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
What technical decision did you make that seemed "too expensive" until it prevented a disaster?
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November 25, 2025 at 2:57 PM
What technical decision did you make that seemed "too expensive" until it prevented a disaster?
♻️ Repost and comment if you found this valuable
➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more on leading technology teams without losing your mind in the process.
♻️ Repost and comment if you found this valuable
➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more on leading technology teams without losing your mind in the process.
They know the difference between being wrong and being misunderstood.
Your technical judgment isn't determined by whether executives understand it.
It's proven by systems that work when they're supposed to.
Your technical judgment isn't determined by whether executives understand it.
It's proven by systems that work when they're supposed to.
November 25, 2025 at 2:57 PM
They know the difference between being wrong and being misunderstood.
Your technical judgment isn't determined by whether executives understand it.
It's proven by systems that work when they're supposed to.
Your technical judgment isn't determined by whether executives understand it.
It's proven by systems that work when they're supposed to.
You're not bad at business. They're bad at understanding that technology is their business.
The strongest tech leaders I know:
They stopped letting dismissal become self-doubt.
They trust their expertise even when it's not validated by people who can't evaluate it.
The strongest tech leaders I know:
They stopped letting dismissal become self-doubt.
They trust their expertise even when it's not validated by people who can't evaluate it.
November 25, 2025 at 2:57 PM
You're not bad at business. They're bad at understanding that technology is their business.
The strongest tech leaders I know:
They stopped letting dismissal become self-doubt.
They trust their expertise even when it's not validated by people who can't evaluate it.
The strongest tech leaders I know:
They stopped letting dismissal become self-doubt.
They trust their expertise even when it's not validated by people who can't evaluate it.
The truth most technical leaders need to hear:
You're not too technical. They're too scared to admit they're lost.
You're not overcomplicating it. They're oversimplifying what they don't understand.
You're not too technical. They're too scared to admit they're lost.
You're not overcomplicating it. They're oversimplifying what they don't understand.
November 25, 2025 at 2:57 PM
The truth most technical leaders need to hear:
You're not too technical. They're too scared to admit they're lost.
You're not overcomplicating it. They're oversimplifying what they don't understand.
You're not too technical. They're too scared to admit they're lost.
You're not overcomplicating it. They're oversimplifying what they don't understand.
Document everything. When the thing you warned about happens, your Slack message from six months ago becomes very valuable.
Find allies who understand. One CTO or technical board member who gets it is worth ten executives who don't.
Find allies who understand. One CTO or technical board member who gets it is worth ten executives who don't.
November 25, 2025 at 2:57 PM
Document everything. When the thing you warned about happens, your Slack message from six months ago becomes very valuable.
Find allies who understand. One CTO or technical board member who gets it is worth ten executives who don't.
Find allies who understand. One CTO or technical board member who gets it is worth ten executives who don't.
What actually works:
Translate without dumbing down. "This infrastructure investment prevents the outage that costs us $200K in lost revenue per hour."
Pick your battles. Not every dismissal needs a defense. Some people just need to feel smart.
Translate without dumbing down. "This infrastructure investment prevents the outage that costs us $200K in lost revenue per hour."
Pick your battles. Not every dismissal needs a defense. Some people just need to feel smart.
November 25, 2025 at 2:57 PM
What actually works:
Translate without dumbing down. "This infrastructure investment prevents the outage that costs us $200K in lost revenue per hour."
Pick your battles. Not every dismissal needs a defense. Some people just need to feel smart.
Translate without dumbing down. "This infrastructure investment prevents the outage that costs us $200K in lost revenue per hour."
Pick your battles. Not every dismissal needs a defense. Some people just need to feel smart.
The shift:
I measure my value by systems that don't break. Teams that grow. Problems that stay solved.
Not by whether the CFO understands why we can't "just use WordPress."
I measure my value by systems that don't break. Teams that grow. Problems that stay solved.
Not by whether the CFO understands why we can't "just use WordPress."
November 25, 2025 at 2:57 PM
The shift:
I measure my value by systems that don't break. Teams that grow. Problems that stay solved.
Not by whether the CFO understands why we can't "just use WordPress."
I measure my value by systems that don't break. Teams that grow. Problems that stay solved.
Not by whether the CFO understands why we can't "just use WordPress."
And still get questioned by someone who thinks servers are magic boxes that live in "the cloud."
Their confusion reveals nothing about your judgment. Everything about their comfort with not knowing.
Their confusion reveals nothing about your judgment. Everything about their comfort with not knowing.
November 25, 2025 at 2:57 PM
And still get questioned by someone who thinks servers are magic boxes that live in "the cloud."
Their confusion reveals nothing about your judgment. Everything about their comfort with not knowing.
Their confusion reveals nothing about your judgment. Everything about their comfort with not knowing.
You're living in that gap. They're denying it exists.
Here's what changed for me:
I stopped chasing validation from people who can't evaluate the work.
You can build perfect architecture. Document every edge case. Present bulletproof ROI.
Here's what changed for me:
I stopped chasing validation from people who can't evaluate the work.
You can build perfect architecture. Document every edge case. Present bulletproof ROI.
November 25, 2025 at 2:57 PM
You're living in that gap. They're denying it exists.
Here's what changed for me:
I stopped chasing validation from people who can't evaluate the work.
You can build perfect architecture. Document every edge case. Present bulletproof ROI.
Here's what changed for me:
I stopped chasing validation from people who can't evaluate the work.
You can build perfect architecture. Document every edge case. Present bulletproof ROI.
The logic only works until it catastrophically doesn't.
But invisible risks are terrifying. So, they pretend they're not real.
None of this is about you.
It's about the terrifying gap between what they understand and what their business depends on.
But invisible risks are terrifying. So, they pretend they're not real.
None of this is about you.
It's about the terrifying gap between what they understand and what their business depends on.
November 25, 2025 at 2:57 PM
The logic only works until it catastrophically doesn't.
But invisible risks are terrifying. So, they pretend they're not real.
None of this is about you.
It's about the terrifying gap between what they understand and what their business depends on.
But invisible risks are terrifying. So, they pretend they're not real.
None of this is about you.
It's about the terrifying gap between what they understand and what their business depends on.
The gap between "weekend app" and "enterprise system" is invisible to them. So, they pretend it doesn't exist.
The VP can't see invisible risks.
"We've never been hacked" is like saying "I've never worn a seatbelt and I'm fine."
The VP can't see invisible risks.
"We've never been hacked" is like saying "I've never worn a seatbelt and I'm fine."
November 25, 2025 at 2:57 PM
The gap between "weekend app" and "enterprise system" is invisible to them. So, they pretend it doesn't exist.
The VP can't see invisible risks.
"We've never been hacked" is like saying "I've never worn a seatbelt and I'm fine."
The VP can't see invisible risks.
"We've never been hacked" is like saying "I've never worn a seatbelt and I'm fine."
They didn't. They just revealed they don't know what infrastructure means.
The CEO can't grasp technical complexity.
So, they shrink it to something familiar. A weekend app project. Something they can visualize.
The CEO can't grasp technical complexity.
So, they shrink it to something familiar. A weekend app project. Something they can visualize.
November 25, 2025 at 2:57 PM
They didn't. They just revealed they don't know what infrastructure means.
The CEO can't grasp technical complexity.
So, they shrink it to something familiar. A weekend app project. Something they can visualize.
The CEO can't grasp technical complexity.
So, they shrink it to something familiar. A weekend app project. Something they can visualize.
The CFO doesn't understand infrastructure scaling.
So, they reduce it to a simple cost problem they can control. "Just use the cloud" makes them feel smart. Like they just solved a complex problem with one obvious insight.
So, they reduce it to a simple cost problem they can control. "Just use the cloud" makes them feel smart. Like they just solved a complex problem with one obvious insight.
November 25, 2025 at 2:57 PM
The CFO doesn't understand infrastructure scaling.
So, they reduce it to a simple cost problem they can control. "Just use the cloud" makes them feel smart. Like they just solved a complex problem with one obvious insight.
So, they reduce it to a simple cost problem they can control. "Just use the cloud" makes them feel smart. Like they just solved a complex problem with one obvious insight.
That voice. It gets loud when smart people treat your expertise like an opinion.
Here's what I learned after many years of this:
When someone dismisses your expertise, they're not judging your competence.
They're managing their own discomfort.
Here's what I learned after many years of this:
When someone dismisses your expertise, they're not judging your competence.
They're managing their own discomfort.
November 25, 2025 at 2:57 PM
That voice. It gets loud when smart people treat your expertise like an opinion.
Here's what I learned after many years of this:
When someone dismisses your expertise, they're not judging your competence.
They're managing their own discomfort.
Here's what I learned after many years of this:
When someone dismisses your expertise, they're not judging your competence.
They're managing their own discomfort.
Again, you don't say it. You just wonder if maybe you're overcomplicating things.
Here's the thought that creeps in:
Maybe I'm being too technical. Maybe I don't understand the business. Maybe they're right and I'm wrong.
Here's the thought that creeps in:
Maybe I'm being too technical. Maybe I don't understand the business. Maybe they're right and I'm wrong.
November 25, 2025 at 2:57 PM
Again, you don't say it. You just wonder if maybe you're overcomplicating things.
Here's the thought that creeps in:
Maybe I'm being too technical. Maybe I don't understand the business. Maybe they're right and I'm wrong.
Here's the thought that creeps in:
Maybe I'm being too technical. Maybe I don't understand the business. Maybe they're right and I'm wrong.
Third meeting, here we go again.
A VP dismisses your security recommendation: "We've never been hacked before. Why start spending money on problems we don't have?"
The reason you've never been hacked is because you've been lucky and small. You're about to be neither.
A VP dismisses your security recommendation: "We've never been hacked before. Why start spending money on problems we don't have?"
The reason you've never been hacked is because you've been lucky and small. You're about to be neither.
November 25, 2025 at 2:57 PM
Third meeting, here we go again.
A VP dismisses your security recommendation: "We've never been hacked before. Why start spending money on problems we don't have?"
The reason you've never been hacked is because you've been lucky and small. You're about to be neither.
A VP dismisses your security recommendation: "We've never been hacked before. Why start spending money on problems we don't have?"
The reason you've never been hacked is because you've been lucky and small. You're about to be neither.
We're rebuilding and inventory management infrastructure that processes $40M annually.
You don't say that. You just feel your credibility evaporating.
You don't say that. You just feel your credibility evaporating.
November 25, 2025 at 2:57 PM
We're rebuilding and inventory management infrastructure that processes $40M annually.
You don't say that. You just feel your credibility evaporating.
You don't say that. You just feel your credibility evaporating.
Different meeting. Same pattern.
The CEO interrupts your project update: "Wait, six months for this? My nephew built an app in a weekend."
Your nephew built a to-do list with no users, no security, and no database.
The CEO interrupts your project update: "Wait, six months for this? My nephew built an app in a weekend."
Your nephew built a to-do list with no users, no security, and no database.
November 25, 2025 at 2:57 PM
Different meeting. Same pattern.
The CEO interrupts your project update: "Wait, six months for this? My nephew built an app in a weekend."
Your nephew built a to-do list with no users, no security, and no database.
The CEO interrupts your project update: "Wait, six months for this? My nephew built an app in a weekend."
Your nephew built a to-do list with no users, no security, and no database.
The depth gets you in the room. The breadth keeps you there.
What skill outside your specialty has made you more valuable?
♻️ Repost and comment if you liked this
➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more on leading technology teams that drive business results.
What skill outside your specialty has made you more valuable?
♻️ Repost and comment if you liked this
➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more on leading technology teams that drive business results.
November 24, 2025 at 2:49 PM
The depth gets you in the room. The breadth keeps you there.
What skill outside your specialty has made you more valuable?
♻️ Repost and comment if you liked this
➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more on leading technology teams that drive business results.
What skill outside your specialty has made you more valuable?
♻️ Repost and comment if you liked this
➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more on leading technology teams that drive business results.
Twenty years ago, my advisor was right. I was unfocused.
Today, that's why companies hire me as a fractional CIO.
Not because I'm the best coder or deepest architect. Because I translate between disciplines. And that translation is what executive teams need.
Today, that's why companies hire me as a fractional CIO.
Not because I'm the best coder or deepest architect. Because I translate between disciplines. And that translation is what executive teams need.
November 24, 2025 at 2:49 PM
Twenty years ago, my advisor was right. I was unfocused.
Today, that's why companies hire me as a fractional CIO.
Not because I'm the best coder or deepest architect. Because I translate between disciplines. And that translation is what executive teams need.
Today, that's why companies hire me as a fractional CIO.
Not because I'm the best coder or deepest architect. Because I translate between disciplines. And that translation is what executive teams need.
The specialists are getting automated. The complete humans are getting promoted.
Not because they know everything. Because they connect things across domains that specialists can't see.
Not because they know everything. Because they connect things across domains that specialists can't see.
November 24, 2025 at 2:49 PM
The specialists are getting automated. The complete humans are getting promoted.
Not because they know everything. Because they connect things across domains that specialists can't see.
Not because they know everything. Because they connect things across domains that specialists can't see.
Financial modeling. Not "this costs X" but "this impacts gross margin by Y."
Organizational psychology. People don't resist change. They resist being changed.
Strategic planning. Technology without strategy is expensive automation.
The pattern I see:
Organizational psychology. People don't resist change. They resist being changed.
Strategic planning. Technology without strategy is expensive automation.
The pattern I see:
November 24, 2025 at 2:49 PM
Financial modeling. Not "this costs X" but "this impacts gross margin by Y."
Organizational psychology. People don't resist change. They resist being changed.
Strategic planning. Technology without strategy is expensive automation.
The pattern I see:
Organizational psychology. People don't resist change. They resist being changed.
Strategic planning. Technology without strategy is expensive automation.
The pattern I see:
I can architect systems. Model how they impact cash flow. And explain both to people who only care about outcomes.
That combination is what companies pay for. Not code. Translation.
Three areas that changed my career:
That combination is what companies pay for. Not code. Translation.
Three areas that changed my career:
November 24, 2025 at 2:49 PM
I can architect systems. Model how they impact cash flow. And explain both to people who only care about outcomes.
That combination is what companies pay for. Not code. Translation.
Three areas that changed my career:
That combination is what companies pay for. Not code. Translation.
Three areas that changed my career:
The people thriving aren't the deepest technical experts anymore. They're the ones who can sit in a board meeting and explain why a six-month infrastructure project matters to customer retention.
The uncomfortable truth:
My "unfocused" education is now my competitive advantage.
The uncomfortable truth:
My "unfocused" education is now my competitive advantage.
November 24, 2025 at 2:49 PM
The people thriving aren't the deepest technical experts anymore. They're the ones who can sit in a board meeting and explain why a six-month infrastructure project matters to customer retention.
The uncomfortable truth:
My "unfocused" education is now my competitive advantage.
The uncomfortable truth:
My "unfocused" education is now my competitive advantage.