I’ve always struggled with the adage that one should “never mix business with pleasure.” My last three relationships were with guys I met in my professional life. And more often than not, the people with whom I work closely eventually feel like family.
Now more than ever, my work world feels indistinguishable from my personal life. Last September, I mustered the gumption to step into the unknown and left a product management role at Autodesk to start my own business. To buttress the savings that would fund my first venture, customized swimsuits for the masses, I launched a Kickstarter campaign.
While friends, family, and colleagues from around the world generously donated, many did more—reaching out to see how they could help get the business off the ground.
A photographer friend from my undergraduate days shot my look book. A fellow professor at NYU—where I teach Design for Manufacturing as an adjunct—coached me through my pitch deck and executive summary. An extremely patient friend stepped in to provide web salvation after a wrestling match with Squarespace templates left me feeling ancient and technologically inept. A business school classmate helped me do a sales and production forecast as we cackled happily about my break-even point being sooner than I expected. And a fashion designer friend from Los Angeles flew in for a long weekend to help sketch the first bathing suit designs and choose lining colors.
While I can’t speak for them, I had so much fun.
The blurred lines and confusing boundaries of professional and personal relationships, however, can be not-so-fun. There were some incidents that brought to mind another adage: You get what you pay for. There were missed deadlines, illogical excuses, and lack of communication that would be grounds for firing someone. But when a service comes from a friend who is doing you a favor, you let it all go. Working with your friends in this way can cast them in a new light: one that’s sometimes less flattering. And they probably feel the same about you.
I paid contract employees and hired interns, each time with a scope of work and terms of engagement, but with friends, bringing up the need for such documentation is hard. Making it trickier: Much of the help I got came from people in creative fields, some of whom aren’t used to dealing with contracts and paperwork—especially when no money is changing hands.
I spoke to Scott Robson, a life coach who specializes in working with professionals in creative fields, about this particular quandary. ͞He tells me that there is sometimes an innate tension in the way hardcore business people approach a conversation and the posture of a creative, who is bringing so much of themselves to the table. However, there are strategies that can help ease the discussion, he says.
Get the issue out in the open
Try to approach a difficult conversation with gentleness and a focus on co-creating a place of trust. People often feel uncomfortable when they are changing gears into a different mode of conversation—as when going from friendly banter to business talk. It gets awkward. Get their permission to move into a conversation about clear terms, says Robson.
Have a conversation upfront before any collaboration happens. Once you’ve decided you want to work together, gently approach your friend about getting something into writing in a Scope of Work document. Explain how important your friendship is and how you want to make sure things are clearly defined. Also, explain that you want to have the conversation once and get to the fun part: working on something together.
Aim for shared value
Ask your friend what he or she is looking to get out of the collaboration. To build a portfolio? To stretch her skill set to another industry? Fill an employment gap while she’s between gigs? Try to think of ways you can help your friend with her goals and build that into the scope.
Watch your language
Work with your lawyer to craft contract language that’s less intense. My lawyers knew that I’d be contracting a lot of help from creatives and made the language in my terms as human as possible. Changing ͞ “The Undersigned Parties” to “us,” for example, makes the document feel a lot less aggressive. This is definitely something to consult your attorney on, since you don’t want the tone to compromise the effectiveness of the contract.
Create an easy out
Phrase the work engagement as an experiment. I had a lousy experience working with one of my friends. When we debriefed, I explained that I viewed the project as an experiment that just didn’t work out. I told her I was glad we tried, but that I thought we made better friends than colleagues. This helped us switch gears and we both left the conversation in a positive way.
When it doubt, just hire someone
If you’re unsure about whether to ask a friend for help, do some research on the hourly rate for someone with a similar skill set. Go on Glassdoor or Freelancer.com and put up a bid to see if there is someone—maybe in a less expensive market—who can help out. The cost may be lower than you thought—especially when compared to the cost of losing a friend.
Bootstrapping is tough—but it can also be fun. I see collaborating with friends the same way. It can be a great experience for both of you—if you’re clear and thoughtful about insuring that both friendships and business interests are protected.
Sarah Krasley is an entrepreneur and founder of Unreasonable Women, a NYC-based company focused on products, services, and workplace policies that empower women. Her current projects include custom swimwear and a code of ethics for photo retouching.