Problem Interviews Checklist for Busy First-Time Founders

This is the working checklist. Skip the reading, just run the steps. Designed for first-time founders with limited time, no team, and a need to actually finish the work.

Before You Start (One-Time Setup)

• Define the audience with two filters: a job-or-role and a recent behavior. Examples: solo SaaS founders who shipped in the last 12 months; agency operations leads at firms under 20 people.
• Write your 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.

Sourcing the Calls

• Make a list of 40 candidates who fit the audience filter.
• Send each a three-sentence message: why them, what you are researching, ask for 30 minutes.
• Promise no pitch, and keep it.
• Aim to land 15 calls. Reply rates of 25 to 40 percent are normal.
• Send messages in batches of 10 over a few days. Do not flood your calendar.

Five Minutes Before the Call

• Open the notes doc to a fresh entry. Add date, name, role.
• Re-read the three questions. Stick them on the corner of your screen.
• Ask permission to record at the start of the call if you intend to.
• Remind yourself: you are not pitching today.

During the Call

• Open with a low-stakes intro. State you are researching, not selling.
• Ask question one (the story prompt). Then listen.
• After every answer, count to three before responding. Use the silence.
• When something is interesting or vague, ask: "Tell me more about that."
• Capture exact phrases when they say something specific or vivid.
• If asked what you are building, deflect: "Still figuring it out, can we come back to that at the end?"
• End on time. Thank them. Ask if they would be open to a follow-up later.

Within Ten Minutes After the Call

• Add three things to the bottom of your notes: the trigger event that caused the problem, what they actually did, and one thing that surprised you.
• Mark any direct quotes that stood out with a star or asterisk so you can find them later.
• Note any name, tool, or workaround you should look up afterward.

After Every Five Calls

• Reread the last five sets of notes back-to-back.
• Write down patterns you see appearing more than once: same workaround, same vocabulary, same trigger.
• Write down disconfirmations: things you assumed that have not held up.
• Adjust your three questions if you keep wishing you had asked something different.

After Fifteen Calls

• Answer in one sentence each: who is the customer, what is the problem, what is the existing workaround.
• If you can answer those clearly: stop interviewing and start building the smallest possible version.
• If you cannot, decide whether the issue is your audience filter, your questions, or whether the problem is just less coherent than you thought.
• Either way, 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 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 anything. The bottleneck is no longer information.

Print It and Use It

This checklist is meant to be printed and pinned somewhere you will see it. The whole point of a checklist is that it survives the moments where you forget what you read. If you run through it before each batch of calls and after each batch, you will avoid almost every common first-time founder mistake without having to remember to.