Work in 2025 might be efficient, but it’s also getting real weird. In this episode, we take a look at what happens when digital transformation forgets the human side. From productivity scores and AI bosses to yogurt-tracking fridges, we explore how over-automation can turn smart systems into uncomfortable workplaces. Just because you can automate something doesn’t mean you should. The best tech leaders know the real question isn’t how to automate more, it’s what should be left alone.

Struggling with agile rollouts? Get the FREE guide: https://theconfluencial.com/agile-whitepaper-form 

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

In this episode, we break down why your org chart might be the real reason your tech projects are stuck. When no one owns decisions and everyone shares the blame, even the best tools won’t save you. We share real-world examples of messy implementations, where the lack of accountability (not the software)caused chaos. If your systems are failing, it might be time to stop blaming the tech and start fixing the structure behind it.

Struggling with agile rollouts? Get the FREE guide: https://theconfluencial.com/agile-whitepaper-form 

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

In this episode, we call out the buzzword-filled mission statements that sound great on paper but fall apart in practice. If your culture claims to unlock human potential, why is your turnover rate sky-high? If you’re reimagining the future of work, why are your systems stuck in the past? We break down why real leadership starts with accountability, not PowerPoint slides, and how to align your big goals with actual results.

Struggling with agile rollouts? Get the FREE guide: https://theconfluencial.com/agile-whitepaper-form 

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

This episode dives into the chaos of enterprise software buying and why so many demos are more fiction than fact. We break down the red flags, the vendor buzzwords that mean nothing, and how to protect your organization from feature soup and inflated contracts. If you’re spending millions on software, treat it like hiring an executive. Own the process, ask hard questions, and never let the demo run the deal.

Struggling with agile rollouts? Get the FREE guide: https://theconfluencial.com/agile-whitepaper-form 

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

This episode calls out the executives confusing AI hype with real leadership. We unpack the difference between vision and discipline, why chatbots won’t save a crumbling service model, and how throwing money at AI without fixing operations, data, or strategy is just noise. If your foundation is a mess, no tool at all, including AI, is going to save it.

Struggling with agile rollouts? Get the FREE guide: https://theconfluencial.com/agile-whitepaper-form 

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

This episode breaks down how leaders can build a culture where teams feel confident questioning trends and pushing back on hype. We explore the dangers of blindly following competitors, the importance of clarity around trade-offs, and why strategic decision-making starts with empowering teams to ask why, not just chase what’s new.

Struggling with agile rollouts? Get the FREE guide: https://theconfluencial.com/agile-whitepaper-form 

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

Right before you sign the check, ask if the value is still there. This episode explores the one checkpoint every tech decision needs. We look at how shifting goals, unclear roles, and evolving scope can quietly erode ROI, and why revisiting your original purpose helps keep projects on track.

Struggling with agile rollouts? Get the FREE guide: https://theconfluencial.com/agile-whitepaper-form 

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

Chasing shiny tech without strategy is a fast track to wasted spend. In this episode, we explore how leaders can build a culture where teams are empowered to challenge hype and push back on fear-based decisions driven by competitor noise. From setting clear expectations at the top to reinforcing strategic alignment over trend-chasing, this conversation breaks down how to foster thoughtful evaluation instead of reactive implementation. Plus, we tackle the danger of defaulting to competitor behavior and the importance of focusing on your unique value, not what others appear to be doing.

Struggling with agile rollouts? Get the FREE guide: https://theconfluencial.com/agile-whitepaper-form 

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

Building technology is only half the battle. If you don’t plan to sustain it, you’re setting yourself up for failure. In this episode, we unpack the long-term realities of tech investments, from maintenance responsibilities to the hidden costs of integration platforms. Whether it’s modular ERP systems, iPaaS requirements, or underestimated support needs, leaders must go beyond license fees to evaluate total cost of ownership. Learn how overlooking sustainment and integration planning can double your tech budget and derail strategic ROI.

Struggling with agile rollouts? Get the FREE guide: https://theconfluencial.com/agile-whitepaper-form 

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

Technology should fuel your long-term business strategy, not distract from it. In this episode, we explore how leaders can evaluate technology investments as integrated, strategic enablers rather than isolated tools. From understanding opportunity cost and resource reallocation to avoiding siloed implementations without business sponsorship, we highlight what it really means to align tech with vision. If you're spending 90% of your budget on one innovation, are you still hitting the rest of your top five priorities? 

Struggling with agile rollouts? Get the FREE guide: https://theconfluencial.com/agile-whitepaper-form 

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