ON THIS EPISODE ➤ How to learn leadership from bad boss experiences➤ The servant leadership framework that actually delivers business results➤ Simple technique for eliminating cultural barriers in global team meetings➤ Individual management assessment strategies for different personality types➤ Building IT reputation through equal service excellence across all organizational levels What happens when an English major accidentally becomes an IT VP through reverse mentorship?At a Boston-area property management company, Larry Monuteaux leads IT initiatives spanning everything from end-user support to building management systems and tenant amenities. With 30 years of accidental IT experience starting from data entry and backup tape...

ON THIS EPISODE ➤ How to move from AI hype to practical business implementation ➤ The Vibe Workflow System for rapid prototyping without coding skills ➤ Why perfect AI content isn’t always better than authentic human voice ➤ Building AI guardrails that enable rather than block innovation ➤ Start Small Framework: From personal fun projects to enterprise deployment What happens when a healthcare IT leader builds AI applications in shower conversations at 2 AM? At a healthcare organization bound by HIPAA compliance and patient safety requirements, Yossi Akselrud implements AI faster than most tech companies. With years of experience navigating...

ON THIS EPISODE ➤ How network aggregators eliminate ISP management chaos➤ Real strategies for migrating from expensive MPLS to resilient SD-WAN➤ Why POTS line costs are exploding and how to escape before bills double➤ Building proactive network monitoring instead of reactive firefighting➤ The zero-CapEx approach that gets executive buy-in for network upgrades What happens when IT leaders stop accepting “we’re better because we suck less” from internet providers? At Airespring, Jeffrey Armstrong (Director of Solutions) and Clinton Devereaux (Solutions Engineering) have spent 22 years perfecting network aggregation—turning the nightmare of managing multiple carriers into strategic competitive advantage. From consolidating 50+...

ON THIS EPISODE ➤ Crisis leadership: How to achieve 100% team placement during organizational failure ➤ The amplified impact of leadership presence and why every interaction matters 10x more ➤ Player-coach assessment framework for determining optimal IT focus areas ➤ Scaling IT through explosive growth: From $250M to $500M revenue management ➤ Business-first mindset transformation from technical expert to strategic leader What happens when an IT leader faces both complete organizational failure and explosive business growth? At Shepherd Electric Supply, Tom Shock serves as Director of Information Technology, leading IT initiatives for a company that has doubled from $250 million...

ON THIS EPISODE ➤ How a Master’s in Russian History translates to IT leadership success ➤ The EBITDA Impact Framework for connecting IT initiatives to business outcomes ➤ Real-world AI automation that saved $2M+ by eliminating 4,400 manual service calls ➤ Why IT leaders must learn business operations before optimizing them ➤ Moving from cost center “last slide” to presenting at every board meeting What happens when academic analysis meets ice distribution efficiency? At Arctic Glacier, one of North America’s largest ice manufacturers, Doug Saunders leads IT initiatives that power a complex global supply chain. With a Master’s degree in...

ON THIS EPISODE ➤ Why giving orders at work doesn’t work anymore ➤ How to work with difficult people who challenge you ➤ Why tech skills aren’t enough to be a good leader ➤ How to talk to your boss and coworkers better ➤ Why you need to understand what your company really does What happens when a military guy tries to run an IT team? Troy Penny used to be in the Air Force. He programmed computers for the military. When he gave orders, people had to listen. Then he got a job at a regular company. Big problem....

ON THIS EPISODE ➤ Why IT leaders get constant pushback on their recommendations ➤ The communication framework that prevents 90% of leadership problems ➤ How to stop making unilateral decisions that kill trust ➤ Building the “Culture of IT” where technology drives business success ➤ Moving from cost center to strategic business partner Why do IT leaders face more pushback than any other department? Dr Charles Harris, Transformational CIO at Tampa Bay Buccaneers, knows this pain firsthand. Running IT for a Super Bowl-winning organization taught him that the biggest technology challenges aren’t technical—they’re cultural. Harris breaks down why IT leaders...

ON THIS EPISODE ➤ Why technical skills aren’t the most important factor in IT hiring ➤ How to manage cybersecurity compliance across 6 different countries ➤ The partner selection strategy when you can’t master everything alone ➤ Why AI enhances jobs instead of replacing them (if you adapt correctly) ➤ How to align IT priorities with business goals through involvement, not just communication What happens when you’re responsible for IT operations spanning Europe, India, Japan, and the United States? Fabio drops some uncomfortable truths about IT hiring. Most leaders still think technical skills matter most – he doesn’t. He’s built...

ON THIS EPISODE ➤ The critical difference between technical expertise and leadership effectiveness ➤ How to recognize when supportive environments become career traps ➤ Strategic lateral movement for long-term career growth ➤ The listening leadership framework that transforms team dynamics ➤ Managing up through business translation of technical concepts ➤ Professional development strategies for small and mid-market IT leaders What happens when technical expertise isn’t enough for leadership success? April Marquez, ERP Implementation Specialist at FNS Fresh Produce, shares her journey from IT manager to strategic career pivot. With experience leading IT departments as a team of one and navigating...

Listen now: subscribe and join 1,000s of IT Leaders changing the face of IT. Now… ON THIS EPISODE ➤ How IT leaders navigate career growth in geographically isolated markets ➤ The unexpected value of cross-functional experience in sales for IT professionals ➤ Building professional community and peer networks in small market environments ➤ Overcoming gender dynamics and communication challenges in technology leadership ➤ Strategic approaches to cybersecurity consulting for vulnerable small businesses What happens when geographic isolation meets professional ambition? At Bowers and Kubota in Honolulu, Hawaii, Charissa Wong serves as Director of IT and Security, leading technology initiatives for...