We Have to Talk: A Checklist for Difficult Conversations


Think of a conversation you’ve been putting off. Got it? Great. Then let’s go.

There are dozens of books on the topic of difficult, crucial, challenging, important (you get the idea) kinds of conversations (at the end of the articles, I list several). Those times when you know you should talk to someone, but you don’t. Maybe you’ve tried before and it went badly. Or maybe you fear that talking will only make the situation worse. Still, there’s a feeling of being stuck, and you’d like to free up that stuck energy for more useful purposes.

What you have here is a brief synopsis of best-practice strategies: a checklist of action items to think about before going into the conversation; some useful concepts to practice during the conversation; and some tips and suggestions to help your energy stay focused and flowing, including possible conversational openings.

You’ll notice one key theme throughout: You have more power than you think.

Preparing for the Conversation

Before going into the conversation, ask yourself some questions:

  1. What is your purpose for having the conversation? What do you hope to accomplish? What would be an ideal outcome? Watch for hidden purposes. You may think you have honorable goals, like educating an employee or increasing connection with your teen, only to notice that your language is excessively critical or condescending. You think you want to support, but you end up punishing. Some purposes are more useful than others. Work on yourself so that you enter the conversation with a supportive purpose.
  2. What assumptions are you making about this person’s intentions?You may feel intimidated, belittled, ignored, disrespected, or marginalized, but be cautious about assuming that that was the other person’s intention. Impact does not necessarily equal intent.
  3. .

  4. What “buttons” of yours are being pushed? Are you more emotional than the situation warrants? Take a look at your “backstory,” as they say in the movies. What personal history is being triggered? You may still have the conversation, but you’ll go into it knowing that some of the heightened emotional state has to do with you.
  5. How is your attitude toward the conversation influencing your perception of it? If you think it is going to be horribly difficult, it probably will be. If you truly believe that whatever happens, some good will come of it, that will likely be the case. Try to adjust your attitude for maximum effectiveness.
  6. Who is the “opponent”? What might he be thinking about this situation? Is he aware of the problem? If so, how do you think he perceives it? What are his needs and fears? What solution do you think he would suggest? Begin to reframe the opponent as a partner.
  7. What are your needs and fears? Are there any common concerns? Could there be?
  8. How have you contributed to the problem? How has the other person?

Four Steps to a Successful Outcome

The majority of the work in any conflict conversation is work you do on yourself. No matter how well the conversation begins, you’ll need to stay in charge of yourself, your purpose, and your emotional energy. Breathe, center, and continue to notice when you become off-center—and choose to return again. This is where your power lies. By choosing the calm, centered state, you’ll help your opponent/partner to be more centered, too. Centering is not a step; centering is how you are as you take the steps. (For more on centering, see The Magic of Conflict and the “FAQs About Conflict” listed at the end of the article.)

Step #1: Inquiry

Cultivate an attitude of discovery and curiosity. Pretend you don’t know anything (you really don’t), and try to learn as much as possible about your opponent/partner and her point of view. Pretend you’re entertaining a visitor from another planet, and find out how things look on that planet, how certain events affect the other person, and what the values and priorities are there.

If your partner really was from another planet, you’d be watching her body language and listening for the unspoken energy as well. Do that here. What does she really want? What is she not saying?

Let her talk until she is finished. Don’t interrupt except to acknowledge. Whatever you hear, don’t take it personally. It’s not really about you. Try to learn as much as you can in this phase of the conversation. You’ll get your turn, but don’t rush it.

Step #2: Acknowledgment

Acknowledgment means showing that you’ve heard and understood. Try to understand the other person so well you can make his argument for him. Then do it. Explain back to him what you think he’s really going for. Guess at his hopes and honor his position. He won’t change unless he sees that you see where he stands. Then he might. No guarantees.

Acknowledge whatever you can, including your own defensiveness if it comes up. It’s fine; it just is. You can decide later how to address it. For example, in an argument with a friend, I said: “I notice I’m becoming defensive, and I think it’s because your voice just got louder and sounded angry. I just want to talk about this topic. I’m not trying to persuade you in either direction.” The acknowledgment helped him (and me) to recenter.

Acknowledgment can be difficult if we associate it with agreement. Keep them separate. My saying, “This sounds really important to you” doesn’t mean I’m going to go along with your decision.

Step #3: Advocacy

When you sense that your opponent has expressed all her energy on the topic, it’s your turn. What can you see from your perspective that she has missed? Help clarify your position without minimizing hers. For example, “From what you’ve told me, I can see how you came to the conclusion that I’m not a team player. And I think I am. When I introduce problems with a project, I’m thinking about its long-term success. I don’t mean to be a critic, though perhaps I sound like one. Maybe we can talk about how to address these issues so that my intention is clear.”

Step #4: Problem-Solving

Now you’re ready to begin building solutions. Brainstorming and continued inquiry are useful. Ask your opponent/partner what he thinks would work. Whatever he says, find something that you like and build on it. If the conversation becomes adversarial, go back to inquiry. Asking for the other’s point of view usually creates safety, and he’ll be more willing to engage. If you’ve been successful in centering, adjusting your attitude, and engaging with inquiry and useful purpose, building sustainable solutions will be easy.

Practice, Practice, Practice

The art of conversation is like any art—with continued practice, you acquire skill and ease. Here are some additional hints:

  • A successful outcome will depend on two things: how you are and what you say. How you are (centered, supportive, curious, problem-solving) will greatly influence what you say.
  • Acknowledge emotional energy— yours and your opponent/partner’s— and direct it toward a useful purpose.
  • Know and return to your purpose at difficult moments.
  • Don’t take verbal attacks personally. Help your opponent/partner come back to center.
  • Don’t assume your opponent/partner can see things from your point of view.
  • Practice the conversation with a friend before holding the real one.
  • Mentally rehearse the conversation.

See various possibilities and visualize yourself handling them with ease. Envision the outcome you’re hoping for.

How Do I Begin?

In my workshops, a common question is “How do I begin the conversation?” Here are a few conversation openers I’ve picked up over the years—and used many times!

  • I have something I’d like to discuss with you that I think will help us work together more effectively.
  • I’d like to talk about ___________ with you, but first I’d like to get your point of view.
  • I need your help with what just happened. Do you have a few minutes to talk?
  • I need your help with something. Can we talk about it (soon)? If the person says, “Sure, let me get back to you,” follow up.
  • I think we have different perceptions about ___________. I’d like to hear your thinking on this.
  • I’d like to talk about ___________. I think we may have different ideas on how to ___________.
  • I’d like to see if we might reach a better understanding about ________. I really want to hear your feelings about this and share my perspective as well.

Write a possible opening for your conversation here: ______________________________ ______________________________ ______________________________ ______________________________ ______________________________ ______________________________ ______________________________ ______________________________ ______________________________

Good luck!

Judy Ringer is a conflict and communication skills trainer, black belt in aikido, and sole owner of Power & Presence Training and Portsmouth Aikido. To sign up for free tips and articles, visit http://www. JudyRinger.com.

For Further Reading

The Magic of Conflict: Turning a Life of Work into a Work of Art (Touchstone, 1998), by Thomas F. Crum (www.aikiworks.com)

Difficult Conversations: How to Discuss What Matters Most (Penguin Putnam, 2000), by Douglas Stone, Bruce Patton, and Sheila Heen (www.triadcgi.com)

Crucial Conversations: Tools for Talking When Stakes Are High (McGraw-Hill, 2002), by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler (www.crucialconversations.com)

FAQs about Conflict, by Judy Ringer (www.judyringer.com)

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