How to Uncover Hidden Issues in Client Meetings

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.

The Art of Uncovering True Pain (That Most Sales Calls Miss) Ever notice how prospects rarely share their real problems upfront? "We need better email marketing" often means: "I might lose my job if we miss another quarter." Surface-level pain doesn't drive decisions. Real pain does. After hundreds of sales conversations, I've learned to go deeper: 1. Start with the situation: "What's happening right now?" 2. Explore the impact: "How is this affecting your business?" 3. Examine past attempts: "What solutions have you tried?" 4. Uncover consequences: "What happens if this isn't solved?” 5. Get personal: "How is this affecting you personally?" The prospect who tells you they're "just exploring options" might actually be lying awake at 3 AM worrying about their team's future. But they'll only share that if you earn the right through thoughtful questions. Sometimes the most valuable thing you can learn is that you're not the right solution. This process doesn't just make sales calls better – it makes your marketing better too. When you know what really hurts your customers, not just what they say hurts, your content hits home. Your emails get more replies. Your lead magnets solve real problems people care about. What's your process for finding out what really bothers your prospects? #SalesStrategy #ClientDiscovery #BusinessGrowth

A rep just told me: "I had perfect discovery. I uncovered all their pain points. Then they went dark." Here's the problem: Perfect discovery doesn't exist in textbooks. I've analyzed thousands of discovery calls, and I see the same mistakes destroy deals that should have closed. AEs treat discovery like interrogation instead of collaboration. They follow their framework religiously. They check every box on their qualification sheet. They uncover pain, budget, timeline, and decision-making process. Then they wonder why prospects disappear. Here's what they're missing: Discovery isn't ONLY about extracting information. It's also about creating insight. The worst discovery calls sound like this: Question, answer, question, answer, question, answer. The prospect feels interrogated. The AE sounds robotic. Nobody learns anything meaningful. Here are the 4 before and after discovery mistakes I'd recommend: 1. They Ask Questions Instead of Starting Conversations → Average: "What's your biggest challenge with your current solution?" (this would work better for inbound leads). → Elite: "I was just talking to another CEO in your space. They told me their biggest frustration was X. Is that something you're seeing too?" Start with insight when it comes to discoing outbound leads, not interrogation. 2. They Dig for Pain Instead of Exploring Impact → Average: "What problems are you having?" → Elite: "How do you know that this is an issue?" Don't just find the problem. Map the damages. 3. They Focus on Current State Instead of Future Vision → Average: "How are you handling this today?" → Good: "If this wasn't an issue anymore, what would success look like to you and your team?" Paint the picture of success, not just the struggle. 4. They Qualify Instead of Disqualify → Average: "Do you have budget for this?" → Elite: "What would have to be true for this to not be worth investing in?" Find reasons to walk away. It makes everything else more credible. —— The best discovery calls don't feel like discovery calls. They feel like business consulting sessions. When prospects say "I never thought about it that way," you're doing it right.

Often marketers chase messaging templates as though it will unpack a holy grail. As far as I know, most templates out there will do a fine job. However, it is vital to excel at articulating customer pain. Let me explain with an example from my domain: In vulnerability management, it’s easy to confuse operational challenges with true pain points. Let’s break this down. We often hear from our customers say: “𝘚𝘦𝘤𝘶𝘳𝘪𝘵𝘺 𝘵𝘦𝘢𝘮𝘴 𝘤𝘢𝘯’𝘵 𝘬𝘦𝘦𝘱 𝘶𝘱 𝘸𝘪𝘵𝘩 𝘵𝘩𝘦 𝘴𝘩𝘦𝘦𝘳 𝘷𝘰𝘭𝘶𝘮𝘦 𝘰𝘧 𝘷𝘶𝘭𝘯𝘦𝘳𝘢𝘣𝘪𝘭𝘪𝘵𝘪𝘦𝘴.” This feels like a pain point. It seems like they are describing a visceral and recurring challenge. But in reality this is just a surface problem. Teams are overwhelmed, but why does this matter? What’s the deeper impact? The real pain point looks like: “𝘋𝘦𝘴𝘱𝘪𝘵𝘦 𝘵𝘩𝘦𝘪𝘳 𝘣𝘦𝘴𝘵 𝘦𝘧𝘧𝘰𝘳𝘵𝘴, 𝘴𝘦𝘤𝘶𝘳𝘪𝘵𝘺 𝘵𝘦𝘢𝘮𝘴 𝘢𝘳𝘦 𝘣𝘭𝘪𝘯𝘥𝘴𝘪𝘥𝘦𝘥 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘩𝘦𝘺’𝘳𝘦 𝘤𝘩𝘢𝘴𝘪𝘯𝘨 𝘵𝘩𝘦 𝘸𝘳𝘰𝘯𝘨 𝘰𝘳 𝘭𝘰𝘸 𝘱𝘳𝘪𝘰𝘳𝘪𝘵𝘺 𝘷𝘶𝘭𝘯𝘦𝘳𝘢𝘣𝘪𝘭𝘪𝘵𝘪𝘦𝘴.” Alternatively: “𝘊𝘐𝘚𝘖𝘴 𝘴𝘵𝘳𝘶𝘨𝘨𝘭𝘦 𝘵𝘰 𝘫𝘶𝘴𝘵𝘪𝘧𝘺 𝘣𝘶𝘥𝘨𝘦𝘵𝘴 𝘰𝘳 𝘣𝘶𝘪𝘭𝘥 𝘵𝘳𝘶𝘴𝘵 𝘸𝘪𝘵𝘩 𝘵𝘩𝘦 𝘣𝘰𝘢𝘳𝘥 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘩𝘦𝘺 𝘤𝘢𝘯’𝘵 𝘥𝘦𝘮𝘰𝘯𝘴𝘵𝘳𝘢𝘵𝘦 𝘳𝘦𝘢𝘭 𝘱𝘳𝘰𝘨𝘳𝘦𝘴𝘴.” Often as marketers we are advised to use the same language as our customers but IMO that’s not always correct. First, if you ask what are your pain points, a prospect will never tell you. Second, it is much easier to describe the process than think of words to describe the pain. So as marketers, here are a few questions to ask to uncover pain points (it may be different for you based on your industry). 1/ Explain how you do this today 2/ How do you feel after each cycle 3/ What’s the impact of status quo Through these questions we are simply trying to get to the heart of their pain and understand the consequences. 𝘊𝘰𝘯𝘴𝘦𝘲𝘶𝘦𝘯𝘤𝘦 𝘰𝘧 𝘪𝘯𝘢𝘤𝘵𝘪𝘰𝘯 𝘊𝘰𝘯𝘴𝘦𝘲𝘶𝘦𝘯𝘤𝘦 𝘰𝘧 𝘪𝘯𝘦𝘧𝘧𝘪𝘤𝘪𝘦𝘯𝘤𝘪𝘦𝘴 𝘊𝘰𝘯𝘴𝘦𝘲𝘶𝘦𝘯𝘤𝘦 𝘰𝘧 𝘳𝘦𝘨𝘶𝘭𝘢𝘵𝘰𝘳𝘺 𝘧𝘢𝘪𝘭𝘶𝘳𝘦 𝘊𝘰𝘯𝘴𝘦𝘲𝘶𝘦𝘯𝘤𝘦 𝘰𝘧 𝘣𝘶𝘳𝘯𝘰𝘶𝘵 And so on.. In a nutshell, use any messaging framework, you will be ok but don’t skim on the due diligence to identify and go deeper on the pain because having the right emotions will separate you from the pack.

After analyzing 100's of discovery calls - I've noticed that even high performers miss a key ingredient when asking questions... Being specific vs. general Here are 4 examples: 𝗦𝗶𝘁𝘂𝗮𝘁𝗶𝗼𝗻-𝗳𝗼𝗰𝘂𝘀𝗲𝗱 General: "How many employees do you have?" Specific: "I saw you have 200 employees - how many are client-facing?" ----- 𝗣𝗿𝗼𝗯𝗹𝗲𝗺-𝗳𝗼𝗰𝘂𝘀𝗲𝗱 General: "Do you have problems with forecast reporting?" Specific: "How long does it take your team to generate pipeline forecasts each week?" ----- 𝗖𝗼𝗻𝘀𝗲𝗾𝘂𝗲𝗻𝗰𝗲-𝗳𝗼𝗰𝘂𝘀𝗲𝗱 General: "Are you missing targets?" Specific: "How often have you had to revise quarterly projections because the weekly forecasting process didn't flag declining deals quickly enough?" ----- 𝗣𝗮𝘆𝗼𝗳𝗳-𝗳𝗼𝗰𝘂𝘀𝗲𝗱 General: "Would faster reporting help?" Specific: "If you could reduce reporting time from 5 hours to 30 minutes, how would you reallocate your team's time?" ----- Here's a quick checklist to make any question more specific: • Have I included numbers? • Did I reference their specific process? • Am I connecting to business outcomes? • Have I inlcuded releveant timeframes? • Am I addressing specific roles/people? • Does it tie to industry-specific challenges? The difference? Specific questions uncover specific pain points. General questions - get general answers. Choose wisely.

The top 1% of salespeople don’t pitch harder. They ask better questions. If you want to uncover a customer’s real issues, here’s a 3-step framework I’ve used for decades: 1️⃣ Issue Questions Most sellers only ask questions they know the answers to. Big mistake. If you want to uncover hidden concerns, ask the questions you don’t know the answers to: “What obstacles are you facing to reach your targets this year?” “What concerns are on your mind given all the uncertainty in the market?” Let the customer lead. 2️⃣ Amplifier An amplifier isn't a question, it's a request for additional information.   So don’t jump in with a solution right away. Instead, use amplifiers: “Tell me more.” “Please expand on that.” Or stay silent. Silence is uncomfortable—but powerful. One client once leaned across the desk after I stayed quiet and said: 👉 “I’m not supposed to tell you this, but…” That never would have happened if I jumped in too fast. 3️⃣ Impact Finally, ask impact questions to identify the consequence: “What’s the impact if this is solved?” “What’s the consequence if it isn’t?” “What’s the personal impact on you?” Use this framework to deeply understand the customer’s real issues, concerns, needs, and problems. What’s a question that you’ve used that has worked for you? Tag someone who is working on asking better questions.