In this lesson's 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 out this framework, I guess. And I want to understand, when you wrote Decide and Conquer, 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 who wants to maybe do due diligence on the company they could be joining? 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. So, you're making hundreds of decisions a day, and what I wanted to do is I always wanted to write a book. I teach at Columbia, so I love teaching and education, and it's always been important to me. But I didn't want to write these boring textbook kind of books with just the five principles, the six principles, whatever. I wanted it to be a story that was riveting, and through the storytelling, you end up learning a ton around smart decisions that you could ultimately make to become more successful. So it's for that audience. 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 could change lots. You can't change whether you're going to after you have a kid, that's a trapdoor decision, but most decisions are incredibly changeable. And people are so fearful of making decisions because they think they're trapdoor decisions when they're actually not. And just other elements of decision-making. So that's what we did. And the story under WeWork was so insane and such a roller coaster experience. It made for some pretty crazy material.
I was going to say, so I feel like, and obviously you're on the inside, so I'm just going to speak as a layman on the outside. I feel like WeWork is not the epitome of great leadership decision-making.
You learn from what not to do just as much as you learn what to do. Yes.
So, how many chief executive roles have you held over your career?
Well, I would say this is my third president 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 with this, 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. To think about the reverse organizational chart where 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's role is to support and enable the success of their managers, and the manager's 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? Then 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 the role of the leader. And I want to understand your opinion about how to do this tactically when there's interests of other parties that maybe prompt different decisions. So for example, when you were acquired at Investopedia, obviously stakeholders, there was 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 a 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,' etc., or I transmit that information to someone else, it aligns interests in a much more effective way than if information is withheld. The biggest challenge oftentimes, and why there's lots of misalignment like you're referring to, Scott, is because a board will have access to certain information, like a company wants to go public or 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 problems because there's asymmetrical access to information. The more that a leader can ensure that there's as consistent information as possible so that 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 our financials and post them on Reddit? Yeah, they can. And there's a risk. But the reward of having alignment and incentives and priorities because you're brutally transparent is 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 say, 'Don't worry, keep it up. Everything will be okay.' And then surprise them later on. 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 transparency to me is the end-all, be-all.
This is like radical candid, like that's true.
