Q & A

How Do You Create the Space for Creativity?

You know that creativity is essential to long-term success, but finding the time can seem impossible in the deluge of emails and meetings. Amy Whitaker ’01, author of Art Thinking, talked with Yale Insights about how can leaders maximize creativity in their teams while controlling risk.


Q: You have both an MBA and an MFA. Your book, Art Thinking, aims to share ideas that come from meshing those two worlds. Could you explain your definition of art and why a deeper look at creativity is valuable for business leaders?

When I say art, I mean something much broader than what hangs in a museum. The definition I’ve adopted is that art is something new that changes the world to allow itself to exist. Art isn’t going from point A to point B; it’s inventing point B.

Creativity is such a buzzword that it’s hard to dive under the surface and engage with it. We lack the language to talk about how connected creativity and commerce are. The book aims to make those connections and offer frameworks that help carve out space to explore what’s unknown and untested, because taking that risk is important to moving forward.

There’s an uneasy relationship between creativity and business. It’s uneasy because the market is based on efficiency, productivity, and being able to know the value of things ahead of time. But with creative work, you often don’t know what the value is at the moment you have to pay a price to invest in it. In the short term, business makes it hard to explore creatively, because the process is not efficient, because you might fail. Yet, in the long run, success in business depends on reinvention, on Schumpeterian creative destruction.

I hope there’s a way to remodel the way we think about the risks of creativity so we’re more honest about the possibility of failure, so we budget it in as forms of learning and tuition. Roger Bannister said of the effort to run the first sub-four-minute mile that failure is as exciting to watch as success, provided the effort is absolutely genuine and complete. I think that’s what we’re missing—that excitement and commitment around creativity.

Q: What does creativity look like in a business context? Who should be involved?

One of the great things about being human—the intellectual equivalent of having opposable thumbs—is that we can ask questions. The whole approach of art thinking is question driven. MBAs are ferociously efficient people, and I mean that as a high compliment. We know how to execute. We triage very difficult, complex tasks while juggling huge management responsibilities and extremely full schedules. But in that mode, it’s hard to sit back and think, am I just ticking off urgent tasks or am I answering the most important questions here? Am I making space for what I really care about? Am I creating space to explore, try stuff out, and fail?

It’s precisely the people who are really good at executing and managing who need time and space to think about what I call lighthouse questions—those are inquiries into challenging, potentially world-changing issues. People need the chance to figure out which issues they are uniquely suited to solving.

Beyond simply making time to think, there’s being awake at the wheel of your life—being present and paying attention to whatever you’re doing. Being connected to the value that your work creates and aware that any part of your business is open to observation, curiosity, and choice can lead to questions about what’s possible, what could be better. Or even just, wouldn’t it be cool if we tried this or that?

It can be very hard to identify the right question. That difficulty heightens the importance of strategic planning. You have to be managing towards something. Sometimes organizations will be too cautious, reverse engineering a question they know they can answer. What I’m advocating is taking on a question that is risky, that’s big enough that you might not be able to answer it. But with lighthouse questions, what’s learned in the process of failing may move the needle. And coming up with any answers would be profound.

Q: I don’t think you’re going to find a businessperson who is against creativity. On the other hand, many companies seem reluctant to fully engage the risk and uncertainty that comes with genuine creativity. What is the dynamic as you see it?

Creativity also has a reputation as loose, open-ended, and kind of head in the clouds. But it’s possible to be really rigorous about the creative process. That is, rigorous in a process sense of investigating a question as resourcefully as you can within risk management parameters, as decided in advance, to establish how much time to dedicate to the effort.

If you’re a risk manager, your job is not to be free of doubt; it’s to live in the doubt, and to navigate it well. And if you’re being creative, your job is to focus on the most important questions, trying to move forward and to make space in a corporate culture for that type of work. Many of the questions that organizations face are large, messy, and interdisciplinary in such a way that trying to answer them will require coordinated team efforts.

Q: How is the effort to answer a question organized?

Real alignment of business interests, long-term value creation, and the creative process require fully engaged people who can take risks and think independently. If you’re asking people to do that you need to give them a space—a work environment—where they can authentically be themselves.

One of the approaches I describe in the book adapts the tools of software development, such as the Scrum approach, using teams working in short sprints to iterate solutions. A team can work in a very structured way but be process driven, versus outcome driven. The risk management wrapper ensures you’re only investing the amount of time that the company can afford. There are a series of management roles and responsibilities that are conducive to letting people work as creatively as they can in this way.

When a group is working on a creative project, everyone is in unknown territory, so it’s not really possible to have a command-and-control approach. You can hold people accountable to working hard to hit process-based milestones, but ultimately your job is to create the environment that draws them out with a great deal of rigor and generosity.

Overall, the manager is trying to support something that is probably a little anathema to many corporate cultures: a holding environment, which is a space in which people feel safe enough to take real risks, and in which, if there are ruptures, they can be repaired.

Q: You mentioned specific roles. What are they?

There are three roles defined in the book that are part of the holding environment. One is the guide. That is someone who aims to draw out each person’s best talents and helps the team reflect on itself. This isn’t a guru who knows everything and is leading people towards that; it’s a manager who holds back from doing the creative work in order to guide a team that’s immersed in the weeds. Being a guide is actually extremely hard. It takes a lot of invisible work.

Another role, one of my favorites, is the colleague-friend. Ed Catmull, the president of Pixar, says that early on, every Pixar film sucks. The important thing is to get from “suck” to “not suck.” One way they do that is through directors giving each other feedback. They can say, “Look, I completely believe in your ability to make it work, but this isn’t working yet.” They offer candor, they can talk about the details of the craft, and there’s a mutual respect even if it’s not necessarily a friendship as it’s traditionally construed.

You can have the dynamic of the colleague-friend in a film development company or a finance company or in your everyday life. So much of the creative process requires that, because it’s scary and unknown, and you need someone who can help you stay intact as your whole best self in the midst of that. You need someone who can really be there with you and at the same time dive into a conversation about the work.

Finally, there’s the producer. Many things we see as highly creative or socially useful also have to pay for themselves. Say you’re trying to improve cook stoves for the developing world. If you can’t make them within a certain budget, people can’t buy them. It’s not the producer’s job to come up with ideas. The producer shoehorns ideas into an economic reality. That kind of thinking within economic constraints can be incredibly inventive work.

Thinking in an unconstrained way when you’re coming up with a lighthouse question—the guiding question that moves your work forward—is really healthy. But the reality is that most of the time, we are thinking in the midst of constraints, and so many people I talked to in the course of writing the book said, hands down, they did their most creative work when they were up against constraints.

Q: Where do you start assessing a creative project’s success or failure?

Sue McConnell, a neurobiologist at Stanford, runs a program where science students undertake senior projects in art. They’re not graded on the artistic merit of what they create. She said it’s a way for the students to learn to be productively disoriented, to get lost in the weeds of creativity. People who win the Nobel Prize probably spent years slightly disoriented as they were trying to figure out answers to world-changing questions.

In the middle of any creative project, it’s important to be wary of making judgments about success and failure. You want a period of what Carol Dweck calls a learning mindset, of just moving forward, open-endedly, with curiosity. Judging can be counterproductive, because you stop making the work to sit back to see if it is good or bad.

Beyond that, an apparent failure may well be an intermediate step on the way to success. Or something we think is a success could be pushed much further. What I think is more helpful is to get into a space of discernment, rather than judgment. Focus on what’s working and how it can be better—that’s the engine of the creative process.

Q: Could you explain the value of the portfolio approach to making time for creative work?

It’s very hard to have creative freedom when you’re worried about basic economic viability. Whether you’re thinking on behalf of a company or yourself as an individual, it’s important to ask, what is making my income stable in the short term?

Leonardo da Vinci did this. During the years he was working on the Mona Lisa, a separate large-scale public commission provided the bulk of his income. That commission doesn’t even exist anymore because he experimented with painting materials and the whole thing fell off the wall. It’s a refreshing reminder that we don’t necessarily know which thing will ultimately be most important.

It’s like investment management. The riskier creative projects are the alternative part of the portfolio. They’re highly uncorrelated, and they may succeed wildly. But most people’s risk tolerance is not high enough to make them more than a piece of what they do.

This is how most companies operate. Portfolio thinking is just making the investment in creativity a little more explicit: we’re going to dedicate x to riskier, creative projects that could be transformative.

It is the same for individuals in our careers. You can say, I’m going to work on this side project for 10% of my time, or I’m going to meet with some potential collaborators one night a week for a year, and then we can decide whether to start a company.

Sara Blakely kept her job selling fax machines for a year after she founded Spanx. The artists Christo and Jeanne-Claude famously supported their projects by selling their own preliminary sketches and drawings. They wrapped the Reichstag in Berlin in a million square feet of fabric in 1995. They created a temporary installation of 7,500 gates in Central Park in 2005. Both of those projects started in the ’70s. They needed that much time, that much runway, to get them off the ground.

Q: In the book, you describe Christo and Jeanne-Claude building up from wrapping a can to a motorcycle to these massive projects. It’s so much like a company creating prototypes, testing them out, and slowly expanding.

Absolutely. Those early stages require a lot of personal energetic leveraging of resources. It’s like the moment in an airplane when you’re trying to get off the ground, and you can hear the engines really fire.

That said, I think it’s also incredibly hard to be established, to have succeeded and to continue to invent—to be Apple, right now—while still making space for the scrappiness of the garage prototyping phase.

To extend the metaphor, an established company is cruising along at 35,000 feet. On the one hand, you’ve got a lot more room to maneuver. On the other hand, you have much more invested in flying as safely as possible because you are so far off the ground. Taking risks is a little more charged.

Interview conducted and edited by Ted O’Callahan.

Visual Arts Administration, NYU Steinhardt School of Culture, Education, and Human Development; Author, Art Thinking