When stepping into a new leadership role — especially as a CTO — you might feel the urge to make an immediate impact. You want to fix things, clean up the roadmap, ship fast, and prove your value.
But here’s the truth: technical change means nothing if you haven’t built trust first.
The first 90 days of any CTO engagement, whether full-time, interim or fractional, aren’t about heroics. They’re about humility, observation, and earning the right to lead.
Because you’re not just joining a team. You’re stepping into a system of habits, histories, dynamics, and emotions. And until you understand that system, you can’t shift it.
Day One: Don’t Start with Code — Start with People
Your instinct might be to dive into the architecture, audit the backlog, or review how sprints are run. But the most important thing to do in week one?
Listen.
Run 1:1s with your engineers, product managers, founders, analysts, and anyone who touches the tech stack. Ask simple questions like:
- What’s working?
- What’s frustrating?
- What’s slowing us down?
- What’s the one thing you’d change if you could?
These conversations are gold. They reveal not only technical bottlenecks but also emotional temperature — how safe your team feels, how empowered they are, and how connected they feel to the broader business goals.
More importantly, it shows them that you’re not here to “fix” them — you’re here to understand them.
The Soft Power of Observation
Trust isn’t built by coming in hot with opinions. It’s built by watching patiently, asking good questions, and sharing insight only when it adds value.
In those early weeks, you’re observing how work flows, how communication happens, how decisions are made (or avoided), and what dynamics exist between tech and the rest of the business.
đź“Ť Who holds influence?
đź“Ť Who’s quietly leading?
đź“Ť Where does communication break down?
đź“Ť Where are expectations misaligned?
This isn’t political — it’s practical. Because as a CTO, your role is to build systems and relationships. And you can’t do either well unless you understand the lay of the land.
Set Expectations — Clearly and Calmly
One of the fastest ways to build trust as a CTO is to remove uncertainty. Engineers don’t need you to be a superhero. They need clarity.
đź’¬ What do you expect from the team?
đź’¬ How do you prefer to communicate?
💬 What’s your philosophy on code reviews, delivery cadence, documentation?
💬 How will you measure success — and how will they know if they’re doing well?
Don’t over-engineer the answers. Just be consistent and transparent. When teams know what good looks like — and that the goalposts won’t keep moving — performance naturally follows.
Look for Small Wins That Unlock Bigger Ones
Trust deepens when your actions match your words.
That’s why I always look for small, unglamorous wins in the first few weeks. Things that may not be revolutionary, but show the team you’re here to help.
Maybe that’s unblocking an old JIRA ticket that no one wants to touch. Maybe it’s simplifying the way devs deploy to staging. Maybe it’s just getting a proper retrospective on the calendar again.
These wins show you care about their world — not just your own roadmap.
Show Them You’re in the Work With Them
There’s a big difference between leading from a whiteboard and leading from the ground. You don’t have to write code full-time to build credibility — but you do need to be present in the work.
âś… Join standups without taking them over
âś… Sit in on QA and design conversations
âś… Ask questions in code reviews
âś… Be curious, not commanding
When the team sees that you’re invested, not distant, they’ll meet you halfway. That’s where real trust begins.
Handle the Skeletons with Empathy
Every tech org has its skeletons — the half-built migration, the undocumented legacy system, the “quick fix” that became permanent. When you discover them, don’t judge. Don’t shame.
Acknowledge the context. Respect the decisions made before you got there. Then offer a path forward.
Because nothing breaks trust faster than a leader who starts by criticising what they don’t understand.
Founders and Stakeholders: Earn Trust Sideways Too
It’s not just about the engineering team. As a CTO, you sit at the intersection of product, finance, ops, sales and compliance — especially in freight, supply chain or ESG, where platforms often touch every part of the business.
Spend time with those stakeholders. Ask what’s been promised. What’s been delivered. Where tech has helped — and where it’s disappointed.
Show them you’re not just here to build cool things — you’re here to solve business problems.
Final Thoughts
The first 90 days as a CTO aren’t about you. They’re about the team.
It’s about listening, learning, and showing — through your words and your actions — that you’re not here to be the smartest person in the room.
You’re here to build a room full of smart people who trust each other to do great work.
Whether you’re leading full-time, part-time, or as a fractional CTO, the playbook is the same:
Lead with empathy. Deliver with consistency. Leave ego at the door.
The code can come later.
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