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Powerful Questions in a Digital World

Matthew Doan
Design and Tech.Co
Published in
4 min readMar 14, 2019

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Our world is moving at lightning speed. The “linear”, conglomerate business models of yesteryear are giving way to on-demand, subscription, and networked ones. And the underlying technology infrastructures powering these moves are nimble, elastic, and in a state of constant upgrade. If you’re not consciously extending your periscope above water, it can seem like everything is pre-destined at this point. Our jobs and our decisions can seem formulaic. AI and the robots are coming, they say, so where do we fit in? What power do we have in this tech-driven world?

As individuals and organizations, we can choose to go with the flow and “zombie” through our days, or we can embrace our humanity: we can ask great questions and make things better.

Here’s a grounding example: in the early 1940s, American scientist Dr. Edwin Land faced a dilemma — a question from his three-year-old daughter. After Land took a photograph of her, she asked, “why do I have to wait to see it?” This question sparked curiosity and an idea within her father and energized him to eventually create the real-time Polaroid camera. A simple question, a massive innovation.

The importance of great questions

“In the beginner’s mind there are many possibilities, but in the expert’s there are few.” (Shunryū Suzuki, Zen Monk)

As Warren Berger (questionologist) reminds us, most adults have lost the skill of question-asking. As curious children, we’re great at it. But over time, we get less comfortable with asking questions. That’s because education (and business) systems have programmed us for rote learning (e.g., taking exams) and following standardized processes. After we graduate from our insatiable early years, we become disincentivized by our surrounding institutions to ask great questions.

Being unskilled in question-asking is bad — especially in the technology world — because we and our organizations will stagnate and be usurped by hungrier, more creative entities. For most of the 1900s, organizations could bet on an idea and monetize it for decades. That’s no longer possible. Now, your game needs to be constantly refreshed, just like your iPhone. Your product or service must obviously create value for the world of tomorrow; today isn’t good enough.

As the world becomes more complex (and infinite answers are at your fingertips), the value of answers goes down, and the value of questions goes up.

Great questions lead to uncovering root challenges (opportunities), challenging assumptions, opening minds to new ideas, and igniting productive change. As Berger says, we must force our brains to “think wrong” to get to something better.

Stellar questions drive creativity and stimulate new ideas. Specifically, they’ll help you:

  • Decide: illuminate the full range of influencing variables and options in a given situation
  • Create: pry open the can of new solution options that’ll accelerate beyond the status quo
  • Connect: forge strong connections with others, showing your willingness and desire to learn, develop mutual understanding, and build rapport
  • Lead: show a balance of humility and confidence that’ll further endear you to your team and create the spark of continual reinvention (as we know, only the paranoid survive)

With AI’s rapid advancement and the “new collar” job situation forcing continual re-skilling, it’s more important than ever that we evolve our question-asking skills. After all, every good machine action is ultimately ignited by a human’s question.

How to make inquiry your thing

The conversation can be with yourself, another person, or a group. Regardless, asking great questions is a skill you must develop and keep fresh.

Start with your intent. What outcome are you seeking to achieve? Maybe it’s a new product innovation, better rapport with your team, or a sharper understanding of potential strategic pitfalls. Get very clear here so that your line of questioning truly unlocks the specific insights you’re trying to gain. The last thing you want is to be wandering off course because you weren’t clear on purpose out of the gate.

Berger advises that the tactical “how to” of great questions is a sequence of three:

  1. Why? Seek to understand (deeply)
  2. What if? Ideate and brainstorm to imagine the possibilities (nothing is off the table)
  3. How? Get practical and figure out the first few steps

Furthermore, a few specific tips for having one-one-one or small group conversations include (a) avoid closed-ended questions, (b) dig deep to learn why, © embrace silence, and (d) don’t interrupt. It’s easy to let your ego take over and spit out the thoughts in your own head. Instead, fight this temptation and follow the timeliness guidance of Dale Carnegie in his 1936 classic How to Win Friends and Influence People: be genuinely interested in other people and be a good listener.

The power of this skill is immense

Don’t write off question-asking as too “simple” a skill for today’s technology-driven world. Getting great at questioning (through continual practice) is a vital life skill that will always prove valuable to you, especially as we accelerate into the age of human-machine symbiosis. Wherever you are, drive towards a culture of inquiry — nurture the environment around you to make question-asking feel safe and normal. Ask why, what if, and how. The results will flow.

For further information, see: How to Ask Questions Better (Tim Ferriss) and The Surprising Power of Questions (HBR).

Want to stay in touch? Follow me on matthewdoan.com, LinkedIn, Twitter, and Medium.

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Matthew Doan
Design and Tech.Co

Design your 9–5 experience to reclaim time, improve your health, and be there for family. Lifestyle & Career Design | Pod: uncageyourself.fm 🎧