In this episode, we flip the script on success and talk about why the best people in tech, AI, and fast-moving industries are comfortable losing. From scrapping your favorite idea to giving up control and letting someone else take the credit, we break down three types of losing that actually build long-term impact. If you're serious about leading, innovating, and getting paid, it's time to lose the ego and embrace the process.

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 that happens when companies roll out AI customer service without proper training, testing, or a backup plan. From misunderstood accents to outdated scripts and frustrating dead-ends, we explore why smart systems can still create terrible experiences. AI isn’t supposed to be perfect, but your implementation strategy should account for that. If your tech adds friction instead of removing it, the problem isn’t the tool, it’s how you’re using 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 get real about what it means to be mid-implementation with no clear path to success. From shifting project sponsors to software picked at a bar, we cover the warning signs your digital transformation is headed for disaster. If your team is being rushed, your methodology keeps changing, or “Phase 2” is where all the answers live, it’s time to reassess. You’ll learn what to watch for, how to protect yourself, and why documenting your wins might be the smartest move you make this year.

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/ 

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/