Hiring a friend into your company is risky. But if done carefully, it’s possible to work with someone you have an existing friendship with. First, make sure you’re comfortable saying no to the person. If you become that person’s boss, you need the confidence and belief in the other person’s emotional maturity to make the dynamic work. Set proper emotional expectations by saying something like, “I can see some advantages to working together. And yet, I think there are more reasons it won’t work than reasons it will. I’d like to explore the possibility with you, but I want to be clear I think it might not be a good idea.” Then give yourselves a chance to mutually consider how you’ll deal with some difficult situations. This helps both of you set the psychological boundaries you’ll need if you’re to be a boss rather than a buddy. If you can’t imagine yourself holding these boundaries, don’t proceed.

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I got an early start in business. By the time I was 17 years old, I was a partner in a fast-growing company, and when I decided to hire a close friend of my father’s, I was thrilled when he agreed to join.

But it was awkward from the beginning. This man had known me since I was in diapers. I struggled to think of myself as his boss. And so did he. It got really tough when he began coming in late and leaving early, falsifying expense reports, and cutting deals with customers that he didn’t tell us about until after the check was cashed. I agonized over what to do. When I expressed concerns, he would reassure me in a fatherly voice that everything was fine. When I complained about broken rules, he would cajole me about being naïve. After nearly a year of suffering (entirely self-induced), I finally fired him.

I swore I’d never hire a friend again. I reasoned that few friendships could endure such a dramatic shift in relative power and that you can be a friend or you can be a boss, but you can’t be both.

I’ve since grown up quite a bit and, fortunately, learned that I was wrong. I’ve observed and studied friend-boss relationships — and even been on both sides of them — and now know what it takes for them to be successful. The key is having the right combination of patience and candor before and during the hiring process. Here’s how to do it.

Don’t start a conversation about hiring if saying no isn’t an option. Ask yourself, “If I open the question about hiring this person, can I imagine myself saying, ‘I’m not giving you the job’?” If you can’t, you’re doomed at the outset. If you wouldn’t say no — because of your own insecurity or your doubts about the emotional maturity of your friend — if no was the right answer, don’t even consider becoming this person’s boss. Otherwise, you will rationalize or cower yourself into a yes that you’ll probably regret. If you can’t turn your friend down for the job, you’ll never be able to manage them once they’re on your team. If your friend has already opened the question, shut it down honestly. Say, “I don’t think I’m strong enough to do what it takes to be both your boss and your friend.” You may have to deal with some resentment, but if they do resent you, then they’d be the kind of person who would despise you when things cratered.

Give yourself an off-ramp. If you decide to entertain the possibility, set proper emotional expectations by explaining that no is the likeliest result. If the other person’s hopes begin to gallop at the prospect of being hired, you’ve lost already. Don’t conspire in their choice to set their expectations high. Say something like, “I can see some advantages to working together. And yet I think there are more reasons it won’t work than reasons it will. I’d like to explore the possibility with you, but I want to be clear I think it might not be a good idea.”

Rehearse the boundaries. Don’t fool yourself into thinking that being a good friend is a good predictor of being a good employee. Someone who is congenial as a friend can show up as lazy, petty, resentful, dishonest, or even political as a colleague. Let’s face it, you occasionally show up in some of those ways as well. Before you explore the candidate’s qualifications, give yourselves a chance to mutually consider how you’ll deal with some difficult situations. For example, ask your friend how they will feel when:

You override a decision they made.

You give them a negative performance review.

You disagree with them publicly.

They disagree with you publicly.

You press them to achieve an uncomfortable goal or deadline.

You give a plum assignment they wanted to someone else.

You deny them a raise.

Rehearsing these scenarios helps the two of you think through some of the challenges you might face in your new relationship. This helps both parties set the psychological boundaries you’ll need if you’re to be a boss rather than a buddy. If you can’t imagine yourself holding these boundaries, then don’t proceed. In fact, doing so would mean, in essence, agreeing you will subordinate your duty to your company to the interests of your friend. You’ve sold out before you even begin.

I once had a related experience. I was hired as a consultant to evaluate the performance of a senior executive who was also a dear friend. The board of his company had concerns with him and wanted me to make recommendations to improve the situation. The board knew of our friendship but pressed me to take the project anyway. Having learned from my early experience, I let the board know that “no” was an option for me. I told them I wanted to talk to my friend before giving them an answer.

I began our lengthy lunch conversation by giving myself an off-ramp. I let him know that this evaluation was going to happen whether I did it or not and that, if I took it on, the fact that I cared about him could not influence my conclusions. And yet I assured him I would decline the request if he preferred another consultant or felt this would jeopardize our relationship.

In an attempt to rehearse the boundaries of this new relationship, I let him know there was a remote possibility that I would conclude the board should dismiss him. We discussed candidly how we might feel should this happen. In the end, he said, “I would rather have this done by someone I know who loves me than by someone whose judgment or motives I might doubt.”

I accepted the assignment. As the project proceeded, it became terrifyingly clear that there was no retreating from the problems he had created. He had to go. I’d be less than honest if I didn’t admit that I resisted the conclusion longer than I would have had he not been a friend. However, I was far less emotionally threatened by the conclusion because I had set the proper expectations with him. In fact, I count it an honor to have been part of his dismissal. It gave me an opportunity to be part of ensuring not only a just outcome for the organization but also a compassionate transition for him.

It has been a few years since his exit from the organization, and I saw him recently at the wedding of a mutual friend. When we saw each other, what could have been a resentful avoidance was instead a comfortable, mutual embrace.

Hiring friends is risky. But if approached correctly, you can avoid threatening the relationship, and possibly even enrich and strengthen it.