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

Category	Core Question
Value	Will customers want this?
Usability	Can customers use this?
Feasibility	Can we build this?
Viability	Does this work for our business?

Risk Scoring

Factor	Weight	Low (1)	Medium (2)	High (3)
Impact if wrong	3	Minor adjustment	Significant rework	Solution fails
Uncertainty	2	Have data	Mixed signals	Speculation
Ease of testing	1	Days, low cost	Weeks, moderate	Months, high cost

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

Priority	Score	Action
Test first	> 12	Immediate
Test soon	8-12	Schedule
Test later	< 8	Backlog

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

Category	Methods
Value	Landing page, Fake door, Mom Test interviews
Usability	Prototype testing, 5-second tests, Task completion
Feasibility	Spike, Technical prototype, Expert review
Viability	Lean Canvas review, Stakeholder interviews

Decision Rules

Result	Criteria	Action
Proven	>80% meet success criteria	Proceed
Disproven	<20% meet criteria	Pivot or kill
Inconclusive	20-80%	Increase sample, try different method, segment