To me, it sounds more like Brent was looking for a way out, so he made up a reason ("my boss is such a micromanager") that he could use both in interviews and to your company to explain why he's leaving.

I'm flabbergasted that someone used the word 'flabbergasted'.

Brent was a lost cause far before this happened. You will likely never know the "real" reason he left, as Brent has even convinced himself of the above. I can't say unequivocally that he's right or wrong, but I have to give you significant credit for objectively reviewing your own performance from every angle available to you. If nothing else, that kind of self-review has helped you, I'm sure. Go forward with the knowledge that your effort was worth it, even if Brent wasn't salvaged.

IANAL, but IMO your boss and his friend shouldn't be having these conversations. A bunch of Silicon Valley companies got in trouble for having a tacit non-compete agreement.

Did Brent indicate specifically what actions of your made him feel micromanaged? Like many things, micromanagement is in the eye of the beholder. If Brent feels micromanaged to the extent that he wants to leave, then you'd be wasting your time trying to explain why he actually isn't being managed that way. "he can't stand to work under me any longer" probably has nothing to do with being micromanaged.

@JoeStrazzere Brent gave my boss specific examples, but I wasn't in the room at the time. We have a meeting scheduled for next Monday to all sit down together and see what, if anything can be done to solve the problem. Until then unfortunately I can't provide any specifics beyond my own speculation.

@Lumberjack - I think learning about these specifics may help you in the future. But I suspect it's a complete waste of time regarding Brent.

If I had a micro-manager boss who asked me if they micro-managed, I might say no as well, for a variety of reasons. That data isn't particularly useful.

@AndrewWhatever I agree. I might say no too.

Surely now that Brent is leaving and has cited your management style, you can talk to him about it? If you have a meeting after the weekend at which he will being evidence, you could approach him after that meeting and ask "Do you really feel like that?" Once he's unburdened himself to your manager, he may well come clean about "Well, no, but I needed an excuse".

@kevincline it took me a Google to figure our 'IANAL' wasn't what I though it was...

@MarkSegal You are not the only one: meta.workplace.stackexchange.com/questions/3689/…

You can't just accuse someone of being a micromanager and not have a bunch of complaints and stories to back that up. Your boss should ask Brent for these stories. If Brent cannot give concrete examples, he's full of it. If he can, then you know what you need to work on, or if his expectations are unreasonable. (edit, oh, I just saw your comment that he DID supposedly give examples, I would be curious to know what they were)

"We have a meeting ...Monday ... to solve the problem." A some of the answers imply, if you want to spend Monday constructively, call in sick and do some real work at home. Brent is a lost cause IMO. At worst, following the meeting he will consider himself to have been appointed as your personal management style coach for the indefinite future - and I assume you don't want that! If your boss has anything constructive to say to you after Brent has left the company, take that dialog forward if and when it happens.

"When my boss called me in to talk about it, I was told keep it to myself and not let Brent know that I was aware of his concerns." - why? What reason did your boss give for this secrecy?

@JoeStrazzere My boss wanted to be present to mediate the discussion. We have a meeting scheduled for Monday.