Episode 51: Quit Punting on Fourth Down: Jon Gary Herrera on Taking the Risks Public Leaders Are Trained to Avoid 

“We’ve all got to be willing not to punt on fourth down when it’s necessary, and be willing to take the criticism if it doesn’t work. You’ve got to have some thick skin and know it’s not personal, but believe in what you’re doing.” ~Jon Gary Herrera 

What happens when a public agency starts thinking like an organization that has to compete for its customers every day?

Jon Gary Herrera, President and CEO of VIA Metropolitan Transit, is challenging conventional thinking about risk, competition, and what it takes to move a public agency forward. Under his leadership, VIA has expanded its operator workforce, implemented its largest service change, and added two million annual trips.

But the bigger story is how he’s changing the way the organization operates.

In this episode of The People-Forward Leadership™ Podcast, Dr. Carol Parker Walsh explores Jon Gary’s approach to taking calculated risks, building trust with union leadership, creating transparency with his executive team, and making difficult decisions when stakeholders have competing priorities.

For leaders who have inherited established ways of operating and are ready to challenge what’s possible, this conversation offers a fresh perspective on why playing it safe isn’t always the safest decision.

Key takeaways: 

1. Recognize that public agencies have competitors, and use that awareness to improve the customer experience.

2. Build trust through transparency by giving your leadership team the same information you use to make decisions.

3. Treat union leadership as a strategic partner, not an adversary.

4. Empower your leaders to run their departments while maintaining alignment around organizational priorities.

5. Take calculated risks instead of defaulting to the safest or most familiar decision.

6. Approach AI and emerging technologies with a clear purpose tied to operational and customer needs.

About Jon Gary Herrera 

As the first Latino to lead VIA in the agency’s nearly 50-year history, President & CEO Jon Gary Herrera is guiding one of the most transformative periods in public transportation for San Antonio and Bexar County. Since joining VIA in 2017, he has helped advance major initiatives that are expanding mobility, strengthening community partnerships and preparing the region for future growth. His leadership and service have earned him numerous recognitions, including being named a 2025 South Texas Power Player and a 2025 Texas 100 honoree by The Business Journals. And while his title may be President & CEO, those who know him know his favorite role is being a connector, bringing people, ideas and opportunities together. 

Resources & Links 

• Learn more about Jon Gary Herrera: https://www.linkedin.com/in/jongaryherrera/?isSelfProfile=false  
• Learn more about VIA: https://www.viainfo.net/  
• Learn more about the People-Forward Leadership™ framework:www.thriveaxisgroup.com 
• Learn more about Recursive Leadership Theory: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=7156440  

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