The Courageous Leader

5The Courage to Be Confident

Imagine if birds only sang when heard. If musicians only played when approved of. If poets only spoke when understood.¹

—Mark Nepo, The Book of Awakening

Kellie was a first-time manager who, like many, was just trying to figure it all out. She loved her company, her team, and most of all, the work she did. Kellie was known by others for her contagious combination of positivity and a willingness to collaborate. When I first started working with Kellie, she was in the beginning stages of creating boundaries with others and learning to delegate. Because she was so willing to help others, at times she would struggle with saying yes, when in reality she wasn’t prepared to take on the additional work and even when she really wanted to say no. To make matters worse, she had a very challenging employee who was making her rethink her decision to become a leader.

During a conversation in which Kellie was sharing some of her frustrations with the challenging employee, I said to her, “Kellie, leading people is hard. We all feel this way at times. It’s not just you.” Her eyes watered up and, on the verge of tears rolling down her face, she brushed them away and exhaled relief. Kellie needed validation that what she was experiencing didn’t mean that she was incompetent or incapable, even though she may have been feeling that way.

Fast-forward a few years later, Kellie and I met to catch up on her development goals. This time, though, our conversation was dramatically ...