Interview Script·45 min·10 questions

Discovering why operations teams still build weekly reports manually despite automation tools

You're watching operations managers spend hours each week pulling data from Salesforce, Google Analytics, and internal dashboards to create status reports. They complain about the manual work, yet they haven't adopted any of the reporting automation tools already available in their stack.

Why standard questions fail here

Direct questions about pain points often get filtered through what people think they should want rather than what actually drives their behavior. This script reconstructs their actual reporting workflow step-by-step, anchoring in their last completed report to reveal the hidden decisions and workarounds that keep them manual despite viable alternatives.

Sample Questions

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

Q1 Can you tell me about your role and what your typical week looks like?
Why ask this?

JTBD: Understanding the job context before diving into specific tasks helps reveal competing priorities and constraints

Technique

Listen for time pressures and competing responsibilities that will influence reporting behavior

Follow-up Prompts
  • What takes up most of your time during a typical week?
  • How does reporting fit into your other responsibilities?
Watch out for
  • Generic job descriptions instead of actual daily activities
Q2 Walk me through exactly what you did the last time you created a weekly status report. Start from the very beginning.
Why ask this?

Mom Test principle: Ask about specific past behavior rather than general processes to get accurate workflow details

Technique

Use the narrative technique - let them tell the story chronologically without interruption, then probe for details

Follow-up Prompts
  • What was the first tool or system you opened?
  • What did you do when you hit that step?
  • How long did that particular part take?
Watch out for
  • Idealized process descriptions instead of what actually happened
  • Vague statements like 'I usually gather data' without specifics
Q3 Tell me about a time when creating your weekly report took much longer than expected. What happened?
Why ask this?

JTBD struggling moment identification: Pain points are most clearly revealed when things go wrong

Technique

Use the critical incident technique - focus on a specific memorable instance rather than general frustrations

Follow-up Prompts
  • What made it take so long that time?
  • How did you eventually solve it?
  • Has something similar happened since then?
Watch out for
  • Generic complaints about reporting instead of specific incident details
Q4 Show me the tools and systems you currently use for reporting. Can you actually pull them up and walk me through them?
Why ask this?

Contextual inquiry principle: Observing actual tools and interfaces reveals workarounds and friction points not captured in interviews alone

Technique

Ask them to share screen or show physical process - watch for clicks, hesitations, and shortcuts they've developed

Follow-up Prompts
  • What's that bookmark you just clicked?
  • Why do you always start with that particular view?
  • What's that spreadsheet you keep open?
Watch out for
  • Describing tools instead of showing actual usage patterns
Q5 Describe the last time you had to stay late or work extra hours because of reporting. What specifically caused that?
Why ask this?

Mom Test: Specific past incidents reveal true pain intensity better than hypothetical questions about frustration

Technique

Probe for emotional impact using the feeling probe technique: 'How did that make you feel?'

Follow-up Prompts
  • How often does this type of thing happen?
  • What would have had to be different to avoid staying late?
  • Who else was affected when this happened?
Watch out for
  • General statements about working late instead of specific incidents
  • Rationalized explanations instead of emotional reactions
Q6 Tell me about any shortcuts, workarounds, or 'hacks' you've developed to make reporting faster or easier.
Why ask this?

Lead user theory: Workarounds reveal both pain points and desired solutions that users have already partially invented

Technique

Use appreciative inquiry - frame workarounds as clever solutions rather than admissions of system failure

Follow-up Prompts
  • How did you figure out that approach?
  • Do other people on your team do something similar?
  • What would happen if you couldn't use that workaround anymore?
Watch out for
  • Claims of following standard processes when most users develop workarounds

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