Lessons - 44 Decisions That Make or Break Leaders | David Siegel - Ex-CEO of Investopedia

In this lessons episode, explore how effective leadership relies on transparent decision-making and aligned incentives. Discover why most choices are more reversible than assumed, understand how leaders enable success by supporting teams through clarity and trust, and uncover how open communication reduces misalignment and strengthens organizations under pressure. You've been in so many different CEO roles and positions, and this is sort of how you've built up this framework, I guess, and I want to understand like when you when you wrote decide and conquer, what is that what is that meant to be? Who's this book for? What's it trying to teach? Is it for another CEO? Is it for somebody who's up and coming in their career, wants to maybe do due diligence on the company? They could be joining. Who's that? Who's the reader? Great question. The reader is for both leaders and aspiring leaders, is what I would say. If you don't have an interest in ever being a leader, it's really not a book for you. And what I found is that there's a number of principles that exist out there because as a leader, you're making hundreds of decisions every single day, even deciding not to make a certain decision and to empower someone to make a decision, is definitely a decision, right? So you're making 100 decisions day, and what I wanted to is I always wanted to write a book. I teach a Columbia, so I love teaching and education, and it was always been important to me, but I didn't want to write in this boring textbook kind of books with just like the five principles of this, the six principles of that, whatever kind of stuff. I wanted to be a story where that was riveting, and through the storytelling, you end up kind of learning a ton around kind of smart decisions that you could ultimately make to become more successful. So it's for that audience. And things like how do you think about whether a decision is a trapdoor decision, meaning you can't change it, which most people think many decisions are trapdoor decisions, when in fact you can change, you can't change like whether you're gonna have to have a kid, like that's a trapdoor decision, but most decisions are incredibly changeable and people are so fearful of oftentimes making decisions because they think they're trapdoor decisions when they're actually not, and just other elements of decision making. So you know, that's that's what we did, and the story under we work was so insane and such a roller coaster experience, it made for just some pretty crazy material. I was gonna say, so I feel like, and like obviously you're on the inside, so I'm just gonna speak like as a layman on the outside, I feel like we work as not the epitome of great leadership decision making. You learn from what we're not to do, just as much as you learn what you do, yes. So you've been, how many, how many like chief executive roles have you held over your career? So I would say this is my third president, CEO or CEO role, and if you include general management positions, then it's my fifth. So what is out of, obviously you have some experience, so what is, what is the definition of a leader in a business context, and what is the most important trait for a leader? Oh wow, okay. So let's go backwards. The most important trait for a leader from my perspective is understanding that your role is to enable the success of everyone around you, is to think about the reverse organizational chart where like the leader is on the bottom of the chart, not at the top, your role is to support and enable the success of all the executives, and the executive role is to support and enable the success of their managers and manage role to enable the success of individuals. My role is not to succeed myself. I don't need to succeed myself. I need to enable the different people on my team to succeed, and guess what, that I succeed. But that's my job is to enable everyone else to succeed around me and do whatever is necessary. Sometimes it means letting go of people to enable them to succeed actually. To me, that is the most important role of a leader. Support the success of those around you. Now, I agree with what the role of the leader is, and I want to understand your opinion about how to do this tactically when there's interests of other parties that are that may be prompt different decision-making. So for example, when you were acquired at Investopedia, obviously stakeholders, there were certain stakeholders that were making that decision because they thought it was for the benefit of those stakeholders or even shareholders. But in a business environment, how do you align that leadership principle which I agree with with the expectations of shareholders, for example, or owners or whatnot? Because that's the fundamental thing that I think I always see causing conflict. Everybody agrees what a good leader is, but nobody knows how to do it when they're bored and their owners feel the need to do things differently. For example, that obviously drive ROI or whatever that metric is, right? Good. Okay. So to me, the golden rule is all about transparency, meaning if I am told by my parent company or by my board, transparently, you're not doing a good enough job. You need to focus on this, not that, et cetera. Or I transmit that information to someone else. It aligns interests in a lot more in effective way than if information is withheld. The biggest challenge oftentimes and why there's a lot of misalignment like you're referring to Scott is because a board will have access to certain information like, oh, a company wants to go public or whatever the, we want to sell this company, whatever the incentive is for the board. And the management team or the employees have a completely different incentive. And then there's tension and there's problems because people have missed, there's asymmetrical access to information. The more that a leader can ensure that there's as consistent information as possible. So the most junior person and the board member knows the same thing, the better. And you could say, oh, David, that's unrealistic. We share all of our financials with every employee. Our board does not know any information that every single employee does not know and get access to. Is there a risk in doing so? Can that employee take screenshots of like our financials and post them on wherever? Read it. Yeah, they can. And there's a risk. But the reward of having alignment and incentives and priorities because your brutally transparent is, you know, the way to go and it goes with managing someone. You need to be transparent. Someone's not doing a great job. It's not nice to them, not kind to them to like say, don't worry, keep it up. You know, everything will be okay. And then surprise them later on kind of the kindest thing you could do is give very critical transparent, maybe overly blunt in order to be clear information in as respectful a way as possible. So transparent to me. See to me is like the end all be all. This is like this is like radical can. Yeah. Yeah. That's true. Yeah. At our company, we have like a book. We had a book club. And radical was one of the books in the book club. Yes. Yeah. I have no doubt it was. It's a great, it's a great leadership philosophy. So and this is what you're doing. This is this is one of the principles. And it's got to tell you one other thing about it. Yeah. You don't mind. Yeah. So no, it's your show, man. You say whatever you want. It's your show, dude. It's not my show. But like, I'm still going to like say it. So go for it. Um, the there's one of the most famous managers leaders ever. In fact, he won time magazines manager of the century for the 20th century, it was Jack Welch, the CEO of GE General Electric for 20 years at the time that he left the highest market cap company in the world. He was on IEC's board. And I got to sit down with him and me with him one on one. And I said to Jack Welch, you were the manager of like the century. What can you teach me about management like on one foot? And he's like, just focus on transparency, focus on trust. If you build transparency, you'll have trust. And if you have trust, you could have anything. Make sure you have trust of your employees, trust of your board, trust of your team. That's all that's, that's the most important thing. So that had an impact too. It's amazing because it seems like that runs counter to almost every company operating out there that seems to hide everything from their employees. So there's always like the large companies that have probably been around for a long time that operate the way that they feel like they have to hide everything. And you don't even, you don't know what the next person in the cubicle beside you is making, let alone what the company's financials are like, unless they're public. But outside of that, you also have the startup that's worried about sharing information because they may not have a run rate longer than six months. So it's very, it's a very, very, very scary feeling. But there go ahead. No, go ahead. If you're a startup and you don't have a run rate more than six months, I know that's scary. So you get the team together and you say, okay, who do you know? What angels do you know? Or let's be aligned, we got to reduce our costs. How can we focus on our hosting costs? What do we need to do to reduce costs? Just get everyone aligned or else people are like, why are they asking us to reduce our people to start jumping to conclusions? And frankly, usually those conclusions that they jump to, those assumptions that people are far worse than the actual truth that's actually going on, except when we worst case, the truth was actually worse than we work. But for many companies, it's not. Thanks for tuning in. If you found this valuable, don't forget to hit that subscribe button so you never miss an episode. And if you want to dive deeper into this conversation, check out the links in the description to watch the full episode. See you in the next one.