Friends with the Boss – 8 tips to make it less complicated 

During my last corporate job I became good friends with my boss’ boss. I got to know her family and we spent many pleasant evenings visiting and swapping stories. Work was one thing and our personal relationship was another. It wasn’t a problem at all… for us.

My immediate boss (my friend’s direct report) had an entirely different opinion. He complained that I was circumventing his authority and refusing to follow the chain of command. I felt like he was playing a game of “gotcha” by silently attending my conference calls and creeping behind my back to “follow up” with my vendors and clients. The whole situation became unnecessarily messy.

Having friends is important. And since most of us spend the greater part of our waking hours at work, having friends at work is equally important (The HBR talks about the importance of friendships at work here). It is just as important that our work doesn’t suffer because of a friendship and we’re not seen as playing favorites.

Here’s how:

Is it real? – I have had “friends” at work who were friends because I saw them every day but when our lives took us to other places of employment the friendship faded. My longest and most enduring friendship is with someone I met at work in my mid-twenties. We have stay friends through many life changes. Before you give your time, energy, sweat and tears to a friendship ask yourself “Is this someone I would stay in touch with and who would stay in touch with me if we weren’t working in the same building?” If the answer is yes, the following applies to you.

Remember there are still boundaries – When you are a work, behave like you are at work. No hugging, arm punching or aggressive “friendly banter” allowed. If you cross a line in a friendship outside of work a conversation and an apology fixes most things. Cross a line at work and HR gets involved.

Have GREAT integrity – Whether you’re working for yourself or being paid by someone else it is stealing to “hook someone up” (i.e. give them something for free). This includes not doing your job because you’re friends with the boss or not holding your employees accountable because they are your friends. You can color it any shade of grey you’d like. It’s wrong. To have friends at work you have to be willing draw that line in the sand and not cross it.  

Be the kind of friend you want to have – We all want friends who believe in us even when we doubt ourselves, who listen when we just need to vent and who are able to offer advice in a way that makes us think rather than feel dumb. We also want someone who can give us the hard truth kindly and hold us accountable to our commitments because they respect us. Be that kind of person and look for friends who are that kind of person and the work/friendship balance isn’t that hard.

Be able to manage your emotions and deal with the emotions of others – Passion is a good thing. It drives us to greater heights and makes life interesting. It can also cause a simple situation to spiral out of control. When we are friends with someone we often carry unspoken expectations. When those expectations are not met, disappointment and feelings of betrayal can bubble to the surface. In the work environment it is important to recognize which feelings are professional skepticism (a good thing for business) and which are personal hurt (a separate problem not related to business) and address them accordingly.

Remember everyone has a story – It is easy to “understand” when a friend needs to call in sick because you know her mother is in ill health. Or to be accepting of work not being done by the deadline because your friend is focused on his troubled teenager. It is important to remember that EVERY employee, boss, vendor and contractor has a personal life. You can only be as flexible with your friends as you are willing to be with everyone else. Favoritism will sap morale and work ethic from a team faster than just about anything else.

Be willing to lose – Having friends at work means being able to respect and maintain a friendship through the ups and downs of doing what is right for the success of the business. If you have to let someone go because it is the right decision for the business, they might not be able to see it as anything other than a personal double-cross. If that is the case, your friendship might not survive the change. That is a risk you have to be willing to take.

Talk about it – I like to tell my clients, the best way to make sure everyone is one the same page is to give them the same page to read. If you have bosses or employees who are friends, talk about how the working relationship does and could affect your friendship. Recognizing where there might be a conflict of interest between what is good for the business and what one of the friends wants will help you navigate it more successfully when it happens.

Having friends is vital to our health and wellbeing. You can have great friends at work if you understand the challenges and face them in an informed and strategic way.

Do you have a great story or a horror story about friends at work? Share it in the comments.

As always, I wish you the MOST from your potential!

Doc Robyn

Dr. Robyn Odegaard (aka “Doc Robyn”) is internationally known motivational speaker, executive coach and corporate trainer. As CEO of Champion Performance Development, she works with executives, professionals, athletes, and coaches to help them achieve excellence by sharing active leadership, powerful teamwork, conscious communication, Productive Conflict™ and professional disagreement skills. She is the founder of the Stop The Drama! Campaign and author of the books Stop The Drama! The Ultimate Guide to Female Teams and The Ultimate Guide to Handling Every Disagreement Every Time. To work with her one-on-one, have her present to your team, request a custom workshop or invite her to speak at your event, please call 302-307-3091 or email her at

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