Municipal Leaders: Develop Faster, Lead Stronger, Build Better
Every week, you’ll get insights and actionable steps to help you navigate personal growth and professional success.
Episode 264 of The HaltingWinter Podcast
Brought to you by Tyler Technologies
When cities talk about homelessness, the conversation usually turns toward capacity, compassion, and cost. But very few leaders talk about navigation—how impossible it is for someone without ID, transportation, or support to move through a maze of agencies, forms, and requirements that even seasoned professionals struggle to understand.
And that’s exactly where this week’s guest shines.
Daniel McDonald spent more than two decades with the Tampa Police Department. But his most important contribution didn’t come from patrol, SWAT, or special operations. It came the day his chief handed him an undefined assignment with no staff, no budget, and no blueprint:
“Rethink how we respond to homelessness.”
That single directive reshaped Daniel’s entire career and ultimately reshaped Tampa’s strategy.
His approach didn’t rely on new ordinances or harsher enforcement. It relied on something far more disruptive:
Trust. Creativity. Patience. And a willingness to stop solving symptoms and start solving systems.
Daniel became Tampa’s first homeless liaison officer, building relationships with providers, cutting through bureaucratic barriers, and helping individuals replace IDs, secure documents, and access services that had always been out of reach. Instead of relying on repeat arrests—the expensive revolving door he calls “the world’s most costly homeless shelter”—he built pathways that led people out of crisis and into stability.
For local government leaders, his story is a blueprint for what happens when you spot talent inside your organization, elevate it, and give it room to innovate. It’s also a reminder that homelessness cannot be addressed by any one department or nonprofit alone. The work requires alignment, coordination, and someone who sees both the human need and the systems that trap people in place.
Daniel’s work is a model for small towns and major cities alike and a challenge to rethink what’s possible inside your own organization.
Connect with Daniel and his organization, Homeless Innovations HERE –>
Listen to Episode 264: Rethinking Policing, Rebuilding Lives
Available now on Apple Podcasts, Spotify, and wherever you listen or at HaltingWinter.com/resources.
This episode is sponsored by Tyler Technologies, the leader in empowering the public sector with software solutions that connect data, streamline operations, and improve service delivery. From civic services to public safety, Tyler helps local governments build stronger, more resilient communities.
Learn more at tylertech.com/winter →
The MLDC is where local government leaders go to grow, together. It’s the fastest-growing leadership development community designed specifically for the public sector, now paired with a comprehensive 9-month Leadership & Culture Program for those ready to elevate their organization.
Members receive weekly leadership content, access to our daily podcast, monthly virtual trainings, and a clear roadmap for building a culture that reduces burnout, strengthens retention, and drives meaningful impact in every department.
If you’re committed to leading well and shaping a healthier culture for your team, now is the time to save your seat for the 2026 cohort.
Learn more at haltingwinter.com/mldc →
The HaltingWinter Podcast celebrates and elevates the people who power local government. Through in-depth conversations with leaders from cities, counties, and communities of all sizes, host Seth Winterhalter explores the journeys, challenges, and innovations happening in municipal leadership across America.
