Is My Boss Too Risk-Averse About Automation?

The billing model matters too. Some providers resist automation because manual work creates more billable hours. If your clients are on fixed-fee or all-inclusive agreements, efficiency is usually beneficial: fewer preventable incidents, more proactive work, and better margins over time. Even with hourly billing, automation can free technicians to handle higher-value projects instead of repetitive maintenance.

I would avoid assuming bad motives immediately, though. Ask what evidence would make your boss comfortable: a test environment, limited permissions, a rollback plan, documented ownership, or a review period. If there is no acceptable path even for a tiny change, that tells you a lot about the culture.

Your boss has a legitimate concern about unmaintained automation, but he seems to be using that concern to reject automation altogether. A well-designed script should be tested, logged, reviewed, and maintained just like any other operational process. Manual procedures are not automatically safer—people skip steps, mistype values, and perform tasks differently.

The strongest argument for scripting laptop builds is consistency. Start with a small, reversible change rather than proposing a complete overhaul. Build in validation, clear error handling, logging, and a way to stop safely when a prerequisite is missing. Test it on a non-production device, document the results, and show exactly what happens when something fails.

There is some truth to the caution. A script with broad permissions can damage an environment much faster than a person working through a checklist, and vendor changes can break previously reliable commands. Scripts should be treated as software: use a test machine or development tenant, limit permissions, use version control, review changes, and deploy gradually.

That said, refusing to update a four-year-old script while also allowing security tooling to block it is not a strong risk-management strategy. The safer approach would be to investigate the block, update the script deliberately, and establish a maintenance and testing process.

This sounds less like a technical disagreement and more like an organization that has stopped learning. Automation does not eliminate responsibility; maintaining scripts becomes part of the job. Idempotent scripts, good logging, error checking, alerts, and staged rollouts make failures easier to detect and recover from.

A manual checklist can still be useful as a fallback or verification tool, but making every employee repeat every step by hand forever will limit how much the business can grow. If your boss will not allow even low-risk improvements after you demonstrate them carefully, you may eventually have to choose between staying stagnant and finding a workplace that supports the skills you want to develop.