7 Steps for Navigating Challenging Conversations

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From the time I was young, I was taught that there are two subjects that should never be discussed in mixed company: religion and politics. The last thing my parents wanted spoiling a nice evening with friends or relatives was a heated debate over contentious issues. As kids, my sister and I learned to limit our topics of conversation to what we were learning in school and the movies we had recently seen.

What was a successful strategy for managing dinner parties, though, may not be an ideal goal in other contexts. Simply avoiding a difficult topic doesn’t make it go away. But talking about controversial subjects in the usual I’m-right-and-you’re-stupid manner we see every time we turn on the TV or open the newspaper doesn’t either. The unrest over racial justice we’ve witnessed during the past several months and the divisive, mean-spirited rhetoric that characterizes our political discourse today make it painfully clear that we have a long way to go in “loving our neighbors” if we can’t even talk with them.    

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But it doesn’t have to be that way. Like anything else that’s challenging, talking with people who are different from us – in terms of race, religion, socioeconomic status, political views – requires the careful use of specific skills to be successful. The book, Crucial Conversations, outlines several of these important skills. At work, I was part of a group of managers who were trained on these skills in a corporate setting to help us have the tough conversations we needed to have with employees we supervise. Through that experience, I began to realize that my parents’ approach to talking with guests is not the way to understand and connect with someone who is important to me whose views are very different from my own.  

1. Know when it’s crucial

A “crucial conversation” involves three key elements: differing opinions, strong emotions, and high stakes. Certainly, conversations involving differing views on race and politics can be considered “crucial.” Others include things like ending a relationship or addressing someone who has hurt us. The authors argue that whenever we find ourselves “stuck,” there is a crucial conversation that we are either doing poorly or avoiding altogether.  

2. Be clear on motive

To be successful, both parties need to share the same goal. If my goal in talking with you is to “win a debate” or to “prove that I’m right,” then I’m not ready to have a crucial conversation. If, on the other hand, I truly want to understand your point of view and want you to understand mine and if we both want to find a solution that works for each of us, then we are ready.

3. Start with observable facts

The best way to open the conversation is with indisputable facts. If I tell my boss, “I think you are prejudiced against the black females in our department,” I have begun with a negative opinion that will put him or her immediately on the defensive. Instead, if I start with, “I see that the last five people promoted in our department were all white and four of them were male,” then there is nothing to dispute.  Starting with verifiable facts gets the conversation going in the right direction.

LISTEN: Mary Ann Steutermann Talks About How to Have Crucial Conversations

4. Then, tell your story

The authors argue that every issue has two components: the facts and “the story we tell ourselves about the facts.” Therefore, I should follow my fact-sharing with, “The story I tell myself about those promotions is that black females in our department don’t have the same shot at advancement as white males do. Is that how you interpret the situation or is there another way to look at it?” This allows me to put forward my viewpoint but in a way that leaves the door to other interpretations. It’s important to ask for the other person’s “story” too, not just advance our own.

5. Beware of “silence” and “violence”

The key to a productive conversation is for each person to feel “safe” throughout, meaning that each person feels respected, and both parties share a common goal. When people start to feel unsafe, they either become “silent” by holding back or “violent” by resorting to insults or accusations. If I see any of these signs, I must pull back from the conversation to get it back to a place of safety for both of us.

6. Restore mutual respect

If I have created an unsafe environment by being disrespectful, then the only way to fix it is to sincerely apologize with something like, “I’m sorry. I should not have said that you are biased. Really, you are a very fair boss which is evident by the way you manage the vacation schedule and holiday hours.” When we are wrong, we need to own it. 

But sometimes we haven’t done anything wrong; we’ve just been misinterpreted. In these instances, the skill to use is “contrasting,” where we make it clear what we are NOT trying to say. If my boss thinks I have judged him as a poor leader, he will feel unsafe and not want to continue the conversation. But I can avoid this by saying, “I don’t mean to suggest that you are not a great manager. Our department has been at least twice as productive since you have been in the role, and I am happy to come to work each day. I just think that we may need to look at how promotions are decided with an eye toward race and gender.”  

7. Restore mutual purpose

Another way that people begin to feel unsafe in a crucial conversation is when it starts to appear that we no longer share the same purpose.  Continually affirming the common goal can help avoid the fear of hidden agendas. When we take a step back to remember where we do agree, it’s easier to address the areas where we don’t.

My parents probably had the right idea in teaching me not to bring up difficult topics at parties with their friends. But what works at the dinner table in mixed company does not work to help us heal some of the brokenness among us. True, having crucial conversations with those we care about can be very challenging.  But by using these skills, we can “love our neighbor” in positive, practical ways that unite rather than divide. 

Mary Ann Steutermann

Mary Ann Steutermann is currently the director of campus ministry at Assumption High School, an all-girls Catholic high school in Louisville, Kentucky. A career educator, she has more than 20 years experience as an English teacher, assistant principal, and principal and does freelance writing on the side. She holds a bachelor's degree in English and two master's degrees in education. Mary Ann lives in Louisville with her husband and son.