The fractured, but whole

"You weren't supposed to know until the end of the month."

That was the sentence that stuck with me. Not because it was directed at me.

It wasn't.

It was directed at a team member I've been mentoring for years. Let's call him Stan.

Stan had just heard he was being laid off.

Not from the company.

Not from his manager. I didn't even know.

Not from the founder making the decision.

He found out through his broker.

Think about that for a second.

Not...

"I'm sorry."

Just...

"You weren't supposed to know."

As if finding out was the mistake.

When I first started writing this article, it was going to be about frustration. About poor communication. About the lack of transparency.

About the chaos that follows when people who gave everything aren't treated with the dignity they deserve.

But somewhere between the first paragraph and this one, my article changed.

Because startups don't just break products.

They break routines.
They break plans.
Sometimes they break people.

And every now and then...

They fracture teams that never wanted to say goodbye.

The title is, admittedly, a terrible South Park reference. I couldn't resist.

A company can fracture.

A team doesn't necessarily have to.

Fractured

I've spent most of my career working with startups. You quickly learn that optimism and uncertainty always travel together.

Runway gets shorter. Funding rounds take longer than expected. Customers don't arrive as quickly as your financial model hoped.

For months, we knew the runway was shrinking. We also knew the founders were exploring every possible way to save the company. Investors. Acquisitions. Partnerships. Anything that could buy us another chapter.

So when the first layoff happened, it hurt. But it didn't bring us down.

Let's call him Kenny.

Kenny wasn't just another AI engineer. He was a personal friend of one of the founders. If anyone represented stability, it was him.

When Kenny disappeared almost overnight, I think everyone quietly reached the same conclusion without saying it out loud.

If Kenny wasn't safe, none of us were.

Still, we carried on. You tell yourself there's still a plan. You keep believing. You keep assuming the next customer, the next investor, or the next breakthrough is just around the corner.

Hope is an incredibly productive emotion.

Until suddenly it isn't.

I joined the company as a fractional CTO.

Officially, my responsibility was technical leadership.

Unofficially...

It became something much bigger.

Over the years, a small group of engineers became my team.

Stan was already there when I joined. He was an exceptional machine learning engineer. He could make models behave.

There was just one problem.

Scalability wasn't yet his playground.

The platform had a rather unfortunate habit of falling over when two users happened to execute heavy workloads simultaneously.

One web server.
Two machine learning jobs.
One very unhappy server.

It wasn't Stan's fault. Nobody had ever taught him how to think in distributed systems. How to separate compute from orchestration. How to design pipelines that could scale horizontally instead of vertically.

So we learned together.

The kind of learning where every production incident leaves a scar, and every scar becomes experience. I watched him grow from someone who could build impressive models into someone who could build systems around those models.

I watched him become a father.

Somewhere along the way, it stopped being obvious where professional growth ended, and life began.

I still remember one Monday morning. On Friday, we casually talked about a new AI-assisted approach to tackling complex engineering problems. By the time I logged in on Monday, Stan had already completed almost an entire feature with it.

I sat there for a moment, smiling. Not because the ticket was almost finished.

Because he hadn't needed me anymore.

I don't think I ever told him how proud that made me.

Then there was Kyle.

Kyle was different. I hired him myself.

A full-stack engineer. Kind. Thoughtful. The type of person who doesn't immediately speak during technical discussions, but when he finally does, everyone knows they can rely on him to finish the job.

Over time, something happened that no job description ever mentions. At some point, they stopped being "the ML engineer" and "the full-stack developer".

Stan became the person I'd text when something exciting happened. The first one I'd message in the morning. The person I'd send pictures of my kids to.

Kyle wasn't far behind.

Nobody tells you when colleagues become friends.

One day, you simply realise they already are.

I remember a conversation with one of the founders during one of our one-on-ones. He told me something that surprised me.

He said he envied the bond I had built with his technical team.

He wished he had that same connection. At first, I didn't really understand what he meant.

Looking back now...

I do.

Our stand-ups were never really stand-ups.

Yes, we discussed architecture. Deadlines. Production issues. But that was maybe half the meeting.

The other half was life.

How someone's holiday went. How another person's kids or dog were doing. The game that no one could stop talking about. The challenges in life that went well. Or the ones that didn't.

Those conversations were never on the agenda. Yet they were the reason everyone looked forward to them.

Without noticing, we had built something much rarer than a high-performing engineering team.

We had built trust.

The company itself had always been split across two worlds. One world built software. The other delivered custom services.

For two years, I kept asking for a product manager. The hire kept getting postponed. The consulting side paid the bills. The product became an afterthought.

We became exceptionally good at building something nobody was asking for.

I don't think it failed because we lacked talented people. We had plenty of those.

I think it failed because we never truly built a product company.

We built an outstanding engineering team around a product that never had someone relentlessly fighting for its direction.

Then came Stan's layoff.

Unlike Kenny's departure, I wasn't supposed to be surprised by this one.

Except...

I was.

Nobody had told me.

As the fractional CTO, I led the technical team. I was the one they looked to when things became uncertain.

Yet somehow, when one of my own team members was about to lose his job, I wasn't in the room.

One founder was on a three-week vacation and explicitly didn't want to be disturbed. The other lived on the other side of the world.

The decision had been made.
The message had been delivered.

Or rather...

It hadn't.

Stan found out through his broker without context.

When Stan called me with the news, he wasn't angry.

He was confused. He kept trying to make sense of the situation.

The company supposedly didn't have enough money to keep him after August.

That, painful as it was, I could understand. Startups run out of money. I've seen it before.

I called the founder. Not to argue the decision. If the runway was gone, the runway was gone.

I told him he had bypassed the person best placed to deliver the news, and that I needed to be that person, devastating as the conversation would have been. Especially when someone has spent years giving your company far more than their job description ever required.

The call didn't change anything. It couldn't. The message had already been delivered by a stranger.

But some things you say because staying silent would make you complicit.

What I couldn't understand was everything that happened afterwards.

The very same day, management introduced what was probably the most advanced technical opportunity the company had ever had.

An RFP asked for a similar platform but wanted it powered by a chatbot. Correlating knowledge of thousands of PDFs, existing datasets and access to machine learning pipelines.

Retrieval-Augmented Generation. Knowledge extraction. Chat interfaces. The kind of project data engineers secretly hope lands on their desk.

Stan's eyes should have lit up.

Instead, he had just been told he wouldn't be around to complete it.

Even stranger. The project wasn't being led by the engineering team. It was handed to a junior domain specialist who had just left school.

He proudly showed us his proof of concept.

A script.

Then he asked us how to turn it into a chatbot. How to make it scale. How to search eleven thousand PDF documents. How to make it interpret graphs or other images in the PDF.

None of those questions was unreasonable. We've all asked them. We've all started somewhere.

What hurt wasn't that he asked.

It was that the company believed the hard part had already been done.

To them, the prototype was the project.

To us, it was page one.

Stan understood that. Because he'd lived through that transformation himself. Years earlier, he was the person writing those first scripts. We spent years talking about data orchestration, RAG and chunking strategies.

Eventually, those conversations stopped feeling like mentoring.

They became debates between equals.

Which is why what happened next hurt him far more than losing the job.

The expectation suddenly became...

"Can you transfer everything you know to Kyle and the junior?"

Kyle...

the full-stack engineer. The person who already had to take over all of Kenny's responsibilities. Suddenly expected to become a back-end engineer, an ML engineer and a data engineer all at once.

Yet even then, he seemed more worried about Stan than himself.

The junior...

who had never deployed anything resembling this in production.

Years of experience.
Years of mistakes.
Years of learning.

Compressed into one month.

Knowledge doesn't work that way.

You don't transfer wisdom like copying files onto a USB stick.

I could see it in Stan's face.

This wasn't about ego. It wasn't even about the layoff anymore. It was something much more painful.

He felt...

Replaceable.

As though everything he'd spent years becoming had somehow been reduced to a few handover meetings.

They weren't replacing him.

They were replacing the idea of him.

The stand-up that followed is one I'll probably remember for the rest of my career.

I expected anger.
Questions.
Blame.
Silence.

Instead...

Stan thanked us.

He thanked us for teaching him. For challenging him. For helping him become the engineer he had become.

He talked about finally understanding cloud architecture. About learning why systems are designed the way they are, instead of merely how.

About leadership.
About engineering.
About growth.

Then he smiled.

He said that maybe, years from now, he'd look back on this as just another stepping stone. Then he hoped we'd all work together again someday.

I remember staring at my screen thinking...

"How are you comforting us?"

He had already zoomed out.

The rest of us were still trying to understand what had just happened.

As for me...

My mind was racing. I wanted answers. I wanted explanations.

Instead, all I could do was what leaders often end up doing.

Hide my own confusion.
Steady the room.
Offer a little bit of light while trying to find it myself.

I wasn't angry because they made a business decision.

I was angry because they took away my chance to do right by someone I'd spent years helping grow.

But Whole

Eventually, the call ended.

But the silence stayed with me.

Later that day, I realised I had been asking myself the wrong question. I kept asking...

"How could they handle it this way?"

The better question was...

"Why does this hurt so much?"

The answer had very little to do with startups, layoffs or products.

It had everything to do with people.

Because the best part was never the software.

It was watching people grow.

Because one day you notice they've been shaping you just as much as you've been shaping them.

The more I replayed the events in my head, the less angry I became. Not because I suddenly agreed with what had happened. But because every memory that mattered had nothing to do with the layoff.

When I think back on these past years, I don't want my strongest memory to be a badly handled layoff.

I want to remember Kenny.
Stan.
Kyle.

The near-impossible features. The tickets that became inside jokes years later. The code reviews that somehow turned into philosophy.

The engineer who once brought a server to its knees with two concurrent jobs and later became the person I trusted with systems processing thousands.

That's the story I want to carry with me.

Our industry loves beginnings. The first customer. The funding round. The impossible launch.

Nobody writes about the final stand-up.

The Slack workspace becoming quieter every week until one day it simply stops.

But endings reveal what mattered all along.

The repositories will eventually be archived.
The infrastructure will disappear.
The dashboards will stop refreshing.

But I now know what will remain.

Stan reminding us to zoom out on the hardest day of his professional life.

Kyle quietly trying to understand what came next while worrying more about everyone else than himself.

A founder admitting he envied the bond our team had built.

The realisation that software was never the thing we were really creating.

We thought we were building products.

Sometimes we were.

But the thing that lasted wasn't written in Python or TypeScript.

It was written in people.

Every engineer I mentored carried something forward.

What took me much longer to realise was that they left exactly the same gifts with me.

That's what survives.

That's what mentorship really is.

Not transferring knowledge.

Leaving fingerprints on one another.

The company may fracture.

The Slack workspace will fall silent.

We'll move to different companies.

Different products.

Different countries.

Different adventures.

But I'll carry a piece of Kenny.

A piece of Stan.

A piece of Kyle.

Just as I hope they carry a piece of me.

Maybe that's the real legacy of a startup.

Stan...

Maybe you weren't supposed to know.

But I'm grateful that I did.

Because it reminded me of what we had really built.

I know you think you leave carrying the lessons I taught you.

What you probably don't realise...

is how much of you I'll be carrying with me.

We are fractured.

Yet somehow...

We remain whole.