Conversations with people are not always pleasant. In fact, sometimes conversations are down right unpleasant and awkward. Unfortunately sometimes these conversations are also necessary for your own good, the other person’s own good, or the good of both of you.


Earlier this week I delivered a program about initiating awkward or uncomfortable conversations. I decided to deliver this program because I don’t feel confident with confrontation. The very best way to learn is to teach and practice.

Is confrontation necessary?

One of the very first steps is to determine if the confrontation is even necessary. Not all issues need to be addressed. People sometimes get mad just because someone did something to them. Will it make any difference (other than getting it off your chest) if you confront that person? For example, if someone cuts you off while you are driving, what good will come from an impolite hand gesture? You will likely never see that person ever again. If they cut you off on purpose, your confrontation will not prevent them from doing it again. If they cut you off by accident, they already feel bad and don’t need someone reminding them of their mistake.

Making excuses

I am really good at finding a reason not to confront someone if there is an issue. My personality values relationships so I will find myself accepting an issue with someone in my attempt to salvage the relationship. I have learned that in time, I am actually hurting the relationship. Allowing the issue to continue unresolved can slowly chip away at your relationship. There can be a cost to avoiding confrontation with someone.

Managing anger

As I mentioned earlier, it can be easy to let anger get the best of you. Anger rarely can help you in a time of confrontation. One of my favorite quotes:

“Speak when you are angry and you will make the best speech you will ever regret.” – Both Ambrose Bierce and Dr. Laurence J. Peter are attributed to this quote

To help manage your anger, take a minute and breath. When you recognize that you are angry, ask if you can have a minute. Collect your thoughts. Prepare to find a resolution.

One of my favorite bloggers, Seth Godin, recently posted about how to have difficult conversations at work. I agree with Seth when he suggests, not using email when the outcome of the conversation is in doubt. Instead you should speak with the other person face-to-face. Your advantage is the opportunity to change your tone as you listen to the other person during the conversation. You also have opportunities to ask great questions which is usually better than good answers.

Check your motivation

Why are you considering the confrontation? Make sure that your motivation is that you are looking out for the best interest of the other person. Your motivation should be about helping them be more effective. I think the quote from Stephen Covey applies to this as well when Dr. Covey says “Begin with the end in mind”. Envision what the result of your conversation should look like before you even start the conversation.

Key requirements for a difficult conversation

  • Make sure the other person is okay with discussing the issue. They may need some time to mentally prepare for the conversation. Remember you have already had time to collect your thoughts. The other person deserves the same opportunity.
  • Always speak in private. The old rule of praise in public and counsel in private is true here as well. There is nothing to be gained by either one of you in a public confrontation.
  • Be objective when describing the issue. Stick with factual statements and any emotions that YOU have about the issue. Describe how this issue impacts effectiveness, productivity, relationships, etc. Stay away from inserting other people’s opinions.
  • Be concerned with the other person’s feelings during the conversation. This stance will help you make positive progress.

When you need to have a difficult conversation with someone, take time to prepare how you want to handle the conversation. Make sure the conversation needs to happen, then paint a picture of what you intend the outcome of the conversation to be. Taking a little bit of time to think about these things can help you and the other person benefit from the conversation.

What is the most difficult conversation you have ever had?
Did the conversation make things better or worse?

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6 thoughts on ““I need to talk with you. . . ” Having a difficult conversation

  • at 10:24 am

    The worst difficult conversation… I can’t think of it from the top of my head, but I can think of my most recent one. A friend of mine and I were having a conversation with some other people, when we moved to a certain topic that has us on opposing sides. I was edged out of the conversation, just like that, and my feelings were a bit hurt.
    I’m glad you’ve posted this, because for the next hour or so I was dealing with my own emotions and what they all meant. I came to the conclusion that they were only trying to avoid and argument with me on a touchy subject, although I disliked the way they did it.
    My solution was to send them a quick online message; first apologizing if I had seemed as though I were trying to pick a fight, them letting them know how much I appreciate their friendship.
    You are also right about waiting for the other person to process how they feel. I’m leaving my friend to do that now.
    Thanks again for posting.

    • at 10:20 pm

      Thank you for sharing your example. It is hard to go wrong when you are truly humble.

  • at 12:03 am

    Good checklist – thanks for sharing.

    I’ve had to have so many difficult conversations over the years – probably the worst are telling an employee that they aren’t measuring up and what needs to change. They get fearful and shut down without hearing that they can fix the situation and it’s not irrevocably broken.


    • at 7:27 am

      Thanks for your comment Nancy. Yes this is difficult. When I have had to tell an employee they aren’t measuring up, I try to help them come to discover there is an issue. I had an employee once who studied to be in the profession but didn’t have the natural skill. Helping him evaluate his own effectiveness helped him discover that even though he had all the education, he didn’t have the natural skill, which is why he didn’t enjoy his job. I worked with him to find another job in the company that he was perfectly suited for. I also learned to hire better.

  • at 5:10 am

    This was helpful to me. When I was younger I was told that I was confrontational in personal relationships. I took that to heart and feel like I have let some things go that maybe I shouldn’t. It is hard to find the balance of when to let things go and when to “have a talk.”

    • at 6:25 am

      Your comment here is very true. I hope that some of these guidelines can help with drawing that line. I struggle with it all the time.


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