I've personally been instructed to fire two people who reported to me, who had been coworkers before organizational changes and who were both nominally friends.

I've personally been instructed to fire two people who reported to me, who had been coworkers before organizational changes and who were both nominally friends. There is no easy way to do it even if it's justified. The worst part is honestly what happens after - the person may have a hard time finding another job, and even if the separation is justified it's still kind of 'on you' for letting them go; a lot of people would assert that it's on you anyway for not making them better. I've been through a 'silent layoff' at a startup, wherein most of the staff just stopped getting paid. We were funded by PE; the leadup to the separation was several weeks of accusations back and forth re: lying about available funds vs. mismanagement of granted funds. The company offered no severance and fought my unemployment claim. I was kind of relieved when it was over, but I would not recommend handling it this way unless you just don't care; it's been years but I still basically hate everyone involved. I've since survived 3-4 rounds of layoffs where I'm working now. We've had it most of the ways you can have it: mass meeting, one on one w/ HR rep, nominated out-of-dept managers shepherding individuals out of the building, rent-a-cops in the office, etc. In all but one case, the departing employees were given a couple of paychecks severance + placement assistance and IIRC in at least one case remaining employees were offered grief counseling. I don't think I could ever enjoy being laid off, but IMO the right way in a multi-person separation is to have one meeting with everyone, be honest about what's going on, and give them whatever you can to soften the blow. Unless there's a good chance your funding situation is about to improve, this means you should do it a little earlier than you think you need to so that last x days/weeks of salary can be severance instead; IMO people are not going to be significantly happier about being laid off if it happens 2 weeks later. If you've got contacts at other places and you can give references or help place, do that. You probably don't need police to escort people out, but you should get the departing employees out of the building w/ relevant credentials and badges revoked asap. Don't let people mill around, it exposes you and gives them more opportunity to vent in ways both of you will regret; I've seen where people were let go, then went and deleted things from file servers or otherwise destroyed property prior to leaving the building.