Can I be friends with the boss?

In your parents’ generation, being friends with a boss was rare. Most people in the baby-boom era were very happy to keep work and personal relationships separate… by a wide margin.

In your parents’ generation, being friends with a boss was rare. Most people in the baby-boom era were very happy to keep work and personal relationships separate… by a wide margin.

But today’s younger employees, particularly workers under 30, have a different view.

In a recently released research study by the MSLGroup called “The Millennial Compass,” some truths about the values of workers under age 30 emerged. And there were some surprises.


The majority of millennials surveyed were more likely to describe their current relationship with their boss as a friend, above other options such as Coach/Mentor, Knowledge-Source/Expert, Peer or Director/Allocator of Work.

But that doesn’t necessarily mean that younger workers are seeking friendship with the boss. When asked “What is the ideal relationship you would like to have with your boss?” the American and British participants chose Coach/Mentor first. Knowledge Source/Expert was second. Friend was third.

Today’s younger workers aren’t satisfied or comfortable with a boss/employee relationship based on power. They have high expectations of bosses. They seek leadership, not just supervision. And they expect their bosses to bring useful knowledge and expertise, and be willing to share it. Coaching and Mentoring? Yes. Direction or order giving without explanation? No thanks.

Becoming a friend with your boss, like being friends with co-workers, isn’t necessarily bad. We spend a lot of time working closely together. We have shared interests. And sometimes, we have other commonalities, if we are of similar age, gender or share outside interests. That can be a healthy recipe for a satisfying relationship, and there’s nothing wrong with that.

Risks of Being Friends with the Boss

First and foremost, friendships are based on equality. Boss/employee relationships are not. Your boss is the one person in your life who gets paid to make decisions and judgments about you, to assess you and hold you accountable. They hold most of the power to give you raises, or (possibly) determine the amount of a bonus. And if circumstances require it, they have the responsibility to fire you. Your boss has more power (in work matters) and you have less.

Second, there is the perception of favoritism. If you are friends with the boss, don’t assume that will go unnoticed. In most workplaces, it is generally best to assume that there are NO secrets. If you are assigned a plum project, others may resent it. And if you are promoted, there may be doubts about how, or if, you truly earned it.

Finally, there is the thorny issue of sexual politics. If your boss is of the age/gender/sexual orientation to even be perceived as a romantic target (by you) or to have a romantic interest in you, you can bet that the water cooler rumors will fly.

How to handle your friendship with your boss

If you are already friends with your boss, or think there is a welcome friendship brewing, here are a few steps you might consider to make both of your lives easier:

DO: Talk about it

Let your boss know you are committed to your professional success, and want to ensure that your friendship doesn’t get in the way. Talk about any possible problems you fear the friendship may cause. Your boss may have similar fears, and will probably welcome the chance to get them out in the open.

DO: Maintain clear boundaries

As much as possible, keep your conversations about business at the office and save the personal for after work. Respecting that line will help you both separate your friendship from your working relationship.

DO: Respect feedback

You also need to learn how to accept criticism when it's justified and address it when you feel it's not. So ask your boss for a biannual review. Formalizing the way you receive feedback will help you take any criticisms less personally and you'll have a list of concrete objectives you've both agreed on.

DON’T be naïve about perceptions of others.

If you are concerned that others might judge you harshly, you’re probably right. If that will make your professional life difficult, steer clear.

DON’T only have work friends…including the boss.

Remember to keep a focus on your friends from outside the office. A friendly workplace is great, but it's your friends outside of work who can give you the clear perspective and support you need to leave work where it belongs.


Ed Hunter is a Career and Executive Coach, and principal of Life in Progress Coaching. Contact him at, or at