Overview
When acquiring a business or working with a previous owner who’s reluctant to share knowledge, the direct approach rarely works. Asking someone to “walk you through how everything works” puts them on the defensive. Instead, use the quoting process as your entry point—it naturally exposes the entire business operation without triggering resistance.
Key Takeaways
- Quoting is your best entry point for extracting business knowledge from reluctant sources
- The edge cases in quoting reveal how the entire business actually operates
- Build your own quote tool afterward to force even deeper questions
- Spend 2 hours documenting everything you learn after each quoting session
- ISO/process documentation work is an alternative entry point for systems-related businesses
The Strategic Approach
Don’t start with: “Walk me through how this works. I’m going to write down everything you say.”
Instead, start with: “Can you help me with our quoting procedure?” or “Help me use your quoting tool.”
This works because quoting touches every part of the business:
- Cost structures - How processes are priced, labor allocation
- Pricing strategies - Margins, customer-specific pricing, delivery fees
- Customer relationships - Preferences, special arrangements, history
- Internal processes - Who does what, how long things take, equipment used
What You’ll Learn Through Quoting
By working through quotes over a few months, you’ll organically discover:
- Customer-specific knowledge - “This customer likes delivery, add $100”
- Process costs - “This uses two people, not one—costs more”
- Business logic - How they think about pricing decisions
- Hidden costs - Utilities, overhead, materials that aren’t obvious
The Documentation Process
After each quoting session:
- Spend 2 hours documenting everything you learned
- Capture processes - Internal workflows you observed
- Note customer preferences - Special handling, pricing exceptions
- Record cost structures - Where numbers come from
- Ask follow-up questions - “You said this costs X for this process—can you walk me through that?”
Level Up: Build Your Own Quote Tool
Once you understand the existing process, build your own quoting tool. This forces deeper questions:
- “He used $20 for utilities—where did that come from?”
- “I need to look at our utility bills to understand this.”
Whether it’s Excel, no-code, or a custom app doesn’t matter. The act of building reveals gaps in your understanding.
Action Items
- Ask to help with quoting instead of asking for process explanations
- Schedule regular quoting sessions over 2-3 months
- Document learnings for 2 hours after each session
- Build your own quote tool to solidify understanding
- Use follow-up questions to expand into related processes