How to Reverse Engineer Sales Discovery

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

If your discovery questions start with “What’s wrong with…” You’re already losing. Old school discovery says: dig into their emotion. Modern discovery says: inspire until they believe. Most reps default to problem probing: “What’s broken?” “What’s hard?” “What’s blocking progress?” The intent is right. The framing is wrong. Buyers don’t want a therapy session. They want momentum. Here’s how to flip your discovery questions, and flip the outcome: 🔁 Instead of: “What’s your biggest challenge?” ✅ Ask: “What would a breakthrough look like this quarter?” 🔁 Instead of: “Why haven’t you solved this yet?” ✅ Ask: “What’s been missing from past attempts?” 🔁 Instead of: “What keeps you up at night?” ✅ Ask: “What gets you excited to win this year?” 🔁 Instead of: “Why now?” ✅ Ask: “What shifts if you nail this in the next 90 days?” 🔁 Instead of: “What’s the risk of inaction?” ✅ Ask: “What’s the upside of acting fast?” Language changes emotion. Emotion changes urgency. Urgency changes deals. Reps who master this don’t just ask better questions. They create better conversations. #sales #salesstrategy

One of my sales tactics made the Top 15 most listened-to episodes on 30 Minutes to President's Club Here's how you can use "Chunking Up" to close larger deals and get the attention of execs 👇 The problem: Most reps never meet the execs because they don't translate the problem into their language. They do all of this great discovery to find the pain for their champion. And their team. But they never "chunk up" to the business problem. ⛔️ Here's an example of where most reps mess up Let's say you sell a cybersecurity solution. And your goal is to get the CISO engaged in the deal. "Your team is spending hours manually prioritizing alerts as they come in. They're working overtime and experiencing burnout. We can help automate this so your team can get that time back for more strategic tasks." It's not terrible. But "saving time" and helping the team "be more strategic" are not a top priority for the CISO. ✅ Here's a better example Now let's take the specific problems shared previously, then "chunk up" to the business impact. Specific problem: "Your team is spending hours manually prioritizing alerts as they come in. By the time they find something critical, oftentimes days or weeks have gone by..." Executive problem: "By automating remediation, we can help you reduce the likelihood of a breach, avoid disruptions to the business, and increase stakeholder confidence in your org." ~~~~ Key idea: ALWAYS translate your conversations with champions to the business impact. You'll instantly level up your discovery and outbound messaging as well. Catch the episode with 30MPC for 14 other killer tips: https://lnkd.in/eUa6tnJG

What’s the fastest way to compress your sales cycle when selling large deals to Enterprise accounts? Here's what you DON'T do: - meet with department heads - demo your product and get them excited - have them attempt to sell upstream Instead, try using my Yo-yo sales framework. Here’s what it looks like. Step #1: Connect with power first, understand the most important problem(s) they need to solve, why they want to change, and the costs of not changing.If it’s a problem you can help solve, get their sponsorship for your discovery process. Ghost write a note they can send to their team to begin discovery Step #2: Meet with their department heads, get the real deal on what their day to day challenges look like, and grab some quotes which capture their biggest pain points. Seek to understand, not sell. Dig deep - understand the people, processes, and steps involved in doing the painful things which you can help improve or automate. Step #3: Package everything you’ve uncovered into an Executive Summary and Business Case and deliver back to Exec Sponsor and their team. Demo only what’s relevant. Close. Power compresses deals. This insight was key to me becoming the number one AE at Salesforce. It's how I went from averaging $240K/year my first four years to averaging $720K my final four years (including two years cracking 7 figures). Want to learn my process for closing huge enterprise deals? Tune-in to my full conversation on the 30 Minutes to President's Club podcast. Listen here: https://lnkd.in/gCJ4x7HZ

I bet your last stalled deal wasn't a product problem. It was a timeline problem. Last week I spent an hour with a client analyzing why some of their deals seem to sail through while others vanish into the void. The difference? Not their product. They were missing critical events. We identified the key to improving their sales process was attaching their solution to their prospects' existing priorities and deadlines. Here's what moves deals forward: → Find their critical event first. Before pitching, uncover their urgent timeline. "Why do you need to solve this by next quarter?" → Quantify the pain in dollars. "How much is this churn costing you monthly?" Once they say "$20K/month" your $5K solution becomes an obvious decision. → Schedule that crucial next meeting DURING the first call. "I'd like to prepare something specific for your situation. How's Tuesday at 2pm?" The best discovery calls focus on uncovering what's already important to your prospects and aligning your solution with their established priorities and timeframes. Stop chasing prospects who seem "interested." Start connecting with those who have deadlines that your solution can help them meet. Has finding critical events helped you close more deals?