Idea Incubator 13: The Most Creative Question


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glass collection of Liane Sebastian
Being creative is the best and the worst way to make money. If you have a really hot idea and it sparks a trend, you can hit it big. But if you venture into obscure innovative territory, you can end up lost in the jungle. The good news is that if you capture the pulse of the situation, understand the marketplace, and use business sense, you can build a practice that is sustaining. Making a living as a graphic designer has allowed me to learn so much about other businesses, types of audiences, buyer behavior, and what kinds of ideas will most appeal, I would never trade such perspective.

Stephanie Medlock has a different horizontal perspective through her work for the University of Chicago’s Graham School. Assigned with discovering the best presenters and courses for their curriculum, Stephanie is in the business of identifying innovative thinkers. When interviewed for my book, she said:

“Break the rules that dominate your discipline to be free and combine what you know of that field with other types of information.”
— Stephanie Medlock, contributor to Women who Win at Work

To fuel the development of a breakthrough, how you feed that process will reveal the depth of your mental connections. Here is a tool to prepare the idea-generating ingredients and lead up to the single most creative question you can ask:


Each problem has five possible situations: yours, the way you think others will react, the way others actually do react, the way they think you react, and finally, the way the audience reactions through evaluating the numbers—what really happens. Within those five setups, there are at least three solutions to discover for each challenge. Contemplate these preliminary questions towards the five viewpoints that will help decipher reality that will either befriend or murder infant ideas.

• What does your target constituent care most about?

• Who quintessentially represents your audience? How can you put yourself in that person’s shoes?

• What other fields/solutions relate to the situation or challenge?

• Who is in a different field that may offer parallels? How can you talk to them and share experiences?

• What other research/homework will fill out your knowledge (do not yet seek out what competitors are doing. Only when you are solid on a few ideas should you examine competition—but make sure to do this before moving in to development!)

When Stephanie talks about cross-fertilization, I feel that is the job of the creative mind. Originality combines the familiar in new ways. Ideas are sparks of insight. What better way to gain the vocabulary of insight than through a wide range of experiences? What I love the most about graphic design is the range of businesses I encounter. Travel is another great resource. And nature—always the best source for originality. Ultimately, originality comes down to asking simply: “What If…?

See the developing series of Idea Incubators.

Liane Sebastian, illustrator, designer, writer, and publishing pioneer


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2 Responses to “Idea Incubator 13: The Most Creative Question”

  1. Idea Incubator 24: Emotions as Creative Guideposts « Wisdomofwork's Blog Says:

    […] flexibility requires new and evolving skills, necessary to encourage creativity. #13: “The Most Creative Question” Explore the process to arrive at the single most important and impactful question. #14: […]

  2. Idea Incubator 16: Gauging Good Ideas « Idea Initiator Says:

    […] is simple enough to grasp quickly. Through combining, editing, and developing, (written about in other posts) the idea is polished to express a have business case. “One of […]

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