Updated: Jennifer Riel is the managing director for knowledge infrastructure at the Martin Prosperity Institute at the University of Toronto's Rotman School of Management.

Solving a hard problem can be vexing, as it requires working doggedly through potential solutions to find the correct answer.

But some problems are not just hard but wickedly hard in their unconventionality and scope, and the usual problem-solving skills are not effective, said Jennifer Riel, the associate director of the Desautels Centre for Integrative Thinking at the University of Toronto’s Rotman School of Management.

“As you attempt to solve the problem, it starts to change,” said Riel, citing some of the characteristics of what she and her colleagues call “wicked” problems. “There are no starting and ending rules. You don’t ever actually know when you’re done solving the problem.”

Leaders can solve wicked problems, she said, by breaking down conventional thought patterns and developing fresh ideas through the models of integrative thinking and design thinking.

RielRiel, who holds an MBA from Rotman, said these thinking strategies typically have been focused on business management issues but can work just as well for other types of organizations, and even individuals.

Riel has created and led workshops for companies such as Four Seasons and AstraZeneca. She also collaborates closely with Martin on his writing, including the 2007 book “The Opposable Mind: How Successful Leaders Win Through Integrative Thinking.”

She spoke with Faith & Leadership about the nature of wicked problems and some alternative approaches to solving them.

Q: Could you explain the difference between a hard problem and a wicked problem?

There are kinds of problems in the world, in particular in public policy, where the problem is not just big but almost overwhelmingly big. And you can’t see your way clear from the beginning to the end.

So you are as much designing your process to solve the problem as you are solving it, and that’s what makes it so tricky and pernicious. The term “wicked” came to be applied to these problems in part because it really does convey this sense of just how daunting it can be to be faced with a problem like, How do you provide health care to the people of the United States or the people of Canada?

Those problems look a little different from hard problems, and they require different skill sets.

We are trained really well in school to manage hard problems. Even when you get into higher levels of education, there still tend to be these reasonably structured problems. There’s a way of working your way through this complicated case that brings you to the answer related to the lesson you’re trying to learn in that class.

Wicked problems don’t work that way. They’re not pre-structured. They cross institutional barriers. They don’t belong to any one person, any one philosophy, any one organization, and so it makes it just way harder to come to an answer.

Q: How do you know you have a wicked problem and not just a hard problem?

I think life is a wicked problem, and there are hard problems within life.

How do I help my child determine which engineering program to go to? That’s a hard problem. There are a lot of engineering programs, and so you would go through your process.

That is a very different thing from having your child coming to you and saying, “What should I do with my life? What can I do that will provide me with meaning and passion?” That’s a wicked problem. How do you even start to think about a problem like that?

Q: Can you give an example in an organizational setting of a wicked problem and how it was solved ?

Steve Jobs was a master at dealing with wicked problems, and when he came back to Apple [in 1996], it was in a very bad place. They had the success of the Macintosh, and then they really struggled.

Most CEOs would come back and say, “How do I sell more computers? We’ll have to expand the number of consumers who are interested in my products. We’ll have to hire a chief marketing officer.” It’s a hard problem -- “How do I sell more computers?”

Jobs came in and asked different kinds of questions about what could that company even be. He famously said his objective was to make a dent in the universe. He asked, “How do I transform how people interact with each other and the devices that enable them to communicate?” It’s a totally different kind of thing.

The company went on to build the iPod, which is a fun little product but not much different from a whole bunch of other MP3 players that already existed at the time. But then Apple designed a whole system, created iTunes and an integrated marketing campaign that got people very excited about it.

Steve Jobs transformed what his company was about, which was how you interact with the devices in your life, and how an MP3 player wasn’t just about music but who you are as a person.

Another example that I like is Research in Motion. The BlackBerry guys are struggling a little bit [now], but think about what they did originally, which was to say, “How do people want to connect to their office when they’re not there?”

They first made digital pagers, and the notion that you could design something that would enable you to read email didn’t seem utterly transformative until it ended up in the hands of [RIM President] Mike Lazaridis, who asked, “How would you design this in such a way that would actually connect you to the people that you have left in the office?”

And that’s really what he did. He didn’t ask, “How do I make a better pager?”

Q: When you work with organizations and people in leadership, how do you go about helping them identify and address their wicked problems?

We work with a wonderful group at the Rotman School at the University of Toronto Business Design Initiative who call themselves DesignWorks. They were created out of some work that our dean, Roger Martin, did with Procter & Gamble, along with Dave Kelley [of Stanford University’s Plattner Institute of Design] and Patrick Whitney [dean of the Institute of Design at Illinois Institute of Technology].

Procter & Gamble was interested in spurring innovation internally through design. They had this insight that designers were able to tackle wicked problems in a way that didn’t seem to be happening organizationally.

So David, Roger and Patrick created a three-part process for generating innovation around wicked problems in an organization.

They take an ethnographic approach, using qualitative research and post-quantitative research -- really attempting to understand what the needs are. From there you move into the process of “ideating,” a new term for me before I met designers. It involves trying to generate ways of dealing with that need and prototyping lots of answers, testing them, going back to the users, and playing around with the ideas.

The third stage, that is so often neglected but most important, is saying, “How do I take that insight, that new innovation, and have it make sense with what I already do, with the strategy of my organization? How do I get people in my organization to understand how it fits and how to implement it?”

Q: Can you explain the term “design thinking”?

Design thinking is connected to integrative thinking, but it’s not exactly the same thing. One way of thinking about integrative thinking is as an overarching approach to problems that boil down to a couple of options that you can’t quite imagine coming together.

First you need to do a deep dive into the models in front of you, but then you need to get creative about combining those two ideas.

Design thinking is a way of doing that. Design thinking in its most simple form is applying the tools and thinking of a designer to business problems, although it extends considerably further, to a whole process and methodology that you can apply to almost any kind of problem.

You adopt the three-step approach of deeply understanding the user, ideating around that need, and then integrating it into a business model that makes sense.

Q: What if you are a person who works in an organization where you’re not the leader? If you don’t see that kind of culture around you, how do you employ design thinking in your own work?

Roger is asked this question a lot, as am I. I always turn to his answer, because it’s an incredibly helpful one. It is that, ultimately, you can’t transform the leaders of your organization. You can’t take upon yourself that it is your job to make your organization a design-thinking or integrative-thinking organization if you’re working from within it. That’s just too big and too hard a job.

But you do have something over which you have domain. You have a little team or a project. Or you have the things that are within the scope of your work, and to those you can apply this process. Try it, experiment, play, and see what comes of it.

Over time, people will observe that you are coming to these interesting and better answers, and then you get the next-higher job. Then you have more of that big pyramid of the organization that you can influence. Eventually, you get to the very top of the organization.

When we talk about integrative thinking, we often cite examples. We can point to A.G. Lafley, former CEO of Procter & Gamble, and say, “Here’s what he was able to do with this massive global organization.”

But I find it hard to believe that he became CEO and then started being an integrative thinker. That doesn’t make a lot of sense to me. I think he applied this way of tackling difficult choices early on in his career. By the time he was CEO, he was very good at this kind of thinking, and that enabled him to tackle the really big problems.

Q: Is there application of these ideas beyond the world of business?

While most of our work has been in the world of business, I think it is a broader application than that. I think all organizations face these kinds of issues. I think individuals face these kinds of issues.

And so, even if we look at politics or what’s happening in the news -- we get a lot of questions about Occupy Wall Street -- we need to look at the two sides of that debate. In most political debates, there doesn’t seem to be any listening at all.

So either Goldman Sachs is the devil or these kids who are occupying the parks are anarchists who don’t know anything, which is not helpful.

There is a wicked problem at play in the capital markets. The 2008 financial downturn gave us a big notice that something was very wrong, and the only way for us to come to a better answer and to prevent 2008 from happening again is to really engage with both sides of that debate -- really dive in and understand what they see -- and create a better answer out of that.

Q: If you’re the leader of an organization and you’re facing a wicked problem or you know that one will come along, how do you encourage the kind of problem solving that actually results in that elusive final resolution ?

I think there are a couple of key things to do. One is to demonstrate through your actions your own openness to floating ideas, to exploration and creativity. People see what their leaders do and recognize that it is what they do, rather than what they say, that reveals what truly matters. So I think you should demonstrate as much as you can that openness, curiosity.

The attitude towards failure is hugely important. If failure is punished, it will kill innovation in an organization. That’s my true belief. As soon as you start punishing people for trying new ideas, they will stop trying new ideas.

But that doesn’t happen if there’s a culture of experimentation, where you say what you want to do, predict what the outcome will be, try it, and then measure what happened versus your prediction.

If you create a culture like that, it can really help spur people to want to tackle these wicked problems and feel inspired and capable of doing so.