Careers rarely go according to plan. In Job Hacks, we shake down experts for the insights they cultivated on their way to the top of their field.

Name: Alan Murray

Original Home State: Tennessee

Job: Alan Murray is the editor of Fortune magazine. Previously, he served as the deputy managing editor and executive editor, online, of The Wall Street Journal, the president of Pew Research Center, CNBC’s Washington, D.C., bureau chief, and he co-hosted Capital Report with Alan Murray and Gloria Borger. He has also written several books, including Revolt in the Boardroom: The New Rules of Power in Corporate America, The Wealth of Choices: How the New Economy Puts Power in Your Hands and Money in Your Pocket, and Showdown at Gucci Gulch: Lawmakers, Lobbyists and the Unlikely Triumph of Tax Reform.

You’ve worked in all different forms of media: magazine, books, television. Which area do you find the most rewarding?

I’m really fundamentally a journalist. I started when I was nine years old, walking up and down the neighborhood street, asking people what was going on — how was their vacation? How is their pet? I’d write it up, put it all on a one-page news sheet, and sell it for a nickel. So I’ve been a writer and a journalist since before I was old enough to make an intelligent decision about my career. And I love it.

I spent three years hosting a television show and that was fun, but when it was over, it didn’t really feel like what I wanted to do with my life. I spent two years running the Pew Research Center. It’s a great place and has a lot of close ties with journalism. But when the opportunity came along to edit Fortune, I took it. I like to write about events.

You have to go in front of the camera quite a bit, and that doesn’t always come naturally to writers and journalists. Did you have to acclimate to it?

I love being in front of the camera, I spend a lot of my time interviewing people in front of audiences. I like all of that. It’s just that, even with an hour a day of television to play with, it’s remarkable how shallow TV journalism is. At the time I was doing the CNBC TV show, I was also writing a 750 word column every week for The Wall Street Journal. It just struck me how much deeper I could get into issues in my 750 word column than I could in my hour-long television show.

I almost had to train myself — if I was doing a TV interview and I started to get really interested in what the person was saying, that was a sign I needed to cut it off and move on to the next topic. The nature of live television is that you have to move quickly and keep it face-paced or you risk losing the viewing audience. Alternatives are just a click away.

Since you’ve done so many interviews, are there any in particular that stand out?

I would probably say the most interesting interview I’ve done recently was with Larry Page of Google. I’ve interviewed hundreds of CEOs of large companies and he’s so unlike any of them. He thinks about things in such a different way. A lot of CEOs are heavily media trained. Politicians as well. It’s always kind of hard as an interviewer to get people off of their talking points. I don’t think Larry Page had any talking points. He just tried to respond to my questions. You could see his brain working, and it was fascinating.

Alan Murray with Larry Page at the Fortune Global Forum 

At one point, I asked him, “In thinking about this corporate structure, were there other companies that you admired and wanted to model this company after?” And he stops for a second and looks in the air and he says, “Uh, no.” Just a flat no. There’s no other company I admire or want to model my company after.

Since you do interview a lot of CEOs and politicians, have you developed a strategy for cutting past talking points? Or is everyone different?

Everyone’s a little different, but there are two key parts for my strategy. One is that I don’t go in with a list of questions that I’m determined to follow. I have some general topics that I want to talk about, but I try and follow the flow of the conversation. So if you see an opening to get them off the talking points, you can take it.

Two is, you’ve got to be tough but also friendly. You have to be tough so you can get them off the talking points, but you have to also be friendly so they feel comfortable. I’ve worked very hard to create an interviewing style that is both tough and friendly.

What’s more challenging, interviewing politicians or CEOs?

Politics is always challenging because most people have pretty firm views. It’s the reason why they tell you, “If you want to have a nice dinner party, don’t bring up politics.” Things start to break down. It’s always hard to be tough in a political interview without looking like you’re taking a position.

So that gets back to the tough, but friendly. I guess going back to preparing, make sure you know your subject very well — so you do spend a lot of time preparing in the sense that you have to know what they’ve said in the past, so you know their openings to get them to say more. But don’t over-prepare on the questions you want to ask. You need to be flexible enough to follow the conversation.

And what would you say is the most challenging part of your job on a daily basis?

The most challenging part of media these days is the business model, which traditionally was based on advertising at a time when advertisers had to go through journalistic media to reach their audiences. In the digital world, they don’t have to do that anymore. They have lots of alternatives. So the traditional connection between advertising and journalism has broken down. That’s a big challenge that all of us face — how do we continue to support great journalism in an era when advertising isn’t providing the support it once did?

If you think about what happened to the music industry, once upon a time, artists made money by selling records. Then the digital world and the internet came along, and all of a sudden, people were ripping off songs for free. Yeah, iTunes was created, but it wasn’t a very lucrative model. Successful artists found that the only way they could make the money they were worth was by holding live events. So records have become marketing tools for live events, and live events are where people make their money.

Conferences are kind of like that for us. We make money from the magazine and the website, but we make a lot of money from the conferences. Some of it is advertisers, but a lot of it is, people pay a lot of money to attend our conferences.

In the advertising world, advertisers were supporting journalism not because they were consuming it but because it was a means to an end. It was how they got to their audiences. In most businesses, the people who pay or who are consuming the product are the service. But in media, it was the somewhat artificial relationship between advertisers and media. The digital world broke that down and gave advertisers lots of ways to reach the audiences they wanted. So now we have to recreate a world where the people who are actually consuming our services are willing to pay for it. Conferences are part of that, and we have to think of other ways to make that work.

Marc Andreessen, Sheryl Sandberg and Alan Murray at the Fortune Global Forum 

What’s the most surprising thing you’ve experienced at an interview or event?

It’s one of the main reasons we become journalists, right? You get to go to all these places and be in all these situations where you don’t belong. I remember in 1990, when the Berlin wall was falling and communism was crumbling, a bunch of cabinet members from the Bush administration went to Poland. They offered to take some journalists along, so I traveled with them. We were — I think mistakenly — led into the room where they first met Leszek Balcerowicz, who was the finance minister of Poland. They were trying to figure out a way to meld communism with capitalism and find some third way of doing things, and he basically said, “There is no third way, it’s over. Socialism lost, we are 100% behind a capitalist economy.” We were all in a state of shock, to hear the finance minister of Poland say that.

And to sit down and interview someone as smart and thoughtful and interesting as Bill Gates, or to have the opportunity to have met Nelson Mandela, who is one of my heroes — that’s part of what makes journalism so fun. I can’t say there was just one where I said to myself, “I can’t believe I’m here and doing this and talking to this person.” Every day, I say “I can’t believe I’m here, I can’t believe I’m doing this, and I can’t believe I’m talking to this person.”

What advice would you give to a journalist at the beginning of their career?

The advice I would give is threefold. One is there has never been a more interesting time to be in journalism because the tools of the digital world make your reach so great and the ways you can interact with your readers are so varied. Whether it’s video, or photos, or direct conversations over Twitter, or Google Hangouts. It’s never been more interesting than it is today.

Two, having said that, it’s not easy for me to say to a young person that I can clearly see how — 25 years from now when you have a family that you need to support and you’re trying to make a decent living — I can guarantee you’ll be able to do that as a journalist. So you’ve got to think about the economics model.

Then the third piece is related to the first two: I think the way you deal with that is to try it all. Learn about it all, make sure you’ve developed skills in as many different kinds of journalism as you can, and always have a mind that’s open to trying new things and experimentation.

I didn’t study journalism at UNC. I thought about it and took a few classes and thought, “this is a waste of time; there’s nothing in a class I can learn about journalism.” For many years after I graduated, I would tell people, “don’t major in journalism.” But I think that’s totally changed. I think now we’re so desperate for the skills that you need to conquer digital media. Do you know how to make a video? Do you know how to edit a video? Do you have some knowledge of writing code? You want to be able to know what the possibilities are and not be at the mercy of coders. Do you understand social media and how you build an audience and the ways to maximize your audience? There’s this whole set of new skills that didn’t exist when I came out of school.

Which set of new skills presented the largest adjustment for you?

In general, for journalists of my generation, I think the single biggest adjustment has been social media — because we thought of ourselves as artists, basically. We would create beautiful pieces of journalism and then it was somebody else’s job to get that to the audience. You almost thought that it was dirty if you got involved in the promotion of your journalism. Like, “I’m not going to pimp my own stuff, that’s the circulation department. All I have to do is create great journalism.”

What social media has done is made journalists realize you’re responsible for building your own audience. That was so foreign to the culture that existed 20 years ago. It really takes a lot of getting used to. A lot of people haven’t gotten used to it.

What publications do you read when you have time?

I still read The Wall Street Journal every day. I read The New York Times pretty regularly. I rely a lot on my Twitter, on the people I follow to point me to interesting stories that are going on. I read a lot of magazines now. “Read” is probably the wrong word. I look. I take a big stack of magazines home every Friday and spend my weekend flipping through them.

Some of it is just understand popular culture. It’s important as a journalist to have some understanding of what’s going on in popular culture.

What do you follow in pop culture? Any TV shows?

These days my favorite TV series is Mr. Robot. I follow Homeland closely, Downton Abbey. Breaking Bad I thought was one of the best pieces of television I’ve ever seen.

It’s become a cliche at this point to say “print is dead,” but what are your thoughts on its future?

I think print is getting old and will probably die someday. It doesn’t really make sense to cut down trees and chop them up; to deliver content when you can create a form that’s just like a magazine or newspaper but is all digital. It saves the trees and saves all the people driving around in your neighborhood at 4:00 in the morning to deliver it. I think it will eventually die, but it’s going to be a long, long time. People love their newspapers and people love their magazines. I suspect in 20 years from now, they’ll still be around.

Photos via Getty / Kimberly White