Same task. Two ways to ask. Three real pairs that show what changes when you stop typing keywords and start writing prompts.
5 Min Read
The Crash Course covers how to think about prompting. This guide shows the same idea in practice. Three tasks a program manager runs into every week. For each one, the bad prompt is what most people actually type. The good prompt is what gets you something usable.
The outputs below are real — the kind of thing you'd get from Claude or ChatGPT today, not cherry-picked. The bad outputs aren't bad because the model is broken. They're bad because the prompt didn't give the model enough to work with.
Framework
A mental model you can reuse
Before the pairs, the framework that explains why one works and the other doesn't. Every good prompt has at least two of these three pieces — and when you can't manage the first two, the third is your escape hatch.
Who you are, what you're trying to do, who the output is for. Without this, the model can only return a generic template — that's the safest answer to a question with no context.
The form you want the output to take: format, length, tone, structure. "Three bullets, under 20 words each, for someone joining the project" produces something different from "summarize."
When (1) and (2) are too much to front-load — you're starting cold, you don't know what's relevant yet, the task is fuzzy — flip it. Make the model gather the context. It knows what's missing better than you do.
Copy-Paste
Before you help me with this, interview me one question at a time until you have everything you need to give me a useful answer. Don't draft anything until you've asked enough.
Used at the start of a chat, this often beats trying to write a perfect prompt cold. You'll see it in action in Pair Three.
Pair One
No context, no draft
Write a status update for my project.
What You Get Back
Act as my comms partner. I'm a senior PM at a B2B logistics company writing a Friday status update for my VP. My notes from this week: - Vendor contract finalized; kickoff Tuesday - Two engineers out sick; sprint slipped 3 days - Need her sign-off on the revised Q3 timeline Three short paragraphs covering: where we are, what's blocking, what I need from her. Direct, no fluff, under 150 words.
What You Get Back
Pair Two
The verb is the problem
Summarize this email thread. [15 emails pasted in]
What You Get Back
[continues for 11 more sentences]
Summarize this thread for someone joining the project this week. Three bullets, under 20 words each: (1) what's been decided (2) what's still open (3) the immediate next step If anything is ambiguous, flag it. [15 emails pasted in]
What You Get Back
Pair Three
When you can't front-load context
Help me write Q4 OKRs for my team.
What You Get Back
[continues with generic placeholders]
Before you help me draft Q4 OKRs, interview me one question at a time until you have everything you need: my team's role, current priorities, what we shipped last quarter, what's on fire, and what success looks like for Q4. Don't suggest anything until you've asked enough.
What You Get Back
Recap
Same framework, three different tasks.
Situation. Shape. Or interview.
Build the habit once, get it on every prompt. The pairs above all came down to the same three pieces — applied differently each time.
Confused by a term? See the Glossary →