Employee Benefits: Friends with Your Boss?



Everybody who works has or has had a boss. Many of us have been bosses, and we have all had varying experiences regarding  whether you can be friends with your boss.

I would like to believe that we all can answer, “yes, absolutely,” but there are clearly two distinct schools of thought on this subject. 

Barbara Pachter, a business etiquette speaker, lectures on improper relationships between a manager and employee. “Are you friends with benefits? Because that is not OK. What is the gender balance? Is it male-female? That’s a little tougher. What’s the age gap? Is it your immediate boss? If it’s a more senior level boss, they can get in trouble for having friendships with younger underlings.”

Ms. Pachter cautions that being friends with your boss can potentially have negative effects on you, your boss, your co-workers, and your working environment.

On the other hand, Angie Herbers, a professional HR consultant, says that being friends with your manager can be a good thing and encourages friendships between bosses and their employees.

“People like to work with people they like, and if you can develop a friendship with your boss, you’ll want to be more productive, work harder, and probably want to stay at the company.”

Some things to consider from both consultants were:

- Will you be able to accept difficult feedback from your boss when you are not doing a good job at work?
- How will you feel if there ever comes a day your boss has to say, “You’re fired!”?
- What will you do if your boss shares confidential work information with you that your co-workers do not know?
- How will you react to charges of favoritism when you get a key assignment or big reward?
- On the other hand, how will you react if you don’t get that key assignment or reward? Will it ruin the friendship? If it ruins your friendship, will that in turn ruin your career? 

Webster defines “friend” as “one attached to another by affection or esteem; favored companion.”

For me, it is impossible to be friends with anyone unless there is mutual respect and belief in the other person’s intentions. My first manager was an amazing talent and mentor. We worked many late nights together, and over the years we became very close, socializing and even occasionally vacationing together.

There is a fine line that a manager
can't cross.

It worked because from the beginning, we established ground rules and developed a mutual respect for each other.

There was always open, candid communication with ongoing opportunity to ask questions, challenge opinions, and make a business case to defend your position.

However, there was also an understanding that if or when a tough decision had to be made, it would be accepted with grace and we would agree to disagree.

We agreed most of the time, but when we didn’t, I believed she always had my back and acted with good intentions, doing what she thought was best for the business.

I have learned that the same principles apply whether you are a boss or the employee: give your all to the relationship…be transparent, accessible, a good listener, supportive, and care about driving results together with a “can do” attitude.


I interviewed a number of people about this topic and here are a few responses.

A CEO of a life sciences company:

“My most effective boss became my mentor and life-long friend. He pushed me hard to expand out of my comfort zone and develop all of my skills and potential, and when necessary, gave me frequent constructive criticism. I knew based on our personal relationship that his criticism was meant to prepare me for bigger and broader roles in the business. We traveled the world together and shared many business and personal experiences, including spending time with each other's families. I was content in my role as a senior staff executive but he saw in me a leader who could run businesses. I resisted for a long time, but as a friend, he never gave up and refused to accept my reluctance. I finally agreed under his direct tutelage to move into a general management role. I owe a lot to this gentleman and I've never forgotten what he did for me. Even today I call him occasionally for strategic advice in my role as a CEO.”

A COO of a Fortune manufacturing company:

“There is a fine line that I don’t believe a manager can cross with an employee. A true friend will love you no matter what you do. However, in business, there is an obligation to do what is best for the company, and at times, there could be a conflict. As a manager, I certainly care about the personal and professional development of the employee, but I don’t support developing a personal friendship. I find it more difficult to give/receive honest feedback with a friend, in particular about personal performance, and don’t ever want to be put in the position of having to fire a friend.”

The Head of Human Resources of a global professional services firm:

“I prefer to keep the relationship on a professional basis, eliminating the risk of having the lines get blurred. At times, it can be difficult to achieve desired results if there is hesitation to be firm or take corrective action because of a personal friendship.”

The CIO of a prestigious emergency management communications firm that handles world disasters:

“It is definitely possible to be friends with your boss as long as you can accept constructive criticism. I had a great boss and mentor who became a wonderful friend. He was firm but fair and his counsel, at times difficult to hear, helped develop me to be the person/leader I am today.”

The Head of Sales for a global bank:

“I’ve always developed friendships with my bosses and enjoyed spending time together outside the office. We operate with a ‘work hard, play hard’ philosophy. Sometimes, though, it’s a bit challenging to establish just the right relationship and there’s a distinct line you have to feel comfortable enough to cross. There are work relationships and after-work relationships. There are friends you go golfing with, friends with whom you’ll discuss your wife and kids, friends you approach for favors or call in the middle of the night, and friends you’ll invite into your home even when you haven’t cleaned! Transition between the categories is not unusual, but it takes both parties to establish the relationship. Just know where everyone stands.” 

Although there are two camps on this topic, the feedback reflects that there is not a clear black and white answer.

It truly depends on both individuals in the relationship—their experiences, beliefs, ability to give and receive constructive criticism, their level of trust with the other person, and their comfort level with letting their guard down and “crossing the line.”




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