Phillip R. Kennedy @prokennedy.bsky.social · 21hA two-hour fix took eleven hours of process to reach a sprint. I timed it. Then I recognized the process, because I'd built one just like it.🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 29/09/2026His hands were shaking over the keyboard. He'd deployed the change that took checkout offline, and everyone in the room knew it.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 28/09/2026Seventy-three slides. Rehearsed twelve times. The CEO stopped me at slide four.🧵 200
Phillip R. Kennedy @prokennedy.bsky.social · 26/09/2026My six-year-old's favorite toy broke last week. He looked at it, put it down, and went to find another one.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 25/09/2026Somewhere around 2031, a platform engineer who retired in 2027 is going to get a phone call. On the other end, a CTO half her age who has never seen a stack trace he didn't ask an agent to explain.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 24/09/2026Sometime around 2031, a company is going to go looking for a programmer who can read code without asking a model to explain it. They'll find him in a woodshop. He'll be 66.🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 23/09/2026A company doing well over $400 million a year ran on software written by a husband and wife in Ohio. Nobody in the building could read it.🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 22/09/2026Promptwreck (n.): an app built by prompts, extended by prompts, patched by prompts, until nobody in the building can read it and the model can't either.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 19/09/2026The best career decision I ever made was taking a phone job in a ski town.🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 18/09/2026An outside development partner had built a client's product for most of a year. Then the relationship soured, and the partner walked. He took the code with him. All of it.🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 17/09/2026Her old specs said "add a filter to the dashboard." Her new ones flagged that the metrics endpoint returned unbounded results and would time out on accounts with more than ten thousand events. Same PM. Three months apart. 🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 16/09/2026I've told this story before. Resolution time down 40 percent, customer satisfaction down 15. I keep coming back to it, because the part I skipped is the part that matters now.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 15/09/2026"I built this in Lovable over the weekend." 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 14/09/2026"I don't need my CTO to understand AI development. I need him to trust that I do and make the call." 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 12/09/2026Three weeks after a restructuring took his job, a VP I know called with news.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 11/09/2026I Am a Framework Hoarder prokennedy.substack.com/p/i-am-a-fra...prokennedy.substack.comI Am a Framework HoarderMy college advisor called me “academically unfocused.” By then I had been a computer science major, a physics major, an aerospace engineering major, and an accounting major, and I was on my way to fin... 011
Phillip R. Kennedy @prokennedy.bsky.social · 11/09/2026He sat in the exec meeting every week and never said a word.🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 10/09/2026The AI had been wrong for six weeks. It was polite about it, so nobody noticed.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 09/09/2026Two engineers, same level, same review cycle. One got promoted. The other had caught a $200K discrepancy, and her promotion packet said "Led infrastructure improvements." 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 07/09/2026My first budget as a technology leader was laughable. Not in hindsight. In the room.🧵 210
Phillip R. Kennedy @prokennedy.bsky.social · 05/09/2026The first time I worked with my wife, I was the one who hired her. 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 04/09/2026Eight months into building an AI recommendation engine, a CTO I worked with stopped the project.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 03/09/2026He wanted AI to shave fifteen minutes off every job. His own data wanted to tell him something bigger.🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 02/09/2026Every Tuesday morning, someone exported the orders to a spreadsheet, fixed them by hand, and loaded them back in. I asked why. Nobody knew. 🧵 120
Phillip R. Kennedy @prokennedy.bsky.social · 31/08/2026The demo was flawless. Six weeks after go-live, they pulled the plug. 100
Phillip R. Kennedy @prokennedy.bsky.social · 29/08/2026I came to fatherhood late. Friends were planning graduations while I was learning to carry a sleeping two-year-old and a car seat at once. 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 28/08/2026"I found something closer to what I want to do. Thank you for everything." 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 27/08/2026For three days every month, the sharpest analyst in the company disappeared. The board deck ate her.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 26/08/2026I once kept one of my best engineers exactly where she was for two years. On purpose.🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 25/08/2026The roadmap review stalled on one line item. The CFO leaned back: "Why does this take six months?"🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 24/08/2026The leadership team had been debating build-versus-buy for a quarter when I arrived. The debate was already costing more than either answer.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 22/08/2026Years ago, as a VP, a senior engineer told me my reviews were costing the team three days a sprint.🧵 210
Phillip R. Kennedy @prokennedy.bsky.social · 21/08/2026A CEO I worked with asked his team for something simple: a list of every software subscription the company paid for. It took three weeks.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 20/08/2026Six weeks after the AI rollout, proposals were drafted in an hour instead of a week. Deals were closing exactly as fast as before.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 19/08/2026The CEO asked why the launch slipped. He got four confident answers, each backed by a chart. None of them matched.🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 18/08/2026"Can't we just buy something off the shelf?"🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 17/08/2026In thirty years of technology assessments, I've almost never found the problem I was hired to find. 🧵 100
Phillip R. Kennedy @prokennedy.bsky.social · 15/08/2026I was in the kitchen last week, thinking out loud about a decision I'd been circling for a month. Weighing it, re-weighing it, narrating the tradeoffs to nobody in particular.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 14/08/2026A founder I know still personally calls every new customer in their first week. A real call, from him. 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 13/08/2026Their entire AI policy was one word long: don't. A year later, competitors had lapped them, and they still felt safe. Safe and behind.🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 12/08/2026Nobody failed. Every team did exactly their job. The project died anyway, in the gap between them where no one was looking. 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 11/08/2026Here's the sentence I wish more leaders heard before they bought anything. 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 10/08/2026The roadmap was beautiful. Eighteen months, color coded, every team represented. It survived exactly one bad quarter. 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 08/08/2026The worst day that company had, I watched two leaders handle the same crisis in the same room. 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 07/08/2026A 40-year-old distribution company I worked with had a meeting problem, though they called it a follow-through problem. 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 06/08/2026The automation worked perfectly. That was the problem. 🧵 110
Phillip R. Kennedy @prokennedy.bsky.social · 05/08/2026When Alice went out for six weeks, three departments quietly stopped working. Nobody had planned for that, because nobody knew Alice was holding them up. 🧵 210
Phillip R. Kennedy @prokennedy.bsky.social · 04/08/2026A CEO once apologized to me for not understanding his own infrastructure. He thought that was the gap he needed to close. 🧵 111