This mini episode focuses on balancing speed and clarity during high-pressure software contracting. We discuss why rushing increases risk, how vendor pressure shapes timelines, and practical ways leaders can move quickly without making costly mistakes.

Watch the full episode here: https://youtube.com/live/RNuGSva75qo?feature=share 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/  Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  

This mini episode explores the tradeoffs between system ownership and shared responsibility through SaaS, using cybersecurity as the lens. We discuss how AI driven threats change the risk equation, when owning your technology becomes a liability, and how vendor scale can shift security responsibility. The conversation closes with a practical decision framework focused on pain points, root cause analysis, and solution options that extend beyond software replacement to include process and policy change. The goal is to help leaders make grounded, healthy technology decisions without jumping to predetermined answers.

Watch the full episode: https://youtube.com/live/RnKYGv9bdVQ 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/  Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  

This mini episode breaks down what modernization really costs beyond the price tag. We discuss uncovering operational expenses tied to legacy systems, separating business value from sales-driven promises, and why discovery takes time. The conversation also explores ownership versus vendor dependency, business risk, and how AI-driven cyber threats are reshaping security decisions. The focus is on choosing the right path based on capability, control, and long-term risk.

Watch the full episode: https://youtube.com/live/RnKYGv9bdVQ 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  

This mini episode looks at why legacy system challenges are often less about technology and more about people. We discuss how over customization, retiring experts, and undocumented knowledge leave organizations unsure of how their systems actually work. The conversation explores workforce lifecycle risk, talent availability, and the tipping point where maintaining legacy expertise becomes unsustainable. The focus is on recognizing when it is time to transition with intention rather than waiting until critical knowledge walks out the door.

Watch the full episode: https://youtube.com/live/RnKYGv9bdVQ 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  

This mini episode breaks down a common claim in technology discussions: “our system can’t do X.” We explore how often this reflects a true product limitation versus a lack of understanding, experience, or prioritization. The conversation looks at how enhancement backlogs form, how unmet requests compound over time, and when rebuilding internally costs more than change. We also examine the tradeoffs of SaaS driven enhancements, security and compliance pressures, and why discovery and honest prioritization matter more than assumptions or vendor-driven narratives.

Watch the full episode: https://youtube.com/live/RnKYGv9bdVQ 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  

This mini episode explores why older systems sometimes deliver more value than newer software and why replacing them should never be an emotional decision. We break down how to assess real pain points, distinguish usability issues from functional limitations, and identify when a system truly can no longer support growth. The conversation also examines the long-term cost of ownership, rising SaaS subscription risk, over-customization, workforce considerations, and licensing constraints. The takeaway is clear: modernization decisions must be grounded in business logic, not aesthetics or vendor pressure.

Watch the full episode: https://youtube.com/live/RnKYGv9bdVQ 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  

This mini episode examines what low automation rates and increasing autonomous task capability really mean for the next 24 months of human AI workflows. We discuss why full autonomy remains rare, how AI should build organizational capacity rather than simply replace labor, and why prompt training alone is not an AI strategy. The conversation focuses on practical integration, data readiness, and the gap between AI experimentation and real workflow automation in the enterprise.

Watch full episode here: https://youtube.com/live/nUjTUjC7exc?feature=share 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  

This mini episode explains how to navigate AI adoption without getting pulled into market hype. We discuss why simple approaches work, why end user engagement matters, and how to avoid vendor lock-in when building AI capabilities. We outline the importance of owning your strategy and show why effective integration depends on change intelligence working directly with project execution. The episode offers a clear, disciplined approach to adopting technology in a noisy marketplace.

Watch full episode here: https://youtube.com/live/nUjTUjC7exc?feature=share 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  

This mini episode explains how to measure the value of AI and organizational change using clear operational metrics. We discuss why understanding your current state matters, how to set quantifiable expectations, and how to build an internal rate of return for AI and change initiatives. The goal is to help leaders move past vague promises and evaluate technology investments with the same rigor used for capital projects.

Watch full episode here: https://youtube.com/live/nUjTUjC7exc?feature=share 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  

We take a direct look at how AI, process design, and organizational execution really come together. Boards are asking about AI, but the real conversation starts with strategy, people, and the systems that hold everything in place. This episode breaks down why execution architecture matters, how leadership can align technology with business objectives, and what it takes to turn innovation into meaningful outcomes.

Watch full episode here: https://youtube.com/live/nUjTUjC7exc?feature=share 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/