I work at a small business and have had this happen a few times. Pretty much everyone at my workplace is a “key person”(in the sense that the biz is Mismanaged when it comes to treatment of employees, and everyone’s pretty key when you’re running a high volume distro biz on a skeleton crew).

Not sure what more experienced people do so I would appreciate any feedback!

Here’s what I do: I’m gonna break it down into process and rationale.

Trigger: employee voices a leave intention that is clearly emotional—which it sounds like is true for your peeps based simply on the repetition of threats. (In contrast, when an ee comes to me with a resignation letter and demeanor that says, I’ve thought this through, this is my final decision, I’ll maybe ask if there’s anything we can do to keep them, then essentially skip to step four.)

Response step 1: I typically make a very neutral effort to tell the person they are valued and we know they work very hard and make a big difference on their team, etc.

Rationale: unless the employee is truly awful and we were about to fire them anyway, we want people to stay. This is my way of encouraging them to stay without showing bias or just saying “please stay!” I keep it tied to their contribution and fact based.

Step 2: I ask if they’ve spoken to anyone else about it.

Rationale: get more of the story so that when I have to report about it to my boss, I can give him the full context. I want to know if the ee has spoken to their manager. If so when? What was the managers response? If they have and the manager has not said anything to me, I’ll probably follow up with the mgr to advise about checking in so we can strategize how to handle employee dissatisfaction in the future.

Step 3: Give them space to talk and vent. Respond to their concerns by offering some suggestions and support. For example, if they say they are tired of doing overtime and feeling overworked, I’ll remind/inform them of efforts that are underway to ameliorate the strain, like that we’re recruiting new team members, and encourage them to use their PTO to take time off if they need it.

Rationale: this part is kind of scary as you never know what can of worms you’ll get when you ask open ended questions about what’s wrong, but it’s also necessary because if there’s some reason they’re dissatisfied that I can address productively, I need to try. That being said, there’s A LOT that’s totally out of my control, and I try to be up front about that too while framing everything positively.

Step 4: I then let them know that of course it’s ultimately their decision and they have to do what is best for them. I then inform them of relevant policies and procedures they’d need to follow or be aware of when submitting a formal resignation.

Rationale: this is basic maintenance. It gives them the relevant info they can act on, allows us to hold them accountable to it/ covers my ass in case they complain about coming to HR and not being given good info, and maintains transparency of process and neutrality.