10 Creativity Challenges to Exercise Your Creative Confidence

10 Creativity Challenges to Exercise Your Creative Confidence

Image for postCreative Confidence Cover

I recently read ?Creative Confidence? by Tom Kelley & David Kelley. It is an insightful, compelling narrative on how to unlock, nurture, and strengthen the innate creativity that lies within us all. In the book, the Kelley brothers demonstrate that creativity is a mindset, a way of thinking, and a proactive approach to finding new solutions. We may not all be artists, but we can be more creative lawyers, doctors, managers, or salespeople. Drawing on stories from their work at IDEO and the Stanford d.school, the Kelleys show us how to tap into the wellspring of creativity and imagination when tackling the problems we encounter. Moreover, they reveal specific strategies to unleash that creative spark within us. Creativity and the ability to innovate are like muscles ? the more we use them, the stronger they get.

According to Julie Zhuo:

A person with creative confidence understands how to strike the balance between certainty and uncertainty. He/she understands and accepts that uncertainty, false starts, and mistakes are part of the creative process, but he/she also projects a sense of stability and progress to those around her.

There is a whole chapter in the book that presents the tools to help you practice unlocking your creative thinking as a bridge to creative confidence. In this post, I will share these tools to help you flex your creative muscles. If you have practiced Design Thinking exercises before, you will find these challenges quite familiar. I am fortunate to take an Innovation Through Design Thinking class during my semester abroad last year and have been able to apply this approach to all the problem-solving / innovation types of work I have encountered.

Creativity Challenge #1 ? Push Yourself To Think Divergently and Creatively

Actively engaging in exercises that foster divergent or unconventional thinking can encourage the generation of ideas. When you are searching for innovative solutions on your own, mind-maps can be a powerful way to come up with or to gain clarity about a topic of exploration. They are extremely versatile, and we use them all the time. They help you chart the recesses of your mind surrounding one central idea. The further you get from the center of the map, the more hidden ideas you can uncover.

Image for post

Tool: Mindmaps

Participants: This is usually a solo activity

Time: 15?60 minutes

Supplies: Paper (the bigger the better) and pen


1. On a large blank piece of paper, write your central topic or challenge in the middle of the paper and circle it.

2. Make some connections to that main topic and write them down, branching out from the center as you go. Ask yourself, ?What else can I add to the map that is related to this theme?? If you think one of your ideas will lead to a whole new chapter, draw a quick rectangle or oval around it to emphasize that it?s a hub.

3. Use each connection to spur new ideas.

4. Keep going. You are done when the page fills or the ideas dwindle. If you are feeling warmed up but not finished, try to reframe the central topic and do another mindmap to get a fresh perspective. If you feel you?ve done enough, think about which ideas you would like to move forward with. Each challenge presents an opportunity for innovation.

Creativity Challenge #2 ? Increase Your Creative Output

One simple way to have more ideas in your arsenal is to start keeping track of them as they occur.

Image for post

Tool: Fifteen Seconds of Brilliance

Participants: This is a solo activity

Time: 10 minutes per day

Supplies: Paper and pen, or a digital means of keeping notes


When you have an idea or observe something intriguing, take note of it. The actual means of capturing the idea doesn?t matter as much as having it with you at all times. Choose a method or a technology that fits with your lifestyle and your personality:

Digital tools are great, but paper still works exceptionally well.

Whiteboard market in household.

On the iPhone, Siri will let you dictate a quick mental note. An increasing number of options also exist on other platforms.

Your laptop or tablet has all kinds of notepad applications. But you?ll get more functionality out of purpose-built programs like Evernote, specifically designed to store such ideas.

Creativity Challenge #3 ? Jump Start An Ideation Session

The goal of this challenge is to push people to test their creativity by turning circles into recognizable objects in a very short period of time.

Image for post

Tool: Thirty Circles Exercise

Participants: Solo or groups of any size

Time: 3 minutes, plus discussion

Supplies: Pen and a piece of paper (per person) with 30 blank circles on it of approximately the same size


1. Give each participant one Thirty Circles sheet of paper and something to draw with.

2. Ask them to turn as many of the blank circles as possible into recognizable objects in 3 minutes.

3. Compare results. Look for the quantity or fluency of ideas. Ask how many people filed in 10, 15, 20, or more circles? Next, look for diversity or flexibility in ideas. See if the ideas are derivative or distinct. Did anyone ?break the rules? and combine circles? Were the rules explicit, or just assumed?

Creativity Challenge #4 ? Learn From Observing Human Behavior

A fundamental principle of innovation or creative thinking is to start with empathy. On the path from blank page to insight, sometimes people need a tool to help with what comes next: synthesis. You?ve gone into the field in search of knowledge, meeting people on their home turf, watching and listening intently. But synthesizing all that data can be a little daunting. Take control of your field observations by organizing them with an ?empathy Map.?

Image for post

Tool: Empathy Maps

Participants: Solo or groups of 2 to 8 people

Time: 30?90 minutes

Supplies: Whiteboard or large flip chart, Post-its, and pens


1. On a whiteboard or a large flip chart, draw a 4-quadrant map. Label the sections with ?say,? ?do,? ?think, ? and ?feel, ? respectively.

2. Populate the left-hand quadrants with Post-its that capture each of your individual observations, using one Post-it per idea. Place observations about what people DO in the lower-left quadrant, and place observations of what people SAY in the upper-left quadrant. Try color-coding your observations, using green Post-its for positive things, yellow Post-its for neutral, and pink or red for frustrations, confusion, or pain points. The key is not to record everything, but instead to capture what stands out.

3. When you run out of observations on the left side, begin to fill the right side with Post-its, inferring what people THINK in the upper-right quadrant and what they FEEL in the lower-right quadrant. Pay attention to people?s body language, tone, and choice of words.

4. Take a step back and look at the map as a whole. Try to draw some insights or conclusions from what you have just written down, shared, and talked about. These questions serve as a good prompt for a discussion of insights. What seems new or surprising? Are there contradictions or disconnects within or between quadrants? What unexpected patterns appear? What, if any, latent human needs emerge?

Creativity Challenge #5 ? Encourage And Accept Constructive Feedback

To practice creative confidence on a team, members need to feel free to experiment, even during early efforts when results will be far from perfect. For that experimentation to translate into learning, however, at some point you need feedback, in order to identify weaknesses and make adjustments the next time. We all instinctively know that constructive critique is essential. And yet it can be hard to listen to and absorb feedback without letting our egos and defensiveness distract us from what may be a valuable message.

Image for post

Tool: I Like / I Wish

Participants: Groups of any size

Time: 10?30 minutes

Supplies: A means of recording feedback. For example, in a large group, keep a Word document open and type notes in real time. In a smaller setting, Post-its or index cards will work


1. Set the tone for a constructive conversation and explain the ?I Like / I Wish? method.

2. The participants take turns, sharing I Like / I Wish statements, while the facilitator records their statements. Make sure people receiving feedback just listen. This is not a time to defend decisions or challenge the critique. Ask everyone to listen and accept it as a well-meaning offer of help. You can ask for clarification and engage in further discussion at a later time.

3. Stop when participants run out of things to say in both the ?I like? and ?I wish? categories.

Creativity Challenge #6 ? Warm Up A Group

Creativity thrives amidst free-flowing social discourse. To get a room full of strangers to innovate, you may want to begin by breaking down some social barriers. When this exercise is done right, the room will be abuzz with chatter and laughter, and participants will be more open to what comes next.

Image for post

Tool: Speed Dating

Participants: Pairs in groups of any size

Time: 15?20 minutes total, 3 minutes per round

Supplies: Paper printed with a set of questions for each participant. Several different sets of questions will be needed to accommodate the entire group


1. Give each person a list of open-ended questions. Several different sets of questions should be spread throughout tables in the room so that people aren?t continually being asked the same questions.

2. Ask each person in the room to pair up with someone they don?t know very well or have never met. This may involve getting up and moving seats.

3. Have one person in each pair ask a question from the list. Allow 3 minutes for the other person to answer.

4. Have each pair switch roles and repeat, asking a different question on the list.

5. Tell everyone to find a new partner and repeat the process for a couple more rounds.

Creativity Challenge #7 ? Eliminate Hierarchy To Improve Idea Flow

While Speed Dating is useful in situations where people don?t know each other well, sometimes in group meetings you will encounter the opposite problem: a group where people know each other too well. Or, more specifically, a group in which hierarchy is so well established that the more junior members in the room self-edit and defer to the executives rather than putting their best ideas on the table. To reduce hierarchy and self-censoring, we use an experiment called ?nickname warm-up.? Using a stack of colorful names the instructors have prepared in advance, the activity is a way to temporarily level out the organization during a creative working session. Each participant is given a persona to allow them to ?try on? new behaviors.

Image for post

Tool: Nickname Warm-up

Participants: Groups of 6 to 12 people per facilitator

Time: A few minutes per person

Supplies: Name tags for all participants with the fake names written out. A hat and a ball for each facilitator


1. Each participant reaches into the hat, draws out a name tag, and puts it on. Use names that lend themselves to humor and emotion. Teams tend to produce their best work when the group is having fun. Some of the monikers can imply a big dose of street credibility, while others suggest quirky personalities.

2. The facilitator gathers the group in a circle and tosses the ball. Whoever catches it introduces themselves using their new nickname and then tells a short story about how they acquired this nickname as a child.

3. After their self-introduction, they toss the ball to a new person, until everyone has had a chance to share their new name and story.

4. The rule for the rest of the workshop ? strictly enforced ? is that everyone must use only these nicknames when referring to themselves or others.

Creativity Challenge #8 ? Empathize With Customers, Employees, And Other End Users

One way to develop more empathy with ? and gain new insights about ? your customers is to look beyond the narrow definition of your offering and consider the customer?s total experience. The more broadly you define the customer experience, the more opportunities you can identify for improvement. A journey map helps you think systematically through the steps your customers ? internal or external ? have when they interact with your product or service.

Image for post

Tool: Customer Journey Map

Participants: Solo or groups of 2 to 6 people

Time: 1?4 hours

Supplies: Whiteboard or Post-its


1. Choose a process or journey that you want to map.

2. Write down the steps. Make sure to include even small steps that may seem trivial. The goal is to get you to consider the nuances of the experience that you may normally overlook.

3. Organize the steps into a map. Usually we display the steps sequentially in a timeline. Your map may include branches to show alternative paths in the customer journey. You could also use a series of pictures or whatever method fits your data.

4. Look for insights. What patterns emerge? Anything surprising or strange? Question why certain steps occur, the order they occur in, and so forth. Ask yourself how you might innovate each step.

5. If possible, show the map to people familiar with the journey and ask them what you?ve overlooked or gotten out of sequence.

Creativity Challenge #9 ? Define A Problem To Work On

Innovators often face the task of which challenge to focus on or how to frame a challenge they are given. Talking about problems doesn?t necessarily inspire ideas or energize you to act on them. Nor does wishful thinking. The Dream/Gripe Session helps you translate those discussions into creative thinking challenges you can start to tackle.

Image for post

Tool: The Dream/Gripe Session

Participants: Pairs in groups of any size

Time: 15?30 minutes

Supplies: Pen and paper


1. Decide on a topic for discussion. The dreams and gripes may relate to internal matters like the culture of the organization or external ones like interactions with customers.

2. Pair up with another person and select one person to go first.

3. Partner 1 airs his or her dreams and gripes for 5 to 7 minutes while Partner 2 listens and takes notes.

4. Partner 2 reframes the dreams and gripes into open-ended questions that makes for good innovation challenges. Start with the phrase ?How might we??? A good ?How Might We? question should not be so narrow that it suggests a solution. Initially, you are just trying to capture the problem, not jump to possible solutions. It should also not be so broad that it stymies the flow of ideas (rather than generating them). A good ?How Might We? question should allow someone to easily come up with 10 different ideas. Partner 2 should aim for 3 to 5 well-framed innovation challenges and share them with Partner 1.

5. Switch roles and have Partner 2 air dreams and gripes while Partner 1 listens and then offers ?How Might We? innovation challenges.

6. (Optional) If you are doing this in a group setting, compare lists of all the innovation challenges across the pairs. Look for patterns, themes, and common issues. This should help focus the discussion and suggest an opportunity for what innovation challenge to take on next.

Creativity Challenge #10 ? Help Your Group Understand Innovation Thinking

The exercise uses a simple object that most people carry with them, as a prop to discover needs, design and prototype solutions, and get user feedback. It gives everyone a chance to cycle quickly through the human-centered design process.

Image for post

Tool: The Wallet Exercise

Participants: Pairs in groups of any size

Time: 90 minutes, plus preparation

Supplies: The facilitator?s guide includes a complete list of instructions, worksheets, and prototyping materials. The instructions and worksheets can be printed out for each participant or projected on a screen. Provide prototyping materials


1. Participants pair off, with one starting as the interview/anthropologist, while the other plays the part of the prospective customer. The interviewer spends a few minutes understanding and empathizing with the other person. The interviewee/customer takes out his or her wallet, and they have a discussion about the items inside and the meaning attached to them. The interviewer asks questions to see how the wallet fits into the customer?s life, looking especially for problems or friction points associated with the wallet. After just a few minutes, the facilitator calls time, and the team members reverse roles, with the interviewer in round one becoming the customer in round two.

2. After the participants have had a chance to understand the customers and their wallets, the next step is to develop a point of view about their latent needs and missed opportunities with regard to their wallets. Those need-based points of view can take the form of a sentence like ?My customer needs a way to ? [user needs] ? in a way that makes them feel ? [meaning/emotion] ? because ? [insight].

3. In a form of mini-brainstorming, each participant generates a few concepts for new objects ? they may not be physical wallets at all ? that satisfy the needs highlighted by the point of view developed in step 2.

4. In the most kindergarten-like phase of the wallet exercise, participants create the roughest of prototypes to bring their ideas to life. Using an eclectic mix of materials like construction paper, duct tape, pipe cleaners, and binder clips, the participants will build prototypes just good enough to make their idea tangible so that they can get feedback from their future customer.

5. Using their storytelling skills, a selection of participants ?pitch? their new-to-the-world wallet concept to their customer and/or to the room at large.

There is an enormous number of stories and tips contained in Creative Confidence. I have shared here the 10 creativity challenges that you can practice to be more creatively confident. Some psychologists claim that you have to practice a new behavior for 21 days before it begins to become a habit. The operative word is ?practice.? The weeks, months, or years spent thinking about new behaviors don?t count. So pick your favorites or create some new experiments of your own. Start accelerating down the runway now if you want your new skills to take flight.


No Responses

Write a response