Steps for How to Have Uncomfortable Conversations

When’s the best time to have a difficult talk with someone? How do you have uncomfortable conversations that you’re afraid to initiate?

Tough conversations are never easy to have, but sometimes they’re necessary for relationships. Not Nice by Aziz Gazipura has great advice for people afraid to say the wrong thing in these necessary talks.

Take a look at how to have uncomfortable conversations no one wants to have.

Practice When It’s Uncomfortable

The hardest time to speak your mind is when it’s uncomfortable—usually when you’re mad at someone or disagree with them. But, as in your professional life, your success and quality of life depend on you learning how to have uncomfortable conversations. Disagreement is inevitable and healthy. These conversations become easier when you don’t pit yourself against the other person. Your goal isn’t to win but to connect with the other person, to listen and be heard.

Why Are Difficult Conversations So Hard?

According to the authors of Difficult Conversations, difficult conversations are hard because there are actually three conversations going on at once, all of which provide opportunities to make predictable mistakes. 

The What Happened Conversation includes disagreement over what happened, who did what, and who’s right or who’s to blame. This conversation goes wrong when we assume our perception is “right” and that we already have all of the information we need. Consider a scenario where a supervisor says an employee has been late multiple times. The employee, on the other hand, believes his tardiness was due to uncontrollable circumstances and disputes the frequency cited by his supervisor. Both people are entrenched in their version of the story, leading to friction.

The Feelings Conversation usually goes unsaid and prompts questions about our own feelings: Are my feelings valid or appropriate? Should I acknowledge or deny my feelings? What about the other person’s feelings? This conversation goes wrong when we try to hide our feelings or we take them out on the other person. In our example, the supervisor feels frustrated, thinking the employee doesn’t value the job, while the employee feels attacked and wishes his supervisor was more understanding.

The Identity Conversation is an unspoken conversation that we have with ourselves. It circles around what this situation means about who we think we are. This conversation goes wrong when we ignore our true anxiety about what this conversation says about us. In this situation, the supervisor questions her leadership effectiveness and authority due to the perceived challenge, whereas the employee fears being labeled as unreliable and apathetic.

The authors argue that all difficult conversations contain all three of these conversations, and while we can’t change the challenges inherent in each one, we can change the way we respond to those challenges, and we can learn how to manage and address all three conversations to have better difficult conversations.

Gazipura recommends the following approach for handling any conflict: Begin by identifying your emotions, such as frustration or anger. Next, clarify what changes you want. For example, if you’re unhappy with infrequent communication with a close friend, think about what you’d prefer. Then describe the issue neutrally and express curiosity, saying something like, “I’ve noticed we don’t talk very often, and I’m curious to understand why.” Actively listen as the other person shares, and summarize their response to make sure you understand. Then, explain how the situation affects you. Finally, clearly state your desired outcome, but remain open to compromise. Just because you name what you want, doesn’t mean you’ll always get it.

(Shortform note: While Gazipura emphasizes the importance of speaking up, mastering the art of active listening—listening attentively to fully understand—is equally crucial, especially during challenging conversations. In Just Listen, Mark Goulston argues that by genuinely hearing someone out and empathizing with their perspective, you foster a connection that makes you more likely to influence their opinions and achieve a collaborative solution.)

Steps for How to Have Uncomfortable Conversations

Katie Doll

Somehow, Katie was able to pull off her childhood dream of creating a career around books after graduating with a degree in English and a concentration in Creative Writing. Her preferred genre of books has changed drastically over the years, from fantasy/dystopian young-adult to moving novels and non-fiction books on the human experience. Katie especially enjoys reading and writing about all things television, good and bad.

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