


How CFOs (and finance leaders) should disagree with demanding CEOs/founders—when to push back, how to earn the right to do so, and how to avoid silence, ego, or “all-green” dashboards.
CJ and Ben discuss with multiple CFO guests/clips: Alex Ammerman (A16Z GP; interview question for CFO candidates); Kurt (Clio CFO, Dec 2024); Daniel Kang (Mercury CFO, Dec 2024); Adam Ante (Paycor CFO, Jun 2024); David Lapter (Dashlane CFO); plus references to Steve Ballmer/Microsoft and Steve Jobs/Disney/ESPN.
CFOs are “truth tellers”/counterweights (triangle of doom: CEO+board+CEO’s incentives vs CFO fiduciary duty). Disagree with data, not ego; seek to understand first; build trust; speak up early with context; avoid being a pushover or a know-it-all; don’t rely on “purse strings” as leverage.
Microsoft dismissing iPhone in Jan 2007 (Ballmer vs market data); Nokia write-down; Disney dreamer/executor dynamic (Walt/Roy); Fab.com speaking up on hiring/product roadmap; ESPN phone; conference spend budgeting red flags; international expansion/acquisitions as harder disagreement scenarios.
Written by AI. May contain mistakes.
Exploring advice on dealing with a challenging founder through a historical example.
“You are the CFO of the most successful software company in the world.”
Discussing the power dynamics between the CFO, CEO, and board of directors.
“They eventually wrote off, I think,$7.6 billion on their Nokia acquisition and exited the market entirely.”
The importance of the CFO speaking the truth and providing candid feedback.
“What I'm trying to glean is whether the candidate is a pushover and the CEO hopefully does not want to bring on a pushover.”
Insights on what makes a strong CFO, including the ability to disagree with the CEO.
“or you potentially being purchased by another company.”
Strategies for CFOs to effectively collaborate and empower founders.
“And I've come to appreciate the ability of a CFO to be disagreeable more and more as I've talked to an increasing number of podcast guests.”
Strategies for CFOs to effectively collaborate and empower founders.
“Here's a growth tax that nobody talks about.”
Learn how to effectively interact with demanding founders while maintaining your professional integrity.
“Like we said before, founders are visionary in the sense of knowing where they want to push the company and where they want to go and what they want the angle to be.”
Understand how finance professionals can add value and navigate their career paths effectively.
“Now he's the SVP and managing director at Paychex.”
Learn how effective listening can change perceptions and improve leadership dynamics.
“You're just reflecting back what you're hearing.”
Discover the significance of speaking up against poor decisions and the lessons learned from Fab.com's experience.
“Like, that's something that stays with me.”
Understand how to foster an environment that encourages open dialogue and data sharing.
“Like many other companies, did not have the best ending.”
Learn how to earn trust through a growth mindset and genuine interest in others' perspectives.
“It should be a series of conversations around data and the context in your market scenario, especially as it relates to your competitors, and then the macro of where you can receive funding.”
Explore strategies for addressing uncomfortable truths without damaging professional relationships.
“But they continue to do so because the metric was invented by somebody a while ago and they did things a certain way.”
Delve into the implications of missed opportunities and the importance of candid discussions in leadership.
“As a CFO, not great if you jump down their throat and just yell at them.”

Get the gist, explore an idea or ask about something said.
On Run the Numbers, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00CJ, you have no freaking clue what we're talking about, huh? I don't know what we're doing, Ben. I don't know why you've called me into your office here. I feel like I'm going to get fired or it's like bring your CFO to work day. No, you actually asked me what sort of advice have we talked about if you're working with like maybe a difficult founder or difficult CFO. Yeah. 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.
0:33He said it had no keyboard. He said it would never get significant market share. 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? I have a hunch of what company it is because the CEO is larger than life, if I'm guessing who this company is correctly. This guy might have some current aspirations of something bigger right now for your basketball fans. This is a common thing with executive presence. It's called the triangle of doom, right? If you're the CFO, you actually have the weakest spot on the triangle.
1:12This is something that Rick Smith, former guest, taught me. And the other two points of the triangle are the CEO and the board. And the board and CEO have conversations all the time that you're not privy to. You kind of have two bosses in a way, right? The CEO is your boss on paper, but you have a fiduciary duty to your shareholders and to your board. And you also don't want to go above either one and offend them. So whenever there's a scenario like this, I try to say, is there something I don't know? And are there other incentives from others involved? That CEO was Steve Ballmer. The company was Microsoft.
1:45That is the most expensive phone in the world. And it doesn't appeal to business customers because it doesn't have a keyboard, which makes it not a very good email machine. The product 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, I think,$7.6 billion on their Nokia acquisition and exited the market entirely. I forgot that Microsoft tried to launch a phone. Complete tangent. Do you remember when ESPN launched a phone? ESPN launched a phone? I don't know if it's any text, but you could check the scores of sports games.
2:18So it's a crappier version of the ESPN app. And I think the phone only lasted like six months. $300 for the phone itself and between$65 and$225 per month for content. Steve Jobs called it the dumbest fucking idea I've ever heard. But back to your question, I've actually been in the room more often where I've said something and maybe even regretted it because I felt like I couldn't keep it inside of me. I just had to call a spade a spade. And in many ways, I think the CFO is looked at as the consigliere of the CEO. It's their truth teller. You do, I think, get a pass to call a baby ugly or product ugly if you have to, because you're making the resource allocations that are attached to it.
2:59I've definitely been in scenarios where I've spoken up and been very happy I did. And a couple scenarios come to mind around, I think, hiring decisions, where I said to the CEO, I think that was a dumb choice. And then it's pretty awkward after. Is this thing on? Yesterday's price is not today's price.
3:26You did this interview with Alex Ammerman, who is the general partner at A16Z. This is in June of 2025. And he was talking about his favorite interview question for a CFO candidate. So let's roll the clip.
3:40Alex Immerman: My personal favorite is tell me about a time you disagreed strongly with the CEO and what happened. So a great CFO is not just a numbers person, but a strategic counterweight. We were talking about the strategic mind earlier. And this question is important for assessing that. one do you have a backbone do you have the chutzpah to to stand up in a difficult situation by the way if your example is not a difficult situation you probably don't have a backbone do you have the communication skills to thoughtfully disagree do you have the respect and trust of the CEO. What I'm trying to glean is whether the candidate is a pushover and the CEO hopefully does not want to bring on a pushover.
4:36Alex Immerman: I disagree with my haircut at the time. I was going to say, I'm glad you switched barbers. I'm glad you said that first. I remember this discussion with Alex because he validated a lot of the thinking that I had around the CFO's role, not just as a fiduciary, but as the person who can call strike a strike and call a ball a ball and be honest with everybody there. And the CFO is supposed to have the company's best interests in mind, not their departments. And at times you not only have to tell the CEO something that they don't want to hear, but your peers throughout the C-suite. So this is one of my favorite conversations, I think, just on the dynamics between the CEO and CFO.
5:15So this interview question, Tell me about a time that you disagreed strongly with the CEO and what happened. Is there a version of that answer that may sound good in an interview, but it's actually a red flag? Yeah, I think it would just be around something weak around budgeting. Like the CEO wanted to go and spend on a big conference. And I said, that doesn't sound like money well spent. OK, that's table stakes. You should just be able to tell them like there's no ROI on that. The more complicated things are, like I said, around hiring decisions in the C-suite. It's around launching a go-to-market product in a new country and having to really expand your workforce there.
5:53It could be around an acquisition. I think a lot of these questions often come up around something new coming to the market or you potentially being purchased by another company. CEOs only got into that position, especially founder CEOs, because they've said, damn the torpedo so many times and taken these crazy risks that nobody else believed in. So in many ways, they're probably looking at you as a CFO like I've outperformed what the market said I could 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 something that I think is unsaid that that is hard as the CFO to hold them back and be that counterweight when this person has done something, created something so incredible when the odds many times were not in their favor.
6:36One of my favorite examples of just that like sort of dreamer and like realist dynamic is the Disney company history and how when they first started out, Walt was the dreamer. He was the guy that was like had all the ideas. His brother, Roy, I guess he was like sort of the COO. I don't think Roy gets enough credit for executing on Walt's vision in the sense that a CFO or COO many times has to continue to lay track out in front of the CEO, which can be hard, right? Because you have to find a way to coordinate resources to execute on that vision. There's a documentary that's about that Disney renaissance in like the 80s.
7:12You know, they were almost taken over in like a hostile takeover type thing. And it was like when Michael Eisner and Frank Wells came in. Michael Eisner was the sort of new Disney type like kind of dreamer, but he had Frank Wells. And it was when Frank Wells tragically passed away that like things kind of went off the rails a little bit. That steady hand, really. Yeah. You had sort of a response to this. I don't remember my response. I want to see what you what you say here. I think in a lot of ways, the best CFOs are liked even when they make non likable decisions. And what I'm trying to say, I think is like, you're often put in these positions that are inherently disagreeable.
7:46But if you have the trust of your peers to make that call, and they're like, I didn't like the outcome of that decision or exactly like where your mind was that like with going international, but like I respect where you're coming from. And I appreciate you pushing back like that means a lot. You still feel the same exact way. Is it worth even going deep on that? Yes. And I've come to appreciate the ability of a CFO to be disagreeable more and more as I've talked to an increasing number of podcast guests. It's against your human nature to not have people like you. Like we started off in tribes, right?
8:20Where if you weren't liked, you get pushed out and you probably die. get put in these positions where you have to fight against that human nature to be liked by others around you and the ability to just lock in and give the right answer for the company at the time maybe not for the people around you in terms of how they see the business and world in that moment makes you such a better exec and I really respect it. Hey thanks for listening we'll be right back after a word from our sponsors.
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11:15CJ Gustafson: All in one place with support from real experts when you need it. So if you're raising, hiring, or scaling, Pulley keeps your cap table clean so you can stay focused on building. Not wrangling spreadsheets. Learn more, request a demo at pulley.com slash mostlymetrics. That is P-U-L-L-E-Y dot com slash mostlymetrics. So this next clip is actually from Kurt from Clio. He's still the CFO of Clio. This clip was from December of 2024. He talks a little bit about maybe not the complete flip side of what we've been talking about here, but he says something here that I think you'll really appreciate. I want to let him say it.
11:52I don't want to spoil it for you. Are there any strategies for working with founders and empowering them from the CFO seat? Yeah, there's a couple. One is take your ego and put it in the bottom drawer and shut it hard. and really listen and build trust. I found that founders are an incredible source of information and they have very compelling perspectives on business decision-making, whether it's compensation to new products, but you got to find a way to get it out. And you've got to ask the right set of questions. And it's got to be Q &A-based and conversation-based because the best way I found is founders have almost an allergic reaction to the answer no.
12:42Like, so, you know, take a conversation. You're saying like, no, you shouldn't do it that way, like as a CFO. Okay. Well, that just set off an alarm bell and that ends up, you know, creating all kinds of friction as you continue to go through the conversation with the founder, as opposed to help me understand, help me understand, let's get to the bottom. What are you really trying to do? What are you trying to do? Have you thought about maybe approaching it from this perspective because it would, you know, add this, this, and this, or is that an issue? You do have to really think about how you're going to approach these issues because the founder has to see you as an ally and has to trust you implicitly.
13:23And three is you're not in this role, especially with founders, to take the limelight. You're here to propel. I mean, I talk about it as at-service leadership. You're at the service of the founder. You're at the service of the executive. The finance leader is to elevate everybody in the company to make better decisions, to achieve what they need to with the resources that we have, and similarly with the board. And so you've got to kind of have that mindset with founders. And I can tell you, just avoid a lot of challenges if you adopt that. Take that ego, CJ. Put it in the bottom drawer. What do you think?
14:02It's really hard to do, especially when you're around CEOs with this sphere of influence and the energy that's dynamic and contagious to always remember that you're just part of the supporting cast to execute on that vision. Like we said before, founders are visionary in the sense of knowing where they want to push the company and 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 is 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, but how do you bridge the gap in between?
14:39The CFOs can be tactical in helping to get there. I think Steve Jobs almost never asked people or customers what they wanted in a lot of ways. And the same thing with Henry Ford. He said people would have just asked for faster horses. And so a lot of times, instead of saying no to a founder, it's re-pivoting by way of using questions to better understand what the motivations are and where they're trying to go. In the end, maybe that is you have to create a car instead of using a horse to ride to their destination. It seems like there's an inherent tension in this advice because earlier we were talking about have some chutzpah, have some backbone.
15:16But now Kurt is talking about taking a back seat, keeping that ego in the bottom drawer. I think you have to have that backbone when you're faced with a one-way door decision versus a two-way door decision, right? You have to stand up and let your opinion be heard and say, I think that's a good idea or a bad idea. But what I think he's saying here is more in the positive framing of the CEO wants to drive the business to a positive business outcome. How do you help get there? Put your ego away. You are the Robin to the Batman. man, how do you help execute upon that? So I think they're both true under different circumstances.
15:50Is it a matter of like uncovering that second door? This is going to come across like a generalization. It's definitely not true in every scenario. I find a lot of CEOs think in terms of binaries of like, we're going to do this and get to this point. And it's like black and white in terms of like where they want to go with things. There are often shades of gray that get uncovered along the way, or there are different paths you can take to achieve similar outcomes. So to your point, Ben, I think it is finding those different variations by way of asking questions of what we're trying to achieve.
16:23So next, I want to pivot to a clip where you're talking to Daniel Kang. And at the time, it was December of 2024. He was the VP of Finance at Mercury. Now he's the CFO of Mercury. So definitely some valuable information for folks that maybe aren't in the C-suite yet. This is coming from a guy that said this at the time and he finds himself in the CFO seat now. I do think that finance has a bigger voice sometimes in other groups though. And this is, you know, just it happens that way. I'm not saying it's fair, but because you're helping the CEO a lot of times with that initial tops down cut, or you're doing the long range plan, you can have your fingerprints on the org.
17:01Now, I'm not saying that like it should be viewed as a financial exercise per se, but you do have a, like you You said a voice at the table of shaping it. The way that finance can best plug in, I actually don't like this moniker of finance has to sit at the table because you control the purse strings. I think that's actually like the last type of hard power that you want to exercise to be effective in your job. You want to be effective in your job because you're being a thought partner and like being able to hopefully allocate resources in partnership, assuming that everyone has the right intentions behind and thinking about the company and not like their own individual kingdom building, which does happen, obviously.
17:36That's so well said. Like if people are only listening to you because you can say yes or no because you have money, it's like, do they really respect you? For sure, for sure. I say that like I know that I'm being a good partner when like my CMO or CRO will come to me with like an idea that's not fully baked yet, right? But they want to bounce it off me and it's not because, it means I've broken through them thinking that I'm there just to like judge something as like a binary investment decision. like they see me as a thought partner. Like, oh, I can bring them like this half-baked idea and we can jam on this to see if it has legs.
18:11I think the best marker of a successful finance team is when you do see those type of cross-functional pools for collaboration. I think that's a much better marker than like forecast accuracy or some of the silly things that finance teams try to set. Okay, Arlen. Ben, these clips are such a throwback. Have you realized the background behind me has changed three times from the same seat in the same room? I know. Let this be proof that you're not actually an AI guy. You just got a little bit more budget. So don't use the purse strings as your seat at the table, I think, is the summary of what Daniel's talking about there.
18:45I've also heard the opposite take here, too. It was from Sonowi Torero, CFO and COO now of Envoy. He basically said, it's funny, finance has this power to also make certain problems go away with money. And he wasn't saying bribe people. He was saying money sometimes can cause problems and you can use that with discretion. Let's say you have someone who gets paid$200 ,000 a year and they're being blocked from 50 % of the productivity because of a$10 ,000 problem. Use your magic wand and make that go away with$10 ,000 worth of spend. However, to Daniel Kang's point, that shouldn't be the only reason they're coming to you for the money.
19:22They should be coming to you for helping to think through whatever issue it is that they have. And money is one of the arrows you have. It's not the end-all, be-all. They should be coming to you because they think of you as someone who can clearly think through a scenario that involves resource allocation. It involves pricing, involves whatever it may be. And they trust your opinion on it. When I say trust your opinion, it means they're coming to you because they don't think they're going to be judged. Right. Because the CFO does sit in this funny seat where they could go to the CEO and say, like, hey, I don't think CMO is pulling their weight or doing a great job based on the numbers I have.
19:57They also think that you're going to jam out with them and give more back than what they gave to you in terms of, hey, can you think through this? It seems like there's rarely a scenario where you're going to be like, sorry, man, just don't have it in the budget. The bad CFOs and bad finance professionals will just stop at, no, can't do it, red light. We don't have money in the budget. There's always conversation that should be had around what is the best risk adjuster return on the capital we have. And also it goes back to what we were saying with the CEO before. What are we even trying to achieve with this?
20:29Because it may not even be that we don't have the money. It just may be we don't have the right people working on the right stuff. And it's changing the mix of people and software and now tokens. Hey, thanks for listening. We'll be right back after a word from our sponsors.
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24:01Now he's the SVP and managing director at Paychex. Paycor was acquired in April of 2025. So a little bit of growth for him. I know you've gone through going public and you've gone through a company being acquired as well, correct? I have not gone through the process of going public. We thought we were going public just like every other company during the Zerp era, but I've gone through the process of being acquired. And if you're acquired, the CFO and the chief legal officer and usually the head of HR are the first three at the door. If you're acquired and you are the CFO of a company and you go to that next company, you're probably not going to get that same title.
24:35Maybe even like it may appear on paper like a demotion of sorts, right? Well, usually they don't keep you around because they already have a CFO. And ostensibly, it's a bigger company if they're acquiring you. There are a couple scenarios, I think, where like the minnow swallows the whale. One example that I can think of is Matt Hudson. Coda was acquired by Grammarly, a much bigger company. And the CEO of Coda became the CEO of Grammarly. which was neat to see. Let's let Adam rip here. Adam, do you think finance people pigeonhole themselves into narrow roles? Are there examples of like jumping into places that you didn't belong in your career that actually paid off?
25:15I think finance people do that in spades. They're so good at it. Finance people, accounting people, people with that background. I don't know if it's because it's just where they're comfortable is, you know, staying in numbers and staying in the financials, or if they don't realize the opportunity that they have to really take things to the next level. But I do see, you know, folks sort of shrink away from the opportunity to like really press into the business and show open places that, yeah, maybe they don't have any right to be, but there's an opportunity. And I think it's cool, like folks always want a seat at the table.
25:51And when I hear people say like, I want a seat at the table or they're not giving me the seat at the table, I think you have to like look at yourself and say like, well, first, are you adding value to these conversations? Because when you're adding value and you're killing the things that you're doing, people want you to be sitting at their table. And then when you get to the table, then you're like, I have the right to sort of get into anything I want. And you've got to be respectful, of course. You don't want to just like, you know, you're a finance person, by the way. You haven't sold software yet.
26:18But, you know, when you can step into some of those areas, you can add a different perspective. And I think that's what's really valuable is when you can come with a different perspective, then everybody can make better decisions. And I've been sort of lucky enough to get into those opportunities, you know, quite a few times in my career. I feel like there's something that's like uncomfortably honest about this take that is they're not giving me a seat at the table almost always this self-diagnosis. Does it come from like reflection inwards? Something super empowering that Shruti Lanka, CFO of Publix, told me is that the CFO has the right to sit in on any meeting within the company, right?
26:53It's all within your purview. Do not feel restricted. You do not have the right to speak up and give advice on stuff you don't know, but you do have a right to be at the table and be at least a listener to the conversation for your awareness. Made me feel pretty good around not pigeonholing myself. And what Adam gets at here is you earn your way into conversations outside of the typical finance realm by proving value, right? And it also links to what Dan Kang said around being a good business partner. Thinking more broadly about the departmental specific problems that someone's trying to solve and using whatever in your arsenal to help them achieve that.
27:30You've started a company. It's your first 90 days at the company. What is adding that value actually look like in, let's say, the first 90 days when you may not have earned that trust yet? It's coming in with a fresh set of ears and eyes to an org that has been doing stuff in a certain way because inertia is hard to move. hey how are we paying sales reps here walk me through it and then you're looking around like well that well why do we do it that way oh because so-and-so used to work here and we did that and so much of it is just listening then reflecting back what you heard it's funny even sometimes you say something to a sales leader a cmo you're just stating what your observations are because those are usually your closest stop partners right as a cfo outside of the ceo they're like oh and just hearing that can can make them think about it differently you're not even giving suggestions right?
28:16You're just reflecting back what you're hearing. And so I think there's a lot of value, not just for CFOs, but anybody coming into an org in terms of absorbing what's going on and then trying to figure out why things are done a certain way. Then I think you can start to make suggestions on how you might change things. Is there a version of this where like the CFO is genuinely being excluded and it's just not their fault? It's cultural at that point. I think it's because it's not a data-driven organization or they think that the CFO is reactive and just in this back room, they're going to write down what the results were after the fact, right?
28:46So next up, we have a clip from David Lapter. He's the CFO of Dashlane. I believe he's like a five-time CFO. He's going to be in the Baseball Hall of Fame for CFO someday. And I've taught my kids that lesson. Like, that's something that stays with me. Just listen. You don't have to speak every time a question is asked. You don't need to participate in every discussion. Listen, observe, think, speak when it's really going to be impactful, right? Now, on the flip side, I said, speak up. And speak up is about the mistakes I made at fab.com, for example. But I think we all make those mistakes, which is, you know, especially like, let's say, as a high-functioning executive team, if there's something that's being said or contemplated, especially before a decision is made, speak up if you disagree.
29:37Ideally, have data-driven, data-informed reasons for it. Don't sit back and say, well, I'm going to be the minority speaking against it, or I'm going to be the only naysayer. No, no, no. Say your piece. You don't want to get to a point where you've made mistakes and then go over and over it in your head, asking yourself, what if I had spoken louder? For the context of listeners, Fab.com was one of the highest funded kind of a marketplace for buying goods around the dot-com boom. Like many other companies, did not have the best ending. They were burning an insane amount of money to keep the company going in comparison to the revenue it was bringing in.
30:20I believe he's reflecting on are the decisions they made around hiring people and the product roadmap. You know, I've always spoken about the hiring stuff, but if you're working with a technical leader, it can be daunting to question some of their decisions around the roadmap because you're not technical. David's approach is he's bringing data to the conversation when it is something that that may be outside the purview of a CFO, just to arm people with the correct information to make those decisions, even if you're not the person to make them. So speaking up, Ben, I don't think always means speaking up to say I don't agree with something.
30:53sometimes speaking up can be to provide context and numbers that would better serve the leaders around you. We'll get back to the Microsoft example in a second, but kind of going back to that, like how do you build that kind of culture where the CFO is saying something like, I think we're wrong about this. I think this was a mistake is welcomed rather than punished. Having forums to share data and information because nobody likes to have just thrown on their desk. This is wrong. This is bad. You made a bad choice. It should never come to that point. It should be a series of conversations around data and the context in your market scenario, especially as it relates to your competitors, and then the macro of where you can receive funding.
31:31That way, it's not just dropping this, hey, you did a bad job on somebody's desk. You have to have a culture where these discussions have a form. Maybe that's a Monday exec meeting call. Maybe it's a series of five key data points that everybody agrees are the most important to operate the business, and they're sent out every Tuesday at a certain time, and they're very accessible to people. So let's bring it back to Kurt from Clio now. He's got a little bit of a full circle for us. I think that's one of the biggest mistakes CFOs can make. I think most of us get it in the private world and in the venture-backed world that that's the way things operate.
32:07But it's really important that you don't come in as a know-it-all and full of your own self-ego and believe that you have all the answers. Because there's some things that you just may not know that the founder wants to drive towards, or there may be conversations going on between a board member and the founder that you're just not a part of. And so, you know, approach everything with a growth mindset and to get your issues heard. Otherwise, if you come in and say, look, you got 10 problems, buddy, and, and, you know, there's big issues on the horizon, like 99 % of founders will just shut down on that.
32:46Yeah, yeah, yeah. We're left alone. Right. To solve those problems. You never want to fail alone either. Yeah, yeah, exactly. That's crazy. I didn't know that this clip was going to be in here. When I started the top of the podcast, I was talking about the triangle and you being in the weakest position as a CFO. The answer isn't always to push back and it isn't to never push back. So how do you know when you've kind of earned that right to push back? Before you push back, you have to seek to understand. That's what Kurt is getting at here. It's the first principles of why are they trying to do this thing, right?
33:18I think you also gain trust from showing somebody that you have a genuine interest in their business. Also, I hate that we can't use the word genuine or genuinely anymore because at ChatGPT, people think that you're reading off a script, which I'm not. But that is how you earn trust, through curiosity. That shows people that you're invested in their business and you seek to understand. The failure to speak up, maybe it initially comes from fear, but it seems like it's more nuanced than that. I think it's the social dynamic part of not wanting to call somebody's metric ugly. I've written about this before, too.
33:48It was called Beware of All Green Dashboards, which I think is a problem that CFOs will get into where they're measuring something they know intuitively has lost its connection to the ground truth of the business. But they continue to do so because the metric was invented by somebody a while ago and they did things a certain way. But they continue to cite this all green dashboard because they don't insult anyone. It goes back to the tribal tendency of wanting to be accepted. And if you challenge something, people inherently tie it back to their personal worth. Oh, am I bad at my job? And so I think that's what a lot of us avoid.
34:23You get around that by having that culture where you're constantly discussing things. And that can't be a check the box exercise either. It has to be a scenario where people lay the business on the table for others to understand. Before we started recording, we were talking about how we report metrics. and I felt comfortable coming to you about like, there was this just sort of thing that was going on that we couldn't really trust. I understand this may reflect on myself, but I just want to make sure that you have all the information and hopefully we're on the same page as well. Oh, totally. I mean, like there's so many analogs to dealing with somebody who's maybe from the marketing team showing a pipeline number and it's 2.5X instead of 3X and they measured it wrong or the investment you put in, those are the right numbers, but didn't pan out well.
35:06As a CFO, not great if you jump down their throat and just yell at them. That doesn't actually solve anything. In fact, what you're doing is you're cutting off your stream of information to make future decisions. So it may make you feel emotionally better in the moment to yell at somebody, but what you're actually doing is harming downstream your ability to make better decisions because that person is not gonna come to you anymore, right? They're going to avoid it at all costs. Let's come full circle completely here. We started this episode out. Steve Ballmer, he was talking about the iPhone and the question that was hanging over everything that we've talked about today is whether anyone in that building could have said the hard thing and actually have been heard.
35:43So we know now what Kurt would say about keeping ego in the bottom drawer. We know what David said, the consequences of staying silent. We know what Alex Emmerman looks for in a CFO candidate when he asks about the time they disagreed with the CEO. We know Adam Ante thinks about the seat at the table being earned, not assigned. Let's flashback. It's January 2007. You, CJ, you are the CFO of Microsoft. Bomber just went on camera and he laughed at the iPhone. You know what you know. You've got the relationship. You've earned that trust. You've put your ego in the bottom drawer. What do you walk into his office and say?
36:15I would say, Steve, this isn't an issue of what anybody said today. We have an issue that six months ago, we were not discussing the right data to even know where we stood in the market to make a claim like that. It's not a problem of what was done today. It's how did we arrive at this point where nobody felt comfortable saying, this is the current traction we have with this product. This is the investment we've made in the product roadmap. And these are the metrics that we use to judge success. It's less an indictment on that moment in time and what was said and more an indictment on the culture that was created to live in that warped view of what good performance looks like.
36:53And he's just screaming, developers, developers, developers. Sweating profusely on stage. Developers, developers, developers, developers, developers, developers. developers i feel like you kind of have to throw the espn phone example at him of like look they weren't they weren't wrong they were just early you can be wrong and early but it's better to to have those conversations even earlier any other parting thoughts before we wrap i love this man this was a lot of fun it was a blast from the past too just to watch how much the podcast has developed shout out to you and steve for continually improving the quality of this it's come a long way And at the same time, the guest wisdom is evergreen.
37:31It's still so pertinent even in today's world. So, so much has changed, I think, in terms of how we produce the podcast, but it's just so valuable to look back on these lessons. So great job. Thanks, man. And it's really cool seeing how pretty much every guest we talked about today, it wasn't cherry picked as far as what their status was currently as a CFO. Truly every guest that we talked about is either still in the seat that they were when we talked to them, you know, 18 months ago.
37:57CJ Gustafson: Or in a better seat. Yeah, a better seat. So it's cool. Run the Numbers is a mostly media production. Yelling an intro by Fat Joe. Artwork by Meg D 'Alessandro. Show is executive produced by Ben Hillman. Nothing said on this podcast is intended to be business or investment advice. It's the sole opinion of me, a guy who feeds his dog way too much ice cream and has a history of net operating losses, LOL. If you like this podcast, hit subscribe and give us five stars. It will take like two seconds and our algorithm overlords love it. Drink water, call your mom and have a great day. Peace.
On this special episode of Run the Numbers, CJ Gustafson revisits standout moments from past conversations with Alex Immerman, Curt Sigfstead, Daniel Kang, Adam Ante, and David Laptor. Together, their advice reveals how great CFOs earn trust, challenge founders, speak up when the data says something is wrong, and become true strategic partners without relying on the power of the purse strings.
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LINKS:
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TIMESTAMPS:
0:00 Preview and Intro
3:27 Alex Immerman's favorite CFO interview question
4:54 What a weak answer looks like
5:26 When the hard calls actually matter
6:37 Walt and Roy Disney
7:36 Liked even when making unpopular calls
8:43 Sponsors — Anrok | RightRev | Pulley
11:35 Curt from Clio: ego in the bottom drawer
13:52 CFO as supporting cast
15:10 Backbone vs. ego: when to use each
16:23 Daniel Kang: don't use the purse strings as power
17:36 Earn the seat, don't demand it
18:52 Money is one arrow, not the whole quiver
20:39 Sponsors — Rillet | Maximor | Brex
23:54 Adam Ante: finance people pigeonhole themselves
26:46 The CFO can sit in any meeting
27:30 First 90 days: listen before suggesting
28:46 David Laptor: listen, observe, think, speak
30:50 Build a culture where speaking up is welcomed
31:51 Curt from Clio: don't come in as a know-it-all
33:08 Earn trust through curiosity
33:46 Beware of all-green dashboards
35:28 What would CJ say to Ballmer?
37:14 Parting thoughts from Ben
38:00 Credits