Sales Questions to Encourage Client Reflection

Let’s go back to 2010. You’re selling iPods. The prospect says they’re using a Diamond Rio. Old school advice would say: “Time to explain the storage difference!” But that’s jumping to your solution. And your solution has no value without a problem. Instead, you respond in a calm, open tone: “How do you like it?” You’re not challenging. You’re inviting them to reflect. “Sounds like it’s perfect.” A neutral label. If it’s not perfect, they’ll correct you and now they’re telling you what’s missing. “Is there anything you ever wish it could do?” A gentle curiosity prompt. It bypasses defensiveness and gets them to consider possibility. Then you poke: “I know the Diamond Rio holds about 30 minutes of music, When you go on two-hour runs, do you just loop the same songs, or swap them out?” This isn’t a pitch it’s a flashlight. You’re helping them see a potential blind spot they may have normalized. If it resonates, and they feel the friction now you can step in: “You’ve probably looked into the iPod?” This presupposes awareness and respect. You’re not introducing something foreign you’re connecting the dots. If yes → “Sounds like it felt a little pricey.” If no → “With the iPod, you can run with 10,000 songs so you never have to repeat a track unless you want to.” The shift here is subtle but powerful. Your job isn’t to convince someone you’re different. Your job is to create space for them to notice something that isn’t working and realize they want different. Buyers have the answers. Sellers have the questions.

This clarifying question has CONSISTENTLY gotten me more valuable information from prospects. It’s so basic I wish I’d started using it sooner… Whenever someone tells me something they want or need that is remotely up for interpretation, I ask: “What does *that* mean/look like, to you?” Examples: CEO: “My number one problem is discoverability.” Me: “What does discoverability mean, to you?” CEO: “I want more people to know about us. I want my company to be the first thing people think of when they’re evaluating our category.” VP of Sales: “We need more pipeline coverage.” Me: “What does more pipeline coverage look like, to you?” VP: “We’re at a 2.5X multiple right now. We need to be at 5X to hit our revenue targets.” This question is effectively “mirroring” my prospect, but (to me) feels less manipulative. It also helps me: 1) further quantify the business impact, and 2) build more trust through understanding Try it on your next disco call. #sales #discovery #salestips

12 High-Impact Questions That Ignite Buyer Urgency. I was coaching a salesperson the other day who kept losing deals late in the sales cycle. Something kept slipping through the cracks. I asked, “Walk me through your discovery questions.” He rattled off the usual, generic, yet important, qualifying questions: ➤ How do you typically budget for this kind of project? ➤ What timeline are you working with? ➤ What solution are you using now? ➤ What keeps you up at night? I then asked if he ever used this question. “What happens if nothing changes over the next 6 to 12 months?” He said, “I’ve never asked that.” The next call, he did. The prospect paused. Took a breath. Then said, “Honestly? We’ll fall even further behind. I’m already under pressure to fix this or we risk losing the account.” That deal closed a week later because he asked questions that made it personal, emotional, and uncovered the cost of inaction. That’s why urgency can’t be told. It has to be discovered by the prospect through implication questions. You don’t need better scripts to create a better outcome. You need better questions. #sales #selling #presentations #salescoaching