Every CTO we talk to asks us the same questions upfront. AWS or GCP? React or Vue? Do you know Kubernetes?
Every time we start a conversation with a new client, the first questions are almost always the same.
Do you work with AWS? Do you use React? Do you know Kubernetes?
Fair questions. Not the most important ones.
The most important questions — the ones that actually determine whether an engagement succeeds or quietly falls apart six months in — almost never get asked in the evaluation phase. They show up later, when it's expensive to find out the answers.
There's a well-known principle in software engineering: choose boring technology. The argument is simple — established technology has known failure modes. New technology comes with unknown unknowns nobody has hit yet.
But there's a less discussed corollary that matters more for how you evaluate a software partner.
If a team builds your core system on the wrong database, migrating out is a multi-month project. If they use the wrong deployment process — you change it next sprint.
This asymmetry changes what you should be evaluating. Technology choices are expensive to reverse. Practice choices are not. Which means the practices of the team you hire matter more than the stack they bring.
Technology is anything that needs to keep running to support your business — your codebase, your infrastructure, your data. Practices are how the team operates around that technology. They're invisible in a demo. They show up in production.
Three areas where practices determine the outcome of an engagement more than the stack does:
Most vendor evaluations spend 80% of the time on technology — stack, certifications, tooling. That's not wrong. But it's incomplete.
"How do you operate around the technology you build?"
Ask how they've handled a production incident on a previous engagement. Ask how they document architecture decisions and who has access to that documentation. Ask what a knowledge transfer looks like in practice, not on a slide.
The answers to those questions tell you whether you're talking to a vendor or a partner. Technology is table stakes. Practices are the differentiator.
