How to Identify Hidden Issues in Sales Conversations

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's a discovery question that gives me the ick (+ what I ask instead). "What's at risk if you do nothing?". "Doing nothing" implies the prospect is doing jack sh*t about a known problem. Here's an example. No CRO is "doing nothing" to address a pipeline generation problem. Instead, they might be: - Retraining the team on their sales tech stack - Hiring more reps - Facilitating in-house training - Asking Marketing to run demand gen campaigns - Rolling out a new, homegrown sales process - Sponsoring events, trade shows - Revising comp plans - Asking reps to hit the phones harder - Etc. It's why I seek to understand (early) the alternative categories of spend the prospect is considering to solve that known problem. Here's one way I ask about it: "Other than a team workshop with me, what other categories of spend or DIY solutions are you considering to address that problem?" Sometimes, I'll hear responses like: "We might ask Bob in L&D to run more of his prospecting sessions with the team." Now, I seek to understand what they like about the Bob option. Listen for belief/assumption statements. Ex: "Bob has been training the team for years. Plus, he knows our business." This answer gives me a clue to concerns that might become deal blockers later. Ex: the belief that an external trainer won't tailor the training to their business as well as Bob could. Now, I can tease out those concerns BEFORE talking about my solution. Trying to defeat an alternative solution we don't fully understand is kinda like trying to win a boxing match, blindfolded. If it's known problem, our prospect is doing SOMETHING. It's our job to uncover the real competition in the deal. Often, that real competition is how they're currently solving the problem today (aka status quo). It's not "doing nothing", as much as it's "changing nothing".

Most sales problems are not sales problems.  They are discovery problems. Bloated pipeline?  Deals dragging?  Prospects ghosting after proposals? It almost always tracks back to discovery. Because if your team is not asking the right questions  They are solving the wrong problems  For the wrong people  With the wrong urgency. And then we wonder why deals fall apart. In field sales, especially in technical spaces  Discovery is not a stage  It is the heartbeat of the sale. The mistake?  Most reps were trained to chase surface-level pain.  But pain alone does not close deals.  Clarity does. When I coach teams, we do not add twenty more questions.  We ask better ones.  And we actually listen. Questions like: What has already been tried that did not work?  What happens if nothing changes in the next 90 days?  Who else needs to believe this is worth solving? These are the questions that turn conversations into commitments. If your team keeps getting ghosted or stuck  Stop tweaking the proposal.  Start tightening discovery. If discovery is not uncovering urgency, risk, and decision dynamics  Let’s fix that.  I will help you sharpen what matters most.