Why Founders Keep Asking the Wrong Questions in Customer Interviews I've been mentoring early-stage founders for a long time. One of the first books I put in front of all of them is The Mom Test by Rob Fitzpatrick. The core lesson: most founders ask questions that get polite answers, not honest ones. "Would you use this?" tells you nothing. People don't want to hurt your feelings. The book teaches you to ask about real behaviors instead — past experiences, actual workarounds, real decisions. Questions that can't be answered with a comfortable lie. The problem is, founders read it, get it, and then walk into their next interview and ask: "So does this solve a real pain point for you?" Every. Single. Time. Knowing what a good question looks like isn't the same as being able to generate one on the spot about your specific product and customer. So I built a free tool to close that gap: MomTestQuestions.com You describe your product and your target customer. It generates a set of high-quality interview questions built on Mom Test principles — questions about behavior, not opinions. Ready to use in your next customer conversation. No signup. No cost. Just better questions. If you're in customer discovery mode right now, try it before your next interview. Then come back and tell me what you learned.

Juicero raised $120 million and shut down four years later. The product was impressive. A beautifully engineered juicer that squeezed proprietary juice packs. The pitch was compelling. Fresh, cold-pressed juice at home with zero mess. But none of that mattered because they misjudged the market. They built a $400 machine for a customer who didn't exist at scale. Worse, when reporters discovered you could squeeze the packs by hand and get the same result, the entire value proposition collapsed. This wasn't a failure of execution. It was a failure of go-to-market strategy. If you're a small business owner handling your own marketing, the same mistake shows up in smaller ways every day. You build something without validating whether your audience actually wants it. You position a feature instead of a benefit. You invest time creating content that sounds good internally but doesn't connect with the people you're trying to reach. The fix starts with three questions before you build or launch anything: Who is this for, specifically? Not a broad market. A real person with a real problem. What job are they hiring this to do? Juicero thought people wanted convenience. Turns out they wanted juice, and convenience meant not buying a $400 machine. How will they discover this solves their problem? If your positioning doesn't make the value obvious in seconds, you're asking too much of your audience. Juicero had the funding, the team, and the product. What they didn't have was a clear understanding of their customer or a go-to-market strategy grounded in reality. You don't need $120 million to learn this lesson. You just need to ask the right questions before you spend time and money on the wrong strategy. If you're not sure whether your positioning and content strategy are connecting with your audience, book a free 15-20 minute marketing audit. I'll walk you through where to focus first. https://www.radi8.com/free-audit?utm_source=linkedin&utm_campaign=free_audit&utm_content=post_id Case study: https://www.smartwareadvisors.com/blogs/insights/case-study-juicero-overbuilt-mvp-amp-misjudged-market

Customer Discovery