How I Hire: Desperately Seeking Chutzpa

In a 1994 interview, Steve Jobs told a story about when he was in high school and, one day, just called up Silicon Valley legend Bill Hewlett (of Hewlett-Packard). “His number was still in the phone book," said Jobs. "He answered the phone himself.”

Jobs asked Hewlett if he had any spare parts for a frequency counter. Hewlett not only gave him the parts, but gave him a summer job at the factory.

“Most people never pick up the phone and call,” said Jobs. “And that’s what separates sometimes the people that do things from the people that just dream about them.”

I’m no Bill Hewlett, but the best hire of my career was someone with Steve-Jobs-like chutzpah. I call it “strategic chutzpah.” And I think it’s one of the best indicators of whether an employee will be a blazing success or a profound dud. (For those who aren’t familiar with Yiddish, chutzpah is sort of related to the Spanish concept of "cojones," but without the anatomical connotations).

Here’s what happened: A few years ago, I was writing a book about living by all the rules of the Bible called The Year of Living Biblically. The Bible said not to lie, covet, or gossip, so that’s what I tried to do. (Not easy. I’m a journalist in New York, and that usually makes up 80 percent of my day). The Bible said I couldn’t shave the corners of my beard. I didn’t know where the corners were, so I just let the whole thing grow. By the end, I had quite some topiary hanging from my chin. (Put it this way: I spent a lot of time at airport security).

In the middle of the year, I got this email from a freshman at Brown University. It was a sharp, well-researched, well-written email, and he said he wanted to be a writer. Which I thought was a questionable decision in this day and age, but so be it.

This student said he was coming to New York over the summer, and would like to volunteer to be my assistant in his off hours from his job as a barista.

Now, remember, I was following all the rules of the Bible. And interestingly, the Bible, in the Old Testament, does condone Hebrew slavery. It's one of the most puzzling and disturbing of the Bible's laws, and I was struggling with how to follow it.

Thankfully, slavery itself is illegal in the tri-state area. But I thought, what’s the closest legal thing to getting a slave? Probably getting an intern.

So I said to this college student, “Okay, you can be my assistant, as long as you allow me call you my biblical slave.”

He said, “Great.”

And he came to work for me, and he was wonderful. He was a flawless researcher. He was brimming with ideas. He put some of my old clothes on eBay, since the Bible commands giving away the shirts on your back. He made Ezekiel bread, which is the type of bread they ate in biblical times (lentils, barley, et cetera).

At the end of the summer, as a sort-of thank you, I took him on a research trip to Jerry Falwell’s Church in Lynchburg, Virginia. (Part of the book dealt with exploring how other groups interpret the Bible)

And he was fascinated. On the way back, he said to me: “I have an idea. What if I transferred from Brown, the most liberal college in America, to Jerry Falwell’s college, Liberty University, probably the most conservative? And then I could write a book about it.” The idea would be his semester abroad in Evangelical-land.

I said, you know what? That’s a pretty interesting idea. And I connected him with my agent, and he wrote great proposal. He sold the book, it came out a couple of years ago, and it’s really good. It’s balanced and nuanced, not a hatchet job. It shows both the good and the bad of the evangelical lifestyle.

His name is Kevin Roose, the book is The Unlikely Disciple. And now Kevin’s a superstar writer at New York magazine and author of another great book about Wall Street called Young Money, coming out in February.

So now I tell potential interns. If you come work for me for free, you are guaranteed to get a book deal. (I actually don’t use interns; the idea of free labor makes me feel too biblically guilty. But that’s another story).

Point is, I wish I’d been as smart as Kevin when I was young. He didn’t just blanket the market with a bunch of form letters. He didn’t even go through alumni relations. He researched and targeted. He wrote a brilliant, personalized and attention-grabbing letter. And it worked. Strategic chutzpha. His tale is even featured in a book by Harvard Business Review writer Dorie Clark called "Reinventing You: Define Your Brand, Imagine Your Future."

Of course, there’s a fine line between strategic chutzpah and stalking. Kevin never crossed that line. But I throw that out as a caveat. Otherwise, I say to potential employees everywhere, get emailing.