Top 7 'Assumption-Shattering' Customer Discovery Questions to try for entrepreneurs before writing a single line of code - Goh Ling Yong
You’ve got it. The lightning-in-a-bottle idea. The one that keeps you up at night, sketching on napkins and whiteboards. It’s a game-changer, a paradigm-shifter, the SaaS platform that will redefine an entire industry. Your fingers are itching to open your code editor, to start architecting the database, to build the beautiful UI you see so clearly in your mind.
Stop. Take a deep breath. And for the love of your future business, step away from the keyboard.
The startup graveyard is littered with beautifully engineered products that nobody wanted. The fatal mistake wasn't a bug in the code or a slow server; it was a bug in the initial assumption. The founders fell in love with their solution before they truly understood the problem. They built a key, then went looking for a lock. This is the single most common reason why startups fail. The antidote? A process that feels deceptively simple but is incredibly powerful: customer discovery.
But customer discovery isn’t about pitching your idea and asking, "So... would you use it?" That question is a trap. People are nice. They’ll nod and smile, giving you the false-positive validation that sends you down a six-month rabbit hole of building the wrong thing. True, effective customer discovery is about becoming a detective. It’s about uncovering the truth of your customer’s world, their pains, their workflows, and their motivations. Your goal isn't to get a "yes," it's to get to the truth.
To do that, you need the right tools. Here are the top 7 'assumption-shattering' customer discovery questions you must ask before writing a single line of code.
1. “Can you walk me through the last time you dealt with [problem context]?”
This is the golden question. It’s the master key that unlocks a treasure trove of insights. Notice it doesn’t ask for an opinion or a hypothetical scenario. It asks for a story about a specific, past event. People are terrible at predicting their future behavior but are fantastic storytellers about their past experiences.
When you ask this, you’re not a salesperson; you’re a journalist. Your job is to listen intently as they recount their experience. What tools did they use? Who did they collaborate with? Where did they get stuck? What emotions did they feel—frustration, confusion, anxiety? These details are pure gold. They reveal the context, the hidden complexities, and the real-world friction points that a simple "Do you have this problem?" could never uncover.
Tips for success:
- Be specific: Instead of a vague "your workflow," ask about a concrete task. For a project management tool, it might be, "Can you walk me through the last time you had to update your team on a project's status?"
- Listen for hacks and workarounds: Pay close attention to when they say things like, "And then I have to copy-paste this into a spreadsheet, email it to my boss, and then ping everyone on Slack..." Those are symptoms of a problem they care enough about to solve, even with inefficient tools.
- Follow up: Use prompts like "Tell me more about that," or "What happened next?" to dig deeper into the most interesting parts of their story.
2. “What’s the hardest or most frustrating part about that process?”
Once they've laid out the entire workflow, it's time to zero in on the pain. This question is a direct probe for the emotional core of the problem. A mild inconvenience is a "nice-to-have" solution. A soul-crushing, time-wasting frustration is a "must-have" solution. You're looking for the latter.
This question helps you validate that the problem you think they have is the problem they actually have. You might believe the hardest part of their workflow is generating reports, but they might tell you the real nightmare is getting the right data before the report is even made. This is a critical distinction that could completely change the direction of your product.
Tips for success:
- Listen for emotional language: Words like "hate," "annoying," "frustrating," "nightmare," or "time-suck" are strong signals that you’ve hit a nerve.
- Don't lead the witness: Avoid asking, "Wasn't it hard when you had to do X?" Let them identify the pain on their own terms. Their unprompted answer is 100x more valuable.
- Quantify the pain: If they say a task is "time-consuming," follow up with, "Roughly how much time does that take you each week?" This helps you build a business case later.
3. “How are you currently solving this? What have you tried in the past that didn’t work?”
This is my favorite assumption-killer. If a problem is painful enough, people are almost always doing something to solve it, even if it's a clumsy, inefficient mess. This is your competition, and it's not just other software products. Your competition could be a complex Excel spreadsheet, a series of email templates, a shared Google Doc, or even a dedicated intern.
Discovering their current solution does two things. First, it validates the problem's existence and severity. If they haven't bothered to create any kind of workaround, the problem might not be as urgent as you thought. Second, it gives you a benchmark. Your solution doesn’t just need to be better; it needs to be so much better that it overcomes the switching costs of them abandoning their current, familiar process. Learning what they’ve tried and abandoned also tells you what not to build.
Tips for success:
- The "Excel and Duct Tape" Test: If you find a user with an elaborate, multi-tabbed spreadsheet full of complex formulas they've cobbled together, you've likely found a real, hair-on-fire problem.
- Ask why past solutions failed: If they tried a competitor's product and quit, ask why. Was it too expensive? Too complicated? Missing a key feature? This is free, invaluable competitive research.
- Don't dismiss manual solutions: A person manually doing a task is a huge opportunity. It’s often easier to sell a solution that automates a human process than it is to replace an existing piece of software.
4. “What are the consequences of not solving this problem? What happens if you just do nothing?”
This question gets to the "so what?" of the issue. It separates a vitamin (a nice-to-have that improves things) from a painkiller (a must-have that stops a searing pain). A strong, urgent problem has significant negative consequences if left unsolved. These consequences are usually measured in time, money, or risk.
Does the problem cause them to lose sales? Does it cost them hours of wasted productivity each week? Does it open them up to compliance risks or costly errors? If the answer is, "Well, nothing really, it's just a bit annoying," you may be building a vitamin. Vitamins are much, much harder to sell than painkillers. People will crawl over broken glass for a painkiller.
Tips for success:
- Dig for metrics: If they say it "wastes time," ask how much. If it "costs money," ask for a rough estimate. This helps you understand the ROI of your potential solution.
- Listen for second-order consequences: The first consequence of a poor reporting system is a bad report. The second-order consequence is a bad business decision made based on that report, which could cost the company thousands. That's the real pain.
- This helps define your value proposition: The answer to this question is the core of your marketing message. You're not selling features; you're selling the elimination of these negative consequences.
5. “If you had a magic wand and could fix this instantly, what would the perfect solution look like for you?”
This is a much better way to ask, "What features do you want?" Asking for features turns your customer into a product designer, which is not their job. It often leads to a laundry list of requests for buttons and dashboards. The "magic wand" question, however, encourages them to describe their ideal outcome, not a specific implementation.
They might say, "I'd just wave the wand and my boss would have the report on her desk, exactly how she likes it, every Monday at 9 AM without me ever having to think about it." Boom. That’s not a feature list; it’s a job-to-be-done. It tells you they value automation, reliability, and peace of mind. As a product person, it’s your job to translate that desired outcome into a set of features. Here at Goh Ling Yong's blog, we believe deeply in focusing on the customer's "job" rather than just the features they ask for.
Tips for success:
- Focus on the "what" and "why," not the "how": If they start describing a specific interface, gently guide them back by asking, "And what would that allow you to do?" or "Why would that be better for you?"
- Don't take it literally: The magic wand answer is a vision, not a spec sheet. Use it as inspiration to understand their ultimate goal.
- Look for the underlying need: They might describe a "big red button," but the underlying need is for simplicity and confidence that a complex task is done correctly.
6. “What’s your budget for solving a problem like this? Have you ever paid for a solution before?”
It can feel awkward to talk about money this early, but it's crucial. A person complaining about a problem is interesting. A person paying money to solve a problem is a potential customer. This question is a gentle way to probe their willingness to pay.
Framing it around their "budget" is less aggressive than asking "What would you pay for my product?" which they can't answer yet. Asking if they've ever paid for a solution is even better, as it grounds the conversation in past behavior. If they’ve paid for tools to solve adjacent problems, it shows they have the willingness and ability to spend on software. If they've never paid for a business tool in their life and only use free options, you might be talking to the wrong customer segment.
Tips for success:
- Look for a budget proxy: If they can't give you a number, ask what they pay for other tools. "What do you pay for your CRM, or your email marketing software?" This gives you a ballpark of what they consider reasonable.
- "Free" is a red flag: If their current solution is free and their answer to the budget question is "I'd expect this to be free," you may have a monetization problem, not a product problem.
- Position against cost: If you've already quantified their pain (from question #4), you can use that. "If this problem is costing you $500 a month in wasted time, would paying $50 a month for a solution be a no-brainer?"
7. “Based on our conversation, who else do you think I should talk to?”
This is the perfect closing question, and it serves two brilliant purposes. First, it’s a subtle validation check. If you’ve correctly identified a real and common problem, the person you’re speaking with should be able to immediately think of colleagues, friends, or peers who share their pain. If they draw a blank and say, "Hmm, I'm not sure, I think it might just be me," that's a major red flag. Your niche might be too small, or the problem might be unique to their specific context.
Second, if the conversation went well and they do know others, this question is your single best source of new leads for more discovery interviews. A warm introduction ("I was just talking to Sarah, and she suggested I reach out to you...") is infinitely more effective than a cold email. It builds momentum and helps you quickly map out the customer landscape. As Goh Ling Yong would advise, building this initial network is a critical step in finding product-market fit.
Tips for success:
- Be direct: Don't be shy. If the conversation has provided value to them (by letting them vent about their problems), they will often be happy to help you.
- Make it easy: Offer to write the intro email for them. "Would you be open to introducing me to John via email? I can draft a short note to make it super easy for you."
- End on a high note: Always thank them for their time and insights. Let them know you’ll keep them updated on your progress—they are now your earliest potential evangelists.
From Assumptions to Conviction
There you have it. These seven questions aren’t a script, but a framework for a curious conversation. They shift the focus from "Look at my cool solution!" to "Tell me about your painful problem."
The answers you get might be scary. They might invalidate your beautiful, perfect idea. And that’s a good thing. It's infinitely better to pivot after seven conversations than after a year of coding and a drained bank account. Each shattered assumption is a gift—a course correction that guides you away from a product nobody wants and toward one that people can't live without.
So, before you write that first line of code, get out of the building (or on a Zoom call) and start asking better questions. The future of your startup depends on it.
What are your go-to customer discovery questions? Share your favorites in the comments below!
About the Author
Goh Ling Yong is a content creator and digital strategist sharing insights across various topics. Connect and follow for more content:
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