Identifying Hidden Customer Pain Points Through Interviews

One of the worst ways to handle discovery: (I know because I've done it) Treating it like an interrogation. Asking back to back questions. Not breaking it up with conversation or context. I used to run through my list of questions like a robot. Check, check, check. Getting my answers, but missing the actual conversation. The prospect would start giving shorter responses. Their energy would drop. And I'd wonder why I wasn't getting any real insights. Sound familiar? Here's the easy way to fix this: 1. Repeat back what they said "It sounds like there’s a ton on your plate, so you don’t have time for __. How is *competitor* supporting you with that?” 2. Ask second-layer questions Not just "What's your biggest challenge with ___?" but "What do you feel like is keeping you from reaching that revenue goal?" 3. Share relevant context "That's interesting - we've seen similar issues with other customers in your industry. Here's what we've learned..." 4. Show genuine curiosity "That's surprising to me. Can you tell me more about why you don’t think ___ is working well?" The difference is dramatic. A few weeks ago, I had an initial demo that completely transformed because of this approach. The prospect told me what their revenue goal for this year is. Instead of just noting it and moving to my next question, I paused. "That’s an ambitious goal. What exactly are you putting in place to achieve that?" I was genuinely curious to know. What followed was a 10-minute conversation that revealed: - What they currently have in place (what’s working, and what’s not) - Their current program ROI (which was alarming for us both) - Their micro goals (that make up the overall revenue goal) - Lack of capabilities with current vendor - Their exact pain points Gold mine. Had I just flown through questions, I would have missed it all. After our conversation, she followed up with the SDR, "thanks so much for reaching out, we had such a great conversation!!" Great discovery isn't about checking boxes. It's about creating a conversation where prospects feel heard. Where they're comfortable sharing the real story. Not just the surface answers. The best sellers aren't the best questioners. They're the best listeners. What discovery technique has made the biggest difference in your sales conversations?

I love how much enthusiasm and interest came from my last post on Jobs-to-Be-Done. But before diving into frameworks, I want to rewind and talk about some key fundamentals when it comes to customer discovery interviews. Because here’s what I’ve seen over and over again: Teams and founders get excited about an idea. They talk to people and show their prototype. People are kind and encouraging. And suddenly…it feels like validation. But polite nods and positive reactions aren’t actual validation. If you’re working on something new, your first job is to validate the problem, not the solution. And when you’re looking to validate the problem, here are some things to keep in mind: 1. Ask about the past Don’t ask people to imagine the future. Start with: “Tell me about the last time you …” That’s where the truth lives. When people are asked to predict the future, they’re often wrong. It’s Friday — did your week go exactly as you had predicted? 2. Avoid leading questions Skip the yes/no. Skip assumptions. People are often agreeable and may say “yes” — even when it’s not a real pain point. ❌ “Do you struggle with organizing student data?” ✅ “Walk me through how you organize student data today.” As they go through their story and you dig in, that's how you find the real struggle moments. 3. Dig into their story Don’t stick to a script. Get more context around the situation and follow the emotion. Bob Moesta calls it “following the energy” — when you hear a shift in tone or a moment that clearly mattered. Ask follow-ups like: “What happened next?” “Where were you? Who else was involved?” “What else have you tried?” That’s where the real insights live. 4. Look for signs of workarounds Spreadsheets, post-its, manual processes — all signs of friction. It’s in these struggle moments that valuable problems often appear. 5. Don’t pitch. Stay curious. Your mindset should be more like a journalist than a salesperson. You’re trying to understand, not convince. Be surprised. Be open to your assumptions being wrong. The Mom Test by Rob Fitzpatrick is a great getting started resource around this topic with even more tips. I’ll dive into JTBD frameworks soon, but this is the foundation that makes any customer discovery interviews more effective—especially when you’re building something new and innovative. Any others you’d add? #CustomerDiscovery #ProductDiscovery #JTBD #CustomerInterviews

Forget fancy ICP slides…I uncovered surprising customer pain points with a simple Nextdoor post… Most marketers think we know what our target customers want by creating fancy ICP slides… But the hard truth is market insights don’t always come from data reports, surveys, or those fancy ICP slides. Sometimes, they come from talking directly to the people who will actually use your product. 🤝 Yet so few marketers actually practice the art of talking to real customers. Sure, we all claim we do but how often do we really dive deep with our audience? Recently, I tested a new approach by posting a geo-targeted inquiry on Nextdoor, seeking recommendations from local institutions about a SaaS platform. The response was incredible - get this Over 13.3K views, 70+ comments, and a ton of engagement! 🎉 From those comments, I followed up with around 35 potential "customers" and managed to schedule follow-up calls with 15 of them. After speaking with these 15 interested organizations, I gained some valuable insights that every product company can leverage: 1. Refine Product-Market Fit through Direct Conversations Instead of relying solely on data trends, engage directly with potential customers. One-on-one discussions reveal pain points, preferences, and specific needs you might miss in broader research. This approach helped me understand which features and ease-of-use factors would truly resonate. 2. Validate Pricing Models with Real Pain Points Many SaaS companies base pricing on competitor analysis, but why not test pricing structures directly with your target audience? My calls helped uncover the price points and value propositions that align with actual budget constraints. This hands-on feedback is gold for creating a pricing model that meets customer expectations. 3. Tailor Marketing Channels Based on Customer Preferences Don’t assume where your customers spend their time; ask them! These conversations highlighted that while social media presence matters, the importance varies by industry and demographic. SaaS companies can adapt their content strategy to align with where their audience is most active, amplifying each channel’s impact. From this simple Nextdoor post, I was even able to create a 7-Step Competitive Analysis Chart based on real customer feedback. Lesson learned: If you want real insights, skip the assumptions and go talk to your audience. Sometimes, your best product market fit (or expansion) is just one conversation away! #hustle #marketing #marketinginsights #saas

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

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.