Dare Great Things

In the Gospel our Lord tells us to be as cunning as serpents and as simple as doves.  What does it mean to be cunning as a serpent and how could our Lord possibly want us to be cunning?  Anyone involved in leadership knows that leaders need to be strategic.  They need to think ahead of the curve and find a plan for achieving the great things that they set out to do.  Could this be what Christ meant?  How do Christians live and thinks strategically at the service of their love?