Interview Script·45 min·10 questions

Discovering why support tool customers cancel despite initially choosing your solution

You're seeing cancelled customers cite 'cost' or 'missing features' in exit surveys, but these explanations feel incomplete. Teams that actively selected your support tool over competitors are walking away, yet the generic reasons don't explain why they stayed committed through onboarding only to leave months later.

Why standard questions fail here

Direct questions about cancellation reasons trigger rehearsed, socially acceptable answers that protect the customer's decision-making reputation. This script reconstructs the timeline leading to cancellation, anchoring in specific moments when the tool stopped solving real problems, revealing the gap between stated reasons and the actual breakdown in value delivery.

Sample Questions

Grounded in The Mom Test and Jobs-to-be-Done.

Q1 Can you tell me a bit about your role and what your typical day looks like when it comes to customer support?
Why ask this?

Jobs-to-be-Done: establish context for the job they were trying to accomplish

Technique

Use active listening and mirror back key points to build rapport. Let them talk without interrupting.

Follow-up Prompts
  • What does a busy support day look like for your team?
  • How many people are typically involved in support decisions?
Watch out for
  • Generic role descriptions - probe for specific daily tasks and pain points
Q2 Can you walk me through the story of how you originally ended up choosing our support tool? Start from the very beginning - what was happening that made you start looking?
Why ask this?

JTBD hiring moment analysis: understand the struggling moment and forces that led to the original purchase

Technique

Use the timeline technique: get them to narrate chronologically from struggle to solution. Ask 'what happened next?' to keep the story moving.

Follow-up Prompts
  • What was the final straw that made you say 'we need to find something'?
  • Who else was involved in that decision?
  • What were you using before, and why wasn't it working?
Watch out for
  • Skipping to features or rational justifications instead of the emotional struggling moment
Q3 Tell me about the day you actually decided to go with our tool. What was that conversation like?
Why ask this?

JTBD: identify the forces present at moment of purchase to contrast with firing forces

Technique

Dig into the specific moment of decision using the laddering technique - ask 'what made that the deciding factor?' multiple times.

Follow-up Prompts
  • What were your biggest concerns about making that choice?
  • What convinced you it was the right move?
  • What would have happened if you hadn't found a solution?
Watch out for
  • Rational feature comparisons instead of emotional drivers and anxieties
Q4 Think back to when our tool was working best for you. Can you describe a specific day or situation where you thought 'I'm so glad we have this'?
Why ask this?

Mom Test principle: focus on specific past experiences rather than generic opinions about value

Technique

Push for concrete story with specific details - who, what, when, where. Avoid letting them generalize.

Follow-up Prompts
  • What specifically happened that day?
  • How did it feel when that worked smoothly?
  • What would have happened without the tool in that situation?
Watch out for
  • Generic statements like 'it was helpful' without specific scenarios
Q5 What was your team saying about our tool during those good times?
Why ask this?

Social proof validation: understand peak satisfaction from team perspective

Technique

Ask for direct quotes or specific conversations they remember hearing.

Follow-up Prompts
  • Can you remember a specific comment someone made?
  • Who was the biggest champion of the tool on your team?
Watch out for
  • Hypothetical team sentiment instead of actual conversations they witnessed
Q6 Now, thinking about when things started to change - can you tell me about the first time you remember thinking 'this isn't working as well as it used to'?
Why ask this?

JTBD firing forces: identify the initial struggling moment that began the firing process

Technique

Use the critical incident technique - get them to recount one specific moment in detail, including emotions and context.

Follow-up Prompts
  • What was different about that situation?
  • How did that make you feel?
  • What did you do right after that happened?
Watch out for
  • Jumping to rational reasons instead of the emotional turning point

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