Collaborate Better Handbook

Raising Your Collaborative Intelligence

Now is the time

by Eli Woolery


During the past seven seasons of the Design Better Podcast, Aarron Walter and I —along with the rest of the world—have witnessed global crises ranging from a pandemic to war in eastern Europe. We’ve worked through our own challenges during this period, and have helped friends and family in times of need. Aarron took direct action to help out globally, leaving his full-time role at InVision toward the end of 2020 to work at Resolve to Save Lives.  

We’ve also seen the way people work evolve quickly over the past few years, most obviously in the shift for many to remote or hybrid work. During this period, Aarron and I have had the good fortune to speak to some of the brightest creative minds to help us and our audience understand how to navigate these challenging times. 

As work shifts from in-person interaction to more distributed and hybrid collaboration, it becomes increasingly important to understand how to collaborate effectively. This book will help you raise the collaborative intelligence of your teams, drawing from interviews with some of the most creative, prolific, and multidisciplinary leaders, authors, and makers in the world.

Aarron and I started this podcast to educate and inspire people in the world of product design, but over the years, as we’ve interviewed leaders and pioneers in disciplines ranging from astrophysics to comedy to fashion, we’ve realized that the collaborative toolkit that designers use can help every team. Correspondingly, we’ve discovered that design and product teams can learn from all kinds of disciplines.

In each chapter of this book, we’ll share relevant excerpts from our interviews as we explore the foundations we believe are critical to making your team—and you— more collaborative.

We’ll begin with collaborative leadership in Chapter 2, where Aarron discusses how effective leaders bring teams together to establish shared values and vision that help people take their own path toward success. He shares lessons learned from leaders like Julie Zhuo and Jason Mayden.

In Chapter 3, Aarron investigates what it takes to understand your colleagues. He looks at how Design Better Podcast guests like Benjamin Earl Evans, Jehad Affoneh, and Sara Seager have honed their skills at reading people, and the specific techniques they’ve developed that unlocked their collaborative potential.

Next, in Chapter 4, guests like Christian Madsbjerg, Brian Chesky, and Laura Martini help Aarron build a case for why understanding your customers will help assure that you’re running the race to success in the right direction.

In Chapter 5, I dive deeper into how mission, vision, and purpose can each be used as levers to raise your collaborative intelligence. Guests like Eileen Fisher and Chris Kemp offer examples of their own mission and vision, and Dan Pink speaks about the importance of purpose in work.

John Cleese, Irene Au, and David Kelley teach us about creativity, innovation, and divergent thinking in Chapter 6. They help us understand why creativity isn’t a solo act, and how to get in the proper mindset to access the right tools for creative collaboration. 

Finally, in Chapter 7, I share insights from Seth Godin, Katrina Alcorn, Sandy Fershee, and Marty Cagan about why building together—from low-fidelity prototypes to high-fidelity user tests—helps the whole team learn what matters most to users and customers, and ship the right experience to them with less wasted effort, in less time.

If you’re new to the Design Better Podcast, we hope this book will encourage you to listen to some of our favorite episodes. And if you’re a longtime fan, we hope that you’ll share this book with your colleagues to get them excited about the opportunity to learn from some of the brightest creative minds out there. 

Of course, this book wouldn’t be possible without the generosity of the people who have shared their stories with us and with you. We have enormous gratitude for each of our guests, and we hope that by sharing their wisdom, we can inspire you to build great things together with your team. 

Collaborate Better Handbook

Creativity, Innovation, and Divergent Thinking

Creativity isn't a solo act

by Eli Woolery


When actor and comedian John Cleese was collaborating with fellow Monty Python writer Graham Chapman, he once lost a script and knew that Chapman would be frustrated with him. So he sat down and rewrote it from memory, and when he later discovered the original script, he found the rewritten one to be much better: “I hadn’t been trying to make it better. … I was just trying to remember it. So my mind must have been working on it.”

The idea that the unconscious mind continues to work on creative problems even after we’ve set them aside has been well documented, from the story of Russian chemist Dmitry Mendeleev falling asleep at his desk and awaking with the configuration of the periodic table of the elements, to August Kekulé’s dream of a snake biting its tail leading him to discover the benzene ring. 

If you’re an accountant, you know pretty much how much you can do in a day. Whereas Claude Monet … at the age of eighty, when he went out to paint, his hand used to shake from nerves because he wasn’t sure if he could do it this day. And creative people can never be sure that it’s going to happen today because you can’t order your unconscious around. You have to just wait and coax it and be nice to it. —John Cleese

But what if, when working with a team to come up with creative solutions or innovative new products, you can’t rely on group naps to come up with ideas? It turns out there are several frameworks you can use, either as a team or as an individual, that will help you collaborate more creatively. 

In this chapter, we’ll discuss divergent versus convergent ways of thinking (or, to use John Cleese’s wording, “closed” versus “open” modes) and how they enhance creativity. We’ll learn from Irene Au about why creative ideas can come from anyone, and IDEO and Stanford founder David Kelley will teach us how to improve our creative confidence. Benjamin Evans and Jake Knapp will tell us about the importance of inclusive creativity to innovation, and Seth Godin will talk about why he views being creative as an act of generosity.

Convergent and divergent thinking

In his book Creativity: A Short and Cheerful Guide, John Cleese refers to two styles of thinking first proposed by Guy Claxton in Hare Brain, Tortoise Mind. “Hare brain,” writes Cleese, citing Claxton, is the kind of “quick, purposeful thinking” that “involves ‘figuring matters out, weighing the pros and cons, constructing arguments and solving problems.’”

This is the type of analytical thinking you might use when trying to narrow down choices for your family dentist, or when helping your daughter solve an algebra problem for her homework. At Stanford’s, we call this “convergent thinking,” and it is the dominant form of thinking most organizations use to tackle problems. It works especially well when problems are concrete, constrained, and well defined.

But what if you’re facing a creative problem that is more nebulous, delicate, or ambiguous—one where there may be no obvious “right” answer? In that case, you may need to turn to other ways of thinking, which Claxton collectively calls “tortoise mind.” These “more patient, less deliberate modes of mind,” Claxton writes, “are particularly suited to making sense of situations that are intricate, shadowy, or ill-defined … when we are not sure what needs to be taken into account, or even which questions to pose.”

Cleese goes on to discuss the importance of allowing space and time for the tortoise mind to work, and gives examples of a study done on architects to determine why some were more creative than others. The findings from the study pointed to two key differences between creative architects and their less successful counterparts: the more creative architects “knew how to play,” and they also “deferred making decisions for as long as they were allowed.”

There’s a very clever Chicago psychologist called Mihaly Csikszentmihalyi, Hungarian— you know him, you’re nodding. He wrote Flow. He did an experiment with the Chicago Institute of Art. And they just got a lot of people, and gave them a desk each, and there was a table with lots of objects on it. And they had to choose objects and draw a still life. 

And you could see that the students just fell into two categories. There were people who went straight up and very quickly would choose the pieces and come back and do the arrangement and then start drawing it. And from very early on, you could see what the composition was going to be. 

And there were other people who behaved quite differently. They’d go up and instead of just choosing the objects, they’d pick them up and they’d almost toss them in the air or smell them, or sort of feel them. And then they’d pick up another one. They’d take much longer to choose the original objects that they wanted. And then they’d bring them back to their desk. 

And again, they would take much longer to get the configuration right. In fact, they might take a couple of them back to the table and replace them with something else. And then after that, they would take longer to get going on the composition and they’d change it more often. And finally, they’d come up with something. 

And when they showed the two lots of work, because they did—you know, they could sort of divide them into these two ways of approaching—they discovered the professional artists said all the good ones are the people who taken a long time to feel it out, instead of the people who’ve done it with the front of the mind.

And later on a follow-up study showed that the ones who’d done well in that test were the ones who were making a living, a nice living out in the world, doing creative things that the other ones weren’t. —John Cleese

In the “move fast and break things” mindset of many organizations, there is often no latitude given to employees to address problems using this second way of thinking. Play is seen as wasted time, and deferring decisions only increases the anxiety of managers who have been asked to come up with a solution as quickly as possible.

But applying “hare brain” to the wrong types of problems is counterproductive. Like pushing on a string, you’ll waste time and, perhaps more importantly, weaken morale if you try to force an analytical solution on a problem that requires creativity. Instead, you need to get your team members in the right frame of mind and provide them with tools for coming up with divergent solutions, which you can later use your hare brain to narrow down.

Crummy brainstorming

You’ve probably been in a brainstorming session that went something like this: 



Manager: Hey team, we need to come up with a fix for this onboarding experience! Way too many people are dropping off after the third step. Let’s huddle up and brainstorm.

Four employees and the manager shuffle into an empty conference room. Two of them have stopped an analytical task they’ve been working on, while the remaining two are irked at having to interrupt a watercooler discussion they were having about cats.



Employee 1: Do I really need to be here? I was trying to finish up a quote for one of our distributors.



Employee 2: Yeah, and we were having an important meeting about … the business.



Employee 3: I was actually working on more important things than any of you were, but let’s do what he’s asking. I’ve got my whiteboard marker ready, let’s go.



Employee 4: Sighs and slumps down in his chair.


They start “brainstorming,” which is really nothing more than the Manager and Employee 3 having a loud back-and-forth argument about whether the third step should be multiple choice or have radio buttons, while the other employees—who do have contributions to make—either work on something else on their laptops or sit there disengaged.

But by the end of the session, which has gone on for over an hour, Employee 3 and the Manager think they’ve come up with something brilliant. They high-five each other. Indecipherable scribbles cover the whiteboard. Employee 1 has already left to do something more productive.



Manager: OK, great job team, I think we’ve come up with the right solution here. I need to scoot so I can get to the gym during lunch and work on my core.



Employee 2: Yeah, your solution looks, umm … great? Can we, like, leave now?



Employee 3: No, why don’t you both stay here and work through the details during lunch? I need our manager to spot me while I’m bench-pressing a ridiculous amount of weight at the gym.


Employee 4: Sighs and slumps farther down in his chair.

Clearly, this type of brainstorming is unproductive. No clear goals have been set, no one is in the right headspace for the task, and two out of the five people are totally dominating the conversation. There’s a far better way to come up with creative solutions collaboratively. Read on.

Better brainstorming

For a better way to brainstorm, you’ll need to do three things: set a goal, get into the right headspace, and get everyone to participate. We’ll walk you through it here, and you can also use the templates below to help guide you through the process.

Choose a facilitator and set a mission

A key part of the brainstorming process is the facilitator—someone who will lead the session, keep track of time, and set up the space for the group (whether virtually or in person). 

Unlike the haphazard scenario we discussed earlier, your brainstorming session should have a clear goal. What problem(s) are you surfacing ideas for? What is the best method for coming up with this goal? The facilitator can also make sure the group comes prepared with a mission framed by problem statements.

In Chapter 4, we discussed mission statements and POV statements, which are like bite-size mission statements. A mission statement is vital for your company, but you can also create POV statements for new products, features, or experiences. Using your POV problem statement, come up with “How might we … ?” topics that are subsets of the entire problem. If your POV statement is well constructed, these topics should fall naturally out of it.

For example, let’s go back to Doug Dietz’s POV:

We met scared families trying not to fall apart during the hospital visit. We were amazed to realize that they have to sedate 80% of the children between 3 and 8 years old, in order to have them be scanned. It would change the world if we could capitalize on the child’s amazing imagination to transform the radiology experience into a positive, memorable adventure.

With that POV, you can pretty easily come up with problem statements like “How might we make the MRI scanner a more imaginative space?” or “How can we reduce anxiety before appointments by sparking children’s imaginations?” With these topics, you can then set up brainstorming sessions to surface a lot of ideas.

Get into a better headspace

If you’re coming into a brainstorming session from individual work, it can be a little jarring to adopt a collaborative mindset—and difficult to ramp up your energy level accordingly. It’s really hard to switch instantaneously from hare brain to tortoise mind, so the facilitator should spend a few minutes getting everyone acclimated. You can use an exercise like 30 Circles (we have a version in Freehand), or an icebreaker, to get people warmed up (Fig 6.1).

It’s also important to consider the right time of day to hold a brainstorming session. As Dan Pink notes in his book When, some tasks are better done at certain times of day. Because brainstorming requires us to defer judgment, consider scheduling a brainstorming session late in the day or early in the evening, when people tend to be less vigilant.

Get everyone to sketch ideas

In a traditional brainstorming session, often it’s only the loudest voices who contribute, which doesn’t leave room for introverts who might also have great ideas. Instead of shouting out ideas and writing them down on a whiteboard, getting everyone to do some time-boxed sketching makes sure that no one gets left out of the process.

There’s another reason sketching is important. In his book Originals, Adam Grant tells the story of how the hit comedy Seinfeld—a show famously about “nothing”—was previewed for an audience of executives, and never would have made it to the TV screen except for one person who was able to defer judgment and accept it for its originality. 

Taking a cue from Grant’s research, we can prime people to be in a divergent, nonjudgmental “tortoise” mindset by getting them to sketch new ideas: “Just spending six minutes developing original ideas made [people] more open to novelty, improving their ability to see the potential in something unusual,” Grant writes. And: “If we want to increase our chances of betting on the best original ideas, we have to generate our own ideas immediately before we screen other’s suggestions.”

The Crazy Eights exercise is a simple, easy way to get people sketching ideas together. All you need is some letter-sized paper and pens, or a Freehand template (Fig 6.2).

Here’s how it works:

  1. Get your team and other relevant stakeholders together—but limit the group to eight or fewer to keep the discussion productive.
  2. Give each person a sheet of A5 or 8.5″ x 11″ paper. The paper will be folded three times to create eight boxes (for eight sketches). The Freehand template is set up for four people, but copy-paste the frames if you need more spots.
  3. Frame the problem for everyone, using the POV statement you drafted earlier, or a How might we statement. “We want to help customers become active in this app more quickly. How might we achieve that?”
  4. Set a timer for eight minutes and instruct everyone to sketch solutions individually (and silently, to help everyone focus). Freehand has a built-in timer to help with this.
  5. When the timer goes off, it’s time for team members to present their ideas. Conversation about each idea is important here. Critical feedback will help you see which ideas are best. Every team member should be given the opportunity to share sketches.
  6. If you’re planning to move on to prototyping your ideas (more on that in Chapter 7), you can get participants to use sticky dots (or emoji) to vote on the idea(s) to move forward with. Sometimes it’s helpful to offer a few categories to vote on (e.g., “lowest hanging fruit,” “most delightful,” “moon shot,” and so on).

Building creative confidence

Along with his brother Tom, my mentor David Kelley wrote a book called Creative Confidence. The basic thesis of the book is that we’re all creative as children—can you think of a toddler who doesn’t like to fingerpaint, sing, or make things out of clay? 

But then much of this creativity is drilled out of many of us as we go through years of schooling, where emphasis is typically placed on memorization and standardized testing. These are taught at the expense of practicing creative endeavors, which are seen as “nice to have,” but not critical.

When we graduate into adulthood or even early adolescence, we may opt out of thinking of ourselves as creative because we worry about being judged, or because we compare ourselves to peers who have continued to practice creative skills.

What’s happened for us is that somewhere along the line, kids opt out of thinking of themselves as creative, and I talk about this all the time. Your question is how do you get them back … to that confidence … Once people have creative confidence, they have more sticktoitiveness, they take more risks, they do all the things.  —David Kelley

To get past these hurdles, we need to transform “fears into familiarity,” to borrow David’s words. This is the idea of guided mastery that psychologist Albert Bandura pioneered. By carrying out a series of small successes, we begin to develop the confidence in our creativity that we likely lost as children.

What are the best ways to start building this confidence? Sketching exercises like Crazy Eights are a good place to start. At your next creative meeting, you can also try a visual warm-up like Drawing Toast (Fig 6.3).

Inclusive creativity

Once your teams begin building their creative confidence, another ingredient is necessary for effective creative collaboration. You need input from an inclusive set of contributors: people who don’t all think and act alike, but who come from a variety of backgrounds and experiences that can contribute to real innovation. 

In Chapter 3, Aarron brought up something Benjamin Evans, director of product inclusion at Paypal, said: “If innovation is about taking two ideas that are different and overlaying them and mixing them, then that means that the more you do that, the more opportunities there are for innovation and the more creativity there is.” 

Having a diverse team can contribute to coming up with more and better ideas, but, as Benjamin suggested in his conversation with Aarron and me, it can also contribute to friction. For this reason, as we explained in Chapter 2, it’s important to have strong leaders who understand how best to support and leverage these teams.

Being inclusive also means bringing lots of different roles into the creative process as early as possible. Tools like design sprints can be an effective way not only to marshal the team working directly on the product, but also to include other stakeholders like executives, HR, and legal in the very earliest stages of exploration. They’ll be much more likely to buy into the decisions that are made down the road if they’ve been part of the process from the start.

As Jake Knapp, coauthor of Sprint, says, the story of the product is really the most important thing in getting it out to the world, not only to the end consumer, but also to the internal teams that need to come together to ship it:

And in fact, it’s actually the most important thing, because if you can’t explain what your new product or service is, if it doesn’t make sense to people, you’re just adding a feature to an existing product. If it doesn’t make sense to people—why they would use it—if there’s no story around it, then there’s really no point. 

And so many, many products fail or succeed based on how well they tell that story. So I also really wanted teams to start thinking of that story, and how they were going to explain what they did almost more than they thought about the intricacies of the interaction design itself, because it matters more. —Jake Knapp

Creativity as an act of generosity

For some people, acts of creativity may seem to have a selfish element to them: “Look at me, look at what I’ve done.” But it’s easy to reframe that. What if your act of creativity were anonymous? Would it still feel good to have made the contribution?

As Seth Godin told us:

Well, here’s the simplest hack. What if it was anonymous? Right? What would happen if there was no chance you could get credit or blame, would you do it? And if you did it, what would it feel like? 

And so it can be something as simple as: brunch is going on in the restaurant and the door keeps slamming shut, and somebody gets up and without any fanfare just puts a little piece of wood in there to keep the door open, right? That is a creative act on behalf of others, for which you cannot be compensated. 

And if you interrupted everyone in the restaurant and said, “I’m doing this, thank you very much. Please applaud,” now that would be different. 

And if we begin with that, then we realize that the best design interventions don’t have to have our names signed to them. If you get in that habit, then it becomes a generous act to actually sign your name so that the next person knows where to find you. So you can do a generous act for them because the more leverage we have as generous actors, the more generosity we’ll be able to share with other people. —Seth Godin

For most of us, contributing to a creative team effort has intrinsic value, even if our names aren’t attached to the final result. Revisiting Dan Pink’s mastery, autonomy, and purpose from Chapter 5, we can say that these acts give us a sense of purpose in our daily roles.

In the next chapter, we’ll teach you how to harness your team’s creativity to build things together in an iterative fashion, learning along the way how to make better products.


About the Authors

Eli Woolery
Senior Director of Design Education / InVision

Eli Woolery is the Senior Director of Design Education at InVision, and co-host of the Design Better Podcast. His design career spans both physical and digital products, and he has worked with companies ranging from startups (his own and others) to Fortune 500 companies.

In addition to his background in product and industrial design, he has been a professional photographer and filmmaker. He teaches the senior capstone class Implementation to undergraduate Product Designers at Stanford University. You can find Eli on Twitter and Medium.

Aarron Walter
Author and co-host of the Design Better Podcast

Aarron Walter is the co-host of the Design Better Podcast, and author of Designing for Emotion. He was the Director of Product on the COVID Response team at Resolve to Save Lives, and prior to that, the VP of Design Education at InVision. He founded the UX practice at Mailchimp where he helped grow the product from a few thousand users to more than 10 million. He’s the author of a number of books, the latest of which is a second edition of Designing for Emotion. Aarron’s design guidance has helped the White House, the US Department of State, and dozens of major corporations, startups, and venture capital firms.

You can find Aarron on Twitter and LinkedIn.