Why the two get lumped together
"Get this off my plate" usually gets answered the same way every time — hire someone, or buy a tool — without asking which kind of task it actually is. That's how businesses end up with an assistant doing rule-based busywork a system could handle, or a piece of software failing at a judgment call it was never suited for.
The two solve different problems. Delegating hands a task to a person who can use judgment, adapt to a one-off situation, and make a call you'd be comfortable with. Automating hands a task to a system that follows the same rule every time, with no judgment involved. Sorting your list by which of those two descriptions fits is the whole exercise.
A simple sorting test
For every recurring task on your plate, ask one question: could you write a one-page instruction sheet a new hire could follow correctly every time, with no judgment calls? If yes, it's a strong candidate to automate first — the rule is already clear enough to hand to a system.
If the honest answer is "it depends" — on the client, the situation, the exception that always seems to come up — that task needs a person who can weigh context, not a rule to follow. Those are the ones worth delegating to a human, whether that's an existing employee, a new hire, or an outside assistant.
Write the full list out first, then sort it into two columns. Most owners find the automate column is longer than they expected — a lot of what feels like it "needs a person" turns out to be repetitive once it's actually written down.
Order of operations
Automate first, delegate second. Handing a person a task that a system could do just recreates the same bottleneck one layer later — now a human has to remember the steps, and becomes a single point of failure if they're out sick or leave.
Once the automate column is actually handled, what's left in the delegate column is real judgment work — the kind that's worth paying a person for, because it's the kind a checklist can't fully cover. That's a better use of a hire than having them do the parts a system was always going to do more consistently.