As a special case of not over-optimizing things, I want to point out that an optimizing approach can have a bunch of subtle negative effects in social contexts. The slogan is something like "optimizers make bad friends" ... people don't like being treated as a means rather than an end, and if they get the vibe from social interactions that you're trying to steer them into something, then they may react badly.
Here I'm referring to things like:
... where it's not clear that the other side are willing collaborators in your social objectives.
So I don't mean to include optimizing for things like:
I think that people (especially smart people) are often pretty good at getting a vibe that someone is trying to steer them into something (even from relatively little data). When people do notice, it's often correct for them to treat you as adversarial and penalize you for this. This is for two reasons:
Correspondingly, I think that we should be especially cautious of optimizing in social contexts to try to get particular responses out of people whom we hope will be our friends/allies. (This is importantly relevant for community-building work.)
I tend to over-optimize in social contexts and am lucky to have friends who understand my vagaries. They do consider it somewhat disturbing though that I seem to try to actively maximize the amount of total benefit we both get out of every conversation, as if it's a kind of job, but I have a hard time stopping myself from thinking that way.