1.    skill employed in a shrewd or sly manner, as in deceiving; craftiness; guile.
2.    adeptness in performance; dexterity.
3.    showing or made with ingenuity.
4.    artfully subtle or shrewd; crafty; sly.
-source Random House Dictionary
Cunning exists in the world of strategy.  It is behind the animal nature of survival.  Archetypes, folk tales, and modern entertainment are full of stories of how animal cunning has tricked someone else out of an advantage: Loki, the cunning trickster, Jack, bringing down a giant, and cartoon rabbits outsmarting bumbling hunters.  At heart, we’re thrilled by the cunning.  We’re impressed by how they think on their feet, applaud their ingenuity, and we’re glad not to be the target. 
At its heart, there are two main themes in cunning: guile and ingenuity.  Guile is covert.  It is the crafty, animal nature striking to get ahead.  Instinct sees having the advantage of cutting someone else out as a way to increase our own ability to survive.  Cunning whispers to us: if I have more than they do, then I’m more likely to survive.  Yet, when it comes to thriving, the nature of strategy and covert action make partnership impossible.  Because who could trust a fox to be anything other than a fox?
The trick is to recognize the moment where strategies based in survival ultimately 
limit us.

At the same time, it would be foolish for us to say that cunning is a bad thing.  All attributes exist for a purpose in our personal and cultural evolution.  If we don’t survive, how can we make the evolutionary leap to thriving? The trick is to recognize the moment where strategies based in survival ultimately limit us.  Yes, we’re still alive, but at what cost? If survival means access to resources, is time better spent trying to collect all the resources ourselves, or could we “level up” even faster by collaborating with others?  At what point do we recognize that covert strategy interferes with the greater future we’re looking for?
Adeptness and ingenuity is the second theme of cunning.  There is skill in finding effective solutions that create an overall quality of life.  This side of cunning goes beyond survival, into thriving.  An ingenious solution to water purification allows millions of New Yorkers clean water every day from the polluted Hudson River.  An adept modification of radar technology saves innocent life and limb in Africa, with removal of hidden land-mines.  A cunning adaptation of the mirror in Indian hospitals allows for affordable treatment of phantom limb pain, so that amputees can have a quality life again.
When cunning focus evolves to adept ingenuity, the leap from surviving to thriving is made possible.