Uncomfortable Conversations

An article in LeaderTalk got me thinking about some things. One of the contributors wrote of his new-found habit of starting conversations with strangers and learning from them. It reminded me of something Tim Ferris wrote in his book, The 4-Hour Workweek. To paraphrase the book - a person's success is related to the number of uncomfortable conversations he or she is willing to have.
I found that interesting, and along with the LeaderTalk article, have decided to pursue that a bit further. It seems to me, in this age of political correctness and more volatile society, that we sometimes avoid difficult conversations at the expense of growth or truth. Overcoming the fear of rejection or failure that accompanies talking to strangers or having uncomfortable conversations with anyone is the first step in achieving success at this type of communication. I would be interested to hear of success or learning that has occurred from an experience with this.