Gently does It: Your friendship with your boss should not come in the way of work

Q. You work for a good friend, but lately you’ve begun to have doubts about his business judgement. Is there a way to handle this without ruining the friendship?

A.Nobody enjoys unpleasant discussions with friends, but your job requires that you put the interests of the company first, said Michael Gibbs, clinical professor of economics and human resources at the University of Chicago. “Friendship is important, but at the end of the day, your top priority at work has to be the business itself,” he said. “When you start losing faith in your boss’s ability to perform on the job, it’s time to speak up.”

Q.Was it wise to agree to work for a friend in the first place?

A.It’s late in the game to question your decision, but it’s worth remembering that mixing personal and professional lives can be tricky. Sure, it can be fun to work with people you know and respect. It can be very rewarding to share passion for a mission with pals you’ve known for years. Bill Gates and Steve Ballmer, for example, were roommates in college, joined forces at Microsoft in 1980 and still work together today. Even if the two quarrel behind the scenes, the relationship evidently works.

But working for a friend can be a minefield. Your friend may assume that you are on top of things when you are not. You may have different interpretations of the corporate culture, or divergent expectations for the job. Power is another issue: when a friend decides how much money you make, how much vacation you can take and what kind of promotion you’ll get, the dynamics of your relationship can be challenged.

Q.How do you talk to your friend about this problem?

A.There will never be a perfect time or place, so just do it. Confine business discussions to the office and approach the boss as any other employee would, by scheduling a private meeting during the day. Dr Leann Mischel, assistant professor of management at Susquehanna University in Selinsgrove, Pennsylvania, says that this strategy keeps your friendship separate from work and conveys to your friend ? and to colleagues who pay attention ? that you don’t expect to be treated differently than anyone else.

Q.How do you express your misgivings in a way that preserves your job and your friendship?

A.Every relationship is different, so you’ll have to decide for yourself the most appropriate way to communicate your concerns. Some friendships are relatively formal. Others allow friends to speak as freely in the workplace as they do in a bar. Because friendships change over time, you’ll have to make sure that your approach is sensitive.

Regular communication can be important in heading off trouble. At 1-800-Got-Junk?, a rubbish removal business based in Vancouver, British Columbia, Cameron Herald has reported to his best friend, Brian Skudamore, since 2000. The friends meet once in a week to review performance and discuss their goals. Over the years, this approach has fostered what Herald, the chief operating officer, calls a “painfully honest” method of communication, in which each man speaks his mind clearly and directly. “I’ll always voice my opinion,” Herald said. “If Brian doesn’t like what I have to say, I’m fine with it so long as I know my opinion has been heard.”

Q.Are there ways to make the encounter easier from the beginning?

A.The closer the friendship, the easier any discussion will be. For those friends who aren’t as open as Herald and Skudamore, a more careful and even legalistic approach may be best.

Susan Hodgkinson, president of the Personal Brand Company, a leadership development firm in Boston, says she sometimes counsels clients to participate in a “contracting conversation”, during which they make a written record of goals as well as methods for dealing with potential conflicts. Hodgkinson encourages her clients to add to the document throughout the year, creating a tool to solve problems as they arise.

“It’s subtle, non-edgy language that helps put things into perspective,” she said. “For some, the notion of contracting makes for a more productive outcome.”

Q.Is there a way to salvage your friendship if your friend rejects your criticisms outright?

A.Maybe not. If you’ve reached an impasse, you may try to involve an arbitrator, assuming that your firm has a human resources department and access to a specialist who will focus on the facts of a case and try to defuse an emotionally charged situation. Another option, of course, is to request a transfer or to leave the company.