8 Strategic Questions to Ask the CFO in 2025

Beyond the Balance Sheet: The Strategic Dialogue Your Startup Needs

For startup founders, the Chief Financial Officer is more than just a numbers person; they are a strategic partner crucial for navigating growth, mitigating risk, and allocating capital effectively. The right conversation can unlock insights that shape your company’s trajectory for years to come. However, knowing the right questions to ask the CFO is paramount. Moving beyond surface-level inquiries about revenue and expenses allows you to tap into the strategic depth a high-caliber financial leader provides.

This is especially true for lean startups and small businesses leveraging fractional executives, where every hour of engagement must deliver maximum value. This guide outlines eight essential categories of questions to ask the CFO, designed to uncover deep insights into your company’s financial health, operational efficiency, and long-term strategic positioning. These aren’t just checklist items; they are conversation starters. Use them to build a robust financial foundation and make smarter, data-driven decisions for sustainable growth and profitability.

1. What are our biggest financial risks and how are we mitigating them?

Understanding how a Chief Financial Officer perceives and handles risk is fundamental to evaluating their strategic value. This question moves beyond simple financial reporting and probes their ability to safeguard the company’s future. It assesses their foresight in identifying potential financial vulnerabilities, such as market volatility, supply chain disruptions, credit risks from customers, regulatory changes, or even internal operational failures. A strong CFO won’t just list risks; they will detail a proactive and layered mitigation plan.

This is a critical question to ask the CFO because their answer reveals their strategic mindset and preparedness. For instance, a SaaS company’s CFO might identify customer churn and data security breaches as primary risks. Their mitigation strategy could involve implementing loyalty programs to reduce churn and investing in robust cybersecurity infrastructure, backed by a comprehensive insurance policy. Similarly, a manufacturing startup might face significant supply chain risks. A competent CFO, like those who navigated the semiconductor shortages, would have strategies like supplier diversification, building up safety stock, and negotiating flexible supplier contracts.

Actionable Insights:

When you pose this question, dig deeper for specific, actionable details:

• Quantify the Impact: Ask for a quantified assessment of the top three risks. For example, “A 10% increase in raw material costs would decrease our gross margin by 2%.” This shows they have modeled the potential damage.
• Stress Testing: Inquire about their stress testing methodologies. How do they simulate a crisis, like a sudden recession or the loss of a major client? Understanding their process reveals their level of preparedness.
• Review Cadence: How often are risk assessments reviewed and updated? A quarterly review cycle is standard, but high-growth or volatile industries may require more frequent updates.
• Integration with Other Functions: Explore how the risk management plan integrates with the company’s insurance programs and compliance efforts. This demonstrates a holistic approach rather than a siloed financial view. For more details on building a comprehensive framework, you can explore various risk management strategies on useshiny.com.

2. How is our cash flow performing and what’s our cash runway?

For any company, especially a startup or a high-growth business, cash is the lifeblood. This fundamental question assesses the company’s immediate health and long-term sustainability. It goes beyond profit on paper to examine actual liquidity, revealing how efficiently the business generates and uses cash. A CFO’s answer will demonstrate their grasp on operational efficiency, working capital management, and the organization’s ability to fund daily operations, strategic investments, and unexpected challenges without needing immediate external financing.

This is one of the most critical questions to ask the CFO because their response highlights their hands-on control of the company’s finances. For example, a CFO at a rapidly expanding company like Amazon in its early days would have focused on managing operating cash flow to fuel growth without relying solely on equity financing. In contrast, during the COVID-19 pandemic, a savvy CFO at an airline like Southwest would have detailed cash preservation strategies, including negotiating with suppliers and managing capital expenditures, to extend their cash runway during a period of near-zero revenue. Their ability to explain these levers is a direct measure of their competency.

Actionable Insights:

When discussing cash flow, press for granular detail to understand their level of oversight:

• Forecasting Precision: Ask for their standard cash flow forecasting model, such as a 13-week rolling cash flow forecast. This short-term view is critical for managing liquidity and identifying potential shortfalls before they become a crisis.
• Key Driver Analysis: Inquire about the primary drivers of cash flow. Are they from operations (e.g., customer payments), investing (e.g., asset sales), or financing (e.g., drawing on a credit line)? Understanding the distinction between cash flow from operations vs. free cash flow is essential.
• Sensitivity and Scenarios: A great CFO will have performed sensitivity analysis. Ask, “How would a 30-day delay in our top five customers’ payments affect our cash position?” or “What is our runway if revenue drops by 20% for two consecutive quarters?”
• Working Capital Levers: Explore their strategies for optimizing working capital. How are they managing days sales outstanding (DSO), days payable outstanding (DPO), and inventory turnover? Small improvements here can unlock significant cash. For deeper insights into financial metrics, you can learn more about key performance indicators on our blog.

3. What are our key financial metrics and how do we compare to industry benchmarks?

A company’s choice of key performance indicators (KPIs) reveals its strategic priorities and operational focus. This question probes which financial and operational metrics the CFO believes are most critical for steering the company toward success. It goes beyond top-line revenue, digging into the core drivers of profitability, efficiency, and growth. A strategic CFO will not only identify these metrics but will also contextualize them with industry benchmarks to provide a clear picture of the company’s competitive positioning.

This is one of the most vital questions to ask the CFO because it clarifies how performance is defined and measured. For instance, a CFO at a B2B SaaS company like Salesforce will be laser-focused on metrics such as Annual Recurring Revenue (ARR), Customer Lifetime Value (CLV), and Customer Acquisition Cost (CAC), benchmarking them against other high-growth software firms. Conversely, a retail giant like Walmart’s CFO would prioritize metrics like inventory turnover and Return on Invested Capital (ROIC) to gauge operational efficiency against competitors. The answer demonstrates whether the CFO is simply tracking numbers or using them to drive strategic decisions and identify areas for improvement.

Actionable Insights:

When discussing KPIs and benchmarks, push for a deeper understanding of the “why” behind the “what”:

• Rationale for Selection: Ask why specific KPIs were chosen. A strong CFO should be able to articulate how each metric directly links to the company’s strategic goals and value creation. For example, “We focus on ‘magic number’ because it tells us the efficiency of our sales and marketing spend in generating new recurring revenue.”
• Data Sources and Reliability: Inquire about the sources used for industry benchmarks. Are they from reputable industry reports, private data services, or informal networks? Understanding the data’s quality is crucial for trusting the comparisons.
• Metric Evolution: How have the company’s key metrics changed over time, and what might trigger future changes? This shows foresight and an ability to adapt the performance framework as the business model and market evolve.
• Link to Incentives: Explore how these KPIs are tied to team performance and executive compensation. A well-aligned incentive structure ensures that the entire organization is motivated to improve the metrics that matter most.

4. What is our current debt structure and capital allocation strategy?

How a company finances its operations and deploys its capital is a direct reflection of its strategic priorities and the CFO’s financial philosophy. This question probes into the heart of the company’s financial architecture, examining the balance between debt and equity, the cost of capital, and the discipline behind investment decisions. It reveals whether the CFO favors aggressive growth fueled by leverage or a more conservative, internally funded approach. A top-tier CFO will articulate a clear framework for how every dollar is put to work to maximize long-term value.

This is one of the most critical questions to ask the CFO because their answer illustrates their command of corporate finance fundamentals and their alignment with shareholder interests. Consider Amazon’s long-standing strategy of reinvesting nearly all cash flow back into the business to fuel relentless growth, a stark contrast to a mature company like Apple, which systematically returns massive amounts of capital to shareholders through dividends and buybacks. A startup CFO might explain their use of venture debt to extend runway without significant equity dilution, detailing the specific covenants and repayment schedules. Their ability to explain these choices demonstrates strategic financial management, not just bookkeeping.

Actionable Insights:

When discussing capital structure and allocation, push for concrete details on their methodology:

• Debt Profile: Ask for a breakdown of the debt maturity ladder. “What are our refinancing plans for debt maturing in the next 24 months?” This assesses their forward-looking management of liabilities. Also, inquire about covenant compliance and the amount of headroom available to avoid defaults.
• Capital Allocation Process: Who makes the final call on major capital expenditures? Is there a formal committee or process? Understanding this reveals the governance and discipline behind investment decisions.
• Return Thresholds: What are the minimum acceptable returns for new projects? Ask about the hurdle rates (e.g., Internal Rate of Return or IRR) they use for different types of investments, such as R&D, new market entry, or technology upgrades. This shows they have a quantifiable, non-emotional basis for greenlighting projects.
• Scenario Planning: How does the capital allocation strategy change under different economic conditions, like a sudden rise in interest rates or a market downturn? A prepared CFO will have modeled these scenarios and can explain how they would pivot their strategy to preserve capital or seize opportunities. You can find more on this in McKinsey’s capital allocation frameworks, which emphasize dynamic reallocation.

5. How are we managing costs and what efficiency initiatives are underway?

A CFO’s approach to cost management is a direct reflection of their operational acumen and strategic discipline. This question goes beyond simple budget cuts; it probes their philosophy on creating a lean, efficient organization that can sustain growth. It reveals how they balance the immediate need for cost control with long-term investments in innovation and scale. A visionary CFO doesn’t just cut expenses; they re-architect processes to eliminate waste and drive lasting value.

This is a vital question to ask the CFO because it demonstrates their ability to act as a strategic business partner, not just a financial gatekeeper. For instance, a fintech CFO might focus on lowering customer acquisition cost (CAC) by optimizing marketing spend and improving conversion funnels. In contrast, a healthtech company’s CFO might champion initiatives to reduce the cost of care delivery through telemedicine platforms and automated administrative workflows. A strong answer will showcase specific, data-driven programs, such as Walmart’s famous supply chain optimizations or Netflix’s use of technology to lower the cost per subscriber.

Actionable Insights:

When discussing cost efficiency, focus on the underlying strategy and its impact:

• Request Specific Examples: Ask for recent examples of cost-saving initiatives and their tangible results. For example, “We implemented a new procurement software that reduced our SaaS spend by 15% in the last quarter.” This provides concrete evidence of their effectiveness.
• Inquire About Key Metrics: Discuss the key performance indicators (KPIs) they use to track efficiency. This could be cost per unit, employee productivity, or customer lifetime value to CAC ratio. This shows they are managing by the numbers.
• Balance Cost vs. Investment: Explore how they decide when to cut costs versus when to invest. Ask, “How do you evaluate the ROI on a new technology or headcount to ensure it’s a strategic investment, not just an added expense?”
• Technology and Automation: Probe their strategy for using technology and automation to drive efficiency. Are they exploring robotic process automation (RPA) for finance tasks or AI for demand forecasting? To discover more approaches, you can review some essential strategies for reducing operational costs on useshiny.com.

6. What are our growth investments and expected returns?

A company’s survival depends on its ability to grow, but growth requires capital. This question delves into the CFO’s role as a capital allocator, examining how they steward the company’s resources to fuel future expansion. It assesses their ability to identify, evaluate, and prioritize growth initiatives, whether through capital expenditures (CapEx), research and development (R&D), market expansion, or strategic acquisitions. A forward-thinking CFO will provide a clear narrative connecting investment decisions to the company’s overarching strategic goals and expected financial outcomes.

This is a vital question to ask the CFO because it reveals their approach to balancing short-term profitability with long-term value creation. For example, a CFO at a high-growth tech company like Tesla might justify massive investments in Gigafactories by presenting a detailed model showing how manufacturing scale will drive down unit costs and capture market share, leading to significant future returns. Similarly, a B2B SaaS company’s CFO might defend increased R&D spending by showcasing how new AI-driven features are projected to increase customer lifetime value and reduce churn, justifying the upfront cost.

Actionable Insights:

When discussing growth investments, probe for the underlying financial rigor and strategic alignment:

• Investment Criteria: Ask about the process for approving major investments. Is there an investment committee? What are the key metrics used, such as Internal Rate of Return (IRR), Net Present Value (NPV), or payback period?
• Performance Tracking: Inquire how the performance of past investments is tracked against their initial projections. A strong CFO will have a “post-mortem” process to analyze what went right or wrong, using those lessons to refine future decisions.
• Funding Strategy: Understand how these growth initiatives are funded. Are they financed through operating cash flow, debt, or equity? This reveals the CFO’s strategy for managing the company’s capital structure.
• Risk Assessment: How are the risks associated with new investments, such as market adoption or competitive reaction, modeled and mitigated? This links back to their overall risk management framework. For more on integrating these decisions, explore this comprehensive guide to strategic growth planning on useshiny.com.

7. How do you ensure financial controls and compliance?

A CFO’s responsibility extends far beyond financial strategy; they are the ultimate guardian of the company’s financial integrity. This question assesses their approach to establishing a robust financial governance framework, which includes internal controls, regulatory compliance, and audit processes. A strong CFO ensures that the company not only adheres to legal and regulatory standards but also operates with discipline to prevent fraud, errors, and financial misstatement. Their answer demonstrates a commitment to transparency and operational excellence.

This is a critical question to ask the CFO because a failure in controls can lead to catastrophic consequences, from financial losses to legal penalties and irreparable reputational damage. The infamous Enron scandal serves as a stark reminder of what happens when internal controls are weak or deliberately circumvented. Conversely, a CFO who can articulate a clear, multi-layered control environment, referencing frameworks like COSO, shows they are building the company on a solid foundation. For a global enterprise, this means managing a complex web of regulations, similar to how Johnson & Johnson maintains a global compliance framework across its many jurisdictions.

Actionable Insights:

When discussing controls and compliance, probe for specific evidence of their methodology:

• Recent Enhancements: Ask, “What recent improvements or investments have you made to our internal control environment?” This reveals if they are proactive or merely reactive.
• Audit Findings: Inquire about their process for handling audit findings. A competent CFO will have a structured remediation plan and view audits as a tool for continuous improvement, not an adversarial process.
• Managing Regulatory Change: How do they stay ahead of evolving regulations, like new tax laws or data privacy requirements? Look for a formal process for monitoring, assessing impact, and implementing necessary changes.
• Technology and Automation: Explore their use of technology. Are they leveraging software to automate controls, reduce manual errors, and improve monitoring? This indicates a modern, efficient approach to compliance.
• Employee Training: Ask about their role in employee training and awareness programs. Strong financial controls are only effective if the entire organization understands and adheres to them.

8. What is your outlook for the business and key assumptions?

A CFO’s role extends far beyond historical reporting; they must be a forward-looking strategist who can articulate a clear vision for the company’s financial future. This question tests their ability to synthesize market data, internal performance, and strategic initiatives into a coherent business outlook. It uncovers the core assumptions that form the bedrock of their financial models, budgets, and forecasts. A great CFO will not only present an outlook but will also transparently detail the assumptions driving it.

This is one of the most revealing questions to ask the CFO because it showcases their strategic alignment with the company’s long-term goals. For example, during its high-growth phase, Netflix’s CFO had to forecast subscriber growth based on key assumptions about international market penetration, content spending ROI, and competitive pressures. Similarly, a CFO at an energy company navigating the green transition must base their outlook on assumptions about regulatory changes, the cost curve of renewable technologies, and shifting consumer demand. Their answers demonstrate their grasp of both macro trends and micro-level business drivers.

Actionable Insights:

When discussing the business outlook, press for clarity on the underlying mechanics of their forecast:

• Key Assumptions and Sensitivities: Ask for a list of the top five assumptions underpinning the financial plan (e.g., customer acquisition cost, churn rate, average contract value). Inquire about sensitivity analysis: “How would a 15% increase in customer acquisition cost impact our runway?”
• Scenario Planning: Probe their approach to different future states. Do they have a best-case, base-case, and worst-case scenario? Understanding these scenarios shows how the finance team prepares for both opportunities and downturns.
• Forecast Accuracy: Inquire about their track record. How accurate have past forecasts been? Discuss their process for analyzing variances between forecasts and actual results to improve future predictions.
• External Factors: Explore how external variables like interest rate changes, competitor moves, or new regulations are incorporated into the model. This reveals their ability to connect the business to the broader economic environment.

8 Key CFO Questions Comparison

From Questions to Action: Driving Your Company Forward

The journey from a promising startup to a market leader is paved with difficult decisions and complex challenges. Engaging your Chief Financial Officer is not merely about reviewing past performance; it’s about co-authoring the future of your company. The strategic, operational, and financial questions we’ve explored are the essential tools for this collaboration. They transform the finance function from a static, historical record-keeper into a dynamic, forward-looking engine for growth and resilience.

By consistently asking about risk mitigation, cash runway, and key performance indicators, you establish a culture of proactive financial management. This isn’t just about avoiding pitfalls; it’s about building a fundamentally stronger, more agile business. A founder who understands their company’s financial heartbeat is better equipped to pivot, seize opportunities, and inspire confidence in investors, employees, and customers alike. These conversations build the alignment necessary to navigate uncertainty with precision and purpose.

Turning Dialogue into Strategic Advantage

The true power of these inquiries lies not in the asking, but in the action that follows. The answers you receive should directly inform your strategic planning, operational adjustments, and capital allocation decisions.

• Financial Risk Assessment: The answer to “What are our biggest financial risks?” should lead to a tangible action plan. This might involve diversifying revenue streams, renegotiating key supplier contracts, or purchasing specific insurance policies. It’s about building a fortress around your core business.
• Cash Flow Management: Understanding your cash runway isn’t a passive observation. It’s a call to action. If the runway is shorter than desired, the follow-up is immediate: Do we accelerate sales, cut non-essential spending, or initiate a fundraising round? Your CFO can model the impact of each lever.
• Performance Benchmarking: Knowing how your metrics stack up against industry benchmarks provides critical context. If your Customer Acquisition Cost (CAC) is higher than the industry average, the next step is to work with marketing and sales to diagnose inefficiencies and test new, more cost-effective channels.

The Fractional CFO: Your Strategic Partner in Growth

For many startups and scaling businesses in dynamic sectors like SaaS, FinTech, and HealthTech, the need for this high-caliber financial leadership is undeniable. However, the cost of a full-time, experienced CFO can be a significant barrier. This is where the modern approach to executive leadership provides a powerful solution. The right questions to ask the CFO are only valuable when you have an expert in the room to answer them with depth and foresight.

Platforms that connect you with vetted, part-time executives allow you to access the strategic mind of a top-tier CFO without the full-time financial commitment. This flexible model ensures you can have these critical conversations, develop sophisticated financial models, and implement robust controls on a schedule and budget that works for your stage of growth. By leveraging a fractional CFO, you are not just filling a role; you are injecting elite, actionable intelligence directly into your leadership team, turning crucial questions into your company’s competitive edge.

Ready to have these critical financial conversations with an expert who can provide the answers and guide your strategy? Shiny connects you with a network of world-class, vetted fractional CFOs to help you scale smarter and faster. Find your strategic financial partner today and turn insight into impact.