After 2 decades in software development, I pieced together a few personal conversations I’ve had former peers who are now senior leaders about adopting AI in the SDLC. Here’s a common theme that’s emerged in late 2025. Clay called me on a Tuesday night, which meant something was wrong. We’d worked together for six years … Read more
The “developer happiness” movement of the 2010s was one of the most successful organizational transformations in software history. It also might be one of the most misunderstood. Because it was never actually about happiness. What We Were Really Solving In 2008, enterprise software organizations had a problem they couldn’t see. They were optimizing for procurement … Read more
The engines are purring. The Atlantic is glass. You’re three hours out of Miami, pointed toward Bimini, and everything is perfect until your old academy roommate asks the question. “So when are you actually going to use AI to build something?” You’re standing at the helm of your 62-foot weekender. Your boat. Your friends are … Read more
An executive leader at a Fortune 500 company asked me last month whether we could help their QA team teach AI their “really unique testing process.” That same week, a startup with eight engineers and AI agents shipped more tested, production-ready features than that enterprise’s 400-person engineering organization shipped all quarter. The executive’s question wasn’t … Read more
Bottom Line Up Front Your principal engineers are submitting procurement requests for every AI coding tool on the market. One wants the CLI tool. Another wants the VS Code fork. Someone else swears the web-based IDE is the future. And Carl is building his own from scratch. You’re stalling on all of them because your … Read more
BOTTOM LINE: Would you be surprised if your organization spent less than 20% of engineering capacity creating customer value? You’re stuck here because your org has so many handoffs it looks like an Olympic marathon relay. Value stream mapping reveals the same number told two ways: value density (aspirational metric that makes boards feel hopeful) … Read more
The Moment You Knew Something Was Broken You were in the board meeting when it happened. Q3 review. Your CEO clicked to the product roadmap slide—the one you and your VP of Product spent six weeks perfecting—and the room went quiet. “So we’ll have dynamic pricing by… Q2 next year?” The lead investor leaned back. … Read more
You standardized your sales tools years ago. Now your competitors are doing the same with AI development—and measuring what you can’t. The Disaster You Already Prevent in Sales Your top AE—the one closing $5M deals—didn’t pick Salesforce. Your CRO did. That rep adapted in two weeks and got back to selling. You did this because … Read more
They just made you Chief AI Officer. Or VP of AI. Whatever title they invented when the board asked about AI strategy. Here’s what nobody told you: this job will be great for your career and probably end badly. Not because you’ll fail—because they don’t know what they hired you to do. That’s fine. You’re … Read more
Tuesday, 3:47 PM Your phone buzzed. Terry: Can I call you later? Terry is the fake name of the leader, but Terry could be you, or a friend of yours—there are a lot of Terrys right now. You’ve known Terry for years. Ten years at their company. Joined right after the IPO. You’d grab drinks … Read more