How to Have a Difficult Conversation

“Tough chats are manageable if you have clear steps to take. Experts share tools that they have used in their own lives.

 

I once had an issue with a close friend — but instead of talking to her about it, I put off the conversation for months.

 

When she invited me over for dinner, I finally decided to unburden myself. By that point, though, I had worked myself into such a state that I felt dizzy. My friend had to lead me to her couch and get a cold cloth for my forehead.

 

I could have avoided that situation if I had talked to her when I first got miffed.

 

It’s tempting to delay a difficult conversation, especially with someone you care about or see often, said Matt Abrahams, a lecturer at Stanford Graduate School of Business and the author of “Think Faster, Talk Smarter.”

 

“We do this hoping and praying that it’ll get better on its own,” he said.

 

But tough conversations are less daunting if you have clear steps to take. I asked experts to walk me through them.

 

Choose an appropriate moment

 

Finding the right time and the right place are crucial, said John Caughlin, a professor of communication at the University of Illinois at Urbana-Champaign.

 

Approach the person when things seem calm, he said, adding that tough conversations should generally be done in private.

 

Chatting in person is best, Abrahams said, because you can “read cues and clues” in a way that you can’t on a device. And, he added, making time to meet up signals that the conversation is important to you.

 

If possible, have the discussion outside, said Jefferson Fisher, the author of “The Next Conversation.” It’s something that he often likes to do, he told me. If you’re sitting on a park bench, you’re not staring into each other’s eyes, which can be difficult for some people, he said, and you can take a break to look at your surroundings if things get intense.

 

Give the person a heads-up

 

Convey that this may be a difficult conversation by starting with what Fisher calls a “heads-up sentence.”

 

Tell the person, in a neutral way, that you’ve been bothered about something: “‘Hey, I’d like to get something off my chest,’ or ‘I’d like to talk with you about something that’s been on my mind,’” Fisher said.

 

You can also set a collaborative tone by saying, “I need your help with something that’s been bothering me,” he said. That puts you on the same team and can prevent the other person from feeling defensive.

 

Give them a quick preview of your topic so you don’t leave them “gripped by fear and thinking, ‘I’m in trouble,’” Fisher said. In my own life, I’ve learned not to tell my husband “we need to talk,” which causes him to freeze like a rabbit, but to say something specific such as “We need to talk about our credit card bills.”

 

It’s never pleasant to have a challenging discussion, but it’s even worse when a person has no idea that it’s coming, Fisher said.

 

Keep calm and stay on message

 

Establish a three-part goal for yourself, Abrahams said: What you want the person to know, what you’d like them to feel and what you want them to do. (Write it down beforehand if it’s helpful.)

 

If the conversation derails, keep returning to your goal. “That can help you stay grounded when things are in motion,” he said.

 

If you get pushback, Abrahams likes to use paraphrasing “as a tool to stay the course.” Simply repeat what the person is saying in your own words. This validates their point of view and can calm them down, he said.

 

“It doesn’t mean you agree, it just means, ‘I’ve heard you,’” he said. “Then get back to your point.”

 

At the end of your conversation, thank the person, Abrahams said. “You can say, ‘Hey, I really appreciate that you were willing to work this through with me,” he said. And if you’ve come to a resolution, he added, briefly summarize it in a way that’s clear for both of you.

 

If you haven’t resolved the issue, he said, “You can say, ‘I hope you hear that I really want to work this out with you,” and suggest you revisit the subject later. “Most of our interactions are not one and done,” he added.

 

After I stumbled to my friend’s couch, she made us some tea, pulled a blanket over both of us, and we talked things out. It was hard. Then it wasn’t. I shouldn’t have waited.” [1]

 

1. How to Have a Difficult Conversation: The Well Newsletter. Dunn, Jancee.  New York Times (Online) New York Times Company. May 15, 2026.