2025 Ones to Watch - Industry Leaders: John Halsey, Cummings Properties

“John is a standout leader whose impact is both measurable and lasting. In just seven years, he rose from an entry-level position to become the youngest member of Cummings’ 11-person executive leadership team, where he plays a key role in shaping company policy and guiding business development. His rapid ascent reflects his deep industry insight, strategic mindset, and results-driven leadership.”

What recent accomplishment or initiative are you most proud of, and what impact did it have on your firm, clients, or community? The leasing department plays a key role in advancing Cummings’ “All Profits to Nonprofits” model, through which 100% of rental profits support charitable organizations. We’re responsible for new business development across 10 of the firm’s 11 communities, and have maintained occupancy levels that consistently outperform the broader market – averaging 92.6% for the fiscal year ending June 2025. This steady performance reflects a shared commitment to client service and community impact. By continually welcoming businesses to the portfolio, our team helps ensure funding for hundreds of nonprofits.

How do you inspire, motivate, or mentor others within your organization? My leadership style is grounded in collaboration and shared growth. By setting clear expectations and supporting professional development, I encourage the team to build on individual strengths while contributing to collective goals. Involving team members in strategic planning and decision-making leverages their diverse perspectives and expertise, fostering both ownership and engagement. This approach has helped cultivate a cohesive, high-performing department, recognized for strong retention and consistent productivity.

What is one major challenge you’ve overcome as a leader, and what did it teach you? Joining Cummings without real estate experience presented a steep learning curve. My journey from entry-level property manager to leader of the Leasing Department within four years was accomplished through focus, persistence, and collaboration, and it highlighted the power of collective effort. In leading a team of five – each with more industry experience than me – I aimed to foster mutual trust, respect, and open communication. I welcomed guidance, drew on the team’s strengths, and tried to maintain a balance of confidence and humility. Together, the team built a strong, results-driven culture.

What advice would you share with emerging professionals striving to become future leaders in commercial real estate? The most important foundation is a combination of curiosity, adaptability, and relationship-building. Seek to understand all aspects of the business, from operations to finance to tenant relations, and be open to learning from colleagues at every level. Developing strong communication skills and fostering trust with clients, peers, and teams is equally critical. Finally, embrace challenges as opportunities for growth – leaders are defined not just by results but by the ability to guide others, make thoughtful decisions under pressure, and create environments where teams can succeed together.

What daily habit or routine helps you stay focused or motivated as a leader? Daily time with family provides perspective and grounding that carries into every other part of life.