“I guess the atmosphere that I’ve tried to create here is that I’m a friend first and a boss second and probably an entertainer third,” muses Michael Scott, the main character of the hit comedy and mockumentary The Office. Scott is known for his well-meaning but often ill-advised attempts to connect with his subordinates on a personal level. 
Although few managers would try to emulate Scott’s management style, many managers genuinely care about the people who support them and want to be seen as friendly and approachable. A boss who is friendly can be good for workplace morale. However, if it goes too far, it can complicate workplace dynamics and lead to legal concerns.
Jokes that go too far
Friends joke around with each other—sometimes at each other’s expense. Over the course of a friendship, friends discover each other’s sense of humor and have a mutual understanding that no offense is meant by a joke. That is possible in part because a friendship is typically a relationship between equals. Therefore, your friend would presumably be comfortable telling you when a joke crosses the line.
The issue in the workplace is, managers do not always know whether the laughter that follows a punchline is genuine or is of the “I better laugh at this so my boss likes me more” variety. When the people in a friendship are not equals, one person may be uncomfortable telling the other that she did not enjoy a joke. The boss may misinterpret the lack of complaints as an endorsement of the joke and push further and further beyond the employee’s comfort zone without realizing it.
An example may have occurred at Day’s Jewelers. The Maine Human Rights Commission (MHRC) recently found probable cause for a former employee’s hostile work environment claim based on offensive “jokes” targeting American Indians. A lawyer representing Day’s explained the company’s position in an interview with Maine Public Broadcasting:
The company believes that whatever [the employee] is upset about is, at worst, a misunderstanding. They really have a great relationship with him, and any type of comments that were made to him were absolutely joking and not meant to offend him in any way.
Despite his boss’s apparently good intentions, the employee claims that he was uncomfortable with the remarks for years. According to the employee, his boss “told a [MHRC] investigator that he thought that we were friends, so that made it OK for him to show me pictures of his brother, who’s also an owner of the company, dress[ing] up and mocking my culture, dressing up like a Native American and acting out some sort of scene.” The offensive comments included referring to the employee as “Big Indian,” making comments about Indians and “firewater,” and referring to an employee who had a long black braid as “squaw.” Although the case has not been resolved at this time, the allegations demonstrate that bosses don’t always realize when their comments offend their subordinates. As a result, bosses may repeat the offensive behavior.
Real and perceived favoritism
On The Office, Scott tries to be friends with every member of his team, but even he tends to gravitate toward some employees more than others. Employees having the impression that the boss is playing favorites will inevitably lead to strife in the workplace. It can result in employees feeling that they are on the outside and becoming disengaged and disgruntled.
Favoritism is not illegal, but it can lead to legal concerns. If a male boss invites only male colleagues out for drinks after work and later promotes a male employee over a qualified female worker, the female worker may feel that her exclusion from social events had a discriminatory impact on the promotion decision.
Hard conversations become harder
Part of a manager’s job is to provide honest and constructive feedback to her direct reports. That may be as simple as rejecting an idea during a brainstorming session, or it could be as serious as a negative performance review. In both cases, an employee who misinterprets his relationship with his boss may feel betrayed when he suddenly receives criticism from someone he thought of as a friend. It is important for managers to remain objective when evaluating an employee’s performance and clearly communicate that it isn’t personal when they give constructive criticism.
Takeaway
As a lawyer, it is often my job to explain the risks that come with engaging in certain behaviors—e.g., blurring the distinction between boss and friend. Sometimes the pendulum can swing too far in the opposite direction. A boss who 
is perceived as cold and distant will create different morale problems. It’s all about balance. Perhaps the right course of action is to simply reverse Scott’s quote: Think of yourself as a boss first and a friend second.
Connor Beatty is an attorney with Brann & Isaacson in Lewistonn, Maine. He may be contacted at cbeatty@brannlaw.com.