In 2020, I joined the Pittsburgh Pirates during one of the most challenging times for professional sports: the COVID-19 pandemic. The business side of sports was hit hard, with organizations navigating uncertainty while reimagining what success could look like during and after the crisis.

This journey was a testament to the power of leadership alignment, vision, and trust in driving sustainable change. It wasn’t about chasing quick wins—it was about intentionally rebuilding the business side of the organization with a focus on long-term growth.

Casting a Vision in Uncertain Times

When I joined the Pirates, I worked closely with President Travis Williams to cast a vision for the business side of the organization. We understood that rebuilding a professional sports organization—both culturally and operationally—was a long game.

The pandemic, while devastating, brought an unexpected opportunity: urgency. With that urgency came the chance to level-set, evaluate the business thoroughly, and redefine our goals.

• The Vision: We asked, “What kind of organization do we want to be after the rebuild?” The answer wasn’t just about financial success. It was about fostering a culture of trust, collaboration, and innovation—qualities that had been eroded over time and needed rebuilding both internally and externally. Even five years later, this remains a work in progress.

• The Patience: Casting a vision is one thing, but aligning leadership to deliver on that vision requires resilience and time. Results don’t come immediately, and it’s easy to lose faith in the process.

• The Trust: Trust wasn’t just an expectation—it was a requirement. As new leadership introduced fresh ideas and approaches, we prioritized learning the business, testing strategies, and earning trust across the organization.

The Role of Leadership Alignment

Aligning leadership is the backbone of successful change. Here’s how we approached it:

1. Strategic Discussions 💬: Leadership alignment isn’t a one-time event; it’s an ongoing process. Every quarter, we revisited our strategy to evaluate progress and adjust as needed. This helped us stay united in our vision and execution. Over time, however, the demands of the season made strategic discussions less frequent—an area where many organizations falter, often underestimating their importance.

2. Culture as the Foundation 🌐: We understood that culture could either drive or derail our efforts. We intentionally defined the culture we wanted by identifying key values, leadership behaviors, and practices to support employee engagement. This required starting from scratch—building competency frameworks, performance management tools, and other foundational systems that didn’t exist.

3. Leadership Tools and Frameworks 🔧: To empower leaders, we introduced tools like Everything DiSC Catalyst, Performance Management systems, and KPI frameworks. These tools enhanced communication, built accountability, and created clarity around expectations.

The Long Game: A Five-Year Lens

Rebuilding isn’t a sprint—it’s a marathon. From the start, we adopted a five-year lens to our planning, which allowed us to:

• Focus on Sustainable Growth: We prioritized foundational systems, such as performance management and employee engagement surveys, to monitor and refine progress over time. External factors—like playing without fans in 2020, limited capacity in 2021, and labor agreement negotiations in 2022—presented challenges, but our long-term focus helped us stay the course.

• Embrace Evolution: Culture isn’t static. Five years later, the Pirates continue to evaluate and adapt their culture to meet new challenges. What we’ve learned during difficult times is now helping us prepare for the future in an industry that’s traditionally reactive.

• Build Resilience: A shared vision and aligned leadership provided the resilience needed to navigate uncertainty. Without these, it’s easy to fall into blame, lose sight of goals, and become distracted by short-term challenges.

Key Lessons for Leaders in Sports Organizations

Reflecting on this journey, here are three lessons that remain relevant for any leader:

1. Clarity and Patience Go Hand-in-Hand: Casting a vision is just the beginning. Seeing it through requires patience, discipline, and the courage to stay the course—even when results take time. With the right systems in place to monitor progress, a disciplined approach will yield long-term success.

2. Trust Is Built in the Trenches: Difficult times test leadership teams, but they also provide opportunities to build trust. Transparency, consistent communication, and shared accountability are essential. Don’t underestimate the damage one misaligned leader can cause—open, honest, and healthy discourse is crucial for alignment.

3. Culture Requires Intentionality: Culture isn’t an abstract concept—it’s the engine that drives your strategy. Leaders must define it, measure it, and nurture it continuously. Culture is the sum of the decisions you make, the behaviors you tolerate, and the values you reinforce. Without intentionality, culture can undermine even the best strategies.

Questions to Consider 🕵️

• How aligned is your leadership team around your organization’s vision and strategy?

• Are you building a culture that supports long-term success, or reacting to short-term pressures?

• How are you monitoring and evolving your culture to stay aligned with your goals?

Let’s Start the Conversation

Rebuilding takes time, trust, and intentionality—and it’s always worth it. If your organization is navigating a challenging period or looking to align your leadership team and culture for long-term success, I’d love to connect.