Medley Moments: 5 Essential Leadership Skills for the AI Era

Fostering connection, belonging and trust is more important than ever.

“It can feel quite lonely in leadership right now,” James Renwick, a global executive coach, said during a recent Medley Moments conversation about effective leadership in the AI era. “Many of us [are] feeling less connected than ever before, less connected to each other as humans, perhaps less connected to our values, [and less connected] to meaningful work.”

It’s not news that leadership in 2025 is complicated. 

While AI has introduced an era of increased productivity and possibility, it has also brought uncertainty and insecurity for leaders and their teams. Learning to effectively integrate AI into work evokes strong emotions alongside real opportunities, and leaders face pressure not just to navigate this transition themselves, but to guide their teams through it.

At Medley, we believe the best answers come from learning together, which is why we brought together Medley co-founders Edith Cooper and Jordan Taylor with two coaches from our network — Archana Bharathan and James Renwick — to explore what strong leadership requires in this moment. 

Here are five essential elements of effective leadership in the age of AI that we landed on during the conversation.

Design for Both Efficiency and Belonging

The best leaders recognize that AI integration isn't just a technology challenge. Rather, it's a human one. Optimizing for productivity alone will fail if people don't feel connected to their work and each other.

"The best leaders in many ways, they may design for both efficiency of the system and also belonging [to its] humans," Archana says. "So, you know, go right ahead. Let the AI do the heavy lifting on all of the tasks. Invest more deliberately in the rituals, in the conversations, in the shared meaning-making that we as a community of humans can provide."

This requires a fundamental shift in priorities. While AI handles coordination and execution, leaders must double down on what makes teams human: the conversations that build trust, the rituals that create culture, and the shared experiences that give work meaning.

Learn Alongside Your Teams

Strong leaders embrace the reality of how fast AI is moving, and that no one has all the answers. They then turn the ambiguity into an opportunity to learn alongside their teams. As Archana advises:

"Demystify AI, show teams, demonstrate, do it with them so it's not just something that you're delegating, but in many ways get hands on with them as to what AI and specifically what agentic AI can do and cannot do." 

This shared learning serves multiple purposes. It builds capability across the team, and it creates psychological safety. When leaders admit they're learning too, it gives everyone permission to not have it all figured out. And critically, it surfaces insights that leaders might miss on their own.

One tactic Archana offers is to create "safe to fail pilots." These are low-pressure experiments where teams can explore AI together to allow for collective learning. Examples could include vibe coding labs and other safe spaces where teams can figure out how to practice using and experimenting with AI without pressure. 

Create Space for Difficult Emotions

AI anxiety is real, and it can show up as fear, confusion, and uncertainty about purpose and status. Strong, empathetic leadership involves making room for these feelings that arise in your team, as well as in yourself as a leader. As Archana says:

"First, name the emotion. Is it anxiety, stress, fear, or if it's feeling threatened, name it … And once there is that space for people to name their feelings without leaders [needing to] rush in to reassure with facts, then we can start to put things into a framework.”

This isn't about dwelling in negativity. It's about acknowledging reality before moving forward. As James describes, many leaders feel isolated in their concerns: "There's often an assumption that everyone else is ahead of the curve." When leaders create spaces for people to share their lived experience, "they're able just to let their guard down and to share their concerns or fears or excitement around this topic, and to feel validated perhaps that they're not as far behind the curve as they thought they were."

For leaders, James emphasizes the importance of managing your own response to perceived threats: "Whether [a threat] is perceived or real, our body responds in exactly the same way." He recommends both physical techniques (breathing, posture, slowing down) and conscious shifts toward curiosity by saying, “How fascinating, what can I learn from this?"

Seek Challenge, Not Just Confirmation

Here's an uncomfortable truth: some leaders are finding their interactions with AI more satisfying than conversations with their teams. AI doesn't push back. It refines your thinking based on your prompts. It feels productive and frictionless.

But as Edith warns, this comfort can be dangerous for leaders: "[AI offers] a reflection of their thinking. It's a reflection of their bar, of what excellence looks like."

What makes organizations extraordinary isn't consensus. Rather, it's inviting productive friction. 

"[Production friction] is the person in the room who looks at you and says, but wait a minute. You know, I don't agree with you … I'm not sure that these tools are really built to say I don't agree with you, and I'm gonna debate that."

Strong leaders actively seek out these moments of disagreement. They ask themselves, as Edith suggests, “How would your team be more effective if you spent the same amount of time going back and forth and debating?"

This means resisting the AI comfort trap and instead investing in the messy, sometimes frustrating work of human deliberation. It means valuing the team member who challenges your assumptions as much as the tool that executes your vision.

Get Comfortable Being Uncomfortable Together

Perhaps the most important leadership capability for the AI era is the ability to sit with uncertainty, and to bring others along in that discomfort. As Edith says:

"We're all a little bit uncomfortable here because the pace of change and the potential impact of AI is an uncomfortable place. But here's the interesting thing. I think it's an opportunity for all of us to get comfortable together being uncomfortable."

This shared uncertainty creates new forms of connection. It breaks down the traditional hierarchy where leaders have all the answers and everyone else executes. It requires more connectivity between leadership and the people doing day-to-day work.

James frames this as "waking up to our power. The humanness of all we do has never been more important and creating deeply human experiences."

The uncertainty isn't going away. AI will keep evolving. Work will keep changing. Strong leaders don't pretend to have certainty they don't possess. Instead, they build teams that can learn, adapt, and stay connected through continuous transformation.

Click here to watch the full Medley Moments conversation with our Medley co-founders and coaches.

Below are additional resources for leaders navigating this age of AI:

About Medley:


Medley is a leadership development company that brings people together in small, facilitated groups to grow through shared reflection, learning, and accountability. We believe that leadership is not a title but a practice, and that people learn best in community with others who offer diverse perspectives and experiences. Through our programs, members build greater self-awareness, develop key leadership skills, and cultivate meaningful connections that support both professional and personal growth.

Please connect with us here to learn how to bring Medley into your organization