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Asking well: cheatsheet

A prompt is not a question. It is a task, instructions, and context. The machine is still predicting, and your words are what it predicts from.

If you remember one thing: context is the part almost everyone skips and the part that helps most. Starve the machine and it predicts the most average document on the internet; feed it and it predicts something shaped like you.

PartIt coversCover letter example
Task”what you want the AI to do”Draft a cover letter for the job posting below
Instructions”how you want the AI to do it”Under three hundred words, warm but direct, no stock phrases, two versions
Context”what you want the AI to know”Who you are, your proudest wins, the posting pasted between triple quote marks
HabitWhy
Start simple, then build through conversationYou refine faster than you can pre-plan
Be specificVague guidance buys the most average answer
Say what to do, not what to avoidNaming the forbidden thing puts those words into play
Ask for many options, not oneVariability is fuel; pick from a menu
Fence off pasted materialTriple quote marks keep the posting separate from the request
Start fresh when a thread turns to sludgeThe whole conversation is input; ask it to summarize the useful parts as a single prompt and carry that into a clean thread
Ask the machine to draft your promptWhen writing the prompt feels hard, describe the goal instead
LineMeaning
One answer is a sample, not a verdictIn most chat tools the machine picks among plausible next words, like weighted dice; ask again, rephrase, request a second version
Variability is fuelTwenty ideas cost nothing and hand you a menu; generate plenty and pick the best
Your prompt cannot switch the dice off. It decides which game the dice are playing.Tight instructions and concrete examples narrow the menu when you need consistency
UpgradeWhat you doWhen it earns its keep
Ask for steps (chain-of-thought)Ask the machine to walk through its steps, with a reason for every judgmentAnalytical tasks; the visible reasons expose a hidden yardstick, like extreme-language scoring in the Boston Globe comment example
Show examples (few-shot)Give two or three labeled samples of what you wantWhen describing what you want is hard but showing it is easy

Aging note: when the course was filmed in 2024, think step by step was a measurable trick. Many newer systems, often described as reasoning models, now do much of that on their own. Visible steps still let you check the work, but the written explanation is itself output to check.

Roles worth borrowing: mentor, critic, tutor, student, interviewer, simulator.

Setup tipWhy
Open with the words “you are”State an identity rather than asking it to pretend
Say you will speak turn by turnOtherwise it may write the entire two-sided conversation itself
Give the character a spinePractice negotiators cave instantly unless told to be tough and hold certain lines
End with an out-of-role critiqueAsk it to step out of the role and critique your performance; that turns a simulation into coaching
PitfallCorrection
Judging the machine on a one-line promptGive a real task the three-part treatment before deciding what the tool can do
Telling it what not to doEvery forbidden word you name is a word you placed on the table
Living in one endless threadOld dead ends leak into new replies; summarize and start clean
Believing the characterA persona changes style and stance, not knowledge; a practice negotiator does not know any company’s internal salary bands. Rehearse with the character, verify with sources
LineMeaning
”having the first result of your first Google search color what you think of the internet”One of the course’s teachers on judging the technology by a single weak reply
”giving an AI personality”The course’s name for the persona move
Ask well, and good answers stop being luck.The lesson’s closing line: prompting is clear thinking made visible