Leadership in Times of Change: Insights from Medley's Masterminds

Why change is always hard for individuals, even when it brings clarity.

One of the most meaningful ways leaders can deepen their work and find fulfillment is by connecting with peers who understand what they face. 

This is why we created Medley Masterminds, a series of intimate, coach-led sessions that bring together senior talent leaders to reflect, connect, and grow.

Our most recent Masterminds focused on “Leading Yourself and Teams Through Change,” and it convened a powerful group of leaders from five diverse Fortune 500 companies across industries for a meaningful coaching session facilitated by an expert Medley coach on how to lead with confidence and compassion through transition.

A Space for Reflection and Shared Learning

During the session, a Medley coach guided the group through the process of pausing, reflecting and exchanging insights with peers who are experiencing similar challenges in the midst of leading teams through uncertainty and transformation. 

A key area of focus was on the emotional impact of transformation. “Change is always hard for individuals, even when it brings clarity,” one senior talent leader at a Fortune 500 Financial Services Firm said. The group explored how even if a change is positive, it can still trigger feelings of loss before leading to growth.

As leaders, it can be easy to de-prioritize our own internal worlds when so much of our work focuses on the external: managing, guiding, supporting others. But doing so is crucial for not just our wellbeing, but for our effectiveness. 

To that end, the group exchanged personal stories and practical tools, frameworks and exercises they could leverage at work to support themselves and others through change. 

Here are some of the key takeaways from the session:

1. Change is a process, not an event.


Our brains interpret change as loss, even when it’s chosen or exciting. Leaders who normalize that emotional journey help their teams move through endings, the “neutral zone,” and into new beginnings with more confidence.

2. Leading through change starts with self-awareness.


Before leaders can guide others, they have to understand their own responses to uncertainty: where we resist, where we adapt, and what helps us stay grounded.

3. Connection builds resilience.


Creating space for open dialogue and shared reflection helps teams feel anchored, seen, and supported through disruption.

The Power of Connection

At Medley, we strongly believe that the leaders responsible for developing others also deserve dedicated time and space to grow themselves.

Masterminds sessions are designed to do just that.

“It was great to meet professionals with the same areas of focus. Also, it's an interesting break in the day to reflect,” said a Masterminds participant who is a senior HR leader at a Fortune 500 financial services firm. . “The coaches are always very professional and great at facilitating the conversation.”

Medley groups offer a rare opportunity for senior talent leaders to step back, connect with peers, and reflect on the frameworks that can shape how they lead. 

Please connect with us here to learn more.

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.