Circumspect
/ˈsɜːr.kəm.spekt/ adjective mediumCareful and cautious, especially about weighing possible consequences before acting.
Being circumspect about the merger, the board demanded three independent audits before signing anything.
Memory Trick
'Circum-' means around, and 'spect' means to look (as in 'spectacle') — to be circumspect is to look all around a situation before ever taking a step.