How to Have Friends at Work When You’re the Boss

Girish* is a client of mine who runs a 500-million-dollar business. He gets stellar reviews and is seen as a high potential successor to the CEO.

But he has a friend problem.

Several of his direct reports are close friends and he doesn’t hold them accountable in the same way he does his other direct reports. Often, they don’t do what he asks. And they aren’t delivering the results he expects. It’s hurting his business and his reputation.

When I speak with others on his team about the situation, they see it clearly and resent Girish’s friends. They don’t understand why Girish allows his friends to take advantage of him. And they feel demotivated and disengaged by Girish’s apparent unfairness.

But when I speak with Girish about it, he doesn’t see it at all. He’s filled with empathy for his friends’ struggles, which makes perfect sense since he cares deeply about them. But he’s blind to the damage they’re doing to him and the company.

There’s plenty of research supporting the idea that having friends at work makes you happier and more engaged. But here’s what the research doesn’t address: friendships at work are tricky, especially when you’re the boss.

So tricky, in fact, that many senior leaders avoid them.

Take Bill, who is also a client and the CEO of a highly successful, fast growing billion-dollar company. Like Girish, he gets stellar reviews from the board and his direct reports. But when people offer criticism, a single element comes up consistently; “I’d like to be closer to him.”

His response? “I’m not interested in having friends at work.”

It’s not that Bill is anti-social. He’s actually warm, gregarious, and authentic. It’s just that he’s learned, the hard way, that having friends when you’re the boss can be complicated.

“I used to have close friends at work,” he told me, “people who would come to my house for dinner with my family. But then I had to make hard calls for the good of the business, including firing one of them, and it became too painful – for me, for my family. And I became hesitant to make decisions because of it. So no, I’m not looking for friends at work.”

In other words, Bill doesn’t avoid friendships at work because he’s a bad guy. He avoids friendships at work because he’s a good guy. Which makes avoiding friends all the more painful and difficult for him.

Girish has friends who hurt his leadership and Bill chooses not to have friends to protect his leadership. Is there a good way to pursue friendships at the top?

I’ve come up with four rules to help senior leaders maintain their leadership and their friendships at the same time:

1. Have a clear and super-strong commitment to your business objectives. You have to care enough about what you want to achieve that you are willing to make hard decisions in alignment with your purpose. You need to be open, transparent, upfront, and passionate about that commitment, while knowing that some people, probably friends, will disagree with you.

2. Be comfortable with strong emotions. This includes your own emotions and those of others. If you act on your commitment to the business with integrity, you will make people around you angry at times. They might resent you, withdraw, or get passive-aggressive. However callous this sounds, that’s not your problem to fix. You should be compassionate – you can listen, empathize, and support them – but you can’t be so dependent on the way they feel that you don’t lead your organization the way you need to.

3. Develop your friendship skills. If you’re going to drive your business with passion while experiencing a swirl of emotions, you need to master the skills that will enable you to maintain friendships in the face of disagreement and manage your dual roles of friend and business leader. These skills include unwavering integrity, empathic listening, clear speaking, and strong boundaries.

4. Be prepared to lose the friendship. Recognizing that you can’t ultimately control what happens to the friendship is critical to maintaining it. Even if you have clarity about your role as a leader, emotional mastery, and friendship skills, the other person may not be able to live with your decisions. If that’s the case, you need to be able to feel the sadness and move on. One thing that can help is to have a lot of friends. It’s not that friends are replaceable, but having enough friends will help you absorb the shock of losing one who can’t handle your decisions.

These rules are hard to follow. The critical skill underlying all of them is emotional courage – the willingness to act powerfully in the face of deep emotion. It’s what I believe is the secret ingredient to all great leadership. And it takes real practice.

But it’s worth the work.

Following these rules won’t just help you navigate the complexity of friendships at work. It will help you become a more capable leader overall.

Girish’s “aha” moment started with Rule #1, when he wholly committed to his business results. We evaluated the shortfall and he was able to see that his friends were more focused on themselves than the business and they weren’t doing the job he had been asking them to do. He knew they were capable, but realized they were being resistant.

Rule # 2 brought emotional challenges, as he initiated hard conversations with his friends. He told them he felt taken advantage of and clearly articulated his expectations of them. Throughout the process, he and I worked on Rule #3, developing his friendship skills, and he did a good job being present but firm in all his conversations.

The real test came with Rule #4: Ultimately he had to fire one leader. But the friendship – at least so far – seems intact and his other friends seem to be stepping up. The improved morale of the larger team is palpable.

And Bill? His challenge is different. He never had issues with Rule #1. His stumbling block was Rule # 2 — he was avoiding the hard emotions by not having friends at all. But now he’s taking more risks, getting more personal, and enjoying his colleagues more fully. He already has strong friendship skills, Rule #3, though now he’s exercising them more and getting even better at them.

Rule #4 is the scary part for him. He doesn’t like the idea of losing friends and he’s unwilling to weaken his leadership to keep them. But, recently, after a nice dinner with one of his direct reports, he came to me with the following insight:

Having friends outweighs the risk of losing them.

* Names and some details have been changed

Originally published at Harvard Business Review


  1. Thanks so much for writing on this issue, as I’ve struggled with it over the years both as an employee and a leader. We spend 40 (okay, 50…60+ for some of us) hours at work every week. To experience so much of our waking time in the absence of friendships would be nearly impossible for me personally. I agree wholeheartedly with Bill’s final assessment, that is, “having friends outweighs the risk of losing them.” So true. One of the biggest challenges I’ve seen is in Rule #3. Having relationships requires respect for others, particularly when difficult choices must be made. You can’t be a friend one day and a leader the next – you have to embody both with authenticity. In my opinion, being committed to the business (Rule #1) does not mean that you flip a switch and transform into a party-line-speaking automaton in times of tough decisions. There’s no credibility in that approach, and it’s designed to support only the person bearing the bad news. Difficult conversations, while uncomfortable, don’t have to break relationships and attempts to navigate them in denial of emotion is a considerable misstep. Having said that, your clarity with regards to Rule #1 should always be the touchstone, both for you and your team.

  2. Yvonne Moncovich says:

    And then there is Rule #5 which is that some friendships will outlast the job. I’m not saying you risk losing your job because of your friendships but rather that some relationships are meant to be cultivated far longer than the typical job life cycle. I was blessed this week to be able to call on a co-worker with whom I’ve remained friends for 20 years to have her do some freelance consulting. It would have been my loss to have chosen my job over my relationship with her.

  3. Heather says:

    Do you think sex/gender has anything to do with it? In my experience I see more men able to maintain distance (or be tough on work friends when needed), but women struggle more with finding that balance. I’m generalizing, but the inherent communication style differences (women usually share more and share deeper feelings) contribute to this generalized observation.

  4. Bridget says:

    I worked for my best friend. I found myself working harder because she was my friend. I didn’t want to put her in the position of needing to have a “tough” conversation with me, so I was constantly going above and beyond for her.

  5. Jesse Yang says:

    Thanks for sharing this article, Peter!
    For Friends:
    We would like to share more with these guys, and wants to help them more. But do you think let them work for you is the best way to help them?
    Also you would like them to help you, are they really capable? are they always capable?
    For business:
    You are right. You need to have strong commitment for your target. Does your friend really share the same goal with you? If not, why you hire him(or her)?

  6. niloufer says:

    Thanks Peter,
    I find several people struggling with this issue wherein they are torn between their role and their friendships.That’s where they are unable to become assertive as well.
    Does MBTI – E – I dichotomy play a role ?


  7. Sue Pridgen says:

    I liked the article. Larger scale to my situation (14 years in the same company 3 major departments). I never became friends with any of my bosses. I say that because they were forever moving them around. But I think the word that rings true for me is Respect. Not friendship. If I have a lot of respect for my boss I usually liked them. I could talk to them, they listen to my ideas and in turn return that respect for my hard work. If not for my knowledge but for my ability to learn and willing to do so.
    There was one girl I worked with in the beginning of my first 3 years on the assembly floor. She was smart and a hard worker. But she was also friends with most of the ladies that worked on the assembly floor. They offered her the Lead Person Position more than 3 times that I know of. She turned them down each time. She knew as soon as she took it they would no longer be friends. They would gossip. Anything she said or did would be taken out of context. She was right but she never gave it a chance to find out. As far as I know she kept her regular job and did what they asked.
    Good Article

  8. Allan Spinner says:

    If you are my friend I will give you the shirt off my back but if you work for me I can’t do that for a host of reasons not the least of which is how those other employees at the same level view it. I found it to be an unmanageable situation that ends up losing a friend and an employee. Do yourself a favor and find your friend a job with a supplier or competitor instead.

  9. Steve Cooper says:

    With a list of rules, we find the converse to be true as well. An employee’s view of this list should have interest as well. 1) We can only have a clear view of the mission and objectives, if they’re communicated to us effectively. This doesn’t require friendship, but perhaps it does need empathy behind it to truly be effective. 2) Strong emotions grow from our passion and beliefs. We know what it feels to be steamrolled, but with a friendship, we would expect to build loyalty, a good emotion-based virtue. 3) Friendship skills need a model and almost always receive reciprocity. 4) Prepared to lose the friendship? Sure, if I have screwed up, I need to be corrected. A friendship should make it easier. When it doesn’t, someone did not communicate my shortcomings. Personally, having lived through these relationships on both sides, I only have one regret. I did have a boss who I thought was my friend. When circumstances had us part ways, even though I reached out, he has never been available since. My naivete may be showing, but I believe that sooner or later, had we stayed in the same company, his true colors would have unfurled. Thanks for the rules and the insight.

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