Rotman Management

Mastering Difficult Conversations

How do you define a difficult conversation?

Douglas Stone: A difficult conversation is anything that is hard for someone to talk about. It can range from asking your boss for a raise to providing negative feedback to a subordinate to complaining to your neighbour about his dog barking. These conversations are particularly tricky because there is often a gap between what people are really thinking and what they say.

Of course, whether something is difficult to discuss (or not) is subjective, but these conversations tend to share some key characteristics. One is that there is usually something important at stake. As a result, we might be concerned that engaging in the conversation will negatively impact the relationship. In addition, there are often questions of identity on the line. We all view ourselves in certain way: ‘I am a nice person’ or ‘I am a hard worker’. When we engage in a difficult conversation, there is the potential to receive feedback about how someone else sees us — which sometimes clashes with how we see ourselves. The conversations that feel the most difficult tend to be the ones that threaten our self-image.

You have said that very difficult conversation is actually three conversations. Please explain.

We have studied hundreds of these conversations, and it turns out that no matter what the subject, our thoughts and feelings fall into the same three categories or ‘conversations’. The first is the ‘what happened?’ conversation. Most difficult conversations involve disagreement about what happened or what happen. This is where we spend the most time in a difficult conversation, trying to figure out who is right, who meant what and who is to

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