Workplace Relationships: Why bosses and employees shouldn’t be friends
Can a boss be friends with his or her employee(s)? No, based on my experience and according to several human resources professionals I spoke with—who have witnessed (or put an end to) workplace relationships—I agree. And here’s why.
Why Workplace Relationships Between Managers and Staff Spell Trouble
I became good friends with a now-former manager at a company where we worked. He and I played squash, had friends and acquaintances in common, and supported each other in our personal lives. Then, a client at the firm decided he wouldn’t pay his invoices due to what he called poor service from the account executive on the business—me. For him to pay his bills, he said I would have to be fired. And fired I was—by my boss and (I thought) friend. As the adage goes, “Nothing personal—it’s just business.”
Bosses and employees shouldn’t be friends (or lovers, for that matter). Consider the recent “ColdPlaygate” fiasco involving the former CEO of Astronomer, Andy Byron, and chief people officer Kristine Cabot. As witnessed by millions of viewers after the short video went viral, their workplace relationship has become a cautionary tale for those whose professional connections stir their loins and are poised to consume them.
Poof. Two careers up in smoke—at least for now.
Bosses who hire friends can create similar issues for themselves and their friends. I was once hired by a firm’s CEO, who was a personal friend of mine. Once word of our friendship got out, colleagues feared I would be his office mole and reap an unfair advantage at performance review time. Resentment started to build as my colleagues began to ghost me. The CEO and I parted ways—still friends—shortly thereafter.
When spending 10 or more hours together in the office after years of working apart and/or remotely, workplace relationships are bound to develop.
So, here are 10 reasons why pursuing a boss/employee relationship is not a good idea:
- Perceptions of favoritism may emerge among coworkers of the employee who is friends with the boss, leading to resentment.
- The employee may be asked by the boss to do something business-related to support their friendship, even if they disagree with the strategy or task.
- Lines blur at review time—The employee may feel shortchanged after a salary review. Even if the boss grants a raise, the employee won’t be sure it was performance-related.
- Difficulty being critical—Close friends may struggle to critique each other honestly. Business growth relies on unbiased evaluations. Firing a friend is even harder.
- Friendships as a means to an end—Some managers and employees bond for career gains, whereas true friendship is unconditional.
- The power gap remains—Management and subordinates will always see a hierarchy, unlike in real friendships between equals.
- Conflict of interest—Managers must monitor productivity, but friends encourage rather than scrutinize each other.
- Confidentiality risks—Unlike with therapists or doctors, corporate confidences are more likely to resurface negatively.
- Promotion tensions—An employee may expect preferential treatment, but the boss must promote the best candidate, not a friend.
- Negative feedback hits harder—Managers may take criticism personally, affecting morale and productivity.
Bosses can be great to socialize with during team-building events or company celebrations, but everyone needs their own space and life outside work.
If you see someone (like your boss) in a stressful work environment up to five days a week, do you really want to spend your off-hours with them too?
As this updated 2025 examination of workplace relationships demonstrates, blurring professional boundaries often leads to damaged careers and broken trust. While team camaraderie is valuable, the risks of boss-employee friendships – as outlined in our 10 key reasons – remain as relevant today as when this was first published on HuffPost in 2014.
First appearing on HuffPost in 2014, this refreshed 2025 version includes new perspectives.