How to Be Friends with Someone Who Works for You

Executive Summary

When you’re friends with an employee, you must navigate some difficult terrain. One of the most difficult aspects is walking the line between confidentiality and transparency. How do you keep confidential information about the organization — or even your friend’s job — to yourself if they may become offended, upset, or hurt? Start by setting your friendship up for success. First, choose your friends carefully, ensuring that you both are mature and have enough self-esteem to build trust over time. Then set expectations at the start about what you can and can’t share. Be clear, too, in your roles in conversation, whether you’re talking in “work mode” or “friend mode.” Then, be transparent with others in your organization about your friendship. Finally, do your job, even if it requires difficult conversations.

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Nadezda Kozulina/Getty Images

Working as a senior executive can be a lonely job. You have to deliver tough messages. You can’t always be transparent about your own challenges. And you must keep key decisions confidential until the timing is right.

There’s no way to escape the necessary burdens of authority. And, from time to time, you may develop a friendship with someone in your organization. It’s one thing to have a peer-to-peer friendship at work, but another to have a power imbalance with your friend. Can you be friends with someone who works for you, especially when your role requires you to harbor secrets from them?

Consider this example: Mariah and Einat became friends over a dozen years ago after they discovered their shared love of outdoor activities. They’ve hiked and backpacked and taken long bike rides together. Together they have survived some sharp rocks, literally and figuratively, in their friendship.

But Mariah and Einat started out in a different relationship. Mariah was a vice president of their company and Einat’s skip-level boss. Einat was a senior director in Mariah’s group. Clearly any manager-employee friendship is fraught with traps. You might damage either the friendship or the working relationship. Other staff may withhold valuable feedback about the employee if they sense you’re friends. You could lose trust with your friend and with the rest of your staff if you’re not careful about walking the fine line between confidentiality and transparency.

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Friendships

In her role, Mariah often knew information that would impact Einat’s job, including possible layoffs and promotions. Even though they were close friends, Mariah had to keep this sensitive information confidential. Mariah trusted that Einat would understand the constraints on transparency because of their roles at work. When I talked with Einat, she did understand and called it her “suck-it-up muscle.”

Not every employee has this muscle, though, and they can become offended or hurt by withheld information or negative feedback. And not every boss knows how to navigate the fine line of how much to share and when. But there are ways you can set your friendship up for success. Here are five tips on how to manage a friendship with one of your employees.

Choose your friends carefully. Many of us heard this advice when our moms kissed us goodbye for our first day of kindergarten, but it’s especially important at work. Having a friend who is a subordinate requires high degrees of trust and judgment on both parts. It’s not possible with every work relationship. Mariah points out that both parties must be mature and have enough self-esteem to build trust over time. “It’s really not rocket science,” said Mariah, “just impeccable communications and boundaries.”

Set expectations at the start. You will have knowledge and responsibilities beyond your friend’s role and clearance, and your friend needs to know that. Be transparent up front about what you can and can’t share. I didn’t follow this advice earlier in my career and instead simply made an assumption. When I was working with my peers on our management team on a company reorg, I knew my friend Alice would be affected. But I wasn’t her manager, and I had to keep the information confidential. After the changes were announced, Alice was upset that I had kept the reorg from her. I had assumed it was obvious that, even though we were friends, I couldn’t share any information that Alice didn’t have access to in the normal course of business. It wasn’t a matter of trust; it was a matter of ethics. And sharing the reorg information prematurely would have also put Alice in an awkward position with her peers who were in the dark. In retrospect, establishing boundaries with Alice may not have made the reorg easier for her, but it would have avoided any tension in our relationship.

Be clear about your roles in conversation. Explicitly setting norms together for how you will work and play creates equality and equanimity in your friendship. Whether you’re in a one-on-one conversation in the office or hanging out together after work, be transparent about what kind of conversation you’re having. Say something like, “Let’s talk about this in friend mode.” Or, “Here’s a work topic that I’d like to bring up and get out of the way first.” But also check if it’s okay with your friend to have that conversation at that moment. As a manager, you might say, “I want to find out how things are going with your project. Is this a discussion we can have right now?” This allows your friend to have an equal say in what topics are discussed when.

Be transparent with others. Since Mariah was two levels above Einat, when she was in meetings with her direct reports, she would recuse herself on discussions about Einat’s pay. Mariah would state clearly that she and Einat were friends, so she didn’t want that to influence the team’s decision making. Others might feel awkward disclosing their feelings about your employee, especially if they have negative feedback. They might wonder if you’ll hold their comments against them, or if you might unduly influence the outcome of the discussion. On the other hand, you might know more than you’re supposed to bring into the professional setting. Mariah noted, “I wanted to be careful that my inside information wouldn’t be taken out of context.”

Do your job. Be direct and prompt in communications — especially when it comes to negative feedback or unpleasant news, like a layoff. Even if you’re afraid of hurting your friend’s feelings or fear they might get defensive, speak up, but be prepared that there may be rocky times or even long breaks in your relationship. As you wrap up the discussion, let your colleague know you want to be friends, but give them space to make their own decision about whether they also want to maintain the friendship. For example, Ben and Ravi had been friends for many years when they began working together. Ravi was hired as Ben’s manager. After a couple of years, Ravi had to tell Ben that Ben’s job was being eliminated. Ben said, “It was challenging for each of us. He didn’t want to have to tell me, of all people, that I’d lost my job.” After leaving his job, Ben remained friends with Ravi because he realized Ravi’s decision was business, not personal, but it took Ben some time before he could come around to that mindset.

Friendships are based on mutual trust and transparency. Navigating manager-employee friendships is tricky, especially when, as a boss, you’re privy to information that your employee is not. The work friendships that survive are also based on trust and transparency: transparency about the boundaries within which you will be able to communicate and trust that your actions are professional, not personal.

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