How to Build a Crew

I’ve spent the last several years building a crew of friends and collaborators to work on projects with. Our crew is called The Service Guild.

Finding these friends and learning to collaborate together has been a major goal of mine for the last several years. Having a crew I love, respect, trust, resonate with, can coordinate and collaborate effectively with, makes me feel wealthier than having any amount of money, owning any possession. It is one of the greatest blessings in my life.

I love having a crew. I love The Service Guild. I love my friends that are in it—Mary and Zev and Kristijan, Bee Eye and Rosie and Aspen and Vincent, Abi and Anansi. I love spending time with them, and I’m so proud of what we accomplish together.

Art by Sílvia Bastos

It isn’t easy to build a crew, and I’m definitely not perfect at it. But in this post, I’ll pass on what’s worked for me with The Service Guild, in case it’s useful to others who want to find and build a crew of friends to collaborate with.

When It Works: The Magic of Resonant Crew

Many of us have memories of working on group projects that made us miserable. Maybe it was at school. For me, it was that middle school physics project, giving a presentation on alternate energy and solar panels, where I did all the work and my “teammates” got a good grade as a result, too, despite doing very little.

I’d rather work alone than have that experience again. There’s a lot I can do by myself. I’m pretty capable. But there’s a limit to how much I can do myself, independently. For some of the ambitious, cool projects I dream of doing, I’m simply going to need collaborators: people who have skills and talents that I don’t, that extend what is possible for me.

With the right collaborators—skilled collaborators who are enjoyable to work with, who have similar values and visions—working together means that U can make something impressive, inspiring, cool together—and have a blast doing it. And thankfully, this is an experience I’ve been blessed to have, again and again.

Sure, working alone beats doing a collaborative project with the wrong context or collaborators. But working with a team of people U love, admire, respect, and enjoy spending time with, who extend ur capacities and what is possible, blows working alone out of the park every single time.

With the help of skilled, fun collaborators who I enjoy and respect, I’ve made animated music videos, dance tracks, dance parties, in-person retreats and events, audiobooks, and more—all things that would have been difficult, if not impossible to do by myself—and certainly it wouldn’t have been nearly as much fun.

For me, there’s nothing quite like the feeling of pulling off a project like this—of seeing it through, of watching the impact on other people, of looking my collaborators in the eyes and knowing: we did it.

I know that building a crew like this is possible for U and ur friends, and I want this post to help U to explore what that might look like.

Start Small: The Art of Micro-Collaboration

I think U are ready to explore crewing when U have simply hit the limits of what U can do by urself—when U have ambitious projects U want to do, but know U can’t do them all by urself. Alternatively, U are ready to start simply when U have a friend or two or ten U would be interested in collaborating with!

“Small collaborations first!” has become a core principle of mine for collaboration. When U find a potential collaborator, it helps to start small, with collaborations that take a day, a week, or a month, rather than months or years.

A small collaboration is one that can be done in a short time (typically a day or a week), at low cost (ideally free), with low effort (a small number of hours, a reasonably easy difficulty level), and is, above all, safe-to-fail. That means that even if it goes poorly, nothing irreversibly bad will happen.

Some examples of small projects include:

  • a podcast conversation
  • co-authoring a blog post
  • hosting an hour-long Zoom call

Some examples of projects that are not small include:

  • starting a company or non-profit
  • planning a week-long in-person event
  • building a web app together

Even though the project itself may be small and simple, U are testing and exploring the strength and resonance of a particular collaborative connection. And that is something complex, emergent—something that has to be discovered with time, together. Keeping the project short, simple, and sweet makes that easier.

Make sure the collaboration is going to be something that is win-win, too. Consider not only ur benefit, but the joy and growth of ur collaborator(s). I recommend reviewing these Questions to Consider Before a Collaboration to help U pitch a collaboration. They’re less a laundry list of questions U absolutely have to have figured out beforehand, and more a number of variables to consider and weigh together.

See how an initial collaboration feels, and take time to reflect on it afterwards. Did U have fun? Did U learn and grow? Are U proud of what U made? Would U want to do a similar project again? Would U want to collaborate with each other again?

This reflection can happen individually, informally, but it can also be useful to do collectively, formally—with a formal retrospective. At The Service Guild, we have a retrospective SOP we do at the end of major projects that includes:

  • Opening with check-ins and intention-setting
  • Reviewing successes and moments we’re proud of
  • Reviewing challenges and obstacles
  • Identifying lessons learned and improvements for future projects
  • Closing with remaining shares and action items

We’ve found doing retrospectives to be a best practice that balances celebration of individual successes and wins with honest assessment and feedback about how we could improve at any level. These conversations help us to improve over time on multiple dimensions.

Some collaborations will go poorly objectively (“well, that didn’t work”). Sometimes U will learn that some collaborators aren’t a good fit, for any number of reasons. That’s part of the process. U will gain more clarity over time about who U like to work with, and what kinds of projects are life-giving and generative. Repetition and iteration will improve ur discernment and help U to make better choices individually and collectively.

One simple way to frame my approach to building a crew would be in terms of my friend Visa’s Do 100 Thing: Do 100 Collaborations. I haven’t been counting, but I’ve certainly done this many or more collaborations over the last five, six years.

Most of those collaborations should be small, safe-to-fail experiments. Once U’ve done a number of small collaborations with someone, U can move on to trying a medium-sized collaboration. And similarly, once U’ve done a number of medium-sized projects together, when U both feel ready and eager for it, only then should U graduate to trying a large project together.

It’s very, very easy to make the error of biting off more than U can chew. Even if it’s theoretically possible to accomplish a large project together right off the bat, starting small helps U to develop shared sensibilities with ur collaborators about how U like to collaborate together, in a lower stakes environment. And if it doesn’t work out or feel good with a small project, it’s definitely not going to be fun or effective to work on a big, huge, long-term project together.

Instead, start small. Small collaborations first!

Qualities to Look For in Projects and Collaborators

At the scale of having done ~100 projects—with that many projects, and a large variety of collaborators—it becomes possible to notice certain trends: including what projects U like, and which U don’t; which collaborators are good to work with, or which ones are more challenging to work with, and why.

In terms of projects, I’ve discovered that I essentially want to be balancing five qualities, which we talk about in The Empowerment Department when we are helping other people with their own projects:

This is a pattern that emerged over time, and has been quite stable since we made explicit. We discuss this diagram and these qualities more extensively in our post on The Ideal Service Project.

Similarly, I didn’t know what I was looking for in a collaborator when I set out, but I have a much better sense of what I was looking for now. I value collaborators who are:

  • fun to be around, whose company and presence was pleasant and enjoyable—who I would genuinely want to be friends with. As I’ve said before, a project is partly an excuse to work on something fun with people U love and enjoy spending time with—so make sure U know who those people are.
  • kind, friendly, with good ethics. I can’t abide people who are mean or cruel, or purposefully unkind—so I don’t want to work with them, either.
  • high integrity, reliable, do what they say they would do (DWYSYWD). Are they on time for calls or meetings that they schedule, or are they late—or worse, do they miss them entirely? If U make an agreement to do a certain task or follow up action items after a call, do they follow through? If something changes, do they communicate that in a timely fashion, and negotiate something workable for all parties?
  • skill and competence—do they have a set of skills that compliments urs, that they are highly competent, excellent at?
  • intrinsic motivation, desire, ambition, goals—are they self-starters? Are they motivated to move forward on things that they care about and commit to, that are aligned with their goals? Do they do work and projects of their own accord, or only within a context of being told what to do, e.g. a corporate job?
  • growth oriented—are they interested in growing? If U ask them about their growth edges, do they know what theirs are, and have a plan to work on them? Do they demonstrate a desire to grow over time, and put in work to do so?
  • mission-aligned—do their prior work and current projects have common themes that are aligned with, resonant with ur own?

Plant Ur Feet, Articulate Ur Vector, Build the Crew

if U plant ur feet firmly in the ground for something good, help will arrive

I think U are ready to formally form a crew when U have clarity about what kinds of projects and directions U want to work on, or clear, consistent resonance with specific collaborators, such that U want to work with them on an ongoing basis.

The people U work with and the projects U choose mutually clarifying and mutually supportive. U decide together what direction to go in.

Visa talks about “articulating your vector”—being able to state clearly what U are doing, and why, in a way that is understandable to others, so that they can contribute.

When I talk about Love, or Curiosity, or Empowerment, these are vectors, clear themes that resonant people will understand, resonate with, and want to contribute to.

If U’ve done loving-kindness meditation before, if it’s helped U to heal ur heart and bring U happiness, if U see how it leads to kindness in the world—U will probably want to do more of that practice, to bring it into the world, to help others to do it. What we’re doing in the Love Department will immediately make a kind of sense. The same goes for the Curiosity or Empowerment departments—resonant people will just get it, and want to be involved.

I’ve planted my feet in the ground for Love, Curiosity, and Empowerment. I’ve literally tattooed them on my body!

When it becomes clear what ur vector is, plant ur feet in the ground. Commit to going in that direction, and articulate it in a way that others can understand. Write a manifesto about how U are going to be the best hip-hop-listening sparkly-hula-hoop dancers this side of the Atlantic.

This approach can rightly be seen as “top-down”—starting with a direction and a theme, and then gathering collaborators and designing projects around that theme. It works for me, but might not appeal to U.

A more “bottom-up” alternative would be to co-discover and co-create where U are going with ur collaborators, based on who U enjoy collaborating with, and what U all enjoy working on. In practice, U will probably discover some mix of these approaches that works for U.

Logistics: How We Actually Work Together

We are a global, international, online working cooperative. Members of The Service Guild currently live in the US, Canada, and the UK. And we have friends and allies all around the world. Whenever possible, I try to meet with Service Guild members in person—and we are gradually having more and more opportunities to gather collectively. Still, I would guess we will probably always be an online-first, distributed organization / crew.

A number of meetings happen in parallel, including team meetings and a number of one-on-one meetings, for a variety of purposes and structures. For example, I’ve been meeting with Abi every two weeks for three years now, to discuss our respective Curiosity inputs, outputs, and intentions for the coming two weeks. Or I meet with Bee Eye every six weeks to check in about the Mettā Dance Parties.

Each crew or team has to find its natural rhythm for meeting. We have an Empowerment Team meeting every six weeks, and I meet with Mary every four weeks for an Empowerment 1-1. Across The Service Guild, we meet on an as-needed basis on top of any standing meetings. And standing meetings are always up for discussion—do we still need to meet at this rhythm? Should we change the structure of our meeting to better suit our needs and goals?

One thing I’ve noticed is that we need to meet at a slower rhythm than what might be typical in a normal working environment. For example, I understand it’s a best practice in the corporate environment for a manager to have a 1-1 with a direct report weekly. Because we work less intensely with each other, for fewer hours per week, a 1-1 can happen every two, four, six, or even eight weeks in our crew. We’re playing long games, at a slower, more sustainable pace.

We use Zoom for online video calls and meetings. We use Notion and Google Drive for project management. We use Zulip for asynchronous messaging, and messaging platforms like Signal, WhatsApp, and Telegram for group chats and time-sensitive texts. We rarely use email, mostly to interface with outside collaborators and allies.

Since the beginning, we’ve started our meetings with emotional check-ins. As of this year, we’re starting our meetings and calls by saying the Guild Oath, and then doing check-ins. We also always record our meetings (starting after check-ins).

An important choice of structure is about hierarchy and-or non-hierarchical, distributed leadership. It’s not popular these days, but I am actually a big fan of hierarchy and we have woven hierarchy into The Service Guild.

That said, I am also a fan of commander’s intent (see my Strategy 101 article) and what we might call reciprocal leadership. For example, I might be in charge of The Service Guild overall, but “work for” or report to a specific collaborator in a specific capacity, for a specific project. Like, with heart kiss, I am Guildmaster and head of The Love Department, but Aspen is more in charge of heart kiss as such. She’s responsible for the quality and excellence of our music, as well as of my musical education and development. So in these respects, I “report to” her, even if heart kiss itself is part of The Love Department and therefore The Service Guild overall.

When push comes to shove, I am the Guildmaster. I hold the vision and values for The Service Guild overall, as well as its three departments. That said, I believe deeply in the axiom that “all problems are soluble,” that it’s possible to do so in ways that are win-win for everyone involved. We do this by listening deeply to the values people are holding, questioning implicit assumptions, and creatively seeking out solutions that work for everyone, that meet everyone’s needs. It’s not easy to do this—it takes faith, patience, curiosity, and creativity—but the solutions we find are, without fail, more powerful and impactful than the default solution that we would have reached for if we hadn’t done so, if we hadn’t taken the time to listen and find something that works for everyone.

In particular, the “Evaporating Cloud” or conflict resolution diagram from The Logical Thinking Processes have helped me and our team again and again, to find creative solutions that transcend apparently insoluble obstacles. The Evaporating Cloud disambiguates immediate proposals that are in logical conflict (“Sell the thing” vs. “Don’t sell the thing”) from the underlying needs or desires (Freedom and Autonomy vs. Ethical Responsibility), and helps U procedurally ask questions that root out inaccurate assumptions: “Could we sell the thing while maintaining ethical responsibility?” “Could we not sell the thing while cultivating freedom and autonomy?” When those assumptions are surfaced, creative, win-win solutions fall out automatically as a consequence.

It helps that there are rarely urgent decisions that need to be made immediately. Many decisions can be taken slowly, so that we can have time to reflect, sleep on our conversations, and come back with new perspectives and directions.

It also helps that we have deep friendships and relationships with one another that are built over time. We care about each other and each other’s perspectives. This makes it easier to have faith in each other, to believe we are all doing what seems best to us, to find ways forward that work for everyone.

I think this kind of win-win creative decision-making and problem-solving would be harder to do at a larger scale, with hundreds or thousands of people involved. At the scale of a small crew, it’s consistently possible, if not relatively easy.

Red Flags and What to Watch For

Here are some behaviors or indicators that have turned out to be yellow or red flags:

  • being late: it may or may not surprise U, but I’ve found that people who are late to scheduled calls or meetings, who cancel on short notice, etc. are unreliable collaborators; that’s fine for some personal or friend situations, but not ideal for people U want to collaborate with in an ongoing way. Of course, if someone has an unexpected emergency, that’s out of their hands—but even then, a responsible person will communicate promptly and effectively about such an occurrence. It’s less about things never changing or coming up, and more about how U handle unexpected change.
  • not DWYSYWD: saying they’ll do something, by a certain time, and not following through. Not following up as circumstances change. Not taking responsibility for actions.
  • wanting too much too soon: when people move too fast, do too big collaborations or make large, irreversible choices too quickly, that’s a recipe for confusion and hurt. In all honesty that’s usually been me in the past!
  • values mismatch: U have personal values, that U bring to ur work and choices in ur life. If those values mismatch in a fundamental way, or U have different priorities in the current chapters of ur life, it may make collaboration difficult or impossible. This shows up in choices about which projects to work on, who to collaborate with, how to relate to money, etc.
  • words/actions mismatch: one tricky pattern that took me a while to notice is that sometimes people’s explicit words are in direct conflict with their actions, their revealed preferences. For example, someone can be enthusiastic verbally about a potential collaboration, but have trouble following through on its first steps. To my mind, this is typically a sign of internal conflict—something we all go through, but it’s best to choose projects and collaborations where all parties can be a “hell yeah!” to it.
  • it just not feeling fun or good!: U don’t necessarily need a reason that U can articulate or discern to say “hey, yeah, no, collaboration doesn’t feel like the move any more.” In that case, simplify the relationship! Focus on friendship!

Sometimes, these are resolvable problems. A simple, direct, honest conversation can produce changes and adjustments that make it better for everyone. I’m also a fan of the Art of REPAIR for two-person conflict resolution, or asking a trusted third party to mediate when particularly sticky challenges or blind spots come up.

In general, a motto I have is “friendship first.” From one perspective, in The Service Guild, we are explicitly exploring dual relationships: being friends and collaborators. If the collaboration consistently feels sticky, unfun, painful in a way that can’t be resolved, then I will want to return to just being friends.

To me, there’s no project or situation that is more important than the preciousness of a friendship, no goal that is more important than a person and the relationship we have with them. Friendship first!

Crew Health

One of my edges as a leader, which is especially acute at the present stage of The Service Guild, is to consider the health of the group—both individually and collectively.

Individually: How is everyone doing? Are they flourishing in their lives? Do they have the resources they need to live their vow fully—financially, culturally, psychologically, emotionally? What are their biggest challenges, obstacles, goals? Is there any way I can support them in flourishing, that being connected to The Guild can be of more benefit to them? Can we unblock them with their biggest challenges in any tangible, specific way?

Collectively: How is each Department doing? What is going well in that crew? What obstacles or bottlenecks is each Department facing? What obstacles or bottlenecks is The Guild facing overall? What interventions would support The Guild and its departments in thriving? How can I create the conditions for The Guild’s long-term success and benefit?

Conclusion

Maybe the prospect of having a crew seems appealing. In that case—go for it! I challenge U to build a crew, to gather the team, to go and build projects that U are proud of. Start small, and get bigger and better with each and every passing year. Dream ur most inspiring, beautiful, ambitious dreams, and bring them about. Make them so, for ur joy and the world’s benefit.

Maybe it seems daunting! In that case, consider that it just takes one step. Whatever U know now, whatever is clear to U now, act on that. Just do the next thing. Ask a friend to talk about possible collaborations, for example.

Take this one next step, and then the next. One step at a time. One day at a time. What is difficult now, what feels daunting and seems impossible now may not always be so. Change happens, we grow over time, and new opportunities we cannot even imagine will certainly arise.

Alternatively, maybe U already have a crew. In that case, I hope that this article has given U some new ideas about how to approach ur crew, and how to take it to the next level. I’d be curious to correspond about what’s worked for U, and what hasn’t, what present challenges U are facing and where U are steering towards. And perhaps there’s a way we can collaborate together at the crew/organization level! Please feel free to be in touch.

I think this is a historic moment for the network: a key phase of developing systemic self-awareness, of new opportunities arising, of new possibilities opening up. That’s exciting to me—a grand adventure.

On the one hand, I want to see people who are working independently, to start to pair and crew up, to find or create dyads and groups and crews and organizations that hold them in their aspirations, that unblock them from their obstacles and challenges, that help them to rise up to greater things than they are capable of doing alone, by themselves.

On the other hand, I want to see more alignment between people who are already in crews, already embedded in supportive contexts—for the network to become self-aware at a higher level, to unblock itself, to connect the dots that yearn to be connected, in the physical realm across.

I would like to see more crews develop, and more collaboration, competition, coordination, discourse, trade, and exchange between these crews.

I would like to see the coming stage of flourishing arise—whether U call it a Golden Age or a Heavenly Realm, a new stage of possibility for our communities, species, and the world.

I want to be part of it; I want to weave all my friends and allies into it. I want to speed swiftly (without rushing) towards what I feel with all my heart is possible, what is right around the corner, what is almost already here.

We flourish together. May all beings benefit from our flourishing.

Further Resources:

Thank U to Anansi, Priya, and Svetlana for reading drafts of this post and providing feedback.