We won’t sugarcoat it: collaboration is a buzzword of the highest, buzziest order. Every company and every leader we’ve ever met swears by it, vouching for how essential it’s been in getting them and to where they are today. Yet rarely do we hear, in concrete terms, what it actually takes to create a collaborative environment. Even more elusive is when, as we navigate opportunities to collaborate, we should say yes to collaboration and when we should say no.

We thought this problem needed remedying. So for our #LYBL series with lululemon athletica, we asked three leaders we admire for the honest truth about collaboration. Ambassador of Entrepreneurship for Nigeria and founder of Uncharted Play Jessica Matthews; Head of Social Innovation and General Counsel at Warby Parker Anjali Kumar; and EVP of Business Development & Partnerships at Superfly Presents Chad Issaq shared their insights below. Their hard earned lessons will demystify the cult of collaboration and help you, our dearest readers, know a good collaboration when you see one.

1. Collaboration is NOT Cooperation

For a collaboration to really work, no one can feel like they are compromising, shares Chad Issaq. When everyone involved gets to stay true to themselves, you’ve stumbled upon a collaboration worth keeping.

2. Some Problems are So Complex You Can’t Do it Alone

Tackling sustainable energy in developing nations has led Jessica Matthews to discover that sometimes you just need more partners in your effort. “Your resources, your smarts, none of it matters” as much as having many motivated people working toward the same goal. Importantly, it’s your purpose that ties you together.

3. The No Judgement Zone

Collaboration requires a safe environment for everyone. Be supportive and follow the “yes, and” rule of improvisation to foster a collaborative mindset, suggests Chad. At Warby Parker, shares Anjali Kumar, there’s no judgment and no such thing as a stupid idea.

4. Don’t Force a Collaboration That Doesn’t Make Sense

Because what she does is so damn cool, people are constantly trying to work with Jessica—even when it doesn’t makes sense. When that happens, someone will end up frustrated because their expectations aren’t met. At the end of the day, a collaboration that doesn’t align with your mission or business goals just isn’t worth it. Instead, just support each other! As Anjali told us, “Just because you like someone doesn’t mean you have to collaborate.”

5. Open Yourself Up to Your Blind Spots

When you’re going at something on your own, you don’t know what you don’t know. That’s why Jessica seeks out experts in the areas she’s looking to learn more about, turning them into co-collaborators of her journey. The key is to be open to being challenged. Invite the hard questions and truly test your ideas with collaborators.

6. It shouldn’t be hard

Some collaborations might initially make sense, but somehow everything that can go wrong does go wrong. Maybe it’s bad timing, or maybe you have fundamentally different approaches. But if it’s difficult for you, chances are it’s difficult for your collaborator too. Cutting things off will be a little painful but ultimately, it will be a relief for everyone. Like a great relationships, when things make sense you’ll just know.

On that romantic note, let us know about your collaboration success stories in the comments.


Amanda Sol Peralta

Amanda is Live in the Grey's Editorial Specialist. She is a pop culture fanatic, social media baby and feeler of emojis. Tweet at her @amndsl.


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