The Importance of Uncomfortable Conversations

Apr 16, 2021 | Blog

How does your garden grow

The Importance of Uncomfortable Conversations:

How to Have Them & How to Grow from Them

If you read my blog regularly, you know I’m all about positivity  – especially positive feedback. As a leader, I don’t encourage criticism because it tends to be mostly negative and unproductive. That said, some of my most pivotal moments have come from uncomfortable conversations. I’m not talking about salary negotiations or other unpleasant logistical conversations. I’m talking about open and honest discussions about behavior and performance from friends, peers, and leaders.

These types of uncomfortable conversations are the most important and challenging conversations one can have as a leader, and as a human for that matter. I’ve participated in a number of uncomfortable conversations in my lifetime, and the productive ones have a few things in common:

  • Their focus is purely on the situation or behavior at hand.
  • Their sole purpose is to improve the situation or behavior.
  • Open and honest communication is maintained throughout.

I discuss these lessons and other tips for becoming a better leader in my free Ebook, 5 Heroic Leadership Skills

Today, however, I’d like to talk about the conversations where I was on the receiving end of the discomfort. While the point of those uncomfortable conversations may have been to improve interactions with my friends and peers, or to make me a better person, that didn’t mean they were a walk in the park. Some were about small changes, many were about moments of ignorance, and a few called for serious time and reflection to modify bad habits or routines.

It took me years to become less defensive when I received feedback. In fact, one of my earliest uncomfortable conversations was about being defensive. Because my boss was willing to have that uncomfortable conversation with me, it opened me up to receiving and even seeking out feedback that improved my life. When I look back, I realize there were a few reasons could lower my guard and take that feedback:

  • The issue was explained to me privately.
  • The issue was addressed immediately after it happened. 
  • It was posed as a question, not an accusation.
  • We were able to get to “the why” of the issue together. 

If you tend to get defensive, try to keep in mind: if someone is willing to come to you with open and honest feedback, and earnestly wants you to grow, it’s probably very important to them. Most people have a fear of confrontation, and if they are willing to work through their own fear to help you grow, they most likely value you. If this is a friend coming to you, it probably means they want to make your relationship more comfortable. Otherwise, they would ghost or avoid you, tolerating the behavior only when necessary. If it’s a peer, they’re likely trying to improve their work environment before taking other steps like talking to a boss or looking for a transfer. If they didn’t like or respect you, they’d skip that step entirely. If it’s a leader, they most likely want to see you succeed. 

So, if people really want the best for us, and the end result is likely to be positive, then why are the conversations so uncomfortable? A few reasons: 

  • Humans aren’t the best communicators
  • We make assumptions. 
  • We don’t always take feedback well, even when it is well-intentioned but should. 
  • Even well-intentioned feedback can be hard to take, when ego and self-image get in the way

At the end of the day, it’s up to you what you do with honest and constructive feedback, and whether you’ll dismiss it or make something of it. If you apply it, it’ll make you a better friend, a better co-worker, and in the end, a better leader. This is why it’s so important to have those uncomfortable conversations for yourself, and in turn with the folks you lead and want to succeed.

What do you think about the importance of uncomfortable conversations? Let me know in the comments below. 

Are you ready to lead and succeed? Join me on a Leadership Retreat! Also be sure to check out my podcast and YouTube channel!



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