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A Lawyer’s Path from Prosecutor to Fortune 100 CEO

By Lori Atherton
November 7, 2017

Amtrak President and Co-CEO Richard H. Anderson has spent the majority of his career in high-profile business roles, including serving as CEO of Delta Air Lines and Northwest Airlines. But being a lawyer, Anderson said, makes him “eternally proud.”

“I think a law degree is, by far, the best graduate degree you can get,” Anderson told Michigan Law students during an October 27 visit. “Think about what you learn: You learn to speak well, think critically, and write well. From a professional standpoint, being a lawyer is one of the most intellectually satisfying career paths, because it enables you to have a deep curiosity about so many things.”

Anderson, who still carries his Texas Bar card in his wallet, shared career insights with attendees during the discussion, “A Lawyer’s Path from Prosecutor to Fortune 100 CEO,” which was moderated by Ramji Kaul, ’05, Michigan Law’s assistant dean for career planning. The event also was attended by U-M Regent Andrea Fischer Newman.

A graduate of South Texas College of Law, Anderson started his career as a prosecutor in the Harris County, Texas, District Attorney’s Office before moving to the legal division at Continental Airlines. He served as CEO of Northwest Airlines (which later merged with Delta) from 2001 to 2004, and was executive vice president at United Healthcare from 2004 to 2007. He most recently was the executive chairman of the Delta Air Lines board of directors after serving as the airline’s CEO from 2007 to 2016. Anderson began his current role at Amtrak—a volunteer position in which he does not receive a salary—in June.

“It’s really up to you what path you want to take, no matter if you graduate from Michigan Law or South Texas College of Law,” Anderson said. Noting that he didn’t attend a prestigious law school, Anderson urged students to take advantage of the endless opportunities that Michigan offers. “This institution is so incredible in terms of what it wants to give you,” Anderson said. “You never know where some connection or opportunity will come from, so take advantage of your professors’ office hours and go to all your lectures.”

Anderson said his leap from lawyer to business executive wasn’t intentional and that he didn’t have an overarching view of how he wanted his career to progress. “I never had any aspirations to be CEO. I just ended up being one,” he said. “I was a trial lawyer, an appellate lawyer, and then a general counsel. I made all the moves because I had to be practical about earning money to pay back my student loans, and because I was married and had kids.

“I didn’t go to Harvard, so I had to make it up by being the most prepared, being at the meeting first, and always volunteering for projects,” he added. “Pretty soon everyone at Continental came to my office, because I always tried to figure out how to legally get them to their objective.”

As a junior lawyer at Continental in 1987, Anderson volunteered to attend a weeklong accident investigation seminar in Montreal. Six months later, a Continental flight crashed while taking off in a snowstorm in Denver. “I was the person who got sent to the accident,” Anderson said. “As a result of being involved in that accident, I learned an enormous amount about how airlines run, how airplanes work, and how the regulatory structure develops in an airline. It was one of those serendipitous events that ended up teaching me about the airline industry.”

Anderson credits the people he’s worked with for helping him acclimate to the world of business. “I had the great fortune of working around good people who understood business and were commercially oriented,” he said. “When you see people from whom you can learn, learn from them. At some point your instincts will take over about what you need to do to be a good trial lawyer or to make a business run well.”

Whether running a business or being a lawyer, it’s important to provide steady leadership, especially in difficult times, Anderson said. “You can’t ever let on in a courtroom that somebody got you. You can’t grimace when there is bad testimony against your position. You’ve got to keep that poker face,” he said. “When you are a lawyer and a client comes to you with a serious problem, they need assurance from you that it’s going to be managed well. Maybe the outcome isn’t what they want, but there is no substitute for cool, steady, straight-ahead leadership. When you run a big company, you’re going to get bad news every day, and you have to be ready for that email that you don’t want to read. I wasn’t CEO for very long when 9/11 happened, and it set into motion a lot of serious things that had to be done, but people expected them to be done. As a lawyer, your client expects you to provide leadership, because they have a serious problem and they need a steady hand.”

Avid curiosity and a willingness to make mistakes are part and parcel of taking professional risks, Anderson noted. “Don’t be afraid to swing for the misses now and then. You’re going to make mistakes, but once you recognize they’ve been made, fix them and reverse course.”

And when feelings of self-doubt surface, regardless of the job, Anderson said it’s imperative to “figure out your own ways of coping with feelings of inadequacy. Figure out where those outlets and those places are that give you some solace from that. Most important for me were and are the relationships with the people I was in the trenches with. Find those people, relationships, and outside interests that can give you encouragement and help.”

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