Hey!

Chris here. Welcome to Blueprint—the newsletter to help you build a winning engineering team.

I've been on both sides of technical disasters.

I've walked into companies drowning in complexity, and I've watched teams slowly slide toward chaos without realizing it until customers started screaming.

What always surprises me is how early the warning signs appear, long before the full-blown crisis hits.

But most leaders don't know what they're looking for.

Let me show you what to watch for. 👇️ 

📒 DEEP DIVE

The Hidden Signals of Technical Collapse

Here's what to watch for and how to fix it while there's still time.

When No One Can Solve the Problem

Here's the first and most obvious signal: problems start emerging that nobody on your team can solve.

Think about that for a second. You've got an entire team of trained professionals—people who supposedly know your system inside and out. Yet you have issues that everyone stares at like they're written in hieroglyphics.

This happens for 1 of 2 reasons:

1. You've over-engineered something to the point where it's become incomprehensible.

2. You've created such a spaghetti mess of complexity that nobody can untangle the knot.

Both situations are really bad—and point to the same underlying problem: Technical decisions have been made without considering whether the result is maintainable.

What's happening under the hood of your systems should never be a mystery to a team of well-trained individuals, let alone your team of well-trained individuals.

The Metric That Tells You Everything

There's one metric I watch more closely than almost any other when I'm assessing an engineering organization: How long does it take from the moment a customer submits a support ticket until it's fully resolved and live?

This single number tells you so much about the health of your engineering team. It shows you:

• Urgency – Does the team treat customer problems like emergencies, or do tickets sit in a queue for weeks?

• Quality – If you're drowning in new tickets every day, your product quality is terrible. Customers are essentially doing your testing for you, which is the worst possible scenario.

• Capability – If tickets are sitting open forever, it means your team can't solve the problems fast enough. Either they don't have the skills, they don't have the capacity, or the system is too complex for them to navigate.

When I see tickets living for a very long time without resolution, that's a massive red flag.

Something is fundamentally broken.

The Customer Becomes Your Tester

The most painful part of a technical collapse is that the customer always finds the problems first.

When your team doesn't catch them in development, and your QA process doesn't catch them, the issues make it all the way to production.

And now your paying customers are the ones discovering that things are broken.

This is a sign that poor decisions have been made (probably many of them) over a long period of time.

And you pay the price in customer trust and company reputation.

The Cave-Dwelling CTO Problem

Believe it or not, technical leaders actually make their biggest mistake after the collapse.

When a crisis hits, the instinct is to dive in and solve it yourself. You're probably capable of doing it. If you're a good CTO, you can absolutely go into a cave, emerge 3 days later, and have the problem fixed.

But nothing changes in your organization when you do that.

You've fixed that 1 problem. But you've created no problem solvers. So the next time a similar issue comes up, they'll be just as helpless as they were before.

This is probably the hardest lesson to learn during scale-up. You have to be willing to go slower on delivery so that you can train people up. You need more problem solvers throughout the company, not just one superhero who swoops in to save the day.

The speed of change is the speed at which you can take whatever problem has been thrown your way, put a team on a Zoom call, start working through it, and make them run the keyboard.

Yes, it's going to be slow. Painfully slow, even. But that's the pace you have to accept if you want to build a sustainable engineering organization.

What Actually Fixes This

Solving these issues isn't complicated, but it requires discipline.

It comes down to 3 steps:

1. Catch these signals early

   Pay attention to ticket resolution times, watch for problems that nobody can solve, and watch out for customers finding too many issues.

2. Resist the urge to be the hero

   Your job isn't to solve every problem; it's to create a team that can solve problems without you.

3. Build systems that prevent similar failures

   When something breaks, don't just fix it. Figure out how to make that specific issue impossible in the future.

This is why teaching what you know creates an engineering culture where quality matters, where problems get solved systematically, and where knowledge gets shared instead of hoarded.

BEFORE YOU GO…

The difference between companies that spiral into crisis and companies that stay healthy isn't luck.

It's that healthy companies have leaders who spot these signals promptly and actually do something about them.

They resist the hero complex, train their teams instead of solving every problem themselves, and build systems that prevent the same failures from happening twice.

If a technical crisis is in your future, the warning signs are already there. The question is whether you're paying attention.

Talk soon,

Chris.