AI Questions Every Leader Should Be Asking
Most AI projects fail because of unclear problem definition. Answer three questions before writing a single prompt to improve your odds.
Practical perspectives on the decisions, patterns, and trade-offs that technology leaders face every week. Grounded in real experience across engineering, product, and security.
Topics span AI adoption, system modernization, security programs, engineering culture, and the mechanics of technical leadership. Written for CTOs, VPs of Engineering, and the operators building what comes next.
Most AI projects fail because of unclear problem definition. Answer three questions before writing a single prompt to improve your odds.
Agentic AI demos are impressive. But turning them into reliable, sustainable enterprise systems takes more than a prompt and agent builder
If you ever spent time on Stack Overflow, you know how humbling it could be. No matter how carefully you wrote your question, someone would…
When Your AI Lives on Your Laptop
If you’ve ever pitched a big idea to the board or exec team, you know the feeling. You’re leaning in, waving your hands, excited about the…
This is Part 2 of my AI at the Crossroads series. If you haven’t read Part 1, you can find it here: AI at the Crossroads (Part 1): Why the…
In the ever-evolving world of technology, the most powerful leadership lessons often emerge from adversity… those crossroads where economic…
Let me be honest: I never thought I’d look back on the early 2010s with nostalgia, at least not for server racks and gear. But here we are…
Years ago, I got passed over for a role I thought I had in the bag. I’d led complex projects, built high-performing teams, and stayed…
There’s a moment when I’m reviewing something I’ve written or analyzing a tricky issue, and I pause…not because I’m done, but because I…
The “build, buy, or partner” conversation isn’t new. We’ve been navigating that one forever. AI just made it messier, or maybe more urgent…
Alright, here’s the thing.
“I built a revenue-generating AI startup in a weekend.”
Most “technical” decisions aren’t technical. They’re organizational choices masquerading as system design. They may feel technical, but in reality...
You can always tell when a technology is peaking on the hype curve; everyone is talking about it, few are doing it well, and almost no one…
We talk extensively about tools, architectures, frameworks, and roadmaps in tech. However, when it comes to leadership, especially at the executive level...
Every few years, a new wave of innovation promises to reduce the need for software developers. But the opposite keeps happening…
To remedy this issue, organizations must become more intentional about data. Below, let’s examine why being “data intentional” is essential…
The Paper Problem
Explore how organisations can overcome the challenge of flat data, which restricts business insight and…
It seems like every crime show includes a few scenes where we see that the detective has built a wall of pictures, newspaper clippings…
Understanding the context can lead to accelerated insight through AI and machine learning. To be competitive…
Moving beyond data capture and enriching your data into a business-critical context to fuel digital workers will lead the way to…