Crestcom Spotlight: How Leadership Has Evolved Over 20 Years With Heather Rosenfeld

Leadership does not stand still. It changes as people change, as work changes, and as expectations evolve. In this special spotlight episode of The Leadership Habit, host Jenn DeWall speaks with Heather Rosenfeld, a Crestcom franchise owner celebrating 20 years of leadership development experience. Heather’s perspective is grounded in real-world application. Over two decades, she has worked with leaders across industries, generations, and shifting workplace norms. Her insights reveal not only how leadership has changed, but also what leaders must do to remain effective today. Meet Heather Rosenfeld Heather Rosenfeld is a Crestcom franchise owner and Area Representative serving the Massachusetts market since 2005. Originally from the United Kingdom, Heather built her early career working with diverse teams before transitioning into leadership development in the United States. In her 20 year tenure with Crestcom, she has facilitated hundreds of leadership workshops, helping leaders move from task-focused management to people-centered leadership. Heather believes leadership development is a lifelong journey — one that shapes both professional success and personal growth. How Leadership Has Changed Over the Last 20 Years Over the past two decades, leadership expectations have shifted in fundamental ways. Changes in workforce dynamics, communication norms, and employee expectations have reshaped how leaders are expected to show up every day. In this episode, Heather and Jenn discuss how the core responsibility of leadership remains the same, but how leaders achieve results has evolved significantly. From Authority-Based Leadership to Engagement Twenty years ago, leadership often relied on hierarchy and authority. Leaders gave instructions, and teams were expected to follow. Today, effective leadership looks very different. Heather explains that modern leaders must focus on engagement, collaboration, and shared purpose. Employees want to understand how their work matters and how they contribute to outcomes. Leadership has shifted from control to connection. Leadership in an Era of Constant Change Change has always existed in organizations, but the pace has accelerated dramatically. Technology, market shifts, and evolving workforce expectations mean leaders are navigating overlapping changes rather than isolated ones. Heather highlights that while change is faster, human reactions to change remain the same. Leaders must recognize resistance, provide support, and guide people through uncertainty with empathy and clarity. Managing a Multigenerational Workforce One of the biggest leadership shifts over the past 20 years is generational diversity. Leaders today may be working with up to five generations at once, each with different communication styles, motivations, and expectations. Heather emphasizes that successful leadership requires self-awareness and adaptability. There is no single leadership style that works for everyone. Leaders must learn to bring different perspectives together while fostering alignment and trust. What’s Still the Same: Leadership Is Still About People Despite advances in technology and changes in work structure, one truth remains constant: leadership is about people. Heather stresses the importance of trust, listening, and meaningful connection. Email and messaging tools may improve efficiency, but they do not replace human interaction. Trust is built through conversations, curiosity, and consistent engagement, not just transactions. 4 Leadership Lessons From 20 Years of Experience In this episode, Heather shared four clear leadership lessons she has learned over the last two decades: 1. Maintain a Teachable Attitude Leaders who thrive remain open to learning. A growth mindset allows leaders to adapt, reflect, and improve rather than resist change. 2. Listen With Intention Leadership effectiveness increases when leaders listen more than they speak. Asking questions and staying curious builds stronger relationships and better outcomes. 3. Set Clear Expectations Many leadership challenges stem from unspoken assumptions. Clear norms around communication, technology use, and collaboration reduce friction and confusion. 4. Lead the Whole Person Leadership development impacts more than performance. The skills leaders build at work influence confidence, relationships, and decision-making beyond the workplace. Continue the Conversation Leadership growth does not happen in isolation. If Heather’s perspective resonated with you and sparked reflection on how your own leadership has evolved (or needs to), this is an opportunity to keep the conversation going. Be sure to listen to the full episode to get all of Heather’s insights! You can connect with Heather Rosenfeld on LinkedIn to follow her insights, engage in leadership conversations, and learn more about the work she does supporting leaders and organizations through meaningful development. If you are exploring what leadership ...