Guide to Difficult Conversations

Ten Tips for Challenging Conversations

  1. Reflect

    Before you enter a difficult conversation, check in with yourself. Take a breath. You want to enter the conversation feeling calm and ready.

  2. Be ready to press pause

    These conversations can be challenging and painful. Know your limits, and have a plan for how to press “pause” on the conversation if it becomes too challenging or uncomfortable for you. If you feel yourself getting angry or feeling hurt, you can suggest that you take a moment and decide whether you want to continue the conversation or take a break from it.

  3. Open the conversation

    Before diving into the content of the conversation, explain why you want to have the conversation. If the conversation is with someone you know and care about, you can affirm how much you care about them and what you appreciate about them. This can put people in a less defensive stance. Recognize that you have deep disagreements, and explain why you think it’s important to try to talk about hard subjects together. This can help set the stage for sticking with it even when things get tough.

  4. Set expectations

    If you want to set some expectations or ground rules, do so. For example, you can say “it’s really hard for me to stay engaged in a conversation if we start to raise our voices, so can we agree to pause if we start to raise our voices?”

  5. Think about who you’re talking to

    What do you know about the person you’re talking to? How do they see themselves, and what matters to them in their life? As you have the conversation, try to connect your experiences and ideas to their values and experiences.

  6. Listen first, then respond

    As you’re having the conversation, keep trying to learn about the person you’re talking to and what matters to them, even when they’re saying things you disagree with. This will help you figure out what new information, stories, and connections you can share with them to help them understand your point of view.

  7. When possible, share personal experiences and stories

    Try to move away from common arguments and scripts – you’ll just fall on opposite sides and won’t be able to open new understandings. Arguing about facts and beliefs can also lead people to become defensive. On the other hand, stories and personal experiences that you can connect to their values and experiences can be very powerful.

  8. Avoid blaming, shaming, and name-calling

    We all want to believe that we are good people. Blaming, shaming, or calling someone names will likely only push them into a defensive corner. Instead of using names and shaming someone, try to help them understand and care about the impact of their actions, without having to see themselves as inherently bad. This will make them more open to change.

  9. Affirm emotions, challenge conclusions

    While it may be tempting to challenge people’s emotions (e.g., to tell them that they shouldn’t feel scared, angry, etc.), this will likely make them less able to hear what you’re saying. Instead, try to recognize and show that you understand the emotions people feel even though you may be challenging the meaning or conclusions that they attach to those emotions.

  10. Think of it as a process

    A single conversation can have a big impact. But it can also take time. If one conversation doesn’t go as planned, think about what you learned from it that you can use for the next one. Each conversation you have should build on the last.