Hey!

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

If you're running an engineering team, you've probably seen this story: A brilliant engineer works hard and gets promoted to manager. Everyone's excited. Champagne's popped.

This is the obvious next step, right?

Fast forward three months.

Your star engineer is miserable. The team is struggling. And you're wondering how something so "obvious" went so wrong.

I used to think management was simple—just take smart people and train them. 

But after 20 years of building teams, I learned the hard way it's not this simple.

Want to know what actually works? Let me break it down 👇

📒 DEEP DIVE

Your Best Engineer Might Be Your Worst Manager

Why personality types matter more than technical skills for engineering managers.

Nobody is born a good manager. I've never met one in decades of building teams.

That "natural leader" you're thinking of? They learned it through training, reading, failing, and getting back up again.

Yet companies keep making the same mistake: They look at their engineers and try to spot who has that magical "management potential." 

But they're looking for something that doesn't exist.

What they should be doing is understanding the different types of engineers they have—and how to train each type to become effective managers.

The Obsessive's Paradox

First, let's talk about your obsessive engineers. You know the type—they're the ones who won't sleep until they understand why that bug exists or how to solve a problem. 

The ones who will take the entire system apart, get out the electron microscope if they have to, just to understand what's really going on.

These people are gold.

They have incredibly high agency. They don't just spot and flag problems—they own them. The problem migrates from the computer straight into their brain, and it's not leaving until it's solved.

But here's the catch: Obsessive, heads-down engineers rarely make good managers by default. 

Why? Because they're too in love with the problem-solving aspect of engineering to focus on the human aspect of management.

The Empathy Trap

What your obsessive lacks in empathy, your heads-up engineers make up for.

They’re the emotionally intelligent ones who can:

• Read a room

• Sense when a customer is struggling

• Navigate complex team dynamics

But they're not just good with people—they're protecting your obsessive types from the constant chaos. 

While your heads-down engineers are deep in problem-solving mode, your heads-up engineers are handling Slack storms, customer calls, and urgent emails. They know how to translate all that communication into tactical project work.

Conventional wisdom says these are your "natural" managers. But (surprise!) that's wrong too.

I've seen highly empathetic managers struggle with confrontation: tough feedback, necessary firing/re-org decisions, and standing firm in high-pressure situations.

Sometimes, too much empathy can be just as problematic as too little.

Building the Right Mix

Here's what I've learned about creating high-performing engineering teams:

You need both types of engineers.

Sure, once in a while, you'll find that unicorn who has both traits—technical obsession and high empathy. When you find these people, they're incredible but they're rare. Don't build your team structure expecting to find them.

You're better off building your team with this belief: You can't change people's core personality. What you can do is leverage their natural strengths.

For example, I once had an engineer who couldn't complete any project longer than 2-3 hours.

But the second a customer needed something? Boom—done instantly.

Instead of trying to "fix" this trait, we reorganized their work: They handled quick customer requests, and we gave the longer projects to others.

Training Managers Based on Their Type

Catering to natural strengths will help you build more effective engineering teams.

Your obsessive engineers will dig deep into technical problems, while heads-up engineers will maintain customer relationships and team harmony.

So how do you train these managers?

For technical obsessives:

→ Turn management into a technical challenge

→ Give them frameworks and metrics to optimize

→ Help them see team effectiveness as a system to improve

For empathetic types:

→ Build resilience through practice

→ Teach them that real empathy sometimes means having hard conversations

→ Give them tools for maintaining boundaries

The Pressure Test

We talked about this in the last newsletter, but pressure reveals everything.

Because that’s when the real traits emerge—who freezes, who steps up, who finds clarity in chaos. And that’s the key.

The best managers aren’t just picked based on personality traits. They’re shaped by experience, training, and how they respond when things get tough.

Some engineers thrive in the weeds, obsessed with fixing what’s broken. Others keep the team moving, reading the room, and handling the chaos.

Neither is naturally a manager—but both can be trained to lead in the right way.

Your job as a leader isn’t to force screwdrivers to be hammers. It’s to recognize what tools you have and build a system where each one serves its best purpose.

🎙 EPISODE OF THE WEEK

This week on "Build Your Business," we're killing the myth that core values are corporate BS.

Matt and I get real about why your values matter more than your hiring process—and why getting them wrong costs you every A-player you want to hire.

Want to know why some companies attract rockstars, while others can't hire their way out of a paper bag? We break it down step by step.

Check it out on YouTube.

BEFORE YOU GO…

We've all heard the saying, "People don't quit jobs, they quit managers." It applies to engineering too.

But too many companies treat management promotions like they're handing out merit badges—going to the most technically skilled, which almost guarantees team dysfunction.

Here's the truth: Your best engineers aren't naturally your best managers. 

But with the right training approach, both your obsessive problem-solvers and your empathetic team players can become great leaders.

Know your people, understand their strengths, and train them accordingly.

See you next time,

Chris