Questions to Identify Buyer Pain Points

When we dissect discovery calls, we hear this same motion almost every time - the buyer opens up about what they need, which prompts the seller to meet them with exactly how they can help. Perfect, right? Nope. We are SO eager to hear something that we can solve that we don't pause to ask the critical question - why? ***We know what you need, we don't know why you need it.*** What's the business pain? What's the cost of inaction? How much does this one issue impact dozens of people, dozens of times/day? How does this impact your goals for the year ahead? Is this enough of pain point that it's worth the trouble of changing? What's the monetization associated with the pain? Why is it important to change now? Have you tried to tackle this change before? And so on... Toss a sticky on your laptop and simply pause when you hear what they want. This is your moment to... differentiate significantly better qualify this opp get a host of details that will help you figure out how to best solve their challenges understand if you're talking to the right team ...and up your odds of advancing this opportunity #samsales

A rep called me frustrated. "I ask all the right questions, but they clam up after 10 minutes. Discovery feels like pulling teeth." I listened to her last call. She was doing everything "right" according to most sales training. Except for one thing. She was treating discovery like an interrogation instead of a conversation. Here's what I told her: Stop trying to get everything in 30 minutes. You're not a police detective gathering evidence. Instead, go deep on what matters most → their pain. Three questions that changed her entire approach: "What's driving this to be a priority right now?" "What happens if you don't solve this in the next 6 months?" "How is this impacting you personally?" Notice something? No questions about budget. No stakeholder mapping. No buying process. Just pain. Deep, emotional, get-them-talking pain. Here's what happened on next call: Prospect spent 20 minutes explaining their challenges. Shared things she never heard before. Got emotional about the daily frustration. Old Rep would've panicked: "I didn't get the buying process info!" New Rep said: "Based on everything you've shared, this sounds complex. Let's schedule another call to walk through how companies typically solve this." Prospect immediately agreed. Why? Because she proved she understood their world. The follow up call? Prospect brought their boss. Shared budget range. Outlined their evaluation timeline. All because the first call was about them, not about her information gathering checklist. Look, I get it. Sales methodology says you need certain data points. But prospects don't care about your methodology. They care about feeling understood. When you nail the pain, everything else flows naturally. The reps's close rate went from 18% to 29% just by changing her discovery approach. Same questions. Same product. Different mindset. Sales VPs: teach your reps to be consultants, not interrogators. The reps who master this thinking close bigger deals because they uncover the real emotional drivers behind every purchase decision. Ever noticed how your best discovery calls feel more like therapy sessions than sales calls? Strange, isn’t it? 😎 — How 700+ clients closed $950 million using THIS 6 step demo script: https://lnkd.in/eVb32BUx

Here are 5 *slightly-awkward* discovery questions I like, that signal you're different than the typical AE who's never thinking post-sales. That you're up to dig into what happens after the contract's inked. (Especially key if you're selling complex / enterprise deals.) 1. Unexpected Outcomes "Obviously, [ your main product benefit ] is the goal. But if your biggest win came in a totally different area we didn't initially expect, where would a win like that show up?" → Start it off with a win scenario, and get them thinking past the first use case into (potential) expansion areas. 2. Past Failures "Could you walk me through a time your team invested in something that technically worked, but didn't deliver the outcome? What happened?" → Finds their real definition of success, internal change management / political dynamics, and what metrics actually matter. 3. Resource Check "If this gets approved, what's one resource your team will have to 'borrow' from another team to make it successful—and how comfortable are you having that conversation?" → Cross-department dependencies are very real. Best to call out delivery roadblocks now, they haven't planned for later. 4. Executive Sponsorship "When you show this to [ exec sponsor ], what's 1 question they might ask, that you're hoping they don't... and what would your honest answer be?" → Often, what someone's telling you and what they know internally about an exec's concerns / skepticism are different things. 5. Six Months Later: "Let's say it's 6 months from now and you're in a QBR. Someone asks, 'Was this worth it?' What do you pull up on your screen to prove it was? And what would make you nervous about showing that?" → Helps you define real success metrics, and how they'll be tracked. Okay okay, I said 5 questions... but here's one more: 6. Plan B "What's your Plan B if this doesn't get approved?" → What's funny is I've found that my deals tend to be less "real" if there's no Plan B. Not the other way around. If something's truly important, there's always another option they're looking at. Could you see yourself testing one of these? PS, Olli the AI Agent we built is crazy good at crafting disco questions. If you'd want to put him to work on some of your toughest deals, drop a note & I can get you access.