How to have difficult conversations

by Andrew Wien


Posted on October 10, 2020


How to have difficult conversations
​Struggle with difficult conversations? Here is a summary of the best book out there, Difficult Conversations, by Harvard Law professors and members of the Harvard Negotiation Project.

A difficult conversation is anything you find it hard to talk about. You can get better with practice. This will make your life better.

Every difficult conversation has three separate conversations happening at the same time:
  1. What happened
  2. How it made you feel
  3. What’s at stake for you in terms of your identity.

​What happened: 
You and the other person both have a story around what happened. Rather than arguing, explore both perspectives. Two tricks to keep you from arguing are (1) disentangle impact from intent (you know their impact, but what was their intention?) and (2) shift from blame to contribution (rather than it’s their fault, ask how did both of us each contribute to the problem?).

How it made you feel: unexpressed feelings will affect either the conversation or the relationship long term. Recognize that there is likely a bundle of feelings associated with this conversation. That’s okay. Name them, then communicate them without blame.

Your identity: difficult conversations threaten your identity, typically in one of three ways:
  1. Am I competent?
  2. Am I a good person?
  3. Am I worthy of love?

First, identify what’s at stake for you. Next, ground your identity by taking a broader perspective of who you are—this conversation does not define you.

To have a difficult conversation, follow five steps.

Step 1: Prepare by unpacking the three conversations

Step 2: Clarify your purpose (i.e. what do you really want?). Then decide whether you should have the conversation or let it go. It’s more effective to let it go if the real conflict is inside of you, there is a better way to address the issue than talking about it, or your purpose does not make sense (e.g. change who the other person is)

Step 3: Start from the 3rd story. Describe the situation as a difference between your perspective and their perspective. Share your purpose. Then ask for help exploring the topic together and reaching a conclusion.

Step 4: Explore both your perspective and their perspective. Both sides are important. Listen to them by asking questions, paraphrasing what you’ve heard, and acknowledging how they feel. Communicate your perspective as a perspective, not a truth. Say what you mean rather than making them guess.

Step 5: Problem solve. Reframe to move past roadblocks (e.g. “It’s your fault” can be countered with “We have both contributed to the problem. My contribution was X. What was your contribution?”). If the conversation goes off the rails, name the dynamic and make it explicit. (e.g. I’ve tried to say what I’ve been thinking 3 times now, and each time you’ve started talking over me. I don’t know if you’re aware…)

What conversation will you apply this framework to?

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