Career Hacks

How to Hire Your Friends Without Wrecking Your Friendship

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When you are a brand new entrepreneur hustling for all you’re worth, you probably don’t have the money to hire out for help. Now, you can usually find a pretty great professional for one-off jobs. I hired a wonderful local photographer on Elance, and I met the #GIRLBOSS who did my logo and branding by sheer happenstance (we were both at a Craigslist roommate meeting and didn’t end up living together, but things still worked out!).

But sometimes, you get really lucky, and you have a friend with a useful skill set: web development, photography, copyediting. The question is, how to work together without sabotaging your friendship?

I hired one of my best friends to do web development for my new business, Bluestockings Boutique, which just launched twelve days ago. This is how my friend and I worked together for seven months while preserving our friendship.

Compensation, Compensation, Compensation

Your friend is an expert. This is why they’re helping you! Pay them. Even if they say you don’t have to. Even if it’s only a fraction of what they’re worth. Even if they say they feel bad about taking money from you when you’re barely off the ground. Even if you can barely afford it.

Keep things professional. You will both feel better about this later.

Set a Schedule

“When should I get this done?”
“Oh, whenever!”

That conversation is a recipe for disaster. Be clear about your projected deadlines and your hard deadlines. Be honest with each other about how long you think tasks are going to take.

Segregate Your Communication Channels

Find something that isn’t text or email to communicate about your project. Separate work time from friend time as much as possible. The last thing you want is for them to look at their phone (or vice versa) and go “Oh, them again.”

My friend and I used a shared Trello board for communication about the website – in fact, we still use it for ongoing notes to each other about tune-ups and small things that need to be taken care of. The important thing is finding a communication tool you can both agree on and that you both feel comfortable with.

Respect Their Time

This is related to setting a schedule but deserves its own category. They might be your friend, but this is a work project. Are you out for drinks and dinner with friends? Don’t talk about the project the whole time. Don’t start texting or Trello boarding them at 9 p.m., desperate for a response when they’re in bed with Netflix or their partner or their dog or all three. Similarly, if they say they don’t have time to do something, drop the subject. Don’t push them; don’t guilt them. Respect their boundaries.

Learn How to Do Stuff

They’re your friend, so you’re probably getting a bit of a deal on whatever it is they’re helping you with. And you’re a badass hustler, so you should probably learn some more self-sufficiency anyway! Do you run to your friend every time you have the littlest question about whatever it is they’re helping you with? Learn to Google or watch youtube videos or look at help boards for whatever it is you’re using first.

Your friend is helping you during this exciting, vulnerable time, and they are amazing for that, but ultimately, it’s up to you to take the reins and be responsible for every part of your business.

One last word of advice that should probably go without saying: don’t work with anyone you can’t be real with. All of this is useless if you can’t be honest about things like boundaries and how you’re feeling. You want to make the best choice for your business, but you also want to make the best choice for yourself.

Jeanna Kadlec

Jeanna Kadlec is the founder of Bluestockings Boutique, an online alternative lingerie boutique whose motto is "underthings for everyone." For the last four years, she has called academia home. You can follow her on Twitter at @BluestockingsBo.

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  • Vienne Cheung

    I agree completely, particularly on this piece: “One last word of advice that should probably go without saying: don’t work with anyone you can’t be real with.”

    For me, the fundamental question I ask myself when hiring a friend is “Will this person understand that my business is crucial to me? And will this person do whatever it takes to help me out?” Say for example: If my office building was on fire, will this friend drop everything to help me get out of this rut, or will he or she have something “more important” that will get in the way? Although I understand that this is kind of an extreme example, but on the other hand, they are also not. For myself, these are the standards that I hold for myself, and I know I will be there for my friends.

    If the answer to those questions are “No”, then I’m probably better off hiring someone else, or spending time with a not-so-fair-weathered friend.