E08: Creating customer interview questions before you have customers

The episode begins with host Jason Cohen introducing Rison Simon, a builder who previously sold a startup the week it launched but now faces a different challenge: his new product, PainPointy, has very few customers. Rison's goal is to interview potential customers to understand what they actually want, which will help him pivot his product more effectively. Jason Cohen, an experienced founder who has written extensively about customer development and validation, emphasizes the importance of structured customer interviews and introduces his 'Iterative Hypothesis' framework. Rison Simon explains that PainPointy scans Reddit to find authentic user pain points, which could be useful for marketers, product managers, and competitors, but he struggles with identifying who the actual target user should be and whether people would pay regularly for the service. Their conversation sets the stage for a deep dive into systematic customer discovery, focusing on how to formulate effective interview questions and hypotheses.

Rison elaborates on PainPointy's initial purpose—monitoring Reddit for user pain points and brand sentiment to generate article ideas, SEO insights, and competitive intelligence. Despite its potential, he admits that he can’t confidently define a precise target customer, partly because potential users include agencies, SaaS companies, and V2B businesses, but none seem to have a recurring use case or budget. Jason Cohen probes why, despite the obvious usefulness of analyzing authentic Reddit speech, competitors are already in this space, and Rison explains that his motivation was driven by the genuine voice behind Reddit comments. They discuss why, even though the tool captures authentic language, the core issue may be that users don’t see continuous value from reports or data—they just want to understand how to make better marketing and content decisions. The conversation shifts toward discovering the specific needs and validation of customer segments.

Jason Cohen introduces his 'Iterative Hypothesis' method, emphasizing the importance of writing down what you believe before you conduct interviews. This helps validate or invalidate assumptions through real customer feedback. Rison and Jason work through a detailed example, initially hypothesizing that a B2B SaaS head of SEO cares about content that converts trials, demos, and pipeline. They break down vague statements into specific, measurable hypotheses—e.g., that marketing content ideas can increase conversions. Jason stresses the importance of making hypotheses specific and evocative to generate meaningful questions. They analyze how to ask about customer roles and metrics without leading, illustrating that many hypotheses need to be split into smaller, more manageable parts. The episode highlights the process of refining assumptions into concrete, testable questions to guide effective customer discovery.

The hosts focus on how to craft questions that genuinely uncover customer needs without leading them to certain answers. Jason advocates for framing questions around customer pains and motivations—like asking what results would make a boss say, 'You're the best.' They discuss splitting broad hypotheses into specific ones, such as whether sales pipelines are full or whether leads are converting well, and then drafting questions that help validate these ideas. The conversation emphasizes the importance of framing objective results—such as doubling conversion rates—to shape hypotheses that are measurable and actionable. They explore how to identify the true pain points, such as the lack of empirical signals for marketing ideas, rather than superficial complaints, helping Rison understand how to focus his interview questions.

Jason offers practical advice on sourcing potential interviewees, emphasizing the importance of using one's own product, Reddit, LinkedIn, and other channels to find people willing to share insights. They talk about the difficulty for early-stage products to identify a specific target audience and suggest starting with broader segments while iterating toward narrower, more focused customer profiles. The discussion also covers how to structure interviews, including asking about the input into marketing iterations, how customers evaluate ideas, and what metrics they use. Jason advises ordering questions to build a natural flow and to prioritize high-impact questions early. They highlight the significance of observing how interviewees respond to different questions to refine hypotheses and question strategies iteratively, culminating in the idea of continuous testing and learning.

Towards the end, Jason encourages Rison to begin outreach and interviews even with the challenges of segmenting precisely. He underscores that initial hypotheses and questions are rough and will improve through practice. Jason recommends recording interview insights and revisiting them to refine the hypotheses further. He emphasizes that interviews themselves, even if imperfect, provide critical learning and validation, which will be easier with facilitation tools like AI. The episode concludes with a mutual enthusiasm for starting customer interviews, iterating on hypotheses, and ultimately building a product rooted in genuine customer needs. Jason indicates that they might revisit the process in the future as Rison gathers feedback and learns more.