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How to Have a Difficult Conversation

May 18, 2026 By Joy Rosenthal

Two women sitting by the water at sunset

Two women sitting by the water at sunset, courtesy of Unsplash

Have you ever wanted to say something to a close friend but were a little scared to bring it up? Maybe it was a response to something they said that hurt you, or an observation, or a deep secret…. We have so many reasons for avoiding difficult conversations. We may want to avoid a conflict or feel too vulnerable.

I was interested in Jancee Dunn’s recent article in the New York Times’s Well newsletter, called “How To Have a Difficult Conversation.” She suggests a few techniques that are much like mediation:

  • Choose the appropriate moment. I equate this to creating a safe space, so that you each can have the focus and attention that the matter deserves.
  • Give the person a heads-up. This is giving the other person a warning that it’s a serious topic – not just talking about the foam on your latté.
  • Keep calm and stay on message. Much of my work in mediation is helping people stay on point and stay calm. Arguments can often spin out of control, but anyone can get it back on course. In this section, Ms Dunn also talks about repeating what someone has said – even if you don’t agree with it. But at least that lets them know that you are listening.
  • Appreciate them for engaging. It is important to acknowledge – even if you haven’t resolved the issue.

All of these things help you work together to acknowledge that the breadth and depth of your relationship is more important than the one thing at hand.

Filed Under: Collaborative Process

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The information on this site is not, nor is it intended to be, legal advice. You should consult an attorney to obtain legal advice regarding your own situation.

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New York, NY 10036-7424

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