When Peter Grauer’s daughter was six, she sweet-talked him into taking horseback riding lessons in New York’s Westchester County, where the family lived. Grauer didn’t mind, because it gave him a good opportunity to have some Saturday morning bonding time with her.

At the corral, Grauer met a congenial man who also had a young girl taking lessons. The two struck up a friendship as they waited through their daughters’ sessions. “Our daughters became inseparable, and we were happy about that,” Grauer recalled during a speech at the 2013 Wharton Leadership Conference, noting the other man had started a business that had just become successful when the pair met in 1989. “One of us would bring the bagels and the other the coffee. We would talk about business and sports and families, the usual stuff.”

Then one day, when the girls were in their teens, the other dad decided to go into politics and wanted to cast off his CEO job. “It was Christmas of 2001 and he asked me, even though I had never worked in the media, to be his [company’s] CEO,” said Grauer of his Saturday morning stable buddy, Michael Bloomberg. “I tell people that you never know where you will make your connection. I was fortunate, and I have had a wonderful time. I run one of the most successful U.S. companies, and I owe it all to my daughter’s desire to ride horses.”

In truth, Grauer was qualified to take the job at global media company Bloomberg LP, having worked in high-level executive positions for Bank of America and Donaldson, Lufkin & Jenrette. According to Grauer, leadership cannot be boiled down to one or two attributes, and, even if it could, those attributes would necessarily seem a bit contradictory. At Bloomberg, he noted, when his executives go on one of their frequent retreats, they always come to the conclusion that the best leaders are those who exemplify a line from Walt Whitman’s “Song of Myself”: “Do I contradict myself? … I am large, I contain multitudes.”

“Instead of just being the best big-picture thinker, someone may be the best at that and also detail oriented,” said Grauer. “They can give direction on little things and also encourage big ideas. They can be loyal to our company and also put the customer first. We call it the ‘and factor,’ and at Bloomberg we consider it the definition of leadership qualities.”

Grauer does not rule out anyone becoming a leader based solely on his or her background. In fact, he said, his early years would certainly not be inspiring on a resume. At 15, he considered life to be a series of three things — sports, girls and fun — “I was pretty good at the first and last, not so much the middle one,” he joked.

Eventually, Grauer realized that he needed to change his focus. He convinced his parents to send him to boarding school for a chance at a fresh start. Grauer enrolled at The Hotchkiss School and went from being a “C” student to president of the student body and captain of the football team. But before he achieved those honors, school officials would only admit him if he repeated the 10th grade.

“No one wants to repeat a grade in high school, but I knew I had to do it,” Grauer noted, adding that he was lucky to get the opportunity to change course. He ended up going to the University of North Carolina. Grauer is constantly awed by the Harvard, Princeton and Yale types Bloomberg often hires, he said, but the large state-school environment was what he needed. He learned to negotiate big crowds and home in on what he wanted.

Grauer graduated from UNC in 1968 and the Harvard University Graduate School of Business Program for Management Development in 1975. “Life is a lot of being in the moment, saying, ‘How am I going to get out of here?'” he said. “God knows where my maturity eventually came from.”

Induce and Reflect

It is important, Grauer noted, for a leader to assert himself or herself, but even more vital is to have a good streak of humility. “When I started my career, I had that Wall Street swagger. I certainly thought I was the smartest guy in the room,” he recalled. “Then in 1984, a miraculous thing happened: I had a deal that turned into a big fiasco.

“At that stage of my career, I lost whatever I had [in terms of] a reputation for being a deal maker,” Grauer said. “After it fell apart, I took a hard look at my skills. From that moment on, my approach was that I would take on every challenge with humility. I would never be too proud to ask for help. At Bloomberg, we call that ‘constructive paranoia.’ We are constantly preparing for someone smarter than us to take us on. I love the idea that people at our company do not think they are as good as they really are.”

Grauer’s talk at Wharton was titled, “The ‘And’ Factor: Embracing Contradictions to Develop Great Leaders.” One of his “and” criteria is that a leader should have the ability to both induce action and stand back and reflect. For example, while running Microsoft, Bill Gates would often travel to a remote place and take only some articles he had put off reading, Grauer noted. Gates’s only interruption would be that he would have someone bring out meals; otherwise, he would spend his time reading and jotting down ideas. “Some would lead to a new product or a project for his foundation. Others would be small and fleeting. But each one would give him more perspective. We need to take time to step back from the day-to-day and be alone with our thoughts.”

According to Grauer, the ability to reflect is a key skill he tries to instill in executives during Bloomberg retreats, particularly in the case of younger employees who may not have learned to value it yet. “I have asked them to spend time outside of work with a clear sheet of paper and make brutal self-assessments,” he noted. “They can choose to share them with me or not, but most have. It set a framework for them about their strengths and weaknesses going forward. I believe that a career is a long reflection [on] self-improvement.”

Above all other qualities, Grauer said, a leader must establish a sense of intimacy with employees and customers. He or she must, as best as possible, learn something about every employee and relate to them on a personal level, because a leader can never be sure what trait will make an employee a future leader. His own first big interview brought that point home to him. “The head of college recruiting at Citibank took a chance on me at my first big job,” he noted. “I was woefully under-qualified. On that first day, there were MBAs from Harvard, Wharton and Columbia, but someone took a chance on something I had said or done — [something] that maybe I didn’t know I could do well myself.

When I address a group, I try to look everyone in the eye and shake hands,” Grauer continued. “I want them to know they are important to me. At some moment in the future, I am going to ask people to do something hard…. They will walk over hot coals for a leader who they believe has their interests in [mind].”

Working without a Playbook

Prior to joining Bloomberg, Grauer was a managing partner at Donaldson, Lufkin & Jenrette from 1992-2000. He served as managing director and senior partner of CSFB Private Equity until March 2002, when he joined Bloomberg full-time. Grauer had been a member of the media and financial data company’s board since 1996 and has served as its chairman since 2001.

Co-founded in 1982 by New York Mayor Bloomberg, the media company, which provides financial analytics and data through the eponymous Bloomberg Terminal, has grown to more than 15,000 employees in 192 locations across the globe. The privately held firm generated $7.9 billion in revenue in 2012, up from $7.6 billion in 2011, according to Forbes.

During Grauer’s tenure, Bloomberg completed acquisitions of BusinessWeek and the Bureau of National Affairs. Last May, the company purchased Dublin-based software firm PolarLake in an effort to launch a new data management service.

While speaking at Wharton, Grauer recalled a trip to Japan that he took soon after the devastating earthquake and tsunami in 2011. He had business to do, but realized that circumstances also made it an opportunity to show leadership through intimacy. “I arrived at 6 a.m., and Narita Airport [in Tokyo] was deserted. The roads were empty when we made our way to the office. It was pretty scary,” Grauer noted. “When we arrived at our offices, the building was still shaking with aftershocks.”

But, to Grauer’s amazement, nearly all of the employees were in the office working. They came, he noted, because it was important to them to check in on colleagues, and to feel a sense of normalcy. “I stopped at every desk, shook hands and told them how important they were to us,” said Grauer. “I told them that as a company, we would never leave Japan. There are a lot of moments in one’s career where there is no playbook. But when you approach it with humanity, the rest will work.”