When it comes to the question asked in this piece's headline, it would seem to be a pretty binary situation: Either you tell them you're selling or you wait until you're in your helicopter taking off with the duffel bags of money and let them figure it out for themselves.
Intuit Small Business Blog further breaks down the two options you have, and there are gradations to which you can do either:
Revealing your plans to sell doesn’t mean you have to disclose everything about the process; the people who work for you don’t need a step-by-step description of what’s going on behind the scenes. Do explain the reasons behind your decision and what you aim to achieve with a successful sale. Manage employees’ expectations, too: Tell them you will provide more information when you’ve completed the transaction — and that, up to that point, they should disregard any rumors or gossip about a sale.
Or, if you don't want to tell everyone and potentially demoralize or cause a panic, you can tell a handful of "trusted employees." They can help keep things quiet until everything is finalized. But that also sounds a lot like the other approach: not telling them.
If you opt to not tell them, you should wait until the sale is finalized. And there is ample reason to do this: "Employees with advance knowledge of a sale may tell customers about it," which can affect customer service, the company's rep and loads of other ripples you couldn't possibly predict.
So, if you are fortunate enough to be able to cash out and head onto your next venture, give this piece a read. If nothing else, it's a good examination on office communication – which is never a bad thing. Except in those cases when it is.
David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a comedy-writing instructor for Second City. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. When not playing video games for work he's thinking of dashing out to Chicago Diner, Pizano's, or Yummy Yummy. His first career aspirations were to be a game-show host.