The Obstacle One of the biggest obstacles I run into when working with leaders one-on-one is breaking them of their masking habits. My first sign of trouble is usually a gigantic bookshelf filled with leadership, team building, and personal development books. Now, don't get me wrong here, I love to read and I advocate for the concept that leaders are readers. But, and it is a big but, you have to actually take the time to learn the lessons in those books and personalize them.