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Difficult, Not Bad: Navigating Tough Conversations

Tim Ditman
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Sara Bennett

Key takeaways:

  • When working through a difficult conversation, choose a goal and find the right time.
  • Use “I messages” rather than putting the blame on others.
  • Be an active listener. Don't get distracted by devices.

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“I deserve a raise!”

“Son, your grades are slipping.”

“Honey, we’re not spending enough time together.”

Difficult conversations come up more often than you’d think. Luckily, there are time-tested ways to navigate them, says Sara Bennett, a psychotherapist at OSF HealthCare.

  • Choose a goal. Figure out what you want out of the talk, whether that’s the raise you’re after at work or just a better understanding with someone close to you. Also plan how you may react to responses.

“Hopefully that goal is to not be right. Hopefully it’s to come to some kind of resolution or share some information. Maybe you’re seeking advice,” Bennett says.

In other words, you can be right, or you can have good relationships, Bennett says with a smirk.

  • Find the right time. Don’t jump into the conversation when you’re still upset. Calming down will lead to a more logical approach.

    A script to try: I have some important things I’d like to talk about. When’s a good time to do that?

  • I messages.

    Bennett explains: “Sometimes when we approach things too directly, it makes the other person put on their armor. Difficult conversations are both listening and speaking. You want to understand what’s happening and present your topic logically.”

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    So instead of: You never do the dishes and take out the trash, and that makes me overwhelmed.

    Try: I feel very overwhelmed when I come home, and the kitchen is chaotic.

  • Active listening. As the name implies, really take in what the other person is saying. Don’t let words go in one ear and out the other.

    “That can look like nodding your head in agreement or asking for something to be clarified so we both are understanding,” Bennett explains. “This really avoids miscommunications and misunderstandings, which can escalate a conversation.”

    And of course, stay off your device during this talk. It’s tough in this technological age, but it’s important.

It just isn’t working

Despite your best efforts, maybe you can’t work things out in conversation. What then?

First, Bennett says don’t give up on trying again later to find some common ground.

“This is probably a subject that you haven’t brought up before. Even if this conversation doesn’t go the way you’d like it to, it’s very likely this is not a one-and-done subject,” Bennett says. “Just like the problem didn’t happen overnight, the solution probably isn’t going to happen overnight.

“Be patient with yourself and the other person,” she adds. “Feel the emotions of being disappointed, but then ride that wave and let the emotions pass. Try to keep in mind that this is a step forward even if it wasn’t what you expected.”

Depending on the situation, talking to a mediator or counselor can help. Schools have guidance counselors, workplaces have human resources employees and health systems have therapists who can talk with you one on one, as a couple or in a group.

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