Insights on business,
life, and leadership —
right in your inbox!

Uncomfortable Conversations

March 10, 2020

Almost 15 years ago, I was in college at the University of Georgia. (Just writing that makes me cringe a little—it makes me feel old!)

When I was a junior, I remember trying to raise money for a charity I was involved in. And as the uninhibited dreamer of the group, I hatched a crazy plan. I decided that I was going to call Coach Dooley and ask him if our organization could host a fundraiser at his house. 

Now, for those of you who don’t know who I’m talking about, Vince Dooley is a living legend at UGA. He is a Hall of Fame football coach who led the Georgia Bulldogs to win six SEC Championships and one National Championship in his career. Long story short, he was the most famous person living in Athens at the time, and I was about to call him to make a HUGE ask.  

Not only was I asking him to give us his time by appearing at this event, but I was also asking him if we could host this event at his home—a place usually reserved for much more important university events than a fundraiser organized by college students seeking to raise money from other college students (obviously not an ideal group of donors). 

Want to know the craziest part of this plan?

It worked. Coach Dooley said, “Yes,” and I’ve been blessed to have a special relationship with Vince and Barbara Dooley ever since. 

Isn’t it funny how little children have no fear of asking for whatever they want? When your child says something to you, they aren’t worried about how you’re going to feel about it. Yes, they certainly need to grow in empathy and restraint, but for the most part, their honesty and confidence is refreshing and even helpful. 

Unfortunately, something happens to us as we get older. Our fear of rejection grows exponentially. Maybe this is a result of our personal experiences, or maybe we’re too concerned about the way we appear to others. Either way, we become less willing to have important, uncomfortable conversations—to make the big asks or to say the crucial things that are not easy to say.

Now before we go any further, I want to make something clear: This blog is not promoting a lack of social awareness or sensitivity.  It’s about this principle that author and entrepreneur Tim Ferriss communicates so perfectly: “A person’s success in life can often be measured by the number of uncomfortable conversations he or she is willing to have in a day.”

Tim would argue that these people are successful because they are willing to get out of their comfort zones  and gain an opportunity to experience the extraordinary. I think he’s right. Said another way, they are willing to exchange stability for significance.

So here’s my challenge to you and to me today: have the uncomfortable conversation.

Pick up the phone, call the client, and make the hard ask.

Own your mistake, call your friend, and tell them you can’t come to their event because you’ve overcommitted yourself.

Schedule the meeting, sit down with your teammate, and give the constructive criticism he or she needs to do better work and to grow professionally.

Fine-tune your resume, gather your references, and call your contact at the company where you really want a job.

I’m not promising it will always work, but if you never initiate the conversation, you’ll never know. And even if you are rejected, you’ll realize it doesn’t hurt nearly as badly as you thought it might.

What uncomfortable conversation do you need to have? 

Click out of this email, minimize your browser, pick up the phone, make the call, and initiate it. You never know the amount of good that could come from it.


Insights on business,
life, and leadership —
right in your inbox!