I was at a company previously that had a liquidity event, and many of my colleagues (not me unfortunately) had very meaningful stock awards.

A lot of people discussed what they should do openly, and recognized the potential for the stock to go up later on- many defaulted to selling half of their holdings as soon as they could to put some cash in their pocket, and holding on to half for potential gains. Not super sophisticated, but it seemed like it made good sense to me.