Interview Script·45 min·10 questions
Discovering why HR teams abandon trials despite actively engaging with features
You're seeing trial users who logged in multiple times, explored key features, maybe even set up team accounts — but then went quiet before converting. The engagement data shows they were genuinely evaluating your product, yet something made them walk away without upgrading.
Why standard questions fail here
Direct questions about why they didn't buy often get surface-level answers like 'budget' or 'timing.' This script reconstructs their actual evaluation timeline, anchoring in specific moments when they were actively using the product, to uncover the precise friction points and missing pieces that derailed their decision-making process.
Sample Questions
Grounded in The Mom Test and Jobs-to-be-Done.
Jobs-to-be-Done: Understanding the broader context before diving into the specific struggling moment
Let them talk freely for 2-3 minutes. Note what they emphasize as important in their role - this context will inform later questions about tool needs
- What are the most time-consuming parts of your day?
- What tools do you rely on most heavily?
- Generic job descriptions without specific daily activities
JTBD: Identifying the struggling moment and initial job-to-be-done that triggered search behavior
Use the 5 Whys technique if they give surface-level answers. Look for emotional language about frustration or pain points
- What was the specific moment you decided you needed to find a new tool?
- How were you handling this before? Walk me through that process.
- Who else was involved in recognizing this need?
- Vague answers like 'we needed something better' without specific trigger events
Mom Test principle: Understanding past behavior and the competitive landscape from user perspective
Ask for specifics about each alternative: What did they try? Why didn't it work? Get concrete examples, not just tool names
- What specifically didn't work about our product?
- How long did you spend evaluating each option?
- What would have made any of those alternatives work for you?
- Lists of tools without explaining what they actually tested or why each failed
Mom Test: Asking for specific past behavior rather than opinions about the onboarding experience
Use the critical incident technique - ask them to narrate step by step, including what they were thinking and feeling at each stage
- What were you expecting to happen at that point?
- How did that make you feel?
- What did you do next when you hit that issue?
- High-level summaries like 'it was confusing' without specific examples of what confused them
JTBD: Identifying friction points and unmet needs during the evaluation process
If they say 'it was fine' or minimize problems, probe deeper: 'Even small hiccups - what's one thing that took longer than expected?'
- What were you trying to accomplish when that happened?
- How did you try to solve it?
- Did you reach out for help? What happened?
- Claims that everything worked perfectly - everyone hits some friction
JTBD: Understanding the actual job they hired the product to do vs. intended use cases
Ask for screen sharing or detailed descriptions. Look for gaps between their use case and product capabilities
- What would success have looked like for that task?
- How were you measuring whether it was working for you?
- What part of your workflow were you hoping to improve?
- Vague descriptions of 'testing it out' without specific use cases
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