Can Bosses and Employees Be Friends? How to Navigate the Work Friend Zone

Can Bosses and Employees Be Friends? How to Navigate the Work Friend ZoneAre you one of the lucky people who loves your boss? Maybe she’s everything you aspire to be one day. Hanging with the team for happy hour. Turning the hallway into a putting green. Giving you solid client insight from her years in the trenches.

Or maybe you’re a boss overseeing the employee of your dreams. He reminds you of yourself when you were just starting out. You, too, were once called a rising star, asked to join junior employee committees while still having time to hit both the gym and the downtown bar scene.

Overall, it’s a good thing to like your colleagues, especially those with whom you have a direct reporting relationship. But in my work, I often hear about the times when these relationships become too close for comfort and the boundaries of professionalism are crossed. Work can and should be enjoyable! But relationships can be complicated.

In this post, I’ll explore the ways you can have great workplace relationships, and even be very friendly, without overstepping bounds. Here are some tips to help both sides navigate the boss/employee friend zone.

If You’re The Boss:

  • Don’t friend your subordinates. You thought I was going to put this under the employee list, didn’t you? Well, sure, it applies there, but you’d be surprised how many employees — usually millennials — come to me, cringing because their boss has requested them as a friend on social media and they don’t know what to do. #awkward. If you’re the boss, don’t put your employees in this tough spot, where they feel they have to accept and then monitor every word they say online. Some offices are friendlier than others, but it’s safest to stick to LinkedIn and avoid connecting on more personal sites like Facebook, Instagram or Snapchat.
[bctt tweet=”Bosses: Don’t friend your employees. Stick to LinkedIn.” username=”lindseypollak”]
  • Be likeable. Some of the best advice I’ve heard about managing and relationships comes from Alexandra Lebenthal, CEO of the financial firm Lebenthal & Co. “The best leaders I have known are the ones who let their true personalities shine through by being open and approachable,” she says in an interview we conducted for my book, Becoming the Boss. In my experience, the best leaders of any age are confident and strong, while still being fair and open.

If You’re the Employee:

  • Understand if your boss isn’t into chitchat. I enjoyed this recent article by Kristin van Ogtrop, managing editor of Real Simple, about why a boss might not ask about your weekend. It’s not because he doesn’t like you or she doesn’t care. It’s because you’re all there primarily to work.
  • Find other friends. When you have a great relationship with your boss, you might start to feel like you’re developing a relationship that feels more personal than it is. As you go through ups (the big client win!) and the downs (the big client loss!), you forge bonds. But, at the end of the day, you have to remember that your boss can’t be your everything. Make sure that your work-life integration focuses on developing solid relationships outside of work, too.
  • When in doubt, err on the side of polished and professional. If you have fallen into a friendly routine with your boss, kudos to you. But as the employee, it is your responsibility to always monitor how much is too much. Take your cues from your boss: Does she try to change the subject when you talk about a late night after-party you attended? Is he sharing about his family as much as you are? In any work situation, it’s better to be safe than sorry.

Have you ever been in an awkward, overly familiar spot as either the boss or the employee? How did you handle it? Share with all of us in the comments below!

Lindsey Pollak is the leading voice on millennials in the workplace, trusted by global companies, universities, the world’s top media outlets — and, most importantly, by millennials themselves. A New York Times bestselling author, Lindsey began her career as a dorm RA in college and has been mentoring millennials — and explaining them to other generations — ever since. Her keynote speeches have audiences so engaged that, in the words of one attendee, “I didn’t check my phone once!” Contact Lindsey to discuss a speaking engagement for your organization.

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Lindsey is a globally recognized career and workplace expert and the leading voice on generational diversity. She has spoken for more than 300 audiences including Google, Goldman Sachs, Estee Lauder, Stanford and Wharton. Lindsey is the author of four career and workplace advice books, and her insights have appeared in media outlets including The TODAY Show, CNBC, NPR, the Harvard Business Review and the Wall Street Journal.


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