Photo courtesy of SYPartners

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How Deep Listening Can Help You Be More Creative

Photo courtesy of SYPartners
How Deep Listening Can Help You Be More Creative
Published April 3, 2019 by The 99U Team

When we set the theme for our 2019 conference — The Creative Future — we imagined a future where creative skills are more pervasive and prized, and how that might reshape the world around us. As we prepare for the event in May, we’re asking our speakers to share a skill they think is important for all creatives to navigate what’s to come.


Jessica Orkin is the President of SYPartners, a consultancy that helps organizations transform into more vibrant versions of themselves. Jessica will be at the 11th Annual 99U Conference taking place May 8-10 in New York City.

Q. What is a skill you believe to be futureproof?

A. To navigate the edge of the unknown, both with Fortune 500 companies and with my SYPartners team, I have cultivated a practice of deep listening—an intentional quieting of the ego and the desire to apply past patterns or jump to solutions. The result is an openness to a much richer, less obvious world of information: the energy of a room, the connections between people, the things unsaid, the voices missing in a conversation, ideas that jolt and jar rather than fit in. From that place of deep listening, I start to sense what lies beneath the surface of things, and often a different understanding of the “problem” emerges, giving rise to radically different ways forward.

Q. Why will deep listening be so important in the future?

A. Design thinking has inspired many people, particularly those who don’t self-conceive as “creatives,” to recognize their creativity and generate ideas at high volume and velocity. I think of this as the "creative exhale"—emitting ideas into the world. But as more interconnected, complex human challenges and opportunities emerge we will all need to get better at the “creative inhale”—attending to the information we take in, the signals of the future we are sensing, the voices and perspectives that may be missing, and how we define the problems we solve. Listening deeply and differently changes our creative exhale, enabling us to generate fundamentally new solutions.

Q. Has there been a time in your career when you saw the power of the creative inhale?

A. In my work with companies, I’ve seen inspiration happen when leaders seek out new perspectives and focus on their creative inhale before jumping into the exhale.

For instance: What does a luxe Danny Meyer restaurant and your local CVS have in common?

They are both pursuing purpose-driven service and hospitality. CVS executives saw this firsthand on a recent visit to Manhattan. SYPartners had organized a tour of hospitality experiences to inspire new thinking about customer-centricity. It would have been easy for the pharmacy leaders to dismiss the restaurant’s extra-mile hospitality as irrelevant to CVS. But they didn’t. By leading with curiosity and suspending skepticism—in other words, practicing deep listening—they came away with insights that are changing how they think about their culture, not just their approach to service.

Q. How do you get better at deep listening?

A. I took a fairly radical approach—three years ago, I became a student of sound meditation with Sara Auster to learn about the science and practice of deep listening. This led to some wild adventures (ask me about studying raga in India for 10 hours a day, with no musical background). This path is decidedly not for everyone. Some easier ways in:

  1. Pursue curiosity. Ivy Ross, head of design for Google Hardware, once told me, “I pay attention to what gets my attention.” That awareness has taken her on intellectual and creative adventures that led to new products and paradigms.
  2. In the beginning of a new project, cultivate the art of the beautiful question. Observe how leading with questions instead of answers changes your understanding of the problem you are seeking to solve.
  3. Wake up your senses. Move your body, go to a museum, attend a sound bath. Do anything that gets you out of your head for a while and activates all the other ways you take in information.
  4. Meditate. If nothing else, it will quiet your ego and help you hear others in ways that creates room for new possibilities to emerge. I recently meditated for 20 minutes in a hallway before going in to meet with former President Obama so that I could listen as deeply as possible instead of trying to get my point across or, worse, trying to impress. It worked. Mostly.
  5. When creating, be aware of the mode you are in—inhale or exhale. Ask yourself if you have given enough time or space for the inhale. Do you have enough rich data? Have you sat with it long enough? Have you gotten under the skin of things?
  6. Conversely, don’t get stuck in listening mode. Convert insights early and often into thoughtful action. Take a prototyping step forward and then observe its effects. Listen and make…inhale and creative exhale… repeat. It’s the interplay of these modes that gets to somewhere interesting.


Hear from Jessica and other creatives shaping the future at the 11th Annual 99U Conference, May 8-10, 2019 in New York City.

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