Interview Script·45 min·9 questions

Discovering why top AEs succeed despite using generic productivity tools

You're building a deal tracking and call prep tool, but you need to understand how high-performing account executives actually work day-to-day. You have assumptions about their workflow and pain points, but you're not sure where your tool would genuinely fit into their existing systems versus just adding another dashboard they'll ignore.

Why standard questions fail here

Direct questions about productivity habits yield sanitized answers that sound good but miss the messy reality. This script uses timeline reconstruction to walk top performers through their actual recent days, revealing the micro-decisions, workarounds, and hidden time drains that separate them from average AEs.

Sample Questions

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

Q1 Can you walk me through what your role entails and how long you've been in this position?
Why ask this?

JTBD: Understanding job context before diving into workflow specifics

Technique

Let them define success metrics in their own words - don't impose typical sales metrics

Follow-up Prompts
  • What does a successful month look like for you specifically?
  • How is that different from when you started in sales?
Watch out for
  • Generic job descriptions instead of personal experience
  • Focus on what they should do vs what they actually do
Q2 Tell me about yesterday - can you walk me through how you actually spent your time from when you started work until you finished?
Why ask this?

Mom Test principle: Ask about specific past behavior rather than hypothetical typical days

Technique

Use the 'give me a tour' technique - ask them to narrate hour by hour like you're watching over their shoulder

Follow-up Prompts
  • What pulled you away from what you had planned to do?
  • When did you feel most/least productive and why?
  • What tools did you switch between during that time?
Watch out for
  • Idealized version of their day instead of actual yesterday
  • High-level summaries without specific details
Q3 Think about the last deal you closed - can you walk me through everything you had to do to move it from first contact to signature?
Why ask this?

JTBD: Map the complete job of closing a deal to identify all touchpoints and pain points

Technique

Use temporal laddering - ask for the sequence of events and what triggered each step

Follow-up Prompts
  • What information did you need to gather before each call?
  • Where did you keep track of all the details?
  • What almost went wrong that you had to fix?
Watch out for
  • Perfect case scenario instead of messy reality
  • Missing the administrative and coordination work between meetings
Q4 Tell me about the last time you felt completely overwhelmed by your pipeline - what was happening?
Why ask this?

JTBD: Identify struggling moments where users are most motivated to change behavior

Technique

Probe for emotional triggers and specific circumstances that create overwhelm

Follow-up Prompts
  • What specifically made it feel unmanageable?
  • How did you dig yourself out of that situation?
  • What warning signs tell you when you're heading toward that state again?
Watch out for
  • Vague statements about being busy
  • Solutions they think they need instead of problems they experienced
Q5 Show me how you currently prepare for an important prospect call - can you walk me through your actual process?
Why ask this?

Ethnographic observation: Understanding current tools and workarounds in context of real task

Technique

Ask them to screenshare or describe step-by-step actions, not just tools they use

Follow-up Prompts
  • Where do you get stuck in this process?
  • What do you do when you only have 10 minutes to prep instead of an hour?
  • What information do you wish you had but can never find quickly?
Watch out for
  • List of tools without showing actual workflow
  • Idealized prep process instead of rushed reality
Q6 Tell me about the last time you lost track of important information about a deal - what happened?
Why ask this?

Mom Test: Focus on past specific failure rather than hypothetical problems

Technique

Use the 'worst case' technique to uncover hidden pain points they've adapted to live with

Follow-up Prompts
  • How did you realize the information was lost?
  • What did you have to do to recover?
  • How do you prevent this now?
Watch out for
  • Perfect system claims with no examples of failure
  • Blame on external factors instead of process breakdown

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