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.

A VP of Engineering told me a few months ago: "I'm thinking about quitting leadership and going back to being a senior engineer."

Fifteen years of experience. Ready to walk away.

Not because he was failing. Because he couldn't see himself succeeding anymore.

Here's what he said:

"Every day is fixing what's broken. Mediating conflicts. Explaining delays to executives. Watching my team struggle. I don't remember the last time I felt good about what I'm building."

I asked him: "What went right this week?"

Long pause. "I... don't know. Nothing major. The usual fires."

"Okay, what small thing worked?"

Another pause. "Jennifer caught a security flaw in code review before it hit production. Saved us from what could've been a nightmare."

"Did you tell her?"

"No. It's her job."

That's the trap.

Tech leadership without gratitude isn't just exhausting. It's invisible progress wrapped in constant crisis.

You're solving complex problems. Managing people solving complex problems. Every win gets buried under the next fire.

Here's what changed for him:

I gave him one practice: Every Friday, document three moments that almost went unnoticed but mattered.

Week 1:
Junior dev caught logic flaw that would've broken invoicing
Team shipped hotfix in 20 minutes (used to take 2 hours)

Week 2:
Engineers pushed back on impossible timeline. He backed them. Project got realistic scope.
2 AM production incident—three timezones collaborated, fixed it fast, nobody panicked
Customer emailed: "Your API change saved us hours of manual work daily"

Week 3:
He texted me: "I'm not quitting. I was measuring the wrong things."

The shift:

He stopped counting problems solved. Started counting capabilities built.

Gratitude isn't forced positivity. It's recognizing what's working before burnout blinds you to it.

Three practices that kept him from walking away:

- Catch micro-wins in real time. Screenshot that Slack thread where your team solved something impossible. Save the customer email. Take a photo of the whiteboard after a breakthrough.

You'll need proof that progress is happening during weeks when everything feels broken.

- Tell people when you feel it, not when you schedule it. Don't wait for quarterly reviews. 

Someone saves the deployment? Tell them now. 

Peer covers your meeting during an outage? Acknowledge it immediately.

Gratitude expires. Don't let it spoil in your head.

- Turn complaints into capability gaps worth solving.

Tech leadership without this becomes a grind that burns out good leaders and fragments good teams.

With it? You stay clear-headed enough to see what's working while fixing what isn't.

That VP? Still leading. Team growing. Hasn't mentioned quitting again.

Not because the fires stopped. Because he can finally see the progress between them.

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Phillip R. Kennedy

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

The CFO cuts you off mid-sentence: "This infrastructure thing seems expensive. Can't we just use the cloud?"

You've spent three weeks modeling costs. Built a detailed TCO analysis. Documented every tradeoff.

He hasn't read any of it.

Different meeting. Same pattern.

The CEO interrupts your update: "Wait, six months for this? My nephew built an app in a weekend."

Your nephew built a to-do list with no users, no security, and no database. We're rebuilding an inventory management system processing $40M annually.

You don't say that. You just feel your credibility evaporating.

Third meeting, here we go again.

A VP dismisses your security recommendation: "We've never been hacked before. Why spend money on problems we don't have?"

The reason you've never been hacked is because you've been lucky and small. You're about to be neither.

Again, you don't say it. You just wonder if maybe you're overcomplicating things.

Then the doubts creep in:

Maybe I'm being too technical. Maybe I don't understand the business. Maybe they're right and I'm wrong.

That voice. It gets loud when smart people treat your expertise like an opinion.

Here's what I learned after many years of this:

When someone dismisses your expertise, they're not necessarily judging your competence.

They're managing their own discomfort.

The CFO doesn't understand infrastructure scaling. So, he reduces it to a cost problem he can control.

The CEO can't grasp technical complexity. So, he shrinks it to something familiar.

The VP can't see invisible risks. So, he pretends they don't exist.

None of this is about you.

It's about the terrifying gap between what they understand and what their business depends on.

You're living in that gap. They're denying it exists.

What actually works:

Translate without dumbing down. 

Pick your battles. Not every dismissal needs a defense. Some people just need to feel smart.

Document everything. When the thing you warned about happens, your Slack message from six months ago becomes very valuable.

Find allies who understand. One CTO or technical board member who gets it is worth ten executives who don't.

The truth most technical leaders need to hear:

You're not too technical. They're too scared to admit they're lost.

You're not overcomplicating it. They're oversimplifying what they don't understand.

You're not bad at business. They're bad at understanding that technology is their business.

The strongest tech leaders I know:

They stopped letting dismissal become self-doubt.

They trust their expertise even when it's not validated by people who can't evaluate it.

They know the difference between being wrong and being misunderstood.

What technical decision did you make that seemed "too expensive" until it prevented a disaster?

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I had a great engineer quit with two weeks' notice.

Exit interview: "I've been struggling for three months. You never asked."

I thought I was managing well. Checking sprint progress. Reviewing code. Clearing blockers.

What I missed: He'd been submitting PRs at 2 AM for six weeks. Stopped asking questions in standups. His code reviews went from thoughtful to "LGTM."

I saw all of it. Just didn't see what it meant.

Here's what I got wrong:

I tracked the work. Not the person doing it.

His velocity looked fine. Features shipped. Dashboard green.

So, I assumed he was fine too.

He wasn't.

A senior dev had trashed his code in a public review. Called it "junior mistakes." He'd been working nights trying to prove he belonged.

Three months of that. I never noticed.

The cost:

- Lost a strong engineer who would've become a tech lead.
- Lost credibility with the team who watched him burn out.
- Lost the right to say "we care about people" without sounding like bs.

What changed how I lead:

Stopped asking "How's the sprint?" Started asking "How are you actually doing?"

Different question. Different answer.

The signals I now watch for:

Work happening at weird hours. Not deadlines. Just... happening.

Contributors going quiet.

"I'm fine" delivered too fast.

Code quality consistent while everything else deteriorates.

The shift:

Your job isn't maximizing output. It's noticing when someone's drowning before their metrics drop.

Because by the time dashboards show problems, you've already lost them.

What actually works:

Notice patterns before asking. "You've been committing at 2 AM for two weeks. What's going on?"

Reserve 1:1s for conversation. Status updates belong in Slack.

Block unrealistic timelines before they hit your team.

Say this: "Your value isn't measured in story points or a tally of your lines of code."

The truth most leaders miss:

Empathy isn't soft. It's pattern recognition applied to humans.

You notice when deployments degrade. Notice when people do too.

Six months later, I saw him at a conference.

He's thriving. Tech lead now. Building something he cares about.

He was gracious. Said it wasn't personal.

But here's what he didn't say: I failed him. Not as a manager. As a human who should've noticed.

That changed how I lead. Forever.

What signal are you missing right now?

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I watched the best CTO I knew lose three senior engineers in six months.

Not because he was bad at technology. Because he was too good at it.

Here's what happened:

Production outage. Database corruption. Critical customer data at risk.

His senior engineer was on it. Diagnosing the issue. Ten minutes from a solution.

The CTO couldn't help himself. Jumped in. Took over. Fixed it in five minutes.

Everyone celebrated the quick save.

Except the senior engineer. Who quit two weeks later.

Exit interview: "I can't grow when you solve every hard problem before I get the chance."

That's when I learned:

Being the smartest person in the room is a liability when you're supposed to be leading it.

The difference between expertise and leadership:

Expertise says: "I can fix this faster."
Leadership says: "How do I help you fix this?"

Expertise hoards the hard problems.
Leadership distributes them strategically.

Expertise creates hero moments.
Leadership builds capable teams.

The shift:

Stop proving you're still technical. Start proving you can make others technical.

That CTO? Still brilliant. Still codes circles around everyone.

Now leads a team of two. Because the best people left to work for someone who'd let them grow.

Your technical expertise got you the job. But it becomes your ceiling if you can't let go.

What's one technical problem you solved that you should've let someone else own?

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(99+) Phillip R. Kennedy | LinkedIn

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Talks about #tech, #scaling, #leadership, #teamculture, and #waysofworking

I studied five disciplines in college.

Computer Science. Physics. Aerospace Engineering. Accounting. Finance.

My professors thought I couldn't commit. My advisor said I was "academically unfocused."

Twenty years later, that lack of focus is why companies hire me.


A CTO asked me last month: "I spent four years studying Computer Science. Why do I spend most of my day in budget meetings talking about ROI?"

I told him the truth: "Because that's the only reason you're still relevant."

The tech leaders getting replaced? They only speak code.

The ones getting promoted? They speak business.


For thirty years, we told people to specialize. Pick one thing. Go deep, not wide.

That advice just expired.

AI writes code better than most developers. Generates designs faster than most designers. Analyzes data more thoroughly than most analysts.

The specialist's advantage is disappearing.

What's becoming more valuable:

The CTO who understands cash flow gets budget approved. The one who only speaks architecture gets cut.

The VP of Engineering who grasps operations builds systems that solve real problems. The one who optimizes for technical elegance builds expensive things nobody uses.

The tech director who understands people keeps her team. Others lose people to burnout.


AI handles specialist work. Code generation. Data analysis. Design iteration.

Humans handle translation. Between what's technically possible and financially viable. Between innovation and implementation. Between engineering excellence and business impact.

The people thriving aren't the deepest technical experts anymore. They're the ones who can sit in a board meeting and explain why a six-month infrastructure project matters to customer retention.

My "unfocused" education is now my competitive advantage.

I can architect systems. Model how they impact cash flow. And explain both to people who only care about outcomes.

That combination is what companies pay for. Not code. Translation.

Three areas that changed my career:

Financial modeling. Not "this costs X" but "this impacts gross margin by Y."

Organizational psychology. People don't resist change. They resist being changed.

Strategic planning. Technology without strategy is expensive automation.
The pattern I see:

The specialists are getting automated. The complete humans are getting promoted.

Because they connect things across domains that specialists can't see.

Twenty years ago, my advisor was right. I was unfocused.

Today, that's why companies hire me as a fractional CIO.

Not because I'm the best coder or deepest architect. Because I translate between disciplines. And that translation is what executive teams need.

The depth gets you in the room. The breadth keeps you there.

What skill outside your specialty has made you more valuable?

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Three junior engineers asked me the same question recently: "Should I be worried AI is going to take my job?"

The panic in their voices wasn't about technology.

It was about the hype machine.

Here's what I told them, and what every tech leader needs to hear:

AI is genuinely powerful. It's also dangerously overhyped.

The gap between promise and reality is crushing teams.

The reality gap:

Your marketing team wants AI to "personalize all customer communications."

Reality: You spent three months building a system that still requires human review for every email because it keeps getting the tone wrong.

Your CEO read that AI will boost developer productivity by 40%.

Reality: Your team is debugging hallucinated code suggestions and spending more time reviewing AI output than writing from scratch.

Your board expects AI ROI in Q2.

Reality: You're still cleaning data from 2019 that the models need to actually work.

How to cut through the noise:

Start with pain, not technology.

Which manual process is crushing your team's time? Where are humans doing repetitive work that machines could handle?

Not: "Let's add AI to our product."
But: "Our support team spends 15 hours weekly answering the same 20 questions. Could AI actually handle that?"

Run quiet experiments first.

Spend two weeks testing if AI can improve your code review process. Measure it. Document what works and what doesn't.

Then, only then, announce it to the board.

Measure business impact, not AI adoption.

"We use GPT-5" means nothing.

"AI reduced our documentation time by 30% while improving quality" means everything.

Budget for reality.

AI projects take 3x longer than initial estimates because integration is always harder than the demo.

The nuanced truth:

AI excels at specific, bounded tasks. Code completion. Document generation. Data analysis. It genuinely helps here.

But it fails at strategy, complex reasoning, and anything requiring deep business context that only your team understands.

Your job isn't to dismiss AI or chase every breakthrough.

It's to evaluate tools based on real business problems and team capacity.

The best tech leaders I know are quietly using AI where it works and ignoring the hype everywhere else.

Six months from now:

Half the "AI-first" companies will be quietly removing features that never worked.

The leaders who succeeded will be the ones who asked: "Does this actually solve a problem worth solving?"

Not: "Are we doing enough AI?"

What AI pressure are you getting from leadership right now?

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I quit. 

Two different managers.

Same conversation. Two different reactions.

One ruined the relationship forever. One made it stronger.

Manager A (let's call them Steve):

"I've accepted another role."

Five seconds of silence.

"After everything we invested in you?"

He stopped including me in meetings. Stopped responding to messages. My last day, two-line email: "Thanks. Good luck."

That was 8 years ago. Haven't heard from him since.

Manager B (let's call them Patty):

"I've accepted another role."

"Tell me about it."

She asked good questions. Then: "This sounds right for you. How can I help?"

She made introductions. Wrote my LinkedIn recommendation without asking. Made my transition smooth.

Last day, lunch: "Stay in touch."

Years later:

Steve? I cross the street at conferences.

Patty? First call when I need advice. Three referrals sent her way. When she needed help, I cleared my calendar.

Here's the thing:

How you handle someone leaving tells them everything about whether you saw them as a human or a resource.

Steve treated departure as betrayal.

Patty treated it as transition.

The math:

Steve protected his ego for two weeks. Lost a relationship that could've compounded for decades.

Patty invested two weeks in a graceful exit. Gained an advocate, referrals, and ongoing collaboration.

Same person. Same situation. Different choice.

The cost of treating departure like betrayal:

You burn a relationship that could've compounded for decades over ego protection that lasts two weeks.

Steve lost:

- Any chance I'd refer candidates to him
- Any future collaboration opportunities
- My willingness to be a reference for him
- Access to my network

Patty gained:

- Three senior engineer referrals
- Ongoing advisory relationship
- Someone who promotes her leadership publicly
- Access to my clients when it makes sense

What I learned:

People leave. Average tenure is 2-3 years. That's not betrayal. That's reality.

The question isn't whether they'll leave.

It's whether they'll want to stay connected when they do.

Your reputation as a leader isn't built on who you hire.

It's built on who still calls you after they leave.

Steve chose ego. Patty chose compound interest.

I know which one I want to be.

Which manager have you experienced?

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A CEO once asked me: "How do you stay so confident when you don't know the answer?"

I'd just told him "I have no idea if this migration will work."

He looked confused. "Then why are you recommending it?"

Here's what I learned about confidence:

It's not knowing the answer. It's knowing you can find it.

Think of leadership confidence like jazz improvisation. The best players don't memorize every note. They trust their ability to respond to whatever the other musicians play.

Bad leaders treat uncertainty like a secret to hide.

They memorize buzzwords. Study frameworks. Pretend they understand every technical detail their team mentions.

Then freeze when something breaks that isn't in the playbook.

Great leaders treat uncertainty like terrain to navigate.

They don't pretend to know the route. They just trust they can read the map.

The shift:

Stop trying to be the expert on everything. Start being the person who knows how to make progress with incomplete information.

What that actually looks like:

You say "I don't know, but here's how we find out" instead of nodding along pretending you understand.

You ship decisions with 60% of the data instead of overthinking for two weeks when it's too late.

You ask "Does this solve the customer problem?" before "Is this technically elegant?"

You tell your team "I was wrong about the approach" instead of quietly pivoting and hoping nobody notices.

The uncomfortable truth:

Your team already knows you don't have all the answers.

Pretending you do doesn't build confidence. It shatters trust.

Real confidence is this:

Production crashes at 2 AM. Your team is looking at you.

And your lack of panic is not because you know all the answers.

You're calm because you trust yourself to figure out what matters, assemble the right people, and make the call that moves everyone forward.

That's the confidence that builds careers. And teams that follow you into problems nobody's solved before.

What's one time you gained respect by admitting you didn't know something?

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A CEO asked me: "How do we keep our remaining teams loyal after the layoffs?"

I stared at him.

"You just cut 10% of their friends to hit quarterly numbers. And now you want loyalty?"

Here's the math:

Trust is earned in drops. Lost in buckets.

You can't unring that bell. But you can be the reason people stay anyway.

What happened next:

I walked into our team meeting the next day.

No corporate speak. No "this was necessary for the business."

And said: "I know you're scared. I know you're angry. I know you're updating your LinkedIn. I get it."

Then: "Here's what I can control. And what I can't."

What we couldn't control:

- The company's decision
- The budget cuts
- The uncertainty

What we could control:

- Defending the team from the next round of cuts
- Being honest about business reality without creating panic
- Seeing them as humans, not headcount

Six months later:

The team? Fully intact. Other departments lost more of their people to voluntary attrition.

Same company. Same uncertainty. Different leader.

Here's what most leaders miss:

Acknowledge the grind, not just the wins. Call out the 2 AM production fix. The boring migration nobody celebrated. Make people feel seen for their struggle, not just their output.

Shut down the rumor mill fast. When someone asks "Are we next?" don't deflect. Be honest and explain the reality of the situation and business needs. Crush the panic before it spreads.

Tell the truth. "Revenue dropped 20%, budgets are tight" beats "everything's fine" when people can read the company Slack. Adults handle truth. They can't handle being lied to.

Actually manage workload. Push back on impossible timelines. Stop projects that would burn people out. Your flexible schedule doesn't mean your team has unlimited capacity.

Fund their growth even when it meant losing them. Conference approvals. Certifications. LinkedIn introductions. People stay longer with leaders who invest in their future, even if that future isn't here.

Remember they're humans. Kids with soccer games. Parents in hospitals. Life outside of their email. The leader who says "family first" and means it builds loyalty that survives stock drops.

The shift:

Your company might not deserve their loyalty.

But you can be the reason they stay anyway.

In a world where people are line items on spreadsheets, being the leader who sees them as humans isn't just good management.

It's how you win.

What's one way you kept your team together when everything was falling apart?

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Being easy to work with costs nothing.

But it's the difference between being seen as a technical resource and trusted as a strategic partner.

I watched a technically brilliant CTO get passed over for a board seat. Not because he couldn't architect systems. Because nobody wanted to sit in meetings with him.

Here's what actually separates leaders people want to work with:

They explain complexity without condescension.

"The API integration is complex because we're bridging legacy data formats" not "This is way above your pay grade."

They give options, not ultimatums.

"We can ship fast with technical debt or take two weeks to build it sustainable. Here's the tradeoff" beats "This will take six months, no discussion."

They admit when they're wrong.

"I underestimated the database migration complexity" instead of quietly moving goalposts every week.

They translate business needs into technical solutions, not force technical solutions onto business problems.

They show up prepared to listen, not just defend their team's capacity.

Think of it like system design:

You can build the most elegant architecture in the world. But if it's not accessible and maintainable, nobody wants to use it.

Same with leadership.

The upside of being easy to work with:

You get invited to strategic conversations before decisions lock in. The CEO asks for your input on acquisitions. Your budget requests get approved faster. The board sees you as business-critical, not just technically necessary.

The cost of being difficult:

You get excluded from planning sessions. Your team gets blamed for delays. You're seen as a bottleneck, not an enabler. Your technical expertise becomes irrelevant because people avoid working with you.

The brutal truth:

Your code doesn't attend board meetings. You do.

Your architecture doesn't negotiate with vendors. You do.

Your systems don't build relationships. You do.

People don't just hire technical skills. They choose leaders they want to partner with for the next three years of growth, challenges, and impossible deadlines.

Being easy to work with isn't about being a pushover. It's about being someone others can build with.

What's one thing that makes a tech leader easier to work with?

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A former colleague texted me last week: "Remember when I turned down that role three years ago because I didn't feel ready?"

I did remember. VP position. Startup scaling fast. 20% pay bump. She said no because her current company felt "safe."

"Just accepted a similar role. Same level. Same pay. Except now I'm three years older with the same skills I had then."

That's the real cost of comfort.

Not what you lose by taking the risk. What you lose by not taking it.

Here's what staying comfortable actually costs you:

- The confidence you could've built by figuring things out.
- The skills you would've developed by being slightly in over your head.
- The network you would've grown by working with people ahead of you.
- The salary growth that compounds when you make moves at the right time.

Three years later, she got the same opportunity. But the gap between who she was and who she could've been was now visible. Measurable. Painful.

The shift:

Growth doesn't wait for you to feel ready. It rewards people who move before they're comfortable.

Think about it: Every skill you have now came from doing something you weren't qualified for yet.

- Your first leadership role? You weren't ready.
- Your first big project? You figured it out.
- Your current position? You grew into it.

But here's what happens when you stay too long:

You stop growing and start defending. Defending your current skills. Your current role. Your current comfort zone.

The people who passed you? They didn't wait to feel ready. They just moved.

What the best professionals know:

Growth beats comfort. Every time.

Not because growth is easy. Because comfort has an expiration date in a world that's changing this fast.

- Your skills aren't getting better by staying still. They're getting obsolete.

- Your confidence isn't building by playing safe. It's eroding.

- Your career isn't strengthening by staying loyal to one place. It's calcifying.

The brutal truth:

The role you're "not ready for" today becomes the role you're "overqualified for" tomorrow, if someone else takes it and grows into it while you wait.

Three years from now, you'll either look back and think "I'm glad I stayed" or "I wish I'd left sooner."

Very few people regret taking the growth opportunity. Most regret waiting for permission that never comes.

Here's the question that matters:

Are you staying because you're still growing? Or because leaving feels uncomfortable?

One builds your future. The other protects your ego.

What opportunity are you waiting to feel "ready" for?

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The CTO cuts off the engineer mid-sentence: "We already evaluated that framework. Not a fit."

The engineer was about to explain how that "not a fit" framework just helped their competitor ship the same feature in three weeks instead of three months.

But the conversation was already over.

Not because the CTO was protecting bad code. Because he was protecting his ego.

Technology changes every 18 months. If you stop learning, you don't plateau. You become expensive legacy infrastructure.

The highest-performing technical leaders I know aren't always the smartest people in the room.

They're the most teachable.

Being right protects your reputation today. Being teachable compounds your value for decades.

What teachable actually looks like:

A CTO I work with joined his team's architecture review. Didn't lead it. Just listened.

Afterward: "I realized I didn't understand half of what they discussed. I've been making decisions based on five-year-old knowledge."

He spent three months relearning modern architecture. Not to prove he was still technical. To make better decisions.

The pattern I see:

The CTO who says "we already evaluated that" stops learning. His team stops bringing him ideas. Innovation moves around him, not through him.

The CTO who says "tell me what changed since we last looked at this" keeps learning. His team brings him everything. Innovation flows through his decisions.

One becomes a bottleneck. The other becomes a multiplier.

Here's what the teachable ones do differently:

They admit ignorance before defending outdated positions. When quantum computing or new AI capabilities come up, they say "I need to learn more about this" instead of dismissing what they don't understand.

They learn business as intensely as they once learned algorithms. They join customer calls. Study P&Ls. Shadow sales.

They schedule time to not know things. Two hours weekly exploring what they don't understand. 

They make "I don't know" their competitive advantage. Their teams trust honest uncertainty more than confident ignorance.

The shift:

Stop defending what you know. Start exploring what you don't.

Your value as a technical leader isn't what you knew five years ago. It's how fast you can learn what matters now.

The questions that matter:

What technical area are you defending instead of exploring?

What framework did you dismiss that you should revisit?

What conversation are you cutting off because it threatens what you think you know?

The leaders I remember:

They weren't the ones who were always right. They were the ones who were always learning.

They're all still relevant. Still leading. Still valued.

Because they chose being teachable over being right.

What are you choosing?

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The board meeting is going fine until the top investor brings someone new.

"This is Marcus. Technical advisor. He'll be helping us evaluate the platform."

David, the CTO, wasn't told this was happening.

Marcus starts asking questions. Polite at first. Then sharper.

"Why are you building your own authentication instead of using something off-the-shelf?"

"This database architecture won't scale past 100K users."

"Your AWS costs seem high for your user base."

Every question implies: You don't know what you're doing.

Here's what David didn't do:

Get defensive. Jump in with justifications. Defend every decision point by point. Treat Marcus like an adversary. Make it about winning the argument instead of finding the truth.

That's what most CTOs do. It's why most don't survive this situation.

Here's what David did instead:

Stayed quiet while Marcus listed every issue. Took notes. Didn't defend anything.

When Marcus finished: "Those are fair questions. I'd like to schedule time with you this week to walk through our architecture decisions and the context behind them. Some of these concerns are valid. Some are based on constraints you might not be aware of yet."

Then to the board: "I appreciate technical oversight. Marcus, I'll send you our architecture docs tonight. Let's meet Thursday."

Three weeks later, David and Marcus presented a joint recommendation to the board.

Half of Marcus's concerns were valid. David was already implementing fixes.

The other half were based on misunderstanding the business requirements. Marcus now understood why those decisions were made.

The board's confidence in David went up, not down.

What separated David from CTOs who don't survive this:

He separated his ego from his architecture. "I made these decisions" doesn't mean "these decisions were right."

He treated questions as information, not attacks. When someone questions your work and your first instinct is defensiveness, they've usually touched something true.

He made Marcus an ally instead of proving him wrong. "Let's figure this out together" beats "let me show you why you're mistaken" every time.

Six months later, when the board questioned a major infrastructure investment, Marcus defended it:

"I've reviewed their technical strategy extensively. This is the right move."

The pattern:

Leaders who can't separate ego from work become their work's biggest bottleneck.

When every question feels like an attack, you stop getting the information you need to lead well.

The cost isn't just the bad decisions you defend. It's all the good information you never get because people learn you can't handle it.

What's your default when someone questions your work?

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Six kids. One baseball. Pure chaos.

I'm watching my son's 6-and-under game when a grounder rolls into the infield.

All six kids abandon their positions and sprint toward the ball like it's the only thing that matters.

They pile on. Someone emerges triumphant, holding the ball high.

Problem? Nobody's covering any base. The runner could walk home, grab a snack, and still be safe.

The kids don't care. They're laughing.

Later, my son strikes out on five swings. His reaction? Beams and jogs to the dugout. Happy to hang out with his friends.

The score? Nobody's tracking it. Outs don't matter. The outcome is irrelevant.

Here's what hit me:

These kids naturally understand something most executives have completely forgotten.

They're optimizing for the right thing.

- Not the outcome. The experience.
- Not the metrics. The moment.
- Not performance. Presence.

Now contrast that with how most companies operate:

Everyone chasing the same metric. Piling on the quarterly goal. Obsessing over the scoreboard while ignoring whether anyone's actually covering the bases that matter.

The pattern:

We optimize for metrics that are easy to measure. We forget to optimize for things that actually matter, like whether people are engaged, learning, or finding meaning in the work.

The shift:

Those six-year-olds aren't ignoring the game. They're just playing a different one.

They're optimizing for: Am I having fun? Am I with people I like? Am I fully in this moment?

What if your team did the same?

Not ignoring outcomes. But asking: Are we optimizing for metrics or for meaning?

Three things the kids taught me about leadership:

1. Presence compounds. 

My kid who struck out? He's building connection with his teammates. 

Your team hitting their sprint velocity? That's output. It doesn't compound into loyalty or innovation unless people care about what they're building.

2. When everyone chases the same goal, nobody's covering the important work.

Six kids on one ball. Zero kids covering bases.

Ask: What critical work isn't getting done because everyone's chasing the visible goal?

3. Joy in the process is a competitive advantage.

Teams that enjoy the work outperform teams grinding through it, not because they're slacking, but because they're present, creative, and resilient when things get hard.

The question:

What are you optimizing for?

Metrics everyone can see? Or meaning that actually sustains people?

Both matter. But if you only measure one, you're abandoning the bases that win the game.

Those six-year-olds? They'll learn to keep score eventually.

But I hope they never forget: The joy is in showing up fully, not in what the scoreboard says.

What's one metric your team obsesses over that might be making you miss what actually matters?

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The database crashes at 2 AM Saturday morning. Two senior engineers get the alert.

Engineer A (Tom) is brilliant. Diagnoses the root cause by 3 AM. Architects a perfect solution. Goes silent for 36 hours building it.

Engineer B (Evan) is reliable. Posts in Slack at 2:07: "Database down. Investigating." At 2:45: "Found the issue. Implementing workaround." At 3:15: "System back up. Full fix by Monday."

Six months later, Evan becomes the tech lead.

Not because he was smarter. Because everyone knew exactly where they stood with him.

Here's what changed in the last five years:

Being the smartest person in the room used to be enough. You knew the most. You solved the hardest problems. You got promoted.

That playbook is expiring.

ChatGPT writes decent code. Stack Overflow has the answer for most common problems. Documentation exists for nearly everything. Information is abundant now.

Reliability is what's scarce.

Your CEO doesn't care if you know the latest framework. They care that you deliver what you promised when you promised it.

Your team doesn't need you to architect perfect systems. They need you to unblock them before they lose momentum.

Your customers don't always need cutting-edge technology. They need systems that work when they're placing orders.

What reliable actually looks like:

I worked with a tech lead who wasn't the strongest technical person on his team. Three engineers were better architects. Two were faster coders.

But when stakeholders needed to know if something would ship on time, they asked him. When the team hit a blocker, they pinged him first. When executives needed technical updates, they trusted his word.

Why? Because in two years, he'd never missed a commitment. Never left someone wondering. Never went dark when things got hard.

His reputation wasn't built on brilliance. It was built on 32 small moments of showing up:

Responding to code reviews within four hours. Every time.

Updating the team when deployments ran late. Before anyone asked.

Being in the difficult architecture discussions. Not disappearing when decisions got uncomfortable.

Closing every loop. That performance issue didn't vanish into a backlog. It got resolved, escalated, or explicitly deprioritized with context.

That's the shift:

The smartest person used to win. Now the most dependable person wins.

AI can handle more of the brilliant technical work every day. But it can't build the trust that makes teams perform under pressure.

It can't show up to the 4 PM Friday meeting when a junior engineer needs guidance.

It can't translate "intermittent 500 errors" into business language during an executive call.

It can't be the person everyone knows they can count on.

Which reputation are you building?

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