Thoughts on Atypical Leaders

Marcus Flores
3 min readJul 17, 2018

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Wallflowers everywhere rejoice: introverted leaders are not oxymoronic unicorns. Instead, these traits form a powerful combination often overlooked in the garrulous West. This is the thesis of Susan Cain’s book, Quiet, which is worthy reading for anyone in the business and tech world.

Having worked in both fields for much of my career, I personally relate. Projects are easy, people are hard; you’ve no doubt heard or experienced this in some way or another. But it’s all the more difficult when, as an introvert, you spend the majority of meetings not speaking, and rather than look upon public speaking engagements as a time to entertain and inform, you feel more like a prisoner before a firing squad.

That’s not to say the Harvard lawyer has written a self help book. As cultural descendents of the Greeks and the Romans, Quiet forces us to look in the mirror, to a time when timidity among American children equated to a full blown mental disorder. Magazine ads ran stories for how to prevent shyness or “cure” it. Even the nation’s top intellectual centers bought into the idea. Cain Writes:

“Harvard’s provost Paul Buck declared in the late 1940s that Harvard should reject the ‘sensitive, neurotic type’ and the ‘intellectually over-stimulated’ in favor of boys of the ‘healthy extrovert kind.’”

Today’s hyper-connected world invites cultural collisions in which the loud continue to dominate the quiet. Cain points out that highly competent Asians — many of whom are far less extraverted than their Western counterparts — are often relegated to the role of “glorified laborers” instead of VPs or CEOs. It is ironic that the Harvard Business Review is now asking, “Why aren’t there more Asian Americans in leadership positions?”

Cain’s writing led me to reflect on other works that intersect with her ideas. For example, it’s not just reticent Asians that risk being be cast aside in the business world. Physical characteristics attach themselves to the archetypes of certain roles and impair our ability to evaluate talent. Close your eyes and imagine you need to hire a VP of Sales. What does he or she look like? Now put yourself in Ben Horowitz’s shoes when interviewing Mark Cranney:

“… [Mark] wasn’t what I expected; he didn’t fit the stereotype of a hard-charging sales executive…Mark was average height…He was a square guy…Not fat, just square. His square body seemed to fit rather uncomfortably into what must have been a custom-tailored suit — there is no way an off-the-rack business suit would fit a square guy like Mark…His seriousness was so intense that it seemed to make him uncomfortable in his own skin. He made me uncomfortable, too.” (From The Hard Thing About Hard Things)

Credit Horowitz, who went ahead with the hiring. One wonders if Opsware’s position had been less precarious (it was trading for some thirty cents per share at the time), would Cranney have gotten the job? It’s likely, partially due to Horowitz’s position on great executives. He asserts that the job of an executive is so incredibly difficult that no set of personality traits can clearly describe it. It’s therefore unlikely that Horowitz sees things in simple terms of introverts or extroverts, which might be the only criticism one can levy at Cain’s book.

Regardless, Cain’s ideas offer a worthy expansion on Jim Collins’ concept of a Level 5 Leader. From Jim Collins’ From Good to Great:

“The eleven good-to-great CEOs are some of the most remarkable CEOs of the century…Yet, despite their remarkable results, almost no one ever remarked about them! … The good-to-great leaders never wanted to become larger-than-life heroes … They were seemingly ordinary people quietly producing extraordinary results.”

Yet you don’t need a shelf of business books to find support for Cain’s ideas: Winston Churchill, Marissa Mayer, and Bill Belichick all come to mind. I challenge you to assess your workplace for signs that introverted leaders may be lurking. After all, the best speaker does not always have the best ideas; the loudest is not always right. Look no further than the orange haired occupant of the White House for redundant evidence that Cain’s book is not being read enough.

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Marcus Flores
Marcus Flores

Written by Marcus Flores

Product manager with a background in mid-late stage startups.

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