20 Questions

Questions to Ask a CFO of a Large Company

Engage with senior financial leadership using these strategic questions that demonstrate your business acumen, financial understanding, and interest in organizational success.

1

What's the biggest financial challenge the company is facing right now?

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Why this works

Shows strategic thinking and helps you understand current financial priorities while demonstrating your interest in organizational success.

2

How do you approach capital allocation and investment decisions?

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Why this works

Reveals their strategic approach to financial decision-making and helps you understand their investment philosophy and risk management.

3

What's your approach to managing financial risk?

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Why this works

Shows their risk management strategy and helps you understand how they protect the company's financial health and stability.

4

How do you ensure financial transparency and accountability?

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Why this works

Reveals their approach to financial governance and helps you understand their commitment to ethical financial practices.

5

What's the most important financial metric you track?

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Why this works

Identifies their key performance indicators and helps you understand what they consider most crucial for financial success.

6

How do you approach budgeting and financial planning?

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Why this works

Shows their strategic planning process and helps you understand how they align financial resources with business objectives.

7

What's your approach to managing cash flow and liquidity?

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Why this works

Reveals their working capital management strategy and helps you understand how they ensure financial stability and growth.

8

How do you evaluate and manage financial performance?

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Why this works

Shows their performance measurement approach and helps you understand how they track and improve financial results.

9

What's your strategy for managing debt and financing?

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Why this works

Reveals their capital structure approach and helps you understand how they optimize the company's financial leverage.

10

How do you approach financial forecasting and scenario planning?

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Why this works

Shows their forward-looking approach and helps you understand how they prepare for future financial challenges and opportunities.

11

What's your approach to managing financial relationships with stakeholders?

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Why this works

Reveals their stakeholder management strategy and helps you understand how they communicate financial performance and strategy.

12

How do you ensure compliance with financial regulations and standards?

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Why this works

Shows their regulatory approach and helps you understand how they maintain financial integrity and legal compliance.

13

What's your strategy for managing financial technology and systems?

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Why this works

Reveals their technology approach and helps you understand how they leverage financial systems for efficiency and accuracy.

14

How do you approach financial talent development and succession planning?

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Why this works

Shows their people strategy and helps you understand how they build and develop financial leadership capabilities.

15

What's your approach to managing financial partnerships and alliances?

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Why this works

Reveals their partnership strategy and helps you understand how they leverage external relationships for financial success.

16

How do you approach financial innovation and digital transformation?

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Why this works

Shows their innovation strategy and helps you understand how they adapt to technological changes in finance.

17

What's your strategy for managing financial sustainability and ESG?

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Why this works

Reveals their sustainability approach and helps you understand how they integrate environmental and social factors into financial decisions.

18

How do you approach financial crisis management and contingency planning?

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Why this works

Shows their crisis preparedness and helps you understand how they handle financial emergencies and disruptions.

19

What's your vision for the future of finance in the company?

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Why this works

Reveals their long-term strategic thinking and helps you understand where they see the finance function heading.

20

How do you measure the success of your financial leadership?

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Why this works

Shows their self-assessment approach and helps you understand how they evaluate their own performance and impact.

Best Practices for CFO Conversations

Expert tips and techniques for getting the most out of these questions.

Best Practices

Show Financial Acumen

Demonstrate your understanding of financial concepts and business metrics. CFOs value professionals who can speak their language and understand financial implications.

Focus on Strategic Impact

Ask questions that show you understand how finance drives business strategy and growth, not just operational details.

Respect Their Time

Be concise and focused. CFOs have limited time, so make every question count and avoid wasting their time with obvious or trivial questions.

Question Sequences

The Strategic Financial Sequence

1
What's the biggest financial challenge the company is facing right now?
2
How do you approach capital allocation and investment decisions?
3
What's your approach to managing financial risk?

The Performance and Governance Sequence

1
What's the most important financial metric you track?
2
How do you ensure financial transparency and accountability?
3
How do you approach financial forecasting and scenario planning?

Common Pitfalls

Don't Ask About Basic Financial Concepts

Avoid questions about fundamental financial principles that you should already know. Focus on their specific approach and strategy instead.

Don't Focus Only on Numbers

While financial metrics are important, also show interest in strategy, leadership, and the broader business impact of financial decisions.

Don't Make It About Your Personal Finances

Focus on the company's financial strategy and challenges rather than your personal financial situation or career advancement.

Conversation Templates

The Strategic Financial Deep Dive

1
Step 1: Start with: "What's the biggest financial challenge the company is facing right now?"
2
Step 2: Explore with: "How do you approach capital allocation and investment decisions?"
3
Step 3: Conclude with: "What's your vision for the future of finance in the company?"

The Performance and Risk Focus

1
Step 1: Begin with: "What's the most important financial metric you track?"
2
Step 2: Follow with: "What's your approach to managing financial risk?"
3
Step 3: Deepen with: "How do you approach financial forecasting and scenario planning?"

Further Reading

"The CFO's Guide to Strategic Finance" by Jack Alexander
"Financial Intelligence" by Karen Berman
"The Lean CFO" by Nick Katko

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