How To Talk To Users | Startup School

Building a successful startup isn't about brilliant ideas that strike on lazy Sundays or late-night coding sessions. The reality looks nothing like Hollywood's version of entrepreneurship. Real startup success comes from something far more practical: having genuine conversations with your users and customers throughout your company's lifetime.

Key Takeaways

• Great founders talk to future customers before they even have a product, not after
• Focus on understanding problems deeply rather than pitching solutions during user interviews
• Find users through LinkedIn, online communities, and professional networks beyond your immediate circle
• Ask open-ended questions about current workflows and pain points, avoid yes/no questions
• Turn interview insights into testable MVPs by organizing feedback into problem categories

Why User Conversations Drive Startup Success

Users and customers represent the only stakeholders who actually pay you money. If anyone will tell you the truth about your product, it will be them. This honest feedback keeps founders grounded in reality rather than assumptions.

Consider Brian Chesky's approach at Airbnb. In 2010, he conducted an experiment that seemed almost radical: he gave up his apartment to live in 50 different Airbnbs over several months. This wasn't a publicity stunt. By doing this, Brian guaranteed himself the chance to talk with every single host during his stay, creating an incredible source of unfiltered feedback.

Even today, Brian and his co-founders receive calls from hosts on their personal cell phone numbers. These are the same numbers they originally put on the website when starting out. They weren't hiding behind anonymous "info@" or "do not reply" email addresses. This direct connection seemed radical to most founders, who typically spend their time trying to find scalable growth channels like Google ads instead of building personal relationships with users.

Finding the Right People to Interview

Start with Your Network, But Don't Stop There

The easiest interviews come from people you already know or those in your professional network. They're most likely to respond to your outreach. However, these familiar contacts might be less honest in their feedback to avoid offending you. Don't let this stop you from reaching out, but understand the limitation.

Co-workers and former colleagues often provide excellent insights. They understand your capabilities and might know your target market well. If you're building software for startups, navigating to potential users through your professional network becomes straightforward.

Expanding Beyond Your Circle

Your most valuable early users often exist outside your personal and professional circles. YC founders commonly find their first users through: - LinkedIn outreach - Reddit communities - Slack or Discord groups - Industry-specific forums - In-person networking events

Crafting Effective User Interviews

Setting Up for Success

Conduct interviews over video calls, phone calls, or in person. You learn significantly more from a five-minute video conversation than from 500 survey responses. Build rapport with your interviewee since they'll be answering questions no one has asked them before. They need to trust you and feel comfortable sharing honest feedback.

The most critical rule: don't introduce your idea until the very end of the call, or perhaps not at all. Presenting your solution too early biases their responses. Your role is to listen, not to pitch. Take detailed notes even if you're recording, as you'll need to convert audio to written insights anyway.

Questions That Reveal Deep Insights

Structure your interviews around these proven question types:

• "Tell me how you do X today" - Understanding current workflows reveals pain points
• "What is the hardest thing about doing X?" - Identifies the core problems worth solving
• "Why is it hard?" - Uncovers root causes rather than surface symptoms
• "How often do you have to do X?" - Determines problem frequency and urgency
• "Why is it important for your company to do X?" - Reveals underlying motivations and business value
• "What do you do to solve this problem today?" - Shows current solutions and workarounds

Master these powerful follow-up techniques:

• "What do you mean by that?"
• "Can you tell me more about that?"
• "Why is that important to you?"
• "Tell me about that"

Questions to Avoid

Certain question types derail productive interviews:

• "Will you use our product?" - They'll probably say yes, but it's meaningless
• "Which features would make product X better?" - That's your job, not theirs
• Yes/no questions - You need detailed explanations and concrete examples
• "How would a better product look to you?" - Most people aren't product developers
• Multiple questions at once - This confuses both the interviewee and your data

Understanding Problems vs. Solutions

One major interview pitfall involves focusing on features instead of problems. Your brain naturally jumps to solutions, but interviews exist to understand problems deeply. Users typically identify real problems accurately but propose poor solutions.

Gmail's early users asked Paul Buchheit to display both the inbox and individual emails simultaneously on screen. The real problem wasn't interface design - Gmail was simply too slow, and users didn't want to wait for emails to load. Similarly, early Airbnb guests requested host phone numbers not for convenience, but because they didn't trust the platform enough to book without personal contact.

Users also lack incentive to say no to additional features. They'll agree to almost anything you suggest. You're responsible for prioritization because you understand the business constraints and technical tradeoffs they don't.

Turning Insights into Action

Organizing Your Research

After conducting 5-10 user interviews, organize your notes systematically. Use sticky notes or digital tools to group insights into problem categories. Identify which problems appear most frequently and seem most critical to users. Write clear conclusions about what you've learned.

Use this information to create hypotheses about potential solutions. Don't over-intellectualize this process - start building an MVP as quickly as possible, but ensure your decisions rest on accurate user feedback.

Validating Problem Value

Before building anything, confirm the problem you're solving has genuine value. People must value the solution enough to pay for it. Here are three ways to evaluate problem value:

1. Existing payment patterns - Are people already paying for solutions in this space?
2. Current workarounds - Do people have solutions they're satisfied with, even basic ones like Excel or Google Sheets?
3. Sales difficulty - How easy will it be to sell to this audience? Selling to plumbers proves notoriously difficult compared to selling to startups, who regularly adopt new tools.

Testing Your MVP

Once you have a prototype - even just a clickable design in a tool like InVision - start showing it to users. Don't tell them what to do; simply watch them interact with it. Give them a specific goal like "try to make a booking" but don't guide them through each screen. If this were a real product, you wouldn't be standing beside every user providing instructions.

Have users think aloud while using your prototype. Their verbal reactions reveal which words they understand, which screens confuse them, and how they interpret different interface elements. This provides crucial insights for improving your design and messaging.

Building Long-term User Relationships

Keep your interview participants involved throughout your development process. Create a Slack workspace or WhatsApp group for your early users. Make them feel special - like they have exclusive access to a world-changing product in development.

Continue showing them your product as it evolves. This exclusive preview access builds trust and shows you respond quickly to their feedback. Many users also appreciate connecting with others who share similar challenges, and you're facilitating these valuable professional relationships.

Users and customers will keep you honest. They are the only stakeholders actually paying you anything.

Following this systematic approach to user research ensures you collect the right information from future customers, maintain their engagement throughout development, and transform their insights into a viable first product. The most successful founders never stop having these conversations - they remain connected to their users throughout their company's lifetime, using this direct feedback loop to guide every major product and business decision.