Strategic Syncing

On his first day as Director of Technology Innovation and Integration at Arlington ISD, Steve Simpson made a decision most leaders wouldn't: he moved out of his closed-door office and into a cubicle with the rest of his team.James Symons sits down with Steve to unpack the leadership philosophy behind that move, and what it's taught him about leading instructional technology across 54,000 students and 74 campuses through one of the most turbulent decades in K12 EdTech.Steve shares why flat hierarchy and high autonomy aren't the same as "no accountability," how he's built credibility by listening more than talking, and why being "on the periphery" of a district's core priorities can actually be a strategic advantage.The conversation also digs into the post-COVID EdTech backlash, the beautifully designed framework Arlington had to leave behind, and why digital literacy is finally being written into the district's strategic plan for the first time ever.In this episode:• Why he gave up his office on day one• Flat hierarchy with clear boundaries, the operating model• Autonomy vs. accountability, and why they're not opposites• The post-COVID EdTech backlash no one wants to talk about• Speaking with intention, not volume• Why "the periphery" is a leadership advantageA thoughtful, no-nonsense conversation for IT leaders, district administrators, and anyone navigating the messy middle between technology strategy and the people they lead.🎧 Follow the Strategic Thinking Podcast for more candid conversations with K12 and IT leaders.

How do you lead technology for 100,000+ students across 127 campuses, without becoming the bottleneck, the bureaucrat, or the burnout?This week, host James Symons sits down with Kris Trejo, Assistant Superintendent for Technology Services (CTO) at Northside Independent School District, the 4th largest school district in Texas.From a textbook warehouse to the C-suite over 27 years and 8 promotions, Kris shares the leadership philosophy that's carried him to the top of one of the country's largest K-12 tech organisations. He opens up about building a "work toward a yes" culture, why he believes it's his job to make himself replaceable, and how he leads with steadiness in the most challenging political and budgetary climate public education has faced in decades.In this episode:What an Assistant Superintendent really doesHow to avoid bureaucracy in a leadership group of 30+The "work toward a yes" philosophy that flips traditional IT cultureHiring for growth potential, not pedigreeLeading through pressure: "Public education is under assault"Why emotional intelligence matters more than ever at scale"Real life starts at 5:00", protecting the humanity of your teamA masterclass in leading at scale without losing the human in the work.

Dustin Harden runs technology for Clear Creek ISD, a Texas district where NASA engineers sit on the school board, students earn National Merit honors, and 12-year-olds team up on Discord to outsmart the district's filters.In this episode, Dustin joins James for a candid conversation about leadership, ego, and growing up inside the CTO role. He landed his first director job at 26, beating a candidate with a doctorate in education, and spent years unlearning the "smartest guy in the room" instinct that came with it.We talk about the summer his team finally told him to slow down, why students who hack the filters often end up as future employees, what ed-tech vendors actually need to do to earn a district's trust, and why K-12 CTOs across Texas share openly with each other instead of competing.An honest, grounded look at modern educational technology leadership, what it takes, what it costs, and why the best leaders eventually stop trying to be the smartest person in the room.Topics: K-12 leadership, ed-tech, servant leadership, vendor relationships, innovation under budget constraints, district collaboration, growing through ego.

What does it really mean to lead technology in a district of 33,000 students across 35 campuses?Cara Carter is the CTO of Northwest ISD in Texas, one of the fastest growing districts in the DFW Metroplex. She started as a classroom teacher and has spent 20 years building something remarkable: a technology culture that is deeply human.In this episode, Cara unpacks what it actually takes to lead at scale — building a cyber-aware culture from the ground up, stepping into AI before the roadmap is clear, and making hard decisions when the people you care about don't yet understand why.This one goes beyond strategy. Cara talks about the emotional weight of leadership, being misunderstood, letting people see your heart, and the quiet confidence that only comes with time.In this episode:Why K12 is the most targeted industry for cyber attacks, and how Cara built a culture of caution across non-technical staffStepping into AI early, intentionally, and without all the answersThe leadership lesson that only time can teach youWhat it costs to lead people you deeply care about🎧 Listen on your favourite platform:🟢 Youtube🎙️ Apple Podcasts 📦 Amazon Music 📲 Follow the conversation:Instagram → @stratgicsyncingLinkedIn → Strategic Syncing

What does it really mean to lead technology in a district of 33,000 students across 35 campuses?Cara Carter is the CTO of Northwest ISD in Texas, one of the fastest growing districts in the DFW Metroplex. She started as a classroom teacher and has spent 20 years building something remarkable: a technology culture that is deeply human.In this episode, Cara unpacks what it actually takes to lead at scale — building a cyber-aware culture from the ground up, stepping into AI before the roadmap is clear, and making hard decisions when the people you care about don't yet understand why.This one goes beyond strategy. Cara talks about the emotional weight of leadership, being misunderstood, letting people see your heart, and the quiet confidence that only comes with time.In this episode:Why K12 is the most targeted industry for cyber attacks, and how Cara built a culture of caution across non-technical staffStepping into AI early, intentionally, and without all the answersThe leadership lesson that only time can teach youWhat it costs to lead people you deeply care about🎧 Listen on your favourite platform:🟢 Youtube🎙️ Apple Podcasts 📦 Amazon Music 📲 Follow the conversation:Instagram → @stratgicsyncingLinkedIn → Strategic Syncing

What does real IT leadership actually look like?In this episode of Strategic Syncing, James sits down with Dr. David Benjamin Weems — a former petroleum engineer turned CTO — who transformed one of the most remote school districts in West Texas.From rebuilding infrastructure and connectivity to solving real-world challenges in education, this conversation goes beyond technology, into leadership, people, and impact.💡 In this episode:The transition from engineering to education leadershipWhat it takes to scale technology in real environmentsWhy leadership matters more than toolsThe reality of operating in remote and underserved communitiesConfidence vs competency in leadershipThis is a candid conversation for IT executives, operators, and anyone building systems that actually need to work in the real world.

What does real IT leadership actually look like?In this episode of Strategic Syncing, James sits down with Dr. David Benjamin Weems, a former petroleum engineer turned CTO, who transformed one of the most remote school districts in West Texas.From rebuilding infrastructure and connectivity to solving real-world challenges in education, this conversation goes beyond technology, into leadership, people, and impact.💡 In this episode:The transition from engineering to education leadershipWhat it takes to scale technology in real environmentsWhy leadership matters more than toolsThe reality of operating in remote and underserved communitiesConfidence vs competency in leadershipThis is a candid conversation for IT executives, operators, and anyone building systems that actually need to work in the real world.

In this episode of Strategic Syncing, we speak with Dr. Chad Jones, Executive Director of Technology at Lamar Consolidated ISD.Managing technology for nearly 50,000 students and 70,000+ devices, Chad shares what it really takes to make IT work in high-growth environments.We talk about:• Why consistency beats quick fixes• Leading through pressure when systems fail• Building a team culture based on professionalism, respect, and kindness• The responsibility leaders feel when technology doesn’t workBecause in reality, IT isn’t just about systems.It’s about people.

In this episode of Strategic Syncing, we speak with Dr. Chad Jones, Executive Director of Technology at Lamar Consolidated ISD.Managing technology for nearly 50,000 students and 70,000+ devices, Chad shares what it really takes to make IT work in high-growth environments.We talk about:• Why consistency beats quick fixes• Leading through pressure when systems fail• Building a team culture based on professionalism, respect, and kindness• The responsibility leaders feel when technology doesn’t workBecause in reality, IT isn’t just about systems.It’s about people.

Most IT challenges don’t start with technology.They start with people, workflows, and unclear ownership.In this first episode of the Strategic Syncing Podcast, James sits down with Aaron Alonzo, Executive Director of Technology at San Antonio Independent School District, the same district where he grew up and began his career.Aaron’s journey into technology leadership didn’t start in IT.It started as a PE assistant coach, wearing shorts and a whistle, before eventually moving into the computer lab and becoming the unofficial IT problem solver.Seventeen years later, he now leads technology strategy for the district.In this conversation, we explore:• Aaron’s journey from substitute teacher to IT executive• What servant leadership looks like in real organisations• Why informal conversations with your team matter more than leaders think• How school districts manage technology with limited budgets• The student repair team initiative helping students gain real-world experience while supporting district technologyThis episode is a grounded conversation about leadership, community, and the reality of running technology inside complex organisations.Listen and connect:Website⁠https://www.strategicsyncing.com/⁠Watch the full episode on YouTube⁠https://youtu.be/agrCGBv4g30⁠Follow Strategic Syncing!Instagram: ⁠https://www.instagram.com/strategicsyncing/⁠LinkedIn: ⁠linkedin.com/company/strategic-syncing/

Most IT challenges don’t start with technology.They start with people, workflows, and unclear ownership.In this first episode of the Strategic Syncing Podcast, James sits down with Aaron Alonzo, Executive Director of Technology at San Antonio Independent School District, the same district where he grew up and began his career.Aaron’s journey into technology leadership didn’t start in IT.It started as a PE assistant coach, wearing shorts and a whistle, before eventually moving into the computer lab and becoming the unofficial IT problem solver.Seventeen years later, he now leads technology strategy for the district.In this conversation, we explore:• Aaron’s journey from substitute teacher to IT executive• What servant leadership looks like in real organisations• Why informal conversations with your team matter more than leaders think• How school districts manage technology with limited budgets• The student repair team initiative helping students gain real-world experience while supporting district technologyThis episode is a grounded conversation about leadership, community, and the reality of running technology inside complex organisations.Listen and connect:Websitehttps://www.strategicsyncing.com/Watch the full episode on YouTubehttps://youtu.be/agrCGBv4g30Follow Strategic Syncing!Instagram: https://www.instagram.com/strategicsyncing/LinkedIn: linkedin.com/company/strategic-syncing/