Best Ways to Address Client Pain in Real-Time

Just got off the phone with a VP of Sales who missed a $300K deal because his team's show rate on cold calls is a lowly 30%... Let me ask you a question… Have you ever worked your tail off to book a meeting with a dream prospect, only to have them ghost you when it's time to show up? Well, one of my clients (the VP of Sales) just told me a horror story that probably sounds painfully familiar... Their SDR landed a meeting with a Fortune 500 decision maker after MONTHS of trying, but when meeting day came … CRICKETS. The prospect didn't show. They didn't reschedule. They went completely dark. That estimated $300K+ deal? GONE. And here's the salt in the wound. That VP discovered their COMPETITOR closed the deal 3 weeks later! Most reps are doing 2 things completely wrong: 1. They're booking meetings TOO FAR OUT (anything beyond 72 hours is a recipe for disaster without reminders and further confirmation) 2. They're sending calendar invites AFTER the call and just HOPING people show up (that's literally leaving money on the table) I've tested this with hundreds of clients and found a better way... 1. Get them to ACCEPT the calendar invite WHILE STILL ON THE PHONE: "I'm sending the invite now. Before we hang up, can you accept it so I know we're good for Thursday at 9 AM?" 2. Have them physically write your number down. “Just in case something pops up before Thursday at 9, let me give you my cell number. Have a pen handy?” When they physically write or type it down, it gives them another micro commitment. 3. Send a RESOURCE related to their specific challenges RIGHT AFTER the call. This proves you listened and gives them immediate value. BONUS points if you record a video message to humanize it even more. The hardest territory to manage is the one between your ears. Most reps are too afraid to ask for confirmation on the call. Be a bulldog. Get that confirmation. Your quota will thank you.

Last month, I worked with a client who used to 𝘥𝘳𝘦𝘢𝘥 sales calls. Sweaty palms, each call feeling like a painful pitch. Fast-forward a few weeks…they just closed their first $8K deal. No high-pressure tactics, no gimmicks. Here’s how they flipped the script: 1/ They got crystal clear on client pain points:   ↳ Spent the first 10 minutes actively listening.   ↳ Asked questions to dig further into the root problem. Result: Built trust and uncovered the client's real issues. 2/ Built unshakeable confidence in their offer   ↳ Prepared responses to common objections.   ↳ Answered with real results that matched client goals. Impact: Their belief in their solution was contagious. 3/ Owned what made them different ↳ Listed 3 unique strengths that set them apart. ↳ Naturally aligned with what the client needed in a partner. Outcome: Clarity let clients see why they stood out - no overselling. The result? Every call felt effortless. Clients leaned in. Conversations shifted from "selling" to solving real problems. Here’s my question: Are you 100% clear on the problem you solve and who you solve it for? Because if you’re not—clients can sense it a mile away. Most people don’t need a "better" offer. They need better clarity. Agree?

I’ve developed a repeatable framework that consistently gets prospects to open up about pain points and acknowledge the impact. 1. “Menu of Pain” Questions: Instead of asking generic things like “What keeps you up at night?”, I list the three most common problems I solve and let the prospect choose. I’ll say: “Typically, when I speak with others in your role, they’re facing challenges like A, B, or C. Which one is most relevant for you?” By giving them a menu, I keep the conversation focused, demonstrate expertise, and make it easier for them to open up. 2. The “Magic Moment” Question: Once a problem surfaces, I’ll ask: “When was the moment you realized that was a problem?” That question always gets a story. And stories give me context, emotion, and insight into what actually triggered the pain. It’s one of the best ways I’ve found to connect tactical issues to their larger business implications. 3. Humbling Disclaimers: I’m not afraid of bold questions, but I always preface them with humility. I might say: “I know this may be a direct question, but would it be ridiculous to assume this issue needs to be fixed to hit your goals this quarter?” That disclaimer softens the delivery, makes the question palatable, and gets me honest, candid answers. I’ve found that you don’t need 20 impact questions - one or two, framed the right way, can uncover massive problems that drive urgency. 4. Transparency on Next Steps: At the end of discovery, I want transparency, not ambiguity. I’ll often say: “People usually take these calls for one of a few reasons - just researching, needing to solve something immediately, or somewhere in between. Which bucket are you in?” That way, I either secure real next steps with someone serious or I gracefully qualify out. For me, it’s better to know the truth than chase a deal that isn’t real. Stay curious.

For the love of God… be...patient... A few years ago, I was on a call with a buyer who casually mentioned a challenge they were facing. Before they could even finish their sentence, I pounced. 🚨 “Oh, yeah - we see that all the time! Let’s jump in and take a look...” 🚨 I launched straight into our product, rattling off features like I was reading a teleprompter. I thought I was crushing it. And then? Silence. The buyer gave me a polite nod, said they’d “think about it,” and never called back. I had just committed the #1 sin in sales: solving too soon. It's the the sales equivalent of a fire extinguisher Most sales reps are like overeager camp counselors. They see a spark - a problem the buyer mentions - and instead of letting the fire build, they grab the extinguisher and put it out immediately. 🔥 Buyer: “Yeah, we’ve been struggling with forecasting accuracy.” 🚒 Sales rep: “Oh! We have an AI-powered forecasting engine that...” STOP. Let the fire spread. Because if the problem doesn’t feel big enough, the solution won’t feel necessary. So what do you do instead? → Here's my “Let It Burn” Framework: Next time a buyer mentions a problem, resist the urge to solve it. Instead, dig deeper. Ask pain-amplifying questions like: ✅ “How long has this been an issue?” (Time pressure) ✅ “What have you tried already?” (Exposing failed attempts) ✅ “What’s this impacting right now?” (Connecting it to real pain) ✅ “What happens if this doesn’t get fixed?” (Creating urgency) Make them sit in the problem. Make them feel it. Because no pain = no urgency. No urgency = no deal. Most deals aren’t lost because your solution isn’t good. They’re lost because the problem never felt urgent enough to fix. So next time you hear a buyer mention a challenge? Shut up. Then dig deeper. The bigger the problem feels, the easier the close.