First-Time CTO
You were a great developer yesterday. Today you're expected to be an executive.
My personal story
The Challenge Nobody Talks About
You were a great developer. Maybe a great tech lead or VP of Engineering. Then someone made you CTO.
Now you’re Googling at midnight wondering if you’re about to fail.
This is normal. Almost every first-time CTO goes through this. The role is different from anything you’ve done before, and nobody gave you a manual.
The painful realization that hits most new CTOs: technical skills aren’t enough. What got you here won’t get you there. The transition from individual contributor to executive is harder than anyone warned you.
What Changes When You Become CTO
As a developer or tech lead, you were rewarded for:
- Writing great code
- Solving hard technical problems
- Being the expert in the room
- Doing the work yourself
As a CTO, you’re rewarded for:
- Enabling others to do great work
- Making strategic decisions under uncertainty
- Communicating with non-technical stakeholders
- Building systems that scale without you
This isn’t a promotion - it’s a career change. You’re not a senior developer anymore. You’re an executive who happens to understand technology.
The First 90 Days
The first three months are critical. You’re seen as part of the solution, people will trust you and give you a free hand. Now is the time to make big changes. Big changes become much more difficult after that time, as people see you now as part of the problem.
Your first three months set the tone for everything that follows. Focus on:
Week 1-2: Listen Don’t make changes yet. Understand the current state. Talk to everyone - engineers, product, sales, the CEO. What’s working? What’s broken? What do people wish was different?
Week 3-4: Identify the real problems Separate symptoms from causes. “Deployments are slow” might really mean “we have no CI/CD” or “everyone’s afraid to ship” or “we have too much technical debt.” Find the root causes.
Week 5-8: Pick your battles You can’t fix everything at once. Choose 2-3 things that will have the biggest impact. Get buy-in from the team and leadership. Show progress. Do the hard things, the big changes.
Week 9-12: Build your operating rhythm Establish the meetings, check-ins, and processes you need to stay connected without micromanaging. Define how you’ll communicate with the CEO and board. Set expectations.
Common Mistakes First-Time CTOs Make
Staying in the code too long. You were great at coding. It feels safe. But every hour you spend coding is an hour you’re not spending on the strategic work only you can do.
Trying to be liked. Your job isn’t to be everyone’s friend. It’s to make good decisions, even unpopular ones. Respect beats popularity.
Not asking for help. You’ve never done this before. Neither had any other first-time CTO. The ones who succeed fastest are the ones who find mentors, coaches, or peer groups.
Ignoring the business side. You’re not just the head of engineering anymore. You’re an executive. You need to understand revenue, customers, market dynamics, board expectations.
Solving every problem yourself. Your job is to build a team that solves problems without you. If you’re the bottleneck, you’re doing it wrong.
You Don't Have to Figure This Out Alone
Most CTOs struggle in silence. They think asking for help is a sign of weakness.
It’s not. It’s a sign of wisdom.
The best CTOs I know have coaches, mentors, or peer groups. They have people they can talk to confidentially - people who’ve faced the same challenges and can help them navigate.
If you’re a first-time CTO feeling overwhelmed, that’s normal. You’re not failing. You’re just learning a new job that nobody taught you how to do.
Ready for Support?
I’ve coached 80+ CTOs through exactly this transition. If you want someone in your corner who’s been there - let’s talk.