Is leadership keeping up with the future of work—or just struggling to survive? As AI accelerates decision-making, remote work reshapes talent strategies, and Gen Z redefines workplace expectations, organizations face a critical turning point. In the latest Future of Work webinar, Dr. Kelly Monahan explored how leaders can adapt, innovate, and build resilient organizations in an AI-driven world
Dr. Kelly Monahan is the Managing Director of Upwork Research Institute and the co-author of the national bestseller Essential: How Distributed Teams, Generative AI, and Global Shifts Are Creating a New Human-Powered Leadership.
Webinar recording
Key Takeaways
The Workforce Challenges of Today Are Decades-old
Dr. Monahan opened the discussion by revealing a surprising historical insight—many of the concerns about talent shortages, technology overwhelming workers, and leadership gaps were already being raised in 1955. This raises an essential question:
"Why does this resemble the exact same concerns we have today? Why have we not figured this out?"
Dr. Monahan shared that her research, in collaboration with Wikistrat, explored the velocity of decision-making, AI-driven productivity pressures, and the looming risk of job displacement—all trends accelerating faster than ever before.
AI’s Impact on Leadership & Decision-Making
AI is reshaping leadership in profound ways, yet many executives remain unprepared:
Only 40% of executives know what AI skills exist within their organization.
Only 1 in 4 leaders have a workforce training program for AI adoption.
58% of global workers fear AI-driven job displacement.
"The majority of executives today are flying blind when it comes to AI development in their organization."
Dr. Monahan emphasized that AI must be leveraged not just for efficiency, but for enhancing human creativity and learning—a choice leaders must actively make.
Gen Z’s Paradigm Shift & The Growing Values Gap
A generational shift is underway, with Gen Z redefining expectations for leadership, work, and purpose:
47% of Gen Z say AI provides better career coaching than their managers.
Only half of Gen Z employees believe businesses have a positive impact on society.
Less than half of Gen Z workers see work as a core part of their identity.
This generation is values-driven but increasingly skeptical of corporate messaging.
For leaders, meeting Gen Z halfway and fostering authentic engagement is critical to retaining top talent.
Remote Work: A Strategic Advantage, Not a Liability
Despite increasing pressure from executives to return to the office, Dr. Monahan remains firm on the long-term viability of remote work:
"I am shocked we are still having this conversation. Remote work is not just about flexibility—it’s about building anti-fragile organizations that are ready for AI-driven transformation."
She warned that companies limiting themselves to local talent pools are creating fragile systems and missing out on global opportunities.
The Leadership Crisis: Moving Beyond Survival Mode
A stark reality emerged from the discussion—most leaders today are merely trying to survive:
Only 26% of leaders are focused on working differently and rethinking organizational structures.
Many leaders remain in reactive mode, struggling to keep up with AI and workforce shifts.
"How do we move beyond the fire drill, the blocking-and-tackling mindset, to actually capture the hearts and minds of people when we desperately need innovation today?"
To achieve this, leadership must shift from a transactional mindset to an essential leadership model—balancing AI, human intelligence, and long-term organizational resilience.
Conclusion: A Call for Essential Leadership
Dr. Monahan closed with a powerful call to action:
"Let this be the legacy of our time in leadership—that we were the ones who stood up for humanity in the workplace, who recognized that our greatest asset is not in our product or service, but in how we impact our people."
The session reinforced a critical need for new leadership models—ones that prioritize adaptability, human intelligence, and long-term sustainability in the face of AI-driven transformation.
Leaders must embrace AI while strengthening human creativity and decision-making.
Organizations must evolve beyond rigid, outdated models to remain competitive.
The future of leadership is not just about managing technology—it’s about shaping a more human-centric, resilient workforce.