One of the great promises of technology is automation. Take a slow, manual process, write some code, and suddenly it’s fast and efficient. But in practice, automating too early often has the opposite effect: it slows you down.
Why It Happens
Early processes are messy because the work itself is still evolving. You’re figuring out what customers want, how your team should work, what the edge cases are. At that stage, the “manual” way isn’t a bug — it’s a feature. It gives you flexibility.
When you automate too early, you lock in today’s mess. Worse, you wrap it in code that makes it harder to change. What used to take a few minutes of adjustment in a spreadsheet now requires a developer ticket and a deployment.
Examples Everywhere
You see this everywhere in startups.
A sales team automates their CRM before they’ve agreed on what a “qualified lead” is. Now the pipeline is fast, but wrong.
A finance team builds scripts to reconcile payments before deciding how refunds should be handled. Every edge case becomes a bug.
An ops team automates onboarding before realizing half of the steps aren’t needed. Now they’re stuck onboarding useless steps faster.
In each case, automation created the illusion of progress while quietly adding friction.
Why It’s Worse Now
In 2025, with AI tools everywhere, the temptation is even stronger. You can spin up a workflow in minutes. But speed doesn’t make the underlying process more stable. It just makes the mistakes scale faster.
The problem isn’t the tools. It’s timing. Automating chaos just gives you automated chaos.
When to Automate
The right time to automate is after the work feels boring. When a process is repeatable, predictable, and dull — that’s when automation shines. The boredom is the signal. If you’re still making changes every week, stick to manual.
The Lesson
Automation isn’t just about saving time. It’s about codifying decisions. Get the decisions wrong, and the automation becomes a tax you’ll pay for years.
The paradox is that waiting longer to automate usually makes you faster.