Leadership
Your First 90 Days Set the Next Two Years
Aug 18, 2025
Four engineering leadership transitions taught me this: the first 90 days decide whether you’ll architect change—or spend the next year fighting organizational antibodies.
After my latest onboarding call, I closed my laptop, leaving a desktop full of logins, architectural diagrams that only hinted at reality, and a calendar crowded with stakeholders convinced that their priorities should be mine. This wasn’t new—I’ve done this three times before—but the challenge never changes: how do you diagnose organizational capability, build the right relationships, and deliver visible impact before the honeymoon ends?
Over two decades of scaling teams—from financial systems handling billions in transactions to global consumer platforms serving tens of millions—I’ve built a framework that works. It’s not just about learning the stack. It’s about understanding how change happens inside a system of people, priorities, and decisions.
Week 1: Organizational Archaeology
The first week isn’t about proving technical chops—it’s about listening and decoding how the organization actually works. Architecture diagrams matter, but so does the decision architecture.
In one transition, a “simple” authentication service turned out to span multiple teams and microservices. That wasn’t technical debt—it revealed how product decisions propagated through team boundaries without architectural governance.
My playbook:
Map where technical decisions actually happen
Watch for the cultural norms that shape velocity
Identify the informal influencers whose support will make or break change
Access requests and credential wrangling are table stakes. The real work is pattern recognition.
30 Days: Align Around What Matters
By the end of month one, you’ve seen enough to connect the dots. The biggest constraints rarely live in code—they stem from misaligned priorities, fuzzy ownership, or cultures that reward heroics over reliability.
This is the time to align stakeholders. Product wants speed. Ops wants stability. Security wants compliance. Your job is to architect solutions that serve multiple constituencies.
Early wins are typically those that improve engineering and deliver tangible business value. In one role, we significantly reduced fraud risk by embedding security into our delivery process—turning compliance from a bottleneck into a competitive advantage. That built lasting capability, not just a one-off win.
60 Days: Assess Capabilities, Demonstrate Strategic Thinking
Two months in, you’ve got enough context to assess both the technical and organizational landscape. This is where you separate tactical managers from strategic leaders.
I evaluate every initiative against three criteria: Does it reduce business risk? Does it compound engineering capability? Does it demonstrate strategic value to non-technical stakeholders?
Pick one initiative that proves all three. Improving CI/CD pipelines, for example, isn’t just “faster deployments.” Done right, it shows you can reduce business risk, boost productivity, and create learning loops that compound over time.
90 Days: Deliver One Visible Win
By month three, the expectation shifts. It’s no longer about how much you’ve learned—it’s about whether engineering is delivering business outcomes under your leadership.
My 90-day win was a complex system migration that proved engineering could de-risk major business transformations, not just support them. We became a strategic enabler, not a cost center.
Whatever your 90-day win, it should establish credibility, demonstrate strategic value, and build organizational trust.
The Executive Imperative
Three months in, your impact gets tested in one question: When the CEO or board asks your CTO about engineering leadership, what will they say?
Leaders who last aren’t measured by how many systems they learned or meetings they attended. They’re measured by whether they made engineering more capable of delivering business impact six months from now than it was on day one.
The question that separates engineering managers from engineering executives: Are you building systems that enable business strategy, or just maintaining systems that constrain it?
That’s the real performance metric—and the one that transforms careers.
