my long-time employee pushed to become a contractor … and the relationship fell apart

by Alison Green on April 8, 2026

A reader writes:

I run a small healthcare practice and recently had a difficult transition with a long-time employee that I’m trying to learn from.

Sarah worked for me for about five years as our director of business development and marketing lead. During that time, I invested heavily in her development through training, tools, and absorbing the inevitable mistakes that come with someone growing into a role. She worked remotely, set her own schedule, had significant autonomy, and earned well above the market rate. I also referred clients to a small side business she ran.

About six months ago, she told me she had “outgrown” the organization professionally and wanted to change the relationship from employee (W-2) to contractor (1099). I raised some concerns about that transition, which led to an emotional conversation. Shortly afterward, she followed up with an email summarizing the conversation as though I supported the transition.

As we tried to work out the details, it became clear she didn’t fully understand the legal and structural differences between W-2 and 1099 work. Once we started mapping out the contract, she realized that many of the duties she previously handled could not legally remain part of a contractor relationship, meaning the scope and compensation would likely be smaller than she expected. She was upset and accused me of not being supportive.

After a lot of negotiation, we eventually arrived at a contract that met the legal definition of a 1099 relationship, and my company became one of her clients for several marketing services (social media, blog writing, online ads, and outreach).

Almost immediately after the transition, the quality of her work dropped significantly. When I raised concerns about deliverables, she responded by unilaterally removing two services from the agreement. Our contract allowed 30 days’ notice to terminate the agreement but did not allow individual services to be withdrawn while the contract remained active. At that point, I concluded it made more sense to transition to a new marketing firm rather than continue the relationship.

The whole situation has been frustrating because I feel like I lost someone I invested heavily in and tried to support. In hindsight, I also suspect she may not have actually wanted the contractor arrangement once she understood the implications, but by that point the relationship had already shifted.

My questions are:

When a valued employee pushes for a transition from employee to contractor, how should a manager handle that conversation?

Is it generally a mistake to agree to become a client of a former employee to preserve the investment you’ve made in developing that employee?

How do you avoid entirely losing someone you’ve invested in when they push for a change like this?

I’m trying to understand what I could have done differently so I don’t repeat this situation in the future. As a small business, a loss like this is huge. I feel nervous investing in the future, and I can’t shake the feeling I should’ve handled this differently.

The first thing is to accept that you will always lose employees who you invested in eventually, and that’s okay! If you try to stop that from happening at all costs, you can end up making choices that don’t serve the organization well. So first and foremost: be okay with the idea that people will move on and that it’s a natural and unavoidable thing that will happen in running a business.

I say that because it sounds like this all stemmed from you trying to find a way to hold on to Sarah, even if that arrangement didn’t make sense for the business. Instead, when Sarah told you she felt she’d outgrown the organization, it probably would have been better to wish her well and make a clean break.

There are times when converting a valued employee to contractor status can make sense for all parties. If you look at what the employee is proposing and can come up with an arrangement that makes sense for both of you — not just “we’ll agree because we’re desperate to keep them,” but truly makes sense — then great. But you shouldn’t agree just because they suggest it.

In Sarah’s case, it sounds like you were searching for a way to make things work even when you had significant reservations. It would have been okay, and probably better, to turn down the contract conversion — if not at the start, then definitely after your conversations revealed that you were so out of sync on what it should look like. You could do that without it being adversarial; it’s perfectly supportive to say, “I would love to keep working together, but we really need the person doing this work to be an employee. If that can’t be you anymore, I understand.”

You’ve framed this as wanting to figure out how not to lose the investment you’ve made in a good employee. But benefitting from your investment in a good employee doesn’t mean “they stay here forever.” It means your investment pays off in their good work while they’re there and in how their work hopefully sets the next person up for success. It also might pay off in the satisfaction it brings you to work with someone who you’ve seen grow and develop. But they will eventually find other opportunities and move on, and that’s just inherently part of running a business and employing people. You will make better decisions for the business and for yourself when you’re okay with that.

{ 58 comments }

{ 58 comments… read them below }

  1. I should really pick a name*

    Shortly afterward, she followed up with an email summarizing the conversation as though I supported the transition

    This makes it sound like the LW didn’t support the transition, but it’s followed by:

    As we tried to work out the details

    What was the reason for the change?

    1. Antilles*

      Pretty sure the reason was just that OP was emotionally invested in continuing to work with this person they’d taught and helped grow. So when Sarah made it seem like OP was on board, OP was willing to give it a try.
      This is also why OP didn’t nope out once it became clear the details weren’t what Sarah expected, and also why OP didn’t nope out when Sarah accused OP of “not being supportive” for needing to follow government rules around 1099s.

    2. Martin Blackwood*

      I interpretated it as OP would rather Sarah stay an employee than transition to contractor but, as Alison says, was more dedicated to keeping her on so negotiated.

    3. Whale I Never*

      To me it sounded like a tonal difference. Like LW approached the conversation by saying “We can talk about transitioning you to that role but I have significant concerns about how to make X, Y, and Z work” and then Sarah sent an email saying “As we discussed, you are fully onboard with this decision and will make it happen regardless of any obstacles.” So LW was never a firm no on the idea, but had not been an enthusiastic yes, either.

      2. GammaGirl1908*

        Also, LW sounds like what they really wanted was to keep the status quo, and having Sarah in any capacity was closer to the status quo than losing her, so they went with it.

        Unfortunately, some Sarah ended up not being better than no Sarah.

        Agree with AAM that LW needs to be much more realistic that it is normal and expected for people to leave, even when you’ve been great to them and invested in them. Trying to hang on to them at all costs leads to, well, work advice-column letters like this one.

    4. Cmdrshprd*

      I think it might be a difference in the definition if support.

      I suspect OP viewed “support the change” as “I am happy about it and excited about this change, I want it to happens.”

      while the employee might have been seeing support the chance as “OP agreed to make the change and find a way to make it work.”

      If I propose a plan to my boss and they say “I don’t like the plan and think it is wrong, but I am giving you the green light to move forward with it.”

      I think it is reasonable/fair to say my boss supports the plan, they might not agree with it but they support it.

      I suspect that is where the difference came in.

      1. fhqwhgads*

        Yeah, it’s the difference between “support” = “said yes” vs “didn’t say no”.

  2. 2 Cents*

    OP, it can work out that a former employee contracts / freelances for a former employer. I’m doing it now — though there was time in between when I worked for said company and then came back as a freelancer. It was also very clear to me the differences btw an employee and a contractor.

    1. Ama*

      I consulted with my previous employer for about 18 months after I decided to go full time freelance. The main difference, however, was that my employer proposed the consulting arrangement (I had been there over a decade and they were concerned about losing access to all my experience while my replacement was working through their first annual project cycle) and I was the one who set limits on what I was willing to continue doing. We also set up the agreement knowing it was always designed to end once the replacement staff felt more comfortable making the judgment calls my role required without my advice.

      I had also fully prepared for being a contractor long before I transitioned (I had been taking small contracts in another industry as a side gig for over a year while still working full time), this included already being registered as a sole proprietor in my state and having an EIN. If I had been as unprepared as OP’s employee they probably would have wished me well and just made do without my help.

    2. BigTenProfessor*

      I left my corporate job to go back to school full-time. I continued doing some contract work while I was in school. It seems like a key theme in success stories is that it happened after some other change, but wasn’t the DRIVER for the change.

    3. allathian*

      I’m in Finland and I work for the government. Here the rules on retirement are very strict, people can and most do retire much earlier, but on your 68th birthday you’re basically declared unfit to work any longer and fired if you don’t go willingly. There have been cases of people with some very sought after niche skills being hired as part time contractors after retirement, with all that implies re taxes and benefits.

      The age limit applies to employees and civil servants but not political appointees or elected officials.

  3. Asloan*

    I know at my work, we do not allow employees to return as contractors for a certain length of time, I think a year. While it seems hard, there’s a few good reasons for that; first, it was being abused by retirees who then returned as contractors basically getting these roles through nepotism; they were not being competed or evaluated fairly. Second, there are IRS standards that affect turning employees into contractors which it sounds like OP understands. A blanket policy across the board is not a bad way to go IMO, to ensure it’s not just people panicking at the first separation but is truly a strategic business decision.

    1. RIP Pillowfort*

      This is the way my workplace does it. We have a lot of people that come back to work as consultants (contractors) in different capacities. But they cannot transition directly from an employee role to a contract based one without a period of time (I forget if it’s 6 months or a year).

      Part of that is to allow for a different work relationship on top of other ethical obligations. I literally have one of my old bosses working as a consultant now. It’s very weird being in a co-worker style relationship or one where you’re the one in charge of ensuring they’re meeting deliverables with someone that was in charge of your deliverables for years!

  4. Asloan*

    OP you sound like a few people I know who run small businesses – maybe slightly over-personalizing things? They also frequently remark that staff doesn’t return their loyalty after all the hard work / generosity they’ve show them. They frequently feel burdened by all the great things they’ve done for ungrateful employees. I feel like such comments are an indication that people aren’t using logic and reason to make business decisions. You shouldn’t over-extend yourself for employees out of the milk of human kindness; you should make fair and transparent decisions that serve both you and your employees. If you had always trained Sarah with a clear-eyed sense of the near-term business benefits of doing so, you likely wouldn’t feel as put out when she decided the organization no longer served her career.

    1. Davey*

      Wow. Leaps and bounds based on zero evidence. Please don’t.

      @LW: Good for you for taking an honest look in the mirror and letting hindsight show you the way. It’s rough to lose a good employee, but it was wise of you to ultimately go with a marketing company.

      1. Sara_bellum*

        Doesn’t seem like a stretch to me. OP mentions “investing” in Sarah at least twice, and also mentions “the loss is huge”.

        What loss? Yes, it is a bummer that the arrangement didn’t work out. Maybe money was lost on deliverables that weren’t usable (when they dipped in quality). But… people leave. Even after a company invests in them. That isn’t a loss someone needs to work to prevent in the future.

        1. MsM*

          People leave, sure, but I don’t think it’s wrong to want employees to be able to grow with the business if possible, rather than have to leave just as they’re coming into their own if they want to continue growing. Also, OP might be sad about the breakdown of the personal relationship with Sarah, which is a thing that maybe could’ve been prevented. (Maybe; if Sarah wanted the job entirely on her terms and that wasn’t ever going to work, maybe there was no saving that.)

          1. Specks*

            Of course, people generally continue to grow in their jobs, but 5 years is a lot of time to be “just coming into their own”. It’s very odd to basically frame it as 5 years of investment that just finally started paying off or be so shocked that someone is leaving after 5 years.

            Either OP didn’t hire the right person for the role if that much growth was needed, or there was just way too much actual investment in personnel development that was not necessary or justified by business needs at the time, or there is some really weird thinking happening around tenure expectations that maybe aren’t in alignment with 21st century realities for most employers. All of those point to something going on that needs reassessment and correction.

        2. fhqwhgads*

          I think it’s focusing on the wrong thing though. Sarah asked for this change. OP, unlike many many many business owners, actually new the legalities involved and approached it accordingly. It’s true, it’s not a loss someone needs to work to prevent in the future, and that’s the lesson. But nothing about what OP says reads like an overly personalized demand for loyalty. It reads to me more like OP felt like they were negotiating in good faith – and insisting on following the law – and Sarah was both unaware of the relevant laws and perhaps not negotiating in good faith. I think Sarah probably just didn’t know what she didn’t know. It’s not unreasonable for OP to feel like maybe this wasn’t a good faith effort on both sides, but I also don’t think either of them actually acted unreasonably. Sometimes things just don’t work out, and it can feel bad. And that’s OK all around.

      2. Pancakes Stack*

        This is an odd comment to make when you don’t actually know the circumstance. LW is showing similar signs as small business owners when it comes to retaining employees. LW is an adult and can decide if the comment applies to their situation. It’s sound advice.

        1. allathian*

          Too many business owners forget that employees will never be as invested in the business as the owner, and it’s completely unrealistic to expect that they would be. They’ll move on when it makes sense to them.

          Sure, decent employers will invest in the professional development of their employees but they’ll do so in a way that allows them to reap the benefits of that investment for a time but not forever. ROI is a thing even in professional development. When you calculate the ROI, don’t assume the employee will stay forever.

          A friend’s former employer paid for an expensive (five figures) certification for my friend with the condition that she’d continue to work for them for three years after she got it, or she’d have to pay a prorated amount to the employer. She got headhunted a couple years into that period and the new employer paid an extra signing bonus that covered the amount she owed her former employer, including tax.

          1. Orange Juice Bop*

            I could be wrong, but with it being a small business, I wonder how competitive the pay is. I worked for a small business. Usually they try to compensate the pay with training. I took all the training and education I could and the left after the agreed time. Within five years of leaving, I am making $43,000 more that my starting salary.

      3. Ellis Bell*

        But part of “taking an honest look in the mirror” is to assess mistakes and what you can do differently. It’s not a snark at OP to do that. When someone owns their company, they do tend towards greater emotional attachment, personal sacrifice, and to invest more heavily in outcomes because the buck stops with them. It’s actually a very good set of traits for getting a business off the ground and through rough spots and it’s beyond natural for those tendencies to bleed into places where it’s less helpful. I also disagree that there’s “zero evidence” that OP may have over invested in this employee. There are numerous mentions in the letter of how “heavily” OP invested to avoid “entirely losing” someone, which is an obviously impossible goal. I don’t think this sense of over investment was all on OP’s side either. As someone who was getting clients for her own business from OP, Sarah herself seems a little bit too enmeshed and actually, a lot more emotional and less clear sighted about it than OP. However both sides should have said “eh this probably isn’t a fit” much sooner.

  5. Commanding Nothing and Loving It*

    It sounds like you feel burnt that you financed so much of their training without getting the expected return on your investment. For future reference, you can always write a claw-back clause into training a training agreement where you can get the money back if the employee departs within a certain amount of time.

    1. Cmdrshprd*

      “you financed so much of their training without getting the expected return on your investment. ”

      I think you are right, but I think OP had/has unrealistic expectations. Sarah worked there for 5 years, I would say that is a decent return on investment. If Sarah had left after 1 year, maybe even 2 I could see OPs side more. but 5 years is decent.

      If OP is expecting 7/10+ years I think that is unrealistic, it is nice if it happens and someone probably would be happy to be in a role long term, but you can’t expect it.

      1. Antilles*

        I agree. I’d also note that OP’s statement of “training, tools, and absorbing her mistakes” likely includes a lot of things that are not in any way subject to a claw-back clause. Both the tools and the patience are obviously not covered. But I would also suspect that what OP calls training includes a lot of things that wouldn’t be part of a training agreement either. Learning the software at your desk, webinars, reading about the topic, shadowing OP, etc. There’s a reason these sorts of claw-back clauses are typically only used for discrete clear events like educational degrees or industry certifications.

    2. MsM*

      Or just put a cap on professional development reimbursement that the business can absorb without feeling bitter about it or triggering a potential fight if the employee leaves? You can always have the amount go up based on seniority if you want to incentivize people sticking around.

    3. Orange kangaroo*

      I think it depends though if it is training you need the employee to undertake.

      Clawbacks make sense if you’re funding training that benefits mostly the individual, not training you expect an employee to undertake.

      I think in my country – outside of military training – you can’t require that someone work for a certain length of time because you’re investing in them. I think you could only have a clawback for optional training. The employee needs to be able to say oh no I’m not interested in doing that training.

  6. Dido*

    I highly doubt OP is going to run into this situation again. How many people want to go from an employee to a contractor? I’ve never heard of anyone doing else unless they were just staying on top help with some part-time or ad-hoc work

    1. TerrorCotta*

      I think Alison correctly caught that the LW was more upset about “investing” in employees who might leave (which will indeed come up again) than the more specific things with this one situation.

      1. B’Elanna*

        Yeah, and emotionally I can kind of get it. I had a situation where I was supposed to train someone for a technical role and as soon as I’d gotten them up to speed after six months of fairly intensive training, they quit. I was just a senior colleague and none of my money was on the line, I had a gut feeling of “oh for god’s sake,” lol. But I was aware that the annoyance was not their fault, it was just unfortunate timing that couldn’t be helped, so I whined about it to my friends over beer and then moved on. It’s ultimately just business.

        1. TerrorCotta*

          Oh definitely! The frustration/exasperation is totally fair, and venting is to be expected. Hopefully LW can learn to see it with the same understanding you did.

        2. Specks*

          Except that totally makes sense after 6 months of training, not for 5 years of employment. It’s just such an odd reaction to someone leaving after a very reasonable tenure. I think Alison and TerrorCotta are picking up on something very important in terms of the actual gist of the question, and there’s something to dig into there for the OP.

          1. allathian*

            Indeed. I’m pretty sure the LW got some value for money while the employee was working there, even while she received training. The two most common reasons for leaving a job voluntarily (not counting firings, layoffs, or external circumstances like moving for your spouse’s job) are burnout, whether it’s caused by overwork or a toxic work environment/manager, and boreout, which is what happens when people feel like they’ve learned everything they can at a job and it’s time to move on. There are other reasons, like leaving an otherwise great job for more pay elsewhere, but often this is combined with boreout when the employee can’t get a promotion and raise at their current job and feel stuck.

            Obviously there was some reason why this employee wanted to become a contractor.

  7. Blue*

    When I moved a few years ago, I continued working for an organization as a contractor after having been a full time W2 employee. However, it was in a quite different role; my 1099 contract included two tasks that accounted for about 20% of my former role (and my hours of were reduced to 5-10 a week). It sounds like what Sarah wanted was to have essentially her same job but with the flexibility and autonomy that comes with being a contractor. And that’s just….not how it works.

    1. Bee*

      It’s also interesting because she already pretty much DID have that flexibility and autonomy – she worked remotely and set her own schedule! My guess is that this move was designed to bolster her own business: naming the OP’s business as one of her clients adds clout, whereas listing that as her full-time place of employment makes her own business sound like a side venture. She wanted to be able to leverage her work with the OP for additional business in a way she didn’t feel able to as an employee. But then it turned out she was going to have to take a significant pay cut to achieve that and everything soured.

    2. AcademiaNut*

      It’s such an odd ask that I wonder where it was coming from, because the usual progression is to go to a more challenging / advanced / higher paying role for career development, not to shift from employer to contractor status. There are some fields where it’s common to work as an employee while building experience, then to become a contractor later in your career, but that’s very specific, and usually involves a fairly significant change of work life. I wonder if Sarah came from a family with someone who did this, and thought it was more standard than it is.

  8. pinkponyclub*

    My comment is assuming this is in the USA….

    Honestly it feels like Sarah wanted to work less hours and make the same money all the while she could work her own business. My guess she needed some income to absorb her losses for her own business. In short she was using you for tax purposes. W-2 income is all passive income, but 1099 isn’t when she files with a Schedule C

    1. ArtK*

      I thought W-2 was considered active (earned) income since you are working for it. Passive is something like a stock where you don’t actually have to do anything for the value to increase.

      1. LippyTappyTooTah*

        This is correct. Both 1099 and W2 earnings are considered earned income. Passive income requires no (or minimal, I guess) labor.

        That said, I think PinkPony is circling something that’s correct–when a W2 employee wants to be re-classified, they are effectively resigning and soliciting their prior employer as a client of their business. I think LW sensed correctly the employee did not fully understand or appreciate why that wouldn’t automatically be an attractive proposition for the organization. There is a plausible scenario where a valuable employee believes that they can leverage their employer to be the Big Client that helps them grow their business.

      2. pinkponyclub*

        W-2 is passive in regards how she takes losses and expenses. In short a W-2 employee can’t take expenses for a business that they don’t actively participate in (think own and run via Sch C or F or E even). By switching herself to 1099, she can move that income to an entity (herself) and take business expenses if she structures to do so.

        In simple terms, it is a bit harder to hide W-2 income whereas it is easier to with 1099 if you set it up correctly (or with that intent).

  9. Casual observer*

    We deal with the independent contractor rules in my line of work (public entity) frequently. Local agencies who participate in our benefit plan sometimes think they can simply declare someone to be a contractor so they don’t have to pay into the system for them. That’s just not how it works. This LW could have consulted with an HR professional or employment attorney to explain all that to Sarah, since she didn’t seem to want to accept that news from the LW.

  10. George*

    Employers should realize that that investment in our growth is part of what we look for and our compensation to help grow our career. If I’m not getting that I’m looking for somewhere that can or compensation to make up for it.
    It isn’t entirely about getting a return on that investment, any more than the money you’re investing in us with a paycheck. You’ll benefit as long as we decide it is the place for us, and we’ll do the best to make it easier for the next person.

  11. QED*

    Yes, OP put time and presumably money into training Sarah and helping her be a good employee. But Sarah was presumably also making OP’s business better and improving the parts of it she worked on as she improved as an employee. So yes, OP, you made an investment in Sarah, but your “return” on that investment is all the work Sarah did for you and the ways that your business grew or improved over the five years she was in the role. If you don’t think that is equal or greater than what you invested in Sarah, then maybe you need to rethink the qualifications for the roles she was in. For example, if it was a stretch role with her qualifications, then maybe hiring someone whose experience more clearly matches what you need is a better idea next time and you won’t have to spend as much time on training. But in general, every employer assumes that new employees will need a little bit of time to settle in and figure out the specifics of their new workplace, and that just comes with hiring people. I’ve worked at places where because of that new employees agree to stay for a minimum of two years, but I’ve never heard of anywhere that requires a 5+ year commitment.

  12. Chaordic One*

    The decline in the quality of Sarah’s work is the key. If Sarah had still been an employee, and the quality of her work declined, the OP would have probably had to lay her off (fire her) and end the professional relationship. As a contractor, given the decline in the quality of her work, ending the contract and the relationship made sense.

    I get the argument about having invested in an employee and expecting a return from that investment. OTOH, there are lots of times when employees invest in an employer (relocation, voluntary education and training for a specific job) and never reap a significant return on that. As Alison points out, the OP had a good employee and a good working relationship for five years. It would have been nice if it could have lasted longer, but it wasn’t a complete failure.

  13. TerrorCotta*

    I thought this one was really interesting, because we normally see letters from the opposite POV – people feeling guilty for wanting to leave jobs because they recently received or were scheduled for education/travel/training/conferences, etc.

    I do think Sarah thought she could double dip by contracting, which should have been immediately rejected if it wasn’t going to be productive. But there weren’t any grounds for a claw-back (even an emotional one). Moving expenses, tuition, special certifications are usually covered (and contractually so) within two years at most, in my experience. What the LW provided in training and “accepting mistakes” is just the cost of growing *your* business.

    Anyway, now I’ve got a very specific 1980s Human League song stuck in my head.

  14. Has Been a Sarah*

    I say this kindly: Your return on your investment was the five years Sarah put into your business (and the good work she did during that time).

    If your practice was small and she had no further room for advancement (which sounds like the case, given her skill set and director-level title), it makes sense that she’d lean further into her remote/autonomous operations and decide to run her own business.

    Yes, she should’ve been more professional (and known what she was getting herself into), but to be honest, it sounds like the personal connection is where this really got messy.

    You “feel like [you] lost someone [you] invested heavily in and tried to support,” but… did you think Sarah would work for you forever? Is that a fair expectation?

    She didn’t leave after a week or a year; she was there for five.

    Training someone to do the job is compensation in and of itself. Befriending and trusting a colleague is, too. From personal experience, I can attest that boundaries, relationships, and feelings get blurrier in small orgs, but it may be worth interrogating that urge. It’s just business, and Sarah fumbling a career move doesn’t reflect on your investment or relationship.

    1. Has Been a Sarah*

      Ack, missed this in my edit: “Befriending and trusting a colleague is just part of doing business, too.”* not related to compensation.

    2. Dawn*

      Yes, the “I can’t believe she only worked for me for five years, that’s not nearly enough to repay me for everything I did for her” implication here made me blink out loud.

  15. Raida*

    An employee becoming a contractor is not inherently a problem.

    Paying only for the hours doing the thing they want to do, and specialise in, can be great!
    Removing a task load from an internal role opens it up to a wider range of applicants, and creates space to do other work.

    IF it is a case that these are skills we do need to not be helpless with in-house, then it’s not a good idea to let all the knowledge only really exist in an external company that gets paid more per-hour than staff. Better in that case to do cross-training and transition as the existing SME changes to working full time in their own busienss.

  16. Technically Australien*

    I’m not sure what either side of the discussion above expected, but it does sound as though the employee was wildly underprepared for the change in relationship.

    I’ve made the switch in Australia both ways, and it does take a mindset change on both sides. The employee has to flip to “this is my business now, I need to sell my services and take responsibility for running my side”, while the employer needs to be on board with that change, plus willing to be clear about what they’re buying and what they’re not.

    But we also have a lot of sham contractors and hourly casual employees where the freedom from obligation is entirely on the ’employer’ side. Doesn’t sound as though that was what happened here, but it might have been useful for the LW to look for ways to let the employee back down and remain an employee while they worked this through.

    1. Raida*

      You’re so on point.

      A Boss becoming a Client needs to understand, without getting offended, that “other duties as assigned” and “all pull together this week with long hours” and “just cover for Jo this week while they’re on holiday” are not on the table for a Contractor with a specified scope/services on offer.

      I’ve seen an ex-boss get all huffy and whingy over this and he had to be told to pull his head in by his GM because it’s no longer “That’s how the team runs.” – it’s “Your unprofessional behaviour is creating a Risk to the Business, if you cannot be trusted to manage this contract it’ll be moved to someone who can.”
      That was a real slap in the face to him, because he’d just… not thought it through!

    2. Ellis Bell*

      I think there was a lot of misinformation in the making of Sarah’s decision and probably a lot of remorse afterwards. I bet that’s a big part of OP’s frustration here; they lost a valued employee and they’re not sure the move even benefitted the employee either! I’m sure OP wonders if they could have outlined this for Sarah better and persuaded them? Possibly OP could have kept conflict down by just nopeing out on the proposal, thereby ending the working relationship sooner and more cleanly, while letting Sarah know that she was always welcome to come back if it didn’t work out. However, I think Sarah was pretty hellbent on getting her own business up and running. I think being a contractor was so central to her plan, that she was probably deaf to reason and emotional about any refusals to go along with her proposal.

      1. Bee*

        Yeah, I kind of get the sense that if Sarah had been moving on for normal business reasons – wanting to work for a larger company, wanting to do a different kind of work, moving to another state, going back to school, just generally needing a change, etc – then the OP would’ve been sad to lose her but would not have felt betrayed in the same way. But this situation went so badly that it ruined a professional relationship AND a personal relationship, and all for a completely ill-considered reason. It’s very normal to wonder what you could’ve done differently to avoid this!

  17. Saturday Manager*

    My read was that the employee leaned on OP to go along with the change, possibly manipulating the situation, and then didn’t perform well under the new arrangement. I wonder if there were other instances of this kind of behavior that the OP smoothed over or overlooked as the employee learned and developed. It’s easy to get too wrapped up with an employee, absorbing their mistakes, thinking you can coach them to be someone they’re not (I’ve done it). Eventually the employee just has to be who they really are – for good or for ill. Maybe OP overlooked too much, and did too much for the employee, and this made it more unpleasant, surprising and frustrating when the employee/contractor failed in the new role.

    1. Elsajeni*

      I think this factor, that the OP was going along with a plan they didn’t really think would work, is probably a big part of their reaction — they’re frustrated with Sarah for insisting “no, no, this will totally work!” even as it became clear that it wasn’t working out the way either of them wanted, and also frustrated with themselves for going against their own better judgment and then — just like they knew would happen! — it didn’t work out.

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