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How To Befriend Your Boss

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Are friendships in the workplace or with your boss “to be, or not to be?” That is the ultimate question.

Growing up, I was often under the impression that it is permissible to be friendly in the workplace but not friends. I had assumed that being friends with someone that you also have a professional relationship with could do two things: 1) hurt your ability to make sound, logical decisions; and 2) may blur the lines with regard to having conversations that are appropriate for work.

However, as my time in the professional world has increased, I have found that friendships in the workplace can be a wonderful thing–-especially with your manager or boss. When you befriend your boss, a few great things occur naturally:

1) Giving them honest feedback can become an easier task rather than something that’s really difficult.

2) You can be sure that you and your boss are a true team; you have each other’s backs in difficult situations.

3) You have a friendship that can last a lifetime.

What You Should Do

If there comes a point where you decide that befriending your boss is appropriate or of interest to you, it’s important to know that there can be right and wrong ways to do so.

First and foremost, one’s boss can often be intimidating, but it’s important to remember that they are a real person with: a life outside of work, a family, many friendships, and personal hobbies. When you realize this, begin to ask this person about those areas of their life. When that person shares this information with you, then you can begin to understand what means most to them and pursue those topics in following conversations. If your interactions only relate to work tasks, responsibilities, performance or office politics, your boss will continue to see you as a direct report, not a person that they could develop a friendship with.

Here are some examples of questions you can politely ask when the timing is appropriate:

1) What are your plans for this weekend? (And to then follow up the next week with additional questions.)

2) I love kids! Tell me more about {insert children’s names here}.

What You Shouldn’t Do

When befriending your boss, there are also a few things that you should avoid. First, it’s important to keep your friendship from becoming an emotional crutch or a negative space. Often times, it’s easy to complain or vent to a friend. But you want to tread lightly here because it’s important that your boss sees you as a strong employee with a positive attitude, and has the ability to work hard in difficult situations.

Second, avoid gossiping to your boss or encouraging your boss gossiping to you. Again, it’s necessary for the friendship to be a positive one. What you don’t want to occur is that either 1) your boss accidentally repeats the gossip you have shared, or 2) begins to develop an impression that you like being involved in gossip.

Third, understand where the line should not be crossed as a professional. For example, it would be inappropriate to tell your coworkers, including your boss, that you won’t be on your A-game today thanks to a massive hangover from last night’s shenanigans.

And lastly, be very aware of the impression you’re creating by becoming friends with your boss. You want to be sure that you two aren’t always sharing “inside jokes,” or laughing privately and not including others. That type of behavior is unprofessional and will create a negative team dynamic.

The key to having a successful and appropriate friendship with your boss is to understand how far to take that friendship. Always remember that you are an employee first, and a friend of your boss second. Then becoming BFFs with your boss could be a wonderful thing that leads to better communication, increased confidence in one another, and a life-long friend.

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Topics:

Career Advice Manager Friends At Work Bosses Personal Relationships
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