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
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. 🧵
When the Smartest Person in the Room IS the Problem
open.substack.com/pub/prokenne...
open.substack.com/pub/prokenne...
When the Smartest Person in the Room IS the Problem
I watched one of the best CTOs I knew lose three senior engineers in six months.
open.substack.com
November 10, 2025 at 3:02 PM
When the Smartest Person in the Room IS the Problem
open.substack.com/pub/prokenne...
open.substack.com/pub/prokenne...
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: 🧵
The number of senior roles aligned with the CIO is growing. CIOs in SMEs still consolidate responsibilities, but in larger businesses, the separation of roles is more defined, putting greater responsibility on CIOs to orchestrate collaboration. www.cio.com/article/4075...
The more corporate IT leaders, the greater the need to coexist
CTO, CISO, CDO, CAIO — the number of senior roles aligned with the CIO is growing. CIOs in SMEs still consolidate responsibilities, but in larger businesses, the separation of roles is more defined, p...
www.cio.com
October 31, 2025 at 8:18 PM
The number of senior roles aligned with the CIO is growing. CIOs in SMEs still consolidate responsibilities, but in larger businesses, the separation of roles is more defined, putting greater responsibility on CIOs to orchestrate collaboration. www.cio.com/article/4075...
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. 🧵
From developing meaningful business relationships to establishing cultures of continuous learning, CIOs must recast IT’s missions and objectives to help fuel transformational AI success. www.cio.com/article/4064...
What world-class IT looks like in the gen AI era
From developing meaningful business relationships to establishing cultures of continuous learning, CIOs must recast IT’s missions and objectives to help fuel transformational AI success.
www.cio.com
October 23, 2025 at 3:23 PM
From developing meaningful business relationships to establishing cultures of continuous learning, CIOs must recast IT’s missions and objectives to help fuel transformational AI success. www.cio.com/article/4064...
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: 🧵
Everyone wants to write something worth reading.
Fewer do something worth writing about.
Some dare to live the dream they’ve been dreaming.
One becomes their truth in spite of their doubt.
Fewer do something worth writing about.
Some dare to live the dream they’ve been dreaming.
One becomes their truth in spite of their doubt.
October 17, 2025 at 2:40 AM
Everyone wants to write something worth reading.
Fewer do something worth writing about.
Some dare to live the dream they’ve been dreaming.
One becomes their truth in spite of their doubt.
Fewer do something worth writing about.
Some dare to live the dream they’ve been dreaming.
One becomes their truth in spite of their doubt.
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. 🧵
The 52-year-old architect saved our platform rebuild.
My leadership team wanted a "digital native." Someone who "gets modern tech."
I pushed back. Hard.
They thought I'd lost my mind. 🧵
My leadership team wanted a "digital native." Someone who "gets modern tech."
I pushed back. Hard.
They thought I'd lost my mind. 🧵
October 15, 2025 at 2:01 PM
The 52-year-old architect saved our platform rebuild.
My leadership team wanted a "digital native." Someone who "gets modern tech."
I pushed back. Hard.
They thought I'd lost my mind. 🧵
My leadership team wanted a "digital native." Someone who "gets modern tech."
I pushed back. Hard.
They thought I'd lost my mind. 🧵
Trust in technical leadership isn’t built on GitHub commits; it’s built on kept promises.
$40M cloud migration. Three months behind.
Standups turned into one-word answers. Side chats died when I walked by. Code reviews felt like negotiations.
Then I found the Slack channel. 🧵
$40M cloud migration. Three months behind.
Standups turned into one-word answers. Side chats died when I walked by. Code reviews felt like negotiations.
Then I found the Slack channel. 🧵
October 14, 2025 at 1:44 PM
Trust in technical leadership isn’t built on GitHub commits; it’s built on kept promises.
$40M cloud migration. Three months behind.
Standups turned into one-word answers. Side chats died when I walked by. Code reviews felt like negotiations.
Then I found the Slack channel. 🧵
$40M cloud migration. Three months behind.
Standups turned into one-word answers. Side chats died when I walked by. Code reviews felt like negotiations.
Then I found the Slack channel. 🧵
I got invited to speak at a major tech conference.
My first thought? "They definitely meant to email someone else."
For 6 weeks, I was convinced the conference organizers had made a mistake. 🧵
My first thought? "They definitely meant to email someone else."
For 6 weeks, I was convinced the conference organizers had made a mistake. 🧵
October 6, 2025 at 1:32 PM
I got invited to speak at a major tech conference.
My first thought? "They definitely meant to email someone else."
For 6 weeks, I was convinced the conference organizers had made a mistake. 🧵
My first thought? "They definitely meant to email someone else."
For 6 weeks, I was convinced the conference organizers had made a mistake. 🧵
AI analyzed our $50M digital transformation plan in 90 seconds.
It took my team 6 weeks to do the same work.
After decades years leading enterprise transformations, I felt complete vertigo. 🧵
It took my team 6 weeks to do the same work.
After decades years leading enterprise transformations, I felt complete vertigo. 🧵
October 3, 2025 at 6:29 PM
AI analyzed our $50M digital transformation plan in 90 seconds.
It took my team 6 weeks to do the same work.
After decades years leading enterprise transformations, I felt complete vertigo. 🧵
It took my team 6 weeks to do the same work.
After decades years leading enterprise transformations, I felt complete vertigo. 🧵