"The unexamined life is not worth living." – Socrates

As a leader what does this quote mean to you? And why should I care?
First you care because as a leader you must continually examine where you are and where you are leading yourself and others.
My opinion is that Socrates means is if a person is not open for others to question his or her thoughts and action, or lives in denial of the motivations that prompt his or her thoughts and action, then it is a waste of his or her life. Such a life is a superficial act, revealing nothing new, nothing unique. Such a life is not "real." Socrates also suggests that, in addition to the above response, the "unexamined life" refers to a life whose purpose has never been questioned; a life that has never been analyzed, inquired into or inspected; a life that has not been appreciated beyond face value. By suggesting this, Socrates gives praise to questions such as, "Is there more to reality than that which we can see and touch?;" "Am I living my life according to my own rules, or the rules set for me by others?;"