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

“They’re not listening…I just don’t get it!”

Me: "It’s not them, it’s you." 🤯

Most leaders just tell.

They tell people what to do.
They tell people what happened.
They tell people what’s next.

But telling doesn’t inspire.
It informs.

And then, “People just don’t listen…”

The Ops Leader was initially shocked when I gave him that tough feedback.

He’s black and white, efficiency-driven. Great at  the “what.” Enneagram 1.

But he sucks at telling stories.

You see, the real magic is in storytelling. 

It’s where you connect to emotion and move people to action.

A great story turns a plan into a mission.
It turns compliance into commitment.
It makes people feel the “why,” not just memorize the “what.”

Here’s what I’ve seen: 
Great leaders are storytellers.
Build belief before they demand behavior.
Use story as a bridge between logic and emotion. Connect data and drive.

So if you want to lead better…
Stop just telling. Logic justifies.
Start storying. Emotion drives action.

Because people don’t follow instructions.
They follow inspiration.

I was on a call with a CEO who had reached her limit.

↳The team was grumbling. 
↳She was micromanaging. 
↳She was unclear.

She’d reshuffled the team, clarified the strategy, aligned priorities, and poured fuel into execution.

And still, deadlines were missed, the content didn’t land, and the team kept talking about ideas while results quietly evaporated.

She said something I won’t forget:

💡 “At some point, I have to stop asking what’s wrong with the plan... and start asking what’s wrong with the people.”

She's right. That’s the trap.

🙏 👉 You hope good people will eventually "get it."

Even when the data says otherwise...

When clarity is present and execution still falters, it’s not a strategy issue.
It’s a standards issue.

Time to make a change. 🚀

You can’t build a great company on hope and hesitation.

Quit accepting mediocrity.

Kennēsys

• Fractional CIO/Technology Consulting
	• Strategic Planning
	• Technology Roadmaps
	• Systems Sourcing
	• AI / BI / ML practical applications
	
Recent projects:

	• Helped wholesale distributor add 2 points of margin through strategic vendor analysis 
	• Rightsized 2 year long failed CRM project through strategic roadmap creation
	• Accelerated development team formation and delivery for SaaS system provider
	• CIO and strategic advisory services for startups and decades old family businesses

Founder

Classic Brands, LLC

Classic Brands is a designer, manufacturer, and wholesale distributor of mattresses, bedding accessories, and furniture.  Headquartered in Columbia, Maryland.

Member of the Executive Leadership Team, reporting to the CEO

• First internal IT employee recruited by the CEO to transform aging internal systems and setup organization for growth.
• Successfully managed a ransomware incident within the first 2 months in the role.
• Learned the business, existing systems, developed an IT strategy, roadmap, and plan for execution within the first 60 days.
• Led the evaluation, selection, and implementation of the following systems:
     - Supply Chain planning solution – Adexa S&OP and S&OE
     - Transportation management solution - Minisoft with planned transition to Blue Yonder
     - EDI solution. Including migrating existing trading partners along with adding 12 new partners during migration process – True Commerce
     - ERP solution. AP, AR, accounting, supply chain, order processing, procurement, manufacturing – Microsoft D365 F&O
     - Treasury management solution to aid in AP/AR processing, bank reconciliation, and collections – SK Global Software
• Led the tech and security areas for a new 425k sq/ft warehouse including Wifi design, security, building access, AV and conferencing setups.
• Led project to implement Azure technologies and integrate with existing AWS environment. Completed full migration to Azure.
• Led advanced analytics, BI project utilizing Azure Advanced Analytics, Databricks, and PowerBI
• Built internal IT team to focus on plan/build/run setup. Implemented iterative, DevOps way of working to perform multiple production releases to all systems weekly when needed.
• Managed the custom development of a warehouse management system with real time integration into Microsoft D365 Finance and Operations ERP system utilizing AWS and Azure technologies including Service Bus and D365 Business Events.  WMS technology sold to National 3PL organization.

Vice President of Information & Technology

Pandora Jewelry

Global Head of Application Development, member of Enterprise Architecture board, and Global IT Management Team. 

Tasked with leading PANDORA's global transition to an Agile organization.

Responsible for all B2B and B2C application development and delivery. 

Led key initiative establishing PANDORA Agile, iterative way of working for all internal and external development teams.  Managed a global team of 16 internal resources with 40-60 contractors.

Head of Agile Development, Global IT

Capabilities lead for all IT application workstreams.  Managed a global team of 45 with 9 direct reports.

Work pillars included applications development, supply chain, master data management, integrations, and enterprise architecture.

Director, Information Technology, Global IT

Recruited by the CEO as the first internal IT employee in the Americas to establish a high-performing technical organization capable of managing hyper-scaled growth.

Responsible for all aspects of IT in the Americas. Led all technical initiatives to support the growth from $80MM to $1B while keeping IT spending under 0.4% of regional revenue with a 98+ internal satisfaction rating.

Built an internal team of 26 with another 20-40 contractors.

Key projects included:
	• ERP migration
	• Custom built cloud-based B2B retailer portal
	• B2B CRM/xRM sourcing, implementation, and custom development
	• B2C single consumer view solution
	• Sell-through data collection, and analytics program 
	• Co-op advertising processing solution
	• BI analytics and data warehousing
	• Cyber security management and incident recovery
	• Warehouse management- WMS system sourcing and implementation
	• POS sourcing and implementation
	• Agile iterative way of working

Head of Information Technology, Americas

HubKey, LLC

Co-Founded HubKey, LLC in 2006 with a software development team. HubKey is a provider of outsourced Business to Business e-commerce solutions. Primarily focused on outsourced EDI document translation and ERP system integrations.

Chief Technologist & Co-Founder | 2007 – 2010
• Developed and wrote the five-year business plan
• Successfully located and acquired investors needed to initially fund the company
• Setup internal processes and equipment, including all accounting systems, expense tracking, servers, and software
• Responsible for the primary technology direction of the company and managing product development
• Responsible for securing clients and managing sales and marketing activities

Co-Founder / Chief Technologist

Gross, Mendelsohn & Associates, P.A.

GMA is a full-service CPA and consulting firm founded in Baltimore in 1960. Named one of the top 200 CPA firms in the US for the past seven years. Technology consulting practice is led by CPAs and focused on business and software systems, along with networking solutions and infrastructure.

Systems Consultant | 2008 – 2009
Major Responsibilities and Contributions:
• Led CRM practice, including internal implementation of the Dynamics CRM solution at GMA
• Responsible for application development, database development, and business systems consulting for regional client base
• Responsible for infrastructure, unified communication, and network consulting

Systems Consultant

GrandNetworks, LLC

Founded GrandNetworks, LLC in 2003 with two business partners, to provide experienced technology direction and support to businesses in and around Jackson Hole. Handled all the technology needs for 12 business clients in the area. responsible for all day to day duties
including procuring clients. Performed all accounting duties. Managed phone support and resource scheduling.

Chief Technologist & Co-Founder | 2003 – 2007
• Researched, recommended, and implemented paperless medical practice office utilizing tablet pc, electronic medical records, and voice recognition software
• Performed client/server migration to HIPAA-compliant software package for 20- node office
• Completed multiple Microsoft Small Business Server setups
• Developed contact management system for hedge fund company utilizing Microsoft technologies
• Developed expense tracking software application for Pocket PC using Visual Studio.Net
• Researched and planned development of an e-commerce software application to integrate with most major small- to medium- sized business management software packages utilizing XML, InfoPath forms, BizTalk Server and AJAX

Prestige Brands, Inc.

Prestige Brands, Inc. is a 350M+ public company with operations based in Jackson, Wyoming, and sales and marketing offices in Irvington, New York. Prestige is a marketer and distributor of over-the-counter drugs, household cleaning supplies, and health and beauty aids. Responsible for developing, communicating, and executing the corporate technology strategy. Primary focus is to keep costs and operation staff to a minimum through strategic application of technology, while designing, developing, and maintaining nimble systems capable of easily integrating with brand or company acquisitions.

Information Technology Manager | 1999 – 2006
• Guided the technology direction to compensate for exponential growth from a $60M company to $350M in 6 years, while adding only 4 additional operations staff
• Develop and manage IT budget
• Successfully headed numerous company acquisitions, including one that more than doubled total revenue
• Successfully headed multiple 3rd party warehouse conversions
• Handled internal corporate restructuring projects
• Implemented automated order and invoice processing system
• Automated day end and month end closing processes
• Planned and executed ERP software migration from DOS to Windows-based system
• Headed technology team to secure Sarbanes-Oxley compliance
• Headed team to develop and implement custom marketing and sales forecasting application
• Developed contract management tracking solution
• Developed custom advertising planning and tracking solution
• Developed sales and distribution reporting solution
• Responsible for incorporating all data history from each acquisition
• Implemented service management and support desk solution and processes
• Planned and executed software migration from Pervasive to MS SQL server along with ERP upgrade

IT Manager

Life-Link International

EDI Manager / Systems Administrator

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

A consultant pitched us a $1.2M "digital transformation."

Beautiful deck. Bold promises. Timeline: 18 months.

My newest engineer, three months on the job, raised his hand in the pitch meeting.

"Why are we rebuilding the entire platform when 80% of our problems are in two legacy workflows?"

The room went silent.

The consultant started explaining why comprehensive transformation is necessary. Why you can't just fix pieces. Why thinking small keeps you stuck.

My engineer pulled up our support tickets on his laptop.

"These two workflows account for 87% of customer complaints and 60% of our support costs. If we fix these, what's left that actually needs transforming?"

He was right.

We didn't hire the consultant.

Instead, we spent six weeks rewriting those two workflows. Cost: $120K.

Customer complaints dropped 71%. Support costs down 58%.

Same impact the consultant promised. 90% cheaper. 8x faster.

Here's what saved us $1M:

A three-month employee who wasn't afraid to challenge a seven-figure pitch.

Most leaders build teams that agree with them.

They mistake nodding for alignment. Silence for success. Consensus for correctness.

Then wonder why their projects fail, innovation stalls, and the obvious solution was sitting in someone's head the whole time.

The best solutions come from the person brave enough to say:

"What if we're overcomplicating this?"

But only if you've built an environment where they're not afraid to say it.

What idea did someone on your team challenge that you're grateful they did?

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

I thought my architect was lazy.

Three months. Every project. Same pattern: Brilliant ideas in planning. Mediocre execution. Deadlines missed.

"Just not driven enough," I thought to myself.

Then I overheard him talking to another engineer.

"I don't know why they keep giving me these projects. I always mess them up. I'm probably getting fired soon."

Wait. What?

This guy had shipped our entire authentication system. Built the API that powered 60% of our revenue. Mentored four engineers who now led their own teams.

And he genuinely believed he was failing.

I pulled him into a room:

"You think you're getting fired?"

Long pause. "I mean... I miss deadlines. My code always needs fixes. Everyone else seems better at this."

"You shipped our authentication system in six weeks. That was supposed to take four months. You didn't miss a deadline, you crushed an impossible one."

"Yeah, but it had bugs."

"Every system has bugs. You fixed them in production without a single customer noticing. That's mastery, not failure."

I watched his face. He'd been carrying this story for months. Maybe years.

Here's what I realized:

He wasn't lazy. He was terrified.

Every project felt like proof he was about to be exposed as a fraud. So he'd hesitate. Second-guess. Rewrite code that was already good.

Not because the code was bad. Because he couldn't see that it was good.

The shift took six weeks.

Not because I gave him a pep talk. Because I started pointing out what he couldn't see.

"That database optimization you just did? That's senior architect-level thinking."

"The way you explained that technical decision to the CEO? I couldn't have done it better."

"Three engineers just asked for your code review specifically. They trust your judgment."

Small observations. Specific evidence. Things that were true but invisible to him.

Three months later:

He proposed redesigning our entire data pipeline. Something he would've never touched before because "someone better should handle it."

His proposal was brilliant. We built it. It's still running today.

Here's what nobody tells you about leadership:

Your team's performance ceiling isn't set by their skills.

It's set by the story they're telling themselves about their skills.

My architect was world-class. But his internal narrative said he was barely competent.

So he performed at barely competent, despite having world-class capability.

Your job isn't just managing work. It's revealing the gap between who they are and who they think they are.

Because that gap is where potential goes to die.

Who on your team is operating below their capability because they can't see what you see?

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I got invited to speak at a major tech conference.

My first thought? "They definitely meant to email someone else."

For 6 weeks, I was convinced the conference organizers had made a mistake.

Maybe they confused me with another Phillip. Maybe someone dropped out and I was the backup plan. Maybe they just needed to fill a slot and picked a random LinkedIn profile.

I'd built platforms handling millions of users. Led teams through impossible migrations. Solved problems that kept other CTOs up at night.

But speaking in front of 500 people about technology leadership?

"What if they realize I'm not actually an expert? What if someone asks a question I can't answer? What if I'm exposed as someone who just Googles solutions like everyone else?"

Then 3 days before the conference, my CTO friend said something that broke me:

"Phillip, they invited you because you've actually done the work. Most speakers are consultants who've never shipped production code. You've got the scars. That's what people want to hear."

The talk went fine. Better than fine.

Afterwards, a VP of Engineering pulled me aside: "That story about your failed cloud migration? That's exactly what we're going through right now. Nobody talks about the real mess. Thank you."

Here's what hit me:

My imposter syndrome wasn't telling me I wasn't qualified. It was telling me I cared about getting it right.

The leaders who feel like frauds are the ones constantly pushing beyond their comfort zone.

Real imposters don't worry about being imposters. They don't stay up rewriting presentations 12 times. They don't obsess over whether their advice will actually help people.

Your self-doubt isn't evidence you don't belong. It's evidence you give a damn.

The moment you stop questioning yourself? That's when you should start worrying.

What moment made you realize your imposter syndrome was actually trying to keep you sharp, not hold you back?

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I watched a VP of Engineering clean out his office last month.

Twenty-three years. Three platform migrations. Built a 40-person team from nothing.

Gone in a "restructuring."

Packing up awards and family photos, he kept saying: "I don't know who I am without this place."

Here's what hit me.

Nobody took his knowledge.
Nobody erased his network.
Nobody deleted the systems he built that still run today.

But he couldn't see any of that. Because his identity was the badge. The title. The corner office.

This is the trap.

We introduce ourselves by where we work, not what we've learned.

"I'm the CTO at..." instead of "I solve scaling problems."
"I run engineering for..." instead of "I build teams that ship."

Your job is temporary. Your growth isn't.

Three weeks later, I got a text from him.

"Just closed a consulting deal. $45K for three months. They found me because someone I mentored five years ago recommended me."

Not because of his title. Because of the problems he'd solved and the people he'd helped.

That's the shift:

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.

2) Build relationships outside your walls - The best opportunities come from people who've seen you in action, not algorithms matching keywords.

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.

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.

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."

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?

What skills have you developed that would make you valuable at any company?

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I've disagreed with my boss 47 times in three years.

Never once got fired. Usually got my way.

Here's how:

My CEO wanted to build a custom CRM instead of buying Salesforce. "We'll own the IP. Control our destiny."

This would burn 18 months and $2M we didn't have. But "that's stupid" wasn't going to work.

Instead: "Love owning our tech. Let's map out the development timeline against our Series B runway. Want to make sure we have capital to scale once it's built."

Three days later: "Been thinking. Maybe we start with Salesforce and build custom later when we have more resources."

The formula for winning arguments you can't afford to lose:

- Wrap your objection in their goal.

"We can't hit that timeline" loses.
"Let's protect the client relationship by under-promising and over-delivering" wins.

- Bring numbers, not feelings.

"This seems aggressive" dies.
"Last two launches we committed to aggressive timelines, we missed by 40% and lost credibility with the team" sticks.

- Make it collaboration, not confrontation.

"That won't work" = resistance.
"Here are two ways to get what you want without the downside" = partnership.

- Time it like your career depends on it.

Not in leadership meetings. Not when they're pitching investors. Not over Slack.

Private. Face-to-face. When they have mental space.

I trashed three promotable ideas by raising them at the worst possible moments.

The truth:

Your boss isn't trying to make bad decisions. They're solving problems you can't see from your seat.

Frame your disagreement as protecting their priorities. You stop being the obstacle and become their risk manager.

How many times have you been right but still lost the argument?

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Sarah told me she wasn't qualified to lead our platform rebuild.

I looked at her resume. Five years. Dozens of shipped features. Solved problems that made senior engineers quit.

"You're joking, right?"

"I'm serious. I'm not ready for a senior architect role."

Here's the thing: Sarah had imposter syndrome so bad she couldn't see what everyone else saw.

So, I made a bet that would either look genius or get me fired.

"I'm not asking if you're ready. I'm betting our most critical project on you. Because you are."

Week three, she's in my office:

"What if I make the wrong call and it costs us?"

"Then we'll fix it, together. But I've watched you work for two years. You see things others miss. That's not luck. That's skill."

Two months in:

She caught a scaling flaw in our design. Would've crashed under production load.

The flaw I missed. The senior engineers missed. Everyone missed.

Her "inexperience"? Actually, fresh eyes without bad assumptions.

Six months later:

Flawless launch. Board presentation. Three companies trying to poach her.

She stayed. Not for the money. Because someone believed in her before she believed in herself.

And here's what nobody tells you about leadership:

Training doesn't build confidence. Belief does.

Most leaders do it backwards: "Prove yourself, then I'll promote you."

But that's not how humans work.
People don't rise to meet expectations. They rise to meet belief.

The difference?

Expectations say: "Show me you can do this."
Belief says: "I already know you can. Here's your shot."

One makes people play it safe. The other makes them capable of things they didn't know they had in them.

Sarah runs the entire engineering org now. Still doubts herself sometimes.

But now she's got a track record of being right in spite of her doubts.

That started with one conversation: "You're ready. And here's specifically why I think so."

Not vague encouragement. Specific belief based on what I'd actually seen her do.

That's the move.

Who on your team needs to hear "you're ready" this week?

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All hands meeting. CEO mid-presentation. Forty slides deep.

"Our customer retention is at 94%."

From the back of the room, barely audible: "Actually... it's 83%."

Everyone turned. It was Matthew. Three weeks into their internship.

You could hear the room stop breathing.

The CEO paused. Looked at him. "Show me."

He pulled up his laptop. Walked through the data. They'd been using last quarter's numbers.

CEO said five words that changed everything:

"You're right. Thank you, Matthew."

Then to the room: "This is exactly what we need more of."

Matthew's now a full-time analyst.

Not because he was the smartest person in the room.

Because he had the guts to be honest when it mattered.

Here's what that moment taught me:

Skills get you hired. Courage keeps you valuable.

Your team already knows what's broken. They may just be afraid to say it out loud.

Build a culture where the intern can correct the CEO. That's how you stay competitive.

What's the bravest thing someone on your team has done recently?

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The most successful tech leaders I know can't code worth a damn.

I'm serious.

- They get comfortable being wrong.

My architect wanted to re-architect our platform. I knew enough to be dangerous. Not enough to be right.

Instead of nodding along, I said: "Explain this like I'm presenting it to the board tomorrow."

Third diagram in, I saw it. Her design assumed we'd replace our legacy billing system. We wouldn't. Couldn't.

That admission saved 3 months and $200K.

- They slow down when everyone else speeds up.

Three years ago, my team wanted to rebuild our embarrassing legacy code.

Everything in me screamed: "Fix it. Now."

Instead, I made them wait 6 months. Interview customers. Shadow support. Map every workflow.

The "broken" code was handling edge cases nobody remembered. Accounting had built processes around its quirks.

We fixed workflows. Left code alone. Revenue jumped.

Sometimes the best technical decision is no technical decision.

- They lead with uncertainty.

My biggest disaster? Playing genius founder with all the answers.

Partner API integration. I'd done these before. "Two weeks, max," I told the team.

Eight weeks later, still debugging. Their docs were fiction. Their errors were lies. Their support didn't understand their own system.

Cost: $150K and a delayed launch.

Now I start decisions with: "Here's what I think. Here's what worries me. Here's what I need."

Project failure rate dropped.

- Your job isn't having the best technical ideas.

It's creating conditions where the best ideas surface, and hidden problems can't hide.

What did admitting you were wrong teach you?

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I quit because of a Tuesday morning meeting.

Not the job. The manager.

Here's what happened:

Our product launch failed. Crashed fifteen minutes after going live. 50,000 users hit an error page. Support tickets flooding in.

My team worked 72 hours straight to fix it. We got it back up. Identified the root cause. Built safeguards so it couldn't happen again.

Tuesday morning, leadership meeting. My manager presenting.

"We experienced a significant technical failure due to inadequate testing by the development team."

He didn't mention the impossible timeline he'd promised the board. Or the corners he told us to cut. Or the warnings we'd given him two weeks prior.

He threw us under the bus in front of the entire executive team.

I handed in my notice that afternoon.

Six months later, I joined a different company. Same role. Similar pressure.

We launched a major feature. Also crashed. Also chaos.

But my new CTO sent one message to the leadership team:

"We had a rough launch. My team is working on it. I take full responsibility for not building in enough buffer time. Updates to follow."

Then privately to us: "What do you need from me right now?"

Same crisis. Opposite leadership.

One manager used his team as a shield. The other used himself as one.

Here's what that taught me:

Your boss doesn't just manage your work. 
They manage your dignity.

Great leaders absorb pressure from above and radiate clarity below.
Toxic leaders do the reverse, absorb credit, radiate blame.

The difference shows up in three moments:

→ When things break: Do they ask "what happened?" or "whose fault?"
→ When leadership asks questions: Do they say "we" or "they"?
→ When success happens: Do they share the spotlight or stand in it?

I've worked with dozens of tech teams. The difference between thriving and surviving isn't the technology.

It's whether their leader protects them or uses them.

The team with the bad manager? Three people quit within six months.
The team with the good one? Same people, three years later, still shipping.

Your technical skills matter. But your boss determines whether you get to use them or burn out trying.

What's one thing a leader did (or didn't do) that made you want to stay or leave?

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Black Friday. API throwing 500 errors. Revenue dropping $8K per minute.

The CTO panicked.

Customer complaints flooding support. Board asking for updates every hour.

His response? Emergency all-hands. Finger pointing. "Who deployed last?"

I watched our best engineers shut down. Stopped sharing ideas. Started covering their tracks instead of fixing the problem.

That's when I learned the difference between tech bosses and tech leaders.

Tech bosses during a crisis:

• Demand explanations before solutions
• Turn post-mortems into blame sessions
• Escalate panic up the chain
• Measure who's working longest hours
• Create fear that kills creativity

Tech leaders during a crisis:

• Roll up sleeves and debug with the team
• Ask "What's the fastest path to resolution?"
• Shield engineers from executive pressure
• Focus on customer impact over politics
• Bring calm energy that enables thinking

What happened next changed everything.

Mark, one of our junior devs, had been silent the whole meeting. Finally spoke up: "What if this isn't our code?"

He was right. Third-party CDN issue. Fixed in twenty minutes once we stopped looking at our own code.

But here's what haunted me: He almost didn't share that insight.

Told me after: 'I figured if it was that obvious, someone smarter would've already seen it.'"

The blame-first approach had taught him to doubt himself. Made him afraid to suggest the "obvious" thing that senior people might have missed.

That junior dev saved us hours of debugging in the wrong direction. But only because he finally found the courage to speak.

The best technical leaders create the conditions where the right answer can come from anyone.

They don't just manage incidents. They build the trust that makes breakthrough thinking possible.

How do you make sure the quietest voice in the room gets heard during a crisis?

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I spent three weeks preparing a technical deep-dive for the board.

Seventy-three slides. Performance benchmarks. Architecture diagrams. ROI models.

Rehearsed it twelve times.

Got through slide four before the CEO stopped me.

"Phillip, I don't care about the tech stack. I care about our customers. Are they happy or not?"

I froze. I'd spent three weeks preparing for the wrong conversation.

Here's the scariest thing about tech leadership:

Your biggest failures won't come from bad code. They'll come from being brilliant at the wrong thing.

I see this all too often. Engineers who can debug distributed systems in their sleep but can't explain why it matters to the person signing the checks.

The skills that actually got me promoted had little to do with technology:

→ Learning to speak three languages fluently: Engineer. Executive. Customer.

Same problem. Different translations:

- To engineers: "Our API response time averages 2.3 seconds with p99 at 4.1 seconds"
- To executives: "Customers are abandoning carts because checkout feels broken"
- To customers: "We're making checkout faster so you spend less time waiting"

→ Building trust with finance people who think all engineers are expensive wizards

→ Making decisions with 60% of the information and being okay with it

→ Saying no to the CEO's pet project without getting fired

→ Leading through a massive platform failure without losing the team

Want to know what's truly frightening?

Most tech leaders spend more time optimizing their IDE than their communication skills.

Then wonder why they're stuck explaining technical debt to people who fell asleep at "microservices."

Your technical certifications expire. Frameworks change. Platforms evolve.

But the ability to translate technical complexity into clarity for non-technical humans will compound forever.

The CTOs and VPs I know didn't get there by being the best coders. They got there by being the best translators.

Your most important project isn't the platform migration.

It's becoming someone who can talk to all levels of the organization and make the tech problems simple enough that the right people can weigh in on the right decisions for the right reasons.

Because brilliant solutions die in translation every single day.

And the person who can explain "microservices" to your CFO in a way that makes them say "oh, now I get it"? That person is irreplaceable.

Happy Halloween. The real horror story is being technically right and professionally ignored. 🎃

What's one technical concept you learned to explain in plain English that changed how people saw you?

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I watched a senior architect panic when our CTO said "We're moving off React."

This guy had spent five years mastering React. Spoke at conferences about it. Built his entire reputation on it.

"My skills are obsolete now," he told me.

Here's what I told him:

"React isn't your skill. Problem-solving is your skill. React was just the tool."

Three months into the new stack, he was leading the migration. Not because he learned the framework fastest. Because he understood system design, team dynamics, and what actually mattered to the business.

That's technical capital.

Not the framework you know. The judgment you've built.

What compounds:

→ Making decisions with 60% of the information (frameworks change, ambiguity doesn't)
→ Translating "our database is slow" into "we're losing $40K monthly in abandoned carts"
→ Staying calm when production is on fire and everyone's looking at you
→ Knowing which problems to solve now vs which to defer
→ Leading teams through change without losing them

What expires:

- The specific syntax. 
- The hot framework. 
- The buzzword on your resume.

Here's the shift:

Junior engineers stress about learning the next framework.

Senior leaders invest in judgment that transcends the framework.

Your technical skills get you hired. Your technical judgment keeps you indispensable.

The React architect? Now mentoring teams on system thinking. The framework changed. His value didn't.

What's one technical judgment call you made that had nothing to do with code?

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Your $400K platform upgrade has been “85% complete” for nine months.

Everyone’s exhausted. The vendor’s confused. Your team stopped showing up to status meetings.

Sound familiar?

I’ve seen this 30+ times.

You don’t have a technology problem, you have an alignment problem.

Projects start strong, then lose direction because:

→ Business goals shifted, but requirements didn’t
→ Three departments have three definitions of “done”
→ Nobody remembers why this matters anymore

The fix isn’t pushing harder.

It’s pausing smarter.

Bring every stakeholder back and ask three questions:

1️⃣ What business outcome are we actually solving for?
2️⃣ What can we cut that doesn’t serve that outcome?
3️⃣ Who owns success when this ships?

I watched a client rescue an 18-month ERP disaster in 90 days, not by adding resources, but by removing everything that didn’t serve the core goal.

Your stalled project isn’t broken.
It’s just pointed in the wrong direction.

Run this 3-question audit before you spend another dollar.

The hardest part about realignment?

Getting stakeholders to admit the original goal has changed.

Once you name it, everything else gets easier.

What's been your biggest 'aha' moment when salvaging a stalled project?

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The 52-year-old architect saved our platform rebuild.

My leadership team wanted a "digital native." Someone who "gets modern tech."

I pushed back. Hard.

They thought I'd lost my mind.

First week, Janet spotted critical architectural gaps that would have derailed our timeline.

Twenty-five years building enterprise systems gives you that kind of foresight.

The objections were predictable:

"She's never worked with our stack."
"She's from the legacy world."
"Will she even fit with the team?"

Six months later:
→ Most stable deployment we've ever had
→ Three junior developers she mentored now lead their own teams
→ Her design prevented months of rework
→ Minimal production issues since go-live

Here's what surprised me:

I thought she'd need months to catch up on our tools.

She learned our entire stack in weeks. Not by memorizing docs, but because she understood system architecture at a level that made the tooling almost irrelevant.

That's when it hit me: We're hiring backwards.

We optimize for framework familiarity over problem-solving depth.

We mistake recent bootcamp graduation for engineering wisdom.

Experience isn't about knowing the latest tools. It's pattern recognition across decades of watching things break in production.

The 25-year-old can implement features faster.

The person with 25 years knows which features will collapse under real-world pressure.

Both matter. But only one prevents disasters you didn't know to plan for.

What did your most experienced hire teach your team that no training program ever could?

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Trust in technical leadership isn’t built on GitHub commits; it’s built on kept promises.

$40M cloud migration. Three months behind.
Standups turned into one-word answers. Side chats died when I walked by. Code reviews felt like negotiations.

Then I found the Slack channel.

↳ Private workspace. Six weeks of messages.
↳ My senior engineers were building a parallel solution, nights and weekends.
↳ Four months earlier they’d flagged scalability bottlenecks in my design.
↳ I waved them off: “We need speed, not perfection.”
↳ They tried again, with data and prototypes.
↳ I hid behind, “The business already committed.”

They stopped arguing and built what would actually work.

That was the bug: not in the code, in the promise layer, the gap between what I asked for (“speak up”) and what I rewarded (compliance).

What fixed it wasn’t a clever algorithm. It was three moves:

1. Admit I was wrong, in public.
2. Pivot to their architecture (six weeks of replan; avoided an 18-month failure).
3. Change my loop: lead with “What am I missing?”, escalate blockers early, give air cover to evidence over ego.

Teams don’t leave because of bad code.
They leave because promises get broken and expertise gets dismissed.

AI can generate code. It can’t generate trust.

What’s one promise you’ll keep this week that your team can actually feel?

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My friend Eric turned down a conference speaking slot.

Not because he was busy. Because he "wasn't expert enough."

Here's what happened:

Conference organizer emails him: "We want you to speak about scaling customer success teams. You went from 5 to 50 people in 18 months. That's what our audience needs."

Eric's brain: "There are people with way more experience than me. I'll look like a fraud."

The organizer: "We're not looking for the person with the most experience. We're looking for someone who just did this and can share what actually worked."

He turned it down anyway.

Six months later, he's watching someone else give a similar talk. Using the strategies Eric had figured out. Getting applause for the same insights Eric learned having done the work.

That's when he realized: Imposter syndrome doesn't protect you from failure. It protects you from success.

Here's what I've learned about getting past the fear of judgment:

It's not actually about other people judging you.
It's about you judging yourself. And projecting it onto everyone else.

→ The "2-Year Rule": If you're two years ahead of someone on a topic, you're expert enough to help them. Stop comparing yourself to people 20 years ahead. That's not your audience anyway.

→ The "Scared = Ready" Signal: The opportunities that terrify you are usually the ones you're most prepared for. Comfortable means you're not growing. You're repeating.

→ The "Bad First Draft" Permission: Your first attempt at anything won't be your best. But it will be better than the perfect version you never start. Done beats perfect. Every single time.

Eric eventually spoke at a different conference.

Stumbled twice. Forgot a slide transition. Sweated through his shirt.

Solid round of applause. Three people told him it changed how they approach team scaling.

The breakthrough wasn't confidence. It was doing it scared.

Your imposter syndrome is lying about two things:

- You're not ready. (You probably are.)
- People are judging you harshly. (They're mostly rooting for you.)

What opportunity are you talking yourself out of because you don't feel "expert enough"?

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Two leaders. Same deadline. Same pressure.

Leader A: Eight weeks of planning meetings. Still no progress.

Leader B: Shipped week one. Messy, imperfect, working.

Six months later:

Leader A: Gone.

Leader B: Running a 20-person team.

Here's the difference:

High performers don't wait for perfect clarity. They build while figuring it out.

What separates them:

They start before they're ready.

They decide with 60% of the information.

They ship messy over waiting for perfect.

They turn complaints into business cases: "This takes 45 minutes" becomes "we're losing $$$ daily."

They own gaps: "I need to learn this" not "my team can't do this."

The brutal truth:

Analysis paralysis looks like diligence. It's actually fear wearing a professional mask.

Your career doesn't reward perfect preparation.

It rewards decisive action.

Leader A waited for permission. Leader B asked for forgiveness.

One strategy builds careers. The other ends them.

What did you start before you felt ready?

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