Circumspect

circumspect [ SUR-kuh'm-spekt ]
[ adjective ]

MEANING :
1. (adj.) cautious or watchful and discreet
2. (adj.) mindful of the circumstances and consequences
3. (adj.) prudent

USAGE EXAMPLE 1 :
The confident trickster had never been caught because of his circumspect behaviour.

USAGE EXAMPLE 2 :
Defense Secretary Robert Gates praises former President Reagan for being "circumspect" about putting American troops at risk.