The Leap of Leadership


When I was a boy, my family went on vacation to the Grand Canyon.  This was so long ago that we actually gave a ride to a hitchhiker.


He was a young man with a backpack, a skimpy beard and a confident attitude.  As always, my father struck up a conversation, “So, what do you do?” he asked.

“Oh,” answered the young man, “I’m a writer.”

“Really,” said my old man, “What have you written?”

“Well,” the kid replied, “I haven’t actually written anything yet.  But it’s all right here in my head,” he tapped his temple, “and all I have to do is just write it down.”

As it happens, I grew up to be a writer.  And I’ve often thought of that hitchhiker. In the intervening years I’ve learned that a lot can happen — most of them bad — between that narrative in your head and what finally appears on the page.

Real writers write. Steve Jobs famously said something similar:  “Real artists ship.”  That is, a lot of new companies have impressive business plans, brilliant marketing strategies, and revolutionary products on paper.  But if they can’t get those products into the hands of users then they are merely unrealized potential, untested in the crucible of the marketplace.

Nowhere, I think, is this yawning gap between theory and application greater — and at the same time less understood — than in leadership.

For more than thirty years — longer now than anybody — Silicon Valley has been my beat.  In that time, I’ve met, and often known well, nearly every important leader in high tech history.  And yet, I think I understand the true nature of leadership now less than ever before.

For example, consider the leaders themselves.  Some of the legendary leaders of Valley history were men and women of great learning and wisdom.  But some were just damn fools.  Some were charming and courtly, others were monsters.  Some were born lucky, while others seemed cursed to fight ill-fortune every day of their lives.  Some were deserving of success, yet knew mostly failure; while others became rich and famous with no real right to either.  And yet, smart or stupid, angels or devils, worthy or undeserving, each one of these individuals proved to be a successful leader.


What are we to make of all this?  I mean, beyond the fact that life isn’t fair?

Frankly, I think it throws into doubt almost everything we thought we knew about leadership.  Contrary to what we’ve been taught and read, maybe there is no single recipe for becoming a successful leader.  Perhaps there are only aptitudes and opportunities – and then a million different pathways to success.

Ultimately, it may be that all we really know about successful leadership is that leaders lead.

Perhaps what really matters, as with that hitchhiking writer of my childhood, is not what happens in the leader’s head, but what happens when he or she makes the commitment to actually lead. When he or she takes responsibility for getting a group of people – from a start-up team or department, to a nation – from here to there . . and to deal with the messy, unpredictable, and perverse real world in-between.

This suggests something that we all, I think, intuitively know:  real leadership is not about skill or technique, but commitment.

We’ve all had inept bosses who ultimately succeeded because they put heart and soul into their work, and who abandoned any formal technique and just learned to cope with whatever came at them.  And we’ve all had bosses who were either “natural” leaders, or who had learned their lessons well — but who failed because they never gave themselves completely over to the task at hand or to the people they led.

You can be taught the ten skills of great leaders, and the importance of establishing clear objectives and maintaining communications with your people — but not how to convince your people not be afraid, when you yourself are shaking inside;  how to get them to believe in you when you yourself are filled with doubt, and most of all how to convince a normally incompatible group of people to become a team and work for a goal greater than themselves.


Leadership, I’ve come to believe, is not about knowledge, but character.  And not necessarily good character — but rather, the character necessary to lead to victory.  Leadership is not about ideas, but process.  It is not about preparation, but execution.  It is not about strategy, but adaptation.  And in the end it is not about attitude, but success.  That’s how some of the biggest jerks we know can be among the most successful and admired leaders of our time.  In the world of leadership, nice guys don’t finish last, but neither do they finish first — indeed, as hard as it is to admit, perhaps neither niceness nor goodness have much to do with it at all.

And that brings me to the most important question of all:  are real leaders born, or are they made?  Can that character, that commitment, be taught?   No, I think not.  No more than a religious studies course can make you believe in God.  That takes an epiphany that can only come from within.  But once you’ve made that leap of faith, the door of leadership is to open to anyone.

Think about it:  A Chicago talk-show host or a Cupertino telephone hacker, a Stanford assistant football coach or a Seattle code writer . . .anyone can become a successful leader.  And if leaders are born, not made — over the long term, those who make that commitment ultimately re-make themselves.

When I think back about that hitchhiker, I hope that he finally made his own leap and at last put pen to page.  I like to imagine that he became a famous writer whose name we all know, and whose work we have all read.  Wishful thinking, perhaps.  But then, it is on such wishes that leaps of faith of every kind are made.  Including the choice to lead.


Adapted from Leader’s Legacy award speech, Santa Clara University Leavey Business School


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