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Phillip R. Kennedy

@prokennedy.bsky.social
166 followers 300 following 3.6K posts

Fractional CIO/CTO → I help non-technical leaders make technical decisions | Scaling Businesses from $0 to $3 Billion | IT Crisis Management | Technical Ghostwriting | Dad humor too

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Phillip R. Kennedy @prokennedy.bsky.social · 21h
A 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.🧵
Eleven hours of process. two hours of work. I built that.
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Phillip R. Kennedy @prokennedy.bsky.social · 29/09/2026
His hands were shaking over the keyboard. He'd deployed the change that took checkout offline, and everyone in the room knew it.🧵
His hands stopped shaking by the third sentence.
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Phillip R. Kennedy @prokennedy.bsky.social · 28/09/2026
Seventy-three slides. Rehearsed twelve times. The CEO stopped me at slide four.🧵
73 slides. He stopped me at four.
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Phillip R. Kennedy @prokennedy.bsky.social · 26/09/2026
My six-year-old's favorite toy broke last week. He looked at it, put it down, and went to find another one.🧵
He looked at the broken toy, put it down, and went to find another one.
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Phillip R. Kennedy @prokennedy.bsky.social · 25/09/2026
Somewhere 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.🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 24/09/2026
Sometime 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.🧵
The next Y2K won't be a date bug. It'll be a reading problem.
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Phillip R. Kennedy @prokennedy.bsky.social · 23/09/2026
A 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.🧵
Nobody in the building could read it. the whole company ran on it.
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Phillip R. Kennedy @prokennedy.bsky.social · 22/09/2026
Promptwreck (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.🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 19/09/2026
The best career decision I ever made was taking a phone job in a ski town.🧵
I took the job for the ski pass. I've been in tech ever since.
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Phillip R. Kennedy @prokennedy.bsky.social · 18/09/2026
An 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.🧵
the partner walked and took the code. all of it.
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Phillip R. Kennedy @prokennedy.bsky.social · 17/09/2026
Her 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. 🧵
She used to carry the message. Now she writes it.
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Phillip R. Kennedy @prokennedy.bsky.social · 16/09/2026
I'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.🧵
Green is not the same as gone.
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Phillip R. Kennedy @prokennedy.bsky.social · 15/09/2026
"I built this in Lovable over the weekend." 🧵
I built this over the weekend. Nobody had asked the team to.
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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." 🧵
I don't need him to understand it. I need him to make the call.
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Phillip R. Kennedy @prokennedy.bsky.social · 12/09/2026
Three weeks after a restructuring took his job, a VP I know called with news.🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 11/09/2026
I Am a Framework Hoarder prokennedy.substack.com/p/i-am-a-fra...
prokennedy.substack.com
I Am a Framework Hoarder
My 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...
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Phillip R. Kennedy @prokennedy.bsky.social · 11/09/2026
He sat in the exec meeting every week and never said a word.🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 10/09/2026
The AI had been wrong for six weeks. It was polite about it, so nobody noticed.🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 09/09/2026
Two engineers, same level, same review cycle. One got promoted. The other had caught a $200K discrepancy, and her promotion packet said "Led infrastructure improvements." 🧵
She caught the $200k. Her packet said "led infrastructure improvements."
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Phillip R. Kennedy @prokennedy.bsky.social · 08/09/2026
"Can't we just use AI?"🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 07/09/2026
My first budget as a technology leader was laughable. Not in hindsight. In the room.🧵
Nobody explained the rules. Everyone assumed I knew them.
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Phillip R. Kennedy @prokennedy.bsky.social · 05/09/2026
The first time I worked with my wife, I was the one who hired her. 🧵
The first time I worked with my wife, I was the one who hired her.
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Phillip R. Kennedy @prokennedy.bsky.social · 04/09/2026
Eight months into building an AI recommendation engine, a CTO I worked with stopped the project.🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 03/09/2026
He wanted AI to shave fifteen minutes off every job. His own data wanted to tell him something bigger.🧵
He asked AI to make the trucks faster. His data wanted to talk about which trucks make money.
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Phillip R. Kennedy @prokennedy.bsky.social · 02/09/2026
Every Tuesday morning, someone exported the orders to a spreadsheet, fixed them by hand, and loaded them back in. I asked why. Nobody knew. 🧵
I asked why. Nobody knew.
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Phillip R. Kennedy @prokennedy.bsky.social · 01/09/2026
"The last guy said it was done." 🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 31/08/2026
The demo was flawless. Six weeks after go-live, they pulled the plug.
The demo was flawless. Six weeks later, they pulled the plug.
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Phillip R. Kennedy @prokennedy.bsky.social · 29/08/2026
I 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. 🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 28/08/2026
"I found something closer to what I want to do. Thank you for everything." 🧵
The exit interview was two sentences. the real one took six months.
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Phillip R. Kennedy @prokennedy.bsky.social · 27/08/2026
For three days every month, the sharpest analyst in the company disappeared. The board deck ate her.🧵
Three days a month went to assembling the deck. That was never the job.
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Phillip R. Kennedy @prokennedy.bsky.social · 26/08/2026
I once kept one of my best engineers exactly where she was for two years. On purpose.🧵
I kept my best engineer exactly where she was. on purpose.
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Phillip R. Kennedy @prokennedy.bsky.social · 25/08/2026
The roadmap review stalled on one line item. The CFO leaned back: "Why does this take six months?"🧵
Why does this take six months? Six months is a shape, not a number.
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Phillip R. Kennedy @prokennedy.bsky.social · 24/08/2026
The leadership team had been debating build-versus-buy for a quarter when I arrived. The debate was already costing more than either answer.🧵
The debate cost more than either answer.
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Phillip R. Kennedy @prokennedy.bsky.social · 22/08/2026
Years ago, as a VP, a senior engineer told me my reviews were costing the team three days a sprint.🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 21/08/2026
A CEO I worked with asked his team for something simple: a list of every software subscription the company paid for. It took three weeks.🧵
Nobody stole anything. Nobody was watching either.
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Phillip R. Kennedy @prokennedy.bsky.social · 20/08/2026
Six weeks after the AI rollout, proposals were drafted in an hour instead of a week. Deals were closing exactly as fast as before.🧵
The drafts took an hour. the approvals still took three weeks.
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Phillip R. Kennedy @prokennedy.bsky.social · 19/08/2026
The CEO asked why the launch slipped. He got four confident answers, each backed by a chart. None of them matched.🧵
four executives. four accurate charts. no diagnosis.
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Phillip R. Kennedy @prokennedy.bsky.social · 18/08/2026
"Can't we just buy something off the shelf?"🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 17/08/2026
In thirty years of technology assessments, I've almost never found the problem I was hired to find. 🧵
I almost never find the problem I was hired to find.
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Phillip R. Kennedy @prokennedy.bsky.social · 15/08/2026
I 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.🧵
Why don't you just pick the one you like?
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Phillip R. Kennedy @prokennedy.bsky.social · 14/08/2026
A founder I know still personally calls every new customer in their first week. A real call, from him. 🧵
Some things don't scale. That's exactly why they're worth keeping.
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Phillip R. Kennedy @prokennedy.bsky.social · 13/08/2026
Their entire AI policy was one word long: don't. A year later, competitors had lapped them, and they still felt safe. Safe and behind.🧵
Good AI governance doesn't slow you down. it's how you get to move fast.
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Phillip R. Kennedy @prokennedy.bsky.social · 12/08/2026
Nobody failed. Every team did exactly their job. The project died anyway, in the gap between them where no one was looking. 🧵
The work didn't fail in a department. it failed in the seam between two.
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Phillip R. Kennedy @prokennedy.bsky.social · 11/08/2026
Here's the sentence I wish more leaders heard before they bought anything. 🧵
AI is a multiplier. Multipliers don't care what they multiply.
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Phillip R. Kennedy @prokennedy.bsky.social · 10/08/2026
The roadmap was beautiful. Eighteen months, color coded, every team represented. It survived exactly one bad quarter. 🧵
Your roadmap isn't a plan. It's a list of things you hope happen.
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Phillip R. Kennedy @prokennedy.bsky.social · 08/08/2026
The worst day that company had, I watched two leaders handle the same crisis in the same room. 🧵
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Phillip R. Kennedy @prokennedy.bsky.social · 07/08/2026
A 40-year-old distribution company I worked with had a meeting problem, though they called it a follow-through problem. 🧵
Wait, what did we actually decide?
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Phillip R. Kennedy @prokennedy.bsky.social · 06/08/2026
The automation worked perfectly. That was the problem. 🧵
Automate the task. Never automate the judgement.
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Phillip R. Kennedy @prokennedy.bsky.social · 05/08/2026
When Alice went out for six weeks, three departments quietly stopped working. Nobody had planned for that, because nobody knew Alice was holding them up. 🧵
One spreadsheet. one person. your whole operation leans on it.
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Phillip R. Kennedy @prokennedy.bsky.social · 04/08/2026
A CEO once apologized to me for not understanding his own infrastructure. He thought that was the gap he needed to close. 🧵
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