The 30-Minute Assessment: Questions to Ask in the First Meeting

The 30-Minute Assessment: Questions to Ask in the First Meeting

Rapid Structural Diagnosis

These five questions can be answered in a first meeting with the right prompts. Here’s exactly what to ask:

For Question 1 (AI Replication):

“Walk me through what happens if a well-funded competitor decides to replicate your core functionality using AI.”

Listen for:

  • Integration depth
  • Proprietary data
  • Workflow complexity
  • Regulatory embedding

For Question 2 (Switching Cost):

“If one of your customers decided to switch to a competitor tomorrow, what would that process look like? How long? How much would it cost them?”

Listen for:

  • Specific friction points
  • Migration complexity
  • Integration dependencies
  • Not vague claims

For Question 3 (System of Record):

“What data do your customers have in your system that they couldn’t get anywhere else? How often do they query historical data?”

Listen for:

  • System-of-record language
  • Historical analysis use cases
  • “Source of truth” references

For Question 4 (Services Layer):

“What does your implementation process look like? How long does it take? What does your professional services revenue look like?”

Listen for:

  • Meaningful services investment
  • Implementation timelines
  • Services revenue percentage

For Question 5 (Compounding Data Gravity):

“Is a customer who’s been with you for 5 years more locked-in than a customer who joined last year? Why specifically?”

Listen for:

  • Compounding mechanisms
  • Not just habit
  • Specific value accumulation

The Decision Rule

If the answers are clear, you have your classification.

If the answers are ambiguous, it’s middle. Pass.


This is part of a comprehensive analysis. Read the full analysis on The Business Engineer.

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