Leadership

Your company just announced a new AI initiative. You hired a Head of AI. You’re “exploring use cases.” You have 56 meetings on your calendar about it. And your engineers? They’re laughing at you. Not with you. AT you. The worst part? You have no idea. After two decades in technology and software engineering, I’ve watched this pattern repeat itself across countless organizations. Let me show you exactly why your AI strategy is failing—and what you can do about it. ...

There’s a really weird communication pattern that I keep seeing all the time in big companies and small companies. Picture this: You’re hiring an employee, consultant, contractor, whatever you want to call them. You think this person has good experience and you’re paying them hundreds of thousands of dollars. Once you hire them, you tell them, “Hey, I want you to do this.” This is super weird. You’re not explaining the problem. You’re just trying to use this person as a human tool. ...

Have you ever been in a meeting where people just keep putting band-aids on problems but don’t discuss how they came to that point? Let me talk about the decision chain mindset. Understanding the Decision Chain Picture this: You make a decision, or someone makes a decision at a high level. Let’s call this Decision A. Based on this decision, another decision is made. Let’s name it Decision B. And based on that, now you have to make another decision. Let’s call it Decision C. ...

I walked into my neighborhood coffee shop for my regular Americano, but walked out with a lesson, a leadership lesson. Let me explain. The Beginning This coffee shop opened here in my town around three years ago. Since then, I have become a regular customer. If I have time in the morning, I just walk there, I’m even the first or second customer, I have my morning coffee and walk back home. That’s how I start my days. ...