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Bostonia: The Alumni Magazine of Boston University

Fall 2008

Advice from the Top About How
to Get There

A CEO's Take on Picking and Winning Your Battles

| From Commonwealth | By Art Jahnke

David D'Alessandro's latest book made the New York Times best seller list. Photo by Fred Sway.

At an age when most executives are still striving to reach the corporate pinnacle, David D'Alessandro had already been there, done that, and retired—as much as anyone with his energy and interests is capable of retiring.

The former chairman and CEO of John Hancock Financial Services, D'Alessandro is vice chairman of Boston University's Board of Trustees, a guest columnist for the Boston Globe, and a guest commentator on CNBC. He's written three books on how to climb the corporate ladder; the most recent, Executive Warfare: 10 Rules of Engagement for Winning Your War for Success, made the New York Times best-seller list of advice books this summer. Unlike many of the genre's books, Executive Warfare (McGraw-Hill), written with Michelle Owens, doesn't couch unpleasant realities of corporate leadership in complaisant corporate-speak. Bostonia spoke to D'Alessandro about getting ahead and staying there.

Bostonia: What should employees do if they suspect that they are a bad match for an organization?

D'Alessandro: People who are matched badly to a job often stay too long, and sometimes they try very hard to make it work. Frankly, you have to look for feedback inside and outside the organization to see if it's fixable. If it's not, you have to get out. It's always better to get out on your own terms.

Bostonia: Is there one cardinal rule to getting ahead and staying ahead?

D'Alessandro: One is, don't travel too much. What is happening at home in a large corporation is extraordinarily important. If you're on the road a third or half of the time, you can become a forgotten entity. I don't care about BlackBerrys or other ways to connect—not being with the other people in the organization is a mistake.

Another mistake that many people make, and this sounds obvious, is that as they move up they forget they still have to do their job. If you've been successful, you have to continue to succeed, because that's the ante to play for higher stakes in the organization.

Bostonia: Is there one widely held fallacy about climbing the corporate ladder?

D'Alessandro: One of the great fallacies of organizational life is that you always have to go along with what upper management says. In fact, you don't get to a leadership position without knowing how to question upper management. It's important that you question them in private. You don't ever embarrass them in public.

Bostonia: Is it important to be a benevolent leader?

D'Alessandro: All senior management people who aspire to higher positions have to have a reputation as benevolent. You can be very good at what you do, you can be tough-minded and deliver results, but people around you are going to have personal circumstances where they have to take a leave or they need something in their personal life, and people will watch to see how you treat other people. Even if you are a great performer, heartlessness does not win at the end of the day.

Bostonia: Would you advise an aspiring executive to socialize with people from work?

D'Alessandro: No. If you socialize with people from work, you are going to be put in a difficult situation. Someday you may have to fire that person. Spending lots of time with people from work is dangerous, because you are crossing lines and entering a place where people know too much about you and you know more than you may want to know about their circumstances. You should try to keep your work life and home life separate.

About drinking: work is not a fraternity. You are not in college. My advice? Have another iced tea.

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