Aligning Culture and Capability: Smarter Systems for Sustainable Leadership with Matthew Person

In this insightful episode, Michael D. Levitt explores the Square Management System Alignment Model, a framework by Matthew Person designed to foster organizational alignment without the need for micromanagement. Developed by Matthew from Town Square Advisors, this model is grounded in real-world executive and M&A experience. It focuses on aligning employee beliefs and behaviors with company systems to prevent culture drift and enable long-term, sustainable growth. Michael underscored the urgent need for such systems, sharing examples of organizations that significantly improved through alignment—not turnover—by earning employee trust and recognizing internal capability.

The Power of “Constrained Independence”

Matthew introduced the concept of constrained independence, a four-part management model built on Identity, Instruction, Intercommunication, and Information, with ten key operational elements. This framework helps leaders strike a balance between empowering staff and maintaining clarity. Listeners were invited to assess their own organizations using a free quiz at TownSquareAdvisors.com. Michael emphasized the importance of continuous monitoring and cultural measurement—warning that top-down approaches to diversity and alignment can sometimes lead to unintended tension unless rooted in authenticity and openness.

Lessons from Championship Teams

Drawing from professional sports, Michael shared a compelling analogy about leadership, team culture, and performance. While the 1990s New York Yankees focused on acquiring high-priced talent, it was the Boston Red Sox's commitment to balanced teams and deep culture, under leaders like Tito Francona, that ultimately led to their championships. The lesson? A deep bench, clear roles, and trust in your team’s abilities drive real, repeatable success.

Trust, Decision-Making, and Human-Centered Leadership

Trust emerged as a recurring theme—especially in how it empowers independent decision-making and employee engagement. Matthew contrasted toxic, high-constraint workplaces with cultures that reward initiative. Michael reflected on his own experience of being hired for his potential, not just his résumé, and how adaptable systems that honor both organizational needs and individual strengths pave the way for high-performance cultures.

Hiring, Retention, and Thriving Work Environments

With over 18 years of leadership experience, Michael emphasized the importance of cultivating an environment where employees can grow, not just work. Culture isn’t one-size-fits-all—it’s about designing systems and environments where your people can thrive. He challenged the myth of a “correct culture,” advocating instead for cultural authenticity and values-based alignment tailored to each organization.

Ethical Offboarding and Supporting Career Growth

When it comes to letting people go, Michael shared his values-driven approach: treat exits with dignity, and support people in finding better fits elsewhere. Drawing on personal experiences from both sides of the table, he emphasized the long-term value of trust, transparency, and doing what’s best for the individual, even when it's a tough call.

Culture Meets Data: Using Analytics to Lead Smarter

To round out the discussion, Matthew dove into how the Square Management System uses analytics to assess culture across various organizational levels. This diagnostic tool is especially helpful for startups and mission-driven entrepreneurs aiming to build cohesive teams from the start. The system doesn’t promise perfection, but it delivers clarity—giving leaders the actionable insights they need to close culture gaps, improve communication, and align operations with purpose. Listeners are encouraged to explore the free tools and resources at TownSquare-Advisors.com.

 

Welcome to another episode of the Breakfast Leadership Show, where we dive deep with leaders reshaping how we work, lead, and live. Today’s guest is Matt Person—a strategic powerhouse with more than two decades of experience in M&A, organizational design, and aligning people with purpose.

Matt is the mind behind the Square Management System, a practical framework that brings clarity and cohesion to companies' operations by aligning people, processes, and performance. His upcoming book, The Culture of Alignment, explores this in depth and is a must-read for leaders building resilient, high-performing organizations.

With a career that spans global corporate development, private equity-backed ventures, and even a decade in professional baseball leadership, Matt brings a truly unique perspective. Recognized as a Rising Star by the Colorado Springs Business Journal and a Thought Leader of the Year finalist by the Alliance of M&A Advisors, his credentials are only matched by his passion for excellence.

Matt holds an MBA and an MS in Finance from Boston College, and a degree from Colgate University. He’s a guest lecturer, frequent industry speaker, and lives just outside Boston with his family—when he’s not refining growth strategies, you’ll find him on the golf course, hunting down vintage cars, or scouting out his next favorite restaurant.

Speaker Bio:  https://www.espeakers.com/dashboard/50932/profile

LinkedIn:  https://www.linkedin.com/in/matthewdperson/

Website:  https://www.townsquare-advisors.com/