There's an old joke about a guy searching for his keys under a streetlight. A cop asks where he lost them. "In the park," he says. "But the light is better here."
That's most automation projects. People start with whatever's most obvious — the templated report, the standard email, the weekly recap — because it's the clearest, most legible work.
Looking under the streetlight
We did a discovery call this week where a small business walked us through their entire workflow, including every recurring task, every weekly deliverable, every thing the team touches in a day. By the end, it was pretty clear which parts were draining them and which weren't.
Then we asked them to rank their priorities. Instead of ranking them, someone said: "well, these all have templates, so I imagine this would be the easiest to automate."
She wasn't wrong. They would be. But what's easiest to automate and what's most worth automating are two very different things.
In fact, the thing actually costing them the most time wasn't on that list at all. It was the process that didn't have a template: Pulling something from one system, reformatting it, checking it against something else, chasing down a missing piece, and moving the result somewhere new.
That kind of work feels too complicated to automate, so most people don't try.
It's okay to get a little messy
A year ago, automating a messy process meant building a rigid pipeline — if this, then that, with every branch mapped out in advance. The second anything deviated from the script, it broke. AI assistants handle this differently. Instead of a fixed pipeline, you give an assistant access to the tools involved — the inbox, the spreadsheet, the folder, the system of record — plus context about how your business works and what "done" looks like. Then it works through the steps. When something's missing, it can go find it. When something's ambiguous, it can ask.
Which means the multi-step, multi-tool, slightly-different-every-time work is finally something you can take on. And that’s what is most worth automating too.
It doesn't have to be all or nothing
People get hung up on whether something can be fully automated, when the real question is how much of it can come off your plate. If an assistant gets you 85% of the way through a process and you handle the last 15%, that's still a massive win.
Eighty-five percent of a task you do every week adds up fast.
Go to the park
The easy wins are worth doing because they build trust with your team and give you time back immediately. But they're rarely where the pain is.
Consider this a friendly reminder to look where you lost the keys, not where the light is good.
Stay curious,
Julia & Russell
