Hey!

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

I've been a fractional CTO more times than I can count—it’s what I do for a living. And that experience has taught me that your first 100 days as CTO is the most critical period you'll face.

The sequence of your decisions during the first 3 months will make or break both your success and the company's trajectory.

Today, I'm breaking down exactly what those 100 days should look like.

(If you’re a CTO, you might want to bookmark this one.)

📒 DEEP DIVE

The 100-Day Roadmap Every New CTO Needs

The proven sequence for your critical first 3 months in the CTO role.

I've broken down the first 100 days into 3 distinct phases:

Days 1-30: Deep Understanding—Learn the business and technology before making any changes

Days 31-65: Focus on Talent—Figure out who can help take the organization to the next level

Days 66-100: Build the Roadmap—Create a clear vision for the future

This sequence isn't arbitrary. Each phase builds on the previous one, and skipping steps will set you up for failure. 

Let's dive into each phase:

Days 1-30: Deep Understanding

Day one, the first thing you have to do is understand the entire ecosystem. This is hard to do—you can't get it done in a day—but I've seen a lot of CTOs flame out because they went in and started changing things without understanding the business.

This first phase takes about 30 days, and most of what you're doing is talking to people:

• Talk to employees

• Talk to programmers

• Talk to project managers

• Talk to customers—a lot

Customers will tell you more than you probably wanted to hear about what's good about the product, what's bad about the product, what's good about the service, what's bad about the service. You need to get in and really understand it.

During this time, you also need some quiet time looking over things:

• Looking at code

• Checking your position in terms of automated tests

• Examining what your infrastructure looks like

• Evaluating how mature the organization is technologically compared to where you should be given how long you've been around as a product

This is a time for observation. 

Don't put on your headphones and sit in silence, trying to figure out how a system works. You need to watch people doing their jobs. Watching someone solve a problem who's picked up expertise in a space is a completely different experience than hearing them talk about it.

You can't skip this phase. Every instinct will tell you to start "fixing things" immediately. Don't.

Days 31-65: Focus on Talent

Once you understand the landscape, the next thing you need to do is really start digging into the talent and the organization.

You need to figure out who your leaders are going to be:

• Who has leadership potential?

• Who has super high-tech skills?

• Who are the people you're going to lean on to get stuff done?

This happens with a lot of interaction. You're going to talk to people to find out:

• Who does this person trust?

• What are the informal networks?

If I'm looking at the org chart and then I go ask people, "Who do you go to?" and it's not their manager over and over, you might want to flag that.

Digging in on the talent side will take a long time. This process is going to eat up basically all the way to maybe the last bit of that first hundred days.

And throughout this process, you will probably need to make some changes from an HR standpoint because you're going to need to get rid of some people and bring some new people in.

This is just part of what happens. You cannot execute the best plan on the planet with the wrong people. The people have to be right. The people are the foundation.

Days 66-100: Build the Roadmap

As you approach the final stretch of your first 100 days, it's time to focus on creating a clear roadmap for the future.

Throughout your first few months, you've likely been communicating short-term plans—people need to understand what you're focusing on in your early days. 

But now, your attention shifts to the bigger picture: what does your technology roadmap look like for the next year?

This roadmap serves several critical purposes:

• It unifies the vision for the entire organization

• It provides clear marching orders for your teams

• It equips managers with the "why" behind decisions when talking to their teams

• It answers the fundamental question: "What will our product look like a year from today?"

The roadmap lays out how the whole machine works together to deliver business value to your customers. It should connect your technical decisions to customer needs and business outcomes.

By now, you've built the foundation necessary to make this roadmap meaningful:

✅ You understand the business, the technology, and the customers

✅ You've identified and started developing the right talent

✅ You're positioned to create a realistic path forward

🎙 EPISODE OF THE WEEK

This week on "Build Your Business," Matt and I tackle a question every founder eventually faces: How do you know when it's time to pivot—and how do you do it without burning everything to the ground?

We break down real-world pivoting strategies from our own experiences—including how Matt shifted from local gyms to global online coaching, and how I spotted a massive opportunity in the insurance tech space.

If you're facing slow sales, customer churn, or trying to navigate big market shifts like AI, this episode will give you both the mindset and tactical approach to pivot smart—not desperate.

Check it out: Spotify | Apple Podcasts | YouTube

BEFORE YOU GO…

This three-part sequence is essential. 

If you rush to create a roadmap before understanding the ecosystem and getting the right people in place, you're building on sand. 

I've seen technical leaders approach their new CTO role in countless ways. Those who try to prove themselves immediately by making sweeping changes almost always struggle. Those who follow this approach tend to succeed.

It's counterintuitive, but your value as a new CTO isn't measured by how much you personally fix in those first months. It's measured by how well you set up the organization to solve problems without you.

The pressure to show results immediately will be intense. Resist it. The best CTOs play the long game.

Get the right people first, then execute your initial plan, and only then can you effectively build for the future.

Talk soon,

Chris.