Problem Interviews Checklist for Technical Founders

The working checklist for technical founders. Skip the reading, run the steps. Designed for engineering-led founders with limited time and a need to actually finish the round.

One-Time Setup

• Define the user with two filters: a job-or-role and a recent behavior.
• Write three questions on a sticky note: story prompt, workaround, money or time spent so far.
• Open one shared doc for all interview notes. Date and name at the top of each entry.
• Decide the no-pitch rule: you will not describe what you are building during the call.
• Decide the no-solutioning rule: when you have a design idea during the call, write it in private notes, not into the conversation.

Sourcing the Calls

• Build a list of 40 candidates who fit the audience filter.
• Send each a three-sentence message: why specifically them, what you are researching, ask for 30 minutes.
• No deck, no Loom, no pitch. Promise no-pitch and keep it.
• Aim to land 15 calls.
• Send messages in batches of 10 over a few days.

Five Minutes Before the Call

• Open the notes doc to a fresh entry. Date, name, role, audience filter match.
• Re-read the three questions.
• Ask permission to record at the start if you intend to.
• Remind yourself: no pitching, no solutioning today.

During the Call

• Open with a low-stakes intro. State you are researching, not selling.
• Ask question one. Then shut up.
• After every answer, count to three before responding.
• Use the redirect: "Tell me more about that" or "Walk me through what happened next."
• Capture exact phrases when they say something specific or vivid.
• If they ask what you are building, deflect to the end of the call.
• When a design idea hits you, write it silently. Do not voice it.
• End on time. Thank them. Ask if they would be open to a follow-up.

Within Ten Minutes After the Call

• Add three things to the bottom of your notes: trigger event, what they actually did, one thing that surprised you.
• Mark direct quotes with an asterisk so you can find them later.
• Note any tool, internal hack, or workaround you should look up afterward.
• Move any private design ideas into a separate "hypotheses" doc, not the interview notes.

After Every Five Calls

• Reread the last five sets of notes back-to-back.
• Write down repeats: same workaround, same vocabulary, same trigger, same internal tool.
• Write down disconfirmations: things you assumed that have not held up.
• If a question keeps surprising you with weak answers, replace it.

After Fifteen Calls

• In one sentence each: who is the user, what is the problem, what is the workaround.
• If you can answer cleanly, stop interviewing. Build the smallest possible version.
• If you cannot, decide what is missing: tighter audience, different questions, or a coherence problem with the original idea.
• Pick the next move within a week. Do not let the round drift.

Anti-Patterns to Watch For

• You described your product. Reset on the next call.
• You solutioned out loud. Reset on the next call.
• You only talked to people you already knew. Get to strangers.
• You wrote paraphrases instead of quotes. Quotes carry the data.
• You did three calls and called it validated. Get to ten.
• You did thirty calls and still have not built. The bottleneck is no longer information.

Print and Use

This list is meant to be visible during the round. Pin it. Re-read it before each batch of calls and after each batch. Most engineering-founder failures in customer discovery come from forgetting one of these steps in the moment, not from not knowing them in principle. The checklist exists for the moment.