learn-prompt-engineering-with-phoebe / Leader session 2 of 6
Learn Prompt Engineering with Phoebe · Leader track · Session 2 of 6

Ask the right question

Session 1 taught you to brief AI like a new hire. Today we get concrete: the five jobs you can actually hand over, the two principles that make any ask land, and how to read a weak answer the way a doctor reads a symptom.

🟢 Leader track C-level, boards & managers No tech required Bring 3 real asks 30 min self-read · 45 min live
0-3 · Welcome 3-25 · Five jobs, two principles 25-40 · The brief makeover, live 40-45 · Q&A
Part 0

From delegation to the ask itself

Last session the Meridian Retail exec team learned the mental model: AI is a brilliant, literal new hire, and output quality is set by delegation quality. This session is the practical sequel. What kinds of work can you actually hand it? What makes an instruction land? And when the answer comes back weak - as first answers often do - how do you know exactly what to fix instead of just trying again louder?

Live - presented in session Self-study - read after class ★ Try it in your next sitting Any model · any chat app
★ What you walk out with today A five-job taxonomy that tells you what to ask for before you type a word, Andrew Ng's two principles of effective prompting in plain executive language, a specificity ladder you can climb one rung at a time, and a diagnosis table that turns every disappointing answer into a precise one-line fix. Plus the live makeover of the Meridian CMO's campaign brief - the one that sent her back to the agency in session 1.
Part 1 · the task taxonomy

The five jobs you can give AI 8 min live

Andrew Ng's famous prompting course organises almost everything a language model does into a handful of task families: summarize, infer, transform, expand - plus the one leaders use most, create. Naming the job before you type is the single fastest upgrade to any ask, because each job wants a different brief.

1 · Summarize Long in, short out. 40 tickets, 5 themes 2 · Infer Read and label. Tag reviews pos / neg 3 · Transform Same content, new form. Memo to store email 4 · Expand Short in, long out. 6 bullets, full brief 5 · Create New options from zero. 20 campaign angles Name the job before you type. Each job wants a different brief - and mixed jobs in one ask are the top cause of mush.
🔍 Click to zoom - the five jobs, each with a one-line Meridian example
LiveThe five jobs, with Meridian's actual week5 min▶

Here is each job with a request the Meridian team really made this month. Notice how naming the job makes the rest of the brief almost write itself:

JobYou are asking it to...Meridian example
SummarizeCompress long material without losing what mattersDana: "40 complaint tickets into the top 5 themes, with counts and one quote each"
InferRead and judge: classify, extract, detect toneThe CMO: "Tag these 500 product reviews positive / negative / mixed, and pull out every mention of delivery"
TransformKeep the content, change the form: rewrite, translate, reformatDana: "Turn this policy memo into a friendly two-paragraph email for store managers"
ExpandGrow a seed: bullets into a draft, notes into a memoThe CFO: "Draft a one-page board note from these six bullet points, formal tone"
CreateGenerate options that did not exist: ideas, names, anglesThe CMO: "20 distinct campaign angles for the summer sale - no two alike"
Real world

The underused pair: most executives discover summarize and expand in week one and stop there. The quiet workhorses are infer and transform - tagging, extracting, reformatting. They are the jobs that eat the most staff hours, and the ones AI does most reliably, because the answer is checkable against the input you gave it.

Self-studyName the job before you type - the 5-second habit2 min read▶

Before your next ask, finish this sentence in your head: "I am asking it to ______ this." If the blank is summarize, lead with the material and the compression target. If it is create, lead with the quantity and the constraints. If you cannot fill the blank, the model cannot either - and you will get an answer that half-does three jobs.

  • One ask, one job. "Summarize these tickets and also draft a response plan and make it funny" is three jobs. Chain them: summarize first, then expand the plan from the summary you approved.
  • The job picks the brief. Summarize wants a length and an audience. Infer wants the exact labels. Transform wants the target format. Expand wants the skeleton. Create wants volume and variety rules.
Part 2 · the principles

The two principles 8 min live

Ng's course boils effective prompting down to two principles, and they have aged beautifully. One: write clear and specific instructions. Two: give the model room to work - context, and a reason. Everything fancier is decoration on these two.

RUNG 3 · SHARP 3 captions for young families near our stores, voice like the sample below, under 25 words, each ends with a reason to visit RUNG 2 · BETTER Write 3 Instagram captions for our summer sale, upbeat tone, under 25 words each RUNG 1 · VAGUE Write something about our summer sale Same ask, three rungs. Each rung adds one ingredient - specific is not longer for its own sake, every word buys precision.
🔍 Click to zoom - the specificity ladder: one ask upgraded rung by rung
LivePrinciple 1 · clear and specific - which is not the same as long4 min▶

The most common misreading of this principle: people hear "specific" and write longer. Length is not the point. Precision is. A 15-word ask that names the audience, the format, and the limit beats a 200-word ramble that names none of them.

Vague (short and useless)Specific (short and sharp)
"Make this better""Cut this to half its length without losing the three numbers"
"Write something professional""Write it for a board that has 90 seconds per paper"
"Give me some ideas""Give me 20 ideas, no two from the same category"
"Summarize this""Summarize this into 5 bullets a store manager can act on Monday"

Climb the ladder one rung at a time. You rarely need rung 3 on the first try - but you should always know which rung you are standing on.

LivePrinciple 2 · give it room to work - context, and a reason4 min▶

The second principle is about generosity: give the model the material and the motive. Context you know from session 1 - paste the real thing. The motive part surprises people:

Say why - it measurably helps Anthropic's own prompting documentation advises explaining the reason behind an instruction, because knowing the purpose improves results. "Under 200 words" is an order. "Under 200 words because it goes on one slide for a 90-second board item" is an order the model can use to make a hundred small decisions correctly - what to cut, what to keep, what tone fits.

Think of any brief you have given a person. "Do it this way" gets compliance. "Do it this way, because here is what it is for" gets judgment. Models respond the same way - which should not be surprising by now, because they learned from text written by people.

Real world

Dana's why test. Dana added one sentence to her weekly ops summary ask: "This goes to the exec team who have 2 minutes; they only care about what changed and what needs a decision." The output stopped including background she already knew - without her ever listing what to exclude. The reason did the excluding for her.

Self-studyWhere the two principles come from - and why they still hold2 min read▶

These two principles anchor Andrew Ng and Isa Fulford's "ChatGPT Prompt Engineering for Developers" - one of the most-taken AI courses ever. It was written for developers, but the principles have no code in them, and Anthropic's published best practices open with the same three moves: be explicit, add context and motivation, be specific about everything that matters.

Three years of fast model progress later, plenty of 2023 tricks have died (session 1 covered the graveyard). These two principles did not - because they are not model tricks. They are delegation, formalised. As models improve, sloppy asks get better answers too, but the gap between a vague ask and a sharp one stays wide. It is the one gap the vendors cannot close for you.

Part 3 · the diagnosis

Read the miss 6 min live

Session 1 gave you the anatomy of a strong ask: goal, context, constraints, format, example. Here is the payoff. A weak answer is not a verdict on the tool - it is a symptom, and the symptom tells you exactly which ingredient your brief was missing. Diagnose, add one thing, go again.

LiveThe diagnosis table - from symptom to one-line fix6 min▶
Symptom - what came backMissing ingredientThe fix
Right topic, but generic - could be about any companyContextPaste the real document, numbers, or situation. "Our" means nothing to a day-one hire.
Beautiful answer to a question you did not askGoalSay what done looks like: the decision it supports, the audience it serves.
Three pages when you needed three lines; or hedged, jargon-heavy, off-limits topics includedConstraintsState length, tone, and the rules: what to include, what never to mention.
Content is fine but the shape is unusable - prose when you needed a tableFormatName the shape: "a table with these 3 columns", "an email under 150 words".
Right shape, wrong voice - bland, or nothing like how you writeExamplePaste one gold sample and say "match this". One example beats ten adjectives.

The discipline: add only the missing ingredient. Rewriting the whole prompt from scratch each round teaches you nothing. Fixing one named gap per round teaches you the craft in a week.

Self-studyWhy "try again but better" fails - and diagnosis works2 min read▶

When an answer disappoints, the untrained reflex is to re-ask with more emphasis: "No, really summarize it WELL this time." That adds emotion, not information - and the model already tried its best with what it had. The trained reflex is a 10-second diagnosis: which row of the table is this? Then one surgical addition.

This is the iterative loop from session 1, now with a steering wheel. First answer, read the miss, add the ingredient, second answer. Two rounds of diagnosis routinely beat five rounds of frustration - and unlike frustration, the skill compounds: after a month you pre-empt the miss and write the ingredient in the first ask.

The boardroom moment

The makeover: the CMO's campaign brief ★ 15 min · work it live

In session 1 you heard how the Meridian CMO pasted a one-liner, got bland copy three times, and went back to the agency. Today she gets her makeover. Watch the anatomy assemble - then run the same upgrade on one of the three real asks you brought.

Prompt A - what the CMO sent (three times)Write social copy for our summer sale.
Prompt B - the upgrade (steal this shape)You are helping the CMO of Meridian Retail, a 2,000-person retailer with 80 stores and an online arm. Task: write social copy for our summer sale - 5 Instagram captions and 2 Facebook posts. Audience: young families living within 15 minutes of a Meridian store. They shop for value but respond to warmth, not discount-shouting. Why this matters: the sale clears summer stock before autumn ranges land, so the goal is store visits this fortnight, not brand awareness. Brand voice - match this caption we loved last year: "School's out. Snack drawer's empty. We've got you - and the ice cream is 2 for 1." Constraints: - Under 25 words per caption - No exclamation marks, no "unbeatable prices" - Every caption ends with one concrete reason to come in this week If anything above is unclear, ask me before writing.

Run the one-liner first. Send Prompt A as-is. Keep the bland result open in a tab - it is your before photo, and it is what "the AI is mediocre" actually looks like from the other side.

Name the job. This is create plus a little transform: new options, in a defined voice. That tells you the brief needs volume rules, a voice sample, and format constraints - the taxonomy just wrote your checklist.

Assemble the anatomy. Audience, the why, the voice sample, format, constraints. Notice the sample caption does more work than any adjective - "warm, playful, family-focused" describes it; the sample IS it.

Compare out loud and name the winner. Which ingredient moved the output most? For voice-driven work it is almost always the example. For analytical work it is almost always context. Knowing your pattern makes the next brief faster.

Now yours. Take the best of your three real asks and climb it to rung 3. Golden-rule it with your neighbour: if they can execute your brief cold, so can the model.

Keep the winning brief The CMO's Prompt B is now a template: next campaign she changes the audience, the why, and the sample - 90 seconds of editing instead of three rounds of bland. Any brief that worked once is an asset. Save it where you will find it. Session 5 turns this habit into how you spec projects with your data team.
Homework

Three things before session 3 ◐ 20 min total

Source material

What this session covers

Leader-level coverage of the sources below - working ideas in plain language, honestly flagged where the depth lives in the builder track. Official certificates and videos stay with the vendors; links are in the course map.

✓Andrew Ng - task taxonomy: summarize, infer, transform, expandPart 1 · no code (DeepLearning.AI, ChatGPT Prompt Engineering for Developers)
✓Andrew Ng - the two principles of promptingPart 2 · clear and specific + give the model room (DeepLearning.AI)
✓Anthropic best practices 1-3: explicit, context + motivation, specificPart 2 · the "say why" evidence (claude.com/blog)
✓Iterative prompt development - the loop, with diagnosisPart 3 + makeover · session 1's loop gains a steering wheel
◐Examples and few-shot prompting in depthVoice sample only today; the full craft lives in Builder session 2
Check yourself

Three questions before you go 🎯 ◐ 90 seconds

1 · Dana wants 500 store-visit reports turned into a one-page brief for the exec team. Which job is she delegating?

Long in, short out is summarize - so the brief needs a compression target ("one page") and an audience ("exec team"). Naming the job tells you what the brief must contain.

2 · "Write clear and specific instructions" means your prompts should be...

Specific is not long. "Cut this to half without losing the three numbers" is nine words and rung-3 sharp. Length without precision is just a longer vague prompt.

3 · The AI returns a polished answer about retail in general - nothing about your company. Which ingredient was missing?

Generic output is the signature symptom of missing context. The model filled the gap with what it knows about retail at large. Paste the real material and the answer becomes yours.

Leader session 2 cheat sheet · pin this

The five jobsSummarize · infer · transform · expand · create. Name the job before you type; one ask, one job.
Principle 1Clear and specific. Specific is not long - precision about audience, outcome, and limits.
Principle 2Give it room: context plus motivation. Saying WHY measurably improves what comes back.
The specificity ladderVague, better, sharp. Climb one rung per rewrite; every added word should buy precision.
Read the missGeneric = context. Wrong question = goal. Too long = constraints. Wrong shape = format. Wrong voice = example.
Fix one thingAdd only the missing ingredient and re-run. Full rewrites teach nothing; diagnosis compounds.
The sample beats adjectivesOne gold example of the voice you want outperforms any description of it. Build a sample pack.
Keep winning briefsA brief that worked is a reusable template - edit the audience and the why, not the whole thing.