Which kind of leader are you?
Are you a glass half full kind of person or do you tend to look at things with a more pessimistic view?
How does this impact your ability to lead?
If you have historically been more of an optimist, will you always be optimistic?
This article from John A. Davis explores all of the above.
When testing strategic plans, deploy defensive pessimism, imagining all the things that can go wrong in the future. But when the task requires flexibility and had work toward uncertain goals, build teams with optimists.