Friends With Professional Benefits: 8 Things To Consider Before Working With Friends

Working with a friend might seem like a great idea at first glance, but go deeper. Is it really all it’s cracked up to be?

Before I dedicated myself to being a freelance writer, meditation teacher and self-care coach, I worked for a period as a virtual assistant. I got my start in that field through a friend. At that time, she was my best friend. So when she asked me if I did that kind of work and how much I’d charge, I didn’t give working with/for her a second thought. We were best friends, we got along great — why wouldn’t working with her be just as wonderful?

Unfortunately for me, that situation didn’t work out so well. I’m no longer friends with her, and we don’t work together anymore. But I have had some successful business relationships with people I consider friends. Because of that, I believe that working with friends can work — if you follow a few simple rules.

Photo by Alexander Mils on Unsplash

Never let a friend be your sole, or biggest, source of income

When I worked with my friend, the work I did for her made up about 50–60% of my income. So when the working relationship ended, I lost half my income in an instant. As a single mom with two kids to support, this was an absolute disaster.

Depending on what kind of work you do, this may not even be an issue for you. Writing, meditation and self-care coaching, for example, all ensure that my income is diversified through many clients. The loss of one might be a hit to my bottom line, but it can’t destroy it. But if you’re a project manager, for example, who can only work with one or perhaps two clients at a time, it can prove catastrophic.

If working with your friend would be a sole source of income, or the largest chunk of your income, consider very carefully whether you want to move forward with that decision.

Don’t let friendship override the professional side of working together

I’ve talked to people who worked with friends and found that the friendship often overrode the professional aspect of working together. One person explained how a client had gone through a particularly rough patch in their life — ending a romantic relationship, moving across country with their child, and starting all over in a 9–5 job while running what had been their full-time business as a side hustle again.

They cut their client some slack on a final unpaid invoice because they were sympathetic to what the client was going through. But they reached out after a couple of months and the client claimed to have forgotten there was an outstanding invoice and promised to pay within a week. Several months later, the invoice was still unpaid.

This person was now forced to decide whether they valued the friendship more than they needed the income. Moving forward with collection procedures felt harsh, but they didn’t see any other options. They ended up ending the friendship and putting the former client into collections in order to get the income they needed.

If you’re going to work with a friend, you have to be able to balance the personal with the professional, so you don’t screw yourself or your friend over.

Photo by Gean Montoya on Unsplash

Work personas can be very different than friend personas

As a friend, she’s awesome: supportive, generous, loving, funny, and someone to count on. As a boss/client, she’s less so: she tends toward flaky, unreliable, demanding, confusing, and frustrating.

Through the lens of friendship, we might see a person who has their life totally together and is incredible. But through the lens of working together, we often get a much different view. We can see someone who doesn’t know what they’re doing, feels overwhelmed, or is a harsh taskmaster that has no resemblance to the loving and kind friend we adore.

If you want to work with a friend, I strongly recommend a trial run first. 14 or 30 days to see how it goes, at full pay, and with both of you having the option to call it quits. Give both of you the easy out so you don’t feel obligated to stick around later.

You need open communication

Open communication needs to be more than just the promise of it. You both need to feel comfortable being completely honest about what you see. You need to be able to speak up when your friend is being inconsistent or too demanding, and they need to be able to speak up if you’re not living up to your responsibilities.

Friendship can really cloud the working relationship when it comes to communication. Where we might not hesitate to tell a boss they’re demanding too much of us or they’re not doing their job properly, it’s often harder to offer the same constructive criticism to a friend. And even when we can say it, we might not do it as professionally as we should, because we feel comfortable with our friend.

This is another reason to do a trial run before committing to working together. If you’re only committed for a short period, you can push through things that might otherwise irritate you too much and walk away at the end of the trial period without hard feelings.

Photo by Adeolu Eletu on Unsplash

Set ground rules and put them in a contract

Because it’s so easy for the lines between work and friendship to get blurred, a critical component of working together is setting clear ground rules and putting them in a contract. At a minimum, you should include:

· Work hours (both the schedule of working hours and how many hours are contracted)

· Work duties (including task names and descriptions)

· Pay rate (and whether it’s per hour, task, project, etc.)

· Rules such as allowing 24 hours for responses to emails, appropriate methods of communication of work duties, etc.

· A termination clause (including how many days notice is required, termination fees, and reasons to terminate without notice/fees)

Of course, you may find yourself getting screwed over by a friend who ignores the contract and contacts you at all hours or tries to get you to do work outside the scope outlined. They might ignore the termination clause and not give notice. Or you might decide to ignore your own contract in favor of saving your own mental health because the friend turned out to be a nightmare client.

But if you have the contract, you have protection should you need it. If it comes down to going to court, you’ll have proof rather than it being your word against your (former) friend’s.

Draw clear boundaries between work and friendship

You’re enjoying a girls’ night out and it’s about to be your turn for karaoke when your friend/boss/client says, “Oh, hey, I need you to get that paperwork to Melissa first thing in the morning. It has to be there by 8 AM, so you should probably make tonight an early night, okay?”

No, not okay. You need to have clear boundaries between the working relationship and the friend relationship. If you’re hanging out as friends, there should be no mention of business. If you’re having a business meeting, aside from the typical friendly conversations about how you are, how the family is, and how your weekend was that anyone might have, you should refrain from talking about your personal life.

If you mix business and friendship, you end up with two problems:

· You’ll work when you should be off the clock

· You’ll question billing for work meetings because you discussed personal situations

And those two problems can lead to a third, which is a client who expects you to be available 24/7 and a friend who feels slighted if you ignore their calls or texts because you think it’ll be about work.

Photo by Gratisography from Pexels

Embrace healthy, honest conflict

If you disagree with your friend/client, you need to be able to say so. The same goes for them. But it must be done in a healthy, honest way. This can be problematic because conflict in friendship and conflict in the workplace are handled so differently sometimes — and you’re dealing with a mix of both.

Often, in this situation, you’re dealing with two small businesses (yours and your friend’s) that don’t have an HR department or any other employees who can step in and help mediate the conflict. It’s just you and your friend. And that can make it even easier to slip from business to friendship and say things that are unrelated to work or incredibly hurtful.

You might want to consider finding a counselor that you and your friend can either meet with regularly to air things out, or who can meet with you in times of professional conflict. This can give you a third party to keep things on track and find resolution without trying to create a position in either of your businesses that you’re not ready for. If you go this route, split the cost of the counselor equally so that no one can feel they’re being slighted because they pay less if they’re told they’re in the wrong.

Trust is key

Whether you’re the boss/client or your friend is, trust is key to working together. By working together, you both have to essentially trust each other with your businesses. You both need to trust each other not to make poor decisions that would leave the other hanging, to follow through on promises you each make, and to be open and honest about everything business-related.

But you also should to be able to trust each other to keep friendship issues from affecting the business relationship and vice versa. It can be a narrow line to walk, and you need to be able to trust each other to do your best to stay on it. And if you fall off, you must trust each other enough to know that it’s not intentional when lines get blurred or crossed completely.

Without full trust, both the working relationship and the friendship are likely to fall apart. So if you feel that you can’t embrace full trust across the board with your friend, you should probably take a hard pass on working together.

Photo by Thought Catalog on Unsplash

Are you ready to work with a friend?

It often feels like working with a friend is the perfect plan. You gel so well as friends, it should make business smooth sailing. You don’t have to get to know someone new or do a bunch of interviews. Why not go for it?

But there are some harsh realities to working with a friend. The biggest of those realities is that if it falls apart, you stand the chance of losing two relationships instead of just one. Before you take that leap, and risk it all, make sure you’re okay with the potential outcome.

Single Mom Coach | Meditation Teacher | Relationship Writer | | Newsletter:

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