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Podcast Host
Indeed is a success story.
Interviewer (Scott)
Partner.
Podcast Host
Now here's your tech hiring tip of the week from Indeed. 73% of tech workers say flexibility is one of their top priorities. So if your job posting doesn't mention flexible hours or remote options, you're basically invisible to three out of four candidates. Keep that in mind. Look, hiring tech talent right now, it's tough. You are competing for people with super specific skills. Everyone wants hybrid work and the salary expectations are through the roof. It's a lot. That's why Indeed actually makes sense. They're the number one place where tech people go to apply for jobs. We're talking 3 million tech professionals in the US and 86% of them have applied through Indeed. It's not just some job board where you post and pray. They've got tools like smart searching and their tech network that uses AI to connect you with people who actually have the skills that you need. Companies using the tech network saw over four times more relevant applications. That's huge more qualified people. Way less time wasted. Whenever I've needed tech talent in the past, Indeed is the only platform I choose. And if I needed to hire top tier tech talent today, I'd still go with Indeed. Post your first job and get $75 off at indeed.comtechtalent that's indeed.comtechtalent to claim this offer. Indeed. Build for what's now and what's next in tech hiring 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 press sure.
Interviewer (Scott)
You'Ve been in. 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? What's. 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 that? Who's the reader?
David (Guest, Author and Leader)
Great question. The reader is for both leaders and aspiring leaders, is what I would say. If you have 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 like 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.
Podcast Host
Right?
David (Guest, Author and Leader)
So you're making hundred decisions a day. And, and, and what I wanted to is I always wanted to kind of write a book. I teach at Columbia, so I love kind of teaching and education and, and it's always been important to me. But I didn't want to write in these boring, like, you know, textbook kind of books with just like the five principles this, the six principles that, whatever kind of stuff. I want it 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, you know, 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, like, whether you're gonna after you have a kid, like, that's a trapdoor decision. But most decisions are incredibly changeable and 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 WeWork was so insane and such a roller coaster experience and made for just some pretty crazy.
Interviewer (Scott)
Material, I was going to say. So I feel like, and like 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.
David (Guest, Author and Leader)
You learn from what to do just as much as you learn what to do. Yes.
Interviewer (Scott)
So you've been. How many, how many, like, chief executive roles have you held over your career?
David (Guest, Author and Leader)
Well, that's pre. I would say this is my third president or CEO or CEO role. And if you include general management positions, then it's my fifth.
Interviewer (Scott)
So what is out of. Obviously you have some experience with this. So what is, what is, what is the definition of a leader in a business context? And what is the most important trip trait for a leader?
David (Guest, Author and 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's role is to support enable the success of their managers and 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.
Podcast Host
Square is a Success Story Partner now there's this coffee shop in my neighborhood that just started as this tiny little corner spot. Now they've got three locations, they're selling online. They've even added some food. So what I love is that no matter which location I go to, whether I'm grabbing my morning coffee or I'm picking up lunch, everything just works smoothly. The ordering, the payments, the loyalty points, it all syncs up perfectly. And that is the power of square. And honestly, it's why I keep going back. Every business has different goals and square is the platform that supports them all. Whether you're opening new locations, selling something new, or expanding your reach, I see it everywhere now. The corner bagel shop that became the chain specialty markets, managing thousands of items. Even my barber who takes appointments online. Square Point of Sale has the flexibility to run and grow your business exactly how you want. So whether you're in retail, running a restaurant, offering services, or you're just doing it all, there's a square point of sale mode built specifically for what you need. Different settings for different parts of your business so you're always ready to make the sale. Go to square.comgo/success story to learn more about how your business can grow with square. That is sq u a r e.com go go success story HubSpot podcast network is a success story partner.
Interviewer (Scott)
If you like Success Story, you are going to love some other great shows.
Podcast Host
In the HubSpot podcast network. It is the audio destination for business professionals.
Interviewer (Scott)
One of my favorite is Business Made Simple.
Podcast Host
It's hosted by Donald Miller, an incredible.
Interviewer (Scott)
Friend, a great entrepreneur.
Podcast Host
Business Made simple takes the mystery out of growing your business. So if you're trying to figure out how to get to the next level, what Donald does is he gives you tactical steps that actually move the needle. And in your business, you can go.
Interviewer (Scott)
Listen to Business Made simple anywhere you get your Podcast Business made simple part.
Podcast Host
Of the HubSpot Podcast Network, SurveyMonkey is a success story partner. Now look, we get it. You can hardly go anywhere or do anything these days without hearing about AI this or AI that. And if you're like most people when it comes to AI, you're impressed, but you have a few concerns. But what if AI was used not as a tool to replace people, but as a way to help understand people better? AI from SurveyMonkey is designed to do just that. From crafting the perfect survey, which is harder than you might think, to analysis that digs deep, finds patterns and services trends quickly. SurveyMonkey's powerful suite of AI capabilities makes it faster and easier than ever before to get insight from real people helping you make confident decisions for your business. Try it today@surveymonkey.com Scott Now I agree.
Interviewer (Scott)
With, I agree with what the role of the leader is, and I want to, I want to understand your opinion about how to do this tactically when there's interests of other parties that are, that maybe prompt different decision making. 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, in a, 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.
David (Guest, Author and Leader)
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 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, 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 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, like, our financials and post them on wherever 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, you know the way to go. And it goes with managing someone. You need to be transparent. If 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, 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 transparency to me is like the end all. Be all.
Interviewer (Scott)
This is like. This is like radical candle.
Podcast Host
There you go.
Interviewer (Scott)
Like, that's true. Yeah.
David (Guest, Author and Leader)
At our company, we have, like, a book. We had a book club.
Podcast Host
Yeah.
David (Guest, Author and Leader)
And Radical was one of the books in the book club. Yes.
Interviewer (Scott)
Yeah, I. I have no doubt it was.
Podcast Host
It's a.
Interviewer (Scott)
It's. 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.
David (Guest, Author and Leader)
And tell you one other thing about it, if you don't mind. Yeah, yeah.
Interviewer (Scott)
So, no, it's your show, man. You say whatever you want.
David (Guest, Author and Leader)
It's your show, dude. It's not my show, but, like, I'm still gonna, like, say it, so go for it. The. There's one of the most famous managers leaders ever. In fact, he won Time magazine's manager of the century for the 20th century was Jack Welch, the CEO of GE General Electric for. 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 meet 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.
Interviewer (Scott)
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, there's like the large companies that have probably been around for a long time that operate the way that they feel like they have to, you know, 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 scary feeling. But yeah, go ahead. No, no, go ahead.
David (Guest, Author and Leader)
If you're a startup and you don't have a Runway of 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. And people just 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 in we worst case, the truth was actually worse when we work. But for many companies, it's not.
Podcast Host
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.
Guest: David Siegel (Ex-CEO of Investopedia, Author of "Decide and Conquer")
Date: November 14, 2025
In this episode, Scott D. Clary sits down with David Siegel, seasoned executive and former CEO of Investopedia, to discuss the art of effective leadership through decision making. Drawing from his book "Decide and Conquer" and a career spanning multiple CEO and general management roles—including time spent navigating the tumult of WeWork—David shares deep, hard-earned insights on transparency, alignment, and enabling the success of others. The conversation hones in on how leaders can minimize misalignment, foster trust, and avoid the all-too-common traps of opaque or fear-based decision making.
“If you don’t have an interest in ever being a leader, it’s really not a book for you. But if you’re leading or want to lead, it’s for you.” – David (02:09)
“I wanted it to be a story that was riveting… where through the storytelling, you learn a ton about smart decisions.” – David (02:38)
“People think many decisions are trapdoor decisions when in fact you could change lots. You can’t change, like, after you have a kid… But most [business] decisions are incredibly changeable.” – David (02:46)
“Your role is to enable the success of everyone around you… The leader is on the bottom of the chart, not the top.” – David (04:36)
“Sometimes it means letting go of people to enable them to succeed. To me, that is the most important role of a leader.” – David (05:00)
“The biggest challenge… is because a board will have access to certain information… and employees have a different incentive. The more that a leader can ensure there’s as consistent information as possible… the better.” – David (08:51)
“Kindest thing you could do is give very critical, transparent, maybe overly blunt… information in as respectful a way as possible." – David (10:32)
“Is there a risk? Yes… But the reward of having alignment… because you’re brutally transparent is the way to go.” – David (09:54)
“Get everyone aligned. Or else people start jumping to conclusions… Usually those assumptions are far worse than the actual truth.” – David (12:54)
“Just focus on transparency. Focus on trust. If you build transparency, you’ll have trust. And if you have trust, you could have anything.” – David, relating conversation with Jack Welch (11:30)
On Leadership’s Core Purpose:
"My role is not to succeed myself… I need to enable the different people on my team to succeed. And guess what? Then I succeed.” – David (04:45)
On Information Sharing:
“Our board does not know any information that every single employee does not know and get access to.” – David (09:38)
On Conflict from Mismatched Interests:
"Everybody agrees what a good leader is, but nobody knows how to do it when their board and owners feel the need to do things differently..." – Scott (08:12)
From Jack Welch:
“Make sure you have trust of your employees, trust of your board, trust of your team. That’s all—that’s the most important thing.” – Jack Welch (as recounted by David) (11:40)
| Timestamp | Segment Description | |------------|--------------------------------------------------------------| | 01:41 | Scott asks about the purpose and target reader for Decide and Conquer | | 02:09 | David describes the book’s target audience and themes | | 02:38 | Why storytelling is a powerful teaching tool for decision making | | 04:26 | David defines leadership and the top leadership trait | | 08:45 | Scott probes how to align leadership principles with shareholder interests | | 08:51 | David details the need for radical transparency in leadership | | 11:00 | Jack Welch’s advice on transparency and trust | | 12:54 | David’s advice for startups facing existential risk |
David Siegel's lessons distill decades of leadership into two actionable imperatives: lead through radical transparency and focus on enabling your team’s success. By sharing hard truths, inviting open problem-solving, and aligning everyone through substantial information sharing, leaders can neutralize misalignment and build resilient, high-trust organizations—even under pressure. Whether you’re leading seasoned executives or just starting out, Siegel’s “Decide and Conquer” philosophy offers a beacon for authentic, transformative leadership.