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Difficult Conversation
September 30, 2021

Handling Difficult Conversations: The Approach Matters

 I recently had a series of hard conversations with someone I really care about. I wanted to talk about some behavior I had noticed. Although I had good intentions, I didn’t handle the conversation well, making a difficult situation even worse. I went into the discussion with some preconceived notions, fear, and judgment, and it went about as well as you’d suspect. The interaction was tense and awkward, and neither of us felt good about it. However, we eventually worked it out, and I believe we are better for it.


As leaders, we have to learn how to handle difficult conversations well. It comes with the territory of leadership. But, in going through these experiences, our relationships with associates, colleagues, and employees can either get better or worse.


Many times, the conversation is won or lost in the approach. When I initiate the conversation, I have to be really clear about my intentions and frame of mind, or it will blow up in my face. So before any potentially difficult conversation, I get clear on these three Cs: Curiosity, Context, and Cooperation.




No one likes to be accused of something they did without first having a chance to explain. The most productive conversations happen when both sides are relaxed, so it’s important to enter these conversations with an attitude of curiosity. You and I may actually have no idea about some of the circumstances surrounding the actions or behavior we want to address. When we assume a position of curiosity, we allow the other person to shed some very important light on the matter.


While I don’t always get this right, I generally start the conversation with questions rather than accusations and try to remember the importance of my facial expressions and tone. Being curious doesn’t just mean asking questions. How you ask them is equally important. These two questions are basically asking for the same information:


“Why did you do that thing?! What were you thinking?!?”


“Can you please give me some clarity and understanding around the decision you made? Help me understand your thought process here.”

See the difference?


You don’t know what you don’t know, so don’t assume you do. However, what you don’t know can hurt your relationship and influence as a leader if you don’t give space for the other person to share.




Acknowledge your context. Your personal history matters because past experiences teach us and contribute to our growth. However, no two experiences or people are exactly alike, and it’s important to remember that. In my case, I projected fear onto the person I was confronting, and it caused me to expect the worst. What’s crazy is this person had never done the things I was afraid of. I was projecting my past experience on this person, and it created confusion and broke down trust. Before I even talked with the person, I had drawn a negative picture in my mind. Unfortunately, my perspective led me to a false assumption. However, I learned this current circumstance was different than what I’ve experienced before.


You are who you are today in large part due to your experiences. But stay open to new information and context as you remember each situation will be unique. For me, I often think about this verse:


Don’t copy the behavior and customs of this world, but let God transform you into a new person by changing the way you think. Then you will learn to know God’s will for you, which is good and pleasing and perfect.

Romans 12:2 NLT


I try to remember that what I think I know may not be accurate as I face situations. I have to listen and seek the Lord to change, grow and think more like Him. I recognize that my thinking can sometimes be wrong. God actually used this situation to reveal the issues in my own heart and mind.




Choose cooperation over condemnation. It may turn out that the other person’s behavior disappoints you. None of us are perfect. And, just as I make mistakes, I have to know those around me will do the same. When an employee or friend admits their failures, cooperation wins over condemnation. Most likely, the other person is already feeling bad about their decision. Rather than adding to their guilt, we can add value to them as we choose to come alongside and help them grow.


When I value the person over their actions, it’s easier for me to respond this way. We should want the best for people just as Christ does for us. Growth happens more easily when we show genuine care and help with problem-solving, even when expressing the situation’s impact and how it affects us and/or the organization.


We’re all going to deal with confrontation from time to time. However, our approach can lead to growth and stronger relationships if we’re intentional about it. Be curious, think about the context, and find ways to cooperate. As we do this, we lead with much more love, justice, and righteousness. The approach makes all the difference.


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