5 Commonly Asked Questions from CEOs for CFOs – and How to Answer Them

by Marc Linden

There’s an opportunity in every conversation with your CEO to move past being your company’s “numbers guy.”

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We’ve all been there. Conversations with CEOs about the business’s financial state of the union can lead to sweaty palms – especially when the news to share isn’t ideal. We’ve all practiced our explanation of the difficult data points ahead of time, repeatedly run through graphs and charts to ensure accuracy, and let ourselves get carried away with the “what ifs.” 

In my 20+ years of finance, I’ve experienced my share of tough meetings, and I also hear regularly from other financial executives on their own experiences. Regardless of industry, there’s a very clear set of questions CEOs tend to ask their CFOs. 

These are the five I hear come up – and a few thoughts on how to prepare for them. While these are hardly actual sound bites to memorize, approaching your answers in this way will encourage the CEO to recognize your impact not just as the “numbers guy” but instead as a key strategic player for the company’s long-term goals: 

  1. Where are we on hitting company long-range goals?               

The good news is that long-range goals have more than likely been set in collaboration with the CEO in the first place. Because you serve as the backbone of the financial team, the CEO isn’t just asking you where the company is in relation to set goals, but instead, how the company got where they are, what comes next, and what changes need to be made. Provided you are up to date in regards to goal status (rather than checking in only when required), this question provides a venue to share strategic forward thinking and perspective. 

That said, for this conversation to be productive, accurate financial reporting and up-to-date data is essential. If you can’t come equipped with this data, it’s time to upgrade to a more efficient, comprehensive financial management system. It’s no secret that financial change happens quickly in any business, and it’s up to you as CFO to know why these changes are happening. Goal tracking is a huge part of the CFO’s job, but analysis of movement on said goals is what drives a business forward, and what elevates your role within the leadership team. This question will likely serve as the foundation for your conversation, so coming in with a full-picture, accurate answer here can set a positive tone for the rest of your discussion. 

  1. What are the investment opportunities you’re considering and how do they compare?

When a CEO asks about investment opportunities, they are asking on behalf of themselves, but also on behalf of the board and shareholders.

Andrew Pease, CFO of dental benefits company Brighter, says that when he is speaking to his CEO, he prioritizes determining and sharing the company’s product roadmap from a strategic perspective. He notes that having a strong ROI matrix detailing the end result can be an extraordinarily helpful resource when communicating around various investment opportunities. It’s true – planning investments requires a close look at long-term goals and financial priorities. 

You have insight into why the office in Portland isn’t financially sustainable, why variable costs have increased in a certain aspect of your business (and how to cut them), so speak up! This is an opportunity to tell your CEO where you should be investing, and why, where you should open (or close) an office, and why. Forward-thinking ROI analysis is what sets you apart as a CFO, and can elevate you as a decision-maker. 

  1. Where are we on cash and sources of funds?

It’s no secret that cash flow analysis and prediction are two of the most important parts of a CFO’s role, at any company, in any industry. According to Brian Singleton, CFO of Fitness Formula Clubs, this question is the one he is most frequently asked, likely because, similar to the question regarding long-range goals, a cash and fund update can serve as an overarching company financial state of the union, if the question is anticipated and adequately prepared for. 

When your CEO asks you about cash and sources of funds, he or she is asking you to share a sense of company spending and to make projections about the both near and long term. Knowing where the company’s cash is and analyzing both best and worst case scenarios is essential in painting an accurate financial picture of the company. 

There will inevitably be a time when the answer to this question is not a positive one. Sharing difficult news is one of the least fun parts of a CFO’s job, but maintaining a transparent and honest CEO/CFO relationship can help. Most importantly, bad news always needs to come with a data-driven and supported plan to improve the situation. 

  1. How should we measure results impacting the business?

CEOs, stakeholders, and board members often measure non-financial (but still quantifiable) aspects of the company when measuring financial results. So when CFOs get asked this question, they need to strike a balance between sharing financial and non-financial information. This may be unnatural for CFOs (at least at first), but is essential when speaking with a target audience including those without a strong financial background. Andrew Pease notes that sharing financial and non-financial data together is the best way to give a complete picture of how results are impacting business, stating that agreeing on key success metrics, and most importantly, sticking to those metrics, can make all the difference. 

Agreeing on how to measure results sets the financial team up for success. Setting distinct metrics enables strategic, data-driven decision making in real-time, with the appropriate accurate financial data. CFOs need a robust, cohesive financial reporting platform in order to maintain a data set that encourages forward-thinking decision-making. 

  1. In terms of business risk, what questions do we not have answers for?

Business is unpredictable – competitors enter and exit the market, markets change – and we need to be prepared for all of the unknown.  

So, come prepared. For example, knowing your competitors’ growth statistics, their flexibility, their news, their pitfalls, can help you determine their strength in the market, and allow you a more complete into how the market is functioning. Coming into this conversation equipped with a business risk and recovery plan, as well as likelihood statistics and remediation options that account for things like unexpected economic downturns, will allow you a head-start on this question. 

There is an inherent opportunity in every conversation with your CEO to move past being your company’s “numbers guy.” Beyond running your department on a modern, cloud-based system that arm you with real-time, accurate financial data, using every single touchpoint to your advantage enables you as CFO to build a role for yourself as an insightful analyst for the business in the eyes of the rest of the executive team. 

As CFO, we always want to be sharing good news, but the truth of the matter is that sometimes, conversations with your CEO can be daunting. Hopefully these tips will make your next sit-down with your CEO go a little more smoothly, and remove sweaty palms from the equation. 


Marc Linden is Senior VP, Head of Business Operations and Finance at Sage Intacct.