The business knows what it needs, but that does not mean it knows how to translate those needs into technical requirements. This episode explores why that gap creates friction between business and IT and how strong business analysis turns operational needs into requirements teams can actually build from.

Watch the full episode here: https://youtube.com/live/oMFwSxHlAtk 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

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Software sales teams often understand your processes just well enough to sell the solution, leaving the unknowns for discovery later. This episode explores how oversimplified requirements and pre-sales assumptions turn into implementation promises that may be impossible to keep.

Watch the full episode here: https://youtube.com/live/oMFwSxHlAtk 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

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Legacy technology is not automatically old, broken, or ready to be replaced. This episode explores why the better question is whether your existing systems still fit the business you are today and where you are going next.

Watch the full episode here: https://youtube.com/live/oMFwSxHlAtk 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

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AI should strengthen critical thinking, not replace it. This episode explores how employees and leaders can use AI to analyze information and improve productivity without outsourcing the judgment, context, and decision-making that make their roles valuable.

Watch the full episode here: https://youtube.com/live/hcDXEzsorT0 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

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Technical debt is rarely caused by one aging system. This episode breaks down five major contributors, from code quality and IT skill shortages to custom development, vendor dependency, and weak architecture standards.

Watch the full episode here: https://youtube.com/live/hcDXEzsorT0 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

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Tech debt often starts with decisions made long before a system becomes outdated. This episode explores how unclear ownership, deferred phase-two work, and weak governance turn newly implemented technology into tomorrow’s technical debt.

Watch the full episode here: https://youtube.com/live/hcDXEzsorT0 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

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Organizations cannot afford to put AI on hold while they clean up years of technical debt. This episode explores how to tackle both at once by prioritizing high-impact tech debt, improving governance, and using AI to reduce the maintenance burden holding IT back.

Watch the full episode here: https://youtube.com/live/hcDXEzsorT0 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

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Tech debt consumes the time and resources organizations need to move forward. This episode explores how legacy systems create a growing maintenance burden and where AI can help reduce that burden so IT can focus on modernization and business growth.

Watch the full episode here: https://youtube.com/live/hcDXEzsorT0 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

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Business and IT do not have to like each other, but they do have to work together. This episode explores how friction turns into distrust, why teams often assume bad intent, and what it takes to rebuild a productive working relationship.

Watch the full episode here: https://youtube.com/live/-_zYge0UYBo 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

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Buying technology without understanding your requirements is an expensive way to learn what does not fit. This episode explores why software purchases need due diligence before the business ends up paying for the wrong tool and shopping for its replacement.

Watch the full episode here: https://youtube.com/live/-_zYge0UYBo 

Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ 

Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/