When New York City mayor Michael Bloomberg named Joel Klein as chancellor of the city’s public schools in 2002, Klein was a publishing executive best known for leading the prosecution of Microsoft as assistant attorney general in charge of the Antitrust Division. While some criticized Klein’s lack of education experience, Bloomberg, himself recently elected mayor after a long career in the private sector, argued that Klein’s leadership skills could be transferred into an unfamiliar role.

"Running one of the Justice Department's most successful divisions as well as a major media company has given him the extensive and wide-ranging management experience necessary to turn our schools around," Bloomberg said in a press release. "He knows how to run a large organization, from picking the best people, to balancing large budgets, and making sure everyone is accountable."

When Klein stepped down as chancellor after eight years, observers differed on their views of the reforms he championed as chancellor, which included an emphasis on testing, greater accountability for teachers and schools, and a move toward charter and other small schools. But there was agreement that, as promised, he had brought the organizational ability to change a huge, complex, and slow-moving system. "Mr. Klein did deliver on a central promise," the Times wrote. "To challenge orthodoxies, shape up the status quo, and risk dislike in the name of progress."

Klein—who recently crossed back to the private sector, taking the role of CEO at News Corporation's education division, Amplify—could be seen as a living test case of the question of whether leadership skills are portable or specific to a job, industry, or sector. The question has been debated among scholars. Yale's Victor Vroom, for example, has found that leadership styles—the degree to which a leader consults with subordinates before making a decision, for example—are a function of the situation much more than the leader's personal qualities. In an epistolary exchange with scholar Robert Sternberg, now of Cornell University, in 2002, Vroom wrote, "I stand by a statement that I made over a quarter of a century ago that it makes more sense to talk about autocratic situations than autocratic managers."

In the same exchange, Sternberg agreed that context matters but argued for the importance of individual differences—among them the ability to transfer "tacit knowledge" from one situation to another. "Many a leader has failed because the leadership skills he or she brought from one organization did not transfer successfully to another organization," he wrote. "How much transfer there will be of tacit knowledge from one situation to another will depend upon the similarity of the situations and also upon the flexibility of the individual in adapting his or her tacit knowledge to fit the demands of new situations as they arise."

In a conversation with Yale Insights, Klein said that with his move from the New York City schools to Amplify, the stakeholders and the scale had changed, but his outlook on leading an organization had not. "If you don't have a strong team to make sure your message is being driven through the organization, it's not going to matter" how good your ideas are, he said. A key skill for a leader, he said, is to spend time productively. "I always tell leaders, 'There's just so much time; think about it and look hard at what you're doing with yours.'"