Struggling to find stories to tell? Start asking questions.
Creativity Creative Thinking

How Good Questions Lead to Great Digital Storytelling

7 Minute Read

I know more about my grandmother than most any member of my family, because I spent years asking her questions about her life. (As a child, I loved asking questions—much to the chagrin of those around me.) The right inquiry started her off on a long, beautifully recounted story. Some were sad, others were touching or funny, and some were downright scary. To this day, I tell my father stories he never knew about his parents’ lives, and even his own early childhood—not because he didn’t care, but because he never asked.


In digital storytelling, as with any other medium, curiosity is key. Why? Because great stories demonstrate a respect for (and understanding of) their audiences that you can only develop by asking the right questions. Through the stories of others, we learn what makes others tick and what really matters to them. Stories are also a way to relate: by asking people about their experiences and sharing our own similar stories, we demonstrate empathy and create emotional connections.

In short, curious people—and curious brands—get to hear all the best stories. And when you make a habit of asking questions, you’ll never find yourself struggling for ideas or searching for new ways to connect with your readers on a deeper level.

As a content marketer, part of your job is to tell engaging stories about your brand, your product, your customers, your industry, and any other topic that matters to your audience. The good news is that everyone around you is a potential source of stories that could lead to great blog posts, videos, case studies, or social media campaigns. Finding those stories simply requires a little creative thinking, a curious mind, and the right questions.

So, who do you ask?

1. Your Customers

It’s sales and marketing 101: Know thy customer.

If you don’t know who they are, what they want, and what they’ll want in the future, you can’t offer the products and services they need or create content that will engage them.

But what’s the best way to learn about your customers? Sure, you can (and should) track online behavior, analyze marketing metrics such as email opens and click-through rates, do A/B testing to learn what content appeals to what audiences, and consider all the other digital analytics available to you.

You can also ask your customers questions. What matters most to them? What are they proud of? What do they fear? What challenges are they trying to overcome? What challenges have they already overcome, and how did they do it? What meaningful experiences have they had that are relevant to your brand? What experiences do they want to have? What do they wish they knew? What do they wish other people knew?

Getting these answers could be as simple as posting open-ended questions online, or holding contests on social media soliciting stories that are somehow related to your brand or industry. For example, if you sell to parents, you could ask about their proudest, or perhaps their most embarrassing, parenting moments. If you sell technology, you could ask about the most creative ways customers have ever used your products. If you sell toothpaste, you could ask for stories about the first time customers lost a tooth.

Coming up with the right questions requires some creative thinking, but the more questions you ask, the better chance you have of stumbling across great stories. Or at the very least, uncovering insights that help you tell stories to which your customers can relate.


2. Your Colleagues

Marketers spend plenty of time interacting with their audiences, but most don’t get nearly as much face time with customers as salespeople, customer service reps, and other front-line workers. These people have experience and insights that can help you craft compelling digital stories.

In B2B companies, sales can be a particularly valuable resource. If salespeople are asking the right questions during the discovery phase and throughout the sales process, they know what matters to your customers, what challenges they’re trying to overcome, and what keeps them up at night. And they’ve probably heard some great stories along the way.

Other employees in the company might know some customer stories as well. They might also have their own stories that paint your brand in a positive light or give audiences an inside look at the company. For example, your coworkers in the manufacturing department could offer an interesting take on how your products are made. Your designers and engineers might be able to tell insightful tales about where they see the industry headed. Your service technicians probably have a long list of anecdotes about some unique problems they’ve seen or interesting situations they’ve encountered on the job.

By asking your coworkers about what they do, what they’ve seen, and what they foresee for the future, you’ll hear some great stories, plenty of which might be worth telling your audience.

3. Yourself

You’re not just a storyteller. You’re also a consumer of stories. So what you find engaging or compelling—about your brand, your product, your customers, or your company’s area of expertise—may captivate your audience as well.

When the Content Standard asked Radiolab founder Jad Abumrad where good stories come from, he explained:

You just kind of get hooked by something. It’s very much the way that anyone discovers anything, except you’re always looking. You’re reading a lot, you’re spending 3-4 hours a day looking, looking, looking for stuff. You’re on the phone—a thousand phone calls for a thousand ideas that won’t go anymore—to find the one that does. You get a little bit of that brain fever. Some question or idea or experience presents that feeling to you: Wow, I don’t know how to feel about this. That’s exciting. I have so many questions. You then spend the next six months to a year trying to painstakingly reconstruct the story to give someone else that very same feeling you had at the beginning.

Of course, brand storytellers don’t often have six months to a year to create content. But the principles still apply: Ask yourself what piques your own interest and gets you curious to learn more. Then find a way to tell those stories.

Questioning yourself is also a great way to brainstorm new ideas and storytelling strategies. As Catrinel Bartolomeu, head of content and digital marketing at Oz Content Technologies, puts it, “How do you get to know about other people? You ask them lots of questions. Treat yourself and your ideas like strangers and you might find out something new.”

Ask yourself what gaps you see in your storytelling, what’s happening in the news that’s related to your brand, what interesting stories you could tell about the history of your brand, and what unique angles you can add to the stories you’re reading about your industry. By interviewing yourself and perhaps your peers in the marketing department, you can jump-start the storytelling process and find new narratives to explore.

Keep an Open Mind

When you set out on a mission to ask the right questions, you have to leave yourself open to whatever unexpected news you might uncover. For example: I remember going out to dinner with a high school boyfriend and his family. I was asking his mother and father questions about their relationship—how they met, how they got together, when they got married. The mother’s answer to this last question stunned her oldest son. “That’s right,” she told him with a gleam in her eye. “I was already pregnant with you.” He wanted to know why she’d never told him this. “Because you never asked,” she said. “I’ve been waiting 18 years for you to do that math.”

Okay, so you might not learn something that unexpected, but you never know what your customers, coworkers, or subconscious might have to share. Keep your digital storytelling strategy open and make room to share the stories that surprise you. You might find they’re just the kind of stories your audience craves.

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Taylor Mallory Holland is a freelance writer, editor, and content marketer specializing in technology, healthcare, and business leadership. As a content strategist, Holland contributes thought leadership content for some of the world's top brands, including Samsung, IBM, BlueCross BlueShield of Tennessee, and UCLA's David Geffen School of Medicine. She has been a contributor for The Content Standard since 2014.

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