At the Fortune Most Powerful Women International Summit in Riyadh, SYPartners CEO Jessica Orkin delivered a compelling message to the world’s top leaders: embrace uncertainty and lead through courageous questions. Drawing on transformative work at SYPartners, Jessica illustrated how asking the right bold question can spark innovation, reshape industries, and redefine leadership.
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Transcript

We are leading from a place beyond where we’ve been before. We’re leading in a moment where the old playbooks, the old systems, are cracking underneath us.

One of the things that my firm, SYPartners, has done for 30 years is help leaders ask bigger and bolder questions. Stepping out of previous strategies in times of transformation—times that ask more of us—from Fortune 100 companies and recognized leaders all over the world to promising startups, cultural institutions, and governments building their futures daily, what we’re finding again and again is that the most transformative leaders are those asking the most courageous questions.

They’re the questions that, by the act of asking, change the field of what’s possible. They open up possibility. They reframe what we’re seeing, and they connect people and teams around shared inquiry to create something new.

Questions are often thought of as a soft skill, but they’re not. Particularly today, in a time of transformation and uncertainty, they are a survival skill.

Let’s make this real.

Brian Chesky at Airbnb could have asked, “How do we monetize a spare room, a second house?” Instead, he asked, “What if travel was about belonging?” That question created an $85 billion business and revolutionized hospitality around the world.

After The Oprah Winfrey Show, Oprah could have asked, “What’s next for me after television?” Instead, she asked, “How can I help other people find their purpose as an expression of my own?” That question launched new platforms, new communications, and a global tour that filled arenas with people asking themselves what kind of life they wanted to live.

Working with Sephora, the question could have been, “How do we sell more makeup globally?” Instead, it became, “How could we help people around the world find beauty for themselves?” Rather than chasing a universal standard of beauty, people were empowered to define their own.

When Albert Bourla became CEO of Pfizer, he came in with a growth mandate. He could have asked, “How do we scale our most profitable products?” Instead, he challenged the organization: “What if we dedicated all of our talent, our energy, our capital to creating breakthroughs that change people’s lives?” That question transformed Pfizer from top to bottom and enabled it to deliver a COVID vaccine in eight months instead of eight years.

But finding this question is hard. Standing in uncertainty is hard. We’ve been trained as leaders to find the direction, point people toward it, and run as fast as possible.

This work requires self-reflection. It requires knowing your own purpose and the purpose of your organization—what you stand for, what your people stand for. And it requires leading through the unknown, bringing people into the exploration of the question, not just the formation of the answer.

We are all on deadline. We’re responsible for delivering results now. The clock doesn’t stop so we can reflect. This is not about asking questions to slow down. It’s about using the power of questions to lead through complexity.

We’re seeing this power not only in vision, strategy, and culture, but also in a future being co-created with AI. In our work with the Data & Trust Alliance and with CEOs and chief technology officers around the world, best practices in AI go stale very quickly. The shelf life is short.

Standards and codification matter. Alignment matters. But we’re also seeing the emergence of tools built entirely around questions to help leaders decide how and where to use AI, how to implement it, what adoption looks like, and how it’s changing their organizations.

Using questions—not answers—to lead in an operating environment that changes daily.

I’ll leave you with my question, the one that guides me as I lead SYPartners: What if the performance of organizations—my organization, your organization, even countries—was a direct function of the humanity within them?

When you step into that question, you design strategy differently. You design companies differently. You think about culture differently. That’s the question I’m in relentless pursuit of, holding space with my team and clients for what becomes possible when we design for both performance and humanity.

So I’ll leave you with this: What is your question? What’s bubbling inside you? What question is already animating how you lead today? And what more courageous question might you invite others to step into with you?
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