A Beginners Guide to Uncomfortable Conversations

I’m not sure how to start this one. A lot of things have happened since the last blog post. Some not so serious stuff, like a Youtuber beating up a recently retired multi-promotion MMA champion. And some really serious stuff, like Derek Chauvin being found guilty on all counts, causing all kinds of conversations that, honestly, should’ve started a long time ago.

But they were uncomfortable.

Threads Podcast: Life Unfiltered is a podcast with a large focus on the importance of uncomfortable conversations. Two white, suburban, Christian men started this podcast a few years ago with a much smaller worldview, which has opened immensely thanks to the uncomfortable conversations they’ve had with recovering drug addicts, people of faith, people who’ve lost their faith, grieving parents, people from the LGTBQ community, people who speak on mental health, race, the good and the bad sides of religion, and personal hardships and shortcomings. These uncomfortable conversations have led to personal change, growth, and wisdom. And we’d like to encourage you to start having a few uncomfortable conversations of your own. Is there something you’ve always wanted to talk about with your parents, spouse, friend, or even coworker, but you were too scared or anxious to go through with it?

Well, here’s some advice on…

How to Have an Uncomfortable Conversation

It’s always a good idea to have some ground rules. Pyschology Today lays out some excellent ground rules, here are a few:

  • Speak directly to the other person(s).
  • Speak as calmly in a matter-of-fact tone as possible.
  • No interrupting.
  • Make sure you understand what the other person has said before you respond.
  • Approach the conversation with openness and an interest in problem solving, rather than needing to be “right.” 
  • Do not walk away or leave the conversation without the other person’s agreement. Allow for the possibility of time-outs.
  • Take responsibility for feeling the way you do, rather than blaming the other person. 
  • Drop your assumptions.

Across the rest of my research on this, I came upon several common things:

  • Go into the conversation with a positive mindset, and a positive expectation for the outcome.
  • Focus on listening and understanding the other person, asking questions when you aren’t sure you follow. It’s not important to be liked in these scenarios, the most important thing is that you are trying to truly empathize, even when you disagree.
  • And when you disagree and/or are extra uncomfortable, acknowledge it. Say, “This is difficult to talk about,” or “It sounds like we agree up this this point, does that sound right?”
  • Use as much I/We language as possible, it shows a willingness to be open and cooperative.
  • Don’t stop talking–it leads to more awkwardness.
  • Let a person know before you tell them something that might be hard for them to hear.
  • Don’t dance around the issue–be direct.
  • Come to a mutually agreed upon closing point–no stopping out of discomfort.

And, whenever possible, have these conversations in private. Or on a podcast…like Threads Podcast: Life Unfiltered. OK, maybe you aren’t ready for that, but you could listen to the show and get an idea how a good–yet still uncomfortable–conversation goes down.

Take care!


Christopher Tallon

Christopher Tallon writes, podcasts, and…wait a second. Are you actually reading this? High fiveFollow me here:

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