Season 1, episode 10, "Haven"
Lesson: respect your employees' personal choices
This post is part of my ongoing quest to watch every episode of Star Trek: The Next Generation and pull one startup, entrepreneurship, tech, or investing lesson from each.
Out of nowhere, some dude shows up who Deanna Troi was supposedly engaged to in an arranged marriage situation years before. And for some reason that is never explained, Troi is set on upholding this promise despite it being forever ago, she doesn't know this guy, she has an important job on the Enterprise, their families don't get along, she seems progressive otherwise, she's obviously still got a thing for Riker and vice versa, etc. It makes zero sense to anyone, including the viewers and Captain Picard. At the last minute, her husband-to-be (Wyatt) leaves her to go be with the literal woman of his dreams who also happens to be some kind of leper. I'm not making this up. Thus Troi is free to stay on the Enterprise and keep doing her job.
Although Picard clearly didn't want to lose a crew member as talented and valuable as Troi, he never questioned her personal beliefs or pushed her to stay. He supported her choice. If one of your star employees wants to get married and move away or go on parental leave or otherwise leave for personal reasons, begging them to stay won't change anything and risks looking desperate. The right approach is to make them understand how valued they are, respect their choice, and hope for the best. Maybe they won't end up leaving (like here), they'll come back later, or you can work out a flexible arrangement. You can never really know what issues your employees are balancing in their personal lives.
IMDb gave this one a 6.3/10 rating and I can see why. Oof. At least there was a cameo by the guy who played Lurch in the Addams Family and the fireman in Twin Peaks where he got drunk and repeatedly banged a gong.