In the early days of building a startup, founders tend to focus heavily on engineering and marketing their product. While these areas are undoubtedly important, there’s one essential aspect that unfortunately often gets pushed to the side — research through direct conversations with existing or potential users.
Talking to your users may look like a simple task on the surface, but there’s a lot of nuance to interviewing a user in a way that doesn’t corrupt the information you’re given and extracts as much as possible in the short timeframe you have with them.
This guide will take you through speaking to users, from preparing for these conversations to transforming insights into action. We’ll explore the best practices for asking the right questions, avoiding common pitfalls, and using user insights to drive product decisions that fuel growth.
Table of Contents
1. Fundamentals of the founder-user relationship
1.1 Why Founders Should Speak to Users
User interviews are the most useful and effective research method founders can use. They can reveal the most authentic pain points, the most actionable product improvements, and the untapped opportunities for product-market fit. Data and analytics can provide hard numbers, but human interaction can uncover emotional motivators, decision-making processes, and deeper issues that numbers can’t explain.
Think of it like going to the doctor - bloodwork can help identify what’s wrong but without talking to the patient, a doctor can’t always accurately pinpoint the issue. They need to understand how they feel, their lifestyle, and the context in which their problem appeared.
Similarly, using data can indicate where you might have a problem, but not why it’s a problem and how to fix it. Also, most startups don’t have enough volume to work with. Interviewing users is the holy grail of early user research and achieving product-market fit.
1.2 Founders’ Role in User Research
While your product and marketing teams may be tasked with gathering data, organizing interviews, and running them, founders should at least shadow them. Why? This ensures that founders keep their ears to the ground and adapt their business strategy to customers' needs, not their own beliefs about what the solution should be. Founders justifiably get emotionally attached to the products they’re building, sometimes making them tone-deaf. The only solution is to listen to users and face the facts.
Additionally, when founders speak directly to users, it can also build a stronger sense of trust and community. Users feel heard and understood, knowing that their feedback goes straight to the top. That’s a key competitive advantage startups have over bigger companies.
Jeff Bezos was notorious for making his Amazon email address public. He was known for responding to some complaints himself or sometimes forwarding them to a team with a single question: “Why?”. While you might argue it wasn’t the best project management technique, it was a sign he was deeply interested in customer experience. This was one of the key drivers of Amazon’s early success.
1.3 The value of direct user feedback for founders
By speaking to users firsthand, founders gain:
- Unfiltered insights : Insights passed on by a specialist bring up all kinds of trust and reliability issues. Did this person run the interview well? Is their interpretation of the feedback accurate? Is this truly a major issue? When founders get involved in user interviews, feedback isn’t diluted or filtered through layers of teams, and it has the most impact.
- Early detection of product-market fit issues : Founders can identify misalignments between user needs and product features, allowing for faster pivots or adjustments.
- Innovative ideas : Most times the first iteration of a product isn’t the best solution. Engaging in an open discussion can reveal improvement ideas or entirely new avenues to explore. Youtube started as a dating platform. Later they noticed users keep uploading videos unrelated to dating. This realization determined the company to pivot and grow into the giant that is today. If they had ignored this user behavior, they probably wouldn’t exist today, having faded over time as so many dating websites have.
2. Preparing for user interviews
Great user conversations don’t just happen—they require preparation. Founders need to approach these conversations with clear objectives, the right mindset, and a structured plan for extracting valuable insights.
2.1 Defining research types and objectives
Before diving into user interviews, it’s crucial to understand the distinction between generative and summative research, as this will shape the objectives of your conversations.
- Generative research is all about discovery. It helps you identify new opportunities, explore user needs, and understand the broader context of how users interact with your product or industry. If you’re in the early stages of product development or exploring a new feature, generative research can uncover user pain points and desires that you haven’t yet considered. For instance, questions might center around understanding users’ challenges in a specific domain or identifying unmet needs that could inspire new solutions.
- Summative research , on the other hand, is focused on evaluation. It helps you assess how well your existing product or features are performing based on user feedback. This type of research is typically done after launching a product or feature when you’re looking to measure its effectiveness or improve based on real-world usage. The goal is to confirm whether your solution is addressing the problem effectively, and feedback often centers on usability, satisfaction, and specific areas for improvement.
Knowing whether your objective is generative or summative shapes how you approach the conversation. If you’re trying to generate ideas, you’ll ask broad, open-ended questions to understand users’ daily workflows, pain points, and experiences with existing solutions. If you’re seeking summative insights, your questions will be more focused on specific product features, user interactions, and performance evaluations.
For example, if your goal is to explore how users currently solve a problem (generative), you might ask:
- “Can you walk me through how you currently handle [problem]?”
- “What challenges do you face when trying to solve [problem]?”
In contrast, if you want to assess how well a feature is working (summative), you might ask:
- “How was your experience using [feature]?”
- “Were you able to solve [problem] with the feature? What worked or what didn’t?”
By clearly defining your research objectives as either generative or summative, you can focus your user conversations more effectively and extract insights that directly inform your product decisions.
2.2 Segmenting users for interviews
Not all users are created equal. Segmenting them into specific groups like power users, casual users, churned users, and new users helps startups tackle growth challenges more effectively by focusing on each group’s unique experiences and pain points.
Here’s how you can leverage these segments to extract actionable insights and solve typical growth hurdles.
| Segment | Description | Example |
|---|---|---|
| Power Users | Power users are deeply engaged with your product, loyal, and committed. By interviewing them, you can uncover the specific features or workflows they value most. This can guide decisions around retention strategies, helping you replicate those features or experiences for other segments. | If power users consistently mention that a specific feature boosts their productivity, consider highlighting or improving this feature in your onboarding for new users to drive quicker adoption and increase engagement. |
| Casual Users | Casual users engage less frequently. They might be experiencing minor frustrations, lack a compelling reason to engage, or simply not see the value proposition. By learning from casual users, you can identify barriers to engagement and make changes that promote more frequent use. | If casual users report that they only use the product when specific needs arise, it may be an opportunity to introduce reminders, in-app notifications, or features that encourage more regular interaction. |
| Churned Users | Churned users are a goldmine for understanding the reasons behind disengagement and dropout. Speaking to churned users can reveal critical issues in usability, feature gaps, or unaddressed needs that drove them away. | If churned users cite a steep learning curve, revisit the onboarding process or offer educational resources. Improvements driven by churned users can boost retention for new and casual users. |
| New Users | New users provide direct feedback on how your product’s onboarding performs. Understanding their initial struggles and joys can guide you in optimizing onboarding to ensure they see value quickly, which is key to driving activation and reducing early churn. | If new users feel overwhelmed by too many options, simplifying the onboarding process to guide them through essential features first could increase initial engagement and make the product feel more approachable. |
By interviewing each of these user segments, founders can align product development with real user needs, prioritize improvements that have the greatest impact, and build a user journey that supports growth across the entire customer lifecycle.
3. How to ask the right questions
User conversations are only as good as the questions you ask. Thoughtfully framing your questions will determine whether you extract shallow feedback or uncover meaningful insights that can drive growth.
3.1 Open-Ended vs. Leading Questions
One of the biggest mistakes founders make when speaking to users is asking leading questions. Leading questions suggest a particular answer or bias the user’s response. For example:
- Leading question: “Would you find it helpful if we added X feature?”.
- Open-ended question: “How do you currently solve [problem]?”
Open-ended questions encourage users to speak freely and share their true thoughts. Here are some effective open-ended questions to consider:
- “Tell me about your experience with our product. What stood out to you?”
- “What problems are you trying to solve with our product?”
- “What does your workflow look like when fixing that problem?”
- “Can you walk me through how you use our product on a typical day?”
Finally, remember to focus your questions on what users do rather than what they say they’d like. People are not experts in solutions. They’re experts in their problems. Even if a question is open-ended, it’s not useful if it requires people to dream up solutions to their problems. This brings us to the next point.
3.2 Focusing on problems, not solutions
Users are often quick to suggest solutions. However, their solutions may not be the best way to address their underlying problem. Your job as a founder is to dig deeper into the problem itself. When a user proposes a feature or change, instead of taking it at face value, follow up with questions like:
- “Why do you need that?”
- “What problem would that solve for you?”
- “How are you solving this problem today without this feature?”
Understanding the root problem allows you to create a complete solution and make sure it integrates well with the rest of the system, rather than building a feature that may only be a surface-level fix (the infamous “hotfix”).
For further reading on this topic and more, I recommend “ The Mom Test” by Rob Fitzpatrick.
3.3 Example: extracting feedback from a churned user
Imagine you’re speaking to a user who churned after using your product for three months. Instead of asking, “Why did you stop using the product?” (which may yield a vague response), you ask:
- “Can you walk me through your experience with the product from the moment you signed up?”
- “What did you expect the product to help you achieve?”
- “At what point did you feel like the product was no longer meeting your needs?”
These questions encourage the user to reflect on their experience and give detailed feedback that can inform future improvements.
4. Active listening techniques
Great user interviews require more than just asking the right questions—you need to actively listen to what users are saying (and not saying). Active listening helps uncover deeper insights by keeping interviewees engaged and pushing them to provide deeper insights.
4.1 Listen more. Talk less. Sell nothing.
During user conversations, founders often feel the urge to explain their product or respond defensively to negative feedback. However, the goal is to listen, not to sell or to justify your past design decisions. Try to follow the 80/20 rule—let users do 80% of the talking, and only use 20% of the conversation for clarification or follow-up questions.
4.2 Reading between the lines
Users don’t always say exactly what they mean, and sometimes, the most valuable insights come from what’s left unsaid. Pay attention to non-verbal cues like hesitation, changes in tone, or long pauses. If a user is struggling to articulate something, ask them to clarify or expand on their point.
There’s not much else to say here other than “Keep your eyes open and use your best judgment”. It’s more art than science and more experience than method.
4.3 Dig deep - asking probing questions
Effective user conversations involve probing beyond surface-level answers. Sometimes users might be reluctant to open up. In such cases, a pause might be enough to cause them to want to fill the void and continue talking. Other times, a simple “Yes, go on…” together with a gesture that hints that they should continue is enough. When that doesn’t work, use follow-up questions like:
- “ You said that… (help them recall). Can you tell me more about that?”
- “What did you mean when you said…?”
- “Why did you…?”
These follow-up questions encourage users to reflect more deeply and share insights that they might not have initially mentioned.
4.4. Note-taking during interviews
Don’t take notes while talking to users because it dilutes your attention and disengages the interviewee. Instead, either have someone else take on the note-taker role or record the meeting and extract notes yourself after the call. There are recording call recording tools that use AI to analyze what was said and extract the key points. However, keep in mind these transcription tools are not a replacement for UX specialists. I recommend reviewing the AI-generated notes and listening to the call again to make sure the maximum value is extracted.
A great tool for running user interviews and taking notes is Lookback. The app lets you add timestamped notes to your interview recording, adding essential context to your note, and making it easy to share with your team.
5. Common Pitfalls to Avoid
While speaking to users can be incredibly valuable, there are also common pitfalls that can derail your efforts. Here are some mistakes to watch out for—and how to avoid them.
5.1 Confirmation bias
Confirmation bias occurs when founders subconsciously steer conversations to confirm what they already believe about their product. This can happen when you ask leading questions or ignore feedback that contradicts your assumptions.
To avoid confirmation bias:
- Actively seek out users who have had negative experiences with your product. This helps you maintain a balanced view of how well your product performs.
- Challenge your assumptions and be open to feedback that doesn’t align with your expectations.
- Encourage users to critique the product by asking, “What would you change or improve?”
Being aware of your own bias requires practice. Biases are by definition unconscious, making them hard to spot. It takes a high degree of self-awareness and honesty to bring them to light. Listening to recordings of your conversations or having someone else do it can help identify them.
Here’s a short video from Nelse Norman - a leading UX consultancy, about how confirmation bias can influence the work of UX professionals.
5.2 Over-generalizing feedback
It’s tempting to let one or two user conversations dictate product decisions, but over-generalizing from a small sample can lead to misguided priorities. A few vocal users don’t represent the entire user base, and building features based on isolated feedback may lead to wasted resources and effort.
To avoid over-generalizing:
- Look for patterns. Collect feedback from multiple users before making decisions. If you hear the same issues from different user segments, that’s a sign the problem is more widespread.
- Balance qualitative and quantitative data. Combine user interviews with data from surveys or product analytics to validate insights at scale. If multiple users are saying they want a particular feature, use a large-scale survey to validate the need for it.
5.3 Getting defensive
Founders are deeply connected to their product, so it’s natural to feel defensive when users provide negative feedback. It’s like telling someone their baby is ugly. However, reacting defensively can shut down valuable insights and make users less willing to share honest opinions.
To avoid defensiveness:
- Adopt a growth mindset. Treat feedback as an opportunity to improve your product rather than as criticism.
- Thank users for their honesty. Acknowledge that their feedback is helping you create a better product.
- Stay curious. Focus on understanding why users feel the way they do instead of defending your product’s current state
5.4 Losing control of the conversation
Sometimes users who are passionate about a subject might unintentionally take over the conversation and start brainstorming solutions. While you generally don’t want to stop a user from talking, remember the goal of any interview is to understand a problem or determine if a feature solves a problem, not to let the interviewee run wild with ideas. In such cases, the interviewer needs to be assertive, intervene, and steer the conversation in the right direction.
Be polite and gentle, but firm. Saying something like this could help: “That’s an interesting idea. I wrote it down in my notes, but I’d like to know more about something you mentioned earlier. You said that … What did you mean?”
5.5 Focusing on opinion, not action
User interviews generate the most value when the discussion focuses on what the user does rather than what they say. Opinions are more important in branding and things that have to do with perception rather than problem-solving. Instead of users talking about what they think about a solution (yours or a competitor’s), focus the conversation on what they do. Ask your interviewee to walk you through what they do, in detail. If possible, allow them to show you how they fix a problem. To maximize your understanding of what they’re doing, ask users to think aloud - i.e. narrate what goes on in their minds as they're doing the task.
6. Turning insights into action
Gathering user feedback is only valuable if it leads to actionable steps that improve your product. Once you’ve conducted user interviews, it’s time to organize, analyze, and apply the insights to your product development strategy.
6.1 Look for Patterns
After conducting a series of user conversations, review your notes and look for recurring themes. For each interview, extract insights and group them into categories (e.g., usability issues, feature requests, or onboarding challenges) to identify which areas of the product need the most attention.
For example:
- Do multiple users struggle with the same feature?
- Are you hearing the same frustration about the onboarding process?
- Are users asking for similar features or improvements?
6.2 Prioritize based on impact
Not every piece of feedback should result in a change. Instead, prioritize feedback based on its potential impact on user satisfaction, retention, or growth and the effort it takes to implement it. There are many prioritization frameworks out there, but for startups, a simple effort-impact scale is all that’s needed.
When deciding on impact scores, consider factors like:
- Frequency : How often do users mention this issue?
- Severity : How much does the issue impact the user experience?
- Alignment with your product vision : Does the feedback align with your long-term goals and strategy?
For example, if several users mention difficulty with a core feature, fixing it should take priority over adding new features that only a small group of users requested.
6.3 Workflow template in Notion
I created a Notion template that includes trackers for user interviews and what I call “UX bugs” - i.e. design and usability issues identified during interviews.
The template uses 3 databases: user interviews, UX bugs, and user personas.
Here’s a closer look at each one.
User interviews. This is where track everything about interviews - interviewer, interviewee,
date, matching user persona, duration, and status.
UX bugs are aggregating the issues recorded across all interviews. We can group issues by severity, product area, interviewed person, or status. Notion makes this very easy.
User personas.
This is optional. It’s a place to store all information about the user personas (problems, frustrations, needs, etc). This tracker is linked to User interviews and helps mark what type of user the interview was with.
The workflow
For each interview add the link to the recording, extract timestamped notes with key conclusions and learnings, and add items to the “UX issues” table. This will add items to the UX bugs table and link them to the interview, adding essential context to the ticket.
6.4 Testing and iterating based on feedback
Periodically review the “UX bugs” tracker and prioritize high-impact items by adding them to your roadmap. High-effort items can be turned into a project and low-effort ones can be batched together to form an improvement project.
Don’t rush to ship solutions in production. Turn insights into hypotheses that you can test. Iterate on solutions and test them early before fully implementing changes. For example:
- If users struggle with onboarding, test different onboarding flows to see which one improves activation rates. This can easily be prototyped in Figma and tested with a tool like maze.co.
- If users request a new feature, create a prototype and gather additional feedback before fully developing it.
By testing your assumptions early and often, you can avoid spending time and resources on changes that don’t resonate with users.
Conclusion: prioritizing user conversations drives growth
Speaking to users is one of the most effective ways for founders to extract the insights needed to drive product growth. By asking the right questions, actively listening, and avoiding common pitfalls, founders can gain a deep understanding of user needs and pain points.
Once these insights are collected turn them into actionable steps that prioritize high-impact improvements. Whether addressing usability issues, fixing onboarding problems, or exploring new features, user feedback should be at the core of your product development strategy.
Follow these steps to ensure you’re extracting essential insights from your users, driving meaningful growth, and ultimately creating a product that users love… paying for.
About the author
Călin Balea runs Contrast - a design studio for new ventures. A designer with over 10 yrs of experience in the startup space, Călin has helped several companies design apps and websites that helped raise over $20mil.
