The Buddha explained how we can know when speech is skillful:
“Monks, a statement endowed with five factors is well-spoken, not ill-spoken. It is blameless and unfaulted by knowledgeable people. Which five? It is spoken at the right time. It is spoken in truth. It is spoken affectionately. It is spoken beneficially. It is spoken with a mind of good-will” (Anguttara, V.98).
So, the characteristics of skillful speech are timeliness, truthfulness, compassion, that it is beneficial and is generated with good will. In some situations, it is difficult to know whether we are exercising skillful speech (or silence). When I am puzzled on this issue, I ask myself, “What is the intention in this situation?” If I am satisfied that my intention falls into one of the Buddha’s five factors, I don’t obsess on whether or not I said the “right thing.” It’s also easier to let go of an attachment to results, since I cannot control others’ reactions to what I have to say.
In working with this step on the path, I have noticed that I often have a desire to be understood (agreement with my point of view is also nice). Perhaps you have noticed this subtle attachment in your own practice. How often does the desire to be “right” govern how we speak? How often do we feel the need to defend our position? What is the attachment here?