Uncomfortable Conversations

A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.
— Tim Ferris, The 4 Hour Work Week

I'm beginning to think this is the best piece of leadership advice I've ever read.

As a leader, when your company grows and the demands of your job become greater the need for crisp, direct and candid communication becomes increasingly important. At some level of scale, avoiding or delaying hard conversations with customers, prospects, peers, a boss, the board or direct reports can literally become disastrous. Decisions get delayed, expectations aren't set, people lack clarity, bad habits persist, and individuals and teams row in the wrong direction.

I've found that uncomfortable conversations, like most things, get much easier with practice. As you have more of these conversations you start to build an "uncomfortable conversation muscle" and these conversations seem much less daunting. When you start getting comfortable with the uncomfortable you really start to see the value. 

I'm not saying that one needs to walk around looking to have difficult conversations but a willingness to jump into a sensitive and thorny dialogue is crucial for success in leadership. Uunfortunately, the easy and natural thing to do for most people is to avoid or put off the hard conversations. The leader that doesn’t hesitate to go there quickly and is willing to address the elephant in the room will have a much higher likelihood of success than the leader that does what’s natural and easy.