Play this scenario out. You have a friend, family member, or co-worker and you know you need to have one of those conversations with them. You know, the type of talk where you share with them about how their actions are negatively affecting them personally and also the people around them. However, you don’t know how to go about. Thoughts flood your mind, “It’s not my place to talk with them,” “Who am I to judge them,” “Their actions aren’t really that bad,” or “What will they think of me if I bring this up.” You can’t sleep as you think about what you should do. You even start avoiding that person.
Have you been here before?
One of the most difficult types of conversations to have is confrontation. And yet, if we truly care about people we should be willing to speak the truth in love. When I think about the people who have had the most impact in my life, they all have had one thing in common. They all confronted me. At the time I didn’t like it, but looking back I’m grateful they had the courage and took the time to challenge me. Those conversations allowed me to see blind spots, encouraged me to seal up weaknesses, and overall they produced growth and maturity in my life. And that’s the purpose of confrontation. It’s not to belittle or make someone feel bad; it’s to reveal areas of unhealthiness and spur them on towards a change in behavior.

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Deep down we know confrontation is important and that we need to have these conversations. But how do we confront effectively that encourages but still challenges the person we are talking with? Here are a few things I think through before I engage in one of these hard talks.
Know Yourself
When it comes to these difficult conversations, you need to know where you fall on the confrontation pendulum. (I share more about my pendulum philosophy here.) Do you lean towards avoiding these talks or engaging too quickly in them? For me, I tend to confront too much. Therefore, when a potential confrontation situation arises, I will evaluate if this conversation really needs to happen and usually consult a close friend who is on the opposite of the confrontation pendulum to help balance out my bias.
Relationship is Key
“Confrontation is best received in the context of a relationship.” Those words remind me that the person I am confronting needs to know I care about them. If they don’t, then it will be more difficult to hear what I’m trying to share with them.
“Confrontation is best received in the context of a relationship”
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Private
Confrontation should always be done in private or at least not where others can hear. Have you ever seen a coach call out his player in front of the whole gym? It’s embarrassing and the confrontation is usually not received well. Find a place where you can have an honest dialogue that doesn’t draw undue attention to the person you are talking with. A few years ago I was hanging out with a few friends at my mentor’s house. One of his children was not being obedient to something that he asked her to do. In the middle of a crowded living room, my mentor leaned in close to his daughter and at a whisper reminded her that she needed to obey. It was a brilliant way to confront his daughter, but not embarrass her.
Be Specific
I have seen too many times a manager says something like, “I need your work to be better.” What does that even mean? What work needs to be better? What steps do I need to take to improve my work? We need to be specific when confronting. For example, “Can you make sure to turn in this project by the specified due date?”
Address the Action
No personal attacks. Name-calling is not an effective way to confront. Address the action that was wrong, not the person. Instead of saying, “That was a dumb thing to do.” We can share, “The decision you made was unwise.”
Explain the Why
Besides the person knowing you care about them, I think explaining the “why” could be the most important step in confronting. Think through why this person’s actions need to change? What are the bigger implications if they don’t modify their behavior? A few years ago, I had a staffer accept a summer job on my team. A week before he was supposed to show up, he called me and quit. I could’ve let this slide. But I wanted him to understand the implications of quitting. Most importantly I didn’t want this lack of commitment to become habitual. So I talked to him about it. In the moment, he didn’t receive it well but a year later he called me back and thanked me for having that conversation with him.
Not every confrontation will end up like that where you see the benefit of your conversation. But if we truly care about someone, we need to be willing to speak the truth in love, gentleness, and boldness.
Is there someone in your life that you have been putting off a tough conversation with? If so, what is the first step you need to take to effectively confront them?
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