Category: AI & Copilot

For the first thirteen weeks of this series, I focused on my personal AI journey—my frustrations, breakthroughs, and hard-won literacy. But while I was learning AI one prompt at a time, something larger was happening across our organization. We were conducting an experiment without realizing it: What happens when you encourage AI adoption without expecting it?… Continue reading AI Over 40 Series – Week 14: How AI Moved from Experimentation to Expectation

After three months of building what I proudly called my AI Ready Data Model—a unified structure connecting budgets, forecasts, actuals, operational metrics, and sales pipeline data—I was finally ready for my big AI moment. I uploaded everything, took a breath, and asked AI to normalize the data for regression analysis. Instantly: “Token limit exceeded.” I… Continue reading AI Over 40 Series – Week 13: When Your AI Miracle Hits the Infrastructure Wall

When the breakthrough isn’t finding the right solution—but finally asking why you’ve been living with the problem. As a Microsoft partner, I’ve spent years asking: What problems can I solve for my clients? I’ve searched for patterns—shared pain points that justify building repeatable, scalable solutions. The challenge? Most clients have learned to live with their… Continue reading AI Over 40 Series – Week 12: The Questions You’re Not Asking (And Why That’s the Real Problem)

When everyone says it’s impossible, it’s time to rethink what AI can do After our acquisition by Cherry Bekaert, I was tasked with finding quick wins to leverage our expanded service offerings. My first idea was to introduce a tax partner to a key client for a sales-and-use tax review. Simple on paper—but I quickly… Continue reading AI Over 40 Series – Week 11: How AI Literacy is Revolutionizing Solution Design

How AI literacy turned a routing nightmare into a three-hour solution When a key team member went on extended leave, I inherited their workload—including routing every signed client agreement to the right stakeholders. My predecessor’s email-template system looked simple: copy, paste, fill blanks, send. In practice, I lacked the data those templates required, forcing me… Continue reading AI Over 40 Series – Week 10: Creating Simple Automations with AI

Why we keep making the same mistakes How a room full of leaders convinced me we’re repeating 50 years of hype Last week, I joined a panel of seasoned executives buzzing about “agentic AI” and its promise to transform every facet of business—from client engagement to workforce structure. The big ask? Hire AI specialists. But… Continue reading AI Over 40 Series – Week 9: Literacy Before Agency

Why the most critical AI skills have nothing to do with prompt engineering Here’s a deceptively simple question that transformed how I collaborate with AI: Do I need to be polite to a machine? You might scoff—“Greg, it’s a computer, not a person!”—but hear me out. AI models are trained on the full spectrum of… Continue reading AI Over 40 Series – Week 8: Building Your AI User Manual

How a forecasting nightmare led to my biggest AI breakthrough In Week 1, I shared how a frustrating forecasting exercise pushed me onto this AI journey. This week, I’ve come full circle: the same challenge showed me why relying on a single AI platform is too limiting—and how a multi-AI approach can transform not only… Continue reading AI Over 40 Series – Week 7: The Multi-AI Approach