**Why Can’t We Be Friends?**

Is your boss your friend?
Or do you keep clear boundaries?
Can you really be workplace friends?

Recently, I wrote about the essentials of starting a new job and mentioned that you want to establish a good professional relationship with your colleagues and your boss. I even made the crazy suggestion that you may see your boss as a friend. And some viewers took issue! "My boss will never be my friend. Why would I want that?" They may be right, but there have been many times over the years when my senior managers were my advocates, mentors, and, yes, even work friends. Not always, but that was my goal: to establish a positive, mutually beneficial working relationship.

Many of us enter the workforce thinking, "Okay, I'll survive office politics, deliver on deadlines, and keep my head down." But after a few months, you realize that relationships matter. Who you talk to, and how well, can make your work life richer (or more stressful).

One tricky question often looms: should you even try to be friends with your boss? It sounds tempting — a friendly boss can feel like an ally. But it can also be awkward.

Let's discuss the dynamics and real-world insights. And since each situation is different, we'll cover three actions so you can answer the question for yourself.

Why friendships at work matter (even beyond your peer group)

Before tackling boss-friendships, let's see why work friendships matter at all:

A 2024 KPMG survey found that 83% of professionals say work friendships help them feel more engaged, and 81% say these friendships increase job satisfaction. (KPMG)
A 2025 Harvard Business Review article highlighted a key insight: feelings of loneliness and emotional isolation at work are strongly correlated with Burnout, not just because of workload, but because we miss human connection. (Harvard Business Review)
In remote or hybrid settings, loneliness is even more acute: employees often miss Serendipitous hallway chats or watercooler breaks that fuel informal connections. (Harvard Business Review)

So, you could argue that forging relationships (to some degree) is not just "nice to have", it's a buffer against isolation, stress, and disengagement.

That leads us back to the question: Can your boss be part of that work relationship circle (and should they)?

The pros and cons of being friends with your boss

Let's put on both lenses. Below are the benefits and pitfalls, accompanied by relevant data and real-world examples.

✅ Possible benefits

Greater psychological safety

If your boss sees you as more than "just a direct report," you're more likely to feel comfortable raising difficult issues, giving feedback, or admitting mistakes.
Some organizational behavior studies show that when subordinates perceive their supervisors as having behavioral integrity (i.e., consistency and trustworthiness), and when there is mutual rapport, employees tend to be more proactive.
Faster feedback, more sponsorship

Friendly relationships can open doors to more candid conversations about your career, stretch assignments, and professional growth. A boss who sees you as more than a number may be more attuned to your ambitions and better at offering support.
Friendships can evolve into mentorships. Conversations that help you grow and lean into new skills and roles. As long as you're careful not to overshare. Looking for a new job with the competition? Don't tell your boss!
Improved trust

Because loneliness and disengagement are real risks, having a relational anchor upward can help. Managers are also vulnerable to workplace isolation. Work friends may help them feel less detached.

⚠️ Key risks and complications

Perceptions of favoritism

One of the biggest risks is that coworkers might suspect bias (real or perceived) in assignments, promotions, or the distribution of resources. That can breed resentment or undermine your credibility. Psychology commentary warns that workplace friendships may be seen as a trap. Creating team conflicts between loyalty and objectivity.
Boundary confusion

Do you know when your boss is your "boss", and when they are your "friend"? Not sure? Ouch! Watch out.
A FutureCFO Australian study, 47% preferred clear boundaries, 31% said being friends increased motivation, and 40% feared bias.
New leaders often feel a shift in social norms with former peers. When they set new boundaries, it can be more than awkward; it can kill a relationship you have come to depend on.

Emotional pressure

Being friends with your boss can lead to disappointments or conflicts. You may hesitate to speak up or feel you owe loyalty that conflicts with your independent judgment.
Forbes recently warned that close bonds with your boss can lead to blind loyalty, especially in conflicts.

So, the decision is not black or white—context, culture, personalities, and trust matter.

3 Questions to ask yourself before befriending your boss

Before you develop a friendship with your boss, reflect on these:

Do I want clear boundaries?

Do you prefer clear work-life lines, or do you enjoy blurring them? If your boss is very private or formal, you may be pushing an uncomfortable boundary.

What might other colleagues perceive — and how will I handle that?

If people see you as the "boss’s buddy," will that undermine your influence or credibility? Are you prepared to maintain professionalism and transparency?

Can we maintain mutual trust under tension?

Friendship is easy on sunny days. More revealing is whether you can disagree, provide critical feedback, or navigate conflict without breaking trust.

3 Things to consider

Company culture and norms.

Some organizations foster openness, mentorship, and collaborative work environments, while others are highly hierarchical and formal. If your company has strict norms about professionalism, "friendship" may be more limited.

You’ll never be “equal”.

Even the friendliest boss still holds power over raises, performance reviews, and promotions. That means your friendship comes with context that your boss may not fully share. Be realistic.

Not everyone needs to be your friend.

You can be friendly without being friends. I think of past bosses as work friends; we chatted about family and life. But weekends were family time, not work friend time. As a boss myself for over 30 years, my motto was “everyone needs someone to complain to” - but that was likely about me, not to me.

3 Things you can do to build rapport

Find common ground.

Chat about a book, podcast, hobby, travel — not confidential business. Over time, these small signals of shared interest build relational linkage.

Ask for (and offer) help.

If the boss is open, ask for a brief coffee meeting to discuss career advice. When you see an opportunity to lighten their load (without overstepping), volunteer. Reciprocity is relational glue.

Keep it Professional.

During performance or feedback conversations, emphasize transparency by clarifying that worries aren't personal or friendship issues. If in doubt, be sure to clearly define roles within your workplace.

Pulling it all together: What to aim for

A professional friendship, a trust-based respect that allows for easier dialogue and mutual goodwill.
A relationship that enhances performance, rather than undermining it.
One that respects boundaries, avoids favoritism, and stays visible to stakeholders.

Over to you: What do you think?

Do you think you should try to be friends with your boss (or are you already)?

What are your work war stories? (You know, times when boss–employee relationships got messy (or good))?

I can't wait to hear. Let's discuss in the comments (or drop me a message).

Should You Be Friends with Your Boss? The Delicate Art of Workplace Friendships

Why Can’t We Be Friends?