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Leading IT into the future as a business force multiplier. Discover how IT Business Executives are impacting the business world, growing their careers, and influencing end-users without sacrificing work life balance AND never worrying about money again.
*****DISCLAIMER***** All views, opinions, and statements made by guests on this show do not represent the beliefs of Phil Howard, or any entity whatsoever with which I have been, am now, or will be affiliated. Any statements, views, random thoughts, or opinions expressed by myself do not necessarily reflect my personal beliefs (could easily be misconstrued) and are not the official policy/position of my agency and affiliated partners. Finally, because human beings are characteristically prone to flaws and mistakes, I warn all listeners to think critically for yourself and seek true knowledge before taking action upon anything.
*****DISCLAIMER***** All views, opinions, and statements made by guests on this show do not represent the beliefs of Phil Howard, or any entity whatsoever with which I have been, am now, or will be affiliated. Any statements, views, random thoughts, or opinions expressed by myself do not necessarily reflect my personal beliefs (could easily be misconstrued) and are not the official policy/position of my agency and affiliated partners. Finally, because human beings are characteristically prone to flaws and mistakes, I warn all listeners to think critically for yourself and seek true knowledge before taking action upon anything.
391 Episodes
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ON THIS EPISODE ➤ Why 75% of employees are using unapproved AI tools right now ➤ How to consolidate AI usage onto one secure, compliant platform ➤ Live demonstration of no-code agent building for HR, sales, and operations ➤ Real enterprise security: SOC2, ISO 27001, and GDPR compliance explained ➤ Managing AI chat logs and preventing data leaks ➤ Building custom agents that integrate with your existing systems What happens when IT leaders stop fearing employee AI usage and start securing it? In this special live demo episode, Aaron Bailey, General Manager of Devs.ai, tackles the number one concern keeping...
ON THIS EPISODE ➤ The real difference between AI hype and actual enterprise AI adoption ➤ Why most change management initiatives fail (and what to do instead) ➤ How to identify and solve the right problems before executing strategy ➤ The brutal truth about AI’s impact on workforce transformation ➤ Change management frameworks that actually work for AI implementation What happens when you combine change management expertise with real AI adoption strategy? Dima Syrotkin, CEO and Co-founder of Pandatron, helps Fortune 500 companies like Panasonic, Mitsubishi, and KPMG identify genuine AI opportunities and accelerate adoption. But his journey started in...
ON THIS EPISODE ➤ What network aggregation actually means (and why most IT leaders have never heard of it)➤ How to consolidate 50+ circuits onto one invoice with co-terminus contracts➤ Real strategies for 20%+ cost savings while improving service➤ POTS replacement tactics saving thousands monthly➤ The leadership question that gets executive buy-in: “What do we lose by not doing this?” Managing internet circuits across multiple locations feels like herding cats—if the cats all had different phone numbers and billing cycles. Chris Soucie’s spent 20 years at New Horizons Communications, and he’s breaking down the aggregator model most IT leaders don’t...
ON THIS EPISODE ➤ Why most Azure migrations fail before they start—and how to plan properly from day one ➤ The real difference between CSPs who just sell licenses and partners who drive value ➤ How to reduce Azure costs by 80% through proper architecture and licensing optimization ➤ Why IT leaders must learn to ask for help instead of fighting fires alone ➤ Moving from reactive firefighting to strategic business partnership What happens when submarine leadership principles meet cloud infrastructure strategy? At Heliant Technologies, Kenon Bliss leads infrastructure practices across the Microsoft stack, helping organizations navigate the complex world...
ON THIS EPISODE ➤ Why IT presentations lose executives in 30 seconds—and the backward storytelling framework that changes everything ➤ How a CFO cut AWS costs 20% in three weeks through daily DevOps partnership sessions ➤ The Five Boss Model: Why your CFO wants to fund IT projects but can’t understand your proposals ➤ Innovation budget reality: Why 15-20% waste is expected and how to frame experimentation ➤ The Gemba Principle: Japanese leadership concept for IT-business cross-cultural integration ➤ KeyBanc benchmarking system to justify IT spend as percentage of revenue What happens when a CFO reveals he has five different...
ON THIS EPISODE ➤ The “wedding cake” framework for IT stack management and system lifecycle planning ➤ Why being embedded in every department’s presentation beats having your own slide deck ➤ The change management cycle: denial, anger, bargaining, depression, acceptance ➤ Time-Resources-Money triangle: the iron law of ERP implementation ➤ How to select the right ERP tier and avoid the “cement around your ankles” problem James Dean Miller has implemented over 600 ERP projects with a 93% on-time, on-budget success rate. As CIO of Migrate Ammunitions and former co-founder of CSS International, he’s led organizations through Oracle, SAP, and Microsoft...
ON THIS EPISODE ➤ Why IT teams become “the Department of No” and how to transform that culture ➤ The Walsh KPI Framework: 5 metrics that prove IT’s EBITDA impact ➤ Using golf as a leadership assessment tool for vendors and partners ➤ The ACAIC method for overcoming objections without saying no ➤ From “users” to “customers” – the language shift that changes everything What happens when golf course wisdom meets IT leadership? Grant Walsh, Director of IT in Charlotte, North Carolina, brings 20+ years of IT leadership experience and a unique perspective: he evaluates vendors, partners, and leadership potential...
ON THIS EPISODE: ➤ Why overthinking kills IT progress and how to break the paralysis ➤ The unique advantages of managing both IT and HR responsibilities ➤ How coffee conversations solve more problems than formal meetings ➤ Real AI use cases: CAD plant identification and expense categorization ➤ Developing people when there’s no room for advancement ➤ Why looking stupid makes you learn faster What happens when you combine IT leadership with HR responsibilities? Michael McKirchy, Director of Information Technology and HR at Lurvey Landscape Supply, reveals how this unique dual role creates unexpected advantages in technology adoption and team...
ON THIS EPISODE ➤ Why 95% of enterprise AI implementations fail (MIT study insights) ➤ The confusion matrix framework for evaluating AI vendors ➤ How to approach AI as an automation problem, not magic ➤ Red flags when AI salespeople make unrealistic promises ➤ Data quality as the foundation for successful AI adoption What happens when a data scientist turned CIO reveals the brutal truth about AI adoption? Jaron Jones, data scientist turned CIO and university instructor, breaks down why most companies are failing spectacularly with AI implementation. With a recent MIT study showing 95% of Agentic AI projects either...
ON THIS EPISODE ➤ How to transition IT from cost center to business enabler ➤ Building stakeholder relationships through lunch and learn programs ➤ AI implementation strategy that balances innovation with security ➤ Transforming reactive “car mechanic” mindset to proactive business partner ➤ Earning executive respect through consistent value demonstration What happens when a chemical engineer becomes an AI-driven IT leader who saves companies millions? At a major energy company, Benny Zhang serves as VP of Information Technology, transforming how IT departments prove their strategic value. Starting his career as a chemical engineer in China—where his father brought him a...
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...
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