CFO Whisperer

Let’s talk with Jim Cook, CFO, startup Coach, and founder of BenchBoard. Jim works to build the next generation of operators and goes beyond just crunching numbers. We'll dive into the territory of culture in organizations and teams, and Jim's unique leadership philosophies and operating system that let him lead with who he truly is.

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Jim Cook is on the pod for this episode.  I’ve heard him talk about his role as a CFO in a way that goes beyond the numbers- into the territory of culture in organization and teams. I don’t hear that very often from CFO’s or from founders who talk to me about their CFO’S. And in that way, he’s unique- I love to talk with leaders who have an understanding of what they’re doing with a lowercase “d” and what they're REALLY doing with an uppercase D. 

Today we learn about Jim’s leadership, philosophies and operating system that let him lead with who he is. 

Jim Cook is a CFO and was early at Intuit, and part of the founding team at Netflix. He ran Mozilla’s Finance team and has developed a clear philosophy on what it is to go beyond the numbers and lead, leveraging the smarts and ideas of the people around him. He delights in the success, ideas and energy of others and is a joy to collaborate with. You can do that in this episode.

Connect with Jim here on LinkedIn & Twitter.

Check out his Blog.

Interested in 1:1 Exec Advisory/Coaching to help scale your leadership & operations? Book 30 min with Jim.

And be sure to check out all things Dia Bondi.

Dia Bondi  00:19


Hello everyone this is Lead With Who You Are. I'm Dia Bondi, and on this show, we are exploring and discovering what it truly means to lead with who you are. And we're doing it with people who work on and embody just that. And that does not leave me out of the equation. I am every day working on and developing how I can lead with who I am. And actually right now at recording this podcast, I'm at one of these inflection points where I'm recognizing that my goals tbh are making me miserable. Why? Because I realized just this last week, that these goals are not actually my goals. I took on a few goals a few years ago, that I kind of thought were the next goals I was supposed to have, and thought I could grow into really loving and and championing. And it turns out, they're just making me miserable. So last week, I recognize I'm shifting from one goal type to another and reinventing what it means for me to be successful, so that I can lead what's next in my business, in my own creativity and in my life from that place. So I invite you to consider what it means to lead with who you are, and make sure that what you're doing though it may be hard, what drives it is not making you miserable. In this episode, we're talking with Jim cook about what it takes to lead with who you are while you scale. In this episode, Jim shares a four part framework of leadership attributes that are designed for big impact, and he shares what he's learned early in his career at Intuit, and then at Netflix. During their big and first inflection points. He says, you're always an underdog, even when the story is a winning story. Let's go. Hey, just a quick reminder, you can subscribe to this show on your podcast platform of choice. We're live nearly everywhere and you can always listen to the show at DIA If there's a leader or innovator in your life, who is if they're shiniest when they lead with who they truly are, Please share the show with them and rate subscribe and leave us a review makes a huge difference in the reach that the show has. When you let everyone else know what you love about the show. Thanks so much. Ask Like An Auctioneer, my forthcoming book designed to help you Ask For More and Get It, is available for pre-order now. And when you order the book, you get some pretty sweet little bonuses you get a little video series with me sharing my favorite three of the nine ideas I learned from the world of auctioneering to help you ask for more and get your get a nice little downloadable set of quote cards pulled from the manuscript. And all of these are ones our pre readers loved the most and you'll be auto enrolled in the ZOFO challenge, a one week challenge to design and make a powerful ask go to and order your copy now. Jim's passion is sharing his 30 plus years scaling some of Silicon Valley's most iconic brands from startup to multi billion dollar outcomes. Some of those include into it Netflix and Mozilla. He has way over 10,000 hours of CEO partnering experience, and was mentored by legends like Bill Campbell, Reed Hoffman and others, and is deeply networked in the VC community. Jim's new company bench board is now focused on sharing his best of learnings and believes connecting people and sharing knowledge creates a powerful community and network of executives. He is portrayed in a few books that will never work and Netflix podcasts and in the award winning documentary Netflix versus the world. Today, Jim is busy curating and sharing the best ideas and leadership for his community of next generation leaders. Welcome, Jim. So Jim, it's so nice to see you. It's so nice to have you here. Great to see you again. Yeah. Okay. So, I'm having you on today, Jim, because I've heard you talk a lot about your role as a CFO in a way that kind of goes beyond the numbers and into a territory of how you can impact culture in organizations and teams, I don't hear very often from the CFOs and CFO types or from founders who talk to me about their CFOs in this way. And in that way, I think you are really unique. And I'd love to, I want to talk to you today. Because I love talking to leaders who have an understanding of what they're doing from a lowercase d perspective, what am I doing, and also an understanding of what they're really doing from an uppercase D perspective. While you might be working the books, you're also you've also talked to me about how you recognize your role in finance as a tool for change and for culture, cultivation, culture, growth and, and greater impact outside of whatever the the numbers are showing you. And, and I really, I know today, I want to learn about you and for our audience to learn about you and your leadership philosophies. And sort of the operating system that you use that lets you lead with who you are, as an example of how we can all have both a job and a rule that maybe are a little bit different. So I'm so glad to have you with me today on lead with who you are.


Jim Cook  06:15

I'm super happy to be here.


Dia Bondi  06:16

So for folks listening, and for me, just as a refresher, can you tell me a little bit about your own provenance and I think of that as like, the your origin story and the drivers that brought you to where you are now. I had a lot of freedom as a young kid. So I guess I'll go back to being a young kid. I had a lot of freedom as a young kid, I was really lucky to have parents that gave me a ton of freedom. And that that produced I think, a lot of creativity. So I grew up in a small town in northern California till I was 11.


Jim Cook  06:51

A lot of who Tiburon, California Marin County, not the not the Tiburon. You all know today, but but a Tiburon of 6000 people with 600 kids in the soccer program. And it was just hippie, hippie Ville. So I was roaming all over the hills, I now have houses on them. But only till I was about 11. But I think the provenance that you speak of is is my dad was a doctor and he picked us up in his his parents got sick, my grandma grandmother, and so did my mom. She was a nurse. And they moved us to small town, Ohio when I was 11. I tell people, the story in there said that must have been tough. And it was tough. And growing, going from a California kid to having all the freedom and creativity and into a small town in Ohio was a huge adjustment. The values are different. The judgment is different. But the people are great. But it takes a while to break in there. And so that I went from a very confident kid to a very unconfident kid at 11. And, and I think that that was a huge moment for me to understand who I am and how to get along with others better. Another part of my history has just been on sports and athletic teams my whole life. And so I really love being on teams. I've been lucky to have great coaches.


Dia Bondi  08:11

What do you love about being on teams?


Jim Cook  08:13

winning to, winning as a team and losing as a team, like it's a team sport, everything in life is a team sport relying on people. We were always the teams that I was on that I most, I think most people's teams, they're on it. They're not superstar teams, you're always the underdog. And you're always trying to be better. You're rarely are you on a team that is a championship team. Most of the time you're trying to to win and beat other teams, you never have undefeated seasons. And so learning how to loot win and learning how to lose, learning what it takes to win learning what learning why you lose is just a journey. And I think you really develop a camaraderie with your with your team members have through the really bad times and a camaraderie on the really good times. And you just pattern match at all.


Dia Bondi  08:59

It's interesting that you say that though, because looking at your own history, from your bio perspective and sort of the highlights like you it looks to us, like you've been in a lot of really on championship teams. Yet you're telling me that you're always on the underdog, you know, you've had huge impact in places like into it, you know, an enormous and willing brand, obviously, early, early co founder position at Netflix, incredibly winning brand. And Mozilla which is equally you know, you know, recognized as a high impact brand. So, it's a little dissonant for me to hear you say you're always the underdog when you've been in a lot of championships.


Jim Cook  09:39

Well, isn't hindsight 2020 And isn't doesn't doesn't history reflect more positively than the truth? The truth is, Intuit was 100 person firm when I joined. The truth is and this has been written from Scott Cook on down it turns out it was one of the best management team Still in the valley unseated a bunch of management, but at the time, there was no VC in the valley that has been written, that would give Scott Cook the CEO No relation. Any money, he walked up and down and got rejected 40 times. And he wasn't given any money from any VC Kleiner was the first Kleiner Perkins was the first PC to come in only after they were profitable. And nobody thought they would win huge underdog against Microsoft. Microsoft was the winner in software. And we were our our whole mantra, it was very much of a team effort was crushed Microsoft. That was Intuit for my first five years, we went from 100 person company, to a 3500 person company. We went from one product one function, one a bunch of functional departments, to five business units, and being public and doing several m&a days. And I was so lucky at being on the forefront of that as a 25 year old kid, and I say as 25 year old kid, Not to disparage any 25 year olds out there, but but when you're 25 you're kind of still a kid, and you're learning but I wasn't married. And, and and I spent, you know, 1618 hour days just learning everything I could.


Dia Bondi  11:11

And so I'm imagining if I'm gonna stitch those two stories of, you know, you're always an underdog and you were part of just even the way you told the story here of this championship, even though there's rejection early days, you know, there were you guys probably lost a lot of games on your way to that championship, a lot. Tough seasons, tough seasons.


Jim Cook  11:32

This is the story of most startups. We all hear about the glory of the intuits and the Netflix of the Mozilla's but the truth is, it is tough. And I tell I tell my clients today and I tell all the I try to pass it along to that every company I've ever known, has pivoted not once not but more than once in their original business model. Every company that I have ever been involved with Intuit Netflix and Mozilla really struggled for money in the early days. And most not Mozilla thankfully. But most have been down to their last payroll a few times.


Dia Bondi  12:09

Look ... at that's not the only struggle though. I mean, I work with I work with VC backed founders as in part of my coaching practice and in our intensive, which we're growing as a cohort based program and in the coming years, coming months and years. And I recognize that sometimes the issue is not I got one month of payroll, the issue is I got a pile of money and no progress. I got I'm super stuck. The products not shipping the way we want it to. It's different than how I imagined and the pain and suffering that comes with closing the gap between the the impact and the the client base and the product you imagined and the difficulty of bringing it to life. I mean, I am I self identify as a creative and as a writer, I just completed my first book, and, and living in the difficulty of the difference between what I put on the page and what I imagined the story needs to be is like, like, That's painful. So you know, when you're when your team is, you know, can check the box on we've got plenty of cash. You know, we have a lot in place, but we are struggling. What do you turn your attention to?


Jim Cook  13:23

Yeah, let's get into that a little bit. Let's finish up on the underdog. Big word. We have a lot to talk about here. But having too much money. And not being focused is one huge pattern that I've witnessed in my career. I've seen both sides. But just to finish up on the underdog. Netflix was a huge underdog. We were six people in in a few 1000 square feet. You know office building, making it up as we went and everybody said we were crazy. Mark Randolph eventually wrote a book a few years ago that was titled that will never work. And because everyone told us it will never work. We're crazy. No one's in we were this is the Netflix of 1997 of shipping actual discs in the in the mail with post office, not the Netflix you know today. I wasn't you know, VCs would give us money in the early days. And in you know, in Intuit was started on Scott Cook's last $100,000 of a home equity loan had he not done that the company would have cratered. Netflix was started on $2 million. And we scraped by to get a Series A of $6 million. This is not a lot of money to try to launch something is as as big as we've launched. And Mozilla let's talk about Mozilla being an underdog. I mean, Mozilla is like everyone thought we were crazy. The browser market was dead. Internet Explorer had 98.6% market share in 2005. And who are these 18 engineers who believe they can rebirth the browser market because it was lost years ago. Right and so it's really I really enjoy being on the underdog team because it it really is allows you to rally your team members together to really focus on a different future vision and to really celebrate the wins along the way with a lot of bumps. So that let's close out that underdog because I, I think it is a big part of my providence of really competing. And I and I, and I think of I think of business as a sport, I think of business as a team sport. And I bring a lot of that to how I practice leadership today and how I coach leadership today.


Dia Bondi  15:27

So, you know, maybe also recognizing that you're an underdog position does give you I love the idea of like imagining a different future like it does maybe tap into that freedom and creativity that you mentioned early on in your life that feels like sort of Greenfield moments, even though you are functioning with some very real constraints. So when you know, before we go on to the to your leadership philosophy, when did you start to realize and maybe I'm making an assumption in this question, but when did you start to recognize that while you're, you know, well, your career was in the CFO kind of lane, that you recognized that money? I can't remember, you said it to me a couple of years ago, somehow that like, you know, your CFO role can be a tool and a greater to have greater impact outside of just the books, you know, they can be used as a culture tool that it can be, it can be a leadership Lane organizationally, when did you recognize that like, oh, I can do that from this place.


Jim Cook  16:35

Honestly, in my 30 year career, it's hard for me to say I've been in Silicon Valley for 30 years, but I have about 15 years. And that's one of the reasons I'm so passionate about sharing back my lessons learned because what took me 15 years to learn, I'm convinced I can teach others in one to two years, just by sharing stories, but about 15 years, I had this belief system for the first 15 years, that you know, after a while people say, Oh, you were at Intuit. You know, and they and they, they give you more credit than you deserve. Oh, you were at Netflix, but about and you start believing that this role of who you are is who you are. And that's all it takes to be a leader. And then you realize when you're trying to grow a much bigger team at Mozilla, for example, from 18 people to 1200 people that that's not what it's about at all. That's maybe what you do. That's your title, but to lead people, you have to go back to your roots as that scrappy team sports team. And, and what you do is not who you are. And I think that's what I told you a few years ago. It's what you what you do is not who you are, it's what your subject matter expertise is I just happen to be good at math and finance, and I really enjoy the analytical side. But when you hide behind that as a CFO, because that's what you do, it actually alienates people because they don't understand how you do what you do. I think a lot of sea level leaders in the more technical and financial sides don't realize that you, you end up intimidating people a lot. And then you try to play this role of being perfect and never being wrong and having your forecast be 100%. Right. And it alienates others even more, even though they respect you for it. They don't really know who you are. And it when you so I realized it was about Mozilla, it was about three or four years into Mozilla, where I started finally getting cracked over the head that the PEEP reminding myself that it's that this is a team sport that the people matter more than my role. And if we really wanted if I really wanted to be a true leader, I would have to really lean into the people side of the equation, which which I have instincts for for sure. Small Town, Ohio, small town, Northern California. You know, as captain of my teams, we were underdogs. But I had to pull that all the way back out and not play this role of Of course, I had success at Intuit and Netflix, and you should just listen to me because I have a C level title now. No, that does not work. That does not work. You have to embrace the people side. So about 15 years in is the answer to the question. And then I've been practicing it ever since. And I came from I come from five generations of doctors and I remember my grandfather telling me what my dad also told me. He's when you go to medical school, they're the way they teach you how to be a doctor is you learn something the first two years, you do something the next two years. And then after you graduate medical school, you have to teach it in a fellowship for the next three or four years. You have to learn it, do it teach it. I have carried that with me since I've been 10 years old. I've watched my dad learn about being a doctor. Well, you know when he was 40 and 50 He's reading books all day long. I'm like, Well, I thought you were at a school that I thought yours successfully, he's like, I have to constantly be learning or I'm not going to be a better doctor. So I have this, this, this passion for just learning and learning, but also understanding that you don't get better at anything until you share it back and teach it. That's how you become a master at something. So that's, you know, you ask the provenance, provenance of who I am, I just have in this me this curious learner who really is passionate about giving back and sharing and teaching and hopefully, you know, winning as a team, trying to help anybody, you know, learn lessons that I've learned and, and giving back. That's what Silicon Valley is all about. What makes Silicon Valley unique, and its really its people look on it like it's strange is we give away information freely. There are other areas try to protect the other is the country and the regions really try to protect information. But we talk to anybody, the entrepreneurs in Silicon Valley and venture capital, and we share information with everybody, we try to make everybody better. It's a really interesting, there's lots of articles written about this. So that's why I love being here and working here in Silicon Valley. It's because of that culture of everyone shares back and everyone tries to make everybody better.


Dia Bondi  21:11

Well, and I'm hearing in there just a lot of sort of open, open source ethos that can, once you're in it, or been exposed to it, it kind of permeates everything this read right kind of approach to everything. Right?


Jim Cook  21:23

Correct. 100% Yeah, that Mozilla was a huge influence and impact on my career, I met so many great other leaders, including you, you know, you had a big impact not to not to make you blush, or anything, but you had a big impact on my career, by just teaching me how to be a better communicator, you were one of the leaders that we brought in to train all of us up just on how to communicate better. And I had to like learn that 15 years into my career,


Dia Bondi  21:52

and even still, Jim like my, my, since we engaged in that way and Mozilla years ago, like my own communications philosophy, like the the course or principles and models that I use have evolved and grown and sort and hardened in a positive way. You know, I have folks like you, clients, like you have taught me and folks listening will hear. And if you've, if you're listening, and you've worked with me, you know that I believe that communication at a leadership level is not just a transaction tool, it is an info transaction tool, it is a strike point for your leadership. And when we embrace, taking that on, like, Oh, when I communicate, I am in a position to have a huge impact because of my role and because of my job. And you can you'll approach those critical communications moments in a much more sort of thoughtful, empathetic, and respectful way. Because it's not about just disseminating information, or giving direction, it's about aligning and activating people in a way that helps them trust you also. So as you think about, you know, the instigators in your life and leadership that were really instrumental into how you operate today, maybe you've enumerated them in our conversation about your own sort of origin story and the things that drove you, you know, what lights or fire that got you to where you are now, or carried you or, you know, we're with you. Are there any other sort of key instigating moments that you find, were really instrumental in developing who you are as a leader today? Wins, fails, relationships, mentors,


Jim Cook  23:41

my soccer coach in high school, being mentored by Bill Campbell at Intuit. Personally, before he became the coach, everybody knows him to be he took many of us youngsters under his wings, because that's just what he loved to do. I've been very fortunate to be surrounded by some tremendous mentors, who had some of the same philosophies. But going back to what I just want to summarize what you just said, it was so powerful, and I hope, and I hope you repeat that or continue to repeat what you just said about two minutes ago. But I can almost summarize what you said that communication, and I've translated for me about this. It's about them. It's not about you. For up until about 10 years ago, I always thought communication was about me about being perfect about disseminating information, everything that you just said, I remember I used to be I tell people this all the time now. They think I'm crazy when I tell them they think I'm lying, but I was deathly afraid to get up in front of people and speak. I was because I didn't want to be embarrassed and I didn't want to look foolish. And I remember taking I took speech classes from this great speech teacher in high school and 18 I was the worst student In the class, I was just panicky, nervous, because I just I felt like I had to be perfect. And I always felt like I had to be perfect when I got up on stage. And all of that changed when I realized and it changed at Mozilla, that it's not about me. It's about them and it's about you're trying to share what you know, with them to make them better. And that was a huge unlock for me. I think you brought a lot of that to me. You know, the Katyn Athena's in the in the depth Cohen's of the world brought a lot that you know, to me and, and, and all the studying I did there, but that was a huge unlock for me, when you can make it about them and not about you in communication. You really, you really get a lot more comfortable. And now I'm super comfortable speaking because I'm okay with being wrong. I'm okay with stumbling this. It's you know, people look through that. 


Dia Bondi  25:49

They absolutely do. And in fact, when they have that more human experience of you, it is more trust building. And that is so often the objective. So I had a few questions prepared for this conversation that I'm going to toss aside in favor of the small conversation that we started yesterday in preparation for today, which was around sort of the way in which you think about sort of reflecting best less Best Practices back to your community of sea level and next generation leaders in in and around technology, through how you, you know, I'm gonna say like, how you curate content. So can you talk a little bit about your sort of, I don't know if it's a hobby or your fascination or an appetite you have right now for consolidating, condensing and reflecting back some of the the most compelling content that you come across today as a service to your community?


Jim Cook  26:50

Great question. I was just having this conversation the other day with a couple of really good friends and colleagues for years. And they said, they said, Jim, you're so good at, curate, you're so passionate about it, and I am. And I think it probably comes from my just being a curious learner. But even things like AI and how AI can be applied in today's modern operating stack. I'm not even gonna say finance stack and what what can't I just I just go deep and try to learn everything I can. But what's interesting about I guess, my brain, which I I thought was normal, but I guess a lot of people don't. And this is fine. They don't operate this way is. Every time I'm learning something, I think to myself, Wow, this is fast. And maybe this is a bit egocentric. Probably is it this is this fascinating to me, I have to share this with others. And so I get super passionate that if this is super interesting to me, it by definition must be super interesting to others. Turns out that a lot of times I get passionate about topics that are not super interesting to others. And people think I'm a geek and nerdy but but they they love the passion that I bring to a topic that they may not be interested in. But every once in a while, I hook into a topic that they really are interested in. And then when you can find someone who's as interested, but hasn't done the work. I just love finding any and all sources. What I say curating the best jobs and sharing them back. Very little of my work is original, though I do put an original spin on it. But I guess I've been told one of my superpowers is just going so deep. It's my analytical brain, probably it's the training over years, and pulling out the pearls of wisdom, the insights, from myriads of data points, and contextualize it. I you know, I come from a family of storytellers. And so even though I wasn't good at communicating, I was communicated to all the time through stories when you're when you when you have big families that from my mom's side, she was the night the nine kids. They were storytelling all the time. And this was just kind of part of what she did. There's a story about everything, when you can tell stories, and contextualize the data, to make it relevant to your audience. That's where it gets fun, why it matters, what to do about it, how to do it. And then when you get experience on how to do it, and then you can make the flywheel going up, not just the what but more importantly, the why it's important, and how specifically to do it. Or at least some ideas on how to do it, then it gets really tangible for people and learning starts happening. I'm very passionate about group learning. I do a lot of one on one coaching. But I'm also passionate and I do some group coaching but I'm very passionate about everyone learns from each other and I got that from muscle as well.


Dia Bondi  29:36

So talk to me about bench board and what you're doing with what is it and what are you doing with that cohort?


Jim Cook  29:42

Yeah, bench sports started as a as a interim CFO practice 20 years ago, when I was between things in the in the name for it was I it was a amalgamation of benchmarking, and dashboarding bench board benchmark dashboard that has it kept the name because it people think it's cute and they remember it. But it's now I've now turned that into a, a practice that does exactly what I just described, which is share back the best things that I've learned over 30 years in Silicon Valley scaling, leadership, scaling operations and systems and leadership, how to be how to scale leadership and operations at the right stage, and with the right, and at the right maturity level of the company, stage and maturity matters. There are different systems, there are different practices with your 50 person company, than if you're 150 person company, then if you're a 500, person, company, or 1000, or beyond.


Dia Bondi  30:45

So give me an example right now have one of the topics or models that you have in your mind that you're eager to share back with your bench board. Because you think that's relevant and useful to folks who are in that struggle that we started the conversation with, you know, that gap between what I envision something I'm leading can be and what it actually is today.


Jim Cook  31:06

Well, one of them I'm doing right now is is what does what does this gen AI? What is this chat? GPT? What does it mean for my business? And should I be paying attention to it? We have to recall this is all just literally nine months old. This burst onto the scene in October, November of last year for most people. And it certainly did for me. But because I've seen inflection points over time in my career, contextualizing the, this feels like 1991, Microsoft Windows before there was even Windows DOS and Mac, this feels like 1994 Netscape browser that sits on top of prodigy and CompuServe text based a first UI graphical interface kind of technology. This feels like AWS cloud when everything was data center, this feels like a lot of these inflection points that we've witnessed, and then saying, what did the what did the industry do during these inflection points? What did the winners do? What did the losers do? Or not do? And this seems pretty important, right? And how to actually build it in what tools how to actually start playing with it, what maybe how good an idea might be to start hiring a head of AIT, you might want to think, as a CEO to hire a head of AI, and maybe carve out time and force your leadership team to carve out time to also be curious and learn everything about it. Because if you don't, your competition will, and I'm convinced of this. And it's these kinds of lessons that I'm that I'm sharing back with my client base on Ortner. You know, you have to recognize the inflection points of technology in history. And you have to, as a leader, apply them inside of your organization.


Dia Bondi  32:53

So that's very tactical, we see something in front of us it's presenting either by default, like go to it, see it as an opportunity, or have a hint, that it's an opportunity or a hint that it's a threat, I'm going to go in, and I'm going to carve out time for me and my team to understand more so that we can contextualize what it means for us and make some decisions around it. Now, you know, leading in the face of a big opportunity, a big threat, a huge transition, a large inflection point, a realization that we're on the wrong path. There's a big decision in front of us or sort of a fork in the road a moment, it's a moment for us, what are some of the leadership attributes that you see are really imperative for founders or leaders to have today, when they are in these kinds of situations where there may be is ambiguity and no clear path, but one needs to be made quickly.


Jim Cook  33:48

Let's start with confidence. Like I think of these in in a in a couple of key variables. But we were talking about this yesterday, when you can get really authentic and vulnerable and people in in a trusted safe space like coaching one on one to CEOs or CFOs. And all of us have a little bit of this, but there's an underlying lack of confidence. When you're a leader of a I think this is normal human behavior of a startup or the more volatile it is, the more you're second guessing yourself. Let's just say it that am I doing the right thing. A lot of what I do is remind people like it's not about being right or wrong. It's about being confident in your point of view, moving forward and understanding how to course correct in case you're wrong. A lot of my practice comes down to one of my one of my big mantras is it's 85% 15% Everybody says 8020 But I like to say 8515 You're going to be 15% wrong and you should be 15% Wrong. Shoot for 85%. Right, that's fine. But embrace the 15% wrong and embrace the failure. And because you that's where all the learning happens. I'll take 85 to 90%. Take 90 to 95%. Don't castigate people and don't shame your leadership or your staff about being wrong, embrace it. Because that's where 100% of learning in life and in businesses, so it's just reminding these leaders to have a confident point of view confident enough. But have one.


Dia Bondi  35:21

Yes, have a point of view? This is a beautiful, that's a beautiful thing to recognize. I mean, in my because I live in the communications world, not I'm not an operator, you know, and I'm not, I don't coach to operating I coach to okay, you're an operator, how do you use your voice now that you're not necessarily a product manager or a product lead, you know, you're not a product guy anymore. You're a founder who's running a business, you're not a, you're not operating as a as a data scientist anymore. She's now founding CEO and has to sort of navigate that beyond her individual competency in one particular expertise area, right? It's a different challenge.


Jim Cook  36:05

Yeah, this, this, this variable of confidence. We're starting here, there's a couple other variables, they both start with C, we'll get to him in a minute. But this variable of confidence, if you think about communicating, it's about them. It's about your followers, it's not about you leading, remind yourself that you've been on the other side of listening to others, try to give their point of view who aren't confident and you don't, as an audience member, you start losing credibility. So there's a fine line of almost faking the confidence. And we hear these things, fake it till you make it I don't believe in that. I don't believe in that either. Yet, but But you have to be vulnerably confident, transparently confident, tell people what you know, and what you don't know, say you're making a decision with not all the answers, but tell them that you're willing to course correct as well. But we have to move forward.


Dia Bondi  36:55

So I call that in my world narrating the process, I've made this decision based on this stuff, here's what is unknown, I am okay with that being an unknown, here's what we will do when we learn after we take this action. So you're not you're not confessing because people people don't need to hear all of your nervousness come through, but they certainly need to, it is confidence building for them to hear you narrate the process so that you are building confidence in the decision, not just confidence in you. Now to go back to your idea, that like point of view, so often I work with founders and leaders who want to figure out what they should say before they've really taken into consideration and and said to themselves decided what their point of view is.


Jim Cook  36:56

well, let's you can break down point of view into what do you believe? What what what is your belief system as a CEO? And what are your first principles? And and what what do you value the most? The this is the work of of having a confident point of view. I've worked with many CEOs and leaders who simply want to pulse their leadership team pulse their board, and they ask a very dangerous question, what do you think? That's a good question. But if you don't overlay it with your own point of view, and say, Here's mine, please challenge me, I want to hear yours. If you only lead with what is yours, and and what you know, ask everybody else what they think. So that you can create your own point of view, then your point of view is constantly changing, because all of those answers will be different. See their strength and having a diverse set of opinions around the table. And everybody wants a diverse set of leadership, team members, board members, but there's a huge weakness in that strength. If you can't curate those points of view into one central leader, you are the chief executive officer for a reason. You have to take all these opinions. And then you have to say I've heard this I've heard that I believe this, I think we should go here principle you have to lead someone has to lead because if you're not leading, and you're just gathering a bunch of opinions, and changing your point of view, based on everyone's changing opinions, it's really dangerous.


Dia Bondi  39:08

So so we've got confidence, which feels like has a big component, a big component as I you know, from my perspective, big component is like actually developing your point of view, knowing what it is, you know, through various methodologies, but like, as you say, like having your own sort of first principles that guide that and inform it, what is the other what are the other C's that you mentioned in this model, you're talking about?


Jim Cook  39:32

Connection. So now we're back to the people thing. The connection with people and the way you get connection is through trust and being authentic and telling them why you're making a decision. Why your point of view I love I'm going to steal that do this this narrating narrating the process, narrating the process how you have to write this down so I can steal I think it's great. Yeah, this narrating the process process and can you, you can have confidence. But if you don't, if you can't connect with people on that, then you're viewed as arrogant, confident without being close to people is, is somewhat of a bad recipe.


Dia Bondi  40:15

So we've got confidence, we've got connection, and I would even posit that connection creates trust. It's not always, it's not always an outcome of trust, like those two things work with one another. If we can develop connection that breeds trust.


Jim Cook  40:30

there's a great song by the script, that people may know that there's us in trust. Yeah, trust requires us and us requires getting to know each other and relationships. So there's Jim Cook, being corny again,


Dia Bondi  40:43

okay, so there's connection, there's confidence, what are the others?


Jim Cook  40:46

Courageous, you have, you have to be you have to have the courage to speak the truth, to speak truth to power to its day different than in my opinion than then confidence, you can be confident, but not courageous. You'd be confident your point of view, it'd be pretty passive about it. But you have to be able to take that confidence, take that connection, and then make the actual decision, and be willing to make the mistake, you have to play on the risk curve a business of life, if you play it safe all the time. That confidence, the confidence, like I can handle anything that cuts that gets thrown at me, but you're always being reactive, versus the confident plus courageous, which is, we're going to go down this path, and we're not sure where it's going to lead. But we've looked at all the data, we've talked to everybody, and we're going this direction, follow, let's go follow me.


Dia Bondi  41:42

my, I have a I have a client who says that some of the some of the most courageous moments are the moments where you actually find the courage to defy the data. He's a data scientist who, and I love that idea.


Jim Cook  41:58

I think that's huge. Actually. If you study the history of successful companies, successful teams, they have done something differently than the masses, they have gone on a direction that was unique and different. They learned from all their competition, and they took an angle that no one else would take. And they had the courage to do that.


Dia Bondi  42:21

Yes. So we've got confidence, we've got connection, we've got courage. And the fourth one, I think there's a fourth one


Jim Cook  42:26

communication, then you have to know how to communicate the confidence, how to communicate the courage, how to communicate the connection with people, it all comes down to your practice dia, it all funnels into, if you can't communicate, you can be confident, and you can help be brave, and you can be connected with people. But if you can't influence them, to create the impact, to lead them with confidence to lead them with courage to be connected, and you're pretty silent behind all that. That's the missing piece.


Dia Bondi  42:58

Sometimes, you know, being too silent. But also being too loud. Isn't communication, either filling the space with only your words is not necessarily communicating. It's just dominating.


Jim Cook  43:07

Correct. Correct.


Dia Bondi  43:10

So, so, Jim, for you, as you think about, you know, curating your own leadership experiences, enabling and amplifying, accelerating, other founders and leaders around you in and outside of the CFO role. What is next for you? Like? Where are you going with what using this model that your, that your doctor family legacy brought that first, we learned then we do then we teach what is next for you and your sounds like you're in your teaching phase,


Jim Cook  43:43

I am in my teaching phase, I'm now going to be doing this full time. I'm really passionate about and I have found a following who hopefully we can get a bigger following. But I really want to learn from others that have that have taken their own content, taking their own learnings, taking their own doings, and I'm now studying others on how they create the most impact with what they know and Hatton and how they communicate it. And so I'm going to learn that from you. I'm going to learn that from others that I admire in the industry and try to pattern match it and and do my best at sharing my pretty specific content. It's scaling startups from series A to se series D. We can do some IPO readiness. I've done that, but I think I think the the majority of it is how do you scale companies at various stages? What are the lessons learned? What are the best of practices, storytelling, what worked for me what didn't work for me, but but helping helping my clients and helping groups of people customize this to their own needs? It never works when an expert or URI or anybody says, you know, this is the playbook. It's not about playbooks, though. I think in terms of playbook because if you just take anybody's playbook and overlay it, it will likely fail. You have to customize every business model, you have to customize every team based on who's on the team and the various talents. And you have to customize these best of frameworks and models and ideas. And that's where it gets fun. Tell me about your culture. Tell me about your belief system. Tell me about your opinions. Because I can tell you that these are the frameworks and models and how it works. But we have to customize it for you, your team, your company,


Dia Bondi  45:30

I think that's right. You know, and it's so tempting to just be like, just tell me what the 10 step plan is, that is so tempting, because it's, it's easier. And I think this is the difference too, between, you know, skills training, and the leadership development, skills training is here's how you do something, learn that skill and execute it, regardless of where you are. And, and, you know, it's almost context free. But leadership development, I think, is about developing our own voice, leveraging the power of other people's thinking frameworks that are resonant for us, so that we can come up with something that is as alive, and high impact for, for who we are uniquely as leaders. And in a way that is uniquely ours. And that is a journey nobody can take except the people that are sitting around your bench board.


Jim Cook  46:24

So I'm gonna give you a specific example. Because you just reminded me and it's a shout out to all of my Mozilla team that ever worked with me. Over the years, I was practicing a lot of this from about 2012, maybe 2010 for six or seven years with my team. So hello to everybody out there who may be listening on my old Mozilla teams. But you'll remember this, you will remember me coming into my leadership team meetings with you. And our team meetings and me saying something to the fact per this point, that, here's my point of view, I want to hear yours. We're going to develop a joint point of view and a joint desired shared outcome. But here's my requirement. And this was from accounting staffs. This was from finance staffs, from it staffs, and maybe HR administrative staffs, and a lot of people from behind the scenes who weren't as comfortable sharing their point of views. And I had one requirement for the 1215 people in the room that we met weekly, or every other weekend. I said, you have to challenge my ideas. I'm wrong. You have to speak up and tell me when you think I've said something wrong. Because if you don't, we will not win together. I'll tell you right now that I'm not going to be right, I'm going to have a clear point of view, I will challenge you, but you have to challenge me back and tell me it don't look at me as your leader as your seat. Like whatever I say goes, we will lose. I need you to look around corners, I need you to help me and help our team and you need to help your team look around corners. And to challenge what is instinct, if there's that feeling in your gut, that that's not the right idea. That's not the right point of view. And you sit there in silence, that's really bad. And this took this took a couple of years for people to get comfortable literally, with being able to say Jimmy said that in the meeting, can I have a one on one with you? And that they would start that way three, or you told me I can challenge you and then I made it safe for them? And I said, Here's my requirement next time, I need you to say that in the room with the other 15 people and challenge me publicly, oh, I could never do that some of these more shy people, it says it No, I'm required, I need you to do that. They need to see that it's safe. And so we built a very, very great team just with these kinds of operating principles and values. Everybody challenges each other. Everyone has a point of view. And the best ideas win.


Dia Bondi  48:51

So tell me answer this question we'll wrap what does it mean for you to lead with who you are?


Jim Cook  48:58

What does it mean for me to lead with who I am? I think when it's about them, when you truly make leadership about your followership and people are looking up to you, but when you can turn the tide and model for them. For me, it's about if I can model how to lead for people, then they'll pick up on it, and they'll leave their people. Because I had great mentors and managers. And I was lucky in that I, I mentioned that earlier in this podcast. And the science will tell you that when you have a great first boss or a great set of early managers, your career is three times better than if you didn't. And it's just stuck with me that that it's like having a great teacher or a great mentor. In the early days. It's it's really debilitating to have dysfunctional leaders and mentors. So I just try to model everything that I know and everything I've learned from my teachers and coaches so that maybe they can pick up on it and they can Do the script and the mantra have challenged me. And it's okay and I'm going to be vulnerable. And I'm going to make mistakes and all of these things that are kind of unusual for a CFO, especially a CFO to be talking about. It's about leadership. It's not about being a CFO or about being analytical. It's just a role. It's about leadership.


Dia Bondi  50:19

Fabulous, Jim Cook, it was so nice to talk to you today. Thank you so much for coming on and sharing your perspective.


Jim Cook  50:26

Dia, you rock, anytime.


Dia Bondi  50:28

Where can people find you?


Jim Cook  50:29 They can find me at @Cookflicks on Twitter. They can find me on LinkedIn under well you'll probably find me on Jim Cook. Just, just Google Jim Cook Netflix Mozilla, you'll you'll probably find a lot of my webinars and panels and other things I after 30 years. I'm it seems like I'm out there a lot on the web. So just connect with me. I'm open, like don't be shy. Say hi. And we'll have a conversation.


Dia Bondi  51:01

Love it. Thank you.


Jim Cook  51:03

Thanks Dia.


Dia Bondi  51:07

Lead with who you are is a production of Dia Bondi Communications and is scored mixed and produced by Arthur Leon Adams the third, have a question or an inquiry. Reach out to us at You can like share, rate and subscribe at Apple podcasts, Google podcasts, Spotify or wherever you get your favorite shows. Go to for the show notes to find our tools, frameworks, content and programs to help you and your team speak powerfully and lead with who you are.

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