Interviewing Techniques

Questioning Toolkit by Purpose

Problem Discovery

Understand if problem is real and worth solving.

• "Tell me about the last time you [encountered this problem]."
• "What was the hardest part about that?"
• "What did you do about it?" | "What don't you love about that solution?" | "What else have you tried?"

Understanding the Job

Map the job-to-be-done and desired outcomes.

• "What are you ultimately trying to accomplish?"
• "Walk me through your process step by step."
• "At each step, how do you know if you've succeeded?"
• "What slows you down or frustrates you most?" | "What workarounds have you created?"

Probing Assumptions

Challenge beliefs and uncover truth.

• "What makes you believe that?" | "What would need to be true for this to work?"
• "What could we assume instead?" | "What would change your mind?"

Testing Commitment

Distinguish interest from commitment.

• "Would you be willing to [specific action]?" | "What would you pay for this?"
• "Can you introduce me to someone else with this problem?" | "When can we schedule a follow-up?"

Exploring Implications

Understand impact and urgency.

• "If this were solved, what would change?" | "What would that enable you to do?"
• "What would happen if we didn't solve this?"

Interview Conduct Rules

Do: Ask about past specifics | Open, non-directive questions | Seek commitment not praise | Keep informal | 80% listening | Talk about their life first

Avoid: Future behavior questions | Leading questions | Accepting compliments as validation | Talking >20% | Mentioning idea before understanding problem | Formal settings

Assumption Challenging

Triggers

Challenge when: belief without evidence | prediction about future | negative feedback dismissed | skipping to solution | single data point relied on

Challenge Format

1. "What evidence supports this?" -- specific past examples
2. "What would disprove this?" -- falsification criteria
3. "What's the opposite assumption?" -- explore alternatives
4. "Who would disagree and why?" -- disconfirming perspectives

Tone: curious and supportive, not confrontational -- goal is truth-seeking.

Assumption Testing Framework

Assumption Categories

Risk Scoring

Risk Score = (Impact x 3) + (Uncertainty x 2) + (Ease x 1)

Hypothesis Template

We believe [doing X] for [user type] will achieve [outcome].
We will know this is TRUE when we see [measurable signal].
We will know this is FALSE when we see [counter-signal or absence of signal].

Test Methods by Category

Decision Rules