While collaborations in the corporate world are now all the rave. Creative collaborations have a long history of success.

And as a creative business owner, collaborations are a great way to:

• build your business
• grow your brand
• increase revenue
• expand a personal creative project
• boost your creative juices

If you’ve ever participated in a successful collaboration, you know that there’s a certain magic to them.

A good collaboration is not just a sum of the parts. It’s not just each of you bringing your strengths to the table. It’s not just each of you helping the other with her weaknesses.

A successful collaboration allows you to play off each other and create something bigger.

While the start of a collaboration can be really exciting, most collaborations also end at some point.

And the ends can range from a happy parting of ways to a fiery crash. (? And to save all our lives you’ve got to envision, The fiery crash MUSIC ?)

How to increase the likelihood of a successful creative collaboration

Over the past eleven years, I’ve help end as many collaborations and partnerships as I’ve helped start.

Want my biggest takeaway? It’s this…

Dig into the hard questions at the start of a collaboration to increase your chances of leaving the collaboration on good terms.

And just like marriage (or so I’m told), entering into a creative collaboration or business partnership by having tough conversations at the onset is the best way to make sure:

• it’s a good fit
• you can gracefully work through things when life throws you a curve ball

Are you a good fit?

Digging into these hard questions before you invest a lot of time, energy, or resources into a collaboration will assure that you both have the same goals, expectations, and direction for this project.

It’ll help you decide if you:

• have similar working styles
• communicate well
• trust each other
• can compromise and work through problems together
• enjoy each other’s company
• share the same vision for the collaboration
• have similar levels of commitment to the project

Some people just aren’t a good fit. And there’s nothing wrong with that.

So if you can suss out this sooner rather than later, it’ll help assure you don’t despise each other several months down the road.

Life changes

Even though we wish things stayed static, they don’t. Things are constantly and consistently changing.

Some of these changes are small and you’ll be able to work through them. But some are major life-altering changes. And if these come up, your collaboration might not be able to work through. I’ve seen collaborations end over things like:

• parents getting sick
• cancer
• a mental health crisis
• children being born
• children starting elementary school and college
• moving cities and states
• one collaborator shifting her priorities
• one collaborator discovering new interests

And if you can talk about how you’ll gracefully exit or deal with tricky situations when you are excited and embarking on a relationship, you are less likely to leave the situation feeling hurt, frustrated, or taken advantage of.

Because, according to clients who have gone through both, dealing with a business divorce is just as stressful as a marriage ending.

Questions to ask a business partner or collaborator

To make sure that your creative collaboration is starting off on the right foot, there are seven topics I’d encourage you to work through with your collaboration partner.

These topics will help make sure you are a good fit to collaborate and that you’ll both enjoy working together.

When you sit down to discuss these questions, I’d encourage you to do it over a meal. (And if you can, this study from University of Chicago says that sharing plates is even better!)

Here are the seven topics you should discuss:

• What is our goal for this project? What does success mean for this project?
• How do you see us getting there?
• How would we share the workload?
• As time goes on, do you see our workload shifting?
• What happens if life changes and one of us needs to leave (or reduce her involvement)?
• What roadblocks would make us throw in the towel and end the collaboration?
• We are going to be creating awesome stuff! When/If this ends, how can each of us use what we create for individual projects?

What is our goal for this project? What does success mean for this project?

It’s important at the outset to make sure you are both on the same page about your goals and how you’ll be defining success.

If one of you wants it to be a fun side hustle, while the other wants to have the product you create in stores nationwide, then you might have a mismatch. (Or need to agree on how to divide the workload.)

How do you see us getting there?

No matter how you define success, there will be a million ways to get there.

Maybe one of you wants to employ a slow and steady growth method where you build strong individual relationships with your customers and audience members. But the other wants to utilize Facebook Ads to quickly scale an audience. Again, neither approach is wrong, but in the same strategy, these tactics will be at odds.

How would we share the workload?

Of course, in most collaborations, you are willing to pitch in and help out where needed.

But it’s usually best to define who should have primary responsibility for a task.

Some of these will be easy to assign because they’ll play to each of your individual strengths and the reason you want to collaborate. But others, especially those that very few people enjoy, like bookkeeping, might be harder to agree on.

As time goes on, do you see our workload shifting?

Often at the start of a collaboration, you want to run a lean and mean ship. You want to figure out if it’s going to be successful, enjoyable, and resonate before you invest in new equipment, team members, or hiring experts.

But as time goes on and you start achieving success, this might change.

Maybe both of you hate bookkeeping, but you agree to switch off months until the collaboration becomes financially sustainable. But you agree, that your goal is to pass this task off to someone else.

Maybe for now you’ll handle shipping yourselves. But you want to hire a production assistant to help you pack and ship orders as soon as your revenue hits $5000 per month.

What happens if life changes and one of us needs to leave (or reduce involvement)?

Life changes. And when that does, the time and energy one collaborator has for the project could shift.

This might come about suddenly, like if you get sick or injured. Or it might be something you can plan for, like the birth of a child.

Either way, it’s good to discuss how you’ll handle this.

I’ve seen collaborations handle this lots of ways.

• Some collaborations plan for one collaborator to buy out the other
• Some plan on trying to find someone to step in
• Others plan on hiring help and reducing the pay of the collaborator that had to step back

What roadblocks would make us throw in the towel and end the collaboration?

It’s also good to understand what situations would one or both of you want to end the collaboration.

This can happen for scary reasons like one collaborator dying. But more frequently it’s for reasons like:

• collaboration is only expected to last for a specific number of months/years
• collaboration will end if it doesn’t generate enough revenue to make it sustainable
• collaboration will end if doesn’t generate enough interest

We are going to be creating awesome stuff! When/If this ends, how can each of us use for individual projects?

Finally, since you are creative people, you should discuss how you are going to handle the copyrights, trademarks, and other intellectual property that’s created during your collaboration.

The short version is that collaborations often handle this in one of three ways:

• one collaborator owns the copyright and licenses it to the collaboration to monetize
• collaborators co-own the copyright as a joint work
• collaborators co-own the copyright in the collective work that the collaboration creates

How to initiate the conversation

First off, you aren’t alone in trying to justify that it’s okay to skip this conversation.

You might tell yourself,

• We are friends, what could go wrong?
• If I broach the subject, she’ll think I’m trying to have the upper hand.
• If I broach the subject, she’ll think I don’t trust her.
• I’ve done these before and everything worked out fine, why won’t it this time?
• I don’t even know where to start, so I don’t want to say the wrong thing and harm our relationship.
• She’s got more experience than I do, so I’ll just let her bring it up if it’s really important.

But skipping the conversation, however awkward it might be, is the best thing you can do for both of you in the long run.

(And isn’t learning that you shouldn’t be collaborating a better thing to do sooner rather than later?)

So how do you broach the subject?

My biggest tip is my standard negotiating tip: frame the conversation as something that benefits her not you.

If you’ve never done this before, you could say:

I’m super excited to work together, but since I’ve never done this before can we sit down and talk about what you need from me to make this successful? I don’t want to disappoint you by not doing something that is supposed to be on my plate.

If she’s never done this before, you could say:

I’m looking forward to this collaboration! I know that this kind of collaboration is new to you. Should we sit down and talk through how we can leverage both of our strengths?

If these kinds of collaborations are old hat for both of you, you could say:

I know that we’ve both done this kind of thing tons of times. Let’s sit down and make sure we aren’t doing double work and wasting time and resources.

Or no matter the situation you could say:

Hey, I’m really looking forward to this. Can we sit down and map out how to make this successful? And how I can best support you in this collaboration?

(Psst…if you really need a fall guy or you get pushback, I’m happy to be the bad guy. You can tell her I said you need to have the conversation.)

TL;DR

If you have a business partner or collaborator, I challenge you to send her an email with these seven questions and schedule a lunch date to talk through them.

• What is our goal for this project? What does success mean for this project?
• How do you see us getting there?
• How would we share the workload?
• As time goes on, do you see our workload shifting?
• What happens if life changes and one of us needs to leave (or reduce her involvement)?
• What roadblocks would make us throw in the towel and end the collaboration?
• We are going to be creating awesome stuff! When/If this ends, how can each of us use what we create for individual projects?

That way if you have irreconcilable differences, you can either pull out and remain friends or figure out a way to reconcile them.

Do you know someone about to embark on a new relationship? Then please share these questions with them, so they can nip any problems in the bud.