Early in my founder journey with my food photography app, I faced a frustrating reality: I was having plenty of user conversations, but I wasn't getting the insights I needed. My interviews felt shallow, with users giving me polite but unhelpful feedback that didn't guide my product decisions.
Sound familiar?
I realized I was asking the wrong questions. I was leading with "Would you use this?" or "Do you like this feature?" — questions that invited hypothetical answers and social pleasantries rather than genuine insights.
But there were two other critical mistakes I was making:
First, I was talking to the wrong people. In those early days, I relied heavily on friends and family for feedback. They were supportive and eager to help, but they weren't my target users. When I finally started connecting with actual restaurant owners, food delivery companies and food photographers—people who felt the pain points daily—the quality of insights changed dramatically.
Second, I was basing decisions on too few conversations. After interviewing two restaurant owners who liked a feature, I'd mistakenly consider it validated. I learned the hard way that you need to talk to at least 15-20 people per user persona before patterns become reliable. When I expanded my research to include 25+ restaurant owners, completely different priorities emerged from what my initial small sample suggested.
Everything changed when I developed a framework of five specific questions that cut through the noise and revealed what users actually needed — not what they thought they wanted or what they thought I wanted to hear.
Today, I'm sharing this exact framework that revolutionized my approach to user research and ultimately led to finding product-market fit for my business.
The 5-Question Framework That Gets Real Answers
After dozens of interviews and considerable trial and error, I've refined my approach to these five core questions that consistently deliver powerful insights:
1. "What was the hardest thing you did when trying to solve [specific problem]?"
This question does something magical: it shifts the conversation from hypotheticals to specific experiences. By focusing on hardship, you bypass surface-level opinions and get to emotional pain points.
When I asked restaurant owners this about food photography, I discovered that their biggest challenge wasn't taking photos (as I had assumed) but coordinating with photographers around their busy service hours. This insight completely changed our scheduling feature priorities.
2. "Tell me about the last time you encountered this problem."
The power of this question lies in its specificity. Instead of general patterns, you get detailed, contextual information about a recent experience when the pain was fresh.
When I used this with food bloggers, I learned that their most recent frustrations weren't about photo quality but about consistency across multiple shooting sessions. This led us to develop lighting presets that became one of our most valued features.
3. "What was hard about this?"
This follow-up question digs deeper into the specific friction points. I've found it's crucial to ask this even when you think you understand the challenge, as the actual difficulty often lies in unexpected places.
For instance, when food photographers described their workflow, they mentioned editing as time-consuming. But when I asked, "What was hard about this?" they revealed the real challenge: communicating revisions with clients. This insight led to a collaborative feedback tool that dramatically improved our product offering.
4. "What did you do to solve this problem? How much do you pay for this now?"
This question reveals existing solutions and workarounds, giving you insight into:
- How urgent the problem is (based on how much effort they've already invested)
- What solutions you're competing with
- Features users already expect
I discovered that restaurant owners were using a patchwork of text messages, email reminders, and calendar invites to coordinate with photographers. This gave us a clear blueprint for our scheduling and communication features.
5. "What do you dislike about the solutions you've already tried?"
Here's where you find your competitive advantage. This question uncovers the gaps in existing solutions and shows exactly where your product can provide superior value.
When I asked this question, I learned that existing photography apps were designed for professional photographers, with complex interfaces that frustrated casual users like restaurant staff. This insight shaped our entire UX philosophy, focusing on simplicity and guided workflows.
Implementing the Framework Effectively
The magic of these questions isn't just in asking them—it's in how you ask them. Here are my tips for getting the most valuable answers:
Ask for Specifics, Not Generalizations
When someone says, "It's usually pretty difficult," follow up with "Can you tell me about a specific time when it was difficult?" Concrete examples yield actionable insights.
Embrace the Silence
After asking one of these questions, wait. The initial answer is rarely the most insightful one. Often, after 5-10 seconds of silence, users will provide deeper, more thoughtful responses.
Listen for Emotional Signals
Pay attention to changes in tone, frustrated sighs, or excited explanations. These emotional indicators often reveal the true pain points and desires better than the words themselves.
Go Beyond the First Answer
Always follow up with "Why?" or "Tell me more about that." The most valuable insights are usually layered beneath the initial response.
Common Pitfalls to Avoid
Through my years of conducting user interviews, I've fallen into several traps that I now help founders avoid:
Pitfall #1: Selling Instead of Listening
When users mention a problem, it's tempting to immediately explain how your product solves it. Resist this urge! Continue asking questions instead of pivoting to pitch mode.
Pitfall #2: Leading Questions
Questions like "Wouldn't it be better if..." or "Don't you think that..." introduce bias. Stick to open-ended questions that don't suggest a "right" answer.
Pitfall #3: Reacting to Feedback
Whether you're thrilled or disappointed by what you hear, maintain a neutral expression. Your reactions can influence how honest users are willing to be.
Turning Insights into Action
The true value of this framework comes from how you use the insights you gather. After each interview, I recommend:
- Identifying patterns across multiple conversations
- Mapping pain points to potential features
- Prioritizing issues based on frequency and emotional intensity
- Testing assumptions with follow-up conversations
When I implemented this process with my food photography app, we completely pivoted our feature roadmap based on the insights. We deprioritized advanced editing tools (which we initially thought were critical) and focused instead on streamlining the client feedback loop—a decision that dramatically increased user engagement.
How I Can Help You Implement This Framework
While this framework is powerful on its own, implementing it effectively requires practice and expertise. Many founders struggle with:
- Identifying the right users to interview
- Formulating follow-up questions in the moment
- Recognizing patterns across different conversations
- Translating insights into product decisions
This is where my expertise can provide significant value. As someone who has conducted hundreds of these interviews across multiple industries, I offer specialized support in two ways:
Option 1: Interview Training and Coaching
I can work directly with you and your team to master this interview framework. Through personalized coaching sessions, I'll help you:
- Adapt these questions to your specific industry
- Practice effective follow-up techniques
- Develop skills for identifying underlying needs
- Create systems for turning insights into actionable roadmaps
Option 2: Dedicated Research Partnership
For founders who want to focus on building rather than researching, I also offer comprehensive user research services where I:
- Identify and recruit relevant participants
- Conduct interviews using this proven framework
- Analyze patterns and extract key insights
- Deliver actionable recommendations for your product strategy
While this service requires additional investment beyond my standard mentorship offering, clients typically find that the clarity and confidence it provides in their product decisions delivers exponential returns. The cost of building the wrong product is always higher than investing in understanding what to build in the first place.
The Next Step in Your Journey
Whether you implement this framework yourself or bring in expert support, asking the right questions will transform your understanding of your users and market.
I've seen founders completely revitalize struggling products after just a few properly conducted interviews. The insights are already there, waiting to be uncovered—you just need the right questions to reveal them.
If you're ready to cut through the noise and discover what your users truly need, I'd love to help you implement this framework. Reach out to discuss how we can work together to bring clarity to your user research and confidence to your product decisions.
Remember, the most successful products aren't built on assumptions—they're built on insights. And the right questions are the key to unlocking those insights.