How to Play a Positive Role in Difficult Conversations

Jun 16, 2014
6 Min Read

It can be frustrating to have a conversation with someone who is difficult. You may come away from the experience without the answers you wanted, and believe the person is a selfish, immature jerk.

But instead of blaming the other person for the bad interaction, consider that it may be a matter of you not clearly defining an issue or problem and letting the conversation get off track.

In a new book, “I Hear You: Repair Communication Breakdowns, Negotiate Successfully, and Build Consensus… In Three Simple Steps,” Donny Ebenstein offers advice on learning to behave and think differently when interacting with difficult people. In this interview with Anita Bruzzese, he explains a strategy that involves role-playing to improve your communication skills.

AB: What exactly do you mean by role-playing? Is it like pretending or acting?

DE: Role playing is a technique in which two people take on roles, and then have a conversation while in those roles. For example, if I were to role play a conversation in which I want to ask my boss for a raise, I would take on the role of myself at work, and my partner would take on the role of my boss. I would begin the role by asking for the raise, while my partner would respond as my boss, and we would continue the conversation from there.

The key to role playing is that there is no script; my partner, as my boss, is free to react in whatever way feels natural to her in that role. The conversation progresses with each party reacting to the other, unscripted.

AB: Why is role-playing so important when it comes to improving your communication skills?

DE: When done correctly, role playing provides a realistic and authentic sense of how a conversation may go, which is enormously valuable.

If I am considering adopting a forceful approach to asking my boss for a raise, for example, I can first role play it with a friend or colleague as my boss and gauge their reaction, helping me to determine if this is the right approach.

In addition, role playing offers an opportunity to practice and fine-tune one’s skills before a difficult conversation.

AB: What are some keys to successful role playing? Do you have to write a script?

DE: In role playing, unlike acting, it is important NOT to write a script.

3 Tips for Role Playing Successfully

  1. Choose the right partner. It should be someone with whom you feel comfortable trying something new, and with whom you can pause the role play and discuss what is happening in an honest way.
  2. Describe the role thoroughly. Do your best to describe the other person’s character empathetically. If I were describing my boss to someone, I shouldn’t say “your character is a cheapskate,” but rather “your character tries to avoid wasting the company’s money at all costs.” People usually have a positive view of themselves, and you should empower your role-playing partner to take on that positive self-image in the role play.
  3. Let the conversation flow naturally. After allowing it to progress, pause, using the break in the action to explore both your own reactions as well as your partner’s reactions to what’s been said so far. 

AB: You say that role-playing can make us more self-aware and shift our perspective. How so?

DE: One way to use role playing to shift perspective is to do a role reversal. In the example of asking my boss for a raise, in a role reversal I would play my boss, and my partner would play me, and we would then have the conversation with these reversed roles.

Doing so provides an opportunity for me explore what my boss might feel like as I examine my own feelings while inhabiting his role. It also allows me to consider how I may sound to my boss when confronted by my partner saying the things I would normally say to my boss.

This can be an extremely powerful and eye-opening experience, and I have used this technique with many clients to achieve breakthroughs in their toughest situations.

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