While difficult conversations are important to have, it’s crucial to consider when to have a conversation. Not every situation is going to call for the same prescription: “the specifics of each situation are different, there is no simple rule” (132). The best advice is to work through the three conversations and to discern what’s at play.

In addition, there are three questions to help ascertain if a conversation is worth initiating. The first question to ask is whether the real conflict is internal, rather than with the other person—“a conversation focused on the interaction isn’t going to be very illuminating or productive, at least until you’ve had a longer conversation with yourself” (133). The second question to ask is whether there’s a better way to approach the issue rather than having a conversation; perhaps there’s a different action that can be taken that will solve the problem and allow tension to disappear naturally.

Finally, one must ask whether there is a logical purpose to the proposed conversation; one can influence another, but it is impossible to force one to change their mind, or to force one to change a specific behavior. The question is will a conversation likely to lead to self-reflection in the other: “The

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