Strategic guidance for executives on AI transformation, investment decisions, and organizational change
You’ve been here long enough to see the pattern. Your CxOs want AI. They talk about it in all-hands meetings. They mention it to the board. They’ve probably put it in your objectives. But ask them to change how engineering works with product? Silence. Suggest consolidating toolchains? “Not the right time.” Propose breaking down silos? … Read more
Part One: The Text The text from board chair Amanda arrived at 6:47 AM on a Tuesday: “We need to talk about the competitive situation.” David sat in his kitchen and felt his stomach drop. Four years as CEO of Velocity Systems. Grew it from $80M to $200M ARR. Built what he thought was a … Read more
Alex has been trying to hire an engineer for three months. Not just any engineer. A specific person who works at a company that ships features in days while his 47-person team takes weeks. He’s watched them launch three features in the time his team shipped one. Same complexity. Same domain. They just move faster. … Read more
Your AI tools are working. Your SDLC isn’t. Your board asked about AI ROI six months ago. You showed them the metrics: 89% AI coding assistant adoption. AI-generated code at 67% of commits. Developer satisfaction up. Productivity improved 11%. They nodded. They approved more budget. But privately, you know something’s off. Your competitor—the one that … Read more
My daughter Lily is nearly five. Last Sunday over waffles, I told her: “Put the plate on the counter.” She walked straight to the bathroom counter. I almost got frustrated. Then I realized—she’d just washed her hands there before breakfast. In her context, that WAS “the counter.” So I changed my approach. Now I ask: … Read more
When tractors arrived on farms in the early 1900s, most farmers bought them to plow their same 40 acres faster. Those farms didn’t survive the Depression. The farmers who surived? They bought more tractors, hired displaced farmers with domain expertise, and scaled to 400 acres. Your competitors just made Choice 3. You’re still debating Choice … Read more