How to Handle Tough Conversations


Tough challenges aren’t going away. But they are often very difficult to talk about — leaving us anxious, unsure, frustrated, or angry.

What can be done? Doug Stone, co-author of Difficult Conversations: How to Discuss What Matters Most, says that in order to deal effectively with awkward, tense, or challenging conversations, we first need to understand the common mistakes we make — and then take 5 steps for tackling tough conversations.

Working at the Harvard Negotiation Project with thousands of people, Stone and his colleagues found that we often make 3 major errors in our conversations:

We assume we know all we need to know to understand and explain a situation.

We hide our feelings — or let them loose in ways we later regret.

We ignore who we are, acting as if our identity is separate from the issues.

Avoiding these mistakes isn’t easy. “The key is to shift your thinking from I need to explain myself or deliver a message to I need to listen and learn more about what is going on,” Stone says. Here’s how to tackle tough conversations:


1. Prepare by Walking Through the “3 Conversations.” Every difficult conversation is really 3 conversations in one: the What Happened conversation, the Feelings conversation, and the Identity conversation.

“We need to understand what the people involved are thinking and feeling but not saying to each other,” Stone says. “In a difficult conversation, this is usually where the real action is.”

Before stepping into a discussion that you know will be challenging, ask yourself these questions:

Sort out what happened. How do you see the situation? Where does your story come from (information, past experiences, rules)? What do you think you know about the other person’s viewpoint? What impact has this situation had on you? What might their intentions have been? What have you each contributed to the problem?

Understand feelings. Explore your feelings and ask yourself, “What bundle of emotions am I experiencing?”

Ground your identity. How does this situation threaten you or have the potential to shake up your sense of identity? How do you see yourself (I’m the boss, I like competition, I’m loyal, I’m good at developing my people)? What do you need to accept in order to be better grounded?

2. Check Your Purposes and Decide Whether to Raise the Issue. What do you hope to accomplish by having this conversation? Do you want to prove a point or change the other person? How can you shift your stance to support learning, sharing, and problem-solving? Do you even need to raise the issue to achieve your purposes? Can you affect the problem by changing your contributions? If you don’t raise it, what can you do to help yourself let go?

3. Start from the “Third Story.” If you do decide to raise a difficult issue, don’t lead in with your view or story. Approach it as if a third, neutral person is looking on and leading the conversation. Describe the problem as the difference between your stories. Include both viewpoints as a legitimate part of the discussion. Share your purposes and let the other person know you are looking to sort out the situation together.

4. Explore Their Story and Yours. Listen to understand the other person’s perspective on what happened. Ask questions. Acknowledge the feelings behind the arguments and accusations. Paraphrase to see if you’ve got it. Try to unravel how the 2 of you got to this place. Share your own viewpoint, your past experiences, intentions, and feelings. And constantly reframe assumptions: from truth to perceptions, blame to contribution, and accusations to feelings.

5. Problem-Solve. Invent options that meet each side’s most important concerns and interests. Keep in mind that relationships that always go one way rarely last. Talk about how to keep communication open as you go forward.

Prevent the Conflict in the First Place

Difficult conversations often have to happen because better conversations didn’t.

People need to experience a 4:1 ratio of positive/encouraging interactions to challenging interactions in order to avoid feeling threatened or overly criticized. Increasing the amount of positive feedback and empowering conversations will strengthen engagement, promote psychological safety, and help avoid triggering a threat response.

Everyone in your organization can have more productive conversations when they genuinely listen in order to understand, ask the right questions, give feedback that challenges and supports, and establish accountability and next steps. With the right training and practice, leaders at any level can improve the quality of their conversations and feedback, creating a ripple effect throughout the workplace.