Dude I love the retro UI! ngl, the pairing of spinning wheels and character portraits sorta remind me of the dialog mechanic in Oblivion lol. I really like concept and I think it has alot more depth than what's typically expected of game jam submissions!
If I had a critique, I think a help screen or tutorial splash page would've cut out the trial and error process. But I'd love to see this concept lengthened, great job!
btw, if you got the time, it'd be cool if you could check out my game too! (it's kinda got a similar office/corporate theme)