The First 90 Days: Step-by-Step DevOps Engineer Playbook

Everyone thinks the first 90 days are about showing off what you know. They’re wrong. The best engineers I’ve worked with spent their first month asking what everyone else considered “dumb questions.”

I was recently featured in The CTO Club’s playbook for DevOps engineers navigating their first 90 days. The advice I shared runs completely counter to what most people tell new engineers.

Here’s what I told them: breathe first, optimize later.

When you join a new team, there’s this intense pressure to demonstrate value immediately. To ship something impressive. To refactor that legacy code everyone complains about. But I’ve seen more engineers crash and burn trying to prove themselves than I’ve seen succeed by rushing.

The engineers who actually make an impact? They spend week one understanding why the “boring” system exists in the first place. They ask questions that seem obvious. They prioritize stability over speed, even when everyone’s screaming for faster deployments.

A boring system that works will always beat a flashy one that breaks. Always.

This philosophy comes from the same place as everything else I build—whether it’s the AI automation systems at Pabs Marketing or the rapid launch frameworks I’ve developed over the years. Sustainable systems beat impressive demos every single time.

If you’re stepping into a new DevOps role—or honestly, any technical leadership position—the pressure to perform immediately is real. But the engineers who last? They’re the ones who understand that asking “dumb questions” early is the smartest thing you can do.

Read the full playbook on The CTO Club to see the complete 90-day framework →