The Checklist
7 Questions Worth Asking First
March 10, 2026 · Erik Reagan
'I could automate this' and 'I should automate this' are two very different statements.
My highest-impact automations have zero AI in them. They're just well-structured workflows that move data, trigger actions, and free people from steps where their time could be better spent.
I've seen teams automate reporting workflows that nobody was reading — and onboarding steps for services they no longer offered. If it disappeared tomorrow, would anyone notice?
The real question isn't just "will this save time?" It's: what's the full cost of being manual — in time, errors, and inconsistency — versus the cost of building and maintaining it?
When you automate an immature process, you encode all of its gaps. If you find yourself saying "well, it depends" — the process isn't ready. Keep refining manually first.
The goal isn't to remove people entirely. It's to free them from mechanical parts so they can spend time where their judgment, creativity, and relationships actually matter.
Our biggest automation today has dozens of steps and branching logic. Version one was four steps — it just moved files to Google Drive. Every version along the way was useful.
The simpler the machinery, the easier it is to trust, maintain, and debug.
Without clear ownership, automations drift. The business changes but the automation doesn't. New edge cases emerge and nobody addresses them.
An API changes and data stops flowing — but nothing errors out. A field format shifts and the automation produces garbage. If it broke tonight, how long until you'd find out?
Retiring an automation that's no longer useful isn't failure. It's good housekeeping. Apply the same rigor to keeping automations as you do to building them.
Dive deeper into the full article at erikreagan.com