CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Every week I tackle management, operations & startup topics that are helping 250,000+ people. Sign up free: www.scotchisholm.com

I also run a leadership accelerator that helps founders develop into top CEOs. Apply here: https://joinhighland.com/apply/

My backstory: 

🚀 Founder of Classy, SaaS for nonprofits raising billions per year

🎗️ Acquired by GoFundMe in ‘22 to create largest giving platform in the world

🌲 Investor in dozens of startups out of family fund, Tall Timbers Holding Co, (Ripple, FanDuel, Hubble, Casetext, etc.)

🏔️ Founder of Highland, leadership accelerator & community for founders

🏡 Co-founder of Haskill Creek, modernized & healthier version of a Walgreens or CVS 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland & food 

⚙️ Industrial engineer & lean six sigma nerd, UMass Amherst grad 

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation

It's been a wild ride. If you're interested in any of the above, please visit my website and reach out to me there. 

www.scotchisholm.com

Scot Chisholm

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

"I don't understand half of what you just said. Walk me through it."

The room went quiet.

A VP with twenty years of technical credibility had just admitted to three engineers in their twenties that he couldn't follow their conversation.

They'd been whiteboarding an AI implementation. The technology his company was betting its future on. And he was lost.

He had a choice in that moment.

Nod along. Ask questions designed to sound informed. Make architectural decisions based on instinct about technologies he didn't understand.

I've watched plenty of leaders take that path. Their teams learn to route around them. They become the bottleneck nobody can explain things to.

This VP chose differently.

"Walk me through it."

One engineer grabbed a marker. Started over. Simpler. The others jumped in, translating.

Fifteen minutes later, the VP understood enough to ask different questions.

Not "how does the embedding model work?"

"What breaks first if we're wrong about scale?"

"Where do we need expertise we don't have?"

"What's the simplest version that proves this works?"

Strategic questions. The kind twenty years of experience actually prepared him for. The kind his team couldn't answer alone.

Something shifted after that meeting.

Those engineers started bringing him problems earlier. They stopped working around him. They trusted his judgment on business decisions because he'd been honest about his technical gaps.

Here's what most leaders miss:

Admitting ignorance isn't weakness. It's an invitation.

It tells your team: I need you. I can't do this alone. Your knowledge matters more than my title.

That creates loyalty no expertise can buy.

The VP told me later: "I spent twenty years building credibility by knowing things. That one moment of admitting I didn't know built more trust than all of it combined."

AI moves too fast for anyone to stay the expert.

The leaders who are thriving have stopped trying.

Their credibility isn't "I know more than you."

It's "I know what I don't know. And I'm curious enough to learn from whoever does."

Your team doesn't need you to understand every new technology.

They need you honest when you don't.

That's the new technical credibility.

♻️ Repost and comment if you've seen this in action

➕ Follow me (Phillip R. Kennedy) for more on leading through shifts nobody trained you for

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

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

I thought I was helping.

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

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

Then I noticed something.

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

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

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

That landed like a punch.

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

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

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

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

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

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

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

But here's what changed when I did:

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

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

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

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

I build less now. We ship more.

Trust scales better than talent.

I wish someone had told me that three years earlier.

♻️ Repost and comment if you've made this shift

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

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• 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 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

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

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

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

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. 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

EDI Manager / Systems Administrator

The qualities that get tech leaders promoted have almost nothing to do with the qualities that make people want to follow them.

Technical excellence. Architectural knowledge. Delivery track record. That's what gets you the title.

But I've watched brilliant architects with empty teams. And average engineers with people lining up to work for them.

The difference comes down to three things.

They see you.

Not your output. You.

A VP I worked with had a habit that seemed small. When an engineer started explaining something, he'd close his laptop. Mid-sentence. Every time. Full attention.

An engineer told me later: "He's the first leader who actually listened. Not waiting to respond. Actually listening."

Presence is a choice to treat someone's time as worthy of your full attention.

Most leaders fail here because the structure works against them. Forty direct reports. Back-to-back meetings. Slack notifications competing for every second. Presence requires fighting the current.

The leaders people admire fight it anyway.

They protect you.

From chaos. From blame. From pressure that isn't yours to carry.

A Director of Engineering I know never let her team hear about executive drama. When the CEO demanded an impossible timeline, she pushed back in rooms they'd never see. When the deadline held, she negotiated scope in ways they'd never know.

Her team thought projects just had reasonable timelines. They had no idea what she absorbed to make that true.

When the deployment failed, she owned the process publicly. When it succeeded, she named the engineer who fixed it.

Credit flows down. Blame stops with her.

Most leaders fail here because protection is invisible. The executive who pushes back looks like an obstacle, not a guardian. The performance review doesn't have a line for "shielded team from organizational chaos." The incentive structure punishes protection.

The leaders people admire do it anyway.

They lead somewhere.

Clarity about where you're going. Decisiveness when paths diverge. Courage to choose the unpopular route.

Engineers don't need leaders who know every technical answer. They need leaders who can say "we're going this direction" and mean it.

A CTO I respect canceled a feature three weeks before launch. Product was furious. Sales had already promised it. But his engineers were drowning and shipping it would have broken them.

He took the heat. They kept their weekends. And their respect for him compounded.

Most leaders fail here because decisiveness requires vulnerability. Choosing means being wrong publicly. Research feels safer than commitment. Consensus feels safer than direction.

The leaders people admire decide anyway.

Three things. See them. Protect them. Lead somewhere.

Technical skills get you the title.

These three determine whether anyone's glad you have it.

♻️ Repost and comment if you've worked for someone who did these

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

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

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

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

He never named the engineer.

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

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

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

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

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

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

If everything goes wrong, they take the blame.

Sound exhausting? It is. Sound thankless? Often.

So why do it?

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

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

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

Here's what I've learned:

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

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

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

It's a harder transition than any technology migration.

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

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

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

Leadership is a practice, not a position.

It's a choice you make every day.

Make it today.

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

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

Go ahead. Google yourself.

I'll wait.

If what came back was your LinkedIn profile, a 10K race result from 2019, and someone with your name who's a dentist in Ohio...

We need to talk.

A technical leader I worked with recently had this exact moment. Right before a career-defining interview, he searched his own name.

Three years rebuilding infrastructure. Millions of users. Zero downtime during migration. A team turnaround from 40% attrition to zero departures.

Google's take: maybe he's a dentist. Maybe he ran a 10K once. Hard to say.

All that work. Locked behind NDAs, internal Slack channels, and architecture docs that will never see daylight.

His company knew. His executives trusted him with everything. His scope kept expanding.

The market had no idea he existed.

Your best work is probably invisible.

The infrastructure that didn't break. The team that stopped quitting. The migration nobody noticed because it went perfectly.

That work builds your resume. But resumes are just claims. And claims require evidence.

When opportunity comes, and it will, can you tell the story of your career to someone who wasn't in the room?

Or are you asking them to trust you based on a LinkedIn profile and a strong handshake?

I know what you're thinking.

"Writing about myself feels gross. That's for people who care more about personal brand than actual work."

I get it. I really do.

But you know what feels worse? Watching someone with half your experience land the role because they have three blog posts and a conference talk. Not better skills. Just better evidence.

The market can't reward work it can't see.

It rewards clear thinking about problems it recognizes.

The technical leaders who move fluidly between opportunities aren't better at the work. They're better at making their thinking visible outside their current walls.

Not proprietary code. Principles. Not internal details. Lessons someone else can apply.

The framework you used to prioritize technical debt. The question that aligned executives on that investment. The mistake you made and how you recovered.

That's what travels.

You don't need to become an influencer. You don't need a podcast. You don't need to say "thought leader" unironically.

You need one searchable piece of evidence that you think clearly about hard problems.

Start today. Write about a decision you made. A lesson you learned. A principle that's guided your work.

Make it findable.

Because someday, someone will google you before deciding whether to take a chance.

Make sure they find more than a 10K time and a dentist in Ohio.

♻️ Repost and comment if you just googled yourself and felt attacked

➕ Follow me (Phillip R. Kennedy) for more on building a career that creates options

The answer to your biggest problem is sitting in someone's head three desks away.

They're not hiding it.

They just stopped telling you.

A VP called me last month. Deadlines slipping. Morale tanking. He'd tried new processes, better tools, more standups. Nothing worked.

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

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

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

The VP never heard it. Not really.

Here's what happened:

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

Engineer heard: "This isn't important."

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

One conversation. Two completely different memories.

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

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

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

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

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

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

They're not hiding information.

They've learned you're not really asking.

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

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

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

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

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

Then wait. Ten seconds of silence feels like forever.

That's where the truth lives.

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

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

His team worked weekends deploying code manually.

He spent those weekends reading blog posts about deployment tools.

Both felt like work. Only one was.

A Director of Engineering I worked with spent six months researching CI/CD solutions. Comparison spreadsheets. Vendor webinars. Architecture blogs. Slack threads debating GitHub Actions versus CircleCI versus a dozen other options.

"I want to make sure we choose the right solution," he told me. "This decision will impact us for years."

Meanwhile, his engineers were burning out on manual deployments. Bugs reached production because humans missed edge cases. Customer complaints piled up. Weekend after weekend after weekend.

But he felt productive. Every day brought new insights. Another framework to evaluate. One more expert opinion to consider.

This is what dopamine from information gathering looks like.

Your brain treats learning like achievement. Every article feels like progress. Every new tool feels like forward motion. The neurotransmitters are identical. Research and shipping feel the same.

Only one creates value.

Research feels like diligence. It feels responsible. Thorough. Professional. Engineers are trained to evaluate, analyze, optimize before committing. Shipping something imperfect feels like technical debt.

But you know what's actually technical debt?

Six months of manual deployments while you researched the perfect solution. The bugs that reached production while you read comparison matrices. The engineers who burned out while you attended webinars.

That's the real cost. And it's invisible because research never fails visibly. You can evaluate tools forever without ever being proven wrong.

Action fails visibly. That's why your brain prefers research. Research is safe. Action is vulnerable.

The Director's turning point came on a Saturday morning.

Another blog post about deployment pipelines. Phone buzzes. Production down. Manual deployment failed.

He stared at both screens. The article about solutions. The alert about the actual problem.

Something clicked.

Monday: GitHub Actions. Not perfect. Available now.

Three weeks later: automated deployments. Deployment time from hours to minutes. Weekend work gone. Engineers shipping twice as fast.

Six months of research. Three weeks of implementation.

The research felt like progress.

The implementation was progress.

The next time you find yourself "almost ready" to make a decision, ask yourself:

Is this diligence? Or is this hiding?

Your brain won't tell you the difference. Your calendar will. Check how many hours you spent learning versus shipping.

That ratio reveals everything.

♻️ Repost and comment if you've been the Director

➕ Follow me (Phillip R. Kennedy) for more on leading with a bias toward action

Five "URGENT" Slack messages before 10 AM.

Zero responses by noon.

The director thought his team was ignoring him. They weren't. They'd just learned that urgent meant nothing.

When everything is urgent, nothing is.

A CTO I worked with marked 28 items "high priority" in one quarter. His team delivered six. The other 22? Still sitting there. Still marked urgent. Still waiting.

An engineer on his team told me how they actually worked:

"We wait three days to see what he asks about again. That's the real priority."

Three days. That's how long it takes for your team to figure out what you actually mean.

The human brain can't stay in crisis mode forever. So it adapts. It develops an immune response. It learns to filter out the noise and watch for the signal.

The signal is what you follow up on. The noise is everything else you labeled urgent.

Your team isn't ignoring you. They're pattern-matching. And the pattern tells them most of this isn't actually urgent.

Here's the real cost:

When something actually IS urgent, they won't believe you.

The production outage that needs attention now. The security vulnerability that can't wait. You'll mark it urgent. They'll add it to the list of 47 other urgent things and wait for clarification.

That's the cost of crying wolf with your calendar.

A VP I know has a different approach. Simple rule: if it's not costing money, losing customers, or blocking work right now, it's not urgent. Might be important. Not urgent.

His team moves fast on the three things per quarter he marks urgent.

Because they know he means it.

Urgency is currency. Every time you spend it on something that isn't, you have less for when it is.

Most leaders are bankrupt and still writing checks.

If your team seems slow to respond to priorities, ask yourself:

How many things have you marked urgent this month?

How many actually were?

The gap between those numbers is exactly how much credibility you've lost.

You didn't train your team to be unresponsive.

You trained them that "urgent" means "wait and see."

♻️ Repost and comment if you've seen this pattern

➕ Follow me (Phillip R. Kennedy) for more on leading without losing your team's trust

Santa runs the most high-pressure operation on earth.

One deadline per year. Zero extensions. Billions of stakeholders expecting delivery within a single night. A production environment where one bug means a kid wakes up disappointed.

And somehow, the elves have been there for centuries. No turnover. No burnout posts. No LinkedIn updates about "exciting new opportunities at the Easter Bunny's warehouse."

What does Santa know that most leaders don't?

I've been thinking about this while watching tech leaders lose their best engineers to far less demanding workplaces.

Santa's workshop shouldn't work. The pressure is insane. The deadline is immovable. The scope keeps growing (have you seen the world population chart?). Every management consultant would predict a toxic culture.

Instead, they sing while they work.

Here's what I think Santa gets right:

He doesn't blame elves when toys break.

Somewhere in the workshop, an elf is going to mess up a bicycle assembly. Happens every year. Santa doesn't storm in asking "who broke the bike?" He asks "what's making bikes hard to build this season?"

Systems, not people. Every time.

He pairs the struggling with the skilled.

When a new elf can't figure out the latest gaming console, Santa doesn't assign them three more consoles to figure out. He pairs them with the elf who built last year's model.

Teaching isn't a punishment for the expert. It's an honor.

He protects the workshop from the North Pole's chaos.

Mrs. Claus needs the budget reviewed. The reindeer have opinions about flight routes. The media wants a statement about supply chain concerns.

Santa handles all of that. The elves never hear about it. They just build toys.

Pressure flows up, not down.

He checks in after the long nights.

Late November, the workshop runs around the clock. Santa doesn't show up on December 26th asking for productivity metrics. He shows up with cocoa asking how everyone's holding up.

He knows burnout shows up in toy quality long before resignation letters.

He celebrates the catches, not just the completions.

The elf who notices a design flaw before a million toys ship? That elf gets recognized. Finding problems is as valuable as solving them.

Prevention is invisible until you make it visible.

It's not magic that keeps the elves loyal. It's leadership.

They stay because someone has their back when the inevitable mistakes happen. Because pressure doesn't become blame. Because struggling isn't shameful. Because the leader absorbs chaos instead of distributing it.

This holiday season, ask yourself:

Would your engineers stay for centuries? Or are they quietly updating their LinkedIn profiles while you finalize their bonus?

The presents aren't what make Christmas magic.

It's knowing someone's got your back.

Happy holidays. Go be someone's Santa. 🎅

♻️ Repost and comment to spread some holiday leadership cheer

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You'd get paged at 2 AM if a service degraded 5%.

Your career could drift for five years. No alert. No dashboard. No incident review.

Just a slow Tuesday that turns into a slow decade.

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

Beautiful systems.

Then I asked about his career plan.

Long pause. Slight panic.

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

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

He laughed. Then stopped laughing.

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

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

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

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

You build alerting for services. Not for yourself.

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

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

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

It is insane. It's also normal.

What changes when you apply systems thinking to yourself:

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

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

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

Takes an hour every three months.

You build systems because drift is the default.

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

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

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

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Most tech leaders will finish this year where they started.

Same title. Same scope. Same invisibility.

Not for lack of talent. For lack of intention.

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

It doesn't.

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

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


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

Not networking. Conversation.

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

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

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


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

Not polished. Not strategic. Just captured.

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

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

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


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

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

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

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

Your team trusts you more because you stopped pretending.


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

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

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

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


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

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

Block it. Protect it like uptime.

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

Small numbers. Massive compound effect.

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

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

The ones who act will wonder why they waited.

Start this week.

♻️ Repost and comment if you're starting today 

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December is when your best engineers quietly update their LinkedIn profiles.

January is when you find out who was serious.

A VP called me last week. His best senior engineer just resigned. Six-figure equity. Top 5% salary. Full remote.

"I don't understand it. We pay better than anyone."

I asked one question: "What did his last month look like?"

Three weekend deployments. A post-incident blame session in a public Slack channel. On-call rotations unchanged in two years despite the team doubling.

"But we gave him a great bonus," the VP said.

You can't bonus your way out of burning someone out. There's no stock option that compensates for public humiliation. No equity that makes up for never protecting your team from pressure rolling downhill.

Comp tables don't build loyalty. How you treat people builds loyalty.

This time of year, people take stock. Not portfolios. Lives. They sit with family, get asked "how's work?" and hear themselves answer.

Engineers who feel protected come back energized.

Engineers who've been ground down come back with interviews scheduled.

What actually makes them stay isn't grand gestures. It's small ones, repeated:

Noticing burnout before it becomes resignation. Absorbing pressure so your team hears realistic timelines, not panic. Handling incidents without public blame. Treating personal time as non-negotiable.

None of this costs money. All of it is rare.

This season, everyone's handing out bonuses and gift cards.

Those are nice.

The real gift? Let them rest. Protect them from chaos. Make it safe to be human.

The engineers who stay don't stay for the comp package.

They stay because someone made staying feel worth it.

Be that someone.

♻️ Repost and comment if you're trying to be that kind of leader

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

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

If you struggled, so will your team.

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

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

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

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

That shift should concern every technical leader.

Here's why:

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

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

This isn't just Amazon.

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

The era of being valued for potential is ending.

Now you're valued for evidence.

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

Unless their leader helps them.

Here's what this means for you:

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

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

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

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

The Amazon article quotes their new guideline:

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

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

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

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

Make sure your team has a good answer.

Not because the game changed.

Because you taught them how to play it.

♻️ Repost and comment if your team needs to hear this

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I have been seeing this take going around lately:

Wake up: 6.7" screen.
Work: 16" screen.
Relax: 55" screen.
Sleep: 6.7" screen.

Congratulations. You've optimized your entire existence into rectangles of varying sizes.

The scariest part is that it feels completely normal.

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

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

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

Here's how it happens:

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

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

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

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

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

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

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

The phone disagreed.

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

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

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

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

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

But I've started asking a different question:

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

The answer is uncomfortable about 80% of the time.

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

Big difference.

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

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

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

Maybe it's time.

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

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You ship every deadline. Solve every outage. Work weekends debugging production.

Still no promotion. No visibility. No seat at the strategy table.

You assume you're not ready. Not senior enough. Not strategic enough.

Maybe you're not the problem.

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

Nothing moved.

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

She thought she wasn't ready.

Then she changed companies.

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

Same talent. Different soil.

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

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

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

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

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

Sometimes they would.

Often they won't.

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

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

Your talent stays constant.

Your environment is a choice.

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

Is it you?

Or is it your soil?

Sometimes the bravest move isn't working harder.

It's walking toward better ground.

♻️ Repost and comment if you've made this move

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Twenty minutes into the interview, he realized she knew more about distributed systems than he'd learned in fifteen years.

His first instinct wasn't excitement. It was panic.

"If I hire her, what's my value?"

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

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

I asked what he did next.

Long pause. Then a slight grin.

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

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

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

None of that happens if his ego runs the interview.

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

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

The ones who scale have killed that instinct.

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

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

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

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

That's growth trying to happen.

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

Your technical skills got you promoted.

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

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

Hire them before someone else does.

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

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