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
The CFO cuts you off mid-sentence: "This infrastructure thing seems expensive. Can't we just use the cloud?"
You've spent three weeks modeling costs. Built a detailed TCO analysis. Documented every tradeoff.
He hasn't read any of it. 🧵
You've spent three weeks modeling costs. Built a detailed TCO analysis. Documented every tradeoff.
He hasn't read any of it. 🧵
November 25, 2025 at 2:57 PM
The CFO cuts you off mid-sentence: "This infrastructure thing seems expensive. Can't we just use the cloud?"
You've spent three weeks modeling costs. Built a detailed TCO analysis. Documented every tradeoff.
He hasn't read any of it. 🧵
You've spent three weeks modeling costs. Built a detailed TCO analysis. Documented every tradeoff.
He hasn't read any of it. 🧵
I studied five disciplines in college.
Computer Science. Physics. Aerospace Engineering. Accounting. Finance.
My professors thought I couldn't commit. My advisor said I was "academically unfocused."
Twenty years later, that lack of focus is why companies hire me. 🧵
Computer Science. Physics. Aerospace Engineering. Accounting. Finance.
My professors thought I couldn't commit. My advisor said I was "academically unfocused."
Twenty years later, that lack of focus is why companies hire me. 🧵
November 24, 2025 at 2:49 PM
I studied five disciplines in college.
Computer Science. Physics. Aerospace Engineering. Accounting. Finance.
My professors thought I couldn't commit. My advisor said I was "academically unfocused."
Twenty years later, that lack of focus is why companies hire me. 🧵
Computer Science. Physics. Aerospace Engineering. Accounting. Finance.
My professors thought I couldn't commit. My advisor said I was "academically unfocused."
Twenty years later, that lack of focus is why companies hire me. 🧵
Six kids. One baseball. Pure chaos.
I'm watching my son's 6-and-under game when a grounder rolls into the infield.
All six kids abandon their positions and sprint toward the ball like it's the only thing that matters. 🧵
I'm watching my son's 6-and-under game when a grounder rolls into the infield.
All six kids abandon their positions and sprint toward the ball like it's the only thing that matters. 🧵
November 21, 2025 at 2:15 PM
Six kids. One baseball. Pure chaos.
I'm watching my son's 6-and-under game when a grounder rolls into the infield.
All six kids abandon their positions and sprint toward the ball like it's the only thing that matters. 🧵
I'm watching my son's 6-and-under game when a grounder rolls into the infield.
All six kids abandon their positions and sprint toward the ball like it's the only thing that matters. 🧵
I had a great engineer quit with two weeks' notice.
Exit interview: "I've been struggling for three months. You never asked." 🧵
Exit interview: "I've been struggling for three months. You never asked." 🧵
November 20, 2025 at 2:47 PM
I had a great engineer quit with two weeks' notice.
Exit interview: "I've been struggling for three months. You never asked." 🧵
Exit interview: "I've been struggling for three months. You never asked." 🧵
I quit.
Two different managers.
Same conversation. Two different reactions.
One ruined the relationship forever. One made it stronger.
Manager A (let's call them Steve):
"I've accepted another role."
Five seconds of silence.
"After everything we invested in you?" 🧵
Two different managers.
Same conversation. Two different reactions.
One ruined the relationship forever. One made it stronger.
Manager A (let's call them Steve):
"I've accepted another role."
Five seconds of silence.
"After everything we invested in you?" 🧵
November 19, 2025 at 3:20 PM
I quit.
Two different managers.
Same conversation. Two different reactions.
One ruined the relationship forever. One made it stronger.
Manager A (let's call them Steve):
"I've accepted another role."
Five seconds of silence.
"After everything we invested in you?" 🧵
Two different managers.
Same conversation. Two different reactions.
One ruined the relationship forever. One made it stronger.
Manager A (let's call them Steve):
"I've accepted another role."
Five seconds of silence.
"After everything we invested in you?" 🧵
A former colleague texted me last week: "Remember when I turned down that role three years ago because I didn't feel ready?"
I did remember. VP position. Startup scaling fast. 20% pay bump. She said no because her current company felt "safe." 🧵
I did remember. VP position. Startup scaling fast. 20% pay bump. She said no because her current company felt "safe." 🧵
November 17, 2025 at 3:02 PM
A former colleague texted me last week: "Remember when I turned down that role three years ago because I didn't feel ready?"
I did remember. VP position. Startup scaling fast. 20% pay bump. She said no because her current company felt "safe." 🧵
I did remember. VP position. Startup scaling fast. 20% pay bump. She said no because her current company felt "safe." 🧵
Three junior engineers asked me the same question recently: "Should I be worried AI is going to take my job?"
The panic in their voices wasn't about technology.
It was about the hype machine.
Here's what I told them, and what every tech leader needs to hear: 🧵
The panic in their voices wasn't about technology.
It was about the hype machine.
Here's what I told them, and what every tech leader needs to hear: 🧵
November 14, 2025 at 3:32 PM
Three junior engineers asked me the same question recently: "Should I be worried AI is going to take my job?"
The panic in their voices wasn't about technology.
It was about the hype machine.
Here's what I told them, and what every tech leader needs to hear: 🧵
The panic in their voices wasn't about technology.
It was about the hype machine.
Here's what I told them, and what every tech leader needs to hear: 🧵
A CEO asked me: "How do we keep our remaining teams loyal after the layoffs?"
I stared at him.
"You just cut 10% of their friends to hit quarterly numbers. And now you want loyalty?"
Here's the math: 🧵
I stared at him.
"You just cut 10% of their friends to hit quarterly numbers. And now you want loyalty?"
Here's the math: 🧵
November 13, 2025 at 2:50 PM
A CEO asked me: "How do we keep our remaining teams loyal after the layoffs?"
I stared at him.
"You just cut 10% of their friends to hit quarterly numbers. And now you want loyalty?"
Here's the math: 🧵
I stared at him.
"You just cut 10% of their friends to hit quarterly numbers. And now you want loyalty?"
Here's the math: 🧵
A VP of Engineering told me a few months ago: "I'm thinking about quitting leadership and going back to being a senior engineer."
Fifteen years of experience. Ready to walk away.
Not because he was failing. Because he couldn't see himself succeeding anymore. 🧵
Fifteen years of experience. Ready to walk away.
Not because he was failing. Because he couldn't see himself succeeding anymore. 🧵
November 12, 2025 at 2:53 PM
A VP of Engineering told me a few months ago: "I'm thinking about quitting leadership and going back to being a senior engineer."
Fifteen years of experience. Ready to walk away.
Not because he was failing. Because he couldn't see himself succeeding anymore. 🧵
Fifteen years of experience. Ready to walk away.
Not because he was failing. Because he couldn't see himself succeeding anymore. 🧵
Being easy to work with costs nothing.
But it's the difference between being seen as a technical resource and trusted as a strategic partner.
I watched a technically brilliant CTO get passed over for a board seat. Not because he couldn't architect systems. 🧵
But it's the difference between being seen as a technical resource and trusted as a strategic partner.
I watched a technically brilliant CTO get passed over for a board seat. Not because he couldn't architect systems. 🧵
November 11, 2025 at 4:37 PM
Being easy to work with costs nothing.
But it's the difference between being seen as a technical resource and trusted as a strategic partner.
I watched a technically brilliant CTO get passed over for a board seat. Not because he couldn't architect systems. 🧵
But it's the difference between being seen as a technical resource and trusted as a strategic partner.
I watched a technically brilliant CTO get passed over for a board seat. Not because he couldn't architect systems. 🧵
I watched the best CTO I knew lose three senior engineers in six months.
Not because he was bad at technology. Because he was too good at it.
Here's what happened:
Production outage. Database corruption. Critical customer data at risk. 🧵
Not because he was bad at technology. Because he was too good at it.
Here's what happened:
Production outage. Database corruption. Critical customer data at risk. 🧵
November 10, 2025 at 3:02 PM
I watched the best CTO I knew lose three senior engineers in six months.
Not because he was bad at technology. Because he was too good at it.
Here's what happened:
Production outage. Database corruption. Critical customer data at risk. 🧵
Not because he was bad at technology. Because he was too good at it.
Here's what happened:
Production outage. Database corruption. Critical customer data at risk. 🧵
A CEO once asked me: "How do you stay so confident when you don't know the answer?"
I'd just told him "I have no idea if this migration will work."
He looked confused. "Then why are you recommending it?"
Here's what I learned about confidence: 🧵
I'd just told him "I have no idea if this migration will work."
He looked confused. "Then why are you recommending it?"
Here's what I learned about confidence: 🧵
November 7, 2025 at 3:06 PM
A CEO once asked me: "How do you stay so confident when you don't know the answer?"
I'd just told him "I have no idea if this migration will work."
He looked confused. "Then why are you recommending it?"
Here's what I learned about confidence: 🧵
I'd just told him "I have no idea if this migration will work."
He looked confused. "Then why are you recommending it?"
Here's what I learned about confidence: 🧵
I watched a VP of Engineering clean out his office last month.
Twenty-three years. Three platform migrations. Built a 40-person team from nothing.
Gone in a "restructuring."
Packing up awards and family photos, he kept saying: "I don't know who I am without this place." 🧵
Twenty-three years. Three platform migrations. Built a 40-person team from nothing.
Gone in a "restructuring."
Packing up awards and family photos, he kept saying: "I don't know who I am without this place." 🧵
November 4, 2025 at 12:08 AM
I watched a VP of Engineering clean out his office last month.
Twenty-three years. Three platform migrations. Built a 40-person team from nothing.
Gone in a "restructuring."
Packing up awards and family photos, he kept saying: "I don't know who I am without this place." 🧵
Twenty-three years. Three platform migrations. Built a 40-person team from nothing.
Gone in a "restructuring."
Packing up awards and family photos, he kept saying: "I don't know who I am without this place." 🧵
My friend Eric turned down a conference speaking slot.
Not because he was busy. Because he "wasn't expert enough."
Here's what happened: 🧵
Not because he was busy. Because he "wasn't expert enough."
Here's what happened: 🧵
November 1, 2025 at 3:04 PM
My friend Eric turned down a conference speaking slot.
Not because he was busy. Because he "wasn't expert enough."
Here's what happened: 🧵
Not because he was busy. Because he "wasn't expert enough."
Here's what happened: 🧵
I spent three weeks preparing a technical deep-dive for the board.
Seventy-three slides. Performance benchmarks. Architecture diagrams. ROI models.
Rehearsed it twelve times.
Got through slide four before the CEO stopped me. 🧵
Seventy-three slides. Performance benchmarks. Architecture diagrams. ROI models.
Rehearsed it twelve times.
Got through slide four before the CEO stopped me. 🧵
October 31, 2025 at 2:08 PM
I spent three weeks preparing a technical deep-dive for the board.
Seventy-three slides. Performance benchmarks. Architecture diagrams. ROI models.
Rehearsed it twelve times.
Got through slide four before the CEO stopped me. 🧵
Seventy-three slides. Performance benchmarks. Architecture diagrams. ROI models.
Rehearsed it twelve times.
Got through slide four before the CEO stopped me. 🧵
I quit because of a Tuesday morning meeting.
Not the job. The manager.
Here's what happened: 🧵
Not the job. The manager.
Here's what happened: 🧵
October 30, 2025 at 1:38 PM
I quit because of a Tuesday morning meeting.
Not the job. The manager.
Here's what happened: 🧵
Not the job. The manager.
Here's what happened: 🧵
I watched a senior architect panic when our CTO said "We're moving off React."
This guy had spent five years mastering React. Spoke at conferences about it. Built his entire reputation on it.
"My skills are obsolete now," he told me.
Here's what I told him: 🧵
This guy had spent five years mastering React. Spoke at conferences about it. Built his entire reputation on it.
"My skills are obsolete now," he told me.
Here's what I told him: 🧵
October 29, 2025 at 1:36 PM
I watched a senior architect panic when our CTO said "We're moving off React."
This guy had spent five years mastering React. Spoke at conferences about it. Built his entire reputation on it.
"My skills are obsolete now," he told me.
Here's what I told him: 🧵
This guy had spent five years mastering React. Spoke at conferences about it. Built his entire reputation on it.
"My skills are obsolete now," he told me.
Here's what I told him: 🧵
All hands meeting. CEO mid-presentation. Forty slides deep.
"Our customer retention is at 94%."
From the back of the room, barely audible: "Actually... it's 87%."
Everyone turned. It was Matthew. Three weeks into their internship.
You could hear the room stop breathing. 🧵
"Our customer retention is at 94%."
From the back of the room, barely audible: "Actually... it's 87%."
Everyone turned. It was Matthew. Three weeks into their internship.
You could hear the room stop breathing. 🧵
October 28, 2025 at 2:43 PM
All hands meeting. CEO mid-presentation. Forty slides deep.
"Our customer retention is at 94%."
From the back of the room, barely audible: "Actually... it's 87%."
Everyone turned. It was Matthew. Three weeks into their internship.
You could hear the room stop breathing. 🧵
"Our customer retention is at 94%."
From the back of the room, barely audible: "Actually... it's 87%."
Everyone turned. It was Matthew. Three weeks into their internship.
You could hear the room stop breathing. 🧵
Your $400K platform upgrade has been “85% complete” for nine months.
Everyone’s exhausted. The vendor’s confused. Your team stopped showing up to status meetings.
Sound familiar? 🧵
Everyone’s exhausted. The vendor’s confused. Your team stopped showing up to status meetings.
Sound familiar? 🧵
October 27, 2025 at 1:41 PM
Your $400K platform upgrade has been “85% complete” for nine months.
Everyone’s exhausted. The vendor’s confused. Your team stopped showing up to status meetings.
Sound familiar? 🧵
Everyone’s exhausted. The vendor’s confused. Your team stopped showing up to status meetings.
Sound familiar? 🧵
A consultant pitched us a $1.2M "digital transformation."
Beautiful deck. Bold promises. Timeline: 18 months.
My newest engineer, three months on the job, raised his hand in the pitch meeting. 🧵
Beautiful deck. Bold promises. Timeline: 18 months.
My newest engineer, three months on the job, raised his hand in the pitch meeting. 🧵
October 24, 2025 at 2:20 PM
A consultant pitched us a $1.2M "digital transformation."
Beautiful deck. Bold promises. Timeline: 18 months.
My newest engineer, three months on the job, raised his hand in the pitch meeting. 🧵
Beautiful deck. Bold promises. Timeline: 18 months.
My newest engineer, three months on the job, raised his hand in the pitch meeting. 🧵
I thought my architect was lazy.
Three months. Every project. Same pattern: Brilliant ideas in planning. Mediocre execution. Deadlines missed.
"Just not driven enough," I thought to myself.
Then I overheard him talking to another engineer. 🧵
Three months. Every project. Same pattern: Brilliant ideas in planning. Mediocre execution. Deadlines missed.
"Just not driven enough," I thought to myself.
Then I overheard him talking to another engineer. 🧵
October 23, 2025 at 2:04 PM
I thought my architect was lazy.
Three months. Every project. Same pattern: Brilliant ideas in planning. Mediocre execution. Deadlines missed.
"Just not driven enough," I thought to myself.
Then I overheard him talking to another engineer. 🧵
Three months. Every project. Same pattern: Brilliant ideas in planning. Mediocre execution. Deadlines missed.
"Just not driven enough," I thought to myself.
Then I overheard him talking to another engineer. 🧵
Black Friday. API throwing 500 errors. Revenue dropping $8K per minute.
The CTO panicked. 🧵
The CTO panicked. 🧵
October 22, 2025 at 2:31 PM
Black Friday. API throwing 500 errors. Revenue dropping $8K per minute.
The CTO panicked. 🧵
The CTO panicked. 🧵
Sarah told me she wasn't qualified to lead our platform rebuild.
I looked at her resume. Five years. Dozens of shipped features. Solved problems that made senior engineers quit.
"You're joking, right?" 🧵
I looked at her resume. Five years. Dozens of shipped features. Solved problems that made senior engineers quit.
"You're joking, right?" 🧵
October 20, 2025 at 2:03 PM
Sarah told me she wasn't qualified to lead our platform rebuild.
I looked at her resume. Five years. Dozens of shipped features. Solved problems that made senior engineers quit.
"You're joking, right?" 🧵
I looked at her resume. Five years. Dozens of shipped features. Solved problems that made senior engineers quit.
"You're joking, right?" 🧵
I've disagreed with my boss 47 times in three years.
Never once got fired. Usually got my way.
Here's how: 🧵
Never once got fired. Usually got my way.
Here's how: 🧵
October 17, 2025 at 1:03 PM
I've disagreed with my boss 47 times in three years.
Never once got fired. Usually got my way.
Here's how: 🧵
Never once got fired. Usually got my way.
Here's how: 🧵
The most successful tech leaders I know can't code worth a damn.
I'm serious. 🧵
I'm serious. 🧵
October 16, 2025 at 2:28 PM
The most successful tech leaders I know can't code worth a damn.
I'm serious. 🧵
I'm serious. 🧵