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Why I Hire People With Flaws

Digital media lifer Jon Steinberg explains why he sees value in job candidates whom other employers often overlook

Do you have any glaring personality flaws? Great! Jon Steinberg wants to hire you.

Steinberg is the admittedly flawed human and founder-CEO of Cheddar, a new digital media company aimed at covering the business world for overlooked, younger audiences, by focusing on the businesses they care about (e.g., Apple, Tesla) with a decidedly millennial bent. (Imagine if CNBC were suddenly overrun with BuzzFeed staffers.)

If anyone can reinvent business journalism, it’s Steinberg, a Gen-X digital media veteran who’s proven himself expert in both business and youth-oriented media over the past two decades. His media career actually started at age 15, when he worked as an Imagineering intern at Disney and helped make the company’s first virtual reality ride. “You were flying around on a magic carpet in the Aladdin movie,” Steinberg said in the commencement address he delivered last week at Columbia University’s School of Engineering and Applied Sciences.

Steinberg would go on to work for some of the largest, most influential companies in internet history, including stints at Google (where he helped build the company’s small business advertising division), BuzzFeed (where he helped the site transition from cute listicle factory to lucrative web property) and MailOnline, where he helped American-ize the salacious British tabloid.

Now, Steinberg is his own boss, a job that comes with the challenge of determining who will join his young company and managing a staff nearly half his age. Below, Steinberg discusses his somewhat libertarian managerial style, the most common mistakes people make when being interviewed and why he prefers people who ask for equity in the company instead of a higher salary.

Being the boss of a new venture, what advice would you give to someone starting their own business?
First of all you’re never the boss. You’re never running the show. You’re a coach. Maybe a team captain. People have to feel empowered. The dictatorial style does not work. It doesn’t get the best ideas and people just don’t do what someone tells them to do. It just doesn’t work like that anymore. People have to enjoy their jobs and what they’re doing. That doesn’t mean you’re sitting in a bean bag chair all day, but you’ve got to have people playing the positions they want to play. It’s very much like managing a sports team. You want to win the game but you can’t put someone who wants to be playing shortstop at the catcher position. They have to have the right mitt and they have to be playing in the weather they want to be playing in, otherwise they don’t perform.

What in your work history helped you learn that lesson?
It’s self awareness. I’m a flawed person and I like hiring people that are flawed people. When you recognize weaknesses in yourself, what you perform well and what you don’t like to do, you project that onto others. I always felt that everybody always gave me a difficult time and didn’t let me do what I wanted to do.

How so?
A lot of people give me grief. I don’t particularly want personality critique, and most people don’t want that either. I have very clear ethical rules on how I want people to treat each other, but beyond that I just want people to be themselves and do what they want to do. I guess I have a more libertarian point of view.

How do you think people perceive you?
People judge because I’m a little hyper active and high energy. My entire career, people told me not to be high-energy and that I’m too anxious and too worried. But that’s just who I am. I’m not going to not be anxious or worried about everything and I’m not going to not be high-energy. In fact, when people told me that, I found it very paternalistic, so I try not to be paternalistic. I like having people work with me that are very anxious and high-energy because I can relate to that. In fact, it must be hard to work with me if you’re not anxious and high-energy.

Is that what you meant earlier when you said you look to hire people who are flawed?
When somebody comes in here to interview, and they’re a young person and maybe they’ve emailed us 10 times in a four-day period, or maybe they tell you that they were waiting in the lobby for two hours, I don’t think that’s a bad thing. When I was 23, I probably emailed the boss a lot. It’s not the best thing I could have done but I get it, and I don’t penalize people for stuff that I did when I was 24.

What advice would you give to somebody who is your age and is working with a younger staff?
My one piece of advice is, if you’re trying to copy what BuzzFeed did four years ago or trying to copy a management style that worked at Twitter or Facebook three years ago, that won’t work because the puck moves so quickly. You can’t do what was done.

When you’re looking to hire someone, what helps a person stand out?
For me, it’s all about those ancillary interactions. When you’re sending emails back and forth; when you’re scheduling; discussing ideas; or during the negotiation process, when you’re going over the offer — that’s when you learn who the person is.

When you asked them to send over some ideas, what is that interaction like? Do they respond quickly? Do they respond free of errors? I find that over the course of about 10 interactions, I can learn more than I can in one meeting.

If they come in and have a unique hobby, or somebody comes in and they have a unique way of taking notes, you’re like, Ok, this person is going to offer a different set of ideas. We hired a guy who’s a dungeon master in Dungeons & Dragons. There’s a level of creativity that’s going to come from that.

What’s the most common red flag?
You’re not going to believe me, but it’s when you send somebody the offer letter and they tell you they can’t get to a fax machine or a scanner. It means that somebody is trying to leverage you for a better offer or is not really sure they want the job or is lying to you. Because everybody has a phone, and if you really want to sign the offer, you take a picture of the signature page. Now when people tell me they can’t get to a fax or scanner, I pull the offer on the spot.

What’s a better way for someone to handle the salary negotiations?
It’s good to do some research. It’s good to have a sense of where the market is. There are sites you can go on.

Also, it’s unfortunate people don’t value equity as much. When somebody wants a little more money, and I say, “Do you want a little more money or a little more equity?” and they go with equity, I like that.

John McDermott is a staff writer at MEL.

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