For a business leader like David Heenan — a trustee of the James Campbell Estate — the question of when to stay and when to leave a high-profile position has been a constant throughout his varied career, which includes posts as chairman and CEO of Theo. H. Davies & Co. and dean of the University of Hawaii’s business school.

Heenan has authored several books and his newest, "Leaving on Top: Graceful Exits for Leaders," offers advice on "how and when to call it quits" with your reputation intact. He sees it as a natural sequel to his 2002 book "Double Lives: Crafting Your Life of Work & Passion for Untold Success," which encourages people to develop a second skill set to lead a more interesting life and be more interesting to those around them.

In his own experience, Heenan, now a visiting professor at Georgetown University in Washington, D.C., said he’s always found it wise "to ‘re-pot’ every five to seven years for new horizons."

Although not mentioned in "Leaving on Top," Heenan said he was impressed with such local high-profile transitions as those that have taken place when top executives left their posts at Bank of Hawaii and First Hawaiian Bank. "Former UH President David McClain made a graceful exit as did, earlier, my good friend, former UH football coach Dick Tomey," he said.

Heenan responded via email to questions posed by the Star-Advertiser:

Question: Have you ever experienced a bad or unsatisfactory exit strategy yourself?

Answer: Not really. I’ve been very fortunate to leave — the Marines, academia, business — for positive, not negative, reasons, and typically for better opportunities with greater challenges.

Q: How do you deal with the risks of leaving?

A: Confronting the next chapter of life can be scary but invigorating. Most successful people are undaunted risk-takers. They don’t fear change, they are invigorated by it. Former Dallas Cowboys quarterback Roger Staubach, for instance, jettisoned a career in sports for a highly successful career in real estate. People like him understand the value of taking risks, of changing skins, and moving in new and exciting directions.

Q: Is there a particular time in a leader’s career to start making a graceful exit plan?

A: We live in a "free-agent workforce" where, like it or not, loyalty by both employer and employee is declining. Therefore, it makes good sense for everyone — irrespective of age or position — to have an exit strategy, a "what-if" plan, in preparing for the future.

Q: Do you know of cases where leaders thought they had done all they could but continued to hang on?

A: Founders, in particular, have a very difficult time leaving "their baby." They’ve invested hugely in its success — more often than not, their name is on the door. But rather than try to preserve or extend their legacy, they would be well-advised to follow the old social axiom: Leave the party when you’re still having a good time.

Q: Do you know of any particularly creative exit strategies that worked?

A: Jimmy Dean, the country and western singer-songwriter, took enormous risks in transitioning from his music career to the sausage business. But in the mid-1960s, he sensed that America was turning cynical (the Vietnam War, etc.) and the folksy, homespun lyrics of country music were falling out of favor. This former high school dropout gracefully exited the often fickle music business to launch the Jimmy Dean Meat Co., which he later sold to Sara Lee Corp. His entrepreneurial talents made the legendary singer a very wealthy man.