Hiring a fractional CFO can be one of the most impactful decisions your startup makes. But not all CFOs are created equal—and the wrong fit can cost you time, money, and momentum.
Before you bring one on board, ask these 10 questions to make sure they have the expertise, mindset, and flexibility your stage requires. Here’s what to ask—and why it matters.
1. What experience do you have working with startups at my stage?
Not all financial expertise translates to early-stage environments. A CFO who’s only worked in late-stage or corporate finance may not be comfortable in a lean, fast-moving startup. You want someone who understands your current challenges—whether it’s managing burn, prepping for a raise, or scaling operations.
Why it matters: The right CFO meets you where you are and helps you grow without overcomplicating things.
2. What industries or business models do you specialize in?
A SaaS startup has very different financial needs than an ecommerce brand or services firm. From understanding MRR to inventory management or margin optimization, your CFO should speak the language of your business model.
Why it matters: Industry-aligned CFOs can offer sharper insights and avoid a learning curve at your expense.
3. How do you typically work with founders and leadership teams?
You want a CFO who is collaborative, proactive, and aligned with your leadership style. The best CFOs go beyond following directions and creating analysis—they anticipate needs, spot trends, and offer solutions.
Why it matters: You’re not just hiring for skills—you’re hiring for chemistry and communication.
4. What drivers and metrics do you see as most critical for our business model?
This question uncovers their strategic depth. A strong CFO should be able to explain how they build models, what assumptions they test, and how they help you plan for different scenarios. If you explain your business, they should be intuitively know what metrics and drivers will matter most for it.
Why it matters: Forecasting isn’t just a spreadsheet—it’s the basis for your growth strategy and investor confidence.
5. What tools will you need to access?
Your CFO should be familiar with tools like QuickBooks, Gusto, Ramp, or SaaS metrics platforms—whatever is relevant to your stack. If they’re not comfortable in these platforms, you’ll be stuck pulling reports for them and digging through details to answer their questions.
Why it matters: Tech-savvy CFOs work faster, require less hand-holding, and go beyond the surface level.
6. How do you support fundraising and investor communications?
Whether you’re raising a Seed round or preparing for Series B, your CFO should be able to build a clean, investor-ready data room, craft a compelling financial narrative, and confidently field investor questions. But beyond the raise itself, it’s just as important to understand how they manage ongoing investor reporting and board communications—do they bring clarity and confidence to the numbers, or just share dashboards?
Ask for specific examples: Have they supported clients through successful funding rounds? What role did they play in those processes—were they leading the charge or reacting to founder direction? Dig into how they maintained investor trust after the raise through consistent, transparent updates.
Why it matters: Fundraising success often hinges on clear, credible financials—and a CFO who knows how to deliver them.
7. What are your strengths—and what’s outside your scope?
A great way to understand a CFO’s fit is by asking about their background. Those with investment banking, VC, or private equity experience are often stronger in capital raises, investor relations, and crafting compelling board materials. On the other hand, CFOs with a background in FP&A, corporate finance, or accounting may excel at improving profitability, identifying cost savings, managing compliance risks, and streamlining operations.
No CFO is great at everything—so it’s smart to ask where they thrive and where they lean on others.
Why it matters: Set expectations up front and avoid gaps in coverage.
8. What does your typical engagement look like (hours, cadence, deliverables)?
Ask how they work—weekly calls, monthly board prep, ad hoc support—and how flexible they are as your needs evolve.
Structure is important to fractional CFO engagements, so beware of hourly “as-needed” support. A monthly retainer fee with clear, recurring deliverables ensures that your CFO will stay involved and proactive, rather than waiting for instructions and playing catch-up when you need their help.
Why it matters: You want a partner who is consistently plugged-in, and ready to ramp-up when your needs intensify.
9. Can you share specifics examples of success/impact?
Ask for specific wins: a capital raise, push to profitability, a specific analysis that led to material insight/outcome. They should be willing to provide references to one or two clients cited in these examples.
Why it matters: Past performance is the best indicator of what it can help you achieve.
10. How do you measure success in your role?
Great CFOs think beyond spreadsheets—they care about strategic outcomes. Whether it’s increased runway, better board engagement, or capital raised, they should have a clear sense of what success looks like.
Why it matters: You want a CFO who takes ownership and creates material value—not one who believes the job is done once numbers are delivered.
Final Thought
Hiring a fractional CFO is more than filling a financial role—it’s bringing on a partner who helps you lead with clarity, confidence, and control. Ask smart questions up front, and you’ll find someone who fits your stage, speaks your language, and helps your startup thrive.
