We all have them, and we usually dread them—difficult conversations. These can happen daily at work or with family and friends. Preparing for these conversations can cause worry, anxiety, and sleepless nights. But there is an art to engaging in difficult conversations with grace, vulnerability, and a goal of maintaining or increasing depth in the relationship moving forward.

Too often to count, I have entered a difficult conversation with a hidden agenda, a plan, or a preconceived outcome. When entering in with my own game plan, I can tell you that the execution and the end of the conversation didn’t go well. Outcomes included short-sighted goals, frustration, and, most often, a barrier developed between the other party and me.

When preparing to lead with grace in tough conversations, I keep Nelson Mandela’s words in mind to frame the situation: “I never lose, I either win or learn.” Thinking about difficult conversations as ways to learn—rather than lose—can change the rules as well as the outcomes. Equally important, entering into conversations without a sense of winning or losing gives you the freedom to misstep without feeling like a failure.

In my many epic fails with difficult conversations, I have learned a new game plan, one in which I don’t have a preplanned outcome. My new plan includes multiple plays that help me in many aspects of my communication game—because when communication fails, relationships falter.

Play No. 1: Do I Want to be Liked or  Do I Want to Lead?

Leaders both new and seasoned can run into this trap when thinking about entering into a tough call or conversation. They may ask themselves, “Am I avoiding this conversation, or covering it up because I am worried I won’t be liked, or that I will hurt someone else’s feelings?” This thought process has made me sugarcoat something that became too distorted to understand. Making sure that you keep at your core what you are trying to accomplish is key so that when popular opinion attempts to get in the way, you can stay the course.

The difference between being liked and leading is not just about the purpose of the message or the delivery. Leading also means allowing others to sit with the discomfort and process a conversation without circling back right away or diminishing the message by flooding the person with positive accolades. Brené Brown’s “Let’s Rumble” offers conversation starters and questions that can provide guidance. You need to make statements such as, “Help me understand,” and “Tell me more.” These statements allow you to sit in discomfort without distorting or distracting the conversation’s main purpose.

Play No. 2: Keep It Professional and Don’t Take It Personally

I used to think that after every hard conversation, people hated me. Honestly, I was way too hard on myself. But, trust me, their feelings aren’t always about you. Too often, we read way too much into another person’s reactions.

If you are concerned about how the message will be received, practice prior to delivery. Write it down, read it aloud, and—if appropriate—practice with a colleague or supervisor. My default when I am nervous is to ramble and fidget with my hands. How do I know that? My HR director and the high school principal gave me that feedback after two separate tough conversations.

The High Conflict Institute based in San Diego utilizes the BIFF approach. BIFF stands for brief, informative, friendly, and firm, and this method can be used during written or in-person conversations. A few years ago, our staff engaged in this process by bringing stories or examples of perceived hostile emails. As a team, they applied the BIFF strategy to the emails and reported back their response. As a school, we started to utilize the strategy and lean on each other before responding in a way that would put up more barriers than bridges.

Opening yourself to feedback after delivering a message also shows that you are aware that you can learn from the other side of the conversation, not just as a receiver but as the sender of a tough message. Be careful not to personalize the feedback. Remember to keep it professional and if you feel it turning personal, check out play number three.

Play No. 3: Focus on What You Can Control

No matter how well you prepare, how much time you give, or how hard you try, you cannot manipulate, control, or direct others’ responses. What you can do is model what you want to see from others. If someone is yelling at you, take a deep breath and respond in a calm, quiet manner. If a student is angry and upset, recognize the emotion and name it without judgment.

One way a tough conversation can go wrong before it starts is if you walk into it agitated, upset, or anxious. I ensure that my own emotional state is in check before trying to have a challenging conversation. One strategy I use if I notice I am not self-regulated before walking into a conversation is: I stop, take three deep breaths, and then enter the room. Another option is to write down what you are worried about before you begin. Naming it gives you a chance to tame that emotion so you can be fully present, calm, and convey kindness regardless of what message you receive. I have harnessed a “mind dump” as a framework in preparing for conversations. Taking the time to really figure out what I want to say, or why a situation or circumstance is bothering me, is important to ensure the tone and tenor of the conversation are aligned.

A colleague of mine says, “If I am uncertain of their why or reasoning, I need to lean into what they aren’t saying.” Body language and environmental cues need to be considered, as do circumstances in students’ or staff’s personal lives that might be impacting their responses.

Play No. 4: Keep in Mind the Purpose of the Conversation

Empathy for others when leading allows you a glimpse into a broader perspective of actions, interactions, or reasons for the behavior you are addressing. The foundation of this work includes finding value in the person before the hard conversation. Keep in mind that the person on the other side of the conversation has a point, a plan, and a purpose—no matter how different it is from ours. Recognizing that is essential when framing the ultimate goal of the conversations.

To support a student, to enhance a relationship, to build a foundation of trust and understanding in which to grow, keep in mind the long-term prize. Then, any short-term setbacks don’t seem so insurmountable.

The Final Play: Move Away From Winning and Toward Learning

Some conversations are difficult and challenging, and at times it’s the last thing people want to do. However, through every difficult interaction, conversation, and discussion, I have learned. This learning continues to help me grow and develop into a better leader, mother, friend, and spouse. When a difficult conversation is in your future, I challenge you to see it as an opportunity, not an obstacle.

Jessica Cabeen is the principal at Ellis Middle School in Austin, MN. She is the author of Hacking Early Learning, Lead With Grace, and Unconventional Leadership, and co-author of Balance Like a Pirate.

Sidebar: Resources

Try doing a “mind dump” when preparing for a difficult conversation.