Most CFOs I know didn't get into finance to chase receipts.

But that's where the time goes. Reviewing expenses that should have been blocked before they happened. Closing books that take longer to close than the month took to live. Approving spend that should have been approved automatically three days ago.

That's not a people problem. That's a systems problem.

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I want to propose a scenario for you. We're back to January 2007. You are the CFO of the most successful software company in the world. Your CEO just went on camera and publicly dismissed a competitor's new product. He called it overpriced. He said it had no keyboard. He said it would never get significant market share.

However, your data is telling you a different story. Mobile adoption is accelerating. Your competitor's hardware margins are strong. Consumer electronics is moving fast. Do you go into his office?

That CEO was Steve Ballmer. The company was Microsoft.

The product he was referring to was the iPhone, and within five years it was the most profitable consumer product ever made. Microsoft's mobile business was essentially over. They eventually wrote off $7.6 billion on their Nokia acquisition and exited the market entirely.

In many ways, I think the CFO is looked at as the consigliere of the CEO, their truth teller.

On one hand, you do, to a certain extent, get a pass to call their baby ugly (not their actual kid, but their product) if you MUST, because you're making the resource allocations attached to it. Yes, you report to the CEO, but you also have a fiduciary responsibility to shareholders and you don’t want to throw good money after bad (like, idk, buying Nokia in the first place).

I've definitely been in scenarios where I've spoken up and been very happy I did. And a couple of moments come to mind where I said to the CEO, "I think that was a bad choice." And then it's pretty awkward after.

So when, as a CFO, should you speak up to a demanding founder? And what’s the cost of doing so?

We recently explored this question on the RTN podcast, and reflected on advice that top investors and CFOs have given me on the topic over the years.

Apple | Spotify | YouTube

I did an interview with Alex Immerman, general partner at a16z, in June of 2025, and he was talking about his favorite interview question for a CFO candidate.

The CFO is supposed to have the company's best interests in mind, not their department's. And at times you not only have to tell the CEO something that they don't want to hear, but also your peers throughout the C suite who are philosophically aligned with the CEO.

A bad answer to Alex’s question would be something general around budgeting: “The CEO wanted to go spend on a big conference and I said that doesn't sound like money well spent.” That's lame. You should just be able to tell them there's no ROI. The complicated ones are hiring decisions, or launching a product in a new country, or maybe even an acquisition.

What makes it harder to push back is that founder CEOs only got to their position because they've said damn the torpedoes so many times over, and taken these crazy risks that nobody else believed in. So in many ways they're probably looking at you, as the CFO like, “well, I've outperformed what the market said I couldn’t do 10 times in a row. And you're going to tell me that this isn't going to work? No, no, no. You don't get how I got here.”

That's the part that often goes unsaid: you’re arguing against house money. And it's hard to be the counterweight to a person who created something incredible when the odds were not in their favor.

Which is why you need to check your ego.

Curt Sigfstead, the CFO of Clio, said this back in December of 2024 when I asked him about working with founders.

Putting your ego in the bottom drawer is really hard to do. When you're around CEOs with a sphere of influence, an energy that's dynamic and contagious, it's easy to forget that you are merely part of the supporting cast to execute on that vision.

Founders are visionary in the sense of knowing where they want to push the company, where they want to go, and what they want the angle to be. What they may lack, and where a CFO can help a lot, are the intermediary steps to do it. They understand that they want to be number one in the market with this many products by this date. So how do you bridge the gap in between? That’s where CFOs get tactical.

Steve Jobs almost never asked customers what they wanted. Same with Henry Ford, who said people would have just asked for faster horses. So a lot of times, instead of saying no to a founder, it's pivoting by using questions to better understand what the motivations are and where they're trying to go. In the end, maybe that means you have to create a car instead of using a horse to ride to their destination.

Curt's warning is that if you come in and say “Look, you got 10 problems, buddy,” 99% of founders will just shut down.

Before you push back, you have to seek to understand. It’s the first principles version of “why are they trying to do this thing at all.”

Plus, you gain trust by showing somebody you have a real interest in their thinking. That is how you earn trust… through curiosity.

David Lapter is the CFO of Dashlane, and by my count something like a five time CFO. He's going to be in the baseball hall of fame for CFOs someday. I asked him about speaking up as a CFO.

For context, fab.com was one of the highest funded marketplaces for buying goods around that era, and like a lot of its contemporaries, it did not have the best ending. They were burning an insane amount of money to keep the company going relative to the revenue it was bringing in. David is reflecting on the decisions they made around hiring velocity and the product roadmap.

I've always spoken up about the hiring stuff. But if you're working with a technical leader, it can be daunting to question their decisions around the roadmap, because you're not technical. David's approach is to bring data to a conversation that may be outside the purview of a CEO, to arm people with the correct information to make those decisions, even if you're not the one ultimately deciding.

Speaking up doesn't always mean speaking up to say you disagree. Sometimes speaking up is providing the context and the numbers that better serve the leaders around you.

Building a culture where "I think we are off" is welcomed instead of punished comes down to having forums to share data and information. Because nobody likes having it thrown on their desk after the fact that this is wrong, this is bad, you made a terrible choice. If you’re creating space for conversations, it should never come to that cinematic point. It should be a series of discussions around data in the context of your market and your competitors, and then the macro of where you can deploy capital. Maybe that's a Monday exec meeting. Maybe it's five key data points that everybody agrees are the most important to operate the business, sent out every Tuesday at the same time and accessible to everyone. As a CFO part of your job is not only speaking up, but creating an environment for context to be shared.

Ballmer just went on camera and laughed at the iPhone. You've got the relationship, you've earned the trust, and your ego is in the bottom drawer. What do you walk into his office and say?

To be honest, it’s less an indictment on that moment in time and what was said, and more a reflection on the culture that was created to live in that warped view of what good performance looks like.

There's an obvious tension here. Alex wants chutzpah and Curt wants your ego in a drawer.

What Curt is describing is the positive framing, where the CEO wants to drive the business to a good outcome and your job is helping them get there. So pant the road. Embrace the servant leadership.

But you also need the backbone when you're faced with a one way door decision, just as David coached.

Both are required qualities of a CFO under different circumstances. And both call for a specific version of speaking up.

Hoping you don’t forget to speak up when your CEO decides to publicly insult the iphone,

CJ