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
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➕ Follow me (Phillip R. Kennedy
@prokennedy
) for more on leading tech teams without becoming their bottleneck.
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@prokennedy
) for more on leading tech teams without becoming their bottleneck.
November 10, 2025 at 3:02 PM
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➕ Follow me (Phillip R. Kennedy
@prokennedy
) for more on leading tech teams without becoming their bottleneck.
➕ Follow me (Phillip R. Kennedy
@prokennedy
) for more on leading tech teams without becoming their bottleneck.
Your technical expertise got you the job. But it becomes your ceiling if you can't let go.
What's one technical problem you solved that you should've let someone else own?
What's one technical problem you solved that you should've let someone else own?
November 10, 2025 at 3:02 PM
Your technical expertise got you the job. But it becomes your ceiling if you can't let go.
What's one technical problem you solved that you should've let someone else own?
What's one technical problem you solved that you should've let someone else own?
Stop proving you're still technical. Start proving you can make others technical.
That CTO? Still brilliant. Still codes circles around everyone.
Now leads a team of two. Because the best people left to work for someone who'd let them grow.
That CTO? Still brilliant. Still codes circles around everyone.
Now leads a team of two. Because the best people left to work for someone who'd let them grow.
November 10, 2025 at 3:02 PM
Stop proving you're still technical. Start proving you can make others technical.
That CTO? Still brilliant. Still codes circles around everyone.
Now leads a team of two. Because the best people left to work for someone who'd let them grow.
That CTO? Still brilliant. Still codes circles around everyone.
Now leads a team of two. Because the best people left to work for someone who'd let them grow.
Expertise says: "I can fix this faster."
Leadership says: "How do I help you fix this?"
Expertise hoards the hard problems.
Leadership distributes them strategically.
Expertise creates hero moments.
Leadership builds capable teams.
The shift:
Leadership says: "How do I help you fix this?"
Expertise hoards the hard problems.
Leadership distributes them strategically.
Expertise creates hero moments.
Leadership builds capable teams.
The shift:
November 10, 2025 at 3:02 PM
Expertise says: "I can fix this faster."
Leadership says: "How do I help you fix this?"
Expertise hoards the hard problems.
Leadership distributes them strategically.
Expertise creates hero moments.
Leadership builds capable teams.
The shift:
Leadership says: "How do I help you fix this?"
Expertise hoards the hard problems.
Leadership distributes them strategically.
Expertise creates hero moments.
Leadership builds capable teams.
The shift:
Exit interview: "I can't grow when you solve every hard problem before I get the chance."
That's when I learned:
Being the smartest person in the room is a liability when you're supposed to be leading it.
The difference between expertise and leadership:
That's when I learned:
Being the smartest person in the room is a liability when you're supposed to be leading it.
The difference between expertise and leadership:
November 10, 2025 at 3:02 PM
Exit interview: "I can't grow when you solve every hard problem before I get the chance."
That's when I learned:
Being the smartest person in the room is a liability when you're supposed to be leading it.
The difference between expertise and leadership:
That's when I learned:
Being the smartest person in the room is a liability when you're supposed to be leading it.
The difference between expertise and leadership:
His senior engineer was on it. Diagnosing the issue. Ten minutes from a solution.
The CTO couldn't help himself. Jumped in. Took over. Fixed it in five minutes.
Everyone celebrated the quick save.
Except the senior engineer. Who quit two weeks later.
The CTO couldn't help himself. Jumped in. Took over. Fixed it in five minutes.
Everyone celebrated the quick save.
Except the senior engineer. Who quit two weeks later.
November 10, 2025 at 3:02 PM
His senior engineer was on it. Diagnosing the issue. Ten minutes from a solution.
The CTO couldn't help himself. Jumped in. Took over. Fixed it in five minutes.
Everyone celebrated the quick save.
Except the senior engineer. Who quit two weeks later.
The CTO couldn't help himself. Jumped in. Took over. Fixed it in five minutes.
Everyone celebrated the quick save.
Except the senior engineer. Who quit two weeks later.
What's one time you gained respect by admitting you didn't know something?
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➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more on leading through uncertainty without faking it.
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➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more on leading through uncertainty without faking it.
November 7, 2025 at 3:06 PM
What's one time you gained respect by admitting you didn't know something?
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That's the confidence that builds careers. And teams that follow you into problems nobody's solved before.
November 7, 2025 at 3:06 PM
That's the confidence that builds careers. And teams that follow you into problems nobody's solved before.
And your lack of panic is not because you know all the answers.
You're calm because you trust yourself to figure out what matters, assemble the right people, and make the call that moves everyone forward.
You're calm because you trust yourself to figure out what matters, assemble the right people, and make the call that moves everyone forward.
November 7, 2025 at 3:06 PM
And your lack of panic is not because you know all the answers.
You're calm because you trust yourself to figure out what matters, assemble the right people, and make the call that moves everyone forward.
You're calm because you trust yourself to figure out what matters, assemble the right people, and make the call that moves everyone forward.
The uncomfortable truth:
Your team already knows you don't have all the answers.
Pretending you do doesn't build confidence. It shatters trust.
Real confidence is this:
Production crashes at 2 AM. Your team is looking at you.
Your team already knows you don't have all the answers.
Pretending you do doesn't build confidence. It shatters trust.
Real confidence is this:
Production crashes at 2 AM. Your team is looking at you.
November 7, 2025 at 3:06 PM
The uncomfortable truth:
Your team already knows you don't have all the answers.
Pretending you do doesn't build confidence. It shatters trust.
Real confidence is this:
Production crashes at 2 AM. Your team is looking at you.
Your team already knows you don't have all the answers.
Pretending you do doesn't build confidence. It shatters trust.
Real confidence is this:
Production crashes at 2 AM. Your team is looking at you.
You ask "Does this solve the customer problem?" before "Is this technically elegant?"
You tell your team "I was wrong about the approach" instead of quietly pivoting and hoping nobody notices.
You tell your team "I was wrong about the approach" instead of quietly pivoting and hoping nobody notices.
November 7, 2025 at 3:06 PM
You ask "Does this solve the customer problem?" before "Is this technically elegant?"
You tell your team "I was wrong about the approach" instead of quietly pivoting and hoping nobody notices.
You tell your team "I was wrong about the approach" instead of quietly pivoting and hoping nobody notices.
What that actually looks like:
You say "I don't know, but here's how we find out" instead of nodding along pretending you understand.
You ship decisions with 60% of the data instead of overthinking for two weeks when it's too late.
You say "I don't know, but here's how we find out" instead of nodding along pretending you understand.
You ship decisions with 60% of the data instead of overthinking for two weeks when it's too late.
November 7, 2025 at 3:06 PM
What that actually looks like:
You say "I don't know, but here's how we find out" instead of nodding along pretending you understand.
You ship decisions with 60% of the data instead of overthinking for two weeks when it's too late.
You say "I don't know, but here's how we find out" instead of nodding along pretending you understand.
You ship decisions with 60% of the data instead of overthinking for two weeks when it's too late.
Great leaders treat uncertainty like terrain to navigate.
They don't pretend to know the route. They just trust they can read the map.
The shift:
Stop trying to be the expert on everything. Start being the person who knows how to make progress with incomplete information.
They don't pretend to know the route. They just trust they can read the map.
The shift:
Stop trying to be the expert on everything. Start being the person who knows how to make progress with incomplete information.
November 7, 2025 at 3:06 PM
Great leaders treat uncertainty like terrain to navigate.
They don't pretend to know the route. They just trust they can read the map.
The shift:
Stop trying to be the expert on everything. Start being the person who knows how to make progress with incomplete information.
They don't pretend to know the route. They just trust they can read the map.
The shift:
Stop trying to be the expert on everything. Start being the person who knows how to make progress with incomplete information.
Bad leaders treat uncertainty like a secret to hide.
They memorize buzzwords. Study frameworks. Pretend they understand every technical detail their team mentions.
Then freeze when something breaks that isn't in the playbook.
They memorize buzzwords. Study frameworks. Pretend they understand every technical detail their team mentions.
Then freeze when something breaks that isn't in the playbook.
November 7, 2025 at 3:06 PM
Bad leaders treat uncertainty like a secret to hide.
They memorize buzzwords. Study frameworks. Pretend they understand every technical detail their team mentions.
Then freeze when something breaks that isn't in the playbook.
They memorize buzzwords. Study frameworks. Pretend they understand every technical detail their team mentions.
Then freeze when something breaks that isn't in the playbook.
It's not knowing the answer. It's knowing you can find it.
Think of leadership confidence like jazz improvisation. The best players don't memorize every note. They trust their ability to respond to whatever the other musicians play.
Think of leadership confidence like jazz improvisation. The best players don't memorize every note. They trust their ability to respond to whatever the other musicians play.
November 7, 2025 at 3:06 PM
It's not knowing the answer. It's knowing you can find it.
Think of leadership confidence like jazz improvisation. The best players don't memorize every note. They trust their ability to respond to whatever the other musicians play.
Think of leadership confidence like jazz improvisation. The best players don't memorize every note. They trust their ability to respond to whatever the other musicians play.
What skills have you developed that would make you valuable at any company?
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➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more insights on building tech leadership that outlasts any org chart.
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➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more insights on building tech leadership that outlasts any org chart.
November 4, 2025 at 12:08 AM
What skills have you developed that would make you valuable at any company?
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➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more insights on building tech leadership that outlasts any org chart.
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➕ Follow me (Phillip R. Kennedy @prokennedy.bsky.social ) for more insights on building tech leadership that outlasts any org chart.
Your current role will end someday. That's not pessimistic, it's just true.
The question is: when it does, will you know who you are without it?
The question is: when it does, will you know who you are without it?
November 4, 2025 at 12:08 AM
Your current role will end someday. That's not pessimistic, it's just true.
The question is: when it does, will you know who you are without it?
The question is: when it does, will you know who you are without it?
5) Learn the language of business - The CTOs who survive disruption can translate "our Redis cluster is maxed out" into "we're losing $50K monthly in abandoned transactions."
November 4, 2025 at 12:08 AM
5) Learn the language of business - The CTOs who survive disruption can translate "our Redis cluster is maxed out" into "we're losing $50K monthly in abandoned transactions."
4) Focus on patterns, not just fixes - Anyone can patch a bug. Leaders spot the root cause and prevent it from happening to three other teams.
November 4, 2025 at 12:08 AM
4) Focus on patterns, not just fixes - Anyone can patch a bug. Leaders spot the root cause and prevent it from happening to three other teams.
3) Teach what you know - Every talk you give, every junior dev you mentor, every blog post you write builds your reputation beyond any single company.
November 4, 2025 at 12:08 AM
3) Teach what you know - Every talk you give, every junior dev you mentor, every blog post you write builds your reputation beyond any single company.
2) Build relationships outside your walls - The best opportunities come from people who've seen you in action, not algorithms matching keywords.
November 4, 2025 at 12:08 AM
2) Build relationships outside your walls - The best opportunities come from people who've seen you in action, not algorithms matching keywords.
Stop building a career around a company. Start building capabilities around problems you can solve anywhere.
1) Document your wins with numbers - "Improved performance" means nothing. "Reduced API response time from 2.3s to 400ms, preventing 15% user churn" tells a story.
1) Document your wins with numbers - "Improved performance" means nothing. "Reduced API response time from 2.3s to 400ms, preventing 15% user churn" tells a story.
November 4, 2025 at 12:08 AM
Stop building a career around a company. Start building capabilities around problems you can solve anywhere.
1) Document your wins with numbers - "Improved performance" means nothing. "Reduced API response time from 2.3s to 400ms, preventing 15% user churn" tells a story.
1) Document your wins with numbers - "Improved performance" means nothing. "Reduced API response time from 2.3s to 400ms, preventing 15% user churn" tells a story.