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Conflict Resolution Institute

A Step-by-Step-by-Step Checklist for Difficult Conversations

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By Danyah Al Jadaani, CRI Staff, MA '21.

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Difficult conversations are never easy, they can come up in the work place as well as in personal situations. Difficult conversations can sometimes bring that dreaded feeling that talking about the conflict it could possibly make it worse, or perhaps there have already been attempts and those attempts have gone badly. Fear not, because there are many well-written books on how to have these important, crucial, and sometimes intimidating conversations. Judy Ringer, writing on's useful website, has developed a checklist of 'best practice strategies' to think about before going into the conversation. This includes some useful concepts to practice during the conversation, tips and suggestions to help your energy stay focused and flowing, and possible conversational openings. By thinking about these best practice strategies ahead of time, you will be more likely to stay on topic and the conversation will less likely devolve into unproductive conversation.

10 Tips for Having Difficult Conversations

1. "Take a moment to think about what you hope to accomplish. Ask yourself the following questions: What is your purpose for having the conversation? What do you hope to accomplish? What would be an ideal outcome? 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, but be cautious about assuming their intentions. Impact does not necessarily equal intent. Keep an open mind."

3. "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."

4. "How is your attitude toward the conversation influencing your perception of it? If you think this 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."

5. "Who is the opponent? What might they be thinking about this situation? Are they aware of the problem? If so, how do you think they perceive it? What are their needs and fears? What solution do you think they would suggest? Begin to reframe the opponent as a partner and it is you two against the problem, rather you against one another."

6. "What are your needs and fears? Are there any common concerns? Could there be?"

7. "How have you contributed to the problem? How have they?"

8. "What are the steps to a successful outcome?" Ringer argues that inquiry, acknowledgement, advocacy, and problem solving are key to having a successful difficult conversation. Ringer says "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."

9. Ringer also mentions the following "Acknowledge emotional energy – yours and theirs – and direct it towards 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 they can see things from your point of view."

10. Ringer summarizes her article to say "Practice the conversation with a friend before holding the real one. Mentally practice the conversation. See various possibilities and visualize yourself handling them with ease. Envision the outcome you're hoping for." Difficult conversations are hard, but you will get better at it and it will ultimately help not only in your career, but your personal growth as well.

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