How Being Curious Children Led Two Internet Pioneers To Innovation

Asking questions doesn’t show incompetence–it’s how great leaders innovate, explore, and disrupt.

How Being Curious Children Led Two Internet Pioneers To Innovation
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Technology guru, author, and father of the term “virtual communities” Howard Rheingold and filmmaker Tiffany Shlain, who co-founded the Webby Awards and the International Academy of Digital Arts and Sciences, are Internet pioneers in their own right. But they have one important thing in common: They ask provocative questions.


Growing up in Phoenix, an “extremely de facto segregated city” at the time, Rheingold says he began asking questions when he refused to be put into the box people wanted to put him in. Lucky for him, he had an art teacher for a mother who was “quite well known for being the exact opposite of the button-down, all-the-desks-in-a-row teacher,” he said.

“She very strongly defended my right to color outside the lines,” Rheingold says.

People tend to get shut down from a young age: When children ask too many questions, they are shushed. When their curiosity leads them outside of the box, they are quickly ushered back in. It’s an unfortunate habit perpetrated by adults and it’s one that threatens to hamper creativity and innovation.

If there is one common thread I have found among great leaders, it is that they are willing to ask questions about the things they don’t know, and it’s what almost always leads them to great new discoveries and innovation.

How can we engage technology as an authentic form of connection?

Tiffany Shlain’s very supportive and open-minded parents made sure she wasn’t one of those children who was led back into a box. Her father–visionary thinker, educator, and surgeon Leonard Shlain–constantly encouraged her and her siblings, instructing them not to be afraid to ask big questions. His favorite motto was, “If you’re not living on the edge, you are taking up too much space.”


Shlain clearly took that advice to heart. In high school, she and a friend wondered what it would be like if they could use their modems to connect with students in enemy countries and ask them what their families are like or what they were reading and discover what they had in common.

Together they wrote up a proposal calling for a new organization named Uniting Nations in Telecommunications and Software, and the initiative got Shlain an invitation to speak about her ideas as a student ambassador to the Soviet Union.

Technology hasn’t left her mind since. Widely considered an Internet pioneer, Shlain founded the Webby Awards in 1996 before becoming a world-renowned filmmaker.

Her film studio and lab, The Moxie Institute, creates films, books, theater experiences, and Internet experiments around social issues using emerging technologies.

Her latest venture is a project she calls cloud filmmaking, in which people from all over the world collaborate via social media to make one film. Its purpose is to connect people together by focusing on what they have in common, not on what divides them.


“Whenever there is a new technology, I ask myself, ‘How can we engage that technology in an authentic form of connection?’” she says. “I’m interested in why we do the things we do and why we are all so intoxicated with technology.”

How Can We Learn From Each Other?

If Shlain is considered an Internet pioneer, Rheingold is often called the Internet’s first citizen. A founder of HotWired and Electric Minds, he is widely credited with coining the phrase “virtual community” and predicting the rise of collaborative internet ventures like Wikipedia.

A lecturer at Berkeley and Stanford, Rheingold begins his classes by asking his students to write down the three most important questions they’d like to have answered by his course. Students meet in groups and narrow down the questions until the entire classroom is left with five questions. The students then write up their answer to one of the questions, and pass it along to a second team, who will take what they’ve done and expand it and increase its depth. It will then get passed onto another team.

It’s similar to a process I call catalytic questioning, which I teach to business leaders. It involves having employees come up with nothing but questions about an important issue to solve. From the list of questions, the group identifies the three or four that will disrupt the status quo if answered. In Rheingold’s case, his students’ questions essentially set the course agenda.

The student-led questioning process came about because of his own provocative questions: “What if we eliminated the teacher from the classroom? What if a group of people wanted to learn something but they didn’t have an instructor?”


The question is the foundation of his new venture, the Peeragogy Project, which brought together a group of people to create a handbook for self-organized peer learning groups–in a way, it’s the ultimate answer for people who are filled with questions.

“Collaborative inquiry is really at the heart of what I’m doing,” Rheingold says. “Students are working on projects together and pursuing questions together. It’s collaborative inquiry and collaborate learning.” He believes this collaboration–driven by boundless inquiry–helps people work smarter.

Seeking mindfulness in a digital age

Questioning plays a big role in Rheingold’s own life, especially when it comes to the center of his life’s work: technology. In his book, Net Smart, he writes:

“[T]he most enriching, least harmful way for me to live in my own computer-mediated world is to cultivate an occasional but ongoing inner inquiry into whether my own activity of the moment is really as significant as what is happening in the rest of my life at each moment…And while I’m asking questions, where is my body while my mind scurries through cyberspaces? It’s easy to ask oneself, “What do I think I should be doing right now?” Answering it usually takes work. The process of trying to address the question in your own context is the work of learning digital mindfulness.”

It may seem ironic that someone who is so immersed in technology wants to get away from it all. But Rheingold is not alone: Tiffany Shlain unplugs for a full 24 hours, starting every Friday night at the beginning of Shabbot. It gives her time to spend with her family and opens up her two young daughters to asking more questions.

“I don’t ban them from technology, but I’m also really careful to make sure they understand the different modes of curiosity in the real world,” she explains.


Howard Rheingold and Tiffany Shlain are two innovators who are using the power of questions to unlock creativity in themselves–as well as in the next generation.

Why is this so important? Because by asking more questions, we arrive at the right questions–those we don’t know that we don’t know. It is a crucial process for businesses because it is those that are not aware of the questions that are most likely to be disrupted.

Hal Gregersen is the executive director of MIT’s Leadership Center and co-author of The Innovator’s DNA. He is also founder of the 4-24 Project, an initiative dedicated to rekindling the provocative power of asking the right questions.