The Sensitive Orifice

Redfin published an essay in TechCrunch today, “To Steve or Not to Steve,” about entrepreneurs who impose their personalities on a startup.

Redfin’s Matt Goyer read it first, to make sure it wouldn’t offend anyone. Matt’s an insightful soul, so I knew he would also appreciate the nuances of my argument.

When he was done, he looked up and said, “So you’re saying I should be a ***hole.”
“No,” I said, “I’m saying you should be a sensitive ***hole…” We stared at each other. “Or maybe not an ***hole at all.”

It’s a tough balance. As the CEO of InterContinental Hotels Group said of himself in a recent New York Times profile: “I’m very sensitive to how people are thinking and feeling at any given moment.”

But he also described himself as a super-action hero, boldly acting on his own in ways that surprised everyone. And this is what’s nearly impossible: to know how a decision will make everyone feel, then to make that decision anyway. It’s why many great technology entrepreneurs have mild forms of Asperger’s syndrome: it frees them to act, to decide, to drive people without much emotional friction.

If you don’t start that way, maybe that’s how you end up. Last week, I saw the “September Issue,” a documentary about Anna Wintour, the head of Vogue Magazine, and her efforts to publish its phone-book-sized September 2007 issue. It was moving to see so many flamboyant, talented people work so hard to make something irrevocable, definitive and perfect; many are undoubtedly now unemployed.

The entire movie consists of Anna walking into one room after another, picking one skirt or photo out of 50, and leaving the creators of the other 49 absolutely annihilated.  Time and again, she is asked how she feels. She mostly answers with the warmth of a bare steel table.

For some, it is necessary to be this way. The historian Edmund Morris described a day he spent with President Reagan, starting just outside the elevator with an unscripted photo opportunity alongside a police officer, blinded in the line of duty. This meeting and the ones that followed put Morris through the wringer; the sensitive writer was exhausted by lunch.

But Reagan, famous for momentarily failing to recognize his own son in a handshake line, deftly moved from one emotionally drenched encounter like this to another without apparently feeling a thing. Morris concluded that this detachment was the only way Reagan could make any decision affecting millions.

I don’t know if the choice is that stark for all of us. In the mostly dreadful Wim Wenders film, “Wings of Desire,” the angels can hear the thoughts of everyone in a train, on a street or in a cafe. The film is a near-unbearable cacophony of mortal thoughts that gradually becomes a comforting hum. When one angel forsakes his heavenly powers, he enters a cone of silence, unable to know what anyone is thinking but now able to act in the world. He can’t believe how lonely it is.

This loneliness is all well and good if you’re Ronald Reagan, or Anna Wintour, or an angel, who knows just what to do. But for the rest of us, the cacophony is essential to making a decision.

We engage people because we have to in order to figure out the best course of action. This is what makes deciding in the end so painful: that we’ve identified with a point of view completely that we then have to reject. It is hard to be emotional and then unemotional. It is hard to lose yourself in your company’s mission without occasionally forgetting the feelings of the  people on the mission with you.

But I have never given up on the idea that you can — and you have to — strike a balance between empathy and decision.


  • Susan Stone

    Interesting article Glenn.

    It is about choice. Every leader and every employee has a choice about how they show up at work.

    A ***hole leadership can equate to – short term productivity- low engagement – compliance mentality – drone like behavior from a workforce. The industrial revolution is famous for creating this type of leader and employee and it still exists in many forms in organizations today.

    Authentic leadership allows space for an employee to be intrapreneurial – engage in healthy debate – human conversations – recognition that employee #2467 is more than a number; they are a human being – able to walk the fine line between listening and moving forward despite disagreements in the course of action – courageous and vulnerable because a leader is a human being and not infallible.

    It is about choice on both sides of the equation from the CEO and to the employees.

    How are you showing up today?

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