Leadership Defined: Deconstructing the Buzzword
Scott D. Clary | Mental Models, Performance, Business & Entrepreneurship
Here is my weekly email with some insights and ideas pulled from conversations I had on my podcast as well as some other tools and resources you may find useful.
👑 Leadership Defined: Deconstructing the Buzzword
💻 Tool Of The Week: Moni Talks
🎧 Things You Should Listen To: David Siegel - CEO of Meetup
📚 Things You Should Read: Decide and Conquer
💡 Other Thoughts
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👑 Leadership Defined: Deconstructing the Buzzword
Let's talk about leadership. If you're at all involved in the corporate, entrepreneurial, or general business space, I'll hazard a guess that you've heard this word thrown around a lot.
That's because 'leadership' has undoubtedly become a buzzword in recent years; in fact, a simple Amazon search can demonstrate this. Type the word into Amazon's book search bar and over 60,000 titles will be pulled up in a matter of nanoseconds.
Today, though, I want to get past this idea of 'leadership' as simply a vague concept or idealistic platitude. Helping me in this process is Mr. David Siegel – CEO of Meetup, and last week's guest on the Success Story Podcast.
David Siegel, CEO of Meetup
As always, I'll start by introducing our guest. David Siegel is the CEO of Meetup, a company that helps people connect with others in their local community who share their interests.
David is also the author of Decide & Conquer, which outlines a killer decision-making framework (the one he used when taking over as CEO of Meetup). It was fascinating to hear his views on community, technology, and of course, leadership.
Here are a few more interesting facts about David:
He's been in the technology and digital media space for over 20 years
Before Meetup, David was CEO of Investopedia – a highly successful business information website
He was also CEO of Seeking Alpha, a crowd-sourced service in the financial market space
David has a BA in Philosophy, Politics & Economics and an MBA from the University of Pennsylvania, and is an adjunct professor at Columbia University
As you can tell, he's a busy man – but he was kind enough to come on the show and talk me through his extensive thoughts on leadership. Let's see what he had to say.
When we think of a 'leader', especially in the present day, it's hard not to picture a person who is quite self-absorbed; someone who is held on a pedestal and worshiped by followers.
Today, though, I want to challenge you to separate the word 'leader' from politics and religion. Why? Because I think this view of leadership is limiting; and not just limiting, but detrimental to our individual and collective success.
Instead, I challenge you to view leaders as the people who serve others. Look up any leadership quote, and you'll have this interpretation confirmed many times over:
"To command is to serve, nothing more and nothing less." (Andre Malraux)
"Outstanding leaders go out of their way to boost the self-esteem of their personnel." (Sam Walton)
"We live in a society obsessed with public opinion. But leadership has never been about popularity." (Marco Rubio)
"A leader is best when people barely know he exists; when his work is done, his aim fulfilled, they will all say: we did it ourselves." (Lao Tzu)
"As we look ahead into the next century, leaders will be those who empower others." (Bill Gates)
This isn't to say that the word of famous people is the only word – but I think, upon reflection, you'd agree with all of these statements. Think back to times in your life when you've been mentored or inspired by someone. What made that person a leader in your eyes?
Most likely, it was their ability to see what you couldn't see in yourself and to help you find it; to serve you, not their own agenda or self-image.
David Siegel's interpretation
Now, let's dive into the expert opinion.
In our interview, I asked David directly this question: what is the definition of a leader in a business context?
"My role is not to succeed myself,” David said. “I need to enable the different people on my team to succeed. And guess what? Then I succeed. But that's my job: to enable everyone else to succeed around me, and do whatever is necessary."
What a simple, yet beautiful definition of leadership! Leaders are not the people who succeed themselves; they are the people who enable others to do so.
David gave a really great explanation of his viewpoint on leadership that I think you'll find valuable. He explained it like this:
"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. Think of a 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 executives role is to support and enable success for managers; and the managers' role is to enable the success of individuals."
Where our traditional view of leadership puts the 'leader' at the top of the food chain, David's view flips it upside down.
This is a very different view than what we're typically exposed to in the media or in politics. It's also quite different from how most of us think about leaders. But it's a view that is in line with the times. We are living in an era where more and more people are recognizing the importance of community, and the need for collaboration.
Leaders today need to be servant-minded; they need to be aware of the needs of their followers and be willing to meet them. In a world that is constantly changing, this type of leadership is more important than ever.
Leadership is Decision-Making
"A true leader has the confidence to stand alone, the courage to make tough decisions, and the compassion to listen to the needs of others." (Douglas MacArthur)
Have you ever been in a situation where a decision needs to be made, but no one wants to make it? Maybe you're deciding where to go on a road trip, or even just deciding where to eat takeout.
You can brainstorm ideas for hours; you can write a pros and cons list until your hand cramps; but at the end of the day, no one is going anywhere until you make a decision.
Oftentimes, this is what leadership is: making decisions when no one else wants to or knows how. It's not about having all the answers, it's about taking the first step and inspiring others to follow.
This was certainly true in the early days of human civilization, when our ancestors were tasked with deciding where to hunt, what to build, and how to survive.
Fast forward a few thousand years, and the challenges of leadership haven't changed all that much. Businesses still need to make decisions about where to expand, what new products or services to offer, and how to respond to competitors.
In times of crisis, leadership is even more important. The decisions made in the wake of a natural disaster or financial collapse can mean the difference between life and death, success and failure.
David Siegel's Leadership and Decision-Making Principles
Defining leadership is important. I think it's fair to say that we've narrowed it down: a leader is someone who serves and empowers others, using their decision-making abilities to help their team reach success.
But I don't just want to define leadership; it's important to learn the practicality behind meaningful leadership, too.
David is someone who, knowing that leadership involves making tough calls, has transformed decision-making into an art form.
I spent a fair portion of our interview discussing principles from David's book, Decide and Conquer, in which he discusses "44 Decisions that will Make or Break All Leaders." He explained that, oftentimes, leaders fail because they neglect to notice their decision-making biases.
Biases That Ruin Decision-Making
David was generous with his leadership advice, giving valuable tips like:
Focus on being kind – not just being 'nice'
Create options for yourself, rather than limiting your scope to make decisions
Identify your decision-making biases
I want to focus on that last one. Have you ever let your personal biases affect your ability to make a sound decision? I know I have. We all have cognitive biases that creep up from time to time and can distort our judgement. Recognizing and understanding these biases is one step in minimizing their impact on our decision-making process.
There are dozens of different cognitive biases, but I'll walk you through the ones David highlighted as particularly relevant to listeners:
This bias is driven by the fact that we tend to remember recent events more vividly than those in the past. As a result, we can be unduly swayed by recent information when making decisions.
"Yoga can be exhausting," David said, "But at the end, you do a Shavasana. You're chill, and you're relaxed – and that's what you remember most. So you want to go back to yoga, because you did that Shavasana at the end. You have that recency bias."
You've likely heard of this bias before. It's when we favor information that confirms our pre-existing beliefs or hypotheses. This bias can lead us to make poor decisions, as it can prevent us from considering all the available evidence objectively.
"When things aren't going so well, you don't really look at that information – you're looking for things that confirm what you want to see, as opposed to seeking out different opinions of others that can actually help you to make a smarter decision," David explained.
It's tempting to be a sheep, and to blend in with the crowd, especially in the business world. But this bias – the tendency to prefer things to stay the same – can prevent us from making necessary changes and adapting to new situations.
"Oftentimes, people prefer to have the status quo. Even if it sucks, and it's terrible, and they're miserable, and they're unhappy; the fear of the unknown could be potentially worse, even though it's likely going to be better."
Sunk Cost Fallacy
Finally, the sunk cost fallacy is the belief that we should continue investing in something (time, money, etc.) because we've already put so much into it. This fallacy can lead us to make bad decisions, as it can prevent us from cutting our losses and moving on.
We see this a lot in the entrepreneurial space; people want to hold on to their businesses, even if they're not doing well, because they've invested so much time and money into them. But at a certain point, it's smarter to cut your losses and move on.
Can you identify any of these biases in your own life and leadership? I certainly can – and I see great value in being aware of them. Awareness is the first step in mitigating their impact on our judgement.
When we're aware of our biases, we can start to question our assumptions and make decisions more thoughtfully. We can also look for ways to offset their influence, by seeking out dissenting opinions, for example, or by taking more time to consider all the evidence before making a decision.
Transparency: The Golden Rule
We've defined leadership, we've explored decision-making, and we have identified our personal biases – but I want to finish on a slightly different note, by highlighting one of the most valuable parts (in my opinion) of the interview with David Siegel.
As a leader in any capacity, whether you're the CEO of a Fortune 500 company or the manager of a team of two, there will be times when your vision does not align with that of your team. Maybe your stakeholders want you to make a decision that you don't agree with, or your team is pushing for a change in direction that would be counterproductive.
In these types of situations, David advocates for transparency; and not just in times of conflict, but always. He shared a piece of wisdom from highly successful manager Jack Welch.
"Just focus on transparency. Focus on trust. If you build transparency, you'll have trust; and if you have trust, you can have anything."
Transparency in Business
What does transparency look like in business? I think it means to treat your "followers" as equals, making your processes completely accessible and understandable, and sharing your reasoning (even when it's uncomfortable) so that everyone is on the same page.
It also means being authentic and vulnerable. Leaders who are successful in this way aren't afraid to let their followers see them sweat. They know that by opening up and being real, they're building trust – and that's essential for any successful relationship, personal or professional.
David made an excellent point that with transparency comes a level of risk, which is why many companies opt to enforce hierarchy and secrecy. It's easier to make decisions when you're the only one who has all the information, and it's comforting to know that your team will blindly follow your orders without questioning them.
But in an age where information is democratized and technology has made communication more instantaneous than ever before, this type of leadership is no longer viable.
"To me, transparency is pretty much the be-all and end-all," David said – and I wholeheartedly agree.
Wrap-up on Leadership Defined
If you're currently in a position of leadership, you'll know better than anyone that it's not an easy role to fill. You aren't sitting up in your ivory tower giving orders and expecting them to be followed – you're working with people, building relationships, and trying to get the best out of them.
(That is, if you're the type of leader we defined at the beginning of this article!)
It's also an incredibly rewarding role, especially when you find a spot of wisdom that brings clarity to a complex situation, or when you see someone else grow and develop under your guidance.
Hopefully, today's article has served as a spot of inspiration for your time as a leader. If you've enjoyed the small outtakes from David Siegel's interview, I cannot recommend this episode enough – he's a highly experienced and intelligent leader, and I'm sure you'll get a lot out of it.
💻 Tool Of The Week: Moni Talks
Given how everyone and their mom is now into DeFi, Web3, NFT’s and Crypto, I thought it would be good to link a resource for those that are still having trouble understanding the entire category. The goal of Moni Talks is to deliver daily news content, covering all of the aforementioned categories, but simplified. So you can get your crypto news, stay up to date on the industry, and not need to go back to college to take CS, just to wrap your head around it. Great publication for someone trying to keep their finger on the pulse of what matters.
🎧 Things You Should Listen To: David Siegel - CEO of Meetup | Decisions That Make or Break All Leaders
On this weeks Success Story Podcast, I sat down with David Siegel (@Davidmeirsiegel). David is the CEO of Meetup, the largest platform for finding and building the local community. He has over 20 years of experience as a technology and digital media executive leading organizations through innovative product development, rapid revenue growth, and digital traffic acceleration.
Prior to joining Meetup, David was CEO of Investopedia and before that, President of Seeking Alpha. David holds a BA in Philosophy, Politics & Economics and an MBA from the University of Pennsylvania. He is an adjunct professor at Columbia University where he teaches strategic planning and entrepreneurship.
He hosts the podcast Keep Connected, which is dedicated to the power of community. David’s book, Decide & Conquer,(HarperCollins) lays out the framework for decision-making that leaders can use to ensure organizational and personal success.
Here’s what we spoke about on the last episode of the Success Story Podcast…
The definition of a leader
Leadership principles & shareholder expectations
Skills to hire for
The importance of de-prioritization
📚 Things You Should Read: Decide and Conquer
Decide and Conquer helps all leaders navigate the big decisions that will impact their future and make their organizations a success. David outlines the 44 challenges leaders face when starting a new position. He then shows you the decision framework he applied to overcome these challenges as CEO of Meetup. David takes you on an epic journey of corporate and personal survival that includes industry titans like Adam Neumann, Barry Diller, Jack Welch, Bill Ackman, and other leaders. In the book you’ll learn to:
Apply principles like open communication, transparency, and kindness to inform great decision-making.
Set yourself up to succeed, even before you start, by removing potential roadblocks before they become a problem.
Be a bold and decisive leader and not succumb to fear.
This story teaches over lessons David’s learnt through his career as he took over as CEO of Meetup. Although he covers them in the podcast, he goes into extreme detail of every lesson that he learn’t pre-Meetup, to every action and decision that he took while serving as CEO of Meetup and navigating transactions, crises and growth through WeWork. Decide and Conquer walks you through the key decisions you will face (because David’s already faced them) with invaluable advice for each one.
💡 Other Thoughts
1. On Quitting
Everything can turn around for you in a day. But you wont find out if you quit before that day comes.
2. On Work
Sometimes you don’t find a higher purpose or a deeper meaning until you do some grunt work.
3. On Problem Solving
Being able to solve problems at scale is the ultimate business model.
4. On Followings
Focus on being someone who's worth following, not your follower count.
Success Story Podcast
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