Phillip R. Kennedy
@prokennedy.bsky.social
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
I've spent 30 years watching what great technical leaders actually do.
Almost none of it looks like leadership on paper.
18 things I've seen the best ones do: 🧵
Almost none of it looks like leadership on paper.
18 things I've seen the best ones do: 🧵
February 18, 2026 at 1:56 PM
I've spent 30 years watching what great technical leaders actually do.
Almost none of it looks like leadership on paper.
18 things I've seen the best ones do: 🧵
Almost none of it looks like leadership on paper.
18 things I've seen the best ones do: 🧵
The VP forwarded the CEO's angry email to the whole engineering team at 9:47 PM on a Thursday. Daniel's manager replied-all at 9:48: "I'll handle this. Everyone log off."
Twelve seconds. Two completely different leaders. 🧵
Twelve seconds. Two completely different leaders. 🧵
February 16, 2026 at 3:25 PM
The VP forwarded the CEO's angry email to the whole engineering team at 9:47 PM on a Thursday. Daniel's manager replied-all at 9:48: "I'll handle this. Everyone log off."
Twelve seconds. Two completely different leaders. 🧵
Twelve seconds. Two completely different leaders. 🧵
The best engineer on the team hadn't shipped a single feature she was proud of in fourteen months.
Elena used to prototype solutions on Saturday mornings because the problems were interesting. She'd sketch architecture diagrams on napkins at lunch. 🧵
Elena used to prototype solutions on Saturday mornings because the problems were interesting. She'd sketch architecture diagrams on napkins at lunch. 🧵
February 13, 2026 at 2:07 PM
The best engineer on the team hadn't shipped a single feature she was proud of in fourteen months.
Elena used to prototype solutions on Saturday mornings because the problems were interesting. She'd sketch architecture diagrams on napkins at lunch. 🧵
Elena used to prototype solutions on Saturday mornings because the problems were interesting. She'd sketch architecture diagrams on napkins at lunch. 🧵
Her exit interview was two sentences.
"I'm not leaving for more money. I'm leaving for better sleep."
I didn't understand. She was one of our best. Shipped constantly. Never complained. Dashboard had her as a top performer.
I asked what she meant. 🧵
"I'm not leaving for more money. I'm leaving for better sleep."
I didn't understand. She was one of our best. Shipped constantly. Never complained. Dashboard had her as a top performer.
I asked what she meant. 🧵
February 10, 2026 at 4:42 PM
Her exit interview was two sentences.
"I'm not leaving for more money. I'm leaving for better sleep."
I didn't understand. She was one of our best. Shipped constantly. Never complained. Dashboard had her as a top performer.
I asked what she meant. 🧵
"I'm not leaving for more money. I'm leaving for better sleep."
I didn't understand. She was one of our best. Shipped constantly. Never complained. Dashboard had her as a top performer.
I asked what she meant. 🧵
I used to think I was bad at engineering.
Took me three years to realize I was just good at internalizing bad management. 🧵
Took me three years to realize I was just good at internalizing bad management. 🧵
February 6, 2026 at 2:32 PM
I used to think I was bad at engineering.
Took me three years to realize I was just good at internalizing bad management. 🧵
Took me three years to realize I was just good at internalizing bad management. 🧵
"You'll own the ERP migration."
I looked around the conference table. Waited for her to finish the sentence. Hand it to someone senior. Add a caveat.
She didn't. 🧵
I looked around the conference table. Waited for her to finish the sentence. Hand it to someone senior. Add a caveat.
She didn't. 🧵
February 5, 2026 at 2:29 PM
"You'll own the ERP migration."
I looked around the conference table. Waited for her to finish the sentence. Hand it to someone senior. Add a caveat.
She didn't. 🧵
I looked around the conference table. Waited for her to finish the sentence. Hand it to someone senior. Add a caveat.
She didn't. 🧵
He'd been the technical anchor for six years. The one who knew every skeleton in every closet. Any architectural decision ran through him.
Then the stack shifted. 🧵
Then the stack shifted. 🧵
February 4, 2026 at 2:55 PM
He'd been the technical anchor for six years. The one who knew every skeleton in every closet. Any architectural decision ran through him.
Then the stack shifted. 🧵
Then the stack shifted. 🧵
His resume made me nervous.
PhD in distributed systems. Published papers. Built the exact architecture we'd been struggling with for eighteen months. At three different companies.
My first instinct wasn't excitement.
It was to find reasons not to hire him. 🧵
PhD in distributed systems. Published papers. Built the exact architecture we'd been struggling with for eighteen months. At three different companies.
My first instinct wasn't excitement.
It was to find reasons not to hire him. 🧵
February 3, 2026 at 4:26 PM
His resume made me nervous.
PhD in distributed systems. Published papers. Built the exact architecture we'd been struggling with for eighteen months. At three different companies.
My first instinct wasn't excitement.
It was to find reasons not to hire him. 🧵
PhD in distributed systems. Published papers. Built the exact architecture we'd been struggling with for eighteen months. At three different companies.
My first instinct wasn't excitement.
It was to find reasons not to hire him. 🧵
The engineer quit for a 20% raise and a bigger title. No hard feelings. Good opportunity.
Three months later he called me.
"Quick question. Was it always this chaotic everywhere? Or did something change after I left?"
I laughed. Nothing had changed. 🧵
Three months later he called me.
"Quick question. Was it always this chaotic everywhere? Or did something change after I left?"
I laughed. Nothing had changed. 🧵
February 2, 2026 at 2:37 PM
The engineer quit for a 20% raise and a bigger title. No hard feelings. Good opportunity.
Three months later he called me.
"Quick question. Was it always this chaotic everywhere? Or did something change after I left?"
I laughed. Nothing had changed. 🧵
Three months later he called me.
"Quick question. Was it always this chaotic everywhere? Or did something change after I left?"
I laughed. Nothing had changed. 🧵
Your resume is about to become a conversation between two AIs.
Neither of them is you. 🧵
Neither of them is you. 🧵
January 30, 2026 at 4:24 PM
Your resume is about to become a conversation between two AIs.
Neither of them is you. 🧵
Neither of them is you. 🧵
"Do you actually want us to ship this? Or are we just building prototypes for your ideas?"
The room went quiet.
A senior engineer had finally said what everyone had been thinking. The VP sat there, mouth open, reaching for words that wouldn't come. 🧵
The room went quiet.
A senior engineer had finally said what everyone had been thinking. The VP sat there, mouth open, reaching for words that wouldn't come. 🧵
January 29, 2026 at 2:33 PM
"Do you actually want us to ship this? Or are we just building prototypes for your ideas?"
The room went quiet.
A senior engineer had finally said what everyone had been thinking. The VP sat there, mouth open, reaching for words that wouldn't come. 🧵
The room went quiet.
A senior engineer had finally said what everyone had been thinking. The VP sat there, mouth open, reaching for words that wouldn't come. 🧵
I asked him about his best manager.
Strong candidate. Decade of experience. We were halfway through the interview.
He paused. Then he told me about a VP of Engineering from eight years ago. 🧵
Strong candidate. Decade of experience. We were halfway through the interview.
He paused. Then he told me about a VP of Engineering from eight years ago. 🧵
January 28, 2026 at 2:17 PM
I asked him about his best manager.
Strong candidate. Decade of experience. We were halfway through the interview.
He paused. Then he told me about a VP of Engineering from eight years ago. 🧵
Strong candidate. Decade of experience. We were halfway through the interview.
He paused. Then he told me about a VP of Engineering from eight years ago. 🧵
"Psychological safety" was printed on the office wall.
Then production went down at 3 AM.
The VP's first question wasn't "What broke?"
It was "Who was on call and why didn't they escalate faster?" 🧵
Then production went down at 3 AM.
The VP's first question wasn't "What broke?"
It was "Who was on call and why didn't they escalate faster?" 🧵
January 27, 2026 at 4:05 PM
"Psychological safety" was printed on the office wall.
Then production went down at 3 AM.
The VP's first question wasn't "What broke?"
It was "Who was on call and why didn't they escalate faster?" 🧵
Then production went down at 3 AM.
The VP's first question wasn't "What broke?"
It was "Who was on call and why didn't they escalate faster?" 🧵
$640K in engineering time. Launched on time. Under budget. 3% adoption.
Nobody called it a failure because it shipped. 🧵
Nobody called it a failure because it shipped. 🧵
January 26, 2026 at 1:47 PM
$640K in engineering time. Launched on time. Under budget. 3% adoption.
Nobody called it a failure because it shipped. 🧵
Nobody called it a failure because it shipped. 🧵
You're excellent at saving failing projects.
That's exactly why nobody trusts you to build something new. 🧵
That's exactly why nobody trusts you to build something new. 🧵
January 24, 2026 at 1:36 PM
You're excellent at saving failing projects.
That's exactly why nobody trusts you to build something new. 🧵
That's exactly why nobody trusts you to build something new. 🧵
Twelve people in a conference room. Six months into a CRM migration everyone knew was drowning.
$40K a month in burn. Zero business value shipped. And there we sat, discussing "revised timelines" and "adjusted scope." 🧵
$40K a month in burn. Zero business value shipped. And there we sat, discussing "revised timelines" and "adjusted scope." 🧵
January 23, 2026 at 2:57 PM
Twelve people in a conference room. Six months into a CRM migration everyone knew was drowning.
$40K a month in burn. Zero business value shipped. And there we sat, discussing "revised timelines" and "adjusted scope." 🧵
$40K a month in burn. Zero business value shipped. And there we sat, discussing "revised timelines" and "adjusted scope." 🧵
"This is high priority."
I watched a VP send this message to five engineers.
What they heard: 🧵
I watched a VP send this message to five engineers.
What they heard: 🧵
January 21, 2026 at 2:59 PM
"This is high priority."
I watched a VP send this message to five engineers.
What they heard: 🧵
I watched a VP send this message to five engineers.
What they heard: 🧵
A recruiter asked if I knew any AI experts.
"How do you define AI expert?" I asked.
"Someone who's used ChatGPT for six months."
That's not an expert. That's a customer. 🧵
"How do you define AI expert?" I asked.
"Someone who's used ChatGPT for six months."
That's not an expert. That's a customer. 🧵
January 20, 2026 at 3:02 PM
A recruiter asked if I knew any AI experts.
"How do you define AI expert?" I asked.
"Someone who's used ChatGPT for six months."
That's not an expert. That's a customer. 🧵
"How do you define AI expert?" I asked.
"Someone who's used ChatGPT for six months."
That's not an expert. That's a customer. 🧵
I have been seeing this take going around lately:
Wake up: 6.7" screen.
Work: 16" screen.
Relax: 55" screen.
Sleep: 6.7" screen.
Congratulations. You've optimized your entire existence into rectangles of varying sizes.
The scariest part is that it feels completely normal 🧵
Wake up: 6.7" screen.
Work: 16" screen.
Relax: 55" screen.
Sleep: 6.7" screen.
Congratulations. You've optimized your entire existence into rectangles of varying sizes.
The scariest part is that it feels completely normal 🧵
January 16, 2026 at 3:08 PM
I have been seeing this take going around lately:
Wake up: 6.7" screen.
Work: 16" screen.
Relax: 55" screen.
Sleep: 6.7" screen.
Congratulations. You've optimized your entire existence into rectangles of varying sizes.
The scariest part is that it feels completely normal 🧵
Wake up: 6.7" screen.
Work: 16" screen.
Relax: 55" screen.
Sleep: 6.7" screen.
Congratulations. You've optimized your entire existence into rectangles of varying sizes.
The scariest part is that it feels completely normal 🧵
The answer to your biggest problem is sitting in someone's head three desks away.
They're not hiding it.
They just stopped telling you.
A VP called me last month. Deadlines slipping. Morale tanking. He'd tried new processes, better tools, more standups. Nothing worked. 🧵
They're not hiding it.
They just stopped telling you.
A VP called me last month. Deadlines slipping. Morale tanking. He'd tried new processes, better tools, more standups. Nothing worked. 🧵
January 15, 2026 at 2:29 PM
The answer to your biggest problem is sitting in someone's head three desks away.
They're not hiding it.
They just stopped telling you.
A VP called me last month. Deadlines slipping. Morale tanking. He'd tried new processes, better tools, more standups. Nothing worked. 🧵
They're not hiding it.
They just stopped telling you.
A VP called me last month. Deadlines slipping. Morale tanking. He'd tried new processes, better tools, more standups. Nothing worked. 🧵
Twenty minutes into the interview, he realized she knew more about distributed systems than he'd learned in fifteen years.
His first instinct wasn't excitement. It was panic.
"If I hire her, what's my value?" 🧵
His first instinct wasn't excitement. It was panic.
"If I hire her, what's my value?" 🧵
January 14, 2026 at 2:36 PM
Twenty minutes into the interview, he realized she knew more about distributed systems than he'd learned in fifteen years.
His first instinct wasn't excitement. It was panic.
"If I hire her, what's my value?" 🧵
His first instinct wasn't excitement. It was panic.
"If I hire her, what's my value?" 🧵
You ship every deadline. Solve every outage. Work weekends debugging production.
Still no promotion. No visibility. No seat at the strategy table.
You assume you're not ready. Not senior enough. Not strategic enough.
Maybe you're not the problem. 🧵
Still no promotion. No visibility. No seat at the strategy table.
You assume you're not ready. Not senior enough. Not strategic enough.
Maybe you're not the problem. 🧵
January 13, 2026 at 2:41 PM
You ship every deadline. Solve every outage. Work weekends debugging production.
Still no promotion. No visibility. No seat at the strategy table.
You assume you're not ready. Not senior enough. Not strategic enough.
Maybe you're not the problem. 🧵
Still no promotion. No visibility. No seat at the strategy table.
You assume you're not ready. Not senior enough. Not strategic enough.
Maybe you're not the problem. 🧵
They sat in architecture meetings, silent, watching me design their systems.
I thought I was helping. 🧵
I thought I was helping. 🧵
January 12, 2026 at 2:25 PM
They sat in architecture meetings, silent, watching me design their systems.
I thought I was helping. 🧵
I thought I was helping. 🧵
You'd get paged at 2 AM if a service degraded 5%.
Your career could drift for five years. No alert. No dashboard. No incident review.
Just a slow Tuesday that turns into a slow decade. 🧵
Your career could drift for five years. No alert. No dashboard. No incident review.
Just a slow Tuesday that turns into a slow decade. 🧵
January 9, 2026 at 2:43 PM
You'd get paged at 2 AM if a service degraded 5%.
Your career could drift for five years. No alert. No dashboard. No incident review.
Just a slow Tuesday that turns into a slow decade. 🧵
Your career could drift for five years. No alert. No dashboard. No incident review.
Just a slow Tuesday that turns into a slow decade. 🧵
Can someone please vibe code a browser that won't consume every byte of available memory?
January 8, 2026 at 3:26 PM
Can someone please vibe code a browser that won't consume every byte of available memory?