Hey!

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

When I go into companies as interim CTO, one of the first things I look at is developer experience. And almost every time, I see the same pattern: New developers join, and 7 months later, they're finally starting to deliver value.

7 months. Think about that for a second.

That's not just lost time—it's burning money, talent, and opportunity. And the worst part is, most companies don't even realize they're doing it wrong.

Let me show you what I've learned about fixing this.

📒 DEEP DIVE

Developer Onboarding is Your Most Expensive Product Failure

Why treating new developers like customers changes everything.

Every time a developer walks into a new codebase, it's like being dropped into a foreign city at midnight with no map. This happens for most developers a few times in their career. In my work, I see it multiple times a week.

So I've learned we can prevent this disorientation by treating onboarding as a product.

Yes, I said product. Because that's exactly what your onboarding is—a product. And your developers? They're your customers.

The Empathy Gap

When you've been deep in a system for years, it's easy to forget how much context lives in your head. The acronyms, the business logic, the "obvious" workflows—none of this is obvious to someone walking in fresh.

The curse of knowledge applies to engineers as much as any other career.

Engineering leaders look at struggling new hires and think, "Why don't they just get it?" But when a new developer is struggling, it's rarely about capability or motivation. Most new hires come in hungry to prove themselves.

They just need a clear path forward.

So how do I approach this when I take over engineering leadership? I look at how we can make onboarding impossible for a new developer to fail.

Not just easier—impossible.

Think about it like you're designing a critical user flow in your product. Would you launch a feature where one wrong click could break the entire system? Of course not.

So why is your onboarding full of these exact failure points?

I've seen developers waste 50+ hours just trying to get their development environment set up. That's more than a week of work lost to poor design. And it's completely unnecessary.

The Career Investment

There's another angle here that most companies miss completely: career trajectory. Especially right now with AI changing everything, engineers are hyper-aware of their career paths.

I've seen too many companies lose great engineers because they hoarded the interesting work. Usually, it's technical founders keeping all the cutting-edge projects for themselves while their team handles maintenance.

How does this show engineers you're invested in their growth? If you won't give them opportunities to work with new technology, someone else will.

The Action Plan

When I say treat onboarding like a product, I mean it literally. Start with your customer—the new developer—and work backward. Here’s what that looks like:

1. What do they need to know? Not just the code, but the context. The business logic. The "why" behind architectural decisions.

2. How can you make the setup foolproof? Every step needs to be automated or documented so clearly that it's impossible to get wrong.

3. Where can they grow? Map out clear paths for skill development and career progression.

This takes time and a lot of it. But you're already paying this cost, but in the form of wasted engineering hours, delayed projects, and lost talent. It's on you to shift that cost into an investment.

Keep Them or Lose Them

When you nail onboarding, retention goes up. Makes sense, right? People stay where they feel successful and see a future for themselves.

It's simple: 

→ Pay people well*

→ Set them up for success

→ Give them interesting work

→ Make it clear how they can grow

[*above market—trying to save on engineering talent is the definition of penny-wise, pound-foolish]

But none of this matters if your onboarding is broken. Because people won't stick around long enough to see the opportunities if their first experience is chaos.

🎙 EPISODE OF THE WEEK

This week on Build Your Business, Matt and I tackle the one resource everyone has: time.

We break down why most people waste time trying to do everything instead of focusing on what matters. We dive into how to balance work and family, and why freedom comes from focusing on what you do best.

Perfect timing if you're feeling overwhelmed with tasks someone else should be handling. We cover exactly how to identify what only you can do, and what you need to delegate.

Listen wherever you listen to podcasts:

Spotify

Apple Podcasts

Youtube

BEFORE YOU GO…

Every time I see a company struggling with developer onboarding, I think about this: Your most expensive software isn't the tech you're building—it's the process you use to build it.

Fix your onboarding, and you fix your entire engineering organization.

Keep it broken, and nothing else you do will matter.

Your job isn't just to hire great engineers—it's to give them a reason to stay.

Until next time,

Chris