Diligence Meeting Prep

Workflow

Step 1: Meeting Context

Ask the user for:

• Meeting type: Management presentation, expert call, customer reference, advisor check-in, site visit
• Attendees: Who from the target company or third party
• Topic focus: Full business overview, or specific workstream (financial, commercial, operational, tech)
• What you already know: Prior meetings, CIM, data room findings
• Key concerns: Specific issues to probe

Step 2: Generate Question List

Organize questions by priority and topic. Structure depends on meeting type:

Management Presentation

Business Overview (warm-up)

• Walk us through the founding story and key milestones
• How do you describe the business to someone unfamiliar with the space?
• What are you most proud of? What would you do differently?

Revenue & Growth

• Walk us through revenue by customer/segment/geography
• What's driving growth? Price vs. volume vs. new customers
• What does the sales cycle look like? How has win rate trended?
• Where do you see the biggest growth opportunities in the next 3-5 years?

Competitive Positioning

• Who do you lose deals to and why?
• What's your moat? How defensible is it?
• How do customers evaluate you vs. alternatives?

Operations & Team

• Walk us through the org chart — who are the key people?
• What roles are you hiring for? What's been hardest to fill?
• What keeps you up at night operationally?

Financial Deep-Dive

• Walk us through the margin bridge — what's changed and why?
• Any one-time or non-recurring items we should understand?
• How do you think about capex — maintenance vs. growth?
• Working capital seasonality?

Forward Look

• Walk us through the budget/plan for next year
• What assumptions are you most/least confident in?
• What would need to go right/wrong to significantly beat/miss plan?

Expert Network Call

• How do you view [company]'s positioning in the market?
• What are the secular trends driving this space?
• Who are the strongest competitors and why?
• What risks should an investor be aware of?
• If you were buying this business, what would you diligence most carefully?

Customer Reference Call

• How did you find [company] and why did you choose them?
• What alternatives did you evaluate?
• What do they do well? Where could they improve?
• How likely are you to renew/expand? What would change that?
• If they raised prices 10-20%, how would you react?

Step 3: Benchmarks & Context

For each key topic, provide relevant benchmarks:

• Industry growth rates and margin profiles
• Comparable company metrics (if comps analysis exists in session)
• Data points from the CIM or data room that warrant follow-up
• Discrepancies between different data sources to clarify

Step 4: Red Flags to Probe

Based on what's known, flag specific areas to dig into:

• Inconsistencies in the CIM or financials
• Customer concentration or churn signals
• Management team gaps or recent departures
• Unusual accounting treatments
• Missing data room items

Step 5: Output

One-page meeting prep doc:

1. Meeting logistics: Who, when, where, duration
2. Objectives: Top 3 things you need to learn from this meeting
3. Question list: Prioritized, grouped by topic (star the must-asks)
4. Benchmarks: Key numbers to reference
5. Red flags: Specific items to probe
6. Follow-up items: What to request after the meeting

Important Notes

• Lead with open-ended questions — let management talk, then follow up on specifics
• Don't lead the witness — ask neutral questions, not "isn't it true that..."
• Take notes on body language and confidence levels, not just answers
• Always end with: "What haven't we asked about that we should?"
• Keep the question list to 15-20 max — you won't get through more in a 60-90 min session