Pre-Pandemic hard conversating — our team doing the hard work

Collaboration, are we doing it wrong?

Jodi Cutler
7 min readJun 28, 2021

Collaboration is an awful proxy for respecting people who don’t think like you.

We hear it all the time.

“Collaboration is essential. This is a group project. You’ll need to be a key cross-functional collaborator.” Or maybe it’s “partner with two to three classmates to work on this paper.” Perhaps it’s, “I need the three of you to bring your expertise together for this client pitch next week…”

We’re constantly being asked to collaborate at school and work. Some people love it; others hate it. Some think it will ruin all that’s good about their idea. Others know that, without collaboration, giant gaps in thinking will be the only sure thing. All the while, there are few discussions about how to collaborate.

Somehow, we’re expected to know how to do it successfully. Little time is spent on how to be a good collaborator and how diversity can improve a single-threaded idea. This is something that needs to be discussed and improved.

3 steps to better collaboration

Self-awareness is the first step towards being a good collaborator. Know your strengths and weaknesses and communicate them to your fellow collaborators.

I used to believe I wasn’t a good writer. Growing up, I had a poor foundational education and never got the hang of writing. I’m an excellent talker, so eventually, the desire to share my ideas in written form overpowered my fear of failure concerning my lack of writing skills. To improve, I partnered with folks who are better at writing than I am. I have the idea; they write words, we refine and build, back and forth, until we’re done. I was aware of my limitations, communicated my shortcomings, and sought partnership to do what I couldn’t on my own.

Humility is the second step. As I learned that I didn’t have all the skills I needed, I heard myself making what I thought were apparent suggestions and heard in return, “Oh, I didn’t think of that.” Recognizing that I could bring my perspective and mix it with my awareness combined to create a mix of conviction of imperfect ideas.

In addition to flying solo, we can be creative together. Happy accidents are serendipitous interventions. They are the opportunities to consider a change in direction. Sometimes our ideas need grounding; at other times, they need lifting.

I have an expression to describe what good collaboration feels like: “rock to the balloon.” Sometimes, I’m the rock, and other times I’m the balloon. I’m a designer, and my ideas are meant to challenge our experiences with technology. Many of my ideas aren’t quite in the realm of technical possibility…yet. Willing engineers explore ideas with me. Sometimes, as the rock, they keep my balloon from flying away. At other times, the balloon lifts the rock. When I hear a collaborator say things like “what if…” or “maybe…lemme try something,” I know they’re in on the game.

The third step is curiosity (which is really a current that runs through everything). Curiosity is a skill like any other. It can be newly discovered, nurtured, or squashed. Start by asking why, just simply why. If you remember to ask why, indulge your curiosity and go on a journey of discovery. It seems super obvious to say, but we forget to do this critical follow-on step. You don’t have to find an answer; just make an effort to discover. The reward system for asking questions is permission to pursue an answer.

If these are new skills to you or you’re familiar with them but haven’t spent time developing them, my hypothesis is that collaborating isn’t fun for you.

Maybe you’ve embraced these ways of seeing the world, but collaboration is still tricky. I’ve found tactics that communicate the role we play in collaborating as individuals together.

Collaboration tactics

Inventory your skills

Not everyone is good at empathy, listening, or sharing. I think that’s ok. What tends to be challenging about this is that those who lack empathy may not know that it’s needed or valuable. In my experience, I’ve seen that ‘different’ tends to be valued less and not understood. I’ve finally learned that I don’t want everyone to be good at what I’m good at. Others have their own things they want to be good at, and there’s a place for that.

Let’s invoke one of our skills from earlier and get curious about what your co-collaborators love doing. Ask what they’re ok with and what they detest. Play to each other’s strengths. Verbalizing, externalizing, and revealing what we’re good at will set us up to hold ourselves accountable later.

The first time I was asked what my “superpower” was in a group setting, I was utterly embarrassed and unsure what value it would bring to the project. Thinking about superpowers was odd and uncomfortable for me.

I just do what I do. I’m a people watcher. I love listening to people and holding space for their stories. I’m that person that total strangers reveal their deepest darkest secrets on a 3-hour plane ride. I didn’t think there was anything terribly special about that.

The session facilitator helped me realize that my ability to listen is a foundation for building empathy and connections to people. I’ve come to understand that empathy is a superpower…just one that we can all share.

By identifying your skills, you expand on your self-awareness, learn about your team, and hopefully identify some gaps in what you all bring to one another. Tactically, you’ll collectively know what you’re working with.

Clear expectations and accountability

Let’s talk games. When you play a game, there are agreed-upon rules. If you are playing Monopoly at a new friend’s house and mid-game they throw up some house rules, it’s going to get ugly.

Collaboration is no different. If we don’t lay the rules out for all to know, it’ll get ugly. Since people come with their own experiences and backgrounds, it’s essential to say out loud what these expectations are. Articulating your shared rules is the foundation on which flexibility can be built. This includes establishing rules for engagement, when you will meet, how you will hold each other accountable, what accountability means, and how you will communicate.

When we don’t articulate our expectations, we run the risk of conflict and confrontation. When expectations are implicit, that’s when a team falls into contention. When we have no way to communicate a newly discovered expectation and consider its ramifications, that’s when shit goes sideways.

My daughter struggles with team projects. She ends up doing more work than intended. She gets frustrated because someone doesn’t do what she thought they ought to be doing. Over more than a few discussions about this, we discovered that she is overly accommodating. Being this way, she is obliquely communicating that she doesn’t need help. By filling in the uncomfortable silence, we make accommodations that devolve into anger, frustration, and misconceptions of mal-intent.

To counter a lack of expectation setting, I love establishing a delegation board (modern RACI). By getting a new team to articulate all of the known things that need to happen, you can identify where there may be redundancies or overlap in output.

I’ve run Mural sessions to pose the question, “What needs to happen for this project to be successful? List all the things that you need to do. List what you’re dependent on. What should happen”. This list is an opportunity to align on everything that needs to happen. Combine what the team is good at and what needs to happen, then you can then have folks sign up for tasks. Task assignment is the foundation for accountability. Take people at their word and assume they mean it. Full. Stop. If folks aren’t meeting an agreement, it’s up to you to let them know. Radical candor isn’t about being a jerk; it’s about establishing the rules. Be clear. Be considerate. Allow for people to be flexible but establish the ground rules to have the conversation.

None of these suggestions are silver bullets for having engaging and rewarding collaborations. They are what I’ve seen contribute to good collaboration. It’s still hard with all of these things because…change. Change is hard.

Vulnerability and exposure

Most US public education focuses on getting the correct answer rather than valuing the skill of asking the right questions. We are evaluated and judged on what we know. It’s not valuable to state what you don’t know. You didn’t study hard enough or pay enough attention to know the answer. When we say I don’t know,” it’s final.

To make not knowing less scary, I’ve introduced a liberating word to that statement, “I don’t know.” And it’s simple. I don’t know…yet. That simple addition changes everything by inviting someone who does know to share what they know. That your knowledge can be improved by a peer is completely counter to how we’ve been taught to learn.

When we say “I don’t know…yet,” willingness to change is demonstrated. If you are comfortable with collaboration, demonstrate that the waters are safe for others to change as well.

One of the first things I do is show how an idea can get better by invitation. This exposes fear and fear breeds anxiety. By revealing and sharing what we’re afraid of, we can address and dismantle it together.

For instance, when I facilitate first-time collaboration sessions, I like to demonstrate how flexible I can be. I include a deliberately ambiguous error in the day’s agenda. Someone will almost always point out the bait I’ve left for them. At that moment, I enthusiastically ask the group for feedback and enact their suggestions in real-time. A simple demonstration of my own flexibility is an invitation for others to increase their own.

While I invite flexibility, it doesn’t always work. Sometimes, it takes a few tries. But, I show how to be vulnerable and that the group can be friendly.

We all come with so many stories. We show up to a project as ourselves. I don’t expect anyone to share why they are or aren’t their best selves any given day. I do hope that I can articulate what I need or expect of people so that they are free to be themselves.

In my experience, wicked problems are appropriately complex. No one person can identify the correct issues to solve or the best approach to resolving them alone. To make our lives more equitable, we must invite others to broaden our perspectives with better intention and articulation.

I am here to accept being challenged and evolving my old ways of thinking, and I hope you will be too.

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Jodi Cutler

wifey. maker of things. whole food cooker. treehugger. LADA - Type1 diabetic. HEB Partner