is likely way underpaid or otherwise not competitive, so the fact that they have someone of Jean’s level working in the position at all is because she IS financially independent.

          In other words, managers who can’t fire someone due to politics or lack of managerial powers have no recourse. LW has full recourse, they just recognize that Jean is already doing them a favor and they probably won’t be able to find anyone else willing to do the same.

      5. KingKatzen*

        If Jane isn’t doing parts of her job that she doesn’t want to do, then her manager has to decide if it’s worth it to keep her. As of now, they’ve decided she’s worth the trouble of her suddenly taking a month off. It’s basically what Allison talked about in her response.

      6. Well...*

        I extremely disagree with this. Of course most jobs have parts you don’t like, but that doesn’t mean one needs to be forced to do those parts under threat of impoverishment. You could do the parts you don’t like because you believe the final goal is worthwhile for other reasons (fulfilling mission, sense of accomplishment, making clients happy, whatever part of your job gives you a glow). There are so many hobbies that have unpleasant parts before the main goal (sports have drills, crafting has boring tasks, cooking has a lot of boring cutting, etc etc).

        I know in reality most people work to put food on the table. But I can’t get on board with the attitude that it HAS to be that way or nobody would ever work.

        1. Despachito*

          I see your point.

          However – if the main goal is something YOU want to achieve, the natural consequences of (not) wanting to do the boring parts are completely on you (if you do not do the drills, you will not be good at the sport, if you do not do the boring cutting, you will not get the food ready), so this is pretty clear cut (do nothing-get nothing).

          But if the main goal is something THE COMPANY wants to achieve, you are not inherently motivated to do the boring parts (as the goal is not yours), but they are still part and parcel of what needs to be done.

          I cannot imagine a cook refusing to cut vegetables because it is boring (assuming he is not Gordon Ramsay and has underlings to do that for him), and the employer not having any means to force him to do that (or fire him if he flatly refuses to do so).

  2. Dust Bunny*

    “she would have simply quit, and that would be disastrous for the business because of the institutional knowledge she holds and all our clients love her and always sing her praises. ”

    You are giving this woman way, way, too much power.

    I have a ton of institutional knowledge and my employer would 100% fire me if my attitude were that out of line.

    If the loss of one employee tanks your business, then you haven’t been managing the either the employee or the whole business well. If you have been running the business decently, then losing even a favorite employee won’t put you under and you can’t let fear of it prevent you from disciplining that person.

    So it’s time both to get a handle on your institutional knowledge and documentation, and on Jean as an employee.

    1. Alton Brown's Evil Twin*

      Good points.

      I think the owner doesn’t want to face up to the fact that the reason his business turns a profit is Jean.

      1. Dust Bunny*

        Or he thinks it’s Jean but it’s really not, and the business would weather the loss of her better than he thinks and he’s not giving his other, less-flashy staff enough credit. I can’t tell which it is, of course, but I’ve never seen a place that was even half-competently run done in by the loss of even its “best” employee.

          1. HungryLawyer*

            That’s the problem thought. OP doesn’t seem interested in having a balance of power, they seem to want an unreasonable amount of control over Jean. That’s why Alison suggested moving forward with an open conversation rather than a “you’re about to get fired” hardline approach.

            1. Czhorat*

              Yes, this. There is clearly an imbalance here.

              The solution should not be to create an imbalance in the other direction, but to come to some consensus on what does and doesn’t work. Was the month off problematic? IF so, that’s the conversation to have – that they can’t have her away for that long, but maybe two weeks? Maybe two weeks and two weeks remote-work at a lighter schedule? It depends.

              The other question is if the month really is an issue or if this is more a principle than actual issue. If so then yes, LW should probably reassess.

              Finally, it sounds like this employee is a “rock star”. High performers always get a little bit more leeway because, quite honestly, they’ve earned it with the value they bring to the business.

            2. Dust Bunny*

              I sort of get the feeling that the LW wants a lot of control (things done his way) but without too much responsibility (things done his way magically and without him having to be too involved), which is never going to work.

              If he’s too busy to be that involved, he needs either more or different staff. If he thought this business would sort of run on its own, then he doesn’t really want to be a business owner.

              1. Vlad, the Merry Impaler*

                True, but I didn’t read OP’s letter as that. Plus, Jean is a top-performer of sorts, and any half-decent manager knows that “treat employees equitably” is a far cry from “treat them equally”.

              2. Nesprin*

                Meh I can’t say I agree- if the expectation is you build 10 widgets a day for 10$ per hour, and you have an employee who can build 100 widgets a day, then it makes sense to try to hold on to them with higher salary or different perks.

            3. Not So NewReader*

              I did not read control issues so much as I read about someone who had given up too much control for waaay too long.

              Why does Jean have so much institutional learning that no one else has? What is happening that caused this end result?
              Why does OP believe they will lose customers if Jean leaves? No one else is nice? The customers won’t work with anyone else?

              OP, the rebuttal to Jean’s “I don’t need the money from this job” is, “But the rest of us do!!! And we need everyone here to totally and completely understand this concept”. As in if the business is not turning a profit, then there is no point to being in business.

              I can’t picture myself saying something like that at work, it’s so inappropriate to say. And to say it repeatedly boggles my brain. I’d have to say something, “Jean, we all know you do not need this paycheck. But the rest of us who work here actually do need the paycheck. I am going to ask you out of respect for the differences in people around here, that you stop saying that.”

              If Jean said that in other workplaces they would say, “Thanks for telling us, there’s the door, BYE!” Tricky part: It’s NOT because she does not need the money. Rather it’s because she thought it was okay to say that repeatedly. This is not much different than bragging about being rich or parallel ideas regarding one’s financial status.

              It could be that Jean has done a good job controlling OP. “I am going to make myself indispensable so you will have to put up with whatever idea I think of.”

              Bottomline is you have too much value all in one person. You need to find ways to spread out that value. It could be by expecting others to take on more or it could be that you need to hire more people. Most of the eggs are in one basket here and that is bad practice for any company.

        1. Smithy*

          For those who don’t do and/or don’t like the idea of external facing work – it certainly can seem like one person just happens to be uniquely charismatic and naturally gets what to do. But like so many other work streams, what to do can actually be quantified.

          It may be that since Jean does this work alone, there hasn’t been an obvious need or request to either share documents that track and show those quantified process. Or it can also be that the process Jean uses is more sui generis because she’s the only person who it matters to. Or a mix of the two.

          One thing that the OP knows is likely irreplaceable about Jean is that she can do a lot and isn’t necessarily demanding the compensation that others who have all of that skill/experience can do. Therefore, I think it’s really time to bite the bullet and hire another person to being supporting Jean on the tracking of processes/institutional knowledge.

        2. Martha*

          I’ve been the “best employee” who quit. It was fine. My boss was used to taking a lot of shortcuts and once I left he couldn’t do that. So he had to be a little more hands-on, but it was fine.

        3. what am I, a farmer?*

          Yep. I think small organizations and places without a lot of turnover are particularly vulnerable to this “oh no we literally can’t function without Bob” mentality. Eighteen months ago, I would have said there were 5 or 6 people at my job who were absolutely crucial for whatever reason — institutional knowledge or acumen, external prominence, leadership skill, etc. One of them literally started the company. Most of them have left since then, including the founder, and it’s… fine! There is really no job that only one person in the entire universe can do.

          1. can-relate*

            There is really no job that only one person in the entire universe can do.

            There are definitely limits to this: there are certainly very specific jobs that only one person can do to the best possible standard. Others can certainly attempt those roles, and will be able to do them, but only to a certain level. They may become as good at the role as the predecessor with time, but this can literally take years.

    2. Not Good with Names*

      “If the loss of one employee tanks your business, then you haven’t been managing the either the employee or the whole business well.”

      This 100%. No business can succeed if it relies so heavily on one customer or one employee.

        1. Not So NewReader*

          Maybe OP could sell it to Jean and/or her SO. Either retire on the proceeds or go start a Jean-free business.

          Yes that is a passive response. But the problem grew to this size in a passive environment.

      1. DANGER: Gumption Ahead*

        Seriously! What if Jean went on parental leave, had a medical condition that required months off, etc.? If that would tank the business then the problem isn’t Jean, it is poor contingency planning.

      2. allathian*

        To be fair, this business isn’t just small, it’s tiny. It’s just 5 people: the LW, their business partner, their wife who’s the accountant, Jean, and another employee. Sounds like Jean really needs to cross-train the other employee and possibly the business partner.

        It’s also possible that one reason why Jean is so popular with clients is her family’s wealth. She probably has networks she can use to get more business for the company.

        The smaller the business is, the greater the risk of the whole thing collapsing if one employee leaves, particularly without effective cross-training.

    3. Teapot Repair Technician*

      Even employees who aren’t wealthy sometimes resign or get sick. It doesn’t make sense to set up your business where one of those things happening would be “disastrous.”

      1. Rayray*


        I remember having a job where I took on many responsibilities, including many procedures which I along with management built up when we got new projects. I plead with them all the time to let me cross train others because it was incredibly stressful, frustrating, and upsetting to come back from a vacation or being ill and have mountains of work because “no one else knows how to do that and I’m too busy”

        I’m not saying this business relied on me slowly to get work done, but if I wasn’t there to do certain things then it could slow the chain of process down. It’s bad practice to have one person who is relied on so heavily cause you never know what can happen.

        1. The Rural Juror*

          Geez, I feel that. I feel like that person is me right now… but that’s because our profits took a huge hit during the pandemic and we haven’t been able to afford to replace an employee who moved away at the end of 2019 (we had posted the job opening in the beginning of March 2020 and then immediately pulled it when things went into lockdown). If I were to pull a Jean right now and announce I’m taking a month off, they’d probably let me do it! Even if were gone for a month and things weren’t getting done in that time, they probably wouldn’t want to risk losing the person who’s doing the job of 2 people…

          Man…maybe I will pull a Jean…

        2. ecnaseener*

          Yupppp. I got promoted right before COVID, my predecessor had left things in rough shape, I turned things around and made myself very valuable. And then I spent the first half of 2021 writing as much documentation as I could, so I could take a freaking vacation for the first time and get some coverage.

          Now would be a good time for OP to ask Jean to create documentation if she hasn’t already, so people can cover in her absence. I expect OP may be pleasantly surprised at how very possible it is to cover Jean’s core work with a little prep.

    4. JohannaCabal*

      Every company should be prepared for the unexpected. Whenever I hear about an employee who is “unfireable” due to institutional knowledge, I always wonder how their employer would react if said employee is then arrested the next day for some egregious crime, decides to join a monastery/convent, ups and moves to live in a van on a beach, wins the lottery, etc.

      1. Dust Bunny*

        We lost our head of IT (died very suddenly) and, while everyone was emotionally pretty upset, we functionally carried right on because everything else was in place.

      2. RabbitRabbit*

        A vet’s office that I go to had a binder labeled “If (longtime employee firstname) gets hit by a bus,” on a shelf that was visible from the customer side. I’m assuming it was the same thing, basically lots of SOPs and institutional knowledge in there. It got moved eventually but I assume was still in use. I also think that particular employee is no longer there.

        As someone who’s been that ‘indispensable’ person before – and tried to leave a ton of documentation before my escape – no one should be in a position where they are 100% indispensable. I know that this can feel scary to the employee, but in a functional, not-toxic workplace that should absolutely be normal and healthy. The OP needs to get institutional knowledge documented, needs people cross-trained whenever feasible. If Jean gets hit by a bus, you’re at least temporarily screwed.

        1. Person from the Resume*

          As a former military member, I am not uncomfortable with a maintaining a continuity binder because people move every 2-4 years. We all still had a job so secreting information wasn’t necessary for job security, but it shouldn’t be that way for civilians either. Everyone should have a continuity binder for when they leave.

          1. Drago Cucina*

            One of the best pieces of management advice was from the Army. Do your job so if you get hit by a bus the mission will continue. No secret knowledge.

            I’ve been fortunate enough to work for the love of the job. The paycheck shouldn’t be a stick, but a fair exchange between employer and employee.

        2. iantrovert*

          Yep. And documenting those things is a skill, and one that’s gotten me several interviews and promotions. I love documenting and, when possible, automating everything I can when I learn new tasks or areas of working. Business is growing and they need more people to do this job instead of asking me to do the work of four? Great, hello new coworker, here’s a high-level overview of what we’re doing, here are some training materials, and here’s my documentation of the processes and troubleshooting for when things go wrong. I don’t need to try to keep it all in my head, by documenting it I’m freeing up that RAM by committing that info to long-term external storage, and that allows me the capacity to delve deeper into new things. I sure as heck don’t want to be doing the same secret process for the rest of my career.

          Heck, at this point my team is maintaining and updating the documentation I created five years ago, and our most commonly requested process is largely automated so now it only takes twenty minutes instead of at least half a day–and it’s more accurate.

          I can go on vacation for several weeks and trust that if a new request comes in, they can handle it without needing to email or call me, and I did just that this spring when I bought a condo. Knowledge sharing is *freedom*. (And if I do somehow win the lottery (despite not playing, lol) and take time away from working, I won’t be that jerk who left everyone in the lurch.)

    5. My Brain Is Exploding*

      I don’t disagree, but I think that this is a common problem with very small businesses that only have a handful of employees.

      1. Mental Lentil*

        This is very, very true.

        But it’s also true that this places a greater onus on them to document this stuff. It isn’t that hard, but you have to commit to doing it.

        The first step is, of course, deciding what needs to be documented.

      2. emmelemm*

        Yeah, I work for a very small business, and we had a *very* key employee die suddenly, and we are surviving but it is still, a couple of years later, really, really difficult.

        1. Martha*

          There is a kind of insurance called Keyman Insurance. It covers losses incurred if you lose the person covered – the “key man”. If your business model requires you to rely heavily on a few people this insurance can be a lifesaver.

      3. twocents*

        Isn’t it kind of weird that the employee with the invaluable institutional knowledge isn’t the owner of the small business?

    6. Undisciplined Anonymous*

      I have never met a manager worth anything who thought about providing their feedback and guidance to another person as “disciplining.”

      Employment is an agreement between two parties, not an excuse to play power games. It does not sound like Jean is capriciously deciding to take this month off to hurt the business or just because she can. She has a very good reason for doing it. The OP should try to work with her to make the terms of employment agreeable to both parties.

      But just because there is an inherently unfair power dynamic at play between the vast majority of employers and employees is no reason to lose sight of the fact that employees are not slaves or children or pets. They have agency, and in cases where they can use it as they see fit without suffering, they should.

      1. AnonEMoose*

        This. “Disciplining” should be for serious issues, not for ordinary feedback or guidance.

      2. alienor*

        Honestly just finding out that my manager thought they were “disciplining” me would make me start planning my exit. I’m an adult with a professional job. We can discuss goals and expectations and hopefully come to an agreement, but at no time will I be scolded or punished like a child.

    7. turquoisecow*

      Absolutely. An old boss of mine was very big on cross training in case someone got hit by a bus or won the lottery. The secondary person doesn’t have to be as amazing as the primary, but they should at least have some understanding of how the sausage is made and extensive notes and documentation to follow. This is especially important in a small business where the loss of one person can be more devastating since it’s only one person doing the task, and often doing multiple important tasks.

    8. Worldwalker*

      “If the loss of one employee tanks your business….”

      Exactly. Because there are no guarantees in life. That employee — complete with client love and institutional knowledge — may have a heart attack at her desk tomorrow.

      There are, as Alison listed, innumerable reasons why any employee will not be with your business forever. You have to plan for that. If you don’t, you’re at the mercy of not just the employees, but Murphy.

    9. generic_username*

      I agree. I was this person at my former job, which was also a small family-owned company, and they managed to replace me (although I do still hear a lot about how much they miss me and how hard I was to replace, which is such an ego boost, lol). I remember feeling really guilty when I was leavings, but I just reminded myself that the business was successful before I started and would be successful after I left. No one is irreplaceable.

    10. EventPlannerGal*

      This, absolutely. I would be really surprised if OP’s fears here are actually accurate in any case; I feel like this is something that comes up a TON on here, the idea that if X person quits then everything will fall apart, all will be lost, yadda yadda, and it never ever seems to work out that way. Things might be slower to happen or you might need to ask a bunch of different people to piece together information, but things will get done.

      (Example: I was hired as the assistant to Alice. who had been doing the job for literally 20 years. People would make not-actually-jokes about how she could never be allowed to quit because she really ran the company, people would legitimately panic when they heard she was going on holiday, the response to any question would be “have you asked Alice?” etc etc. Irreplaceable. Well, Alice quit halfway through the pandemic and I have her job now, and it’s fine. The sky didn’t fall. Sometimes I have to Google stuff. That’s about it.)

    11. Catherine*

      Based on phrasing I’m not sure OP actually discussed with Jean whether she’d quit over this. “I realized she’d quit” is not the same as “she said she’d have quit.”

      It’s fully possible that OP is catastrophizing this in their own mind without a real risk of losing Jean.

  3. Roscoe*

    I agree with everything said.

    However, just as a person, there is something a bit… cold (not sure if that is the right word) about the idea that “well if clients love her, just find more people they’ll love”. As someone in a customer facing role, who gets a lot of praise because my clients really like me, it seems kind of like you are planning for my exit. And as an employer, I understand that one person can’t be everything and there always needs to be contingencies. As a person and employee, that just feels kind of crappy. Like, replacing a loved employee is a lot harder than finding someone good at graphic design, but I feel its kind of being looked at as interchangeable.

    1. Alton Brown's Evil Twin*

      I can see this go both ways.

      Yeah, you might see it as cold that they are trying to find someone as good with the customers as you are. But they might see it as you being possessive of the customers. They aren’t “your” clients, they are the company’s clients.

      1. KayDeeAye*

        Yes, and they’re clients and customers, not beloved friends. I think, Roscoe, that you’re taking this far too personally. The business should absolutely not be completely dependent on the belovedness (sp?) of one employee…and the employee’s value to the company shouldn’t be completely dependent on their belovedness among clients.

        I like to think that I’m pretty good at my job, and also that I’m good with the volunteers my non-profit depends on. But the organization needs to plan ahead for when I’m no longer around. That’s just a fact.

    2. Purt's Peas*

      I think it’s making the point that customer service, and getting along with customers, is a skill. Maybe it’s a rarer skill than graphic design, maybe it’s not. And it’s certainly a valuable skill. But she’s not inherently the only person that clients will love; you can hire someone who will have the skill to build those relationships.

    3. Naomi*

      As Heidi points out below, planning so that Jean isn’t the load-bearing employee is good for Jean, too. For example, if LW had someone else who could take over Jean’s tasks, it wouldn’t be such a big deal that she wants to take a long vacation.

      1. Rayray*

        Definitely been there. It really sucks when you have begged management to allow you to cross train someone on certain things and they act like you’re the unreasonable one. Coming back from a much needed vacation to seeing that absolutely nothing got done – even when you have busted your butt to cover for others on their vacations or for every dozens of times they stayed home with a sick kid….it’s incredibly upsetting. Makes for a super stressful return and just shows you that you aren’t valued the same way at all cause they just expect you to get it done. No regards to your needs at all.

        1. The Rural Juror*

          I have been there and it definitely sucks. I spent quite a bit of time laying out everything in a way that made it extremely easy for people to cover my time-sensitive tasks. Then I took a much-needed vacation! When I came back, none of the tasks had been done and I had to scramble. There was absolutely no point in making the effort ahead of time because no one ever bothered and the boss didn’t even check on it. It’s very frustrating and makes people get burnt out that much faster.

          1. FD*


            It’s so demoralizing to spend all that overtime getting ready, leave a easy, short list with clear descriptions, and then…nothing gets done.

        2. of course it's me*

          ack. I know this exact feeling. I took a super-short maternity leave (less than two months) from one of my jobs and, when I came back, I wished I had taken ZERO because I had so much work when I came back AND I still had a tiny infant . . .

    4. Colette*

      They may not be able to find someone the clients love – but they can certainly find someone who will be pleasant, do a good job for the customers, and build a relationship with the client. And I think sometimes people over-estimate how important being loved by the clients is. As a client, what I care about is whether you solve my problem, followed by whether you are pleasant about it. But if you can’t solve my problem, I don’t care how nice you are about it.

      1. NW Mossy*

        One of the most challenging people I’ve ever worked with is beloved by clients, so much so that they recently won an industry award for their customer service. Sadly, they’re of the belief that coworkers and their own leadership are only worthy of their scathing contempt.

        By design, clients only get a curated view of what someone is like as an employee. They’ll often be the very last to know if the employee’s behind-the-scenes behavior isn’t meeting the employer’s expectations.

      2. Koalafied*

        This is very true. There’s a consulting agency my department has worked with for more than a decade. About 8 years ago there was one junior/mid-level person assigned to our team whom we especially adored. As tends to happen with non-VP roles at agencies, she was only there for about 2 years before she moved on to something else. We absolutely missed her and there would often be comments made about how if she was still there we could farm a particular thing out to her that we know she would have been aces at, but with the current bench we’ll just do in house.

        Working with this person was such a pleasure, but she wasn’t the only or even the most important reason we stayed with the agency. Just like with coworkers – looking back, I regard the years when I had a close friend in the workplace as special times in my career, but I’ve never felt like having a close friend in the workplace is something I needed or would quit a job in pursuit of. The time we had that person on our team was an especially nice time I remember (at times wistfully), but it wasn’t the make-or-break factor in our ongoing relationship with her employer.

    5. DrunkAtAWedding*

      They are planning for your exit. Like Allison says in her reply, employers need to. What if, heaven forfend, you were injured or, happier scenario, offered a better job? What if they want to promote you? People are individuals but jobs can be filled by different people.

      1. Le Sigh*

        Yeah, that’s the thing. It isn’t any colder than if you take another job. How often do we read about people who put in their two weeks and then the boss freaks out? Ices them out, acts like it was a betrayal?

        You can be human, treat people well, value their skills, and still manage a business, dept., or team well. I was truly bummed when my last staffer left — she was great! So great, I wrote her a really strong recommendation. But she had a life to live and that’s okay with me. It doesn’t mean that I didn’t have things documented and managed for this very reason; it doesn’t mean once I had a sense she might leave, I didn’t start making tentative plans and thinking about how to rework the role if/when that point came.

      2. Koalafied*

        Exactly this. Yes, they are planning for your exit, as they should be for everyone’s. Having a plan for someone’s exit doesn’t mean you’re pushing them out the door before they’re ready to leave. It means you internalized well your scout training to Always Be Prepared.

      3. TiffIf*

        I recently accepted a different position at my current work. The new position will allow me to utilize the 8 years of experience I have with our product in a role that badly needs a SME in the capabilities of our product specifically.

        However, moving into that position will leave a gap in my current team as I am the product lead and have 3 direct reports. I have provided documentation and training on the responsibilities I will be handing over that the team is not familiar with (probably about 70% of what I do they were already familiar with even if it wasn’t them performing the duties). But I know that there will be some rough spots as they adjust. There is also the practical issue of we were already hiring because we are stretched thin and me leaving means the team will be stretched even thinner.

        Right now there is no one who can step into my role (which was a senior title)–2 of my 3 reports I could see having the potential to be the product lead, but are not right now good fits (nevermind the question of if they have interest in doing the people management part of the role). I have been working with them on how they can grow that potential, but that doesn’t happen in an instant. My manager, who most of the time would only have to step in on my product when there was a roadblock I couldn’t solve, will have to be more involved in the day to day work.

        One of my coworkers (senior peer) who encouraged me to go for my new position was talking to other people in the department and told me there were actually people who were like “but if TiffIf isn’t on that team, we’ll have problems!” and she straight up told them “That’s not fair to hold TiffIf back like that”

        I’m not trying to brag here, just trying to illustrate a point. If your entire workflow depends on one person you will have problems if for any reason they need to be absent. It isn’t fair to your business or your other employees and it isn’t fair to that person. Redundancy and cross training are important. There will be an adjustment period after a person leaves a position (or even takes a leave of absence, or just a vacation!) but how detrimental that whole process is is really dependent on if cross-training and documentation have been implemented.

    6. Worldwalker*

      The company *has* to be planning for your exit. You could be run over by a bus tomorrow. If they haven’t planned for what to do in that event, they’re in big trouble.

    7. Smithy*

      I was once the only fundraiser for a nonprofit with an Executive Director who did not heavily engage in any fundraising. Being well liked externally was an incredibly important aspect of my job and I also did hold a lot of information no one else really did at the organization.

      As uniquely special as I was to the organization while I worked there, it’s also very true that there are likely thousands and thousands of people around the world who do the same job I do. Not that I could be replaced by any one of them, but that we do a job that can be taught specialization. And so we do our best to uphold the legacy of the good work we did – in helping explain how we do our job. So if someone steps in while we’re sick or on vacation or during a transition period, we’ve done our best for that ongoing success.

      1. Le Sigh*

        +! And also — it’s actually considered important and good business practice to have succession planning in place (usually for key executive staff, but it just makes sense across the board). We’ve seen what can happen when a nonprofit or business relies too heavily on a specific leader and/or their personality — it can be really hard to move forward once they leave. My org actually makes it a point to have donors develop relationships with more than one person for this very reason — it’s ultimately about them feeling connected to the work/mission/org, not any one staffer (even if the staffer did great work building that relationship). That’s really important so that when any one person leaves, you don’t see a wave of donations/customers leave with them.

    8. Littorally*

      That’s taking it incredibly personally. Being loved by clients isn’t about being a person who is incredibly special and unique and wonderful to them. It’s about having really good customer service skills and being able to build rapport, which are absolutely standard employment skills that some people really excel in.

    9. JustKnope*

      You’re taking it personally when in fact, it isn’t! It’s business! They absolutely must be planning for your exit, just like they must be planning for their other employees to exit. I also want to gently point out that you’re saying your customer service skills and relationships are so much rarer and more valuable than being “good at graphic design” which is dismissive of other professionals with significant skills. It’s actually not a dime a dozen to find great graphic designers, just like it’s not a dime a dozen to find people like you with great customer service skills.

    10. what am I, a farmer?*

      I understand where you’re coming from, but I’d really encourage you to examine your beliefs a bit here. I got a lot of satisfaction and a sense of security of work out of making myself feel totally indispensable. I was told (and believed) frequently that they’d be lost without me, that I was so crucial, etc. It was a huge amount of pressure to put on myself. And it led me to stick out some situations that, frankly, I probably shouldn’t have stuck around for.

      We’ve had more turnover in the past year and now I know that when someone leaves — no matter how effective and important and beloved — people don’t sit around for months saying “oh no, if only Jane were here.” There’s an emotional goodbye and maybe a week or two of scrambling to fill the void, and then the company moves on, as it should. It’s ultimately freeing — and empowering — to know that no one is irreplaceable, including you.

  4. Amber Rose*

    “Your business plan can’t be “keep person X at all costs” because that will always, always fail at some point.”

    Gotta re-emphasize this. You cannot run a business around a single person with no backup plans. That’s just begging for disaster to strike. She’s already made it clear that she has other priorities in life than this job, which is as it SHOULD be, but also is notable because unlike many people she could choose at any moment that this job isn’t even on the list anymore and leave.

    1. cubone*

      It’s always fascinating to hear this again and again, almost as if it’s some unfortunate situation that’s been done to a business, like they had no hand in it. “Person X has so much institutional knowledge, now we can’t fire them”, well……. how did it get to that point? Who let them become such a source of said knowledge without making “document it” also a metric of their success? Or, who put them in the position that no one else on the team would also be part of gathering and holding that institutional knowledge?

      Of course there are folks who are a bit possessive of tasks/info, not good at documentation, but again…. don’t … let them get away with that?? I just always feel like there’s a perceived lack of agency on the manager’s side of these situations that is so rarely the case. It sucks if you’ve let it get to a point where someone holds so much they’re irreplaceable, but you have to accept and acknowledge that it isn’t sustainable and you as the manager have to take an active role in changing it.

      1. Your Local Password Resetter*

        It does feel like such situations weren’t managed properly, and now the manager is throwing up their hands and still not actually managing it.

      2. LisaNeedsBraces*

        This! Take responsibility. Usually, situations like this are due to mismanagement of the person with institutional knowledge, or the team as a whole. Along with not requiring Jean to document her knowledge, it seems that OP was complacent with the idea that “Jean will handle it.” Instead, wouldn’t it be great to say “Since the teapot project has two parts, I would like Janis to shadow Jean on the first half, and then run the second half with Jean’s supervision so two people are cross-trained on teapots.” Jean is in a senior position, so I imagine training is either already a part of her role or something she’d like to do.

        My hunch is that being a small business owner, OP managed Jean like this because the Jeans of the world are usually doing multiple job at once, so the company tries to save money by being understaffed and not hiring someone else. The other employee can’t be trained because they have so much on their plate too, so without hiring, it all just defaults as Jean’s responsibility. For example, instead of relying on Jean to do graphic design work (assuming that’s not her actual role), why not hire a graphic designer or get a contractor? Now if Jean leaves, the company loses multiple people (a graphic designer, copy writer, account manager, etc.). So why not start hiring for those roles?

        Luckily all of this within OP’s control and going forward, something they need to be on the lookout for. Cross-train people (which gives people skills and growth helps keep people in the company), document procedures and institutional knowledge, and don’t be afraid to hire and take things off of Jean’s plate. Honestly, that creates the kind of environment that retains people way more reliably than hoping your company is the only thing between your employee and destitution. In the meantime, if Jean is such an important employee, treat her like she is. Treat her like someone who has been doing multiple roles for you and not like an adversary. Work *with* her on her vacation request, while using this time for her to document and train someone else.

        1. RebelwithMouseyHair*

          Yes. I can’t help thinking that Jane flouncing off like this is also partly because she may be a little burnt out in this role. She may have found it very interesting because of the variety, but the time is coming to portion out some of her responsibilities elsewhere. She may indeed feel that OP is just always leaning on her instead of looking at the best way to do something: Jane can do the graphics so why bother hiring a professional graphic designer? Jane has always handled it, nobody has ever complained. Yet the layout of their documentation might look a bit messy or lack consistency because Jane is not a pro and doesn’t have time to make changes across the board when she decides to go for a slightly different shade of green on a particular document, and hiring a pro would definitely help get a sleeker look to everything. It’s just that very often a graphic designer’s improvements can be so subtle you don’t realise why it all looks sleek and smooth and very often the importance of their work is underestimated.

      3. Cthulhu's Librarian*

        To be fair, if someone is not really good with documentation, then simply insisting they do it may be worse than useless – information can end up scattered and haphazard and impossible to find and work with.

        The solution to this is not to throw your hands up in the air as a manager, however, but to partner that person with someone who is decent at documentation, and get it done anyways. Sometimes, yes, that means sitting down with the person yourself and helping them do it – and that actually is a useful way to spend your time, if it means you have useful documentation going forward.

    2. Gumby*

      Yes! My company is generally a good place to work, but there are several people who have rare skill sets and institutional knowledge who have decided that they just won’t do ThingA or ThingB any longer and it is a huge annoyance for some of the rest of us who just want to finish the project.

      We have legitimately been trying to hire a replacement for at least one of these people for… 2 years? and have not found one. It’s all above board as that is a ‘wants to retire’ person. But in the meantime, aaarrrggghhh.

      1. LDN Layabout*

        So essentially you have someone who’s only staying there because they know you can’t find a replacement for them and they’re simply unwilling to do certain tasks anymore?

        Because once more, this sounds like an issue with your organisation/management vs. the person in that position who’d be more than happy to retire.

        1. Gumby*

          I was **agreeing** that no company should have any specific person as a ‘single point of failure’ and acknowledging that by doing so, the company has put itself in a precarious position. The rest was an example of how that plays out; it was not meant as an indictment of the person in the position. Which people seem to have missed, but I don’t know how I could have been clearer.

      2. andy*

        Someone who wants to retire and is staying to do a favor for business is a bad guy, because they don’t want to do a job nobody else wants to do?

        1. Gumby*

          For the particular person I alluded to – I never said he was a bad guy. We are well aware of that he is essentially still working here as a favor which is why he is allowed to refuse to do things and not imperil his job. We appreciate his willingness to help us out. And, to be clear, I like him a lot as a person. Which I can do while simultaneously acknowledging that he makes my job harder. (In this case ThingA is “be in the same room with/talk directly to Patsy” when Patsy is heavily involved in some of the same projects. ThingB is “fill out the timecard the way you are supposed to”, ThingC is “train a replacement past a certain point”, ThingD is…)

      3. Figgie*

        My spouse is this person. He is only staying on until the end of the year to manage a huge company-wide project and he is very clear about the fact that he won’t be doing ThingA or ThingB any longer and if they don’t like it, he will retire effective immediately. The tasks they would like him to continue doing are repetitive, boring and his skill set is valuable enough that he doesn’t want to waste time doing those sorts of things at this point in his career.

        His immediate supervisor is having a hard time dealing with the fact that if he pushes my spouse too far in doing those sorts of task, my spouse will retire. Add in that my spouse has tried multiple times to get his boss to take seriously assigning someone else to do a ton of processes that will need to be taken over when he leaves only to find his boss doesn’t care. As my spouse says…I documented it all, I’ve pushed repeatedly for someone to be trained in these things and now I don’t care any more. I won’t be answering any phone calls after December 30th. :-)

      4. Cthulhu's Librarian*

        If you haven’t been able to hire a replacement for someone in two years (as in, you’ve never even made an offer to a candidate), you might want to consider engaging the services of a specialized headhunter to fill that position.

        Or looking for what you’re willing and able to train someone up to. A lot of times I see businesses waste years looking for someone who can hit the ground running with task X, when they could have trained someone new in that task in half the time.

        1. Autumnheart*

          Or maybe this position needs two new people. Or three. It takes a long time to build as much institutional knowledge to be able to handle multiple duties that each would be a job on its own, and sometimes the context behind that is that the person’s skills grew with the company/team/role during their long tenure.

          But you’re not hiring for the team Retiring Person started in, you’re hiring for the team RP is leaving. And that team sounds like it needs more than one person to replace RP.

    3. Thought Leader*

      You should always imagine that someone could be hit by a bus, need unplanned medical or bereavement leave, or win the lottery AT ANY MOMENT. If your business fails when one of those things happens, that is a problem.

      (Of course this is easier said than done! My start-up likes to be staffed lean so when one of my employees took 2 weeks bereavement leave and I freaked out (on my boss, not on my employee), that was a clear clue that we were actually understaffed and needed to hire…

      1. cubone*

        lol, so in my head, it’s very specifically any prep, documents, business continuity/handover stuff is called “The Lottery Bus plan”.

        I had been told by a great manager early on to always have a “if I get hit by a boss” binder or set of instructions. She called it the “bus plan”. Years later, I expressed this to a direct report, who said they’d learned the same thing from a past manager as well, but called it the “win the lottery” plan. Which is obviously a lot nicer and less morbid.

        It wasn’t an intentional decision, but from then on out we both referred to it as “The Lottery Bus Plan”. I’m not really sure if we meant it was EITHER you get hit by a buss OR win the lottery, or if the idea was a big ol’ lottery bus showed up one day to take you away (I like that idea most).

        All of this to say, I will forever refer to these preparations as “Lottery Bus Plans” and I would really love it to catch on. I think it’s perfect.

      2. The_artist_formerly_known_as_Anon-2*

        The concept is common – it’s called “risk assessment”. At one place where I worked, there was a confidential hidden plan = “If anon-2 leaves, offer him $x to stay and a promotion, if susieq leaves, we let her go and pass her duties off to billie and tony”, and so forth.

        As I’ve also said, many companies have “off budget slush funds” – to cover raises that have to be given out in emergencies, or promotions that the company dragged their feet on and management now faces “game time” (as they say in the NBA).

        1. The_artist_formerly_known_as_Anon-2*

          And he was still heavily involved in day-to-day operation of the Disney empire until his passing in late ’66.
          Disney World (then known as “The Florida Project”) was underway, under his supervision at the time of his death.

  5. Detective Amy Santiago*

    I speak from experience when I say – get that “institutional knowledge” documented ASAP.

    The keeper of ours in my department passed away six months ago. I’ve been asking for two years for more written documentation about various policies and processes and the response was always “ask [coworker]”.

    1. Heidi*

      Now is such a great time to do it too. She’s taking a month off, so she could spend the time up until then documenting the institutional knowledge so that they don’t have to bug her while she’s away.

      1. Seeking Second Childhood*

        Or vice-versa– anyting that owner and coworkers could not do without her? Hand her a list of the tasks t. Be done AND DOCUMENTED. And a list ofthe co-worker(s) to train on each task “so you can have another vacation some day without it getting crazy around here.”

    2. OyHiOh*

      In several different jobs I’ve held, one of the explicit lines in my job description was “document institutional knowledge.” The first time I did it, I was a teenage volunteer who’d been working in that setting for long enough that the volunteer coordinator asked me to update the training manual. That’s turned into 3 different adult roles where there was much institutional knowledge that had never been written down. Making and maintaining the “Oy gets hit by a bus” document/binder/spreadsheet is a piece of my work now.

      1. quill*

        Every job I’ve ever had has included “make SOP’s because we are SOL if the person who knows how to run the X ever has to go into surgery”

    3. kitryan*

      Sometimes there’s a bit of a catch 22 with that though. I am the only person who does 100% of my job. I’ve created a very thorough procedures document but it’s now 5 years old and outdated. I often try to circle back to revise but I’m constantly overworked and working OT just to keep up with urgent/immediate tasks. I’ve trained at least 6 people in various aspects of my job(s) over the years and they keep rotating them out of the dept just when they’re becoming useful. I would love to have *time* to create current documentation for my responsibilities but it’s surpassingly difficult to justify when I’m on a submission merry go round that I can’t get off of. Of course, if I magically *had* the documentation, then *everything* might be better because someone filling in could at least do many things by rote, following the manual, allowing me a bit of proper vacation time!

      1. Your Local Password Resetter*

        That sounds like a workload/prioritization issue more than anything. Management needs to make the documentation more of a priority or give you more resources and support. Right now you’re stuck in the classic pitfall where you’re too busy dealing with crises to deal with the underlying problems that keeps create those crises in the first place.

        1. kitryan*

          Yes, I agree – they brought in a 2nd person about 4 months ago and I struggle with effectively utilizing and training them so they *can* pick up some of the workload and we can get past the ‘urgent’ tier of work and make way on the lower priority stuff that still needs to happen, including documentation! There was an attempt to have someone else train her on some things but after the first month or so, it’s all back on me to keep her busy and trained on new things. And there really isn’t anyone else who knows these tasks.
          The fact that we’re both still 100% remote is not helping. I don’t want to go in the office but it would be loads easier to train her if she could do more shadowing and easier to give her tasks if I could see her progress…and it’s just hard to manage that with screenshares and phone calls, esp. when there’s all those balls to keep in the air in the first place.
          The positive sign is that I think they’re now 100% clear that it’s not a 1 person job and that they can’t move a 2nd person in and then out in 6 months, it’s got to be at least intended to be a long term gig.

        2. Koalafied*

          Agreed. It’s not on you, kitryan, if your employer gives you so much work that you can’t spend time on documentation. You are not responsible for magically finding extra hours to document your full-time work – documentation needs to be part of that full-time work, and if you don’t have time for it, you’re just as overworked as if you didn’t have time to do any other part of your job.

          Documentation is always the first thing to go when something needs to be cut, for good reason – it’s the least urgently needed thing you produce. But “worry about that tomorrow because today is bananas” is only a valid strategy when most days are not bananas.

          1. kitryan*

            100% correct- I’ve tried to make the point multiple times over the years that a system/staffing level that can cover only the most urgent 2/3 of the responsibilities is not long term sustainable, but the message has not been fully absorbed- or at least not acted upon. We’re now back to pre-pandemic staffing, 2 people, but the difficulties in getting the 2nd person up to speed while managing the workload, plus the fact that there’s no real acknowledgment that this is *really* a 2.5 or 3 person amount of work, as the business has ramped up over the years. That level of staffing would allow for no/low stress vacation and sick time to be taken, documentation to be kept updated, follow up on long term issues, reviewing procedures for improvement, all that good stuff.

            1. Koalafied*

              I really empathize. I spent years telling my bosses I was over capacity, that I had no time for documentation or to QA my work as closely as I really needed to be, and constantly negotiating deadlines or half-measures in response to requests from others, while underscoring to my bosses that there would be better options available to the people making the request if I wasn’t literally the one human person who was tasked with fulfilling all requests of that nature. They were always sympathetic, but there were like 5 more levels of management above my own boss that had to approve any budget for new hires, and whether it was because my bosses didn’t try hard enough or present a compelling enough case or whether it was because someone above them was stonewalling us, a new hire was always just around the corner but never materializing.

              Finally, my boss had to hire external consultants to come in and audit our operations, just so that they could back up their request for new headcount with an objective third party saying, “Your biggest problem is that everyone in this department is doing at least 2 jobs and Koalafied in particular is doing 3 or 4.” And even then it took another 2 years for the gears of bureaucracy to grind their way into an actual position being created.

              1. kitryan*

                Yup, this is basically it with slightly different details. IT support is a good comparison – it’s barely manageable to keep up with the ‘support tickets’ that everyone notices and really cares about but nearly impossible to keep up with infrastructure updates and process improvements that no one notices until it’s all too late and it’s a bigger issue. And as we lost staff but still managed to keep up with the tickets, no one other than me was too fussed that the long term stuff wasn’t getting seen to. It only changed when we were down to just me and I was very nearly ready to quit. That got us back to 2 people and managing the tickets, but still tough to impossible to ‘catch up’ on the other stuff. Because they forget that when I started, we had 2 full time people and 2 half time people and only 2/3 the workload.

  6. Lacey*

    The thing a lot of small businesses get wrong is that they’re set up so that if one of their employees leaves abruptly, everything falls apart. That’s always going to result in situations like this, whether the person needs the money or not.

    Most often it results in companies retaining awful employees who make everyone else miserable or just make the work harder. But, people leave, people get sick or die. Then what?

    I think AAM’s advice is spot on for how to fix this.

    1. Rayray*

      Sometimes too there are employees that simply will not let go of responsibilities or allow anyone else to take any of their load. We had a couple managers like that at an old job. These two women would also work insane hours, 10 hours was a short day for them and 14+ were usual. They were too insecure to let go of anything and didn’t trust anyone to do anything right. One of these managers also sabotaged me getting a sideways move to a better position. She didn’t like me because I had been hired to relieve some of the work that her elderly mother was doing. It was such a horrible place and there were way too many people, myself included that did hold a lot of knowledge on our positions but we weren’t allowed to cross train much. It went from a decent place to work to absolutely awful and a handful of us quit and a couple were unfairly fired within just a few months. No idea if they even learned from that.

      1. Captain dddd-cccc-ddWdd (ENTP)*

        employees that simply will not let go of responsibilities or allow anyone else to take any of their load

        In a functional environment if they can’t be persuaded to ‘let go’ this should be treated similarly to any other act of insubordination, which is what it boils down to.

      2. Lacey*

        Yup! I worked with someone who ran-off anyone hired to help her. She’s still doing it too. Meanwhile, the company gets bigger and bigger, ensuring a complete disaster whenever she finally does leave.

  7. BayCay*

    Totally loved AAM’s advice on this one. Most offices would be a better place if supervisors treated employees as if they had the option to resign tomorrow…because technically, most do. Everybody has a limit.

  8. Heidi*

    Love this answer so much. I think the OP perceives that Jean’s demands are the problem, but the actual problem is that the company’s functionality relies so much on a single person. Putting too much responsibility on a single employee is a setup for burnout – spreading out Jean’s responsibilities may ultimately allow her to keep doing the parts of the job she really likes and will motivate her to stay.

    1. Teapot Repair Technician*

      And Jean’s “demands” aren’t actually that unreasonable. A month of unpaid leave is something that a lot of employees will sometimes need or want for various reasons.

      1. Snow Globe*

        Wanting unpaid leave isn’t unreasonable. Telling your boss that you are taking unpaid leave next month with no discussion, is very unreasonable, IMO.

        1. Teapot Repair Technician*

          If she announced her leave with only a few weeks’ notice and refused to discuss it, that was unreasonable.

          The reasonable approach would have been to state her need for unpaid leave months in advance and discuss how to make sure things went smoothly in her absence.

          Based on the information in the post, I don’t know if Jean’s approach was reasonable or unreasonable.

          1. RebelwithMouseyHair*

            Yeah, I get the impression that she may be rather burnt out in her position and wants OP to sort out how to replace her on at least some stuff so that she doesn’t have to juggle quite as much. Her job can be interesting because it’s varied, but if some tasks are growing, they might need to be delegated to someone else.

        2. Minerva*

          I don’t know. If I really need the leave, I will resign effective the beginning date if I don’t get it. Letting my employer know its not negotiable isn’t unreasonable.

          1. Cthulhu's Librarian*

            So true – the employees position isn’t negotiable, it is fair to say that to your employer – “I will not work with John, he pushed me into traffic. You may either fire him and retain my services, or lose my services and retain his” is a fair statement, as is “No, my wedding is X date, and my honeymoon is Y days, and I will not work them” or “my graduation is Z day, I am going to it.”

            Never quite understood why employers would rather be left guessing about what is and isn’t negotiable.

        3. aebhel*

          I disagree. If it was a condition of her continued employment, which it sounds like it was, there’s no reason to present it as something that’s up for debate. Employers make non-negotiable demands of their employees all the time as a condition of employment; the implicit ‘I will quit if I am not allowed to take these dates off’ is no more unreasonable than the implicit ‘You will be fired if you aren’t at work on these dates’.

        4. Tinker*

          Is it less unreasonable to instead tell your boss that you are quitting entirely in two weeks?

        5. Not So NewReader*

          Telling your boss that you are taking unpaid leave next month with no discussion on a repeated basis, is only showing the boss how much they do not need you or reminding the boss that they need a better plan.

          Personally, I am not a big fan of Jean. She flaunts her money (“I don’t need this check”). She demands time off regardless of business needs. She’s not too concerned about how her cohorts will pick up her slack. When OP mentions something Jean said she seems to refer to herself often. I am just not a fan of Jean.

          1. Jennifer Strange*

            Telling your boss that you are taking unpaid leave next month with no discussion on a repeated basis

            There is no indication that there was no discussion or that this has been on a repeated basis.

            She flaunts her money (“I don’t need this check”). She demands time off regardless of business needs. She’s not too concerned about how her cohorts will pick up her slack.

            Again, none of this is in the letter. We know she has said she works because she loves the job, not because she needs the money. And there’s nothing to indicate that she demanded anything, just that the OP didn’t push back on her request because they were afraid she would quit. It’s not Jean’s fault that the OP chose to go that route. You seem to be projecting.

  9. Keymaster of Gozer (she/her)*

    Always, always, always plan for what you’d do if a member of staff was suddenly no longer available – whether it be due to being fired, quitting, getting in a severe car crash, leaving for the Vulcan Science Academy etc.

    Nobody is truly irreplaceable. Being held hostage by a staff member who is under the impression that they can do whatever they like is stressful as all heck, but there’s a lot of relief in adopting a ‘meh, whatever happens I’ll deal with it but they’ve gotta hold to the same rules as everyone else’ mentality. It was a weight off my mind I know that.

    (And our ‘irreplaceable’ person was eventually fired. By me. Advertised the job, now have a person who is actually *better* at it than the previous fellow, with none of the attitude)

    1. quill*

      You might have to hire two more officers to replace the one that went home to Vulcan, but honestly that’s what you get for allowing somebody to essentially do two jobs.

      1. Keymaster of Gozer (she/her)*

        Essentially I fired someone who thought they were Spock (but was way too emotional and illogical) and I now have a Data.

    2. Sara without an H*

      This. There should never be a single source of institutional knowledge in any organization. Anything more complicated than the daily mail run needs to be written down somewhere where other people can get to it.

      Aeons ago there was a university branch library (you’d recognize the name) where all purchasing and journal subscriptions were managed by two employees who happened to be sisters. They lived together and decided to retire together.

      And the branch manager discovered, too late, that they had kept all their records in their heads.

      Don’t do this.

      1. Keymaster of Gozer (she/her)*

        Former company I worked for, a very old one, discovered after a whole load of redundancies that a lot of the knowledge needed to run the place had been in people’s heads since the 1970s. That was a seriously messy time.

        (The railway is a really odd place to work sometimes)

    3. Not So NewReader*

      Annnd, there’s a thing called succession planning where you, OP, as the owner plan how you, yourself, will get out of the business.

      I have read a few books on entrepreneurship and owning a small business. What Alison is talking about here are entire chapters in these books.

  10. Snarkus Aurelius*

    OP, you’ve described Matt Lauer Syndrome – a term I just made up two seconds ago.

    When Matt Lauer was at the Today Show, he justified his multi-million dollar paycheck and job security by saying that if he left the show, everything would tank, people would lose jobs, the network would be in trouble, etc. NBC executives believed him. Although that wasn’t the only reason he got to stick around despite his rampant sexual misconduct, it was a pretty big one.

    Yet, when his behavior came out to the rest of the country and NBC had to get rid of him? The sky didn’t fall. The show didn’t end. The viewer numbers stayed the same. NBC still exists. The only person who lost their job was Matt Lauer.

    My point is that if only one person can do a job? That’s a problem, not an attribute, yet it’s rarely presented as the bad thing that it is. See the reasons that AAM mentioned, such as getting hit by a bus.

    I’ve worked with Matt Lauers – not the sex stuff, the myth that only THIS person can do THIS job so we have to make EVERY accomodation often at the cost of everyone else. I hated it. I was resentful and bitter. And I couldn’t say anything because my boss drank the Flavor-Aid.

    You know what? In 100% of those Matt Lauer Syndrome cases, nothing horrific ever happened when that person left. In fact, two weeks later, it’s as if the person was never there anyway because we picked up where that person left off seamlessly.

    So, you need to remedy this situation such that you’re not catering to Jean at the expense of everyone else. Should the day come when she wants to leave because she can’t take a month off? Cool! She can do that then, and you’ll be okay. (And you will! I promise.)

    1. Dust Bunny*

      I’m trying to think now of how many media corporations that didn’t vanish when their stars turned out to be creeps and had to be fired: Lauer, Charlie Rose, Garrison Keillor. All of them were pretty much media icons and exactly none of them ruined their respective networks when they had to be bounced.

    2. JohannaCabal*

      Yup, I’ve also seen executives and senior leaders keep toxic staff around to the firm’s detriment. Then, when they did leave, their replacement had to deal with a department mired in bad practices and pretty much had to retrain staff.

      1. cubone*

        This reminds me so much of an exec at my former, very toxic job. Our CEO would gush about how indispensable she was, promoted her multiple times til she was basically the right hand CEO. Staff would always talk about how well-respected she was in the industry, and how advantageous it was to have her because people worked with our org just to benefit from her knowledge.

        Thing is, she was not respected or liked in our industry at all. Our products, services, and brand were (which she had no hand in crafting, and was running very poorly, but luckily had some very talented folks below her who put up with it all). Somewhere along the line, staff and exec had conflated that because folks wanted to partner with us, and she was the exec largely responsible for partnerships, they wanted to partner with HER. She got media and presentation requests all the time, and it was the same thing – they wanted to hear about the organization, but because she held the role of “public facing person who does presentations/interviews”, it congealed into “we’re so lucky to have Executive, look at the demand for her to speak at conferences”.

        Related to the OP, I also remember sitting in a meeting with her where she bragged about how much institutional knowledge was in her head only and said “even if we tasked every staff with listening and transcribing everything I said for a whole month, we’d never get it all down on paper!”…. with a smile. Like that was an accomplishment somehow.

    3. The_artist_formerly_known_as_Anon-2*

      Matt Lauer could be replaced by another host, functionally.

      The TV/radio business, however, is ratings-driven and the people at NBC were concerned that if he had walked, especially to another network – and before his fall from grace, the ratings could go with him.

      With Lauer’s fall from grace, they had no choice but to replace him.

      They faced a crisis of sorts when Johnny Carson retired. Who was going to take over? They gave it to Leno, but Letterman bolted to CBS, splitting the audience. NBC never fully recovered from Carson’s retirement.

      Sometimes, some people are indispensible. I learned that in the late 1960s, when Bill Russell retired from the Boston Celtics.

    4. can-relate*

      I’ve worked with Matt Lauers – not the sex stuff, the myth that only THIS person can do THIS job so we have to make EVERY accomodation often at the cost of everyone else. I hated it. I was resentful and bitter. And I couldn’t say anything because my boss drank the Flavor-Aid.

      You know what? In 100% of those Matt Lauer Syndrome cases, nothing horrific ever happened when that person left. In fact, two weeks later, it’s as if the person was never there anyway because we picked up where that person left off seamlessly.

      I know what you mean, but I have actually seen the total reverse of this, multiple times. Power-hungry or otherwise awful managers abusing and gaslighting the employee who is genuinely the only person who can actually do a very important, very specific job, completely underestimating how difficult, or almost impossible, it will be to replace this person.

      Until it’s too late. And then, following that person’s departure (and, on a few occasions, these departures were illegal firings, which was even more baffling), the sky actually did fall. Projects unable to be completed on time (or at all), funding deeds cancelled, jobs lost, businesses closed.

      In every single case, the important employee in question was not a jerk at all, but was actually a lovely person and a good colleague. They were all also talented, and the bad bosses in question were always very clearly threatened by the person in question. The sole reason why the handover documentation didn’t exist was that the person in question was not given the time or resources required to produce it.

  11. AnonEMoose*

    Alison is spot on, OP. And I wonder if you know how unsettling your perspective of needing “leverage” over your employees is. You sound like you’re using the logic of the person on Fox News who recently suggested that the way to address the current shortages of workers in the service industry is to stop the additional unemployment benefits, and went on to state that military dogs are only fed at night because “a hungry dog is an obedient dog.”

    Yes, most people work because they need to. They need the paycheck. But good employers want people to find their jobs satisfying, or at least not dehumanizing. Because workers who enjoy their jobs, at least mostly, will be more productive and more inclined to go above and beyond, and that benefits an employer.

    The way to manage a person who doesn’t “need” the job is to treat them fairly, have clear expectations, and open communication. You need things from whoever is in that person’s role, whether or not they “need” the job. They get to decide if that’s something they can do. And both of you get to decide if your needs and what they’re willing to do are or are not in alignment. Don’t power trip yourself out of a good employee.

    1. Empress Matilda*

      Yeah, this didn’t sit right with me either. Good business relationships – good PEOPLE relationships – don’t rely on “leverage” to keep them going. They rely on things like mutual trust, respect, communication, equity…essentially, treating each other like human beings.

      Even in a workplace context, where there is a power imbalance between a manager and their employee, it still comes down to trust, respect, etc. The leverage is there, of course, but usually it’s the last thing on people’s minds. If you’re basing you’re entire relationship with this person on “she has to do what I say because…” – you’re not talking about a job at that point – you’re talking about indentured slavery.

  12. Anon and on an on*

    If another employee had “announced” s/he was taking a month off, what would you have said?
    What would you say to a different employee who tells you, “Yeah, I used all my vacation, but I need Friday off, so just don’t pay me.”
    If you are honest with yourself about your answer:
    “I would say no, because that’s not how vacation days work.”
    “I would say, yes, because it’s one day and it won’t impact the business.”
    “I would say, let’s discuss why you want this day and if it makes sense to let this happen.”
    Because right now, you’ve let one person do this. Even if you feel that you had no choice, you are the person in charge and you did allow her to stay home, keep her job and take unpaid time.
    When the next person comes to you with a similarly drastic request. “I need more days than I have, because.” or “I need to work from home, because.” or “I need to change my core hours, because.” are you going to listen and discuss it or say, “no, you can’t.” because you feel there is nothing the employee can do about it.
    Now is the time to reflect on that.

  13. UKgreen*

    What if Jean decided one day that no, she really did not need this job and just… walked out? What if Jean carried out an act so heinous that you had to fire her for gross misconduct on the spot? What if Jean got sick or was in an accident and had to take a month (or longer) off?

    Never, ever rely on one employee (and their skills and knowledge) being a single point of failure. You admit yourself that if Jean quit it would be ‘disastrous’ for the business. You presumably plan for other disasters – plan NOW for this one!

  14. Eldritch Office Worker*

    “I realized if I refused she would have simply quit”

    Do you know that for sure or were you just scared of that outcome? Did you have a conversation with her about it?

    Being held hostage by an employee is not a tenable situation, but there’s really nothing here to indicate she threatened to quit or would not have been open to a negotiation about making sure you were in good shape for her leave. If she didn’t she’s not even holding you hostage, you’re holding yourself hostage out of fear of what she might do. You can’t run your business that way. Have a conversation with Jean about expectations, priorities, documentation – things that will honestly make it easier for her to do things like take a month off if she wants. That’s a win-win, there’s no reason to assume she’ll fight you on it, and you’ll benefit from the added structure.

    1. Elenna*

      This. Jane presumably has reasons why she’s currently in this job, does OP actually know for a fact that those reasons were less strong than her desire to take a month off?

    2. Xavier Desmond*

      This is a great comment. Nothing in the letter suggests Jean is doing anything particularly egregious or is an unreasonable person. Talking to her and having an honest friendly discussion seems the best course of action to me.

      1. Empress Matilda*

        I was wondering about this as well. OP seems very concerned about leverage, but I’m not clear why it’s so important. Obviously we don’t have the whole context in this short letter, but from what’s there it doesn’t look like Jane is doing anything particularly awful. The month off is inconvenient of course, but is there anything problematic with her day-to-day work? Is she *actually* taking advantage of her financial situation, or is OP only worried that she *might* at some point?

        1. banoffee pie*

          Yeah, there’s no evidence Jean is holding everyone to ransom. It actually sounds to me as if the OP has got into the habit of thinking that employers should hold all the power, and if they don’t, it isn’t fair and the employee is ‘holding us hostage.’

      2. Simply the best*

        To be fair, if somebody in my office or any office I’ve ever worked in, just walked up to the boss and announced they were taking next month off for a non-medical or emergency reason, I think we’d all find that pretty out of touch and unreasonable. So I can understand why just that one act alone suggests some unreasonableness from Jean.

    3. generic_username*

      Agreed! I have worked with and known many people who don’t actually need their jobs for the money and almost all of them actually really want to keep their jobs. The idea that people only work for the money is silly (and constantly used as justification to cut welfare and unemployment, but I won’t get into that). It’s nice to be needed and productive! It’s entirely possible that LW could have negotiated this with Jean.

      Also, LW should be prepared for this to come up again. How long is Jean’s child’s holiday break? She’ll want that off, I’m sure. They really need to sit Jean down and come up with a solution that works for both of them, not just Jean.

  15. Akcipitrokulo*

    Answer is perfect – exactly the same as you would anyone else.

    Which makes me worried for the rest of LW’s employees! If the treatmemt of them is, even slightly, affected by a “well, they don’t have a choice…” attitude, it could be unpleasant.

    Treat all employees as if they don’t need you.

    Then you get a mutually beneficial business arrangement.

  16. KHB*

    She’s working for you because she loves the job – which probably means she cares about her work output and doesn’t want to see her (or her coworkers’) efforts go to waste. So think about using that as a motivating factor in your discussions with her. I.e., rather than saying “You can’t take a month off because I’m the boss and I say you can’t,” say “If you take a month off, that means more work for Lucinda and Wakeen, and it makes it really hard for us to bring the rice sculpture project you’ve been working on to completion.”

    (This is a good approach to use with employees other than Jane, too. Nobody likes to feel like they’re being arbitrarily ordered around with “because I said so”s, but people on a healthy team are usually happy to go along with a request if they understand the reason for it, even if it’s not what they would have preferred.)

  17. Donkey Hotey*

    No advice but plenty of empathy. Our company’s version of Jean had carved out a fiefdom 30 years previously, which no one noticed or cared until she moved 100 miles away and dropped to part time. And then started taking large amounts of unpaid time off, including multiple travel trips during the pandemic. She finally “retired” a few months ago and even with two months turnover time, there was a ton left hanging. Wish we could’ve read this a few months ago. I would’ve printed it and put it on our bosses’ desk.

    1. Anonymous Hippo*

      The noticing and caring is the problem, IMO. It looks like the Jean in your example gave a lot of signs that she was going to leave, and still nobody did anything. I see the same thing happening at my job, I’m in a Jean sort of position, and there are serious problems at my job, which I’ve taken all the way up the ladder, and basically been told “yes, it’s a serious problem but we aren’t going to do anything about it.” My boss knows I’ve been job searching on the side, and yet nothing is being done to document what I do, most of which is systems and procedures I’ve built up, so literally nobody else knows anything about them. I’m doing my best to document and cross train people on my own, but without any departmental support it is extremely hard to offload information all on your own, especially when much of the problem is related to a lack of staff to begin with. My boss whined “you’ll give me notice right” the last time he came across my job search, but there is no way in hell I could offload everything in two weeks, and he knows it. It’s extremely frustrating.

      1. FD*

        Same. I’ve said over and over that it’s a huge issue that we have no backup for my work, that no one else knows how to do what I do, and that I literally don’t have TIME to document what I do because I’m constantly overworked and drowning. So, they’re going to be up shit creek when I give notice (hopefully soon), but I don’t know what else I could have done, realistically.

    2. andy*

      It almost sounds like you are blaming you Jean, somehow, as if going part time or leaving the job was wrong?

      1. Donkey Hotey*

        Not blaming her for retiring. Blaming her for giving limited support to turn over her fiefdom to her replacement. Two months notice sounds good on paper, but then it took a month to find someone and then she took two weeks’ unpaid time off. That left two weeks, which meant four days (in office two days a week.)

        1. MadisonB*

          I obviously don’t know your situation, but, as I’ve read this thread, I’ve been repeatedly thinking that there are two types of Jeans: (1) Fiefdom Jeans, who seem to thrive on creating the perception of irreplaceability and unicorn-type institutional knowledge, usually with a hefty unwillingness to share knowledge; and (2) Drowning Jeans, who have highperformed into irreplaceability, institutional knowledge, and rewardless burnout territory that only comes with more work and more pressure (and usually stagnant pay…). I’ve worked with the Fiefdoms who wanted to see it all burn after they left (one of them machinated behind the scenes and managed to set it all on fire; five programs shut down), and I’ve worked with (and may be been) Drownings, who left and said “eff it” because no one listened and no one cared until the door was hitting them on the way out. It sucks all the way around.

          1. Donkey Hotey*

            That’s a whole different letter to Alison.
            Or a go-fund-me for her supervisor’s spine transplant.

  18. Butterfly Counter*

    I am not a person who runs a small business, so take this free advice for what it’s worth.

    Have you considered hiring someone part time (or maybe even full time) under Jean to at least document the institutional knowledge that Jean has? This could be beneficial in a couple of ways. 1) Jean won’t have the power of institutional knowledge disappearing with her, 2) You’ll have someone who at least has SOME knowledge to help out whenever Jean wants another month off or even quits, 3) You’ll already have hired one person to replace Jean who won’t need as much training as a person coming in cold, and then only need to hire one other person so that Jane’s job is entirely filled without as much disruption to the rest of the company.

    In any case, and has been commented on above, have someone get on that institutional knowledge so that’s it’s available to everyone as soon as possible. As someone currently struggling in volunteer work in dealing with the gaps in information that the previous person left with (and has little interest in being contacted about), the next person will no doubt be appreciative.

    1. Mental Lentil*

      A lot of small businesses work on pretty tight margins, but if LW has any capacity to do this, I highly second this advice. Get that stuff on paper! (Or better yet, in an online knowledge base.)

      1. Butterfly Counter*

        I thought of that, but also, if Jean is doing the work of 2 people, OP is going to need to hire at least one more person anyway if Jean leaves. And if OP can’t have a business without paying one person for the work of 2, that business is going to be untenable in the long run, anyway.

        1. Mental Lentil*

          There’s nothing in the original letter to suggest that Jean is doing the work of 2 people. She has a wide variety of skillsets, (LW describes her as “versatile”). It would take at least two people to fulfill those roles. For all we know, Jean could be doing actual work 20 hours a week and watching Mexican telenovelas on her phone the other 20, and still getting everything done that she needs to get done.

          I would rather have two part-timers carrying out different roles, rather than one full-time person carrying out both roles, because of the situation LW finds themselves in.

        2. Seeking Second Childhood*

          It would make a good part time job for a college senior who wants to work in your industry.

    2. Dasein9*

      Yeah, I’m reading the comments and wondering why Jean hasn’t already been asked to take on a protege or two as well. It sounds like she does really good work and the organization could use more of her. Clients who know Misha as “Jean’s close and highly-regarded colleague” who is now taking on clients of their own will feel cared for even if they can’t have Jean.

  19. Zephy*

    We would also probably have two hire two people to replace her, because she’s very versatile (graphic design, copywriting, strategy, account manager, etc).

    This jumped out at me. In addition to all of the other points about not making Jane the linchpin of your whole business, if she did need the money, you would be taking MAJOR advantage of her, like borderline-unethical levels of advantage, unless she’s making close to seven figures for doing what sounds like at least four different jobs.

    1. Mental Lentil*

      I’m not sure this is fair. I took “two people to replace her” as being more about skills than workload.

      If she’s only doing graphic design one day a week, and copywriting one day a week, and everything else in the remaining three days and she’s not overloaded, it’s not an issue. It’s only an issue if she’s doing the workload of two other full-time people (i.e., doing 80 hours of work in a 40-hour week).

      1. cubone*

        I think the point wasn’t that Jean is overworked, but that the specific combination of skills mentioned is highly rare and specific and should be compensated as such. It’s not “if Jean left, we’d need 2 people to complete her work in a typical work week”, it’s “if Jean left, we wouldn’t be able to find someone who could do the plethora of tasks attributed to her”.

        It’s this idea that if a person has a bunch of unique skillsets, you as the employer are getting a “bonus” of graphic design when you were looking for account management, instead of…. compensating the person appropriately for the increased value they bring to your business.

        1. Mental Lentil*

          No. If I need someone to do graphic design for 20 hours a week and I need another person to do accounts payable for 20 hours a week, and I somehow found a person who can do both roles in 40 hours a week, then they’re not bringing “increased value” to the business. It’s just that I have one person who can fulfill in 40 hours the work I anticipated needing two part-timers on board for. This is how I read it.

          If anything, there is actually decreased value and increased risk by putting two or more eggs in one basket, as this letter points out.

          1. MadisonB*

            A graphic designer makes different money than accounts payable than whatever Jean does. Right after college, I wore multiple hats at a small company, including IT infrastructure, HR, and intern supervision, in addition to my regular job (nowhere near any of those roles). My boss paid me $30K for my regular job and never paid me extra for the value of being able to handle IT and HR for her. I left, and she ended up having to pay an actual IT person $70K a year and then an HR/accounts payable person $40K a year in addition to the person she hired to replace my core role. She cut the intern program. For my boss, I saved her $110K a year in having to hire those other people to fulfill those roles and needs. I was a sucker, and my boss completely took advantage of that. So, yeah, I was one person who could fulfill 50 hours of work, but that doesn’t translate into market rates of what you’d paid other people to fulfill the niche roles.

    2. hbc*

      Honestly, I think the variety of skills needed is the closest thing to “leverage” that OP has. Jean doesn’t have to work, yet she’s doing a kick-butt job at a full-time gig because it offers her the flexibility she likely wouldn’t get elsewhere and the stimulation of wearing lots of hats. Sure, she’s not motivated by the paycheck, but I bet paycheck-motivated-Jean would have taken her awesomeness somewhere that paid better a long time ago.

      Neither is taking advantage of the other, it’s simply a trade-off. OP gets 22 person-months worth of work in a year out of a person she pays for 11 months, Jean gets the flexibility to drop everything for a month. Either one of them can decide they don’t like the terms anymore, but neither is acting unfairly.

    3. Maybe not*

      This is a bit absurd. An employee wearing many hats in a small business is normal. They don’t deserve $1 million for it.

    4. DANGER: Gumption Ahead*

      Eh, I was a “Jane” at a job just because I had picked up a really couple of weird skill-sets that usually don’t happen together that ended being useful in that position. When I moved on, they split my job into 3 different positions, but that wasn’t because I was being exploited, I was just experienced enough in all 3 niches to easily carry the load.

      1. Anon Y Mouse*

        Yeah. I work at a medium-size institution which tends to keep its staff a long time. Recently two moved on, with almost three decades of experience between them, and neither has been replaced yet because it’s a genuine question whether it’s fair to expect any new hire to do the full range of things they were doing. This is with quite a bit of warning that they were going to go. One of them was one of only two people who can cover for me, which is more than slightly concerning to me for all the reasons above.

    5. J.B.*

      I’m always skeptical when I hear that. There have been a few “critical” people I’ve worked with who were actually information hoarders and things improved after they left.

  20. Morning Reader*

    I’m enjoying the typo “bette offers.” Would that be Davis or Midler? Either way, I’m sure it would be an entertaining offer.

  21. Irish girl*

    My father’s company of 14 years is outsourcing his job. He has been doing it for 14 years and they added responsibilities and tasks that were not part of his original job but due to his prior experiences he was able to do.
    They are now expecting him to train the people to do his job on the bare minimum of what he did, not the other tasks, while still doing his job. There is 14 years of institutional knowledge that is going out the window and will likely cost them millions of dollars in fines if it fails.

    They still haven’t asked him to write anything up about all the tips and tricks and process that he used to do his job. He has tons of reports and analysis he asked his boss what to do with nd his boss said i never look at those so we dont need them… Well just cause his boss doesnt review them doesnt mean other people in the company dont. Just sad to see how messy the whole thing is due to their lack of planning.

    1. The_artist_formerly_known_as_Anon-2*

      Hey in the IS/IT world, there is an “outsourcing” trend – that’s been going on for 20 years… and … well… I could write an encyclopedia of “dinner table stories” on the topic.

    2. cncx*

      my job of ten years decided that my position wasn’t important enough to future plan for, and when i resigned, they decided the best solution would be to bring on a temp, because how hard can it be amirite… i hope i was as expendable as they thought i was. I know it’s not malice, it’s just exactly like you said: a serious lack of planning. I hope it works out for everyone.

  22. Cringing 24/7*

    It’s important to cross-train people and be sure you’re staffed to the point where you can handle someone being gone. What if she caught COVID and was in the hospital for a month? Do you have a back-up plan for how you’d handle her accounts/work/whatever then? If so, use that back-up plan while she’s gone for a month (and if not, then you need to develop a plan for when people are gone/unavailable, like Alison said).
    Looking at employees and thinking, “I don’t have enough leverage over you,” is… not great from a managerial standpoint. The employer/employee relationship is a mutually beneficial business relationship, *NOT* a dynamic where one party attempts to gain a leg-up on the other. Maybe it was just bad phrasing, but it came across as controlling and manipulative, and it should likely be something to reflect on if you meant what you said.

  23. Mrs B*

    If this is their first big “ask” (though the letter makes it sound like it wasn’t really an ask) and you would be willing to extend to the other employee if it came up, and you can make it work at the business why not? It may even be a good excuse to give the other employee a chance to shine or gain new experience. I’m feeling that if the reason was something they felt was more “worthy” like a family member going off to a tour of duty or something it wouldn’t be seen so negatively. Where I work we have an hourly employee who takes off for about a month at a time twice a year, and as long as we can make it work schedule-wise it is approved, aware that one day it may not be possible and they may quit or be let go as a result. People remark on it, but they’ve worked for us for over 35 years and it is unpaid and other PT’s get a minor boost in hours so it’s never been a huge source of resentment from what I can tell.

    1. Falling Diphthong*

      That’s a good point about the “worthiness” of the reason–like companies that want to evaluate if someone is really sick enough to need sick leave, or really close enough to take 5 days off to travel to a funeral. OP wants to be in a position to judge the worthiness and allow only worthy excuses, and employee is already in the position to say “If you won’t grant this, I’ll quit.”

  24. FD*

    Also, as a person who’s the Jean to my company, a lot of times, it SUCKS to be the Jean because you feel like you can’t take time off because there’s no one to back you up. You end up having to just work crazy hours before and after your vacation to keep up.

    Part of where you’re lucky is that you’ve got a person who can basically fill multiple jobs in one package. That’s useful while it lasts, but it can be an issue when your business is only profitable when you happen to have a person who can be both a graphic designer and an account manager. You’re not going to find that again most likely.

    You should start to figure out what services she provides and what you would do if she did leave. For instance, you likely need an account manager in house, but perhaps you could hire out the work of a graphic designer as needed.

    1. NerdyKris*

      I’m not the Jean but I did take over for someone with the “never document anything, it makes you less valuable” mindset, and it’s such a load off knowing that if I kick the bucket tomorrow anyone can pick up my job. This is the first job where I’ve actually felt needed, and my biggest source of anxiety is that I’ll be letting people down if I leave.

      1. Anon Y Mouse*

        Yep. I’m the only person who does my specialist role at my company. I’ve never been the only one before. Recently I took several days of leave, and although I knew I was officially OK not to check my inbox during that time, it was hard not to feel responsible nonetheless…

        I’d be much happier if there was a full procedural manual, and I am documenting with the hope of being able to knock out at least a skeleton one.

    2. Come On Mylene*

      I am the Jean in my organization as well, minus the wealth part. I have not taken a full week vacation in YEARS because of this. I begged my boss for help and he fluffed it off. I finally had to drop the ball in a way for him to notice, and he finally hired a part timer to take some responsibility off my shoulders. Job security is great, and burnout, not so much.

  25. Essess*

    During that month of unpaid leave, you hire another person and start training them to do her job. You should never have only 1 employee that can do a job duty. When she decides to come back from unpaid leave, you have the 2 of them share job duties (and adjust hours accordingly) so that the other person remains cross-trained so that Jane always has backup. You sit Jane down and explain what your professional expectations are. If she is not willing to treat the job professionally, then you need to do the same thing you would do to any other employee that isn’t meeting job expectations. Just taking a month off without warning isn’t doing the job. You should never have one employee that can hold the business hostage.

    1. katkat*

      Wow, harsh. She is not holding the business hostage. She is doing the job(s) she has been given and doing it well. That is not a sin. She asked for time off and her boss approved. Not a sin. Not a hostage situation.

    2. Aquawoman*

      Given that the LW identified no repercussions or problems that arose from her taking a month off, I don’t think you can say that she “isn’t doing the job.” If she’s worth two people, she’s done 22 months of work in the past year.

    3. NerdyKris*

      I think that might be unnecessarily adversarial. It doesn’t sound like Jane’s doing a bad job, LW is just worried that they can’t push back on any requests. They should start from a position of “what can we do to accommodate this” not “your job is on the line because of this one thing I said was okay to do despite your stellar work”. That’s like the person who wrote in after firing a top performer for asking off for her graduation. You don’t bring down the hammer when someone who is a valuable asset asks for too much, you work with them.

  26. Falling Diphthong*

    If your business relies on having one magical person who does the work of two people, that’s not sustainable.

    Amazing how many letters come down to this basic principle.

    1. The_artist_formerly_known_as_Anon-2*

      There was one letter a year or two back – a manager complained that his employee asked for help – because he was overloaded and burned out – and then finally just walked out.

      And the happy “followup” – they hired two people to take his job, and then also funneled off around a third of his work to four other people. THIS GUY WAS DOING THE WORK OF AT LEAST THREE PEOPLE, AND THEY WERE UPSET WHEN HE WALKED OUT WHEN THEY REFUSED HIM?


      1. Detective Amy Santiago*

        I got fired from a job because I couldn’t keep up with the workload, constantly asked for help and was denied/told I could work as much OT as I wanted, etc… they had to hire two people to replace me.

        1. kitryan*

          Yes, I’ve also been told that I could experience the wonders of working as much OT as I wanted.
          I don’t know why I wasn’t more excited by the prospect. I actually decided yesterday that I wasn’t going to work any OT this week, which will be one of 2 or 3 weeks with no OT in about a year. With how nice and relaxing it was having the whole evening yesterday, I’m starting to think that a lot of my energy and motivation issues are actually overwork/burnout issues.

  27. Lucious*

    Two problems. The OP is too reliant on Jean-this is a problem regardless of whether or not she needs the job. What happens if she’s hit with a family emergency and has to leave town for two weeks? Does the organization grind to a halt?

    Problem #2: this is a personal philosophy rather than a measurable business rule, but a manager who doesn’t value their people should find a different role. “Leverage” is not a word that belongs in discussions on motivating employees. Alas , the world is full of managers who are in the job for the title and could care less about doing it well.

    1. Eldritch Office Worker*

      As the adage goes, people don’t leave jobs they leave managers. A manager who thinks they have leverage over me – in other words a manager who basically thinks they’re blackmailing me into working for them – is a manager I’d leave.

  28. Boof*

    OP – whether or not Jane wants the salary, you’d be in the same situation if you feel you “can’t” fire them despite doing things that make working with them difficult. The question is not what leverage do you have over Jane, because in the end you have the ability to fire Jane if it’s not working out, just like any employee. The question is at what point would you fire Jane (or anyone) if there is some problem with them. It sounds like you do not like what Jane is doing but are not willing to fire yet, because employing Jane has a LOT of benefits. But you need a replacement plan for everyone, and if Jane’s doing the work of two people, consider giving Jane the commensurate benefit of double vacations or other flexibility ^-^ And consider doing the same for other employees that can demonstrate very high levels of performance; etc etc. But you do need to make sure you have a coverage plan for EVERYONE (what if someone gets ill? Has to take family leave? Decides to quit?) no matter what, and discuss with Jane that if you’re willing to be flexible, how much notice you need before an extended leave.

  29. katkat*

    I honestly think it’s little unsettling that you wished that your talented employee didnt have other options… I would hate to be that job.

    On top of other suggestions here i would really think about how i want good employes to view my business. This question makes you seem like a boss who is threathening to fire people on any argument or desagreenment. As Said before, good employes usually have several options and they choose the one that best suits their needs. Just as you choose the best employes for your company.

    1. Eldritch Office Worker*

      I agree. The answer to having talent isn’t “chain them here forever”, it’s “be an employer that can attract and retain impressive employees, treat them well, appreciate that they chose to work for you, and understand that things change and they might someday move on”

      ‘Treat them well’ doesn’t mean bend to their every whim so they never consider leaving, it means give them reasonable flexibility, compensation, and working conditions, hear their concerns, and provide regular constructive and especially positive feedback. If a month off isn’t reasonable flexibility, tell her that. But doing whatever she wants because you don’t want her to ever consider leaving, especially if it’s at the expense of your other employee (which it sounds like it might be – you’re a small team and someone has to pick up the slack) is not good management.

  30. Decidedly Me*

    You manage her the same as you manage anyone else. Not needing the job doesn’t make her more special than those that do need the job. You’re going to make a larger problem by continuing to allow her to feel like she can do whatever she wants. It’s bad for you, her, and others at the company.

    Definitely don’t let her (or anyone) hold all the knowledge – it’s a mess if something happens and so much can happen. All of my key folks are going on extended leave (fully approved and within policy), almost back to back to each other. We’ve been documenting everything because we hadn’t done as much as we should have prior to this and I’m so glad we did. We just moved another person into the same role of the first person that was going on leave. He had some time to train her, but also had to leave earlier than we expected and will be out longer than expected. It’s hard to tell the first person is as new as she is because she has that documentation to fall back on.

  31. Vlad, the Merry Impaler*

    Leaving aside – for now – the glaring management / business strategy landmines you planted yourself in your own backyard (maybe understandably, but lethal nonetheless) and sticking to the question at hand: 70%+ of employees are said to leave their manager, not the company. Beyond Alison’s solid advice, a fantastic, close-but-professional, warm personal relationship based on mutual respect, trust and work meaning works wonders sometimes. It might request from you a complete overhaul of your paradigm (the “leverage” bit is concerning from where I stand) but… a business owner *must* do that to ensure not simply survival, but success (see Google’s research on their own exceptional teams / managers, it’s free instruments and all).

    I had an employee who worked for fun once (not like that, he was a college student, wealthy family, he worked strictly to buy himself outrageously expensive sportswear – I kniw that because I had long 1-on-1s with him). This is how I motivated him, kept him and helped him advance.

  32. NerdyKris*

    I’ve found a good way to handle needing to write things down and document is to frame it as a favor to them. “If you get sick, or go on a long vacation, we need to be able to know how to do these things so we’re not calling you up in your hospital bed or on the beach.” Some people get that mindset that documenting things is so the company can fire them, but it’s not just the company that’s being helped. It also helps the employee to actually disconnect from work when they’re off.

  33. DG*

    Honestly – good for Jean. May all of us eventually reach a point where we’re financially secure enough to work because we want to and not because we feel indebted to an employer. May all of us have the option to occasionally ask for some extended time off (instead of a week or two here and there) for all kinds of personal needs, not just birth/severe illness/etc.

    I didn’t get the impression that Jean would have quit if she didn’t get that time off, but rather that she understands the capital she’s built at the company (by doing the jobs of multiple people!) and was willing to put some of that on the line to get the time she wanted with her family. That was a smart calculation on her part, not entitlement.

    1. Hiring Mgr*

      Mainly agree, but it sounds like Jean just kind of announced “hey I’m taking a month unpaid leave” . If it really went down like that with no prior notice, or asking if it could work, but just a statement, etc. then I understand why the OP is frustrated.

  34. The_artist_formerly_known_as_Anon-2*

    Ah, I saw this a lot in my computer career !!! And with the Dow Jones hovering at 35,000 today, 401Ks are explosive, portfolios immense.

    There are a lot of people working, that companies rely on – that don’t really need the paycheck any more. It’s also nice for an employee to have some leverage – some options.

    On the other hand it can be hell for that employee – if he/she is the only one familiar with a line of business. I think I discussed this in a prior thread – one of my responsibilties was managing a system that generated around ten percent of the company’s business. And I was desperately seeking a backup because I was becoming pigeonholed…

    The assginee who I was supposed to train refused to learn the system. And the manager I had was a bit weak, and would not enforce the rules. And then I planned a trip to Europe – with the company’s permission – in March , the trip to be in July. My vacation time was approved. So I paid for vacation expenses (car rental, flights, some hotels) and of course, Bozo wouldn’t learn the system.

    Comes early July – and I’m called into the office and asked to cancel the vacation. “We’re in a crisis” … YEAH OF YOUR OWN MAKING. I offered to cancel BUT the company was going to have to reimburse me for everything I shelled out, PLUS a third more to cover taxes, plus an extra week, before the summer’s out. “uhhh…ummm. uhhh…. gee whiz!”

    We had a good time, but my career was over in that place, anyway….

    This is just one “dinner table story”. I have several more in this same genre.

  35. Macaroni Penguine*

    Yeah, just treat Jane like any other employee and train others to have her skill set. The power imbalance inherent in the employment relationship is leverage enough.
    Also, thinking of salary as leverage on employees? Yikes. The concept troubles me on some visceral level. Sure, employment is an exchange of skills/labor for income/non financial benefits. But this transactional relationship should have a component of basic human decency.

    1. Autumnheart*

      Yeah. Salary isn’t leverage in any case, because when an employee gets a paycheck, it’s for work they already did. If a manager wants to threaten an employee’s future earnings if the employee doesn’t comply (seen often in retail/customer facing roles, employee doesn’t play ball and sees their hours get cut) then that almost inevitably results in losing that employee. I don’t think it ever results in an employee trying harder. A bad employee thinks, “I already don’t care that much, why would this make me care more?” and a good employee thinks, “I bust my butt here and this is what I get when *I* need something? Bye!” and finds a new job.

  36. Jennifer*

    Never make anyone irreplaceable. It sounds like the issue is you’ve given her too much power and she is a bit manipulative and willing to remind you of that when she doesn’t get what she wants. Start cross-training people and getting your clients comfortable with other people so she realizes she IS actually replaceable and you’ll be just fine if she leaves.

    I get that anyone can leave a job at any time but the way Jean is handling this is a bit rude. If I was requesting a month off, I’d definitely want to work with my boss and the other employees to make sure there was coverage.

    1. Boof*

      IDK I think it’s impossible to say from the letter if Jane is manipulative; seems like the company is getting a pretty sweet deal of of Jane based on what’s in this letter. I’d need to know a lot more like, how much vacation does Jane normally get, when Jane does get vacation is it actually vacation or is Jane peppered with work throughout their “vacation”, does Jane seem overworked; it’s possible this situation is more “jane is standing up for themselves and demanding what they need and have earned” rather than “jane arranged to be mission critical and now has started taking advantage of the position”

    2. Jennifer Strange*

      I get that anyone can leave a job at any time but the way Jean is handling this is a bit rude. If I was requesting a month off, I’d definitely want to work with my boss and the other employees to make sure there was coverage.

      There’s nothing to indicate that she doesn’t want to work with the boss to make sure there is coverage. It sounds like the OP is just granting her request with zero discussion. That’s not Jean’s fault.

      1. Jennifer*

        If she “announced” she was leaving instead of asking, that is partially her fault and a bit entitled.

        1. Jennifer Strange*

          My point is that OP could have pushed back and chose not to. If that’s the way OP always handles things for Jean she may be surprised to find out there was an issue at all.

  37. Alexis Rosay*

    My mother was this type of employee. She was financially and emotionally fine getting fired, so she was willing to speak up on issues other employees were too afraid to. Often it was basic stuff like complying with OSHA safety guidelines.

    All employees should be treated as if they have other options, but sometimes it takes someone who really does have other options to make managers understand that what they’re doing is not okay.

    1. The_artist_formerly_known_as_Anon-2*

      I used to carry a copy of the 13th Amendment in my wallet –

      “Neither slavery nor involuntary servitude, except as a punishment for crime whereof the party shall have been duly convicted, shall exist within the United States, or any place subject to their jurisdiction.”

  38. Bird Lady*

    Our 50 million dollar budget non-profit operates this way. We have to keep bringing back retired grand directors to work whenever someone quits. Which happens a lot, because of low pay, no raises, and the sense that the higher ups don’t think we deserve better. In my own role, I have several wildly different buckets of responsibilities, which I handle in my own unique way (since I was never properly trained) and have zero time to document. I am looking and weep for my replacement.

  39. DANGER: Gumption Ahead*

    First, let go of the whole concept of “leverage”. Any employee can leave your company, no matter their circumstances, the only difference is Jane could probably give you 2 weeks notice today and Sara might have to line up a new job first. Second, it sounds like Jane’s performance is good, you just don’t like that she told you she was taking time off, rather than asking. Your response should be the same of any employee: Can the company function for that amount of time with the role empty* and, if it can’t, say no, if it can, say yes, if it is a “yes, but” then come up with some conditions (e.g. check email, attend X, Y, and Z zoom meetings). Third, do you really feel Jane is undermotivated? Or is it that you feel she isn’t scared/intimidated enough? Because if her work quality is that good and she doesn’t need to work, I’m thinking motivation isn’t a problem here/

    *But really never have a situation like this. What if someone had a medical situation that took them out for a few months, went on parental leave, etc.? You need to have plans for this

    1. Teapot Repair Technician*

      she told you she was taking time off, rather than asking

      It’s not even clear that that’s what happened. If I went to my boss and said, “In order for me to continue working here, I need a month of unpaid leave this summer,” am I telling or asking?

      Either way it doesn’t seem unreasonable to me. I could easily imagine myself making a similar demand/request, and I’m not even wealthy.

      1. DANGER: Gumption Ahead*

        I was wondering if it felt like telling because the OP has it in her head that if they refuse Jane anything she will bounce, which might be an OP thing, not a Jane thing. I’m guessing that if Jane had threatened to bounce after being refused something in the past, the OP would have mentioned it as an example, so this might be a fear based on no evidence. “I don’t do this job for the salary, I do it because I love it” doesn’t sound like someone who would just leave the business in the lurch. It sounds like someone who likes their work

  40. bananab*

    I wonder what this person’s actual role is on paper. That list of duties is full of a lot of very different things, so I assume at least some of it is tack-on stuff. If so, one way to keep her happy (note: not “leverage”) might be to let her focus more on whatever her actual job is, or if she prefers one of the tack-ons, see how plausible it is to let her focus more on that.

  41. learnedthehardway*

    While I agree with everyone else that the real issue is that the OP’s company is too reliant on Jean and that the business needs to have its institutional knowledge documented and accessible to other people, I think there’s an argument to be made here that the business needs to decide whether it WANTS to accommodate Jean’s expectations or not, and how much it is worth it to do so.

    It’s all very well for the business to treat all its employees in terms of prioritizing retention, rather than having leverage to make them do their jobs, but there’s a limit to which a company can make the role ideal for the employee. It’s not acceptable in most businesses for a person to take a month off with limited notice, because that has a huge impact on productivity. Similarly, someone who decides that they want to work from 2 PM to 11 PM rather than regular office hours, or from Thursday to Monday (taking Tuesday & Wednesday as their “weekend”) – well, that may just not be workable.

    I once managed a team on which a couple of people simply were doing their jobs. I would find out at 10 AM, for example, that they’d decided to take the day off, when I was calling them to find out the ETA of assigned work, etc. Or they’d refuse work because they didn’t like doing it. One of them was managing a house renovation while saying they were working from home and was managing a second business, too boot. No amount of accommodating was going to change the fact that the two people simply had other priorities. I had to state the expectations, and hold them to those expectations. In the end, one of them quit, which was a relief, honestly.

    For the OP – once you have gotten your institutional knowledge secured, I would set some expectations and ask Jean if she can meet them. I would also look at whether meeting her requirements would set up inequities in your business (ie. with other staff who may be resentful that Jean gets more vacation, better hours, more interesting projects, etc. etc.) I’d be figuring out some workarounds, like cross-training staff on areas Jean handles, making sure that there is a backup contact person for key clients, etc. etc. I’d also set some expectations with Jean – for example, you may be willing to accommodate a month off, but you need 2 months notice and for her to include the backup person on client calls for 2 weeks beforehand.

    Basically, decide how far you want to accommodate Jean, and make some transition plans in case she isn’t willing to be accommodated at the extent you want.

    1. FD*

      I agree with that. It’s a business relationship. Jean gets to decide what conditions she’s willing to sell her labor for. You get to decide what conditions you’re willing to buy that labor for.

      She’s lucky in that she doesn’t have a strong financial need to work. But this letter wouldn’t be that different if she was a rock star employee who knows she could walk out and have 3 job offers within a week.

      Try to take the personal elements out of it and figure out what terms do and don’t work for you both. This is how negotiation is supposed to work!

    2. cncx*

      just commenting to amplify the bit about how meeting her expectations may make some others resentful re more interesting projects.

      i just left a job that refused a training and direction for me- and like, fair enough, maybe they thought i couldn’t hack it and other people were better but like….the job i accepted hired me literally to give me the exact training my ex employer refused so obviously someone thought i was worth it and smart/capable enough to do it

  42. Girasol*

    A lot of people need a paycheck but they don’t need *your* paycheck. In that sense, everyone on the team is just like Jean.

  43. andy*

    You should deny her the unpaid free time, so that she fully understands where she is working and can find job that will value her.

    Seriously, you have good worker that does job of two people and is likely underpaid. And you don’t value it at all, because you can’t threaten her.

    1. DANGER: Gumption Ahead*

      Who is at her job because she loves it. Who most likely doesn’t want to see the business hurt because she loves the work.

      1. andy*

        Yes, there seem to be plenty of space for middle ground. Jane wants to be at home with teenager, it is not like she is about to have baby that requires 24/7 care. I have seen long free time where they agreed to be available for emergencies or few regular duties.

        1. DANGER: Gumption Ahead*

          Shoot, this might be a time to ask her to document stuff and cross-train some folks to cover the basics so that if Jane is caught in a tornado and swept away to Oz the business doesn’t implode. If Jane agrees to be available to answer the questions of the cross-trained folks and to step in to put out any fires, it seems like a win-win.

  44. Jennifer*

    I also think people might be focusing a bit too much on the word “leverage.” Maybe it was a poor choice of words, but I think the OP is saying they feel they have no say at all in whether or not their employee takes time off because if a request is denied she’ll just quit. Working for such a small company with that kind of an attitude is a huge problem. She just needs to be told that she has to follow the same procedures for requesting time off that any other employee would. If she enjoys the work as much as she claims, and cares about the company’s success, that shouldn’t be a problem.

    1. DANGER: Gumption Ahead*

      Are we sure it is Jane’s attitude, though? Has she ever threatened to quit before if not given what she wants? The OP didn’t mention a specific event or example. Jane just said, “I don’t do this job for the money, I do it because I love it” and the OP took that to mean, “Therefore I get what I want” rather than “I’m happy here and want to stay”. We don’t know which it is, but I’m wondering if the OP is afraid of something that isn’t there?

      1. Jennifer*

        That is a good point. I hope the OP comments and clears things up. It seems from the letter he thought he had to grant her request, but is that based on assumption or things she has said or done in the past?

    2. Anonymous Hippo*

      But it is about leverage, if we take the LW at their word. They didn’t even try to discuss the one month leave because they won’t have the ability to throw down a trump card and win. This would be a totally different conversation if they had gone to Jean, and laid out business reasons why her plan would cause issues and try and work out a solution that works for everyone, but they didn’t even try because they can’t “win” the confrontation.

      1. Jennifer*

        I do see your point, but I guess I’m saying I don’t see the OP as some evil boss who thinks they need to hold someone’s paycheck over their head to control them, but more that they have an employee that they think they can’t really manage. I wish the OP had provided more details about that beyond the fact that Jean is wealthy. As a matter of fact, how does the OP even know she’s wealthy? Did they figure it out based on a few details she’s dropped into conversation here and there or has she come out and said, “I don’t need this job cuz I’m RICH!!”

        1. Anonymous Hippo*

          I’m not gonna call them evil either, fact of the matter employers have become complacent with the idea that they hold the trump cards because people need jobs, and in order to be a “good” employer you need to create an atmosphere of mutual respect.

          The attitude reminds me of that facebook quote that was going around a while back…

          Sometimes people who are used to being treated like an authority say “if you won’t respect me I won’t respect you” and they mean “if you won’t treat me like an authority I won’t treat you like a person”

      2. aebhel*

        Right, it sounds like LW has no idea how to have that conversation if they can’t threaten their employee’s job, which… is not a great mindset for a manager.

    3. Geillis D.*

      Yes, especially the “working for such a small company with that kind of attitude is a huge problem”.
      I work for a small accounting firm. One of the employees works casual, part-time hours as she is financially secure. An additional complication is that she is a close personal friend of the owner. She is not a senior and her duties have lots of overlap with other employees so she is not a Jean. This is fine during the slow months. During crunch time… it can be highly problematic. She comes in when she comes in, she does a good job, and she steps away whenever she feels like it. To those who haven’t experienced accounting public practice during tax season – it’s all hands on deck, there’s a sense of urgency that makes it impossible to skip work unless you’re actively bleeding. We need everyone there and present. Anyone not physically there is seriously impacting everyone else because we are stretched so thin. Having someone who only works when they feel like it is seriously demoralizing to others who have our office hours in their job description. In a perfect world we would all work for the fulfillment of it. The reality is that work is sometimes exhausting and demanding and we would prefer to be able to just walk away when we don’t feel like working anymore. Most of the employees in the office don’t have that option and it grates to see someone who does.

      1. Jennifer*

        Yes! This is what people are missing, I think. The vast majority of the population does not work for the fulfillment of it. They work because they need money and healthcare. If someone does not really need their job it DOES change the dynamics in the workplace, especially if everyone else there really needs the paycheck.

        1. Geillis D.*

          This, exactly. I drag myself to work on snowy Saturdays in March and spend weekends in April doing people’s taxes rather than working in my garden or lounging on a beach somewhere because if I don’t, clients would leave and my workplace would be kaput. This is where I’m at – if I don’t work I don’t eat, same as the owner of the office. Missing the tax deadline because Lucinda went skiing rater than work weekends in April is a risk, because sometimes showing up is not optional.

        2. Geillis D.*

          I wish we had an “edit” option.
          A senior employee has left recently. Her work load is supposed to be distributed among other employees until we hire a replacement. The full-time employee who works because she actually needs the money is shouldering 100% of the extra burden and is naturally stressed out. Lucinda is off because who wants to work during the summer? Of course this breeds resentment.

  45. RedRabbit*

    OP, people take leave for lots of reasons — your letter would read very differently if it was about maternity / parental leave, medical leave, FMLA, caring for a dying relative, etc. And in some cases you might have to provide paid leave.

    Detach Jean’s personal finances from this. Generally how is your business prepared to handle leave from any employee? And consider the unpaid aspect of Jean’s leave as a way to potentially find a temp or part-timer who can fill in the most needed gaps.

  46. forgotmyname*

    I’ve actually been in the same position as Jean and it’s great. When the company does really want and need you, and the truth is that you don’t need the job, people do not talk advantage of you because they know you will walk. You really do have leverage and can set very clear boundaries of what you or are not willing to do, and if it works for them great, and if not, then no problem, you are perfectly content to step aside and let them hire someone who wants that level of responsibility and time commitment. I have worked at other places that totally took advantage of employees because they knew they desperately needed the job or had to accept undesirable parts of a job as part of the job role. When you can say Lol no thanks or they know they will lose you, and are not willing to do that, the shift is quite nice and you get a quality of life kind of job that works for you. And the thing is, if they want someone else in that role to do more – then it is totally fine if they want to go in another direction!

    1. feral fairy*

      it’s really unfortunate and not “great” then that people who don’t have an affluent partner or wealth independent of their job are treated worse and taken advantage of. Good for you that you have more leverage, but the fact that your employers are in effect favoring wealthier employees leaves a bad taste in my mouth. I’d encourage people in that position to use some of that leverage to stick up for their colleagues who don’t have the luxury of just quitting without anything lined up.

      1. forgotmyname*

        Fair enough, but I should clarify that at the place where I was basically able to set my own parameters and keep it as a hobby job, it didn’t really impact anyone else or their role. And my employers were really nice people and were very clear that they wanted me to be happy there so that I would stay, and were very willing to negotiate not just salary but job responsibilities there. At that place, it felt more like they valued me than like a having leverage thing.

        The previous job I had, I was completely overqualified and underemployed and there was going to be nooo way they were going to get someone competent to do that job at that level for the pay they were offering. So I was very clear on what I would do and not do and what hours I wanted to work and set very clear boundaries that annoyed my bosses, but they really couldn’t afford to lose me. I saw the way they pressured part time employees to work a million hours and unfavorable times and there was no way I was going to do that. No it’s not fair that other employees didn’t have that same “leverage” but they also were hourly employees without the any type of professional/corporate experience, skill set, etc. I wasn’t getting paid that much more and was bringing so much more industry experience, contacts, and bringing in a whole lot of money. So yeah, they pretty much were hands off with me and I was able to set my own schedule, time commitment, work from home, etc. But I would say any “leverage” came more from them being cheap and wanting to keep my skill set for that pay, and knowing that most people would not do that job for that pay.

  47. nothing rhymes with purple*

    It’s pretty telling that LW finds it a problem that Jean cannot be manipulated by dangling her salary over her head because she doesn’t need it. I wish that weren’t such a common management tactic and I have always suspected that many of the managers who use it enjoy doing so on some level. But when my managers have said to me “dance for your pittance, peon!” I had to put on my tap shoes, however painful. I’m kind of glad for Jean that she doesn’t have to.

  48. WonkyStitch*

    I would think if she wants to take a month unpaid leave, fine, just give you 2 weeks’ notice and train 2 temps to work for that month before she goes. Simple.

      1. kicking_k*

        Given that this is standard operating procedure in countries where parental leave is longer… yes? When I went on maternity leave I knew they were hiring a cover person. Earlier in my career I’ve also been a temp who was hired to cover for someone on long-term sick leave.

    1. random tuesday*

      I’m just amused that 2 weeks is enough time to train someone to take over a job. I have a new hire that I’ve been training since June…. and she’s almost but not quite ready to take over my duties. And, that’s only for one role I do – about 2/3 time.

  49. moneypenny*

    This reads like a short-sighted, paranoid employer worrying about A Situation instead of all the wonderful things, by their own admission, they have in one single person. Rather than let her walk over and tell people she’s taking this time off end of story, she didn’t leave room for a conversation so starting there makes a lot more sense. Not ‘if we do it for you, we have to do it for everyone’ so much as, ‘let’s find a way that this works for us both’, and if at the end if the day the owner needs to write up a vacation policy, so be it, but getting run over by an employee and then complaining about the employee is something other employees notice. And THAT’S the employer should be worried about.

    1. CommanderBanana*

      Right? An employee who is amazing at her job, does it because she loves it, does the work of two, clients love her, tons of institutional knowledge, broad skill set and your concern is that you don’t have enough leverage to prevent her from taking time off to be with a kid who is heading off to boarding school? Really? Yes, by American standards a month off is a long time, but our relationship with work and time off is seriously messed up in this country. My hat is off to Jane for prioritizing spending time with her kid before they leave.

  50. Alict*

    As someone who has often been at the mercilessness of employers because of “leverage” like my healthcare and rent and food, the only reaction to this I can really muster is, “Well well, how the turn tables.”

    It’s amazing how employers panic when suddenly they don’t control your ability to survive. I suspect Jean is fully aware, and I want to shake her hand. Imagine if we l got to be treated as people.

  51. CommanderBanana*

    Eeeeeeegh. LW, as a manager, if you’re acknowledging both that 1. an employee has institutional knowledge that can’t be replaced but isn’t documented anywhere and 2. they’re doing the work of two people, you have to issues you should be thinking about addressing.

  52. Lobsterman*

    If a business would tank if a given employee quits, then that isn’t an employee – it’s a partner that the management is seeking to deny their due.

    I really enjoyed this letter, and I’d love to read Jean’s counter-letter and watch the fireworks when Jean quits after realizing how much her employer loathes her.

  53. Kate Kate*

    I was actually this person a few years ago due to a large insurance settlement. Tons of stress sickness left me with very little PTO, so I’d take leave without pay for vacations, because, hey, I had money. I only had one boss push back on it and his response was “what if Jeremy wanted to take off a month without pay?” I responded that I literally would not care, and he and my supervisor were both dumbfounded that I wouldn’t care. What business is it of mine? However, I never acted like I didn’t need a job, or lorded it over my employer. I honestly liked what I did and I was damn good at it.

  54. JessicaTate*

    I want to acknowledge that the vibe that can come off of a “Jean” relationship is different than “normal” employees, and I can imagine it feels unusual to manage. (In other words, follow Alison’s advice. It’s great.)

    The use of the word “announced”, combined with my experience working with a Jean — someone who said, “It’d be easier if they just didn’t pay me. The tax headache this paycheck causes us is terrible” — leads me to think there is a tone of mild entitlement. Our office’s Jean didn’t follow any rule she didn’t want to. She cared very much about her job, and would never do anything egregious; but I can totally see her announcing “I’m taking a month to be with my kid,” without any sense of it being a discussion or question or something she needed to run by… anyone. It wasn’t an adversarial “They need me more than I need them” thing. It was just someone who had spent her entire life on the very smooth path of the wealthy, and it made her oblivious that the rest of us don’t get to do exactly what we want when we want — especially at work. Her boss and staff were more conscious than she was about WHY she was able to ignore rules, the supposition that she would walk if someone stopped her (and her entitlement required the boss to actively stop something, not just deny a request). It created an unusual dynamic that I’ve not seen in any other work interaction. Per Alison’s advice, it doesn’t need to play out that way, but it did.

    So, Alison’s advice is great. But the fact that the dynamic feels weird to OP and not like a normal management challenge — I get that.

    1. Geillis D.*

      +2. Spot-on. ” It was just someone who had spent her entire life on the very smooth path of the wealthy, and it made her oblivious that the rest of us don’t get to do exactly what we want when we want — especially at work.”

    2. Uh huh*

      The only “entitlement” I’m getting off this letter is that of the LW, who seeks power over his employees, and is angry and frightened that he can’t use “leverage” to force Jean into doing what he wants.

    3. Jennifer Strange*

      I feel like you’re projecting your experience onto this. I don’t see Jean as coming across as entitled (at least not without knowing how she “announced” her one month off). I see her as someone who is clear about what she wants. We don’t know that she announced it “without any sense of it being a discussion or question” just that the OP didn’t push back (which is on them). For all we know if the OP had said that won’t work she would have accepted that or negotiated. The inaction on the OP’s part isn’t Jean’s fault.

  55. RJ*

    Looks like Jean got exactly what she needed to be C suite without technically ‘becoming’ C suite. She’s intelligent, has strong client capacity and is working out of professional need. Forget about ‘leverage’, OP. You need to start thinking of a backup plan if your need for power surpasses your need for happy clients, because replacing Jean is going to be a major PITA, particularly in this labor market. Or you could focus, as Alison advised, on creating the work environment that will encourage and foster Jean to stay and continue to make your business flourish.

  56. can-relate*

    I’m sure that LW is actually one of the (sadly all-too-rare) good employers, but this letter is a brilliant demonstration as to why we need a universal basic income (UBI). It takes so much of the power that the numerous bad employers out there use to hold people hostage to bad treatment, bad wages, and bad working conditions.

    Imagine if, instead of having to put up with a bad workplace or boss (even if only while job hunting in a good job market), employees could just quit, knowing that they and their loved ones weren’t risking homelessness and starvation because they’d quit an awful job/workplace which was damaging their health, and without having another job lined up.

    Employers would have to make themselves seem attractive to workers – and actually BE attractive to workers – instead of being allowed to get away with blue murder because the employers hold all the power in a system wherein perople’s livelihoods are tied to working (and their health insurance is, too, in the US, which is so messed up).

  57. nnn*

    One train of thought that might be fruitful is to think about what you did before Jean came along. How was all the graphic design, copywriting, strategy, account manager, etc. work getting done?

    Also, how did you go about finding and hiring Jean? Could you replicate that process? (If not, why not?)

  58. caps22*

    Succession planning isn’t just for CEOs; it should be something to think about at every level. That’s not to say employees are fungible, but just that anyone can get hit by a bus or win the lottery or leave for any other reason that has nothing to do with the job itself. You just want to minimise reasons why a good employee would want to leave due to job-related reasons.

  59. NinaBee*

    This reminded me of a guy on Tik Tok who has ADHD and created a ‘wildcard’ agency for hiring people who can do multiple things (agency/website is called Wildcard People). It was literally because neurodivergent people can wear many hats and be good at many roles (aka swiss army knife types).. could be worth considering if it would work in your location? I’m not affiliated in any way, just mentioning Jeans multiple skills reminded me that there’s people out there that could be suitable as well.

  60. inoffensive nickname*

    In my very first management position, I explained that my husband was the primary breadwinner, and I was working because I wanted to, but my family would always come first. My boss (son of the owner), who turned out to be the boss from hell said to me, “How do you think that makes me feel? Your JOB should come first!” That was the first red flag in a series of “WTF just happened?!” experiences over the course of ten months. It also turned me off of management for the next seventeen years and made me feel like a miserable failure. This ex-boss leveraged something over every single person who worked for him, but since I was there because I wanted to be, he had nothing to hold over me and he made my life hell to the point where I had nightmares about him for two years after I was fired.

  61. Sleepless KJ*

    No employee should be able to hold you hostage. She needs to be treated the same as you would any other employee (her financial status isn’t anyone’s business but her own) and you need to have detailed SOPs (including notes on clients etc!) for every job in your company so that you’re not left in the lurch should any one of them leave.

  62. Sarah*

    I’m super curious where Jean is coming from on this one, as far as announcing the unpaid leave. For context, I recently took a better paying primary job that makes the pay I get at my second job not actually worth the time I spend there – but I honestly really enjoy it so I’m staying on. Because I do enjoy it and value my coworkers and manager I would absolutely have a conversation if I needed extended time off and try to work it in a way that didn’t unduly burn anyone else out making up for me being gone. If I *had* to put my foot down I would, of course. But my first step would be conversation rather than announcement.

    Second job also has clear policies for requesting leave, so there’s also the part where I know I would need to follow them the same as anyone else.

    I’m probably the best trained in my area right now since we’ve lost a bunch of people, but I also recognize that if I’m not there to do the job, they’re going to have to find someone else who can. It’s great for them that they can let me loose and not have to worry about me knowing what needs to be done, but only if I’m actually there reliably.

  63. RJ*

    I agree with the advice here. I had someone on my team who needed a month off for something once and, when she told me, I immediately understood that she wasn’t asking if she could take the month — she was asking if she’d still have a job when she came back. And, it wasn’t difficult at all to say yes because she was so valuable. It was inconvenient that she was gone for a while, but sometimes that’s the price you pay to work with human beings.

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