AI and automation
Should we build something, and what shape should it be? Ordinary automation, AI assisting a person, bounded agents and the cases where the honest answer is to buy nothing — including what has to be true before any of it is worth starting.
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The useful distinction is not "AI or not AI". It is between fixed steps that need no judgement, work where a person should keep the judgement and use better tools, and a workflow repeatable enough for something to run it with a person holding the line. Those are three different builds with three different costs.
Most of these questions are settled by two answers: how repeatable the work is, and how much judgement it needs. Where the information is sensitive or a mistake is expensive, two more matter, and they change who should build it rather than whether it can be built.
The answer here is often "not yet, and not this". An undocumented process, work that comes round twice a year, or a system you already pay for that does most of it — each is a reason to stop before buying anything.
Worth settling before any of these
- Whether the work follows the same steps each time or is shaped case by case.
- How much judgement it needs, honestly — not how much you would like it to need.
- How often it comes round, because rare work rarely pays back the setup.
- What a mistake costs, and how sensitive the information involved is.
The questions in this family
Can AI help my team?
Often, but the useful question is where. AI that helps a person draft, summarise or analyse is a different decision from AI that runs a process.
Read the answerShould I automate this work?
If it is repeatable, frequent, low-judgement and written down, quite possibly. If any of those is missing, fix that first.
Read the answerShould I hire or automate this role?
It depends on what the work actually is. Repeatable, frequent, low-judgement work can often be automated; durable, growing, judgement-heavy work usually needs a person. Most real roles are a mix, and the honest answer is often to automate part of it first.
Read the answerDo I need an AI agent, or just better tools?
Usually better tools first. An agent runs a defined workflow inside boundaries; a tool helps a person do their own work faster. The diagnostic tells you which the evidence supports.
Read the answerIs my process ready to automate?
Four things have to be true: the steps repeat, they are written down, it happens often enough to pay back, and someone can say what a failure costs.
Read the answerWhat should I automate first?
The most frequent, most repeatable, best-understood, lowest-stakes thing you do. Not the most annoying one, and not the one with the best demo.
Read the answerShould I use AI or hire someone?
They answer different problems. AI reduces the effort in work that repeats; a person absorbs work that needs judgement, relationships and context.
Read the answerWhen is an AI agent the wrong answer?
When the process is undocumented, the work is rare, the judgement is high, the stakes are serious without a design to match, or a system you already pay for does most of it.
Read the answerCan AI handle customer enquiries?
Part of them, well, with a person holding the line. The split that matters is between enquiries with known answers and those needing judgement, empathy or authority.
Read the answerShould I automate reporting?
Usually yes, and usually after asking which reports anyone actually uses. Automating a report nobody reads makes it permanent.
Read the answer
Nearby decisions
These families overlap with this one often enough to be worth a look — most team decisions turn out to belong to more than one of them.