Increasingly, I receive a lot of pitches for collaborations. I am also increasingly picky about which collaborations I say yes—hell yes!—to. I say no to a lot of proposals. As I’ve half-joked recently, I am pickier about who I collaborate with than who I have sex with.
I’ve developed high standards about who I collaborate with, when, and why. That’s because, in my mind, a collaboration is a high-risk, high-reward endeavor. Depending on the project, a collaborative project can easily take many hours, days, weeks, months, or even years. If it goes well, you enjoy the process, make something you’re proud of, that serves your goals and benefits the world. But it can also… not go well.
It might not be fun, after all. It might get drawn out, and become a sink of time, energy, and resources. At its worst, a poorly structured collaboration can strain, severely damage, or even end a friendship.
It’s relatively easy to propose a collaboration: “Hey, we could work on something together!” But in my experience, it takes considerable thought, care, and effort to structure a collaboration so that it’s a fun, useful, win-win exercise. In other words, there’s an art to collaboration.
In many cases, if someone pitches me on a collaboration, I’m a yes to them, but not to the specific project or proposal. I like the person, our missions and goals feel related and mutually supportive, and I’d like to do something with them—but not this particular project, or not in the form it’s been proposed to me.
Here are some of my implicit heuristics that make me more likely to say yes to a proposal for collaboration:
- We have mutual friends and collaborators who speak highly of you. Your reputation precedes you.
- We’ve actually met / had a conversation before (online or in person). We both enjoyed our conversation and connection. It feels good, fun, easy, vibey to spend time with you.
- I don’t sense that you need or want anything from me, are trying to use or manipulate me, get something out of me, or see me as a concept in your mind. (see Requests and Relationships)
- You demonstrate that you do what you said you would do, by e.g. showing up on time, sending a calendar invite, following up with that article you said you’d send along.
- We have shared context on each other’s vow, vision, values, current projects.
- You show that you understand me, my vow, projects, goals in an important way. You know about The Service Guild and the three pillars of my life’s work (Love, Curiosity, and Empowerment).
- Our visions and goals overlap in an obvious way (not just because you say so).
- You have demonstrated expertise in complementary skills to mine. You are believable.
- When you pitch me on collaborating, it’s not out of nowhere. We have established context for it and it’s the obvious next step to both of us.
- You pitch a project with a clear purpose, scope, project plan, and roles for each of us. I don’t have to think much to see it’s feasible; I feel its resonance clearly, and it feels fun and exciting in my body.
- The project isn’t too big, it’s proportional to our relationship and shared experience and expertise. It doesn’t feel risky, I don’t need to place any big bets. It won’t take large amounts of time or effort or money, esp. for a first project.
- If we’ve collaborated before, I enjoyed it immensely, it went well, we both learned and grew from it, I’m proud of what we did, and this is a logical, intuitive next step for our collaborative relationship.
- Above all, I like the thought and feeling of spending time with you, collaborating with you.
I hope that this list will help you to make project proposals that your collaborators say yes to, feel good about, and that you both find rewarding—or to pitch me in a way that I’m more likely to say yes to 🥰
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The art in this post was created by Sílvia Bastos, and is licensed under a CC BY 2.0 license. You can support her work on Patreon.
