Problem Interview Examples Worth Stealing (First-Time Founders)

Reading about problem interviews is one thing. Seeing them in action is another. Below are sketched-out examples of how a first-time founder might run a problem interview well, and what their notes might look like afterward. Names and details are illustrative. Use them as a model for your own.

Example 1: A Founder Researching Tools for Indie Course Creators

Founder asks: "Walk me through the last time you launched a course. What were you trying to do, and where did things get messy?"

Interviewee says: "Oh man. So I had the videos done, I had the landing page on Carrd, and I was using ConvertKit for the email list. The thing that almost broke me was getting all of that to talk to Stripe and the LMS at the same time. I spent a whole Saturday wiring up Zapier flows that kept breaking."

Founder follows up: "Tell me more about that Saturday. What specifically kept breaking?"

Interviewee: "Honestly the worst part was that someone would buy the course and the welcome email would not fire because Zapier had silently rate-limited. I only found out because two students DM'd me asking where their access was."

Note for the founder's doc: Trigger - launch day. Workaround - duct-taped Zapier flow. Pain - silent failures discovered via student complaints. Cost - one full Saturday plus reputational damage. Vocabulary: "wiring up," "silently rate-limited."

Example 2: A Founder Researching Workflow Tools for Small Agencies

Founder asks: "What is annoying about how your team handles client status updates right now?"

Interviewee says: "It is fine, mostly. We use a Notion template."

This is a vague answer. Many first-time founders would write down "fine, uses Notion" and move on. Watch the follow-up.

Founder follows up: "Tell me about the last time it was not fine."

Interviewee: "Oh. Last week. We had three project managers all updating the same Notion page and one of them overwrote the others without realizing. The client saw a half-finished update and got upset. We had to call them."

Founder follows up: "Has that happened before?"

Interviewee: "Maybe twice a quarter. We just live with it."

Note for the founder's doc: The first answer was "fine." The real answer was a recurring failure they have normalized. The follow-up "tell me about the last time it was not fine" cracked it open. This is the pattern: people minimize their own problems until you ask for a specific event.

Example 3: A Founder Researching Tools for Solo SaaS Builders

Founder asks: "Have you ever paid for or built anything yourself to help with this?"

Interviewee says: "Yeah, I bought a $99 plugin from Gumroad about six months ago. Used it twice. Cancelled. Then I built my own little script for the same thing in an afternoon and I have used that every week since."

Founder follows up: "Why did you cancel the plugin?"

Interviewee: "It was over-built. Way too many settings. I just wanted one button."

Founder follows up: "What does your script do that the plugin did not?"

Interviewee: "Honestly, less. It just does the one thing."

Note for the founder's doc: Real spend, real abandonment, real DIY replacement. The signal here is enormous. The customer told you the existing solution is wrong specifically because it is too complex, and that they would rather build their own minimum-viable version. That is product positioning information you cannot get from a survey.

What These Examples Share

Three things, every time. The founder asks an open-ended story prompt, not a yes-or-no question. The founder follows up at least twice on the most interesting thread, instead of moving on to the next question. The founder takes notes that include exact phrases and specific events, not paraphrases.

Notice also what is not in any of them. The founder never described their own product. The conversation is entirely about the interviewee's experience. That is the discipline.

Stealing the Pattern

You do not need to script every line. You need the same shape every time. A clean opening that announces no-pitch. An open-ended story prompt as the first question. Two or three follow-ups for every answer. Notes that include the words they used and the events they described.

Run five of these and you will see the texture starting to repeat. The same kind of triggers, the same kind of workarounds, the same kind of disappointments with existing tools. That texture is your map.

What Bad Examples Look Like

Just for contrast. A bad example: founder describes the product idea in the first three minutes. Asks "would you use this?" Person says yes. Founder writes down "positive signal." Walks away validated. Builds for six months. Discovers no one wants it.

The difference is not intelligence or effort. It is conversational discipline. The good examples sound almost ordinary. That is part of what makes them work.