Notes on Collaboration

Curated bits of wisdom on how to work with other people

Collaboration is hard.

I wish someone had told me that it is supposed to be hard.

In school and college, the assumption often seemed to be that just the act of putting people on a team would somehow induce teamwork. No one taught the members how to actually collaborate.

Go collaborate!

If you didn’t get along, you just divided the work so that you could avoid each other. More, it was short-lived — on the next project you could team up with someone new.

It was when I started my first company and the stakes became real, that I learnt how hard it was to work with other people.

There was no next project. I was stuck with my co-founders, and they were stuck with me. It wasn’t about getting a good grade, it was about our lives.

We ran that company together a little shy of five years. Keeping our co-founder relationship functional had been one of the hardest bits.

Here’s the mistake I did next. I fooled myself into believing that I now knew how teams work. I came up with rules of thumb like how many members a team should have, should you or should you not work with friends, etc.

How wrong I was and continue to be. Every new team has been a fresh set of learnings and no single variable has been a good predictor of which team will work well. One of the best teams I’ve ever worked on had 9 core team members. (Sidenote: We did some pretty rad stuff! Look at Stanford 2025 if you want to learn more).

So what to do? I realized that teamwork isn’t something you achieve by design, it is something you evolve once you are part of the team. And since you have little control over how your teammates will function, the only person you can work on is yourself.

Sarah,’s Executive Director once used the phrase “practice your collaborative muscle” when talking about teamwork. It’s a great metaphor. Collaboration is a muscle, and practice makes you better.

To that end, how does one prepare oneself? In this post, I’ve curated some of the advice and tools on collaboration that I’ve picked up over the years.

On Teams in General

What you should expect

  • In the play No Exit, Jean-Paul Sartre creates a curious depiction of hell: Three people locked in a room together for eternity. That’s basically your everyday project team. Apparently, that’s the origin of the quote “Hell is other people”.
  • On my first job out of undergrad, my boss taught me about the phases a team goes through: Forming, Storming, Norming, Performing. It’s called the stages of group development proposed by Bruce Tuckman in 1965. My expectation until then had always been to be in Stage 4. Performing from the moment the team is formed. Knowing this framework made me patient and accepting of conflict.
Stages of group development
  • Red Burns, the founder of NYU’s Interactive Telecommunications Program would kick-off her class a series of slides to set the tone for their time at the ITP. There are many bits of wisdom there, and here’s one on collaboration:
Red Burns’ slide
I loved this metaphor. It’s a powerful way to set your own expectations on working with other people. Collaboration is an acquired taste. (Sketched by me)

On Giving and Receiving Feedback

The necessary evil (or gift) of teamwork

  • Douglas Stone, Shiela Heen and Bruce Patton from the Harvard Negotiation Project have written two excellent books on working with other people — Difficult Conversations and Thanks for the Feedback. The latter is something I found incredibly helpful as it changes the frame from the feedback giver to the feedback receiver. Here’s an excerpt:
As we worked to develop ways to approach feedback differently, we soon realized that the key player is not the giver but the receiver. Because feedback givers are abundant, and our shortcomings seemingly boundless, feedback can trigger us in a googolplex of ways. There are three.
Truth Triggers are set off by the substance of the feedback itself — it’s somehow off, unhelpful, or simply untrue. In response, we feel indignant, wronged and exasperated.
Relationship Triggers are tripped by the particular person who is giving us this feedback. We can have reactions based on what we believe about the giver (they’ve got no credibility on this topic!) or how we feel treated by the giver (after all I’ve done for you, I get this kind of petty criticism?).
Identify Triggers focus neither on the feedback nor on the person offering it. Identity triggers are all about us. We are suddenly unsure what to think about ourselves, and question what we stand for.
Our triggered reactions are obstacles because they keep us from engaging skillfully in the conversation. Receiving feedback well is a process of sorting and filtering. Shelving or discarding the parts of the feedback that in the end feel off or not what you need right now.
  • The book Discussing Design shines a light on critique; a type of feedback that is unique to design. They book features some delightful critique monsters which coach you through different ways of sharing critique.
  • Kim Scott has written a book titled Radical Candor on the topic of feedback. I like her earlier iteration below. The horizontal axis you have unclear to clear feedback, and on the vertical you have the spectrum of anticipated emotions from happy to unhappy. The gentler the feedback, the less clear it tends to be. That’s the cruel empathy quadrant. The one you want to be in is the top right — clear even if it’s bad news. The “anticipated emotions” was helpful for me to learn because I’d often change my feedback based on that.
  • I’m sure you have come across the shit sandwich, the staple framework on how to give feedback. “The shit sandwich is a technique for giving feedback that involves sandwiching critical, truthful feedback (the shit) in between two slices of praise” I have done my fair share of giving out shit sandwiches. A better alternative is’s I Like, I Wish, What If framework created by Julian Gorodsky.
The shit sandwich

On Ways of Working Together

How you might show up for your team

  • The standard model of group work is “Discuss and Distribute”. You get in a meeting to discuss the project and then distribute the pieces of the work. Carissa Carter, the Director of Teaching and Learning at the designed the exercise below to get students to practice different styles of collaboration. When I came across this exercise, I had been struggling a bit on how to work with some of my teammates. I had tried to “parallel process” a project with someone, and they were just offended at why I would take over their work. In another scenario, I was frustrated because I wanted to be the “lead” and not just provide “color”.
“Make Muffins” — an in-class activity to practice collaboration designed by Carissa Carter. To get the exercise in a cool “zine format” go here.
  • Edward de Bono’s Six Thinking Hats framework introduces the idea that everyone in the group choose a particular direction (denoted by the color of the hat) in which they direct their thinking. So instead of Sally always talking about how this might not work, and Sue always wanting more information before making a decision, they pick one direction as indicated by the hat color. For example, “Let’s have some white hat thinking here” means a deliberate focus on information. Everyone now tries to think of that is available, information that is needed, questions to be asked, other ways of getting information, and so on. De Bono heavily reiterates that the hats are not categories of people. Yes, someone may have a strong default, but everyone can put on all the hats. Edward de Bono also traces the history of why we work they way we do:
The basic idea behind Western thinking was designed about 2300 years ago by the Greek “Gang of Three” and is based on argument. Socrates put a high emphasis on dialectic and argument. In 80 percent of the dialogues in which he was involved, there is no constructive outcome at all. Socrates saw his role as simply pointing out what was “wrong”. He wanted to clarify the correct usage of concepts like justice and love by pointing out incorrect usage. Western thinking is concerned with “what is”, which is determined by analysis, judgment and argument. This is a fine and useful system. But there is another whole aspect of thinking that is concerned with “what can be”, which involves constructive thinking, creative thinking, and “designing a way forward”.
  • Imagine a discussion, where someone volunteers the ‘Let me be the devil’s advocate for a bit…’. Ugh. Perhaps I shouldn’t complain because I did that for years. In a similar vein to de Bono, Tom Kelley’s 10 Faces of Innovation introduces personas one can adopt besides playing the devil’s advocate. This is what Kelley says about ‘The Devil’s Advocate’:
Having invoked the awesome protective power of that seemingly innocuous phrase, the speaker now feels entirely free to take potshots at your idea, and does so with complete impunity. They are essentially saying “the devil made me do it.” They’re removing themselves from the equation and sidestepping individual responsibility for the verbal attack. But before they’re done they’ve torched your fledgling concept. — Tom Kelley
  • I learnt about the mode of “Yes, and…” through Improv. More than just a rule for improvised stage comedy, to be able to build on other people’s ideas is fundamental to groupwork. Patricia Ryan Madsen, who wrote the book Improv Wisdom has to say the following about the approach of saying “Yes…”
It is undoubtedly an exaggeration to suggest that we can say yes to everything that comes up, but we can all say yes to more than we normally do. Once you become aware that you can, you will see how often we use the technique of blocking in personal relationships simply out of habit. Turning this around can bring positive and unexpected results.
Saying yes (and following through with support) prevents you from committing a cardinal sin — blocking. Blocking comes in many forms; it is a way of trying to control the situation instead of accepting it. We block when we say no, when we have a better idea, when we change the subject, when we correct the speaker, when we fail to listen, or when we simply ignore the situation. We are not only experienced at blocking others, we commonly block ourselves.
  • In my personal experience, adding writing as a way to express oneself is often very effective. Not everyone in your group will be good at verbal combat. Making room for writing can help. Several exercises are aided through “worksheets”, in that you get time to first write what you think and then share what you wrote.

On Things Not About Work

Catalysts that are outside of “work”

I think people understand that people need to connect outside of work to become better teammates. That probably explains the host of team offsites that HR departments spend $$ on and yet they come off as formulaic. Here’s a couple of things I’ve noticed at the that don’t require an offsite.

  • Party, Park, Jail is a warm-up improv game to “quickly establish intimacy between a team”. Students get into small groups and answer three questions. The questions get deeper as the game progresses. From “What do you like doing on weekends?” to “How do you want to be seen by other people?”. I’ve played this a few times and one time it really changed how I viewed one of my team members.
  • Scott Doorley,’s Creative Director is a master of “reading the room”. Of course he is, the man wrote a book on designing environments for creative collaboration. I am still deconstructing his methods, but one thing I’ve always noticed he could do is to know when to bring food to a meeting. You would not even know when he’d be gone for a brief moment and would come back with some trek mix, or chocolate nibbles or even just beer! Subtle but powerful.

On How You Will Feel Along The Way

On dealing with emotions that you might experience

  • One expectation that you may have from your team is that give their 100% to a project. And you seek evidence of this in their work. Was it well done? Was it on time? Etcetra. And when you don’t see that evidence you might assume they are just not committed enough. What changed this for me was the following experience as a manager. I assigned some work to someone and in my head, it was a day’s work. Two days later it was still not done. My expectations had already been colored from working with him in the past, so obviously, not doing this meant he didn’t want to do it. He was fucking around. Until I saw how he was doing it. And realized he had chosen an infinitely slow method. Once we fixed that, he wrapped it up in a jiffy. I realized I had read a gap in skill as a gap in motivation. This sentiment is captured by Hanlon’s Razer:
Never attribute to malice that which is adequately explained by stupidity.
  • “I don’t like that man, I must get to know him better”. I’ve learnt the most about myself when working with people I have had the hardest time working with. The Abe Lincoln quote was a useful to discover when I was in the middle of some of these interactions.
  • Julie Zhou tempers the temptation to go it alone, in her essay Unintuitive Lessons on Being a Designer:
How nice it would be, I find myself thinking sometimes, to go it alone. To be my own creative master and do the things I think are right. But then, reality sets in. What can I expect do on my own? Make a webpage. Make a simple app. Make some cool conceptual demos. Start my own company. All of those options (except potentially the last one) would be fun, but they aren’t going to be impactful, which is something I have always personally valued. And if I did decide to start a company and by some lucky stars it somehow began to take off, I’d certainly end up having to work with others. There is no eating your cake and having it too when it comes to complete creative freedom while doing things of great magnitude and influence. Not even at the very top.