You Had Your First Difficult Conversation…Now What?

Jen Dalton
4 min readNov 18, 2021

The holidays are fast approaching, and family gatherings can easily get hijacked by a variety of topics. In addition to being prepared, you may have already started the dialogue with a loved one during the last gathering, and you are facing them again for the first time since that tough conversation. Instead of starting from scratch, here are some ways that you can build on your earlier efforts, and hopefully continue the exchange in a productive, empathic manner.

Check-in with your feelings

It was a tough talk — you were trying to engage with someone you love on a topic that mattered to both of you, and it had been a source of tension. Whether it felt like a success or not, the effort was emotionally intense. How did you feel as the conversation happened? Were you calm or stressed? Were you fully present, or was it hard to stay in the moment? You may reflect back and realize that you could have entered the exchange with a different frame of mind, or done more to prepare, or you may find that you had a really positive experience that you’d like to build upon.

Debrief on the subject of the conversation

In the moment, it may have been difficult to absorb everything that was being said on the topic since your focus was split between the subject and the relationship. Take some time to think about the divisive topic itself. What changed for you based on what they said? Did you hear what they said, and did it expand your thinking on the topic? Did you ask questions to understand their point of view? Think of the original exchange as a teaching moment, and you were the student. What did you learn?

How did your loved one do?

The point of the first conversation was to listen, learn, and hopefully grow closer to your loved one. As you think back, how did they do in the conversation? Is there anything that you would have said differently or done differently based on how the other person reacted? Was your loved one upset, receptive, or engaged? Did they ask questions or shut down? Were you able to develop rapport and then find places or points in common as you went through the conversation? As you think back, would you have taken a different tack based on the reaction of your loved one?

Reflect and research

For the next round, you may want to take the conversation a step further instead of repeating the first exchange. To do this, you can try to think about what you still need to learn about the topic to increase your empathy and understanding of the topic and why it is important to your loved one. This is the opposite of confirmation bias — you should try to do additional research from diverse sources to gain insight and possibly respect for other perspectives. The goal is not to prove the other person wrong. Rather, you want to expand your understanding and gain context from multiple perspectives. You shouldn’t be surprised to find that there are more perspectives than yours and theirs; you may find a third, fourth, or dozens of additional perspectives on the same topic. Plan to go into another exchange showing that you have taken their point of view seriously and spent some time thinking about the topic.

Plan to go into another exchange showing that you have taken their point of view seriously and spent some time thinking about the topic.

Plan and prepare

If you had a productive exchange with your loved one, you hopefully took away some important information about that person, about yourself, and about the topic itself. For the next conversation, have some outcomes in mind. What are you hoping to learn, and how would you define success for your next conversation? Do you want to expand on the original topic, or explore another angle that was revealed the first time? For example, you may have learned more about the medical establishment’s debate about vaccination, but in your original exchange, you achieved important insight into your loved one’s perspective about the role of government in society that you want to explore. As with the first foray into controversy, you should have a plan for the conversation. In addition to the suggestions I’ve made before, you may want to consider reaching out to your loved one to propose a specific time and place for the conversation.

When it comes to difficult conversations, there is no one way to go. However, with loved ones, if you want to preserve the relationship and hopefully take the acrimony down a notch, you should consider an intentional approach with a focus on empathy and connection. To learn more about how to have difficult conversations, check out my latest book, Listen, How to Embrace the Difficult Conversations Life Throws at You.

Breathe and ask a question to start,

Jen Dalton

Jen Dalton is a personal brand specialist with entrepreneurship in her DNA. Her book, Listen: How To Embrace the Difficult Conversations Life Throws at You, is an insightful guide into navigating tough talks. She helps business owners and executives define how they show up as leaders, make the most of their strengths, and tend to their legacy, growth, and visibility. The author of two books, frequent speaker, podcaster, and “Purpose Sherpa,” Jen is a critical resource for any person or company that wants to define their brand and differentiate themselves in authentic, credible, and relevant ways to the market.



Jen Dalton

Reputation strategist for entrepreneurs & executives. Be a noisebreaker, not a noisemaker. #authentic #gutsy https://lnk.b