“I Just Knew I Was Going to Surpass These Guys I Was Working For”

What I learned from the worst—and best—bosses I’ve ever had.

Kara Swisher speaking.
Kara Swisher is the co-founder of Recode. Photo illustration by Slate. Photo by Monica Schipper/Getty Images for Turner.

Executive Time is Slate’s pop-up blog about bosses. This as-told-to essay has been transcribed and edited for clarity from a conversation with Laura Bennett.

I’m not a good employee. You’re supposed to be obsequious when you’re an employee, right? You’re supposed to give in to people. At my first full-time editor job, at Washington City Paper, I felt completely out of my depth. My first boss, Jack Shafer, spent a lot of time arguing with people and not a lot of time mentoring. But I didn’t expect that he would be a mentor, so I wasn’t disappointed. I was hired for a job I wasn’t qualified for, and I don’t think I did a very good job. Well, I know I didn’t, because he fired me.

I don’t recall thinking it was so deeply unfair. I’m not one of these people who finds life deeply unfair. But I still had a sense that I had more talent than most people. I used to think that about a lot of people. I just remember thinking, I’m not more experienced than these guys are, but I’m going to be bigger than they are someday. I know it sounds crazy. I always felt like, I’m going to pass you so quickly. No, I don’t have the skills right now, but I’m so much more talented than you. It was just a matter of time.

When I was just starting out, I’d see some of the decisions my early bosses made and I’d think, I’m not experienced, but this is how I’d do it. I was beginning to get an inkling of my own tastes and judgment. I just didn’t have the certainty and maturity to act on it. I wasn’t a prodigy personality who is like, “Get out of my way, I’m doing this.” I was a little bit uncertain about my skills. But I just knew I was going to surpass these guys I was working for. I remember once I interviewed for an internship at the Washington Post, and a guy said I was too confident. I was like, “Why don’t you retire now, because you’ll be working for me?” Men are always trying to drag women down. I said, “I’m not too confident. I’m fantastic.” I was always, always like that. And I appreciate that about myself, I have to say.

My next boss after Shafer was John McLaughlin, of the TV show The McLaughlin Group. I ghostwrote his column in the National Review—he would add in the right-wing invective—and then I worked on his show. That asshole of a human being. I got the sense he sort of respected me because I didn’t put up with his shit. Because I wasn’t a Republican. I was a liberal, obviously. All these people were weird acolytes to him because he was a big deal during the Reagan administration. That was his power. So he used that. These people would do everything to work for one of the top Republican people, and I was like, I don’t give a fuck. My whole history is not going to depend on this. He enjoyed a smart woman in a weird, sick way.

He was awful and abusive and terrible—and as it turned out, he was like Sexual Harasser 101. He was harassing a woman on the staff who was a friend of mine. But he was abusive to the whole staff. He would line people up by height and then make them look for a dust ball under his couch. Stuff like that. This was Captain Queeg kind of behavior. He was just super crazy. Everyone had a beeper—he had to know where you were.

There was one incident, which I think they wrote about in the Washington Post, where he used to require that everybody make him toast. He liked buttered toast in a certain way. So he would have the chief of staff make him toast. And so he called me in one day and said, “Would you make toast?” And I told him, “No, I’m not making you toast.” And he said, “Everybody on staff makes me toast, and if you don’t, you get fired.” I said, “Well, I’m not making you toast. So you’re going to have to fire me.” And he goes, “Just so you know, if I ask you and you don’t make it, I’ll fire you.” I said, “OK, good.” And he never asked me, not once.

I remember once he was doing this party list. I was about 25 years old. He used to have this annual party for the Reagan administration that all the powerful people came to. He was going on and on about this party list and who he was going to let in and who he was going to snub … it was so insanely ridiculous. I said, “Can you please hurry? Because I’ve got something to do.” He turned to me and he goes—I’ll never forget this—“Don’t you know the collective power of the people in the room that I have assembled?”

He also used to make people call him Dr. McLaughlin, even though I don’t even know if he had a doctorate. I said, “Listen, Dr. McLaughlin, I was in Greece this summer at a temple and there was some writing on it that said: ‘Babylon was.’ Which means: Every major power falls.” So I said, “I took that to mean that someday I’m going to be really powerful and you’re going to be, like, in a wheelchair in an old folks home being fed apricots or something.” And he looked at me and I thought, “Oh, my God, are you going to fire me now?” And he started laughing. He’s like, “Haw, haw, haw, that’s genius.” And I’m like, “Yeah, Babylon was. Gotta go.”

And then when he started sexually harassing this woman I was friends with, that was enough of it. I’d seen him do it to her. And it really devastated her. This was pre–Anita Hill. It was way before anybody had any knowledge of what this was or reacted to it in an intelligent way. Everybody behaved like fools. So eventually I quit.

I’ve told this story before, but years later I ran into him, and he said, “Most people in this town stab you in the back, but you stabbed me in the front, and I appreciate that.” I said, “Anytime, you son of a bitch.” It was a great moment. I’m so glad he’s dead. Seriously, I’m glad he’s dead. He was a jackass. He deserved it.

After that, I had some great bosses at the Washington Post. I’ve mostly had male mentors and bosses, for some reason. There was Peter Behr, who gave me a chance when I wasn’t anybody. I remember a lot of women were on maternity leave and let me do their beats for them, which was a big deal. And David Ignatius, who was really good at inspiring people to want to do things for him. Same thing with Ben Bradlee, who would come over to me and be like, “What do ya got, kid?” And I’d be like, “Whatever you want, sir!” I wanted to write for those guys. I wanted to please them. And I’ve never been much of a man pleaser.

Then I went to the Wall Street Journal where Paul Steiger hired me, and he was wonderful. But the most important mentor I’ve had was Walt Mossberg. He’s the one who got me to go to the Wall Street Journal from the Post. He believed in me the most. He gave me a million chances. He took me in when he was at maximum power and really used his firepower to show people who I was.

Then I became a boss myself. When I started AllThingsD with Walt, I was the day-to-day boss of the site. I think people liked working for me. I think I was super straightforward and honest. I think I was probably too transparent in some cases. I’d say, “This is the mess we’re in, the Journal is driving us crazy, we hate Rupert.” I wanted my employees to know what exactly was happening with the company, and I don’t necessarily think that’s always the best idea now.

The bosses who have been the most effective for me, personally, are the ones who are forthright and clear. And I’m that way too. Sometimes reporters would come to me and say, “This is what’s happening.” I’d be like, “Are you a sucky reporter? That’s not what’s happening. Why are you guessing? Just ask me.” I had one employee I used to challenge. I once said, for example, “We need to find out who is joining the board of Twitter.” And he wasn’t moving fast enough, so I said, “One of us is going to get this scoop, and if I get it, I’m going to put it under my name.” In this case, I think it was good for the guy. He kind of liked it. It was a challenge. It was sort of a “snatch the pebble from my hand” situation.

I think people who are sensitive probably don’t do as well with me. But I’m not a rude person. It’s never personal. I like independent people. I like people with a point of view. I like people who disagree with me. Though, if I were managing my own 22-year-old self right now, I’d probably fire me.

Over time I’ve realized I don’t really like being a boss. I remember teaching journalism and thinking, “Well, I figured it out, why shouldn’t you?” I kind of feel like I was raised by wolves in my career, at least early on, and I turned out fine. I’m best as a solo operator. Management is exhausting. People are emotional, people have issues. And I’m ultimately too selfish for that. I’m more interested in my work than anybody else’s work. It might sound rude or crazy, but I just think I’m better. And women aren’t supposed to say that. Historically, a lot of women have had to help the men in charge. They were always No. 2. I want to be No. 1.