Page 20 - Demo CEOs of the Fortune 500

• According to a 2016 Wharton Magazine profile of Crandall, "Because he was already a Chartered Financial Analyst (CFA), Crandall decided to focus on leadership and strategy during his time at Wharton. One of several faculty members who most influenced his thinking was leadership expert Michael Useem, the School’s William and Jacalyn Egan Professor. In the break between the end of classes and graduation, Crandall participated in one of Useem’s leadership treks—a 90-mile hike to the base of India’s Mount Kangchenjunga. At every lunch and dinner break, a different student led a discussion about leadership. He remembers having a conversation with Useem about ethics—and how important it is to operate with a sense of integrity. 'This is one of the areas where Wharton has helped to lead the way in the business community,' Crandall says. 'They step back and think about things like that.' Ethics scandals seem to sweep through the business world every few years, but for Crandall there’s nothing cyclical about character. 'Either you are going to approach life and approach business [ethically] or you won’t,' he says. 'It’s not a ‘sometimes you do and sometimes you don’t’ sort of thing.'"
• He has a laminated card on his office conference table that reads: "When you are safe, think of danger," in both English and Chinese. "When I’m having a meeting here and someone starts to get too optimistic, I can just hand them the card," Crandall said.
• In the early 1990s as a MassMutual analyst, Crandall recommended investment in Morris Air, a startup airline in Salt Lake City, despite the fact that such a recommendation could jeopardize his career due to the industry’s high failure rate. Thankfully, MassMutual’s $5 million investment in Morris Air’s convertible preferred shares tripled in four years. Morris Air co-founder David Neeleman later started another airline called JetBlue Airways and MassMutual became an original private equity investor in it, owning nearly 7% before its IPO in 2002.
• Crandall’s uncle, Robert Crandall, who ran American Airlines from 1985 to 1998, said of his nephew,, "Roger would call me from time to time about airlines and aviation, and I’d help him out if I could. But he’s obviously very good at analyzing companies.”
• Crandall said that he wants to run MassMutual Financial Group the same way Wayne Gretzky played hockey. Gretzky, "The Great One," skated toward the place where he thought the puck was going instead of chasing it. His great anticipation helped him break nearly every scoring record in the National Hockey League. In the same way, Crandall hopes to anticipate trends that evolve over decades to put MassMutual in a good position for the future.
• Crandall recalls about his early career, "I fully intended to work on Wall Street, but the market crashed in October of 1987 and there were no jobs on Wall Street. I planned to stay at MassMutual for a year or two before going back to New York City and working at an investment bank or a private equity firm. I stayed because I got a chance to do interesting work, the people I worked with were great, and the Springfield region is a great place to raise a family. In hindsight, it was a great decision.”
• Crandall said, "I’m a huge fan of slow and steady growth.”
• “Throughout your whole career you have a boss, but when you become a CEO, you suddenly have a board with a dozen bosses,” Crandall said during a 2014 interview on Sirius XM radio show “Leadership in Action.” He continued, “That came as a bit of a shock. That’s a very real-world challenge for any president and CEO. I did two things that paid great dividends. First, I talked to all the living, retired CEOS about the company and challenges they faced. I also met with some new CEOs of companies in different industries and asked what their biggest challenges were when they became CEO. That was valuable and reinforced the need to have a team to depend on and trust.”
• Crandall lives in Somers, Connecticut, with his wife, Gabrielle, and their sons, Thomas and Brian.
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