Spy out the land Definition 1 of 2Pro Tip 1/3Figurative Sense The phrase is often used metaphorically to mean careful examination or preparation. I need to spy out the land before starting my new job. Pro Tip 2/3Research Implication Implies doing research or getting a feel for a situation before acting. Let's spy out the land before we propose the new marketing strategy. Pro Tip 3/3Preparation Essential Suggests thorough preparation is essential for success. The team decided to spy out the land to better tailor their pitch to the investors.