Kenneth Thomas: What Your IT Company Won't Tell Your Board

Your organization pays an outside IT company. Your board asks what you spend on technology and where the risk sits. And nobody on staff can give a straight answer. Kenneth Thomas—Fractional Chief Technology Officer based in Tallahassee, Florida—joins us for a conversation about cybersecurity, artificial intelligence, and how to manage the IT vendors you already pay. Kenneth spent more than 20 years running information technology for organizations in sports media, broadcast news, public health, state government, and higher education. He also taught IT at Keiser University, where he served as faculty member and program director, and at Florida A&M University as an adjunct instructor. Today he works with leaders who rely on an outside IT company but have no senior technology executive on staff. He holds an MBA from Florida A&M University and is finishing his doctorate in Technology Management. In January 2027, he speaks at the Future of Education Technology Conference on technology risk at the board level. In this episode, we explore: • What leaders should ask their IT company before signing another contract renewal • Who in your organization should be able to tell the board where technology risk sits—and what happens when nobody can • How to know if your organization has outgrown its outside IT company • What a Fractional Chief Technology Officer does that an IT company doesn't • Your staff is already using AI tools. What should a usage policy cover? • Cybersecurity questions every board member should ask at least once a year • How a leader with no technical background can tell whether technology spending makes sense • How growing up in rural Gadsden County shaped Kenneth's view on technology access • What 20 years in sports media, public health, and state government taught him about who really owns technology decisions • The most common mistake organizations with 50 to 250 staff make managing technology Connect with Kenneth Thomas: 🌐 Website: kenneththomas.com 💼 LinkedIn: \[Please provide handle] 📘 Facebook: \[Please provide handle] Take the Free Technology Assessment: Ten questions. About three minutes. You get two scores back—one showing how your technology runs day to day, and one showing how well your leadership sees and steers it. Plus a short note on what to look at first. Built for executive directors, CEOs, owners, and board members at organizations with 50 to 250 staff. No technical background needed, and answers stay private. 🔗 https://www.kenneththomas.com/assessment Interested in Being a Guest? If you're a leader, entrepreneur, or executive with insights to share about leadership, business, and entrepreneurship in an AI world, I'd love to connect. Submit your information here to be considered for a future episode: 🔗 https://www.joinpodmatch.com/leadershipbusinessandentrepreneurshipinanaiworld