Remember writing Christmas lists as a kid? “Dear Santa, I want a bike, a Nintendo, and a pony…” Simple. Direct. And completely missing the point. Because what we really wanted wasn’t the stuff—it was how we thought that stuff would make us feel. (The bike meant freedom. The Nintendo meant fitting in. The pony... Well, that was just ambitious.) Here’s the thing: your prospects are doing the exact same thing. When you ask them what they want, they give you their “Christmas list”: - Better software - Faster processes - Lower costs But just like that childhood list, they’re missing the real story. And most sales reps make a critical mistake: they take the list at face value and start pitching solutions. It’s like being the parent who buys exactly what’s on the list... only to watch their kid play with the box instead. The list isn’t the truth—it’s just the surface. The real gold is in what’s NOT on the list: - The frustration behind “better software” - The pressure driving “faster processes” - The fear underneath “lower costs” This is where asking the right questions changes everything. Instead of asking, “What’s on your list?” we ask questions that reveal the story behind the list: ❌ “What features are you looking for?” ✅ “What prompted you to start looking for a solution?” ❌ “What’s your budget?” ✅ “How is this challenge affecting your team right now?” ❌ “When do you want to implement?” ✅ “What happens if this problem isn’t solved by next quarter?” See the difference? The first set of questions gets you the list; the second set gets you the truth. Last week, one of my friends was talking to a prospect who “wanted better training software.” But instead of diving into features, the rep asked, “What made this a priority for you now?” The prospect paused… then shared how he’d just lost his third top performer in two months. How the board was asking questions. How his job might be on the line. That’s not a software problem. That’s not even a training problem. That’s a survival problem.