Hey!

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

Ever find yourself completely buried in technical problems you're uniquely qualified to solve, with no time to breathe or build systems to escape?

 I'm coming out of exactly that storm right now.

The past eight weeks have been intense. I've pulled all-nighters, missed planning sessions because I was glued to my laptop, and found myself becoming the very bottleneck I help other companies eliminate.

Let me break down what happened and how I'm fixing it 👇

📒 DEEP DIVE

4 urgent all-nighters in 8 weeks. What happened?

How technical founders get trapped in short-term heroics at the expense of long-term scale.

4 all-nighters in 8 weeks. Constant fire-fighting. Critical implementations hanging by a thread. Clients waiting. Strategic planning sessions that I facilitated while simultaneously trying to fix urgent production issues.

 The last two months have been some of the most intense in my recent professional life. I stepped in as a fractional CTO at a company with rapid scaling needs and found myself pulled deeper and deeper into technical quicksand.

I've hit this wall before. Multiple times. And I always feel a little embarrassed when it happens again because I think, "This should be a problem I've solved by now."

But you never really solve it for new scale levels. The pattern looks similar, the feeling is the same, but the context is different. And the way you address it changes at different scales too.

 Here's what I was dealing with:

1. The company was scaling fast

2. They had critical technical gaps

3. Implementations with major clients were at risk of failing

4. The existing team couldn't handle the load

What makes this particularly challenging? I needed to invent solutions that didn't exist yet but also had to deploy them immediately. I needed deep focus time to create new systems, but I also had to train a team that didn't have the expertise to understand what I was building.

If you're a founder or technical leader, you've probably faced this exact scenario.

My first instinct was to do what I do best: dive in, invent solutions, and solve problems. I needed deep work time to create the systems they needed, and I had the expertise to do it faster than anyone else.

But that’s where I made a mistake.

Once I built these solutions, I became the owner of them. I solved immediate problems but created a bottleneck—me. 

Nobody understood the systems I'd built because I hadn't documented my work or trained others to maintain it.

What started as "let me help fix this real quick" turned into weeks of being pulled into every implementation issue. The organizational debt compounded by the day.

The Technical Hero Trap

There's definitely an addiction that comes with being the technical hero.

When you swoop in and solve problems others can't, you get an endorphin hit. That feeling when everyone's stuck, and you deliver a solution in hours that would have taken them weeks? 

It's powerful.

For technical founders especially, this creates a dangerous loop:

• You build something clever

• Everyone thinks you're amazing

• You take on more problems

• You have less time to document or train

• People need you more and more

• You become irreplaceable

• Your company gets stuck

I found myself in this exact spot—4 AM troubleshooting sessions, client emergencies only I could solve, and strategic work constantly pushed aside for tactical firefighting.

I've recognized this hero complex in myself for years. Left unchecked, it's toxic to organizational growth. 

I woke up the next morning and realized: I was part of the problem. I had to stop.

Fortunately, I also love teaching, which gives me another muscle to flex instead of always being the problem-solver.

Teaching the Teachers

 As your company grows, your role has to evolve in ways that aren't obvious at first.

In the beginning, you're doing the work. Then you graduate to teaching others to do the work. But there's another level most founders don't anticipate: teaching others to teach.

It's not enough to guide the technicians—eventually, you need to guide the guides.

This is a totally different skill. When you were guiding people in the thing you're super good at as a technician, that worked for a while. But at a new scale level, you'll find yourself needing to teach the teachers, which is a whole new level.

You're not just passing on technical knowledge anymore. You're showing people how to spot talent, how to break down complex topics, and how to transfer ownership gradually.

This transition is where many technical leaders get stuck. The role level is different. The approach is different. And if you keep applying the patterns that worked before, you'll keep hitting the same wall.

Breaking the Loop

 The turning point came during a strategic planning session I was supposed to be leading. Instead, I spent the first night glued to my laptop solving implementation problems that "couldn't wait."

I had to stop this cycle. It wasn't sustainable for me or the company.

Here's what I did to fix it and what you should do if you find yourself in a similar situation:

 1. Make shadowing mandatory

The single most important change: I banned solo work on critical systems.

If I'm building or fixing something important, someone else is watching my screen. Period.

This feels uncomfortable for many technical founders. Yes, I make more keyboard mistakes when people are watching. Yes, it feels awkward at first. But I've seen the results time and again—there's no substitute for watching someone solve problems in real time. 

But that discomfort is the point. Solo work creates knowledge silos that become organizational bottlenecks.

The process is simple:

• First session: My screen, my fingers on the keyboard

• Second session: Their screen, their fingers on the keyboard

• Follow-up sessions: They lead, I guide

This approach ensures they don't just learn what to do but how to think through problems. 

Those little decision moments—when you pause, consider options, and choose a direction—are where your expertise truly lives.

One team member told me after a session just last week: "There was no amount of explaining this you could have done ahead of time that would have made this sink in. I needed to watch you do it."

2. Create office hours

You can't be available to answer questions 24/7, but you need some structured time for your team to get unstuck.

I've added two blocks to my calendar—one in the morning and one in the afternoon—specifically for answering questions about systems I've built. Eventually, I'll take one of them away, then phase them out entirely as others gain expertise.

This creates predictability for both sides: the team knows when they can get help, and I can protect my focus time for other work.

It's like what college professors did—you set aside specific times when people know they can come to you with questions. For urgent customer-facing stuff that can't wait a week, having these daily touchpoints is crucial until you've fully handed off that expertise. 

3. Add proper management layers

One mistake I made was letting too many people directly demand my time. This flat structure created chaos because everyone thought their issue was the highest priority.

Adding appropriate management layers helps filter and prioritize issues properly. Not every technical question needs to reach the CTO or technical founder.

There were a lot of people bypassing a couple layers to get to me directly. I had to put a stop to this and make sure we had the right hierarchy in place.

Trust Is Everything

One thing that makes a massive difference when you hit these walls is the level of trust you have with your team.

When you have an employee you deeply trust, someone you've worked with for a long time and know is good—man, it's such a huge relief to hand off the stuff that's been weighing you down.

The key is to do a thorough session with them first—go through everything in detail, not just handing them a bunch of nonsense. Then, make yourself available to answer questions as they come up. You'll never get all the context out in one go, but they'll find the corners you forgot to mention three days later.

It's completely different when you're handing things off to someone unproven. You need tighter constraints, more check-ins, and clear deadlines. If they start missing dates or updates, things can go completely off the rails fast.

This is why companies build up extra value over time—you develop those relationships, you know who can solve what problems, and your organization becomes resilient through shared expertise. The longer you've been able to build relationships with your employees, the more effective you are as a company.

Looking back at people I've mentored this way, the results are incredible. One even became my business partner. I'm grateful every day that I invested that time—now he's honestly a better programmer than I am.

🎙 EPISODE OF THE WEEK

This week on "Build Your Business," Matt and I talk about how AI tools like Claude and Cursor are transforming small business workflows.

We show you exactly how these tools can write contracts, build sales SOPs, and brand your documents in minutes instead of hours.

The episode is packed with real-world strategies to help you scale—from building sales pipelines to email tracking to creating polished agreements—all while keeping your data secure.

 Listen wherever you listen to podcasts: Spotify | Apple Podcasts | YouTube

BEFORE YOU GO…

Technical expertise is a superpower. But like all superpowers, it comes with responsibility.

When you can solve problems others can't, it's tempting to keep swooping in to save the day. But sustainable growth means teaching others to fish rather than continuously feeding them.

The real measure of technical leadership isn't how many problems you can solve—it's how many problems your team can solve without you.

Next time you're tempted to be the hero, remember: your job isn't to be the smartest person in the room. It's to build more rooms full of smart people.

See you next time,

Chris.