Name: Leading On The Edge
Uploaded: 2025-05-21
Duration: 10 min 21 s

The global pandemic kicked off an era of unpredictability in business, where the only certainty is change. What does it take to lead in complex, uncertain environments where old power playbooks don’t apply? What is the best way to facilitate meaningful conversations and act with purpose? And what are the practices that enable leaders to balance short-term results with long-term organizational development? A roadmap for leadership at the edge of uncertainty and in the face of disruption.

Leading On The Edge

Conferences

Everybody, so ponder this. How would you define your leadership style? Has it evolved over the course of your career? Does it shift depending on major social movements or geopolitical events? Our next guest believes we need a playbook, a new playbook for leadership, one that requires self-awareness, clarity of values. And the willingness to embrace a future that's going to look very different from our past. Jessica Orkin is the chief executive officer of SY Partners. She has years of experience coaching leaders to ask the right questions, lead the right conversations, and move forward with purpose and moments of uncertainty. Please welcome Jessica to the stage. Good morning. I'm going to invite you on a little trip at the edge of the unknown. Because that's where all of us are leading from right now. We are leading from. We're leading from the place beyond where we've been before. We're leading on the place where the old playbooks, the old systems are cracking underneath us. Many of us are working as hard as we can to transform old systems, old ways of working, old strategies. And many of us, particularly here in this region, We are building new systems as fast as we can. But regardless, everybody here. It's responsible for leading our teams into the unknown, where certainty is rare. And where we have to rebuild the playbook. One of the things that my firm SY Partners has done for 30 years is actually help leaders ask bigger and bolder questions. So stepping out of previous strategies in times of transformation and times that ask more of us. From Fortune 100 companies, recognized, uh, leaders all over the world to really promising startups from cultural institutions to governments that are building their new, uh, their futures for their people daily. What we're finding again and again is that the most transformative leaders are those asking the most courageous questions. And these are questions that are not just about strategy. They're bigger than that. They go deeper than that. They're stra their questions, which by the act of asking, changes the field of what's possible. They open up possibility. They reframe what we're seeing, and they connect people and teams around these questions in order to create new things forward. Questions are often thought of as a soft skill. But they're not. Particularly today, particularly in such a time of transformation, such a time of unknown, they are a survival skill. Let's make this real. So Brian Chesky at Airbnb, he could have asked a question like, how do we monetize a spare room, a second house? But instead he asked the question. What if travel was about belonging? This created an $85 billion business and has revolutionized hospitality around the world. In the days 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. And this launched new platforms, new communications, and a global tour that filled arenas with people that were asking questions about the life they wanted to live. Working with Sephora, they could have asked, how do we sell more makeup globally? But instead the question became, How can we help people around the world to find beauty for themselves? So instead of chasing a universal standard of beauty, people were able to create theirs. When Albert Burla became the CEO of Pfizer, he came in with a growth mandate. He could have asked the question. How do we scale our most profitable products? But instead he challenged the organization. What if we dedicated all of our talent, our energy, our capital, In the creation of breakthroughs that change people's lives. That question transformed Pfizer top to bottom and enabled them to be the kind of organization that could deliver the COVID vaccine in 8 months instead of 8 years. But finding this question is hard. Standing in the uncertainty is hard. We have been trained as leaders. Find the direction, point our people at it, and run as fast as possible. And so this requires self-reflection. It requires knowing your own purpose, the purpose of your organization, what you stand for, what it stands for, what your people stand for. And it requires leading through that unknown, bringing people in the exploration of the question, not just the formation of the answer. And we are all, all of us here, we're on deadline. We're responsible for delivering right now results. The clock doesn't stop for us to do this. So this is not about asking questions to slow down. This is using the power of questions to lead through. Nowhere is this more true than here, than in this region. So with our work with leaders here, we are seeing change happen at an extraordinary pace. We are seeing. The WhatsApp, light up at one a.m. That's just business as usual. Because what is at stake here is a vision for generations. What is being created here matters so deeply. And even in that, even in this breathless pace. We're seeing leaders who have the biggest ambition, ask the biggest questions. The questions in this region are questions of legacy. Questions of stewardship, questions of values, questions of growth. As they take all of that energy, all of that investment, all of that talent, and the pursuit of and the creation of the future that is both honoring of heritage, but infused with new imagination. Working here is some of the most inspiring work that my firm SY partners has had the opportunity to do every day. I'm grateful for it. But we're seeing the power of questions. And the essentialness of questions not just in the setting of vision, the setting of strategy, and the creation of culture. This is even more important in a future that is being co-created with AI. In our work with the Data and Trust Alliance and working with CEOs and chief technology officers all around the world. We're all seeing the same thing. Best practices go stale very quickly in the world of AI. The shelf life is very short. And so yes, standards are really important. Codification is important. Coming together around those is important. But we're seeing the emergence of tools that are built entirely around questions to help leaders make decisions about AI, how and when to use it, how to implement, what adoption looks like, how is it changing their organizations. Using questions not answers, to lead through an operating environment that is changing daily. So, I'm going to leave you, leave you. With my question, the question that I use and that guides me as I lead SY Partners. My question is, what if the performance of organizations My organization, your organization, countries. What if the performance of organizations was a direct relationship, 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 very differently. That's the one I'm in relentless pursuit of, and I'm holding the space with my team and with my clients. So what becomes possible when we design for both performance and humanity. So I'll leave you with this. What is your question? What is the question that's bubbling up inside of you? What's the question that perhaps is already animating how you're leading your teams today? What is a more courageous question that you can invite other people to step into? Come find me after because I want to hear your question. I want to wrestle a little bit with you. Thank you.