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.