Phillip R. Kennedy

@prokennedy.bsky.social

164 Followers 296 Following

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

Wait, what did we actually decide?
Automate the task. Never automate the judgement.
One spreadsheet. one person. your whole operation leans on it.
In 30 days, I see what you stopped noticing years ago.
Automate a broken process and you make it permanent.
Want to quiet the data center backlash? Give everyone within 100 miles unlimited AI tokens, and the training to use them.
Two people noticed.
Nobody acts on the dashboard. That's not a data problem.
$80k decisions have AI. $8M decisions don't.
A vendor you can't leave isn't a partner. It's a landlord.
You rolled out AI to everyone. nothing changed. here's why
What does it cost me to leave you in three years?
You didn't buy software. you bought your chaos, running faster.
Your technical debt isn't a code problem. It's a decision you keep postponing.
Two identical companies. today. in three years, one runs the other.
you would never run okrs bottom-up, one team at a time. That's how you're deploying AI.
Your most important decisions are running on your worst data. an afternoon proves it.
AI in every function. None where the decisions get made. Your board should ask why.
Your AI won't fail loud. It'll fail polite, and cost you a quarter's margin.
Your org chart has a soft middle. AI just found it.
The implementation sequence
The SaaS strategic layer
The franchise playbook
What would need to be true?
The CEO's unexamined decisions
The upside-down company
Who builds what now?
The PM who touched the code.
The planning tax
What the engineer actually thinks.
The latent demand graveyard.
340 approved tickets. complete specs. not a single one was going to get built.
847 duplicate product entries. descriptions from 2020. then they trained an AI on it.
a few months into intentional ignorance, I realized I was doing it ad hoc
Saying no to things is overrated
about three years ago I stopped following the news. not reduced. stopped.
Last vacation I took, I deleted every new message when I got back. every email. every slack notification. selected all. deleted.
my phone doesn't buzz. hasn't in years. i run a technology practice.
The first Tuesday evening I didn't watch a deployment, I didn't know what to do with myself.
Nobody tells you it feels like grief.
the 30/70 audit
She was ready to ship Monday. It shipped Thursday. Not a technical issue. Her VP hadn't reviewed it yet.
1:14 PM. Lying in bed. Refreshing a deployment dashboard for a deployment I wasn't running.
Resolution Is a Status Change. Solving Is a State Change.
'Led Infrastructure Improvements.' Three Words for Three Months.
Full calendar, zero impact.
They saved $450k. it cost them three times that.
she was three weeks from a PIP. six months later she was the reason the security audit found zero vulnerabilities.
Three questions that separate a foundation from a prayer
Your 15 years of industry knowledge just became your biggest technical asset
The most expensive words in AI are 'close enough'
The AI gave us exactly what we asked for. That was the problem.
Every corporate environment I've worked in was designed for people who aren't me.