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Aggggh. This could all be solved if your employees would stop being so passive about it! If they’d simply tell Jenny they can’t drive her anymore, the problem would be solved.

But they’re not — and since you’re actually losing employees over it, something that shouldn’t need to be your business is becoming your business.

To be clear, there are a lot of ways this could play out that wouldn’t be your business. If Jenny were just asking for occasional rides and people were mildly annoyed but doing it anyway … not really your business. But you’ve had employees quit over it.

I also wouldn’t be surprised if over time, a cultural expectation has built up on your team that driving Jenny around is “what we do here” — and so people who would like to tell Jenny no worry they’re expected to do it anyway. Some of them might worry about how it will affect their relationship with Jenny at work, or even their relationships with other coworkers if their refusal to drive her means someone else feels obligated to drive her in their place. So again: your business.

But I can see why you’re struggling with it, since it’s outside-of-work behavior that your employees are agreeing to. Keep in mind, though, that there are times when behavior outside of work falls into your purview: for example, if an employee kept showing up to outside-work social events and insulting the coworkers who were there, that would be your business because it would affect the dynamics on your team. Or, for an example that’s closer to your situation, what if you had an employee who was constantly nagging coworkers to buy her dinner and they didn’t want to do it but felt obligated to help her out, and some people were starting to resign rather than continue to fund her meals? In both those situations, although the behavior was outside of work, it would be affecting your team dynamics and so you’d have standing to intervene.

There are limits to this, of course. If two of your employees used to be outside-of-work friends and had a falling-out, it wouldn’t be appropriate for you to get involved other than ensuring they were treating each other civilly at work. But when things come into work, they’re your business. And in this case, with people quitting over the situation, that bar has been met.

Ideally, you could just talk to the people driving Jenny and give them your explicit encouragement and permission to turn down her ride requests. But it sounds like you’ve done that and it hasn’t changed anything. Maybe that’s because these employees are people-pleasers or afraid to be assertive, which can become extra potent if it intersects with any feeling of “this is what the team does.” But since talking to them hasn’t worked, I’m hesitant to rely on trying more of that.

Because of that, I think you’ll have to talk to Jenny and say something like: “I need you to figure out transportation to and from work that doesn’t involve relying on your coworkers. I know on your end it must look like people are driving you happily, but what I’m hearing on my end is that people feel pressured to help but would like to stop, and it’s affecting the dynamics on the team. I understand this has been your set-up for a long time, so I don’t expect you to change it overnight, but I do need you to have another system in place one month from now.”

She will probably push back, saying people are happy to do it and they’d say no if they didn’t want to. To that you can say, “Unfortunately, we’ve had people quit over this and I can’t continue having it impact the team that way. You do need to find your own transportation to and from work.”

In theory you should add, “Obviously an occasional ride when you’re in a pinch is fine — we’d all do that for each other. But your coworkers can’t be your default plan for getting here and home.” But given the high danger that Jenny will take that as license to continue to ask for rides most of the time, I’d probably leave it out for now.

After you have that conversation, it’s worth talking to the ride-providing coworkers again, letting them know you’ve had this conversation, and saying you need them to do their part by being clear with Jenny that they can’t continue to drive her.

From there, you’ll need to stay pretty actively involved to make sure that Jenny really does stop leaning on colleagues for constant rides; this is entrenched enough that it’s likely to take fairly active involvement from you (possibly ongoing for a while) to ensure she actually lets up on people.

Is this a weird amount of involvement to have in an employee’s transportation and other employees’ favor-providing? Yes! It absolutely is. But it’s at the point that you’ve lost multiple employees over it, so you’ve got to intervene.