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How to Handle and Disengage From Challenging Conversations


Have you ever had a conversation where someone just had to prove you wrong no matter what you said or how you said it? You could present all the supporting evidence you wanted, but this person would still try to prove you wrong. This person acts like they know everything, and they are not afraid to tell anyone who will listen. Even if you use logic and concrete evidence to prove them wrong, even if you use their arguments against them, they still insist that that’s what they’ve been saying all along, and they were always right.

The Challenging Conversations We Don’t Want

There might be that person who just won’t let the conversation go. You could walk away and say that you completely agree with them just to end the conversation, but this person follows you out the door to your car, still explaining why you are wrong and they are right. By the end of the conversation, you wonder why you started talking to them in the first place. You may even make a mental note never to make that mistake again.

Then there are those conversations that you must have that you do not want to. Maybe you’re a supervisor and need to have a coaching moment with an employee about poor performance. Perhaps you are a public servant like a social worker or a law enforcement officer and have to deliver bad news. You might have to bring up an unfortunate accident to a friend or family member, like a car crash or breaking or losing something precious. Just beginning those types of conversations is difficult. Even if you’re just the messenger, unfortunately, you are the one that the recipient can direct their emotions towards.

Leaving these kinds of conversations can be as difficult as conducting the conversation. Words have the power to stick with people forever, so when you engage in those difficult conversations, you have to choose your words wisely. Here are some tips and tricks for making those problematic conversations flow more easily so that you can leave on a positive note.

Make an Effort for Positive Communication 

When having those difficult conversations, be sure to engage in active listening so that the person talking knows that you are present and listening. Let them speak and then paraphrase what they said back to them. If they feel that you aren’t getting what they are trying to say, ask them to help you understand. Focus on understanding what you can do to remedy the situation rather than getting frustrated by the damage done. Once they stop speaking, allow a few moments of silence to pass to make sure that they have completed their thoughts.

When it is your turn to speak, be clear and concise. This does not mean talking down to anyone but rather avoiding beating around the bush and just saying what you want to say. If what you are saying does not seem to be getting through, or you feel yourself getting frustrated, call for backup if possible or take a break and come back to the subject later. The most important aspect of this sort of conversation is that you keep your emotions in check to avoid hurtful outbursts. Once your emotions get involved, effective communication becomes more difficult. Try to leave the conversation with concrete ways one or both of you can improve to make the situation better.

How to End those Difficult Conversations

If the person you are speaking with immediately becomes defensive or tries to tell you why you are wrong about everything, ask them to explain things from their point of view. Not only will this make them feel that their feelings are being validated because someone is listening to them, but you are also able to more clearly see their side of things. If you just cannot agree with what they are talking about, you can offer to agree to disagree and end the conversation on a positive note. This way, you are telling the other person that although you do not agree with them, you respect them enough to end the conversation in a courteous manner. Another way to end the conversation on a positive note is to find something you can both agree on and focus on that.

When They Won’t Let It Go

Sometimes the person you are speaking with will not let the discussion end, no matter how often you try to close down the conversation. Sometimes one or both of you might be getting so emotional that soon feelings will get hurt, and you need to walk away before they do. That’s okay: let them know that you will need to continue the conversation at a later time and schedule some time with them before they leave. Thank them for allowing you to walk away for the moment, and end the conversation there. When you’ve both had time to cool off, return to the conversation with a fresh perspective.

Finding the words to have difficult conversations can be hard. Not only can they cause stress and anxiety to both parties, but words must be chosen carefully in order not to inflict permanent damage on either side. Handling and disengaging from those difficult conversations take patience and emotional maturity. It’s not always easy to find the words that you need, and emotions threaten to take over. This is where practice and support come into play. Practice seeing situations from others’ points of view and practice active listening and motivational interview skills when you can. You don’t have to be a social or mental health worker to engage in either skill. Most of all, practice keeping your emotions at bay when you feel angry or frustrated. Headlight can provide the counseling you may need to handle difficult conversations. To find out more about how we can help, call 503-298-4592.

More than 50% of Americans struggle with mental health.

Headlight is now collaborating with health plans and companies to make therapy more accessible and affordable. Speak to a Care Coordinator today.