How to Prepare for Difficult Conversations

    Two people sitting at a table and talking in front of a window with a cityscape outside

    Difficult conversations are difficult in large part because so many parts of ourselves get tied up into them. Our emotions, our sense of self, our ego, our sense of competence, our sense of being loved—all of that can be challenged in a difficult conversation. One of the best ways to prepare for difficult conversations is to sort out these different parts of ourselves first, before we jump into the fray.

    The Three “Underlying Conversations” in Every Difficult Conversation

    The work of Douglas Stone, Sheila Heen, and Bruce Patton (of the Harvard Negotiation Project) teaches us that in every difficult conversation, there are actually three underlying conversations going on. Fully understanding the three levels of conversation can help us to avoid ineffective communication or misunderstanding.

    1) The content of the conversation.

    What actually happened? Are we perceiving an attack from having done something wrong? The part of ourselves that’s most often challenged by the content of these conversations is our competence.

    2) The emotions involved.

    What am I feeling during this conversation? Am I being attacked – not the work itself, but myself as a person? The part of ourselves most challenged by the emotions of a conversation is our sense of being a good person.

    3) The identity conversation.

    Who or what am I, if what the other person says (or the underlying assumptions behind their words) are true? The part of ourselves most challenged by the identity conversation is our sense of being worthy of love.

    When these three conversations get muddled into one, it’s easy to get hurt or defensive. Before going into a difficult conversation, it helps to separate these various parts of yourself. We’ll cover a specific meditation to do so in a moment. But first, let’s talk about preparing to go into a difficult conversation.

    Before Initiating a Difficult Conversation

    Use this process to help mentally prepare for a difficult conversation.

    • Examine what’s really driving your desire to have the conversation. Is it productive—in that it would actually solve a problem, or move a project forward? Or is it reactionary—a desire to show that you were right after all, or to hurt someone who hurt you? A few minutes of meditation can help dissipate the emotional charge, so you can see what’s driving your motivations more clearly.
    • Talk to a few people you trust. Mentors, team members, and so on. The first few times you talk about an emotionally charged topic are the hardest. Once you’ve talked about it a few times, much of the emotions dissipates—allowing you to have that conversation in a clear headed manner. Talking to a third party will also allow you to get an objective perspective from them, instead of seeing it just from your point of view. Finally, talking to a neutral third party allows you to practice what you’re going to say.
    Photo by Christina @</a> on Unsplash
    Photo by Christina @ on Unsplash

    Preparing for the Difficult Conversation

    This exercise will help you sort out the different internal conversations that go along with a difficult conversation. Identifying these various parts will help you have the conversation in a much more objective and compassionate manner—without being defensive or angry.

    1. Start by thinking of a specific conversation you’re about to have. Or, for practice, you can use a difficult or emotionally charged conversation you’ve had recently.
    2. Run through these three separate internal conversations separately. Ideally, speak them out loud, write them down or run through them with a friend.
      • What actually happened? Do I feel like my sense of competence is being questioned as a result of what happened?
      • What emotions are involved? Do I feel like whether or not I’m a good person is being called into question?
      • Who am I if what the other person says (or assumes) is true?  Do I feel like this makes me less worthy of love?
    3. Repeat the exercise from the other person’s point of view. How are they experiencing each of these questions?

    Running through this exercise before a difficult conversation will help you remove any emotional baggage attached to the conversation. It’ll also help you see things from the other person’s view—and see why they might be feeling defensive. It’ll allow you to approach the conversation from a place of compassion and connection, rather than accusation or defensiveness.


    Stone, D., Patton, B., & Heen, S. (2011). Difficult conversations how to discuss what matters most. Portfolio Penguin.