Founder of StrategyBreakdowns.com

TLDR: Worked in strategy consulting → Joined strategy team at Atlassian → Started writing strategy case studies → People liked them, so I left my job and went full-timeCheck it out → StrategyBreakdowns.comFor Partnerships Inquiries → passionfroot.me/strategybreakdowns

Tom Alder

This cheeky ad campaign is a masterclass in making people stop and laugh.

Airport billboards plastered with uncomfortably close faces and... features. 

Imagine touching down after 20hrs of international travel and seeing a 20ft nostril.

You'll probably chuckle, jump in an Uber, and remember that nose for weeks.

This is how you win the attention economy in 2026.

—

📌 P.S. I originally came across this campaign because it was going viral and came up on one of my ‘outlier trend’ dashboards. 

Lots of people asked me how I set this up, so I made a free tutorial teaching you exactly how I spot these trending topics / content / products in a few seconds (using free tools): https://lnkd.in/dnxsxJRm

In 2025 I went from $13k/mo to $24k/mo.

In 2026 I'm chasing $50k.

But honestly, my biggest wins were outside of work:

→ Packed up my cosy life in Australia
→ Donated/sold 90% of my physical possessions
→ One-way flight across the world

I've spent the last few months living in: Manhattan. Brooklyn. Barcelona. A tiny beach town called Torredembarra about an hour south of Barca. Valencia. Granada. Madrid. New York again. And now, East London.

2 years ago this was literally a dream I scribbled in a journal. 

Still feels totally surreal when I stop and think about it.

Thank you for reading this past year.

Let's win in 2026.

Anyone in London - hit me up!

—

👉 P.S. If you enjoyed this post, you'll love my newsletter - a 3-minute breakdown of the strategy playbooks and growth hacks behind the world’s greatest companies.

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The Xbox website in 2004.

Bring back the weird and wonderful web.

—

👉 P.S. If you enjoyed this post, you'll love my newsletter - a 3-minute breakdown of the strategy playbooks and growth hacks behind the world’s greatest companies.

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Summer 2009: Airbnb was stuck at $200 per week (!) in revenue… for 8 months straight.

Founders Brian Chesky and Joe Gebbia were running out of money and hope.

When they looked at their worst-performing listings, they all had something in common: "The photos sucked."

People were using flip phone cameras or blurry unedited photos. 

Properties were being undervalued because potential guests couldn't properly assess what they were getting.

The solution: doing something that seemed "unscalable".

The founders:

→ Flew from Mountain View to New York
→ Borrowed professional cameras  
→ Personally photographed 24 hosts' apartments

Result: Revenue doubled to $400 in one week.

This wasn't just about prettier pictures. It solved Airbnb's fundamental marketplace trust problem:

• Guests buying an experience they can't return
• From strangers they've never met
• With no way to verify quality beforehand

Professional photos provided instant credibility, visual proof, and increased perceived value.

The strategy didn’t stop there.

It sparked Airbnb's global Photography Program:
→ Network of 2,000+ freelance photographers
→ 35,000 listings shot across 5,000 cities
→ Listings with pro photos earn 2.5x more bookings

The lesson: Sometimes winning means stop coding and start knocking on doors.

—

💡 If you enjoyed this, it originally appeared in my free 3-minute newsletter, 'Strategy Breakdowns'.

Join 110,000+ strategy nerds from companies like Google, Meta, Atlassian, and Netflix: https://lnkd.in/g2FWfXGR

The value of $1,000 invested 10 years ago:

Amazon (AMZN) → $4,430
Netflix (NFLX) → $5,110
Apple (AAPL) → $8,170
Tesla (TSLA) → $33,630
AMD (AMD) → $123,010
Bitcoin (BTC) → $138,460
Nvidia (NVDA) → $157,870
XRP (Ripple) → $263,160
Dogecoin (DOGE) → $367,590
Ethereum (ETH) → $2,013,020

—

👉 P.S. If you enjoyed this post, you'll love my newsletter - a 3-minute breakdown of the strategy playbooks and growth hacks behind the world’s greatest companies.

Join 110,000+ strategy nerds from companies like Google, Meta, Atlassian, and Netflix: https://lnkd.in/g2FWfXGR

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Founder of Strategy Breakdowns

I'm hiring a writer!

But not just a "writer."

A Superwriter.

Here's how to know if that's you:
→ You're subscribed to like 20+ newsletters
→ You compulsively screenshot great emails, ads, charts etc
→ You can write about complex business concepts in a simple and engaging way
→ You use Claude/Perplexity/Deep Research/Zapier/Notion better than anyone you know

The job: Produce the best strategy case studies on the internet.

Start with 1-2 breakdowns per week.

As a Superwriter, a core part of your role *from Day 1* is building systems, templates, automations, and agents for research, curation, creation, editing, visuals etc.

Note: This role is *not* for you if you don’t know how to (or don’t want to) work with AI/automation to improve your output (more engaging writing, more thorough research, faster graphics, etc)

What you'll get:
- Front-row seat to a fast-growing internet media business
- Work directly with me - I'll teach you everything I know about writing, audience building, sponsorships, and anything else you're interested in
- Freedom to follow your curiosity and shape the role over time
- Access to pro versions of best-in-class tools (Claude, ChatGPT, Notion, Canva, Wispr Flow etc)
- Write + build things that reach hundreds of thousands (sometimes millions) of people in tech
- Fully remote, work from anywhere in the world

If this sounds like you: Job Description + Application in the comments 👇
If this sounds like someone you know: Tag them!

110,803 people read my weekly strategy essays, but I have 2 HUGE problems:

1. They aren't good enough
2. Not enough people read them

So...
✏️ I'm hiring a writer to produce the best strategy case studies on the internet!

→ I don't care about your CV.
→ I care about your screenshots folder.
+ the newsletters / YouTubers / books in your content diet.
+ how many hours you've spent using Deep Research / Claude Code / Nano Banana.

Important note: this isn't an ordinary 'Writer' role.
I'm looking for a 'Superwriter'.

You won't just write. You'll build systems.
AI research workflows. Notion Templates. Infographics. Charts. Surveys.

Exceptionally high quality bar + thinks in leverage.

This starts at 1-2 articles per week. Will grow into much more.
Fully remote. Work from anywhere.
Reach millions of tech founders + leaders each month.

If this sounds like you: Job Description + Application in the comments 👇
If this sounds like someone you know: Tag them!

Steve Jobs tried his best to acquire Dropbox, but couldn’t (and ended up launching a competitor instead).

In 2009, he made them an offer most startups dream about:

9-figure acquisition.
Plug into Apple’s ecosystem.
Direct access to Apple’s users.
Validation from a Silicon Valley icon.

But Dropbox’s founders declined. 

Jobs doubled down, saying it was "a feature, not a product."
He threatened that if they didn’t agree to an acquisition, Apple would “kill” Dropbox by launching their own storage product:
→ iCloud

But he was wrong.

iCloud was a huge success, but wasn’t enough to stop Dropbox’s historic run:

In just 7 months, Dropbox had accumulated 100,000 users.
Within 18 months, 500,000.
By October 2009, they'd crossed 2 million users.

A single mechanism was driving over one-third of all new signups:
→ Their iconic referral program 
(”Invite your friend to receive an extra 10gb of free storage”)

It was so effective that within 6 months, it was generating 2.8 million referral invitations monthly.
1 invitation sent every single second (!)

The trajectory from there went exponential:
→ 50 million users by 2011
→ 100 million users by 2012
→ 500 million users by 2016

In 2017, Dropbox hit a milestone faster than any other software company in the past: $1 billion in ARR.
The referral architecture powering Dropbox's growth combined behavioural psychology, network effects, and incentive design.
There’s something every builder can learn from what is arguably the most successful customer acquisition program in SaaS history, so I've deconstructed the 3x underlying principles into a free guide. 

🎁 Here’s the guide → https://lnkd.in/gc9-ih8J

Happy Monday. I got in a heated debate over the weekend. Help me settle this:

I've been daydreaming about redesigning the Strategy Breakdowns website for at least a year. 

Picture this:
→ An infinite canvas. Every article as a card in a grid. 
→ A new interactive way for readers to explore the archive. 

But it’s always sat in the embarrassingly long “maybe one day” pile.

Recently I came across a tool that let me prototype it in an evening.

It only took about 2 minutes of "aha" moments and "oh damn that's cool" design decisions for me to realise i had to turn my rainy-night-in into a breakdown.

The tool is called Alloy - it captures your existing product and lets you vibe on top of it

Most tools are fighting over hobbyists and side projects, so Alloy carved out its own niche: professional product teams prototyping on existing apps

Lots of clever product-led-growth mechanics and smart user psychology baked into this tool. 

✏️ Check out the full breakdown on your new favourite vibe-coding tool: https://lnkd.in/dudG8b6G  and here’s the interactive prototype I made: https://lnkd.in/dVy8zaX3

i can't stop thinking about how all software looks the same now

in the early 2000s, winamp let users completely redesign the interface

→ alien heads
→ video game themes
→ animated creations

it sparked one of the internet's first user-generated design communities

there's actually a museum preserving 100,000+ skins from that era (link below)

somewhere along the way, we lost something special:
→ the ability to add personality into the tools we use every day

my secret wish is that AI brings back the 'customisation layer'

software that feels yours

—

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Join 110,000+ strategy nerds from companies like Google, Meta, Atlassian, and Netflix: https://lnkd.in/g2FWfXGR

Software looks the same 

40 years of enterprise software in one chart:

Ownership → subscription → consumption → autonomous 

We're entering an unrecognisable era.
The winners of the next decade will be defined by AI GTM, outcome-based pricing, and the merging of software and services.

We hear a lot about the ‘one-person unicorn’.
A single operator building a billion-dollar company with new business models unlocked by AI.

Im curious - what do you think that business actually *looks* like?
Whats the product? How is it marketed? How does the company operate?

Something I’ve been wondering a lot about lately. Keen to hear your thoughts 💭

—

👉 P.S. If you enjoyed this post, you'll love my newsletter - a 3-minute breakdown of the strategy playbooks and growth hacks behind the world’s greatest companies.

Join 110,000+ strategy nerds from companies like Google, Meta, Atlassian, and Netflix: https://lnkd.in/g2FWfXGR

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

Strategic IT Leadership for Growing Companies

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

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

Systems that don’t talk to each other

Vendors that overpromise and underdeliver

Teams that pull in different directions

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

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

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

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

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

I’m here to help you:

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

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

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

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

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

No bloat. No buzzwords. No bureaucratic nonsense.

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

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

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

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

Who I Work Best With
Founders and business leaders who:

Are serious about scaling

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

Value momentum over perfection

Want a partner who talks business, not just tech

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

Phillip R. Kennedy

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

I thought I was helping.

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

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

Then I noticed something.

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

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

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

That landed like a punch.

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

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

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

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

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

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

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

But here's what changed when I did:

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

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

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

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

I build less now. We ship more.

Trust scales better than talent.

I wish someone had told me that three years earlier.

♻️ Repost and comment if you've made this shift

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

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

I asked him about his best manager.

Strong candidate. Decade of experience. We were halfway through the interview.

He paused. Then he told me about a VP of Engineering from eight years ago.

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

He told me about a 3 AM incident.

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

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

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

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

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

She wasn't having it.

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

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

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

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

He still tells that story.

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

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

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

The metrics fade. The moments stay.

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

The difference was never the dashboards.

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

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

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

He'll remember it forever.

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

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

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

The candidate took the job.

He's still there. Four years later.

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

Be the leader they mention at their next three companies.

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

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

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

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

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

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

He never named the engineer.

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

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

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

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

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

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

If everything goes wrong, they take the blame.

Sound exhausting? It is. Sound thankless? Often.

So why do it?

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

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

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

Here's what I've learned:

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

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

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

It's a harder transition than any technology migration.

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

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

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

Leadership is a practice, not a position.

It's a choice you make every day.

Make it today.

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

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

A recruiter asked if I knew any AI experts.

"How do you define AI expert?" I asked.

"Someone who's used ChatGPT for six months."

That's not an expert. That's a customer.

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

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

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

Here's the spectrum nobody wants to acknowledge:

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

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

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

Most people are users cosplaying as practitioners.

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

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

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

What actually counts:

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

Specific. Measurable. Actually built.

The hype will settle. It always does.

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

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

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

The hype fades. The work stays.

Make sure you have some.

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

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

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

Nobody called it a failure because it shipped.

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

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

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

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

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

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

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

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

It didn't.

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

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

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

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

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

Shipping isn't success. Mattering is.

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

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

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

"This is high priority."

I watched a VP send this message to five engineers.

What they heard:

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

Same message. Five interpretations. One very confused sprint.

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

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

Here's what happens:

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

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

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

Both outcomes are your fault.

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

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

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

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

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

The fix is almost embarrassingly simple:

Replace "ASAP" with an actual time.

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

Specific beats urgent every time.

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

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

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

Clarity is kindness. Vagueness creates anxiety you never see.

Your team isn't ignoring your priorities.

They just can't read your mind.

Stop making them guess.

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

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

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

They're not hiding it.

They just stopped telling you.

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

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

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

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

The VP never heard it. Not really.

Here's what happened:

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

Engineer heard: "This isn't important."

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

One conversation. Two completely different memories.

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

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

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

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

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

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

They're not hiding information.

They've learned you're not really asking.

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

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

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

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

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

Then wait. Ten seconds of silence feels like forever.

That's where the truth lives.

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

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

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

Neither of them is you.

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

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

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

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

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

So where does differentiation happen?

Before the application.

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

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

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

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

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

Starting is simpler than you think.

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

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

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

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

Build the thing they can't automate.

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

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

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

Just a slow Tuesday that turns into a slow decade.

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

Beautiful systems.

Then I asked about his career plan.

Long pause. Slight panic.

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

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

He laughed. Then stopped laughing.

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

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

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

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

You build alerting for services. Not for yourself.

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

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

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

It is insane. It's also normal.

What changes when you apply systems thinking to yourself:

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

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

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

Takes an hour every three months.

You build systems because drift is the default.

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

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

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

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

Three months later he called.

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

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

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

They assumed that was just how things worked.

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

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

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

"What about actual engineering leadership?" I asked.

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

"That was the engineering leadership."

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

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

Zero air cover.

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

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

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

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

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

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

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

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

That's the job.

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

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

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

Some things are worth more than titles.

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

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

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

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

Maybe you're not the problem.

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

Nothing moved.

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

She thought she wasn't ready.

Then she changed companies.

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

Same talent. Different soil.

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

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

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

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

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

Sometimes they would.

Often they won't.

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

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

Your talent stays constant.

Your environment is a choice.

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

Is it you?

Or is it your soil?

Sometimes the bravest move isn't working harder.

It's walking toward better ground.

♻️ Repost and comment if you've made this move

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I have been seeing this take going around lately:

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

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

The scariest part is that it feels completely normal.

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

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

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

Here's how it happens:

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

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

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

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

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

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

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

The phone disagreed.

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

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

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

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

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

But I've started asking a different question:

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

The answer is uncomfortable about 80% of the time.

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

Big difference.

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

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

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

Maybe it's time.

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

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Most tech leaders will finish this year where they started.

Same title. Same scope. Same invisibility.

Not for lack of talent. For lack of intention.

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

It doesn't.

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

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


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

Not networking. Conversation.

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

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

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


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

Not polished. Not strategic. Just captured.

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

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

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


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

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

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

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

Your team trusts you more because you stopped pretending.


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

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

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

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


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

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

Block it. Protect it like uptime.

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

Small numbers. Massive compound effect.

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

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

The ones who act will wonder why they waited.

Start this week.

♻️ Repost and comment if you're starting today 

➕ Follow me (Phillip R. Kennedy) for more on careers that compound

Founder

Vice President of Information & Technology

Pandora Jewelry

Co-Founder / Chief Technologist

Systems Consultant

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

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

If you struggled, so will your team.

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

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

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

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

That shift should concern every technical leader.

Here's why:

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

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

This isn't just Amazon.

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

The era of being valued for potential is ending.

Now you're valued for evidence.

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

Unless their leader helps them.

Here's what this means for you:

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

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

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

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

The Amazon article quotes their new guideline:

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

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

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

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

Make sure your team has a good answer.

Not because the game changed.

Because you taught them how to play it.

♻️ Repost and comment if your team needs to hear this

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"Psychological safety" was printed on the office wall.

Then production went down at 3 AM.

The VP's first question wasn't "What broke?"

It was "Who was on call and why didn't they escalate faster?"

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

Blameless culture. Growth mindset. Learning from failure.

Beautiful words. Framed and mounted.

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

That's when the real culture showed up.

Not the documented one. The actual one.

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

Your engineering culture doesn't live in your handbook.

It lives in seven moments:

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

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

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

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

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

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


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

Long pause.

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

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

Longer pause.

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

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

That's when values become real or become decoration.

Your team already knows which one yours are.

They're not reading your Confluence pages.

They're watching what happens after things break.

And they're taking notes.

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

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

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

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

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

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

I asked what he did next.

Long pause. Then a slight grin.

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

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

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

None of that happens if his ego runs the interview.

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

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

The ones who scale have killed that instinct.

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

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

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

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

That's growth trying to happen.

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

Your technical skills got you promoted.

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

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

Hire them before someone else does.

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

➕ Follow me (Phillip R. Kennedy) for more on building teams that scale past your ceiling

Twelve people in a conference room. Six months into a CRM migration everyone knew was drowning.

$40K a month in burn. Zero business value shipped. And there we sat, discussing "revised timelines" and "adjusted scope."

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

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

So I stopped trying to say stop.

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

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

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

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

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

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

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

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

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

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You're excellent at saving failing projects.

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

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

Backend rewrite stalled? Call him.

Migration falling apart? Call him.

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

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

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

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

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

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

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

And he admitted he let them.

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

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

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

Same person. Different expectations.

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

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

♻️ Repost and comment if you've ever been "too valuable" to promote

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"Do you actually want us to ship this? Or are we just building prototypes for your ideas?"

The room went quiet.

A senior engineer had finally said what everyone had been thinking. The VP sat there, mouth open, reaching for words that wouldn't come.

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

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

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

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

"We should really be thinking about..."

"Have you seen what the competitor launched?"

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

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

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

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

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

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

The engineer's question broke something open.

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

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

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

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

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

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

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

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

Your team already knows.

♻️ Repost and comment if you've built prototypes for someone else's ideas

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