Interview Script·45 min·10 questions
Discovering why first-time founders hit unexpected walls despite startup preparation
You're seeing first-time founders struggle with challenges they never anticipated, even after extensive planning and research. Despite consuming startup content, attending accelerators, or having business experience, they're hitting roadblocks that don't match the typical advice about product-market fit or fundraising.
Why standard questions fail here
Generic questions about 'challenges' produce sanitized answers that mirror startup blog posts. This script anchors in specific moments when founders felt most stuck or surprised, reconstructing the timeline from their initial confidence to the point where reality diverged from expectations.
Sample Questions
Grounded in The Mom Test and Jobs-to-be-Done.
Establishes timeline and context while allowing participant to ease into conversation
Let them talk without interruption. Note key dates and business type for follow-up context
- What made you decide to start this particular business?
- Had you ever started a company before this one?
- Generic elevator pitch instead of personal timeline
Mom Test principle: ask about specific past experiences rather than general opinions. JTBD: identify struggling moments
Use the laddering technique - ask for concrete details about one specific week, then drill down into daily activities and emotions
- What specifically made that week so difficult?
- How were you spending most of your time that week?
- What kept you up at night during that period?
- Vague statements like 'everything was hard' without specific examples
- Generic startup advice instead of personal experience
Jobs-to-be-Done struggling moment identification - emotional peaks reveal core problems
Probe for the emotional context first, then drill into the situational factors. Ask 'why' multiple times
- What triggered that feeling of being overwhelmed?
- Who did you turn to for help, if anyone?
- How long did that feeling last?
- Hypothetical 'founders generally feel overwhelmed' instead of personal story
- Solutions offered instead of problem description
Mom Test: focus on specific past behavior and emotions rather than general sentiment
Remain silent after asking - let them process the emotional weight. Then use mirroring technique to reflect back key phrases
- What specific events or realizations triggered those doubts?
- How did you work through that moment?
- What almost made you quit?
- Philosophical statements about entrepreneurship instead of specific doubt moments
- Overly positive responses that avoid the struggle
Behavioral interviewing: focus on actual process and decision-making rather than opinions about hiring
Use the SOAR technique - ask about Situation, Obstacles, Actions, and Results in sequence
- What mistakes did you make during that process?
- What would you do differently knowing what you know now?
- How did you know when you needed help versus trying to do it yourself?
- General hiring advice instead of personal experience
- Hypothetical 'I would hire for culture fit' without specific examples
JTBD: uncover how founders navigate uncertainty, which is core to startup challenges
Focus on the decision-making process, not the outcome. Use the 5 Whys technique to understand their reasoning
- What information did you wish you had at the time?
- Who did you consult with, if anyone?
- How did you deal with the stress of not knowing if you were making the right choice?
- Generic business advice about decision-making
- Retrospective wisdom rather than describing the actual uncertainty felt
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