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Why I Stopped Trying to Be Friends With My Employees | Entrepreneur

by Brand Post
May 12, 2025
in Business
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Why I Stopped Trying to Be Friends With My Employees | Entrepreneur
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Opinions expressed by Entrepreneur contributors are their own.

Early in my career as a founder and CEO, I desperately wanted my employees to like me. I believed that if I behaved like my “real self,” I could build stronger bonds with my team. Despite my good intentions, it seldom worked.

I had to learn, and re-learn, a crucial leadership lesson: Employees are not your friends. The inherent authority of your role creates barriers to forming healthy friendships. Worse yet, employees may leverage your friendliness to undermine your authority. This happened to me many years ago, and when it did, I was devastated.

I was attending an industry conference with some employees. On the final night of the conference, there was a big party with food, drinks, a DJ and games. I challenged an employee to a video game competition, which I won. I then bragged about my win in an overly dramatic and flamboyant manner. I behaved this way with my friends, who understood my absurd boasting was not serious.

However, the employee described this event much differently to co-workers. I was portrayed as overbearing and humiliating the employee. When I overheard this twisted retelling, I was shocked. I sincerely cared about my team. I thought we were just having fun. I was only being my “real self.”

My CEO coach helped me see that as a leader, you are always “on stage.” Employees interpret all your behavior through the lens of power dynamics. When you hold employees accountable, an essential part of leadership, resentment can drive employees to label your attempts at friendliness as invasive or abusive.

As a leader, you are entirely responsible for creating and maintaining a productive, positive and supportive workplace. This means you must not only hold your team accountable to their job expectations, but you must also build healthy relationships with each team member. These two demands often clash. You must carefully balance being friendly and demanding. If you go too far in either direction, your authority and respect suffer.

Boundaries help you maintain this balance. Here are some strategies for building healthy boundaries with employees.

Related: Marc Andreessen Says You Shouldn’t Bring Your Whole Self to Work

Be the person your dog thinks you are

I like this aphorism because it humorously captures an important leadership concept: Employees judge you on what you do for them, not what you accomplish as a leader.

Employees may not like you when you hold them accountable, but they will like you if you show genuine concern for their growth and success. Offering consistent encouragement, vocal recognition and genuine positivity minimizes negative perceptions of you as a leader.

Be a cool cucumber

It is entirely normal to feel frustrated, especially with co-workers. It is equally healthy to vent those frustrations to friends or counselors. However, employees cannot be your counselor.

Venting to employees makes you sound cruel, petty and vindictive. It will destroy whatever trust and credibility you have accumulated. Share frustrations or concerns with a mentor, therapist or professional coach instead. Maintain a calm, positive and supportive attitude with employees, especially the ones that irritate you.

Adopt a growth mindset

Blame and finger-pointing are toxic behaviors in the workplace, especially when a leader does it. They create animosity and mistrust. You must rise above blame to adopt a growth mindset.

Rather than focusing on who is to blame, focus on learning and growing. Acknowledge failure, but balance that with the resolve to learn and get better. When my company lost a deal, I was obsessive about finding out why and what we could learn. This turned every loss into a chance to fine-tune our processes, learn from our mistakes and win more deals in the future.

Building a “no blame” boundary ensures that your leadership is based on continuous self-improvement and not toxic behaviors.

Related: Treating Employees Like Pals Can Be a Dangerous Game.

The sound of silence

Silence is a powerful boundary. Let the employees talk, especially when something is wrong. Resist the urge to tell them what is wrong or how to fix it. Instead, be curious and ask questions. Let them hold themselves accountable.

Moreover, when you ask a tough question, remain quiet and allow employees the time to answer. It may feel uncomfortable, but silence allows people to assume responsibility.

Protect your privacy

Your privacy is a critical boundary. Keep personal details superficial. Avoid emotionally sensitive topics like politics, religion, sexuality or personal wealth, as these can incite unnecessary conflict or resentment.

Whether at work or socializing, encourage employees to talk about themselves rather than sharing your personal information. This builds rapport and makes you more approachable.

Establish clear work-life boundaries

Your employees’ privacy is equally as important as your own. Your authority over employees ends the moment they leave work. This is a sacred boundary that you must respect as a leader.

Avoid judgments about what employees do (or do not do) after work. If you must contact an employee after work, then thank them for their time.

Socialize strategically

It is good to socialize with your employees periodically. However, you must maintain a professional demeanor at all times. Remember, you are their manager even after work or in a social setting.

Limit alcohol consumption and avoid divisive conversations. If your spouse accompanies you, make sure you both follow these guidelines and maintain a united front.

Related: Employee or Friend? How to Maintain Boundaries with the People Who Work for You

Avoid competitive situations

Let your employees win. Any competition with employees should remain casual, friendly and devoid of any real stakes. Never wager real money, and avoid boasting after wins to prevent negative perceptions. If you engage in physical activities such as playing basketball or working out, you are still their boss. Overly aggressive or antagonistic behavior will translate back to work and may provide fuel for negative narratives.

You are always the boss — at work, after work, all the time. While it is possible to build friendly relationships with employees, true friendships are challenging.

Boundaries protect you and your employees. They help maintain respect and authority. They allow you to be friendly without overextending your authority.

Early in my career as a founder and CEO, I desperately wanted my employees to like me. I believed that if I behaved like my “real self,” I could build stronger bonds with my team. Despite my good intentions, it seldom worked.

I had to learn, and re-learn, a crucial leadership lesson: Employees are not your friends. The inherent authority of your role creates barriers to forming healthy friendships. Worse yet, employees may leverage your friendliness to undermine your authority. This happened to me many years ago, and when it did, I was devastated.

I was attending an industry conference with some employees. On the final night of the conference, there was a big party with food, drinks, a DJ and games. I challenged an employee to a video game competition, which I won. I then bragged about my win in an overly dramatic and flamboyant manner. I behaved this way with my friends, who understood my absurd boasting was not serious.

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Tags: Business CultureEmployee Experience & RecruitingEmployeesentrepreneurFriendsLeadershipManagementManaging EmployeesRelationshipsStopped

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