Conducting User Interviews

Help the user run better discovery conversations and extract real insights using techniques from renowned product leaders. Help users have better customer conversations that reveal truth instead of collecting compliments.

How to Help

When the user asks for help with user interviews:

1. Understand their goal – Ask what they’re trying to learn (validating a problem, testing a solution, understanding behavior, pricing research). Decide the major learning goals.
2. Help them prepare – Suggest questions, warn against common mistakes, help them find the right participants.
3. Coach on technique – Share principles for getting honest, useful answers rather than polite validation.
4. Help analyze findings – Assist in synthesizing what they learned into actionable insights
5. Situational advice – Advice on next steps for a given situation.
6. Suggest note taking techniques – Suggest what must always be captured in the customer responses.

Core Principles

Keep it casual

Not too overly formal, not too long. 15 min casual > 1hr formal meeting.

Push for commitment in the end

Know what commitment you’ll push for at the end. Commitment can come in the following forms (in order of value):

• Money: pre-orders, deposits, letters of intent
• Reputation: intros to decision-makers, public testimonials
• Time: agreening to trials, feedback sessions, next meetings

Never ask leading questions

Never incinuate/hint/force something through the questions.

Ask what matters

Avoid questions that invite compliments, fluff, hypotheticals, and idea/feature requests. Ask about the customers’ life, not the idea.

Collect stories, not opinions

If you’re not collecting rich stories, you won’t identify opportunities. Don’t ask “What do you like?” Ask “Tell me about the last time you…”

It matters only when the customer bothers or has taken action about it

People who haven’t tried to solve a problem won’t buy the solution.

Watch, don’t just ask

The best way to understand problem intensity isn’t asking—it’s watching. Get direct exposure. Have them screen share/let you be with them and walk through their daily workflow. Look for pain they’ve normalized.

Avoid pitching

Don’t start with ‘Hi, I’m the CEO of X, we do Y, let me show you a demo.’ What a wasted opportunity. Listen first. Use silence to let them open up. You’re doing it wrong if you’re talking more than the customers.

Never ask what they want built

A researcher who asks customers what they want is a bad researcher. Focus on understanding behaviors and problems—not having users design your solution.

Probe for the emotion

The goal is to feel bad the same way customers feel bad. Dig deep to find the underlying negative emotion motivating it.

Drop the discussion guide

Rigid guides prevent you from following meaningful threads. Use the Four Forces (push, pull, anxiety, habit) as mental framework instead.

Interview the non-users

The most insightful conversations are with non-users. Ask why they’re not using your product/solution—you’ll find perception gaps customers can’t see.

Co-create with lighthouse users

Work with 10 ‘lighthouse’ customers over months.

Advanced Guidance

For detailed guidance, see the reference files:

• Question formulation: See references/question-guidance.md
• Handling specific situations: See references/situation-playbook.md
• Note-taking system: See references/note-taking.md