The problem with having a sense of humor is often that people you use it on aren’t in a very good mood.

Holtz is pointing to the situational nature of humor: a joke or light remark isn’t inherently “good” or “bad,” but lands differently depending on the listener’s emotional state. The line also implies a leadership lesson—especially relevant to coaches and managers—about reading the room. Humor can build rapport, relieve pressure, and humanize authority, but it can also feel dismissive or insensitive when someone is stressed, angry, or discouraged. The quote therefore frames humor as a tool that requires timing and empathy, not just wit, and suggests that social intelligence matters as much as comedic intent.