Shopping for a friendly boss or a friend

Boundaries shift in today’s workplace, even in more formal settings such as law firms, according to John Jakovenko, principal at Alpharetta, Ga.’s the Jakovenko Group LLC. Smart job hunters consider many factors, but the nature of the boss-employee relationship as friends or as friendly deserves more attention, because it’s reinforced by open offices and casual environments. Steve Arneson, author of “What Your Boss Really Wants From You,” reports that if you don’t resolve it while interviewing, you might encounter trouble on the job (Berrett-Koehler, $15.95).

You want the job and want to be professional about it, but familiarity may sidetrack the interviewer, indicates Dinah Day, president of the Image Circle Inc. in New York City. When topics become personal, you become uncomfortable. “Then the company asks you back and acts very personal,” she says. “That’s a mixed message (on its part) … not smart at all.”

However, Jason Cannon doesn’t mind a boss who becomes a friend. Founder of Linux Training Academy in Iowa City, Iowa, he considers friendship acceptable, as long as the relationship veers toward friendliness. He’s eaten pizza with his boss in his traditional job in an IT firm. Cannon gave himself advance notice by interviewing potential co-workers on a conference call. He noticed their lightheartedness.

He has professional reasons for endorsing friendship.

“You get to be in on the inner-inner circle,” he observes. “You can see more of the big picture, what’s going on his mind and what he’s thinking beyond what he can say publicly.”

Cannon concedes that because a friendship can deteriorate, the only way to assess risk is to trust your gut.

“It depends on the situation, for sure,” mentions Arneson, a former HR senior executive in industry leaders, “but the boss still needs to make decisions about your performance, salary, bonus, promotions, etc., all of which are harder to do (objectively) if you’re ‘best friends’ outside of work.”


If you accept interviews knowing that friendliness will work for you but not friendship, watch your potential boss’s behavior. Points of familiarity, such as a shared alma mater or knowledge of the same person, may steer the discussion off-course, Jakovenko says. Arneson concurs, saying to be aware of similar age, gender and demographic traits. “Gravitating toward hobbies might be a tip-off,” he adds. “Look for cues and nonverbals.”

“Deflect first and then be direct,” he advises. “Get the hiring manager back onto the job and its requirements.” Day notes that you don’t want to insult the person but that you must cut through the rapport.

“Reel the other person in to avoid inappropriate behavior and sexual innuendo,” she says. “It’s tough to do when you’re encouraging (the person to like you) and wanting to maintain respectful boundaries. Incorporate your interest in (the activity), followed by ‘but I’m hoping we might be able to sail through to some questions about your company and trends you’ve been involved in.’ ”

When job hunting, know whether you want to be friends with your boss. If so, you might get to be. But if you don’t, when interviewing, redirect the conversation when it becomes too personal to the work that brought you there.

Dr. Mildred L. Culp of WorkWise® welcomes your questions at © 2014 Passage Media.


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