Session Prep
Walking into a session with a finance expert unprepared means you'll spend half the time giving context instead of getting answers. Preparation is especially important for finance — because the most valuable advice is always situational. A generic question gets a generic answer. This guide is organized into three sections: understanding your current financial position, fundraising and financial modeling, and planning your next steps. Before your session, review all three and mark the questions most relevant to your situation. Bring any relevant numbers — cash balance, burn rate, revenue — even rough estimates. The more specific you are, the more specific the guidance you'll get. If you have 10 questions listed and only 60 minutes, prioritize the ones tied to decisions you have to make in the next 30–90 days.
1.Based on what I've shared, what's the most important financial lever I should be focused on right now?
Forces them to prioritize — a good advisor won't say 'it depends' without giving you a concrete starting point.
2.What does a healthy cash flow position look like for a business like mine?
Gets you a benchmark specific to your stage and type — not generic advice.
3.How should I be thinking about the relationship between growth and profitability at my current stage?
This question reveals how they think about trade-offs, not just optimization.
4.Are there any obvious inefficiencies or risks in how I'm currently managing money that I should address first?
A quick diagnostic that often surfaces things you've normalized but shouldn't have.
5.What financial metrics do investors in my space typically focus on, and how do I stack up?
If you're raising, this is more valuable than any generic fundraising advice.
6.What assumptions in my financial model are most likely to be challenged by investors?
Gets you ready for the hard questions before you're in the room.
7.How much runway should I be targeting before my next raise?
Context-specific advice that depends on your market, team, and traction.
8.What financial decisions should I avoid making without getting advice first?
Helps you understand where DIY gets dangerous versus where it's fine.
9.If you were in my position, what would you do in the next 90 days?
Forces a concrete, prioritized recommendation — not a list of considerations.
10.What information or data should I be tracking that I'm probably not tracking yet?
Reveals gaps in your financial visibility that could matter later.