How to Have Difficult Conversations

How to Have Difficult Conversations

By: Rifka Schonfeld, Director S.O.S (Strategies for Optimum Success)

Doesn’t it make sense that the same authors who wrote a book about accepting criticism are the ones who wrote a book about having difficult conversations? After all, what could be more difficult than a conversation in which you are accepting criticism? According to Douglas Stone, Bruce Patton, and Sheila Heen of the Harvard Negotiation Project, there are quite a few ways that conversations can be difficult. And, they even believe that you can plan for difficult conversations.


In fact, they lay out the tools to help you walk away from those conversations feeling calm and settled. In their book, Difficult Conversations: How to Discuss What Matters Most, the authors lay out wha they believe are the “three conversations” that happen within every difficult conversation.


What are those three conversations that are in every difficult conversation? According to Stone, Patton, and Heen they are the “what happened” conversation, the feelings conversation, and the identity conversation. Below, I’ve included the authors’ explanation of those conversations:


  1. The “What Happened?” Conversation. Most difficult conversations involve disagreement about what has happened or what should happen. Who said what and who did what? Who’s right, who meant what, and who’s to blame?
  2. The Feelings Conversation. Every difficult conversation also asks and answers questions about feelings. Are my feelings valid? Appropriate? Should I acknowledge or deny them, put them on the table or check them at the door? What do I do about the other person’s feelings? What if they are angry or hurt?
  3. The Identity Conversation. This is the conversation we each have with ourselves about what this situation means to us. We conduct an internal debate over whether this means we are competent or incompetent, a good person or bad, worthy of love or unlovable. What impact might it have on our self-image and self-esteem, our future and our well-being? Our answers to these questions determine in large part whether we feel “balanced” during the conversation, or whether we feel off-center and anxious.


It’s definitely not easy to simultaneously deal with all three of these conversations. What if you differ on how things really happened and therefore now you feel like you have done something wrong? What if you have hurt the other person’s feelings and they are angry and that makes you feel unlovable? Once we have gotten ourselves into these difficult situations, we need to work for a while to dig our way out of them, but the authors provide us with six tried and tested tools that can help us navigate difficult conversations before they start.


Tool #1: Make it Safe to Talk

If you know that a conversation could get difficult, begin by embracing a mutual purpose. In other words, let the other person know that you both want to resolve the issue at hand, and that you want to work together in the future.  In addition, let the other person know that you respect them and that this conversation is a sign of that. Hopefully, the other person will offer you mutual respect. A conversation that begins with mutual respect is much more likely to resolve positively.

If you feel that someone is misrepresenting your purpose or intent, use a contrasting statement. A contrasting statement says something like, “I am not trying to say that you were wrong, I am trying to say that I felt hurt when you ignored my suggestion.” This helps create a safe place and clarify misunderstandings.

Tool #2: Listen

Listening is a large part of conflict resolution and any difficult conversation. Stephen Covey, the author of The Seven Habits of Highly Effective People once said, “Seek first to understand and then to be understood.” That’s an important concept in any conversation. In order to promote your own active listening, you can do the following:

  • Ask open-ended questions, rather than questions that elicit simple “yes” or “no” answers.
  • Paraphrase what the other person has said in order to ensure that you have understood them correctly.
  • Acknowledge the other person’s feelings by saying things like, “I hear that you are upset about…”

Tool #3: Adopt the “Yes, and” Stance

Many people have heard of the “yes, and” stance from improvised comedy. Someone else suggests a scenario and you agree automatically and then add to it. Within difficult situations, the “yes, and” stance is similar: you recognize that the way both of you see the situation has value. You can say something like, “I understand you felt x, but I also walked away and felt y.” Once you have understood each other, you can then talk about how to resolve the issue.

Tool #4: Learn to Recognize your own Stories

We all tell ourselves stories about why someone did something. Usually those stories are close to reality, but even the most honest person tells a narrative that might not be completely accurate (“She cut me on line in the supermarket because she thinks her job is more important than mine,” or “”He never listens to anything I say because he thinks I’m boring.”) It’s important for us to separate our own stories from the reality of what happened. (“She cut me on line” or “He didn’t listen to my story.”) Once we are aware of what the action was separate from our story, then we can begin to create a safe space and discuss it.

Tool #5: Use “I” messages

When we tell people, “You hurt me,” they are immediately on the defensive and the conversation can become more difficult. Instead, if we say, “I felt hurt when you did that,” we are shifting the blame from them to the action. This allows a safe space for conversation in which people can listen to each other and begin to value the other person’s side of the story.

Tool #6: Focus on contribution, NOT blame

Rather than focusing on “who is to blame,” we can think about how each party contributed to the problem. In this way, we validate the two sides of the story and also allow there to be a conversation without playing the blame game. Then, once you acknowledge the contributions, you can begin the conversation about how not to repeat it in the future.

We’d all like to avoid difficult conversations, but if you are forced to have them, you might as well have the tools to resolve them peacefully and positively!

An acclaimed educator and social skills ​specialist​, Mrs. Rifka Schonfeld has served the Jewish community for close to thirty years. She founded and directs the widely acclaimed educational program, SOS, servicing all grade levels in secular as well as Hebrew studies. A kriah and reading specialist, she has given dynamic workshops and has set up reading labs in many schools.   In addition, she offers evaluations G.E.D. preparation, social skills training and shidduch coaching, focusing on building self-esteem and self-awareness.  She can be reached at 718-382-5437 or at You can view the web at


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