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Fortune Magazine Senior Editor Shares Leadership Insights with WSB

By Marguerite Darlington

December 2, 2015

Powerful CEOs might be tempted to underestimate Jennifer Reingold, but that would be a mistake. She’s a tenacious reporter and one of the most powerful business journalists in the U.S.—a senior editor at Fortune magazine who has published in-depth articles about leadership for more than 20 years.

Business Writer in Residence, Jennifer Reingold listens as CEO/Founder Kelda Roys of OpenHOuse, Inc., talks about her startup company during Jennifer visit with the Weinert Center for Entrepreneurship on Wednesday, November 18.
Jennifer Reingold, Senior Editor at Fortune magazine

“I write about good CEOs and bad CEOs,” Reingold says, concisely explaining the focus on leadership and management throughout her career at national publications such as Bloomberg Businessweek, Fast Company, and Fortune magazine.

“Being a good leader is really about the intangibles,” Reingold told Wisconsin School of Business faculty, students, and staff who came to see her speak as part of the School’s Business Writer in Residence program in November. “The best leader isn’t always the loudest, and the best CEOs are more focused on their organizations than themselves.”

Reingold shared unparalleled insights about top executives whom she’s met and observed over the years, including Steve Jobs (Apple), Ron Johnson (JCPenney), Frank Blake (Home Depot), Elizabeth Holmes (Theranos), and Travis Kalanick (Uber).

“To successfully lead a company, you have to understand where you want to go and where you can go,” Reingold says, explaining why Johnson’s efforts to rebrand JCPenney fell short. “When Ron Johnson tried to change JCPenney, he fired his current customers and went after a new customer base. The problem was, the new customers didn’t want to shop at JCPenney, and the old customers didn’t want to shop at the new JCPenney because of the way the brand had changed.”

Jennifer Reingold and Page Moreau listen as Mike Judge speaks.
Mike Judge (L), director of the Center for Brand and Product Management at the Wisconsin School of Business, and Page Moreau, academic director of the Center and John R. Nevin Chair in Marketing, discuss marketing trends with Reingold (R).

In addition to sharing insights about industry leaders, Reingold took the time to answer questions from WSB faculty, students, and staff.

WSB: What are the most important challenges facing executives in the next 10-20 years?

JR: Speed and disruption are challenges that everyone is facing. The speed at which change happens is exponentially increasing, and I don’t think that there’s anyone in leadership that has a handle on how to deal with every new technology change that’s coming down the pike. And there are broader issues that are important, like cyber security. I think the entire nature of the workforce is changing, the flexible economy is huge, and it’s going to affect everyone. Maybe companies will stop being the place that people get their health care. The form of the corporation could change fundamentally.

WSB: You mean companies becoming more like distribution centers that treat employees as entrepreneurs or independent contractors?

JR: If you look at it from a cost perspective, that sounds really appealing because they don’t have to pay for benefits or health care or office space, but then you have much less control of your employees and you don’t always necessarily want that. There are quality implications, and management implications. You want everyone to grow in the same direction, but under a decentralized model, no one is interacting with each other.

Ashleigh Coaxum speaks as people around her listen.
Ashleigh Coaxum, MBA (2016), shares her thoughts during the MBA President Council meeting when students had the opportunity to discuss leadership issues and management challenges with Reingold.

WSB: Is there a difference in the way female leaders are covered in the media?

JR: There is. Female executives—especially young, beautiful female executives—are often placed on a pedestal. You can see this even at our publication, the way that we placed up-and-coming Elizabeth Holmes on our cover. Her company grew very quickly, and, now that her company is in trouble, you can see that when female leaders fail, they are taken down more severely in the media.

WSB: What skills do you think MBA students need to master before managing others in the workforce?

JR: They need to be more self-aware. It’s really important to understand your own strengths and weaknesses and how they play in an organization. It’s really cool what you’re doing here at Wisconsin with the StrengthsFinder work.

Business Writer in Residence, Jennifer Reingold, jots down some notes as Joan Schmit, professor and department chair of actuarial science, risk management and insurance, talks about the new discoveries within her field during their one-on-one with each other on Wednesday, November 18.

Students come out into the real world and think that they have it all figured out because they’ve got all their numbers, but the real world is complicated and messy. I also think there is a disconnect between millennials’ career approaches and what people should expect from their bosses. Their sense of time is very compressed and they want extra mentoring and help, and it’s understandable why they want that because of their careers, but it’s not always very practical.

WSB: What do you think the biggest challenge is for business schools that are training future leaders? 

JR: Managing and dealing with uncertainty. And I don’t know how you train this, but somehow inculcating the values of flexibility and responsiveness—if there were a way to prepare people for the fact that things are going to change. Take this week, what’s happened in the world. If you’re an MBA student trying to get a job, maybe that internship in Paris isn’t going to happen. Maybe because of these events, someone will get a job doing analytics at the TSA. And the global economy is going to change again and again.

Those of us from an earlier generation believed that things would be more or less the same, and I think now… take social media. You go to work for Procter and Gamble, and the next day someone finds a rat in your product—or pretends to—and puts it all over social media and then you as a brand manager, it’s not your fault, but you have to deal with that. Things are not under your control the way that they were. Or maybe they never were, and it’s just an illusion.

Business Writer in Residence, Jennifer Reingold listens as Co-founder and Chief Scientific Officer Jordan Sand of Loacsys LLC, talks about his startup company during Jennifer visit with the Weinert Center for Entrepreneurship on Wednesday, November 18.

WSB: I wonder what implications might be for education.

JR: I think it’s relevant to any field, really.

WSB: Does that mean that one degree and you’re done doesn’t fit any more? You recently did a piece on the massive disruption in higher education.

Generally speaking, higher education is in big trouble. I don’t think the whole system is going to collapse any time soon, but there’s a really big mismatch between what people are paying for the university experience and what they’re getting. Then there’s the technological piece—are you getting as good an experience online as you would if you attended full-time? No, but maybe you’re getting 80 percent as good an experience for 20 percent the price or even 10 percent the price. And maybe that causes people to make a different calculation.

I think that the Wisconsin School of Business is in a good place. I was impressed by your dean—he breaks the mold. He’s motivated and dynamic and wants to change to adapt to new challenges.


Since 1989, the bi-annual Business Writer in Residence program at the Wisconsin School of Business has brought a national journalist to campus to meet with the WSB community, share expertise, and connect with the latest research and educational trends. Past business writers have come from publications such as The Wall Street Journal, Washington Post, USA Today, Forbes, and Fast Company.