Diligence Meeting Prep

description: Prepare for due diligence meetings — management presentations, expert network calls, customer references, and advisor sessions. Generates targeted question lists, benchmarks to reference, and red flags to probe. Use before any diligence meeting or call. Triggers on "prep for management meeting", "diligence call prep", "expert call questions", "customer reference questions", or "meeting prep for [company]".

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:

Meeting logistics: Who, when, where, duration
Objectives: Top 3 things you need to learn from this meeting
Question list: Prioritized, grouped by topic (star the must-asks)
Benchmarks: Key numbers to reference
Red flags: Specific items to probe
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