Sometimes, says Kevin Kelly, the best way to get a person’s attention is with a handwritten letter. Mr. Kelly would know.

As Asia-Pacific managing partner for the American executive-recruiting firm Heidrick & Struggles International, Mr. Kelly often finds himself trolling for local talent in a region where the practice of corporate recruiting is still widely unknown. As a result, he has trouble getting potential hires to return his calls. So he keeps a set of cards with his name and the name of his company printed on them, and when he finds someone he’s interested in recruiting, he dashes off a quick, handwritten note. “It’s more personal and it shows you’re serious,” Mr. Kelly says. “They always get back to me.”

Mr. Kelly, who is based in Tokyo, spends a good chunk of his time helping Western firms find local executives for their operations in Japan, where job-hopping has traditionally been taboo. This, says Mr. Kelly, presents some unique challenges.

Until recently, Japanese corporations promised lifetime employment and employees reciprocated with lifelong loyalty. But that idea began to crumble in the late 1990s when Japan’s prolonged economic downturn forced companies to lay off midcareer workers. Even so, says Mr. Kelly, many of the old reservations about leaving one’s company remain, especially among top-level managers who’ve been at one firm for a long time.

As a result, even if Japanese managers accept a new job, Mr. Kelly often has trouble getting them to resign from their old ones. A common scenario is this: Someone is offered a job, but when he goes in to tell his boss that he wants to quit, the boss says no. The response of many Japanese, Mr. Kelly says, is simply to accept the rejection and stay put.

Mr. Kelly addresses the problem by role-playing with his recruits. He meets them over breakfast and goes through the motions of quitting a job. In doing so, he helps them come up with a response to use if the resignation is rejected. “It mentally prepares them,” Mr. Kelly says. He also coaches the Western firms doing the hiring, preparing them for the possibility that their new hire may not be able to resign the first time around. “When you tell a Western company that the boss didn’t accept the resignation and the guy went back to work, they don’t understand,” Mr. Kelly says. Western firms tend to view this as a sign that the person doesn’t really want the job. That’s not true, says Mr. Kelly. “It’s cultural.”

All this may get easier. Attitudes toward executive job-hopping in Japan are changing quickly, thanks in part to some recent high-profile departures. One example is Shiro Tsuda’s decision last autumn to leave his high-ranking post at NTT DoCoMo, Japan’s largest cellular operator, to take the helm of the Japan operations of Vodafone Group. Mr. Tsuda’s move shocked the Japanese business world not only because he left his company but because he went to a direct rival, something practically unheard of in Tokyo.

Mr. Kelly says that in the past year he’s seen an increase in the number of senior-level Japanese managers looking to make a move, and often it’s to a foreign-owned company. In addition, Japanese, Korean, and Chinese companies are doing more outside hiring. In Asia, “you’re going to start seeing individuals move from one organization to another,” Mr. Kelly says. “To compete globally, companies have to have the best management that they can in place, bringing in fresh ideas and new management styles.”

For Western firms in Asia looking to hire top management locally, Mr. Kelly has this advice: First, look for people with good communication skills and be sure not to “confuse English-language ability with actual ability.” The most common problem for Western firms with a local CEO is poor communication with corporate headquarters. Often, this results in an Asian business that takes off in a vastly different direction compared with the rest of the company, he says.

In an ideal world, firms would cultivate their own top management, Mr. Kelly says. Foreign companies operating in Asia, for instance, would be well served by sending young local hires abroad early in their careers. When they return to Asia, the company will have “a bench of executives who can take over senior-level responsibility.” The trouble is, he says, most companies tend not to think that far ahead. “Firms don’t focus on a succession plan, which is why we’re in business.”