What does great leadership really leave behind?

In this episode of the Strategic Syncing Podcast, James Symons sits down with Dr. Chad Stevens for a candid conversation about leadership, technology, confidence, and the realities facing education today.

Drawing on 30 years in education and leadership roles across CDW, AWS, and now ClassDojo, Chad shares his perspective on navigating change, leading through uncertainty, and staying focused on what creates real value for schools and their communities.

The conversation also gets personal. Chad opens up about self-confidence, slowing down, learning to be yourself, and why some of life’s biggest challenges can ultimately give us lift.

They explore what it means to build resilient organisations, why technology still needs human connection, and the legacy great leaders leave behind: the leaders they help develop.

A thoughtful conversation about technology, leadership, and becoming more comfortable with who you are.

EPISODE TIMESTAMPS

00:00 Welcome to the Strategic Thinking Podcast
00:55 Meet Dr. Chad Stevens
02:28 ClassDojo and a Different Approach to EdTech
06:05 Why You Can’t Mandate Engagement
07:31 Doing More With Less in Education
10:11 Innovation During Challenging Times
13:09 What Happens When Schools Can’t Invest in Technology?
16:32 Proving That Technology Actually Works
17:40 Building Resilient Businesses Through Uncertainty
21:56 Why the EdTech Industry Needs to Work Together
24:14 From Technology to Life and Leadership
26:15 How Failure Can Give Us Lift
28:29 What Great Leaders Really Leave Behind
30:39 Why Leaders Need Time to Slow Down and Reflect
35:58 What Does Success Really Look Like?
38:32 Leadership and the Struggle With Self-Confidence
40:52 Building Confidence Through Vulnerability
41:44 The Power of Being Yourself
42:45 Closing Thoughts

Atlanta Public Schools serves 50,000 students across 80+ campuses. Natasha Rachell leads instructional technology for all of it, with a team that's shrunk from 39 people to 13.Her district is currently proposing screen time limits: minute caps for elementary, percentage caps for secondary. As Director of Instructional Technology, she understands why. Personally, she thinks we're asking the wrong question.In this conversation with James Symons, Natasha makes the case that "screen time" is a bucket we've thrown everything into, a student building a portfolio and a kid scrolling alone in their bedroom counted as the same thing. She argues the panic is adults projecting their own fear onto children who don't learn the way we did.She also talks about doing more with half the staff, why she hasn't let anything go (and why that might be a problem), and how her twin brother's traumatic brain injury reshaped how she thinks about accessibility and leadership.

Chapters:
(00:00) Intro
(00:55) Where "undeniable impact" came from
(03:37) Running a 50,000-student district with 13 people
(05:54) What had to give
(07:44) Jamaica to England to Toronto to Atlanta
(09:35) "I see something in you"
(10:37) Screen time: the research argument
(13:16) "Our fear is being projected onto our kids"
(17:28) All screen time is not equal
(19:20) Where parents come in
(20:05) Her brother's brain injury
(23:14) How that changed her leadership
(25:02) Technology and accessibility
(26:55) What excites her about leading people
(32:25) The 360 review
(36:03) "Stop coming up with so many ideas"

Natasha Rachell is Director of Instructional Technology at Atlanta Public Schools.

Teachers use AI to build the lesson. Teachers use AI to grade the lesson. Students use AI, and it's cheating.Maurice Dragon, CIO of Orange County Public Schools, thinks the AI cheating conversation in K-12 has almost nothing to do with students. The same assignment can earn an A+ in first period and a zero in second. The work didn't change, the adult reading it did.James Symons opens by asking whether AI is going to destroy our children. What follows is a conversation about what AI actually threatens in education: productive struggle, the processes we've assumed were the point, and which of those are still worth protecting.Maurice also traces his path from teaching first grade in Florida, burning 300 alphabet DVDs one weekend because only one student in his class had a computer at home, to leading technology for one of the largest districts in the country. And he makes the case that AI implemented well will increase human connection in classrooms, not reduce it.(00:00) Welcome to the messy middle

(00:56) "Is AI going to destroy our children?"

(01:36) What AI takes away: productive struggle

(01:58) The Dark Ages, and why we stop valuing skills

(07:10) Where has education focused on the wrong things?

(08:54) Math at a scale humans can't reach alone

(13:18) What's too simple to hand to AI?

(13:32) A+ in one class, cheating in the next

(23:47) What Maurice is most optimistic about

(24:43) Why human connection increases, not decreases

(26:41) The workload teachers carry after hours

(28:12) The mixed message schools send students

(30:31) 40 math problems and the point of practice

(31:20) First grade teacher to district CIO

(32:41) Burning 300 DVDs for kids without computers

(36:44) The juice bottle: leading humans first

(41:37) What first grade teaching and the CIO role share

(43:32) What Maurice's team would tell him to work on

(47:14) When people stop emailing you

(49:46) Closing thoughtsGuest: Maurice Dragon, Chief Information Officer, Orange County Public SchoolsHost: James SymonsWatch the full conversation on YouTube: https://youtu.be/8c9kOv3gskw

Lacey Merrifield is the Technology Director at Bosqueville ISD, a K-12 district of around 750 students near Waco, Texas. Her team is two people. Between them: 1,300 Chromebooks, 165 Microsoft devices, 60 iPads, the website, the social accounts, and the printers when they go down.

She talks with James Symons about leading from the front lines, the app rollout that took two years to admit was wrong, what she did differently the second time, and why handing someone the reins and staying hands off is the hardest thing she's learned as a leader.

Also: teaching seventh grade science on twelve hours' notice, and why summer is the busiest season in school IT.

Follow Strategic Syncing on Spotify so you don't miss an episode, new conversations with K-12 leaders every other Monday.

Watch the full conversation on YouTube: https://youtu.be/sKd_IIzrPNI

(00:00) Intro
(01:23) Two people, 750 students, 1,300 devices
(02:46) Back in the classroom on twelve hours' notice
(06:51) How COVID pulled her into technology
(08:00) Full-time job, night classes, online teaching
(14:38) Finding tools when you have no time to find tools
(17:02) "I'm actually his boss, but that's not how I treat him"
(20:44) The app rollout that went wrong
(23:42) What failure actually feels like
(25:41) Perfectionism as an obstruction
(30:38) Close

What keeps an entire industry moving when literally no one is in charge?

No single boss. No central conductor. Thousands of strangers, across different countries and languages, and somehow, every single day, it works.

Todd Chapman spent 30 years inside aviation, leading over 1,000 people across 39 airports at Jetstar and running operations at Qantas through COVID. Now, as founder of Leading Edge consultancy, he pulls back the curtain on the invisible machine behind every flight.

But this isn't really about planes. It's about what makes any organisation hold together when you can't watch everyone: why culture can't be laminated onto a wall, why "feedback is a gift," and why the best teams make the right call whether the boss is in the room or not. For anyone who leads people, in a school, a district, or a business, it's a rare look at how alignment really works at scale.

Strategic Syncing releases every other Monday. Follow on Spotify, and join us on YouTube, Apple Podcasts, Amazon Music, LinkedIn & Instagram.

#Leadership #DeviceManagement #Aviation

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 advantage

A 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 does
• How to avoid bureaucracy in a leadership group of 30+
• The "work toward a yes" philosophy that flips traditional IT culture
• Hiring for growth potential, not pedigree
• Leading 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 team

A 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 staff
• Stepping into AI early, intentionally, and without all the answers
• The leadership lesson that only time can teach you
• What it costs to lead people you deeply care about

🎧 Listen on your favourite platform:

🟢 Youtube

🎙️ Apple Podcasts

📦 Amazon Music

📲 Follow the conversation:

Instagram → @stratgicsyncing

LinkedIn → 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 staff
• Stepping into AI early, intentionally, and without all the answers
• The leadership lesson that only time can teach you
• What 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