This mini episode explores why SaaS Statements of Work can never fully eliminate ambiguity and how organizations should plan for that reality. We discuss unknown requirements, the inevitability of change orders, and how stronger upfront discovery helps reduce risk, control cost, and evaluate scope changes without losing momentum.   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/  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 

This mini episode explores why traditional SaaS contracts break down when applied to probabilistic AI systems. We discuss the limits of using generative AI for contract review, how liability and accountability are shifting, and why AI clauses increasingly resemble professional services disclaimers. The conversation centers on risk ownership, decision authority, and why organizations remain responsible for outcomes, even when AI drives the recommendation or action.   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/  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 

This mini episode explores why SaaS contract review requires more than a surface read. We discuss the need for experienced authority in interpreting licensing, legal terms, and commercial structures, why legal and financial negotiations must happen together, and how gaps in expertise can lead to excess cost or long-term risk baked into the agreement.   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/  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 

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/  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     

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/  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 

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/  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 

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/  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 

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 

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 

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 

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 

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 

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 

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 

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

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

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

Automation shouldn’t erase the human element, it should enhance it. In this discussion, Kara and Kyler dig into how AI can be used to augment rather than replace workers, the difference between inspiring work and busywork, and how leaders can use automation to build capability instead of fear.   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

If AI adoption feels like chaos disguised as innovation, you’re not alone. Kara Bombell explains why 95 percent of enterprise AI initiatives miss the mark. From executive blind spots to short-term cost thinking, she and Kyler reveal the cultural and strategic gaps that keep “ethical AI” stuck in slide decks instead of practice.   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

Ethics isn’t a checklist, it’s a culture. Kara and Kyler break down how leaders can embed ethical frameworks directly into AI projects, why human-first design matters, and how sustainable implementation depends on more than compliance documents. This episode explores what it means to create organizational ethics that last longer than the next software upgrade.   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