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Part of the series "Building Your Happiest and Best Career"
As a career coach, I regularly hear from writers and journalists in the media who have powerful questions involving how to build a successful career. They typically ask questions around how to avoid making big mistakes in navigating through specific tough challenges. Most often, these are complex issues that don't have an easy, black and white answer because they touch on the deeper aspects of human experience, such as power dynamics, dealing with bias, staying emotionally well during crisis, boundary development, demonstrating integrity, and more.
Recently, I heard from writer Aly Semigran who was developing a piece on whether employees and bosses can be friends. Her full questions were really insightful and probing, and many of her questions are the same I've heard from my own career coaching clients and course members over the years. Aly offered a short excerpt of a few of my answers, along with quotes from other career experts, in her article on Well+Good about Can You Be Friends With Your Boss (and Should You)?
Below are my full responses to her questions on how it can work effectively (and why it frequently doesn't) when bosses and employees are friends outside of work.
First, should bosses and employees be friends?
I think the answer to this depends on how we define “being friends.” It’s wonderful to be friendly with your boss and subordinates – to have an easy-going, open and friendly rapport based on mutual respect, care and concern.
But if we’re taking about taking it further – socializing outside of work, having your boss meet your family, sharing long periods of time together and intimate details of your life, etc. – it’s very tricky waters and you have to know how to handle this effectively. Doing this well involves building strong boundaries so that the “friendship” doesn’t impact how you perform your work together, and how you relate as professionals in a situation where the power between you is not equal.
As a former corporate director and VP, and one who has worked with many bosses and employees and on occasion been good friends, I’d say that it can work out well, and be productive and positive in the lives and careers of both parties.
That said, it can also backfire terribly, (as it also has in my own life) and there are some real pitfalls to watch out for in developing a friendship with your boss or employee. A romantic relationship is far trickier, and not advisable. Why? Because, when there’s a significant power differential in a relationship, and when one party can directly influence and impact the other’s ability to succeed in their role, then equality (and even true consensuality) in the relationship is not possible. And if and when the relationship falters, there can be a huge price to pay.
Let's say an employee gets along with their boss and is thinking about trying to spark up a friendship, what's the best way to go about this?
Most if not all friendships don’t start with someone saying, “Will you be my friend?” They emerge organically, with the two individuals having an interest in getting to know the other better. Perhaps they have a meeting at work and afterwards, one says to the other, "Want to go have lunch?” During lunch, the conversation then moves away from strict work topics into more personal issues. Then there’s a developing feeling of mutual connection, understanding and interest.
Or when people attend social events outside of work (such as drinks or a social activity or off-site) where people are encouraged to be more “themselves” than the workplace tends to encourage, friendships can begin to form as people begin to reveal a side of themselves that they may not share as openly during work. When that happens, and a personal connection is formed, it often naturally grows into something that expands beyond the confines of a “work” relationship.
Does the same go for the boss who gets along with their employee and wants to pursue a friendship outside of work?
When we’re talking about a boss – the one with the greater power in the organizational hierarchy – he/she has to be very careful and judicious. When a boss initiates a friendship with an employee or subordinate, there’s always a power aspect to it. Pretending there isn't is just denial. For instance, what if the employee doesn’t want to be friends but now feels pressure to act like they do?
I believe that if you’re the one with the power (the boss), it’s best to have stronger, more well-formed boundaries around this, and not directly pursue a friendship with a subordinate unless it forms more organically.
What are the advantages and disadvantages of a boss and employee being friends?
Here are three key advantages:
- You know each other better and can build greater interest, compassion, and respect through your personal relationship.
- You may be more engaged and committed to supporting the other, because of the mutual respect and appreciation you have for each other.
- Work can become more “fun,” relaxed and enjoyable because you’re able to be more yourself and authentic with this individual than perhaps you normally would.
The key disadvantages are:
- If the relationship goes sour, it inevitably taints the work relationship and that can go very badly for both people involved. And it's extremely hard to work with/for someone who's hurt you or with whom you have serious conflicts.
- If the relationship has problems, now there are personal things this individual knows about you that perhaps are no longer “safe” in their hands.
- Even if the relationship stays strong, sometimes personal affinity with someone colors your judgment about their performance. As a boss, that’s particularly challenging in that it could pave the way to preferential or favorable treatment of this individual whose work performance perhaps doesn’t merit it.
- Close friendship between a boss and a superordinate can also throw the balance off of the whole team. Members of a team or department who don’t experience this close friendship can feel jealous, left out and potentially feel they are being side-lined or not seen and appreciated.
- Finally, there are times when emotionally-imbalanced individuals take the “break up” of the friendship very hard, and will decide to go to great lengths to punish the “offender” in his or her mind. This is particularly true when the one who is “left” in the relationship (vs. the “leaver”) has narcissistic tendencies. In those cases, the one who’s left can go to great lengths to hurt and damage the reputation of the leaver.
I'd add that a personal friendship outside of work can work only when both parties are:
- Emotionally mature
- Transparent and honest
- Capable of effectively managing their feelings and emotions when things get tough
- Well-boundaried and can say "no" to what doesn't feel right or good
- Aware of the power dynamics at play and strong and brave enough to address them
- Not willing to use or manipulate other people as pawns for their own benefit
Should rules be set in place for a boss and employee who are friends? For instance, should they not talk about work things outside of the office, and vice versa? What about things like money and raises?
Here’s where strong, healthy boundaries are essential. It’s important for the boss and employee to make some ground rules about their relationship, including the understanding that the boss needs to remain fair and just in her leadership and management, and can’t show preferential treatment to this employee. Money, promotions, raises, bonuses – all compensation related matters that are handled in the purview of work should not be discussed outside of work. And they need to be discussed at work only under the appropriate conditions and at the right times.
Plus, any discussions (and gossiping) about other employees or colleagues simply can’t be allowed. Why? Because that type of sharing compromises the manager’s ability to manage and lead, and it impacts the employee’s ability to effectively work with his/her colleagues.
It’s critical to remember again that if you are a friend of someone who is at a lower level in the organization, there’s power there to be wielded, and that power must not be abused.
How should a boss and employee handle the concerns of other employees who may think the befriended employee gets preferential treatment?
The best way to handle this is to ensure there IS no preferential treatment. Be ever vigilant that you are not feeling, showing or sanctioning treatment that puts this friend above others in the workplace, because if you are, it’s unfair to others and you're not doing your job.
And understand that everything is energy, and the “energy” of your friendship will be apparent. There will probably be some jealousy and concern on the part of other department members when they see a close friendship forming between their boss and a particular individual. It will smack to some as unfair bias, and you’ll have to make sure that there IS no unfairness, or you’ll be inevitably challenged and questioned.
Should a friendship be brought up with HR?
In my view, a friendship with a boss or employee is not the arena of HR, unless there’s been a complaint from this friend or another individual about preferential or otherwise inappropriate treatment. Then, full disclosure on the nature of the friendship will be requested/required.
How should an employee make sure their friendship (including time outside of the office spent together, or even disagreements), doesn't bleed over?
Effective management of personal relationships with bosses and other colleagues takes strong mindset and emotional management and maturity. If you want this friendship to work, you have to be emotionally healthy and able to regulate your own thoughts and behaviors to make sure that anything challenging in the friendship will not bleed over into how you do your work, or how you perceive your boss and his/her management capability.
As a trained therapist and coach, I can say that this is very challenging for most people. When they’re having problems with a friend, they often lose their ability to think neutrally and calmly about it. They feel hurt and often want to blame the friend and make this friend “wrong.” And people who are vindictive want to then cause more hurt to the other. You can see how quickly that type of thinking will be destructive if the person who’s “wrong” in your mind is your boss.
To make sure it doesn’t bleed over, be very mindful and aware of your thoughts and feelings about this person, and if your anger, resentment or hurt feelings affect your functioning and thinking at work, get some outside (neutral) help from a friend, coach, accountability buddy, or in cases where it’s needed, obtain therapeutic help.
Why do bosses and employees make such good friends in many cases?
First, it’s important to realize that bosses and employees are just people. The rank or title they hold doesn’t necessarily make them different people from who they would be without that rank. So of course, we’re going to find great friends among the people we work with every single day. After all, most of us spend more time with our work colleagues than with anyone else in our lives, including our families. And often we’ve been drawn together at a workplace because of shared interests and values.
Secondly, there’s a context basis to friendship that often solidifies it. In other words, haven’t you ever noticed that you’ll make great friends with people in your immediate context (your work, volunteer efforts, church/temple, hobbies, etc.) that you perhaps would not be friends with at all if you didn’t see them regularly in this setting?
Being in the same context and environment can often foster a special bond because you’re experiencing things together that give your life and personal story greater meaning and purpose. And often, you want to share, explore (and sometimes vent) about it.
Doing so together creates a sense of shared experience, validation, connection and deeper understanding of yourself and the world around you. Building great relationships at work can enrich your professional experience and success, but it can also crush it. Be careful to manage these relationships with all the maturity, well-defined boundaries, equanimity and self-awareness you can muster.
For hands-on career success help from Kathy Caprino, visit her Career Growth Coaching programs and her Finding Brave podcast.
