ByteSized

When Systems “Can’t” Deliver: Product Limits vs Business Priorities

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/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

When Legacy Systems Outperform Modern Software

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/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

Human–AI Workflows and the Reality of Enterprise Automation

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/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

Cutting Through AI Noise with Practical Integration Strategy

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/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

Hoe to Measure AI ROI with Real Operational Metrics

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/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

Execution Architecture and AI Governance

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/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

Shadow IT, sunk costs, and the breakdown of business alignment

This episode looks at what happens when shadow IT spending surfaces after the money is already gone and IT is left supporting tools no one agreed on. We explore why these breakdowns occur, how misaligned decision making creates technical debt, and why organizations need a clear liaison function that connects business requirements with IT capability. The discussion highlights practical steps for restoring alignment, setting realistic priorities, and building the structure needed to prevent costly surprises in the future.
 
Watch the full episode here: https://youtube.com/live/17w7BHi0xQQ 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/  Follow me on TikTok https://www.tiktok.com/@kylercheatham  Connect with The Confluencial https://www.linkedin.com/company/the-confluencial  Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial 

Why Experience Still Gets Left Out

Even in 2025, user experience remains an afterthought in many transformation projects. In this episode, the Extensia team explains why measuring “delight” is difficult, why digital initiatives are still tech-led, and how the rise of AI and low-code tools is changing the conversation. Kyler, Pradnya, and Nic break down how leaders can finally put people (rather than platforms) at the center of digital change.
 
Watch the full episode here: https://youtube.com/live/FFDHnUMMibY 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

Designing for Humans, Not Systems

Digital transformation isn’t just about upgrading technology, it’s about designing for people. Kyler Cheatham speaks with Pradnya and Nic from Extensia, a Merkle company, about what experience-centric transformation really means and why human emotion, not software functionality, should drive design decisions. They discuss how user delight can define success and why a transformation that ignores experience will always fall short.
 
Watch the full episode here: https://youtube.com/live/FFDHnUMMibY 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial

When Ethics Meet ROI

Can doing the right thing cost you revenue? Kara Bombell and Kyler Cheatham explore why ethical AI isn’t a barrier to profit, it’s a blueprint for long-term sustainability. They cover how executives can balance risk and responsibility, why “phase two ethics” never works, and what it takes to make ethical AI a core part of business value instead of an afterthought.
 
Watch the full podcast here: https://www.youtube.com/live/eaE4TeZLXTI 
 
Connect with me on LinkedIn https://www.linkedin.com/in/kylercheatham/ Follow me on Instagram https://www.instagram.com/kyler_cheatham_tech/ Follow me on TikTok https://www.tiktok.com/@kylercheatham Connect with The Confluencial https://www.linkedin.com/company/the-confluencial Follow The Confluencial on TikTok: https://www.tiktok.com/@the.confluencial