Our Top Strategies to Get Ready for That Difficult Conversation

How often in my life have I started a difficult conversation by waiting, waiting, waiting . .  . then exploding emotionally all over the person? My youth was characterized by that—ask my mom! Then, in my 20s, as I went out into the world, I needed to act more “grown up.” I became a little more careful about controlling how I said things. I chose nicer words, but the truth is, the emotions still leaked out onto everyone else. Who was I trying to fool? 

Preparing for difficult conversations still made my gut tie up in knots and my stomach churn. No wonder I tried to avoid them. No wonder that emotional energy was pressurized to the point of explosion.   

It didn’t happen all at once, but over time, I’ve learned a few things–sometimes through failure, sometimes through proactive learning and hard work. As a result, I’ve developed a pretty decent toolbox for helping myself with difficult conversations.  

The work we do in advance of conflict is vital to success.  

The following is not a comprehensive list, but it includes many of the steps of preparation even before you even open your mouth and begin to engage in that difficult conversation.   

Photo by mk. s on Unsplash

Cultivate humility:   This attitude doesn’t come naturally to me. It’s a sacrifice to let go of my own “rightness” and be open to seeing that others may–ok, usually do–have a valid perspective. I’ve been working to develop some skills, reminders, and practices that help get my heart in this place of believing others have things to say that are valid and would make sense from their context. When I have my heart in a humble place, I can acknowledge my contribution to the problem. I don’t have my argument planted in concrete, but rather I am coming up with draft thinking, and I am ready to learn.

Learn to listen:  I spoke to a teenage leader once who was sharing her frustration with me. Finally, she blurted out, “I just wish they would listen to me! I want them to understand just how great my ideas are!” We may laugh, but we all really want people to listen to us like that. It’s much harder to give the kind of listening we want to others. We want others to truly hear what we are trying to communicate, to understand our intentions. So, of course, it makes perfect sense that we would be ready to listen to them the same way we wish they’d listen to us. However, for some reason, we rarely think of that, let alone practice in advance. 

Use “I” statements:  Having a productive conversation is really about learning. When we make “you” the subject of our sentences, we are setting ourselves up for a more aggressive, attacking battle, where there truly are no winners. Using “I” statements is critical to producing a constructive atmosphere. For example, change  “You don’t listen to what I have to say in staff meetings” to “I've been feeling unheard in our team meetings.” Granted, “I” statements take work and practice to use in an authentic and honest manner. 

Ask better questions:  Our brains want to know why, so “why” questions are common go-to questions when we don’t understand. The problem is they put people on the defensive, and this sets up the conversation for failure from the start. Learning to create questions that help us understand what is important to the other person, or what they mean by their word choices, is more helpful in the long run. 

Know your own story:  We often tell ourselves a story about what is going on, and, usually, we fill in the missing pieces with our own interpretations. Write out the facts of what happened, the things you are assuming, your feelings about what’s going on, and get really honest about where this situation is poking at your sense of identity. See our article on “Three Parts to All Difficult Conversations.” 

Know your conflict patterns: We all have habits when it comes to how we deal with conflict. Decide in advance if you want to have a productive learning conversation that has the potential for mutual growth and connection. Then, take an honest look to see if you are truly heading toward that or falling back into an unhealthy conflict pattern. 

Understand your values:  Notice which of your values is being disturbed by this situation. Be able to articulate what the value is and what is interfering with that value. Push yourself to become curious about what the other party might value and how you might be intruding on their values. For example, when I was interrupted by someone with a rather booming voice, my value on justice or equality got triggered. My voice, albeit less voluminous, was worthy of being fully heard. I also have a value on closure, so not being able to finish my sentence was difficult for me.

Get regulated:  If you are feeling stuck or frozen, or, conversely, are at the point of wanting to physically fight or flee, you won’t be able to have a helpful, connected conversation. Learn how to get in your “Window of Tolerance”—that place where you can be calm, cool, collected, and able to connect with others.    

Know your purpose:  Sometimes, we want to have this difficult conversation so “things change.” Sometimes, it’s because our emotions are high, and we are looking to release them.  Although desiring change and releasing emotions has some merit, these reasons often don't lead to the most productive outcomes. Ask yourself the following questions: If things go well, what would you want to see happen? What result would be enough for this conversation? What outcome can you plan on, even if you are the only one who is working on this difficult conversation?  

By definition, conflict means we are divided in some way. However, practicing the attitude of humility and implementing the skills mentioned above have the potential to produce so much good in us. I’ve seen blind spots in my character and have been able to grow and develop in those areas. My unexpected favorite part of this development is seeing how often I’ve grown to be more connected and closer to those with whom I've worked through conflict. 

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