Section 01
The Big Picture
Help me understand what you're building and where you are today.
1. In your own words, what is your company or project? Describe it as you would to someone who has never heard of it. *
2. What stage are you in right now? (Pre-launch / Early development / Active build / Scaling / Reinvention) *
3. What does success look like 12 months from now? Be specific — what has to be true for you to feel like this is on track? *
4. What is the single biggest thing that has to go right in the next 90 days? *
5. What keeps you up at night right now? Be direct. *
Section 02
The Entities & Structure
Help me map the full landscape of what you're operating across.
6. List every entity, business unit, or initiative involved in this work. For each, tell me what it does, who leads it, and its current status. *
+ Add another entity
7. Who are your key investors, partners, or stakeholders — and what is their level of involvement? (Passive capital / Active oversight / Board seats / Operational input — and how many total?) *
8. Are there any entities, contracts, or relationships that are complicated, sensitive, or that we should be aware of going into our session?
Section 03
Financials & Business Model
Help me understand the economics of what you're building and how it's structured to capture value.
9. What is your business model — how does revenue actually get generated, and through which products, services, or channels? *
10. Who owns this business, and what's the ownership breakdown? Is there a board, and if so, who's on it? Are there investors or other parties with voting rights or decision-making authority — who are they, and what authority do they hold? *
11. What are your revenue goals for this year and next? Include your current run rate or actuals if you have them.
12. What are your profitability or EBITDA goals, and where do you stand today?
13. What does your cash position and runway look like? Are you currently funded through revenue, debt, equity, or a mix — and are you planning to raise or borrow in the next 12 months?
14. Who manages your financial reporting today — a bookkeeper, controller, CFO, fractional support, or no one formally? How confident are you in the numbers you're currently working from?
15. Do you have a current business plan or financial projections?If yes, we'll follow up with a secure upload link so you can share the file directly — no need to attach it here.
16. What's the biggest financial risk or uncertainty you're carrying right now?
Section 04
Decisions & Priorities
Help me understand what's been decided, what's in progress, and what's still open.
17. List your most important current decisions and where each one stands. *
+ Add another decision
18. Which of these decisions are you most uncertain about? Which ones do you wish someone would just tell you the answer to? *
19. Are there any decisions that have already been made that you're second-guessing?
20. Are there decisions being made by others — investors, partners, boards, or external parties — that you're waiting on?
Section 05
People, Resources & Structure
Help me understand who you have, what you're building toward, and where the gaps are.
21. Who is currently working on this in any capacity? List names or roles, whether they're full-time, part-time, contractor, or vendor, what they own, and when they started or are starting. *
+ Add another person
22. What roles do you know you need in the next 6 months? What roles are you still unsure about? *
23. Do you have a sense of what should be in-house versus contracted versus vendor-managed? Where are you most uncertain?
24. Are there any leadership or organizational structure decisions that haven't been made yet? What are they, and what's driving the uncertainty?
25. What does your budget look like for team-building and operations in the next 12 months? (A rough range is fine.)
Section 06
The Opportunity & The Gap
Help me understand where you see the biggest upside — and where you feel most exposed.
26. What is the biggest opportunity you're not yet capturing — or not moving fast enough on? *
27. Where do you feel most exposed right now? What would a well-resourced competitor do that you can't yet? *
28. What are the 2–3 areas of your business or project where you have the least clarity right now? *
29. Where are you at risk of duplicating cost, effort, or resources — either across entities, teams, or vendors?
30. Who are the 3–5 partners, vendors, or relationships most critical to your success — and what is the status of each?
31. What do you most want to walk out of our session with clarity on? *
32. Anything else we should know before we meet? (Context, history, tension, or nuance that doesn't fit neatly into any of the questions above — more is more.)
