It seems like such arbitrary conditions you set in order ...wait a minute, I just noticed the website is "growthsensei.com", that's like Guru level 88?
I read some of the comments about employee passiveness. Sometimes it's tough for an employee to put themselves on the spot like that. What if the conversation doesn't go the 'right' way?
That mock monologue is actually really spot on. I just recently left our bootstrapped startup and had a pre-emotive conversation shortly before doing so. It played out just like that.
I shared this link on HN already but since its so relavent here it is again. I wrote about why I still left. But didn't write about the conversation I had. And you hit it on the head. http://mustefa.com/looking-back-at-my-ux-career-in-2012/
Ignore baconface. Great review, it's interesting to see things from a developers point of view. I was hoping to see more of what you learned in design. I might make some speaker deck presentations myself.