Even the boss has to worry about fitting in at a new workplace.

Jack Griffin, who started Monday as chief executive of Tribune Co. TRBAA +0.13% ‘s newspaper publishing division, expects to get along better than he did at his last corporate position. He was fired in February 2011 after less than six months as CEO of Time Inc., where he aggressively pressed for change. His leadership style “did not mesh” with the Time Warner Inc. TWX +0.73% unit, the company said then.

Paving the way for his new role, Mr. Griffin and colleagues at his publishing-industry consultancy have for the past year advised Tribune about the strategic, operational and organizational issues it faces. After deciding to spin off its newspaper division, the company chose him to lead the unit because he offered “vision and expertise,” Tribune said.

For Mr. Griffin, joining Tribune “was the right thing and a good fit,” said a person familiar with his thinking.

A poor cultural fit is the primary reason top managers fail, according to executive coaches and recruiters. But there is no perfect way to predict a match. So in addition to the traditional rounds of interviews, networking with prior staffers and review of analysts’ reports, senior-management applicants are now being urged to play the role of corporate anthropologist to gauge their compatibility with potential employers—from quizzing future subordinates to dining repeatedly with the boss-to-be.

“Most executive hires that don’t work out are due to inadequate diligence by the recruit and employer,” said Joanna Starek, a senior partner at RHR International LLP, a leadership-development firm. “The costs for getting that wrong are incredibly high.”

Just ask Yahoo Inc. YHOO +5.48%

Henrique de Castro lost his job in January—and got an enormous golden parachute—after just a year as chief operating officer of Yahoo, where he reportedly clashed with CEO Marissa Mayer. “Ultimately, Henrique was not a fit,” declared Ms. Mayer following his dismissal.

Mr. de Castro—who was hired from Google Inc., where Ms. Mayer previously worked—walked away with about $109 million in compensation, including his salary, hiring bonus and a severance package worth more than $64 million, according to the estimate of executive pay researcher Equilar

Mr. de Castro couldn’t be reached for comment.

Amid an improved job market, more executives appear poised to jump ship. About 56% of executives are considering an exit within 12 months, up from 45% in 2013, concludes a 2014 survey by ExecuNet, a business and career network.

They would be well advised to look harder before they leap, leadership specialists say.

Mr. Griffin assumed he had a mandate to change Time, he told Crain’s Chicago Business after his ouster. The parent company’s lack of interest in dramatic changes “was a disconnect from the beginning,” a senior Time Warner executive has said.

Employers rarely give executive applicants access to their likely subordinates. Mr. Griffin, for instance, spoke with only a few Time staffers during its highly confidential search—partly because he worked for rival magazine publisher Meredith Corp., according to the informed individual.

Raleigh Mayer, an executive coach, suggests that her clients arrive early for a management job interview and “look for every possible clue as to their culture,” she said. “Do people say hello in the bathroom? Is there interesting art on the walls?”

A cutting-edge art collection may demonstrate that a business encourages innovation, said Michael J. Anderson, head of leadership advisory services for recruiters Spencer Stuart. On the other hand, “the founder might just like art,” he continued. “Don’t overread the artifacts.”

Try to get some face time outside the office, where “people tend to let their guard down” said Stacey Lauren Musi, a managing director at recruiters Chadick Ellig Inc. “If they are barking at the maitre d’, that would tell you something about their management style.”

Spencer Stuart’s Mr. Anderson once agreed to be interviewed by the wife of a prospective executive so she could decide whether he would be a good boss for her spouse. The creative gambit impressed Mr. Anderson. But for unrelated reasons, he didn’t hire the candidate.

The finance chief of a high-tech company had several dinners with the CEO—and even accompanied him on a trip to its San Francisco office—before accepting the job in 2012.

“Executives have to understand [personal] values before they can know whether there will be a match with the company they are going into,” said Jeff Chartier, chief human resources officer of Sig Sauer Inc., a maker of small weapons.

Mr. Chartier took his own advice ahead of taking the newly created role in June 2012. “I valued an atmosphere where honesty, candor and a willingness to entertain and try new ideas would exist,” he recalled.

Before taking the job, he sought candid chats with eight of the CEO’s 12 lieutenants and four managers who would report to Mr. Chartier. The face-to-face sessions uncovered internal discord. His potential peers complained that the company didn’t attract enough top-quality talent, he said. Yet the HR managers “thought they were doing a good job.”

Mr. Chartier wasn’t turned off. In fact, he said he liked that “there was no trying to hide anything” at Sig Sauer. Plus, “I love a challenge,” he added.

From wsj.com

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