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AI seems great at repetitive work. Where does it still struggle?

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19
Most AI discussions focus on what AI can do.

I'm more interested in where it still struggles.

From what I've seen, AI handles repetitive work pretty well:
  • extracting data
  • categorizing documents
  • matching transactions
  • summarizing information
But it seems to struggle once judgment or context becomes important.

For example, invoice matching is easy until there are partial deliveries, pricing differences, or missing references.

The same thing happens in reconciliation where straightforward matches are simple, but exceptions still need people.

I recently read about account reconciliation automation, and it reinforced that idea. The biggest value isn't replacing people. It's reducing how much repetitive work they have to do before making decisions.

Where have you found AI still falls short?
 
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8
I see the biggest problems at the boundary between execution and judgment.

AI can extract information, call an API or generate code fairly well when the rules are explicit. It struggles when the business rules exist only in someone’s head, the data is inconsistent, or nobody has clearly defined what a correct result looks like.

Long workflows are another problem. A small wrong assumption in the first step can affect every step that follows.

The approach that has worked better for me is to give the AI narrow tools, explicit constraints, logs and checkpoints. Irreversible actions should still require human approval. Generating code is often the easy part; understanding what must not change is harder.
 
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