Your first conversation with AI: the complete guide for absolute beginners

I want to compare two AI tools on my real work. I'll give both
the same task and compare the outputs.

My profession: [profession]. A typical task I do every week:
[description of the task, e.g. answering customer questions].
Here's the specific assignment plus the source material:

[paste source material — an email, notes, a piece of text]

Do the work, then add three things:
1. Everything you had to guess because I didn't tell you.
2. Which parts of the output I should verify before using it,
   and exactly where.
3. One question whose answer would most improve the result.

No intro, no closing summary — start straight in on the work.

I want you to [describe the task, e.g. draft an email to a
client who's a month overdue on an invoice].

Don't write anything yet. First ask me 5 questions whose
answers would most change the result — the kind you'd
otherwise have to guess. Be specific, not generic ("what
tone" is a bad question; "should it sound conciliatory, or
already like a final warning" is a good one).

Once I answer, write the result, and below it list the
assumptions you still had to make on your own.

You're an experienced team lead. I manage [number] people in
[field], and on [day] I have a [length]-minute meeting.
Topic: [meeting topic].

Context that I know and you don't:
- what happened: [description of the situation]
- what I need to come out of the meeting: [decision / division
  of work]
- where I expect pushback, and roughly from whom: [description]

Prepare me:
1. An agenda broken down by minutes so it actually fits.
2. Three questions to open the meeting with that get others
   talking, not me.
3. Two objections that are likely to come up, and how to
   respond without putting anyone down.
4. A format for the notes: what I should walk away with
   written down.

No generic advice about leading people — just things tied to
this specific meeting.

I'm a student of [field], year [year]. I don't understand
[topic], and in [number] days I have [an exam / a test /
a paper] on it.

Explain it to me in three passes, back to back:
1. Simply, as if I'm hearing it for the first time — no
   jargon, 10 sentences max.
2. With an analogy to something from everyday life, and note
   where the analogy breaks down.
3. Through one concrete example, worked or walked through
   step by step.

Then give me 5 check questions, easiest to hardest, but don't
answer them yet — I'll answer, and you tell me where my
understanding is off. Ask about understanding, not
definitions.

I'm a freelance [profession]. A [type of client] client
reached out about [description of the job]. Here's what I know
from their inquiry:

[paste the inquiry text or call notes]

Write me a first draft of a proposal email:
- scope of work broken into phases, so it's clear what they get
- what's NOT included in the price, so it doesn't get assumed
  (no amounts — I'll add those myself)
- assumptions on the client's side: what they need to deliver
  and by when
- what happens if the scope expands mid-project
- one closing sentence prompting the next step

Tone: businesslike, confident, no apologizing and no
superlatives. Under 300 words. Then, separately, list 3 things
from the inquiry that are unclear and that I should nail down
before sending.

Take your previous answer and break it down. Return a table
with columns: claim | type (fact / opinion / estimate / filled
in from my request) | how confident you are | where I should
verify it.

Rules:
- list every number, date, name, law, and source reference as
  its own row
- where you estimated or guessed something, say so openly
  instead of justifying it after the fact
- at the end, list what you'd need from me so you wouldn't have
  to guess at all

Don't rewrite anything, and don't defend the answer.

I'm attaching a document called [name].

Summarize it in 10 bullet points. For EACH bullet, note which
part of the document it comes from — chapter, section, or page
number, plus the first few words of that passage, so I can find
it.

Where a claim draws on more than one spot, list all of them.
Where a bullet would be useful but the document doesn't support
it, DON'T write it — instead, add it to a "not found in the
document" list at the end.

Don't add anything from general knowledge, even if it happens
to be correct.

Explain your limits to me so that, as a beginner, I know when
to trust you and when not to. For each point, give an example
of a question where it actually comes up in practice.

Cover at least this:
- where your knowledge comes from and how current it is
- what happens when I ask about something you don't know
- how good you are at counting and at long tables of numbers
- what you remember from our earlier conversations and what you
  don't
- where you're most often wrong without me noticing
- what three kinds of tasks I should avoid giving you entirely

Be specific and skip the marketing — self-criticism is fine.

I'm a [profession], and I'm just starting with AI. My typical
week looks like this:

[describe 5-8 activities you repeat, and roughly how long each
takes]

Suggest a plan for my first 5 working days: one task per day
to try with AI. For each day, note:
- which of my activities it replaces or speeds up
- exactly what I should paste into the chat as source material
- how I'll know the output is good without having to send it to
  an expert for review
- how much time it can realistically save — be conservative,
  not optimistic

Order the tasks from lowest risk to biggest payoff. Don't
include anything where I'd have to paste in personal data or
non-public documents.

Help me write custom instructions I can set once so they apply
in every conversation.

About me: [profession, field, who you work for].
What I most often want from AI: [3-5 types of tasks].
What annoys me about answers: [e.g. long intros, jargon,
bullet points everywhere, hedge phrases].
How I want answers to sound: [tone].

Write me a draft, under 150 words, phrased as instructions to
you, not as a description of me. Add 3 sentences you'd
deliberately leave OUT, because they'd contradict each other or
constrain the model for no reason.