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10 Timeless Qualities of True Leaders

Got an email from a veteran of the tech industry today. He was reading my new book, and had some questions. Turns out we’d both worked with a few legendary CEOs and VCs chronicled in the book, and when he talked about the qualities that set them apart, his words could easily have come out of my own mouth.

While the tech industry continues to be a breeding ground for talented executives and business leaders – many of whom become obscenely rich, as did those we were discussing – cultural norms have changed dramatically as of late. And the qualities that made these rare individuals successful are becoming harder and harder to find.

The culprit behind this enormous shift is our increasingly selfish, self-centered, self-absorbed “Me” culture, courtesy of our growing obsession with personal branding, blogging, and social media.

While that’s unfortunate, there is an unexpected silver lining. If you have a burning desire to accomplish great things and become wildly successful, you’ve got less competition than ever before. All you’ve got to do is break from the content-generating crowd and embrace the qualities that make great business leaders, well, great.


You can certainly make it big with an enormous ego and a grandiose personality. How else do you explain Donald Trump and Mark Cuban, with all due respect, of course? That said, humility – knowing what you don’t know – is not just an endearing quality; it’s an extremely underrated and powerful leadership trait, as well.

Related: Want to Be Successful? Quit Searching for Answers.


Empathy is widely misunderstood these days, courtesy of the massively overhyped fad, emotional intelligence. Let me tell you where it really comes from. It comes from being genuine. It comes from being true to yourself. That’s the only way you can ever feel real empathy for others. The same is true of respect.


I’ve never known a great executive to back down from a challenge on an issue he felt strongly about. Granted, we all have to pick our battles, but if it’s important and they’re confident – if their instincts tell them they’ve got it right – they’ll defend their position and put their money where their mouths are without hesitation.


To be successful over the long haul, you have to be market and business savvy. You have to know how things work and how to get things done in the real world. Unfortunately, many execs let their egos get in the way of that. They think they walk on water or their products do. They think they know more than their customers do. They think the laws of supply and demand don’t apply to them. That’s why they fail.


Great business leaders have an elusive ability to relate information and experiences from disparate situations to solve complex problems and boil them down to simple insights and strategies everyone can understand. That’s why their epiphanies and visions often sound so simple, in a “Why didn’t I think of that?” sort of way. It’s uncanny.


In a world where so many leaders will stop at nothing to get elected to another term, rope in another client, book another gig, sell more products, or grow the bottom line, it still takes honesty and integrity to breed trust and credibility – the cornerstone of strong, long-term business relationships.


If you dream of becoming an accomplished entrepreneur or executive, then you’ve got to find what you love to do. If you don’t, you’ll never have the tenacity and fortitude to stick with it through all the tough times ahead. When it comes to business, you’ve pretty much got to go through hell to get to heaven, and if it feels like work, you’ll never make it.

Related: No Matter What They Say, Failure Sucks


The term fearless gets tossed around a lot but it’s a misnomer. Everyone feels fear, except perhaps psychopaths capable of compartmentalizing their emotions. The difference between great leaders and the pack is that they have the courage to face their fear and act in spite of it. They do the right thing.


Smarts may not be everything, but I’ve never known a successful business leader who lacked intelligence, critical-thinking skills, and a genuine thirst for knowledge. As comedian Ron “Tater” White likes to say, “You can’t fix stupid.” He’s right.


Not only do great executives always seem solid and grounded, they also appear to possess a sense of calm and balance. They don’t panic and, even when they do feel stressed under the extreme conditions we often see in boardrooms, they never let it affect their decisions. That’s the mark of those who stand the test of time.

The challenging aspect of deconstructing these folks is that their qualities blend together to form whole, substantial beings that are so much greater than the sum of their parts. But in reality, there’s a lot more going on under the hood than it seems – qualities and behaviors developed through years of experience.

In case you’re wondering where all these timeless qualities come from, now you know. They come from experience – always have and always will.

© 2014-2023 by Smart Group LLC.

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