Episode 42 – Getting Comfortable with Uncomfortable Conversations

42: Getting Comfortable with Uncomfortable Conversations| #walkwithme

“A person’s success in life can be measured by the number of uncomfortable conversations he or she is willing to have.”

“A person’s success in life can be measured by the number of uncomfortable conversations he or she is willing to have.”

– Tim Ferriss, The 4-Hour Workweek

About This Episode:

In this episode of “#WalkWithMe” I talk about how we can get more comfortable about having uncomfortable conversations, and share 8 tips I’ve learned that can help you not only get through those conversations but also move you forward by creating positive outcomes. 


How do you feel about having uncomfortable conversations? You know the kind I mean—the kind that affects you physically and emotionally. And, I’m sure all of us have some people who come to mind who seemingly enjoy confrontation and the energy of it. That’s not me. I’m in the category of people who naturally does not like confrontation. So, uncomfortable conversations are not at the top of my to-do list. 

I want to talk about this subject today because with all the necessary change happening around us, I think there’s going to be a lot of uncomfortable conversations happening. 

In the past 20 years of being an entrepreneur and leading teams, I’ve had to have a lot of uncomfortable conversations at all levels. At a high level, I can tell you the following about these kinds of conversations: 

  1. They are necessary. You can’t run from them.
  2. Uncomfortable doesn’t mean negative. In fact, in my experience, some of the most positive outcomes have come from uncomfortable conversations and have culminated in progress and growth. 
  3. The more you have them, the better you get at having them.

Here are some things that I’ve found that can get you through tough conversations, move you forward and turn a predictive negative into a possible positive outcome.

#1 – Approach a conversation with a genuine curiosity about the other perspectives.

Too often we go in so focused on getting our own point across that we shut ourselves off from getting other viewpoints. The most powerful thing we can realize is that there is value in other people’s experiences. 

#2 – Approach the communication style with respect and professionalism. 

How we choose to communicate means everything. The words we use might come across incorrectly and trigger negative emotions. Sometimes the intention and meaning are right, but the delivery of it causes confusion or anger. 

#3 – Don’t argue or debate how somebody feels. 

Learn to separate the topic at hand and don’t muddle it with how somebody feels. Learn to attack the topic, but never attack the person. 

#4 – It’s not about being liked

If you chase acceptance, affirmation or validation, you might find yourself not chasing what’s right. Not everybody is going to like you or like what you say. And that is OKAY. 

#5 – Listen. 

Actively listen. Don’t just wait for them to finish so you can share what’s on your mind. A really good habit is repeating the key points that they said so you can create alignment and let them know that you heard them

#6 – Be direct. 

Say what you want and what you mean. Don’t be passive aggressive or to beat around the bush. Back up with examples. 

#7 – Assume a positive outcome. 

Sometimes the outcome needs to happen because it’s a solution or it’s progress. This little flip in your mind can change the entire approach to difficult conversations.

#8 – Don’t put it off. 

Do it now. The longer you wait and stew over it, the more assumptions get stuck in your head and the more you create fear / worry about things that will never come to pass. Don’t shelve or bottle it up. 

What are things you’ve done to deal with hard conversations that have helped you? 

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