AI is no longer just a tool for efficiency—it is actively reshaping leadership itself. As AI integrates deeper into the workplace, leaders are faced with an evolving challenge: How do you lead when technology is continuously shifting expectations, workflows, and decision-making processes? The answer lies in adaptability. The best leaders are not those who resist change but those who develop the clarity and agility to lead through it.
In a recent Medley Moments conversation, Edith Cooper sat down with Kevin Delaney, Co-Founder of Charter, to discuss AI’s role in leadership and the evolving workplace. Delaney underscored a key reality: AI is not just a technological shift—it’s a leadership shift. The best leaders are not those who have all the answers but those who cultivate adaptability, invest in the right relationships, and build their muscle in navigating uncertainty well.
AI is transforming how leaders approach decision-making, problem-solving, and collaboration. Leaders who once relied on static expertise must now embrace a fluid, learning-oriented mindset. "AI is just a technology—it’s how you wind up using it and applying it that ultimately matters," Delaney noted in his conversation with Edith Cooper.
He pointed to examples of executives leveraging AI not just for efficiency but for personal leadership development. Dan Shipper, CEO of Every, uses AI to analyze his meeting transcripts and identify moments where he avoids conflict—an insight that allows him to refine his leadership style. Similarly, Cisco has deployed AI-assisted mediation tools to help resolve workplace conflicts in ways that traditional methods have struggled to do. Rather than relying on rigid structures or predetermined solutions, today’s leaders must cultivate adaptability, encourage continuous learning, and embrace new ways of working.
A recent McKinsey survey found that 72% of organizations are adopting AI, yet a Harvard Business Review study reveals that up to 80% of AI projects fail due to misalignment in leadership and poor strategic implementation. This highlights the critical role leaders play in ensuring AI adoption is not just a technology project but a core leadership priority.
The leaders who thrive in an AI-driven world will be those who can navigate uncertainty with confidence. Here are three strategies to build adaptability and lead effectively through change:
1. Move from Static Expertise to Continuous Learning
Leaders no longer need to have all the answers—but they must know how to ask the right questions. AI is evolving rapidly, and those who remain open to learning will be best positioned for the future. According to Forbes, adaptability has become the most in-demand skill, especially as AI-driven workplaces require leaders to pivot quickly and embrace change.
2. Strengthen Human-Centric Leadership as You Integrate AI
AI can provide valuable insights, but leadership remains a human endeavor. As AI reshapes decision-making and workplace interactions, leaders must deepen their emotional intelligence, communication skills, and ability to foster trust. "For many organizations, talent is their biggest resource, and if you leave the representatives of talent out of the conversation, you’re really handicapped in terms of what you can build with," Delaney pointed out in his conversation with Edith Cooper.
AI adoption should not come at the expense of essential leadership capabilities like coaching, relationship-building, and strategic thinking. The most effective leaders integrate AI while ensuring that empathy, adaptability, and collaboration remain at the core of leadership.
3. Foster Ethical AI Decision-Making
As AI becomes more embedded in leadership processes, ethical considerations are increasingly important. Leaders must ensure AI is used responsibly, avoiding biases and ensuring transparency in decision-making.
A proactive and structured approach is essential for implementing ethical AI decision-making. Here are some key strategies organizations are adopting:
As Delaney shared, AI is only one part of the evolving workplace. The real differentiator will be leaders who proactively develop the clarity and adaptability to lead through technological change, rather than react to it. Medley helps leaders build these capabilities—ensuring they stay ahead of change and drive meaningful impact.
Watch the full Medley Moments conversation with Kevin Delaney here.