Creative Thinking

5 Ways Asking Insightful Questions Can Spark Creative Thinking

By Liz Alton on June 7, 2017

Are you asking insightful questions that drive breakthrough strategies, compelling content, and creative thinking? Productivity guru Tony Robbins famously said that the quality of your questions was directly related to the quality of your life. As anyone who has ever made a tough decision knows, this is largely true: the questions you ask dictate the data that you work from, which directly influences outcomes. Think about the kinds of questions that you need to ask when buying a car. The first question that most people ask is how much it costs; generally, if a car is far above or below the budget you have in mind, you're unlikely to move forward with it.

But then, if there's synergy, you dig deeper and craft a story in your mind of how that car will be used. For example, does it have enough room to fit the two kids and the big, dirty dog that you love to spend your weekends chasing around outdoors? Is the storage space enough for soccer equipment and camping gear? Does the fuel efficiency line up with your disposable income and your environmental values and all the road trips you plan to take exploring New England from end to end?

Conversely, maybe you're going for an ultra-sleek sports car that tells a story about you. What questions do you want people to ask about you? What kind of job does this person need to afford this car? What's beneath the surface of this façade to make a person crave this kind of speed, or confidently command this kind of style?

As Tim Urban, the founder of Wait But Why, said in his keynote at Forward 2016, marketers and creatives are brain tinkerers and idea surgeons. We use language to get thoughts from our brains to other people's brains-and as a result, we need to know how to get there. I would argue that questions-really good questions-are the key to great ideas, smart strategies for getting them into other people's brains, and ultimately, effective content marketing.

So if great questions lead to great marketing, that begs the question: How do we ask better questions?

creative thinking

Image attribution: Emily Morter

Focus Your Questions on Evoking a Specific Emotion

In his keynote, Tim Urban talked about the importance of connecting with people's emotions. When you can fascinate someone, anger them, or force them to lose control of their laughter because you've created something hilarious, you're on to something that's sticky and impactful. For marketers, this leads to one way to think about questions: How can they help you evoke emotions? There are many ways to consider this area.

  • What's a hook that would help make this story funny or scary or help readers feel sad or inspired?
  • How can we evoke the emotion in our readers?
  • What different emotions do we want people to feel when they're reading this and how does that connect to our calls to action and business objectives?
  • What storytelling mechanisms can help bring these emotions to the surface in our audience?

Follow the Question Train

The best questions are never "one and done" in content marketing, unless it's a transactional focus. Frame your questions in terms of a question train. Every question you ask should lead to another question. Consider that awkward stage that kids go through when they constantly ask "why?". No matter what you say, that's the follow-up question. Have you ever tried to answer that curious "why" with a rational explanation? It can take you to interesting and unseen destinations. There are a few easy ways to implement this.

  • Keep asking why.
  • Follow every answer with a question.
  • Frame the answer to your last question as a question, and focus on why it's true, how it's true, or what else it can tell you.
  • Ask an unrelated question, and try to find your way back to the current train of thought.

Lead with "How"

Stories are classically made up the five Ws-who, what, when, where, and why. That sets the context for the broader narrative. But, as one Forbes author notes, things get really juicy when you dive into "how?". Leaders often ask "how" questions to get at the underlying data that they need to make big decisions. For example, instead of asking what kind of digital experience your customers want, ask how they want to experience your brand digitally. It's specific, and allows you to explore a more dynamic viewpoint that includes:

  • Specific data points and suggestions
  • Different mechanics for achieving outcomes
  • Nuances of what's working and why it's working
  • Who is connecting with your content and at what level

Focus on the Positives

Recently, in a Facebook post, an angel investor said that in the first five minutes of any conversation with a founder, he liked to focus on the positives. What success had the company had? How did the product or service help the market? What did he intuitively love about their solution, team, positioning, or approach?

So much of our time-from stress testing strategies to prevent failure to our constant obsession with self-improvement-is spent identifying what's wrong and trying to fix it. How does that impact the direction of your content strategies? If your focuses begin to multiply and take a central role in your strategies, then dedicating some time to asking questions about positives might help drive a better outcome.

  • What campaigns are succeeding now and how are they getting traction?
  • What makes our customers love us and how can we expand on that value?
  • How are the brands that are winning in our space doing it? What do we love about their approach?
  • How are we completely different and unique from other companies in our vertical?

Frame Your Question from Another Point of View

Recently, I was developing a go-to-market strategy for a healthcare technology product. As part of this process, I spent a significant amount of time evaluating past reports, market trends, and the competitive environment. However, it was only after I got into the room with different players on the team that I got real insights. One in particular emerged quickly: Every individual saw the process differently.

For example, the VP of sales could tell me what customers were asking about directly and what their reps wanted in terms of content. The field marketing manager could tell us all about what competitors were doing at the trade shows she attended. The industry lead had a 30,000 foot point of view that was priceless in organizing the trends. The real breakthrough came when we considered what questions I should be asking as part of the strategy. Each of them suggested radically different avenues of inquiry.

For content marketers and writers, it can be useful to think about how different players in the company are likely to approach the problem. Insightful questions for sales are likely different from insightful questions for delivering customer service. The most creative thinking you can do across campaigns may be an amalgamation of these different perspectives.

In my work as a writer, content marketer, and generally as a human being, my theory is to never stop asking questions. However, the important "hack" isn't just to keep asking-it's improving your ability to ask the questions that matter. Whether you're sifting through the data to find a compelling story or you're helping a client achieve a breakthrough idea for their next campaign, a commitment to asking insightful questions is critical to creative thinking, marketing innovation, and developing the kind of content that you'll be proud to call your own.

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Featured image attribution: Freddy Marschall


Liz Alton

Liz Alton is a technology and marketing writer, and content strategist, for Fortune 500 brands and creative agencies. Her specialties include marketing, technology, B2B, big data/analytics, cloud, and mobility. She's worked with clients including Adobe, IBM, Hewlett Packard, Twitter, ADP, and Google. She holds a bachelor’s degree in journalism and an MBA. She is currently pursuing a master’s in journalism from Harvard University.