We start from an audit: how releases happen today, how long they take, what is manual, what is monitored, and what happens when something breaks. Most teams know the answers, but they are not written down anywhere — and that is precisely the problem.
Then we work in the order that pays back soonest: first a repeatable build and automated tests, then automated deployment with rollback, then monitoring and alerting, and only at the end containers or orchestration, if they are needed at all. That order is deliberate — Kubernetes before a working CI adds complexity rather than speed.
How risky a release is depends on the deployment strategy. Blue/green and staged rollouts let a change be withdrawn before it reaches every user. And all of the work happens in your accounts and your repositories — DevOps that comes with a dependency on a supplier is its own opposite.