Category
Technology leadership for CEOs, boards and the people who run IT.
Most AI conversations start with tools: which platform, which model, which vendor. The organizations that get value from AI start somewhere else entirely - with friction, ownership and a few uncomfortable leadership questions.
They sound interchangeable, but they're different jobs. Hiring the wrong one is one of the most expensive mistakes a growing company makes, and AI has made it easier to get wrong.
Most growing companies don't need a full-time CIO. But almost all of them need what a CIO brings. Here are the signs you've outgrown "our IT guy handles it," and how fractional leadership fills the gap.
"Only Sarah knows how that system works." Every organization has someone like her - brilliant, reliable and quietly becoming a single point of failure. Here's how it happens, why it's a leadership problem, and how to fix it without losing her.
"We'll figure it out when we're bigger" sounds sensible when you're moving fast. But later always arrives, and it charges interest. Here's where the bill usually comes from, and how to take shortcuts without getting trapped by them.
Most people think hiring managers scan for technologies, certifications and years of experience. I don't. In the first 30 seconds I'm answering one question - and in a world of AI-polished resumes, it matters more than ever.
"How long would it take someone to get to our customer data if they really wanted to?" Most leadership teams can't answer that. Here's why breaches really happen, the questions that reveal where you stand, and how to talk about security in terms a board can act on.
Green status reports, hour-long update meetings, and projects quietly burning behind them. Why status reporting so often hides the truth - and what I replaced it with, starting with the most productive meeting I ever killed.
You don't need an audit to find out whether your technology spending is working. You need five questions, your leadership team and 45 minutes. Here's the agenda.
