Jerry Macnamara

ProvenChaos

Business is not only the economic engine of the world, but it is also the engine of cultural change. Our mission is to positively impact a healthier, happier world where people live life on their terms, with intention, because of better business. By equipping our CEOs with frameworks to lead and a support system to help, businesses will fulfill the promise to their customers, vendors, and employees.

ProvenChaos. Weird company name, right? 

Let me explain because you’ve probably experienced it yourself.

You’ve Proven there is a pain point you can solve in the market, but you feel in Chaos because your systems, people or processes haven’t kept up. Or, maybe you feel in chaos personally because the business is stealing all your energy and time away from your family, so there is a lack of fulfillment despite your success.

That’s ProvenChaos.

Have you ever had that ProvenChaos feeling? I bet you have.

Learn how we can help at ProvenChaos.com

Founder and CEO

Best Places to Lead Show

Your company has the potential to be great. The leader’s responsibility is to unlock that potential - or doom it to mediocrity.

On the Best Places to Lead show, you’ll learn the hard-fought lessons from the front lines earned by business leaders who have already had their teeth bashed in and lived to tell about it. We’ll share the tips, tricks, mindsets, and frameworks that allow great leaders to lead differently. Register to attend live, ask questions, and level up.

The show airs every Thursday at 3:30 pm ET / 1:30 pm MT.

Host

JerryMacnamara.com

Jerry Macnamara helps businesses and people succeed. He consults to entrepreneurs, business owners and managers about creating value-driven organizations, which deliver results. The goal is to intentionally uncover the Soul of the organization and engineer strategic plans that produce highly accountable environments and deliver results.

Chief Thinker

12 Mavens

Soccer Classroom

Soccer Classroom is dedicated to helping volunteer soccer coaches find fun, inspiring and positive ways to develop youth soccer players. By using a "player-first" mentality, coaches will see the big picture of player development which leads to long-term success on the field.

Soccer Classroom is Jerry's "community service" project. Through this online coaching platform, Soccer Classroom reaches over six thousand fans on Facebook and over half a million coaches and players in countries all over the world. The magnified resulting impact on players and teams is immeasurable.

If you are a business, coach or administrator who can add value to the Soccer Classroom community, we invite you to connect with us.

Creator

McCoy and Company

McCoy and Company (MAC), the commercial arm of North Florida Field Services, Inc., spun out from the parent company in December 2014. Utilizing the same white collar approach to a blue collar business, MAC services Property Managers, Owners and Architects in realizing their construction visions.

NFFS General Contractors

Founded in 2007 by Marti McCoy with $5,000 and a borrowed trailer, NFFS General Contractors has grown to be a leader in the REO home repair, property preservation, maintenance and inspection of residential homes. Headquartered in Jacksonville, Florida with additional offices in Tampa, NFFS completes restoration work across the state of Florida for Banks, Hedge Funds and Equity Funds. The company is a Top 10 Vendor nationally to Fannie Mae.

NFFS was named the Fastest Growing Company in Northeast Florida in 2012 by the Jacksonville Business Journal. The company maintained a three year average annual revenue growth rate of 372%. In 2013, the company earned place #18 on the JBJ list and joined the Inc 500 Fastest Growing Companies list at #8 Construction industry, #15 in Florida and #238 nationally with a four year growth rate of 1,808%. In 2014, the company again was profiled in both the JBJ as a Fast Company (#7 growth, #8 total dollar growth) and Inc. magazine at #904 nationally. (Profile: http://www.inc.com/profile/north-florida-field-services) Florida Trend magazine recognized NFFS as one of the "Best Companies to Work For in Florida" in 2014. (http://www.floridatrend.com/article/17368/best-small-companies)

Jerry's central role is running the business-side of the company: setting the strategic direction, solving the problems of growth while maintaining and expanding profitability. 

In 2013, the Jacksonville Business Journal recognized Jerry an "Ultimate CEO" for leading NFFS through this high-growth cycle as well as his contributions to the community.

In 2014, the Jacksonville Business Journal recognized Jerry as a "40 Under 40" award recipient.

TotallySoccer

Totally Soccer is a leading provider of soccer jerseys, uniforms and field equipment to teams and clubs across the country. The direct from the factory approach makes buying soccer gear easier, cheaper and faster.

Totally Soccer leveraged its infrastructure and systems to smartly branch into other sports to offset seasonality and increase buying power. The company owns and operates a suite of sports websites that sells custom sports uniforms.

President

Jogo

Jogo is a leading producer of team sports apparel throughout North America. To secure his Management Consultant Visa, Jerry was certified as an expert in the US soccer market. In this position, he built systems and procedures to align manufacturing, sales and marketing.

Sales & Marketing Consultant

Soccer Post

Soccer Post is a franchise company specializing in providing soccer equipment to youth and adult teams, clubs and leagues. Jerry helped the organization grow from a single location to expanding the operation to thirty-five stores selling over $15MM across the country. As VP of Operations, Jerry wrote the training manual, opened the stores and interfaced with vendors such as Nike and Adidas. 

Entrepreneur magazine recognized Soccer Post as a Franchise 500 company.

Vice President Operations

Helping CEOs Scale without Stress | Franchise 500 (2x), Inc500 (2x) & Biz Journal Fast 50 (3x) + Trend Best Places to Work | Ultimate CEO | Proving Good Guys Finish 1st since 1974 | Host "Best Places to Lead"

Your business is working, but can it do more?
 
Like most business leaders, you've likely spent sleepless nights obsessing over your company's future. You’ve closed your office door, scratched your head, and wondered what to do next.

You're anxious about losing your best employees while regretting not letting go of underperformers sooner.

Does this sound at all familiar?
Feel Trapped: You lack a clear execution plan and are overwhelmed by daily crises, running from fire to fire.

Employee Frustrations: Miscommunication and unclear directions leave you shouldering the burden alone.

Unmanageable Growth: Scaling your business feels impossible without the right systems and processes.

Fear Over Joy: Constant fear paralyzes and frustrates you, stealing the joy from your work.

It doesn't have to be this way. With a proven track record leading award-winning companies across multiple industries, I’ve developed a system that drives success. 

Here are some of the results I’ve produced:

Franchise Growth: I helped grow a franchise company from $5MM to $15MM in just 18 months, earning a spot in the Franchise 500 (2x).

Manufacturing Excellence: I transformed a forty-year-old manufacturing company to achieve a 98% on-time delivery rate.

Successful Exit: I started, scaled, and successfully sold an internet business.

Construction Leadership: I led a construction company from $7MM to $30MM in three years, making it to the Inc 500 (2x) and Best Places to Work.

Here’s the truth…
Your product doesn’t matter. 
Your service doesn’t matter. 
Your industry doesn’t matter. 
Your channel doesn’t matter. 

Your business is widgets, plain and simple…  and the only thing that matters is your leadership approach.

However, on-the-job training is stressful and costly, eating away at your opportunities and profits.
If you want to scale without stress, join our exclusive mastermind of high-growth B2B CEOs. Learn from my experience and avoid the pitfalls that can derail your progress.

Book a call: https://calendly.com/jerrymacnamara/25-minute-zoom

Fractional CIO & Strategic Advisor | Fixing IT Bottlenecks, Building High-Trust Tech Foundations | Scaled Orgs from $0 to $3B+

Strategic IT Leadership for Growing Companies

Helping non-technical founders and small business leaders scale without getting slowed down by their own systems

The Problem
Most companies don’t fail because they dream too small.
They fail because their technology trips them up before they ever hit full speed.

Systems that don’t talk to each other

Vendors that overpromise and underdeliver

Teams that pull in different directions

Operational chaos hidden behind "we’ll fix it later"

Growth without fundamentals isn't a shortcut—it's a detour. Real business expansion is about building systems that scale with integrity, not just adding layers of complexity to a shaky core.

The Outcome
I help you build a stronger, smarter, simpler technology foundation — one that scales with your business, not against it.

✅ Faster operations
✅ Smarter use of tools and teams
✅ Fewer expensive mistakes
✅ A clear, flexible roadmap for growth
✅ More time spent leading — less time fighting fires

My Approach
I’m not here to sell you systems you don’t need or waste months writing strategy decks nobody reads.

I’m here to help you:

Fix what’s broken (before it costs you real money)

Align your people, process, and platforms (so they work together, not against each other)

Build momentum you can actually feel (and measure in real-world results)

I bring 30 years of hands-on experience building and scaling IT in organizations that grew from to over $3B — many times as the very first IT hire, often leading global distributed teams.

What you get is simple:
Real strategy. Real execution. Real growth.

No bloat. No buzzwords. No bureaucratic nonsense.

Services
Fractional CIO Leadership
Part-time executive leadership to align your tech and business strategy, manage vendors, and build internal capabilities without hiring a full-time CIO.

Project Rescue and Turnaround
When critical projects stall, I step in to realign teams, simplify the chaos, and deliver results.

Vendor and System Sourcing
Find the right systems and partners that fit your business — not someone else’s template.

Strategic IT Roadmapping
Clear, practical roadmaps that connect today’s actions to tomorrow’s growth.

Who I Work Best With
Founders and business leaders who:

Are serious about scaling

Know tech is crucial but don’t want to live inside it

Value momentum over perfection

Want a partner who talks business, not just tech

Ready to Clear the Bottlenecks and Build What's Next?
Let's start with a simple conversation.
No sales pitch. Just clarity on where you are — and what’s possible next.

Phillip R. Kennedy

They sat in architecture meetings, silent, watching me design their systems.

I thought I was helping.

Three years into my VP of Engineering role, I was solving every hard problem myself. Reviewing every architectural decision. Jumping into every code review with a better approach.

We shipped on time. Systems stayed stable. I was crushing it.

Then I noticed something.

Standups had become status reports. Code reviews had become lectures. Engineers stopped proposing solutions. They'd wait for mine.

One afternoon, I asked a senior engineer what she thought about an integration approach. She shrugged.

"You're going to redesign it anyway. Just tell me what you want."

That landed like a punch.

I wasn't building engineers. I was building dependency.

Every problem I solved was a problem someone else didn't learn to solve. Every decision I made was a decision someone else didn't learn to make. My speed had become their ceiling.

Here's what doesn't get talked about enough in technical leadership:

The skills that got you promoted are the skills you now have to stop using.

You were promoted for solving. Now your job is to stop solving so others can start.

That's not intuitive. Solving feels productive. Stepping back feels like abandoning your team. Your identity is wrapped around being the one who knows.

Letting go of that is harder than any technical problem I've faced.

But here's what changed when I did:

I stopped answering and started asking. "What would you try?" before offering my solution. "Help me understand your approach" before suggesting changes. "Who has thoughts on this?" and then actually waiting through the uncomfortable silence.

The silence is where growth happens. I had to learn to stop filling it.

Six months later, that senior engineer who'd given up on proposing ideas? She architected a system I couldn't have designed myself. Because she'd finally had space to think.

The job went from being the technical oracle to being the person who helps brilliant engineers trust their own judgment.

I build less now. We ship more.

Trust scales better than talent.

I wish someone had told me that three years earlier.

♻️ Repost and comment if you've made this shift

➕ Follow me (Phillip R. Kennedy) for more on leading without being the bottleneck

Fractional CIO & Strategic Advisor | Helping Non-Technical Leaders Make Technical Decisions | Scaled Orgs from $0 to $3B+

The engineer quit for a 20% raise and a bigger title. No hard feelings. Good opportunity.

Three months later he called.

"Quick question. Was it always this chaotic everywhere? Or did something change after I left?"

Nothing had changed. He'd just lost the force field.

His old manager, Rachel, never talked about what she did all day. Her team saw clear priorities. Reasonable timelines. Scope that didn't shapeshift every Thursday.

They assumed that was just how things worked.

It wasn't. Rachel made it look that way.

I grabbed coffee with her and asked what she'd been up to. She scrolled through her calendar like she was reading a casualty report.

Monday: talked sales out of an "emergency" demo that would've derailed the sprint. Tuesday: three hours convincing the CPO that the "simple" feature was a six-week rebuild. Wednesday: absorbing a rant from the CEO about competitors, translating it into one backlog line item. Thursday: killing a meeting series that had grown to eleven attendees and no purpose.

"What about actual engineering leadership?" I asked.

She looked at me like I'd missed the point.

"That was the engineering leadership."

Her team built things. She built the space for them to build things. Different jobs. Only one shows up in LinkedIn posts.

The engineer who left? He landed somewhere with a manager who did the LinkedIn version of leadership. Lots of mentorship. Skip-levels. Retrospectives.

Zero air cover.

Within a month, scope changed constantly. Six standing meetings. Half his time explaining why things take time.

Same engineer. Suddenly felt like he'd gotten worse at his job.

He hadn't. He just lost something he never knew he had.

Your team can handle hard problems. That's why you hired them.

They can't handle hard problems while also fighting the organization. The context-switching alone kills them.

So you have a choice. Let the chaos through and watch your team drown in it. Or absorb it yourself and let them do the work you're paying them to do.

Rachel chose absorption. Her calendar was a disaster so her team's calendars didn't have to be.

They never thanked her for it. Didn't know there was anything to thank her for.

That's the job.

The engineer eventually figured it out. Took him about six months of chaos to realize what he'd lost.

"I thought good companies just had clear priorities," he told me.

"Some do," I said. "Most don't. You just had Rachel."

Some things are worth more than titles.

♻️ Repost and comment if you've lost a leader and suddenly realized what they'd been blocking 

➕ Follow me (Phillip R. Kennedy) for more on leadership that never makes LinkedIn

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.

Not her technical skills. Not her architecture decisions. Not the systems she'd built.

He told me about a 3 AM incident.

His son's first travel baseball tournament was that Saturday. Months of early morning practices. The kid had finally made the starting lineup. Dad had promised he'd be there.

Thursday night, 2 AM, production went down. Major outage. All hands situation.

He was halfway through his second Red Bull when the VP showed up in the incident channel.

"I've got this. Go home. Get some sleep. Be at that game."

He pushed back. Felt guilty. The system was still down.

She wasn't having it.

"I've handled worse. Your son is nine once. Go."

He went. Slept four hours. Made the game. Watched his kid get his first hit.

The VP handled the incident herself. Twelve hours of firefighting. She mentioned it once the following Monday, almost in passing. No guilt trip. No scorecard. Just "we got it fixed, here's what we learned."

That was eight years ago. He's worked at three companies since.

He still tells that story.

Not the deployment metrics from that quarter. Not the sprint velocity. Not the uptime percentage.

The 3 AM moment when someone chose his family over a dashboard.

Here's what I've learned watching technical leaders for twenty years:

The metrics fade. The moments stay.

I've seen leaders with perfect delivery records whose teams couldn't wait to leave. I've seen leaders with messy quarters whose engineers followed them to their next three companies.

The difference was never the dashboards.

It was whether they shielded their team from chaos that wasn't theirs to carry. Whether they fought for the refactoring time that product wanted to skip. Whether they backed their engineers' judgment when an executive questioned a decision. 

Whether they remembered that the people writing the code had lives outside the code.

The VP my candidate talked about? She probably doesn't remember that night. One incident among hundreds.

He'll remember it forever.

That's the thing about technical leadership. You rarely know which moments matter until someone tells you years later.

A decade from now, nobody will remember your sprint velocity.

They'll remember whether you treated them like resources to optimize or people worth protecting.

The candidate took the job.

He's still there. Four years later.

Still telling that story about the VP and the baseball game.

Be the leader they mention at their next three companies.

The one who showed them what leadership looks like when nobody's measuring.

♻️ Repost and comment if you remember a leader who showed up when it mattered

➕ Follow me (Phillip R. Kennedy) for more on technical leadership that outlasts the metrics

He took the blame for a deployment failure he didn't cause.

A junior engineer had pushed a config change that brought down production. The VP of Engineering knew exactly what happened. So did the team. So did the executives demanding answers.

In the incident review, he said: "This was a process failure. I should have caught it. Here's what I'm changing."

He never named the engineer.

That engineer is now a Staff Developer. She's told me that moment changed how she leads her own team.

That's invisible leadership. The kind that never shows up on a performance review. The kind that builds something you can't measure but can always feel.

I've watched technical leaders for twenty years. The ones people actually want to follow rarely match the stereotype. They're not the smartest in the room. They're not the ones with the most impressive architecture on their resume.

They're the ones who do these things when no one's watching:

Take the 2 AM page so their team can sleep. Block unrealistic deadlines in rooms their engineers never see. Let someone else present the design they built together. Hire people who might outshine them, then celebrate when those people get recruited away.

If everything goes right, they give away all the credit.

If everything goes wrong, they take the blame.

Sound exhausting? It is. Sound thankless? Often.

So why do it?

Because leadership isn't about you. It's about what happens to the people around you.

The engineer who takes a risk because she knows someone has her back. The team that innovates because failure won't mean humiliation. The culture where people stay not because of stock options, but because they feel seen.

You can't build that with authority. You can only build it with trust. And trust comes from a thousand small moments where you choose the team over yourself.

Here's what I've learned:

The technical leaders who struggle most are the ones still trying to be the smartest person in the room. They were promoted for expertise. They built their identity on knowing the answer.

But leadership isn't about having answers. It's about creating space for others to find them.

That requires letting go. Of credit. Of control. Of being the hero.

It's a harder transition than any technology migration.

Would you still lead if no one ever knew your name?

The answer to that question determines what kind of leader you'll become.

Start small. Take the blame once when it's not your fault. Give credit when it is. Block one unreasonable demand so your team never has to hear about it.

Leadership is a practice, not a position.

It's a choice you make every day.

Make it today.

♻️ Repost and comment if you've worked with someone like this

➕ Follow me (Phillip R. Kennedy) for more on technical leadership that earns trust

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.

We're watching the same movie we watched in 2012. Remember when everyone was suddenly a "social media expert" because they had a Facebook account? Same energy. Different rectangle.

Every resume I see now has AI somewhere. "AI-savvy leader." "Experienced with AI tools." "Passionate about AI."

Cool. So is my brother. He uses ChatGPT to write fishing emails. He's not updating his LinkedIn about it.

Here's the spectrum nobody wants to acknowledge:

AI User: You chat with Claude. Generate images with Midjourney. Use Copilot to debug code. This is digital literacy. It's table stakes. It's being good at Google in 2010. Not a skill. An expectation.

AI Practitioner: You've shipped something. Built a workflow that actually runs in production. Made architectural decisions about which model to use and why. Measured whether it worked. This belongs on your resume.

AI Expert: You build systems. Fine-tune models. Make decisions other engineers depend on. People pay you for your judgment, not your prompts. This is an identity, not a bullet point.

Most people are users cosplaying as practitioners.

The honest test: Can you explain what you built, how it works, and what business problem it solved?

Not "I use AI daily."
Not "I'm really good at prompting."
Not "I generated our marketing images."

Those are tool usage. I know eleven-year-olds that use AI daily. They're not adding it to their resume.

What actually counts:

"Built an AI chatbot that reduced support tickets 30%."
"Integrated Claude API into our workflow, saving the team fifteen hours weekly."
"Fine-tuned a model for our specific domain because the base model couldn't handle our edge cases."

Specific. Measurable. Actually built.

The hype will settle. It always does.

When it does, the people who shipped things will be hiring the people who talked about shipping things.

Pick which side of that conversation you want to be on.

And maybe take "AI Expert" off your headline if your expertise is typing questions into a chat box.

The hype fades. The work stays.

Make sure you have some.

♻️ Repost and comment if you've interviewed an "AI expert" whose expertise was typing questions

➕ Follow me (Phillip R. Kennedy) for more on building real technical credibility that survives the hype cycle

$640K in engineering time. Launched on time. Under budget. 3% adoption.

Nobody called it a failure because it shipped.

A CTO I work with spent nine months building a customer portal. His team hit every milestone. The all-hands demo got applause. Two months after launch, almost nobody had logged in. Support tickets hadn't moved. Sales couldn't point to a single deal it influenced.

Nine months of building. Solving a problem that didn't exist.

The meeting that started it was eleven months earlier. VP of Sales mentions a competitor has a portal. A few heads nod. Someone says "we should probably have that too."

The CTO asks the right question: "What problem would it solve?"

"Customer self-service. Reduces support load. Makes us look modern."
Sounds reasonable. Gets added to the roadmap. Three weeks later it has a team, a timeline, and enough momentum that stopping feels harder than continuing.

Nobody checked if customers were actually asking for it. Nobody measured real support costs. Nobody pinned down what "look modern" means in revenue.

They built a solution and went looking for the problem afterward.

He told me he felt it around month four. Usage projections kept sliding. Customer interviews were thin. But the project had executive visibility now. Stopping meant explaining why they'd started. Easier to ship and hope adoption would follow.

It didn't.

I've watched this same pattern at six different companies. The projects that quietly drain organizations aren't the dramatic failures. Those get autopsied. Lessons get documented. Someone writes a postmortem.

The real damage comes from the successes that never mattered. They ship, so nobody examines them. They consume capacity, so other things don't get built. They sit on roadmaps as proof the team is "executing" while actual problems go unsolved.

Your job as a technical leader isn't building everything that gets requested. It's protecting your team from building things that don't matter.

That means asking what breaks if you don't build it. Not only what improves. What actually breaks. If the answer is nothing, you're looking at a nice-to-have in a strategy costume.

That means knowing what you're not building when you say yes. That portal cost nine months. Nine months of not fixing the performance issues that drove their largest customer to start evaluating competitors.

Shipping isn't success. Mattering is.

The best technical leaders aren't just the best builders. They're the ones who know which buildings shouldn't be built.

♻️ Repost and comment if you've shipped something successful that shouldn't have existed

➕ Follow me (Phillip R. Kennedy) for more on knowing when not to build

"This is high priority."

I watched a VP send this message to five engineers.

What they heard:

Engineer 1: Drop everything. Do it now.
Engineer 2: Move it up the list. Handle it this week.
Engineer 3: Important, but she says that about everything.
Engineer 4: Add it to the backlog. She'll follow up if it's real.
Engineer 5: Reply "got it" and wait for clarification.

Same message. Five interpretations. One very confused sprint.

"Priority" doesn't mean anything. Neither does "ASAP." Neither does "time-sensitive" or "urgent" or "when you get a chance."

These words feel like communication. They're actually the absence of it.

Here's what happens:

You send "this is urgent" because you're stressed.
They receive "this is urgent" and have to guess what you mean.

Do you mean today? This hour? Before the 3pm meeting? Before end of quarter?

They don't know. So they either panic unnecessarily or ignore it entirely.

Both outcomes are your fault.

A Director I worked with wondered why his team never hit the "right" priorities. I asked him to show me his last ten Slack messages.

"High priority."
"Please prioritize."
"This is time-sensitive."
"Need this ASAP."
"Urgent."

His team had learned that "urgent" meant "he's stressed" not "this actually matters."

So they pattern-matched. Waited to see which "urgent" things he followed up on. Those were the real priorities. The rest was noise.

He'd trained them to ignore him without realizing it.

The fix is almost embarrassingly simple:

Replace "ASAP" with an actual time.

Not: "Need this ASAP." But: "Need this by 3pm today."
Not: "This is a priority." But: "Do this first. Then the API work. Then the backlog items."
Not: "Time-sensitive." But: "If you only do one thing today, do this."

Specific beats urgent every time.

The engineers I respect most do something else too. They name what can wait.

"I need the auth fix by Thursday. The dashboard updates can wait until next sprint."

That single sentence does more than a hundred "ASAP" messages. It tells your team where to focus and where to relax.

Clarity is kindness. Vagueness creates anxiety you never see.

Your team isn't ignoring your priorities.

They just can't read your mind.

Stop making them guess.

♻️ Repost and comment if your Slack is full of "urgent" messages that aren't

➕ Follow me (Phillip R. Kennedy) for more on leading without accidentally training your team to ignore you

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.

I talked to his team. Twenty minutes with a senior engineer and I had the answer.

"We told him this six months ago. He said we'd revisit it later. We stopped bringing it up."

A legacy API broke constantly. Every sprint collapsed when it went down. The team knew. They'd documented it. Raised it in retros. Written it up with estimated fix time.

The VP never heard it. Not really.

Here's what happened:

Engineer mentioned it in a 1:1. VP was distracted by a CEO escalation. Said "let's table that for now."

Engineer heard: "This isn't important."

VP heard himself say: "We'll come back to this."

One conversation. Two completely different memories.

This is how you lose access to what your team knows.

Not through one big dismissal. Through a thousand small moments.

The retro where you checked your phone. The suggestion you said "interesting" to and never mentioned again. The problem you called "technical debt" that turned out to be existential.

Your team is pattern matching. They're always pattern matching.

The pattern says: bringing this up won't change anything.

So they stop. Not dramatically. They just get quieter. Proposals get shorter. Eventually they sit in meetings with answers you need and don't offer them.

They're not hiding information.

They've learned you're not really asking.

The VP fixed the API in three weeks once he finally heard the problem. Three weeks. His team had been drowning for six months.

"I thought I was listening," he told me. "I was just waiting for my turn to talk."

Your team has answers you need. Right now. Today.

The question is whether you've built the kind of silence where they'll actually tell you.

Next 1:1, try this: "What's something you've stopped bringing up because it didn't seem like I was hearing it?"

Then wait. Ten seconds of silence feels like forever.

That's where the truth lives.

♻️ Repost and comment if you've been the engineer waiting to be heard

➕ Follow me (Phillip R. Kennedy) for more on leadership that actually listens

Your resume is about to become a conversation between two AIs.

Neither of them is you.

A friend runs talent acquisition at a mid-sized SaaS company. Last month she told me her team stopped reading resumes. Not reduced. Stopped. An AI screens applications, scores candidates, and surfaces the top fifteen for human review. The humans look at LinkedIn profiles, GitHub contributions, and anything the person has written or built publicly.

The resume is just the ticket to get processed. The decision happens somewhere else.

This is already normal. It's about to be universal.

Think about what's coming. AI writes your resume, optimized for the job description. AI on the other side parses it, looking for keyword matches and pattern fits. Two algorithms having a conversation about you, without you in the room. The most human thing in the process is the six seconds a recruiter spends glancing at your LinkedIn photo.

When both sides of the table are automated, credentials become noise. Everyone's resume will be optimized. Everyone's cover letter will hit the right notes.

So where does differentiation happen?

Before the application.

The VP of Engineering role that went to your former colleague? She didn't apply. The CEO asked his network who they knew, and three people mentioned her name. She'd been writing about engineering leadership for two years. Nothing viral. Just consistent, thoughtful posts about problems she'd actually solved. When the CEO searched for her, he found proof she could think.

That's not luck. That's compounding visibility.

The CTO who landed at that Series B startup? He'd been publishing technical retrospectives on his blog. Ugly website. Maybe 200 readers. But when the founder asked for intros to senior technical leaders, two investors forwarded his writing. He was in the conversation before the job description existed.

Your personal brand is about being in the room when someone asks "who do we know that does this?"

The people who win in this next era won't be the most credentialed. They'll be the most findable. The ones who've built a trail of proof that shows how they think, what they've learned, and what problems they know how to solve.

Starting is simpler than you think.

Pick one problem you've solved in the last six months. Write about what actually happened. Not thought leadership. Not advice. Just the story, the mistake, the thing you learned. Something a peer would read and think "I've been there."

Do that once a week for six months. You'll have more public proof of your thinking than 95% of people at your level.

Your resume gets you processed. Your brand gets you chosen.

The algorithms are coming for the application process. They're not coming for your reputation.

Build the thing they can't automate.

♻️ Repost and comment if you've gotten an opportunity because someone already knew your work

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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.

I pointed this out to a VP of Engineering last year. He'd just shown me his infrastructure. Monitoring for every service. Alerting tuned to catch problems before users noticed. Capacity planning projections through next year.

Beautiful systems.

Then I asked about his career plan.

Long pause. Slight panic.

"I'm kind of figuring it out as I go."

Sir. You have redundancy for a payments service that processes twelve transactions a day. And your career strategy is vibes?

He laughed. Then stopped laughing.

This is everywhere. World-class systems thinkers who apply zero systems thinking to themselves.

You'd never run production without monitoring. Your career has no early warning system.

You'd never ship without a rollback plan. Your career has no redundancy if this role evaporates.

You'd never let a service drift without SLOs. Your own growth has no measurable objectives.

You build alerting for services. Not for yourself.

Here's why: production gives you feedback. Career drift doesn't page you. It just feels like a slow Tuesday. For years.

A Director I know discovered this after a reorg eliminated his role. Fifteen years of experience. Zero visibility outside his company. Nine months to find his next job.

"I had monitoring for services that didn't matter and zero observability into my own career. That's insane when I say it out loud."

It is insane. It's also normal.

What changes when you apply systems thinking to yourself:

You build monitoring. Quarterly check: Am I learning? Am I visible? Am I building relationships outside these walls?

You create redundancy. Network beyond your company. Skills beyond your current role. If this job disappears tomorrow, what catches you?

You define SLOs. Not "grow more." Specific: three external conversations monthly, one public post weekly, one new domain quarterly.

Takes an hour every three months.

You build systems because drift is the default.

The question isn't whether you're technical enough.

It's why your career is the one system you forgot to build.

♻️ Repost and comment if you've been running on vibes

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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.

A Staff Engineer I know spent four years at a company trying to break into leadership. Delivered everything asked of her. Mentored half the team. Proposed architectural improvements that would have saved months of pain.

Nothing moved.

Her skip-level kept saying "soon." Her ideas kept dying in committee. Her manager kept pulling her back into code because "we need your hands on this."

She thought she wasn't ready.

Then she changed companies.

Within eight months: promoted. Leading a platform team. Architecting systems instead of just building them. Her ideas now shaped the roadmap instead of disappearing into Slack threads.

Same talent. Different soil.

Here's what I've learned watching technical leaders for twenty years:

Some environments starve you. Politics beats impact. One failed experiment ends your credibility. "Hands-on" becomes a cage instead of a strength. Your growth plan is "figure it out."

Some environments feed you. Decisions stick. Failure is data. Leading means strategy, not just execution. Someone actually invests in your development.

The brutal part: it's hard to tell the difference when you're inside it.

You assume the problem is you. That if you just shipped more, worked harder, got better at "playing the game," things would change.

Sometimes they would.

Often they won't.

The company isn't broken. It's just not built for what you need. And no amount of effort changes soil composition.

The engineer I mentioned? She told me later: "I wasted three years thinking I wasn't good enough. I was just planted in the wrong ground."

Your talent stays constant.

Your environment is a choice.

If you've been grinding without growing, ask yourself:

Is it you?

Or is it your soil?

Sometimes the bravest move isn't working harder.

It's walking toward better ground.

♻️ Repost and comment if you've made this move

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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.

I spent years thinking dedication to the job was leadership. First one to respond. Last one to log off. Phone on the nightstand because production might sneeze at 3 AM.

Slack before coffee. Email during dinner. Weekend? That's just Monday cosplaying as free time.

I was performing dedication for an audience that wasn't watching.

Here's how it happens:

First it's "just during launches." Then "just for critical systems." Then somehow everything becomes critical. Your kid's soccer game is critical. Your lunch is critical. Your shower is apparently critical because you brought your phone in there "just in case."

Just in case of what? An emergency that only you can solve while shampooing?

We've built elaborate monitoring systems for services nobody uses. We get paged if a database hiccups.

Meanwhile: one hundred and twenty-six Slack checks before noon. Not a single one necessary.

Your phone addiction doesn't have an SLO. Maybe it should.

A Director I know finally checked his screen time. Seven hours and twelve minutes. Daily. On his phone alone.

"That can't be right," he said. "I'm busy. I don't have time to be on my phone that much."

The phone disagreed.

Availability isn't leadership. It's a coping mechanism wearing a tie.

You're not responding fast because your team needs you. You're responding fast because the dopamine hit of "being needed" is easier than sitting with whatever you're avoiding.

Boredom. Uncertainty. The quiet voice asking if you're actually making a difference or just making yourself feel busy.

Your phone is a pacifier. And we're all walking around pretending it's a productivity tool.

I'm not here to lecture you about touching grass. I still check my phone too much. We all do.

But I've started asking a different question:

Am I reaching for this because something needs my attention? Or because I can't handle five seconds of silence?

The answer is uncomfortable about 80% of the time.

Your team doesn't need you available 24/7. They need you present when you're actually there.

Big difference.

Start here: Check your screen time. Just look at the number. Don't judge it. Just see it.

Then ask yourself if that's who you want to be.

Because you've built systems to monitor everything except this.

Maybe it's time.

♻️ Repost and comment if you've checked Slack more than you've checked on yourself this week

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Most tech leaders will finish this year where they started.

Same title. Same scope. Same invisibility.

Not for lack of talent. For lack of intention.

They focus on the work and assume the work speaks for itself.

It doesn't.

But this is good news. The gap between stuck and sought-after isn't ability. It's habit.

Six months of practice. Five changes. A career unrecognizable from today.


1. One conversation a week with someone outside your company.

Not networking. Conversation.

The CTO navigating what you'll face next year. The VP who built what you're attempting. The founder hiring for a role you'd decline but could learn from.

Twenty-six conversations. Your perspective shifts. Your network expands. Opportunity finds you instead of the reverse.

Most leaders are too busy. That's why most leaders are invisible.


2. One piece of writing each week about how you think.

Not polished. Not strategic. Just captured.

The tradeoff you debated Tuesday. The mistake you made in March. The framework behind your last three decisions.

Twenty-six artifacts. A trail of clear thinking that follows you everywhere.

Six months ago, Google didn't know you. Now it does.


3. One "I don't know" spoken aloud each day.

Technical leaders rise on expertise. Then they reach roles where expertise isn't enough.

The practice: catch yourself about to bluff. Stop. Say it.

Feels like weakness at first. Becomes a superpower by month three.

Your team trusts you more because you stopped pretending.


4. One question asked monthly: "What should I stop doing?"

Your calendar is archaeology. Layers of decisions made once, never revisited. Meetings that outlived their purpose. Work you do because you always have.

Ask your team. The first month, silence. By month three, honesty. By month six, hours reclaimed.

Those hours become strategy. The thinking you never have time for.


5. One protected hour weekly for work only you can do.

The roadmap that never gets written. The business case that would unlock funding. The relationship with your CEO that would change everything.

Block it. Protect it like uptime.

Twenty-six hours of strategic work you wouldn't have done otherwise.

Small numbers. Massive compound effect.

Six months is long enough for change. Short enough for focus.

Most people will read this, nod, and stay busy.

The ones who act will wonder why they waited.

Start this week.

♻️ Repost and comment if you're starting today 

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undefined undefined

Founder

Vice President of Information & Technology

Pandora Jewelry

Co-Founder / Chief Technologist

Systems Consultant

You have 30 seconds. Name your top three accomplishments from last year.

Specific deliverables. Measurable impact. No "supported the team" or "contributed to projects."

If you struggled, so will your team.

Amazon just formalized what's coming everywhere: your value is no longer what you're capable of. It's what you can prove you delivered.

Used to be: "When you're at your best, how do you contribute?"

Now it's: "List 3-5 specific accomplishments. What did you deliver?"

One question is about potential. The other is about evidence.

That shift should concern every technical leader.

Here's why:

Your best engineers are often your quietest. They prevent outages, not just fix them. They improve systems gradually, not dramatically. They make everyone around them more productive in ways that don't fit neatly into a bullet point.

Now they're being asked to list accomplishments. And "nothing broke because of me" doesn't fit the template.

This isn't just Amazon.

Musk started demanding weekly accomplishment reports at Twitter in 2022. Zuckerberg declared a "year of intensity" at Meta. Google has toughened reviews. The entire industry is shifting from "what are your strengths?" to "what did you ship?"

The era of being valued for potential is ending.

Now you're valued for evidence.

This creates a problem: the system is about to reward self-promotion and punish quiet excellence. The engineer who documents every win will outperform the one who just wins.

Unless their leader helps them.

Here's what this means for you:

Start documenting your team's impact now. Not at review time. Continuously.

When someone prevents an outage, write it down. When a refactor saves hours of future work, quantify it. When someone mentors a junior engineer who then ships something great, capture it.

Your team won't do this for themselves. The engineers who most need to document impact are usually the ones least comfortable doing it.

That's your job. Not to game the system. To translate invisible work into visible evidence before the system punishes people for being humble.

The Amazon article quotes their new guideline:

"Consider situations where you took risks or innovated, even if it didn't lead to the results you hoped for."

Even they know accomplishments aren't just successes. They're attempts. Experiments. Calculated risks that didn't pan out.

Help your team see that. Help them articulate not just what shipped, but what they learned from what didn't.

The question "what did you get done?" is coming to every company.

Make sure your team has a good answer.

Not because the game changed.

Because you taught them how to play it.

♻️ Repost and comment if your team needs to hear this

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"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?"

A VP of Engineering I know spent six months writing engineering principles. Posted them on Confluence. Shared them in all-hands. Had a designer make posters.

Blameless culture. Growth mindset. Learning from failure.

Beautiful words. Framed and mounted.

Then someone missed a sprint commitment. Then technical debt broke something customer-facing. Then a senior engineer pushed back on an impossible deadline.

That's when the real culture showed up.

Not the documented one. The actual one.

The one that asks "who" before "what." The one where blameless post-mortems somehow always end with action items for the engineer who deployed. Never for the PM who changed requirements mid-sprint. Never for the executive who demanded the shortcuts.

Your engineering culture doesn't live in your handbook.

It lives in seven moments:

When an engineer raises technical debt. Do they get investment or "we'll revisit next quarter"?

When a post-mortem happens. Are you hunting for the person who failed or the system that allowed it?

When someone questions an estimate. Is that insubordination or the healthy pushback you claim to want?

When your best engineer complains. Are they "difficult" or worth listening to?

When someone asks for refactoring time. Is it waste or maintenance?

When production breaks. Is someone getting blamed or everyone getting smarter?


A CTO told me his culture was "strong" because they had detailed engineering values. I asked what happened last time a deadline was missed.

Long pause.

"We had a tough conversation with the team about accountability."

"What about the sales VP who promised the customer a date without asking engineering?"

Longer pause.

Culture isn't what you document. It's what you enforce when enforcing it costs something.

When protecting an engineer means challenging an executive. When admitting system failure means your process looks bad. When addressing behavior means losing someone who ships fast.

That's when values become real or become decoration.

Your team already knows which one yours are.

They're not reading your Confluence pages.

They're watching what happens after things break.

And they're taking notes.

♻️ Repost and comment if you've seen the gap between culture decks and culture reality

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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?"

A Director of Engineering told me this last month. He'd built his entire career on being the smartest person in the room. That's how he got promoted. That's how he measured worth.

Now he was sitting across from someone who made him feel like a junior engineer.

I asked what he did next.

Long pause. Then a slight grin.

"I hired her before she could finish interviewing anywhere else."

Six months later: his platform handles 10x the load. Incidents dropped by half. Architecture decisions that used to take weeks now take days.

His VP just asked him to take on two more teams.

None of that happens if his ego runs the interview.

Here's what I've learned watching technical leaders for twenty years:

The ones who stall are the ones who need to be the smartest person in the room. Every hire feels like a threat. Every expert on their team feels like competition. They build teams that make them feel secure instead of teams that make them successful.

The ones who scale have killed that instinct.

They know the job changed. The skills that got them promoted aren't the skills that build something bigger. At some point, being the smartest person becomes the bottleneck.

Your company needs capabilities you don't have. Your team needs expertise you can't provide. Your next phase requires hiring someone who makes you uncomfortable.

That discomfort isn't a warning. It's a signal.

When a candidate makes you nervous, that's not a threat to your value.

That's growth trying to happen.

The Director told me later: "I used to hire people I could teach. Now I hire people who teach me. The results aren't even close."

Your technical skills got you promoted.

Your willingness to hire past them determines what you actually build.

The next time someone makes you feel like the dumbest person in the interview, don't panic.

Hire them before someone else does.

♻️ Repost and comment if you've hired someone better than you 

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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."

I've been in this room at three different companies. Same silence every time.

Everyone sees it. Nobody wants to be the one who says stop.

So I stopped trying to say stop.

Instead, I started having smaller conversations. Finance was already frustrated about the budget creep, so I helped them put real numbers on it: $240K spent to solve a problem that generated $30K in complaints the previous year. They didn't need convincing. They needed ammunition.

Sales was losing deals during the transition chaos. I asked what they'd do with the two engineers currently stuck on integrations. Turns out they had a punch list of quick wins collecting dust.

The VP who sponsored the project? I never asked him to admit it was failing. I just walked him through what "pivoting to a phased approach" could look like. Same outcome. His reputation intact.

Three weeks later, he presented the "strategic pivot" to leadership. Got praised for decisive resource allocation.

I sat in the back of that meeting and said nothing.

The project was done. The politics were handled. And $180K got redirected to three smaller bets that actually shipped.

You don't need authority to change direction. You need to make the new direction easier than the old one.

Most of that work happens in hallways, not conference rooms.

♻️ Repost and comment if you've ever sat in that room where everyone knew but nobody spoke

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You're excellent at saving failing projects.

That's exactly why nobody trusts you to build something new.

A Director I know spent seven years being the person they called when things went sideways.

Backend rewrite stalled? Call him.

Migration falling apart? Call him.

He fixed every single one. Got thanked in all-hands. Built a reputation as the guy who delivers when it matters.

Then a VP role opened. Greenfield AI platform. Strategic. Exactly what he'd been working toward.

They gave it to someone with half his experience. Someone who'd never rescued a single failing project.

"We need you where you are," they told him. "You're too valuable in crisis mode."

Translation: We've trained you to be our firefighter. We're not promoting firefighters to city planning.

When you're the fixer, strategy conversations happen without you. Because strategy people build things. You rescue things.

Your team stops wrestling with hard problems because why struggle for three days when you'll solve it in three hours? And the organization's incentive becomes keeping you exactly where you are.

And he admitted he let them.

He wasn't staying because they needed him. He was staying because being needed felt like being valuable.

The rush of solving what nobody else could. The gratitude. The reputation. It was easier than the uncertainty of building something that might not work.

He eventually left. Joined a startup as VP of Engineering. Built a platform from scratch. Hired his own team. Shaped product strategy from day one.

Same person. Different expectations.

If you're the one everyone calls when things break, ask yourself: when's the last time someone asked you to build something that doesn't exist yet?

Your ceiling isn't your skill. It's what you're known for.

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"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.

Five strategic initiatives that year. AI integration. Platform modernization. Data warehouse. Customer portal. Mobile redesign.

Five kickoff meetings. Five vision docs. Five "this changes everything" presentations.

Six months later: five projects at 70%. Zero in production.

Every time something hit the messy middle, he'd already spotted the next shiny thing.

"We should really be thinking about..."

"Have you seen what the competitor launched?"

His team learned to treat his enthusiasm like weather. Intense when it arrives. Gone by Thursday.

Starting is easy because starting is fantasy. You imagine perfect outcomes. Sell the vision. Feel like a strategist. The kickoff high is real.

Then reality arrives. Edge cases. Integrations that don't work. Your beautiful architecture meeting ugly constraints.

Finishing means watching your perfect idea become imperfect. Every compromise chips away at the vision. Every bug reveals something you missed.

So you escape. That refactor can wait. This new AI thing is more urgent. The old project isn't abandoned. Just... reprioritized.

You call it strategic. Your team calls it what it is.

The engineer's question broke something open.

That VP went home and sat with it. Why did finishing feel so hard?

He'd been chasing the dopamine of beginnings because completed work scared him. Finished means judged. Finished means finding out if your idea actually works.

Next week, he stopped three initiatives. Put everyone on two.

One shipped in six weeks. Messy. Customers used it anyway. The other shipped in ten. Also imperfect. Also valuable.

First time in two years his team could say "we built that." Not "we're building." Built.

How many initiatives on your roadmap will actually ship this year?

If you love kickoffs but skip standups. Write vision docs but avoid release planning. Seven priorities, no shipping rhythm.

You're not strategic. You're scared of finishing.

Your team already knows.

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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.

Too academic. Might not be practical. Probably wants more money than we budgeted. Could be difficult to manage.

I spent twenty minutes inventing problems that didn't exist.

Then I caught myself.

I wasn't protecting the team. I was protecting my ego from a guy who'd make my technical opinions look like napkin sketches.

Hired him anyway. Hardest offer letter I ever sent.

Within a month, he'd casually dismantled two architectural decisions I'd been defending for years. Didn't even realize he was doing it. Just mentioned better approaches like he was commenting on the weather.

My face went hot in that meeting. Old instincts screaming. Defend yourself. Poke holes. Find the flaw.

I shut up instead.

He was right. I'd been wrong for two years. The team knew it. I knew it. The only thing left was whether I'd make it weird.

I didn't. Bought him coffee. Asked him to explain the better approach. Watched three engineers' respect for me go up, not down.

Weird how that works.

The leaders who feel threatened by brilliance hire people they can correct. Safe hires. Controllable hires. People who make them feel smart in meetings.

Then they wonder why their teams plateau.

My job isn't writing code anymore. It's finding people who write it better than I ever did and convincing them to stick around.

That PhD? He rebuilt our entire data pipeline.

He doesn't need me to review his architectures. He needs me to block reorgs, fight for headcount, and keep executives from "just checking in" on his projects.

Different job. Both necessary.

Your technical expertise has an expiration date.

Your ability to spot those people and get out of their way?

That compounds forever.

♻️ Repost if you've hired someone who made you better by making you nervous 

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