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LEADERSHIP LEGACIES

Leadership Legacies

If you’re sensing that there’s a lack of great business leadership these days, you wouldn’t be wrong – but the good news is, you wouldn’t be entirely right, either. Often, the best leaders are the quieter ones, the ones who fit their roles so well that you barely notice them at all – but you see the results in their business operations and the strength of their corporate earnings and stock valuations. They innovate under the radar, then present the world with the best of the best.


Here’s more about what that looks like, why we’re not seeing it among the most “newsy” businesses and what you can do to amp up your inner genius to tap into your own best version of leadership, whatever that means in your life.


Let’s start with what makes a great leader, in my opinion.


Characteristics and qualities of a great leader

Characteristics of great leaders have been studied ad nauseam, but I think it’s worth discussing some essential qualities here, simply because pointing them out now makes it so obvious why the headlines are filled with tales of failing leaders.


Here, then, are my top characteristics of great leaders:

  • They’re excellent communicators: They’re great speakers (or writers or whatever form this takes) and great listeners.

  • They read the tape: Great leaders are empathetic and know how to read body language and read a room. Then, they process this information to predict behaviors and give people what they want and need – often, before we know it ourselves.

  • They understand their charisma: They know that everyone has their special sauce and they understand theirs. They also know how to temper or trumpet their charisma to gain trust and confidence.

  • They have big egos: In business and politics and even some family dynamics, it’s not possible to lead without big egos. But it’s also essential to know that imperfections exist and no one is infallible. Great leaders find ways to balance hubris and humility.

  • They act with integrity and build trust: Whether you’re an employee or a citizen, you feel as though you have a sense of where they stand.

  • They’re definitive in their actions: They move forward with confidence and are willing to persevere through hard times. They stick to a vision and see it through.

  • They know they don’t know everything, so they aim to keep learning: They stay on top of their industries but they also learn about everything else they can, from sports to politics to cooking. Certainly, that makes them more interesting, but it also helps them read the tape and spot changes to the zeitgeist more effectively.

  • They don’t know everything, so they surround themselves with talent: Great leaders find the best talent they can – people whose skills, experiences and perspectives complement and, when necessary, challenge their own. They embrace their team’s success and do their best to support it. Then, they give credit to the team’s success.

  • They know when to pivot or let go: The greatest leaders find the confidence and resilience to power companies and countries through challenges and on to success; they also recognize when it’s time to let others step in and step up.

No one possesses all of these qualities, but the best leaders likely have most.



Visionaries who can’t let go

Business leadership takes a lot of ego – you have to believe that what you’re doing is better than anything done before to keep you soldiering on through the trials of entrepreneurship.


But time and again these days, we see the failure of entrepreneurs who can’t let go.


Twitter is a timebomb under Elon Musk’s leadership and it seems that Musk himself (who, frequent readers know, I always admired for his industry-disrupting thinking) is on the verge of a meltdown. Mark Zuckerberg is bumbling through the Meta mess of his own creation and can’t get out of his own way. And no discussion of the current failures of newsy business leaders would be complete without proper mention of the crypto crashers, like Do Kwon of Terra/Luna and Sam Bankman-Fried of FTX.


Could they turn their companies around? Possibly. Only time will tell. But in the meantime, they’re causing a phenomenal amount of angst for thousands of employees, as well as potential losses for millions of investors.


Knowing when to walk away, especially from something that you created, is one of the hardest challenges of leadership.


How leadership impacts the real estate industry

On a bit of a side note but because it’s my industry, I’d like to take a moment to discuss leadership’s impact in residential real estate. In this realm, it’s brands that stand out more than the people at the helm and as I see it, many of the biggest names in the business are faltering now.


There are two key industry challenges and neither has been satisfactorily addressed. One is the role of agents: Their roles are undervalued, in my opinion, and I see the future of the industry as one in which agents are given even greater responsibility, due to their proxy fiduciary relationships and obligations, rather than simply as transactional players. They work on the most important fiscal transaction that most people undertake in their lifetimes; as such, the value of those agents who lead in the field is deeply undervalued.


To empower them, the other industry challenge has to be addressed, and that’s getting them the data they need to do their jobs in the best way they can and giving them the support tools to make the transaction process seamless. With the right tools, every agent has the potential to become their own business leader. It’s as simple as that.

Residential real estate should model itself after the asset-management business and industry leadership, then, must consider these challenges and opportunities and provide the tools and momentum to get us there.


Not everyone should be a leader, but you can still be great

In this discussion of leadership, I’d be remiss if I didn’t point to a fact of life: Not everyone wants or needs to be a leader.


If that resonates with you, no worries – you can still experience greatness, even if you don’t want the kind of outward attention that corporate and political leaders attain.


The essence of leadership is that people believe in you and you can garner that in a million ways: It happens through the small business you start, through your family dynamics, through your relationships with your people and pets. It’s having people follow your blog or watch your YouTube videos. It happens on your sailing team or bowling league. Even if you don’t set out to “lead,” each of us has the capacity to instill confidence, trust and belief.


The key is to be authentic to yourself first.


What will be your (leadership) legacy?

Even if Warren Buffet owns multi-million-dollar properties around the world, he’ll always be thought of as the Oracle of Omaha, living a simple life while amassing an incredible fortune and helping many others do the same. He hasn’t gone it alone, though, as great leaders never do: He’s always had Charlie Munger by his side.


Steve Jobs was both canonized and criticized for his leadership style, but he stuck to his vision because he knew exactly what he wanted to bring to the people. He also knew to surround himself with complementary leaders and prepared for succession. Tim Cook is not Steve Jobs and, in the end, that’s been to the benefit of all – not because he’s better than Jobs, but because his differences helped him step into the role held by a legend and continue to lead.


As an entrepreneur, I’ve experienced a lot of professional failure along with success. It’s the nature of the game. I also like to think of myself as a leader who is always learning – I know what I don’t know, I find people who can do things that are necessary and complementary to what I bring to the table and I do my best to let them shine. And, I think, I have a pretty good sense of when to let go, whether by selling a business or taking an entirely different path.


I’ve had a lot of great mentors over the years and I’ve learned about these essential elements of leadership from their examples. That doesn’t mean that I encapsulate all of the good qualities and none of the bad – but I do try to keep learning and doing better.


What will your leadership legacy be?


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