Top Event Leadership Challenges—and How Great Leaders Overcome Them

April 29, 2025

In high-performing real estate teams, leadership is measured not by the number of tasks completed, but by the quality of conversations and connections leaders foster with new team members. Effective onboarding is more than sharing a checklist or running through CRM platforms—it’s about setting the tone, expectations, and culture that guide performance and retention. Yet, many new leaders, despite their technical competence, falter when it comes to building relational depth early in the leadership journey.

The path forward lies in adopting strategies that balance clear direction with personal connection—especially in fast-paced environments like real estate, where success hinges on collaboration, initiative, and adaptability. Leaders who ignore this balance risk creating disengaged, underperforming teams.

Setting the Tone: Shifting from Manager to Communicator

When onboarding new talent, leaders often jump straight into the “what” of the job—systems, listings, client handoffs—without addressing the “how.” But the first few conversations with a new team member are critical for long-term performance. These dialogues help establish psychological safety, clarify expectations, and foster trust.

Key foundational conversations include:

Real Estate Leadership Is a Balancing Act

Leadership in real estate demands more than transaction oversight—it requires balancing multiple priorities: company goals, team well-being, client satisfaction, and market adaptation. New leaders often struggle to reconcile directives from ownership with the day-to-day realities of their teams.

Successful leaders learn to operate as effective translators between strategy and execution. They gather input from their agents, manage upward by setting expectations with senior leadership, and find ways to preserve morale during high-pressure periods.

These leaders do not operate on autopilot—they are self-starters with the emotional intelligence to read a room, the humility to ask questions, and the confidence to make independent decisions. They serve as both visionaries and real-time problem-solvers, grounded in purpose and progress.

Building Momentum and Confidence from Within

Team members look to leaders for stability, especially during uncertain moments. Confidence—rooted in preparation, self-awareness, and ongoing learning—becomes a non-negotiable trait.

Leadership isn’t about being the loudest voice in the room or the smartest person at the table. It’s about showing up with clarity and consistency. It’s about reinforcing what matters most and helping others see where they fit into the bigger picture. Leaders who stay connected to their purpose—and help others find theirs—become the kind of leaders people want to follow.

Industry Example: Why It Matters Now

Few embody this mindset better than Sue Yannaccone, the president & CEO of Anywhere Brands (formerly Realogy Franchise Group). She has been vocal about creating environments where people feel seen, heard, and empowered—especially women and underrepresented professionals in real estate. Her leadership model centers around curiosity, clarity, and courage—qualities every new leader would do well to emulate.

To bring more depth to the conversation, other standout organizations and figures in this space include:

Leadership Is a Choice—Not a Title

Leaders in real estate have a unique opportunity to shape careers, cultures, and communities. The most successful don’t rely solely on their title to inspire loyalty. Instead, they lead through clarity, courage, and care—starting with the very first conversation.

The question for every real estate leader isn’t if they’ll face challenges—it’s whether they’re building the kind of relationships and culture that make those challenges easier to face together.