Takeaways:
Some questions to ask:
What is the hardest part about doing the thing that you’re trying to solve?
Start of an open ended conversation
Tell me about the last time that you encountered this problem?
Specifics of the context in which they are. Use this to think about product features and positioning
Why was this hard?
Helps to identify the real problem. This is the real - “why”. Potentially your marketing proposition to the customer.
What, if anything, have you done to try to solve this problem?
Indicates that this is a real problem that they are investing time solving it
[Tactical] What don’t you love about the solutions that you’ve already tried?
| Principle | Description | Example |
|---|---|---|
| Avoid Pitching | Refrain from directly pitching your idea to potential customers. Instead, focus on understanding their needs. | Instead of saying, “I have a great product idea. Would you buy it?”, ask, “Tell me about the biggest challenge you face in XYZ area.” |
| Talk About Their Lives | Engage customers in conversations about their experiences, challenges, and goals. | Ask questions like, “Can you walk me through a recent situation where you encountered this problem?” |
| Ask About Past Behavior | Inquire about their past experiences and decisions related to the problem you’re addressing. | Ask questions such as, “Can you describe a time when you tried solving this problem? What approach did you take?” |
| Listen for Specifics | Encourage customers to provide specific details and examples. | Prompt them to share specific instances, like “Could you give me an example of when this problem caused a significant issue?” |
| Focus on Actionable Insights | Strive to uncover insights that guide decision-making and product development. | Look for insights such as “I tried using XYZ solution, but it didn’t solve the problem effectively.” |
| Validate Scalable Problems | Ensure the problem you’re addressing is widespread and impacts a larger target audience. | Validate if multiple customers in the same industry or market segment face a similar challenge. |
| Iterate and Learn | Treat conversations as learning opportunities and iterate based on the feedback received. | Actively take note of customer feedback and make adjustments to your product or approach accordingly. |
Relevant Links
An amazing explainer on how this founder applies these principles practically

