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30 minIntermediate

Picking the right problems for AI

Every leadership team now has a list of things to "do with AI". Some are excellent fits. Many are better solved with a rule, a report or a better form, and a few are dangerous. This lesson gives you a quick, honest way to tell them apart, and the words to say no without sounding afraid of the future.

By the end you can

  • Say when a rule, a query or a spreadsheet beats AI, and when AI beats them
  • Put a number on the cost of being wrong, split by type of question
  • Choose between assist and automate from the cost of errors and how easy they are to catch
  • Break a big AI idea into the parts that fit and the parts that don't
  • Write a one-page memo that compares AI candidates and recommends one

The everyday picture

A vending machine and a new shop assistant can both hand you a cold drink. The vending machine is cheap, never tired and always gives the same can for the same button. It can't help when you ask "something without sugar that my grandmother would like". The new assistant can. She understands messy requests in any words, deals with things nobody planned for and is right most of the time. She also costs more, sometimes gets it wrong, and needs a manager to check her work in her first months.

Nobody hires a person to dispense cans, and nobody asks a vending machine to handle a complaint. Picking problems for AI is the same choice. A language model is the new assistant: excellent with messy language, imperfect, and worth it only where its flexibility pays for its mistakes. A rule in code is the vending machine.

Where AI wins and where rules win

Language models are strong when the input is messy and varied: free text in many phrasings and languages, photos of documents, long procedures. They help most when many answers are acceptable, such as a summary or a draft, and when "mostly right and quick to check" beats "slow". They also help when the variety is too large to write rules for. Nobody can list every way a store manager might ask about a stuck delivery.

Rules, code and spreadsheets win when:

  • The logic is exact and stable. Mangrove's expiry procedure, EX-3, says items two days before expiry get a 30% markdown. That is one line of code in the Store app, right every time.
  • The answer is arithmetic. Till totals, stock differences, margins. Models are unreliable at exact arithmetic unless they call a tool that does it.
  • The data is already in tables. "Which stores have stock differences over $100?" is a query. A dashboard answers it for everyone at once.
  • The same answer is required every time, with an explanation an auditor can follow.

"AI" is not one tool either. Forecasting tomorrow's demand from sales history is a prediction from structured numbers: a job for a forecasting model built by a data team and judged by forecast error. Spotting empty shelves in photos is computer vision. A chat model is the right tool for language. Ask which kind of AI a proposal means before anyone writes a plan.

A useful lens comes from the book Prediction Machines (Agrawal, Gans and Goldfarb, 2018): AI makes prediction cheap, meaning filling in missing information, such as which procedure answers this question. Judgement, deciding what to do given what you value, stays with people or with rules people wrote. For every idea, name the prediction and name who owns the judgement.

Quick check

Which of these is the best fit for a language model?

The cost of being wrong

Every AI feature is wrong some of the time. The question for a PM is what a wrong answer costs, how often it happens and who catches it before it does damage. Put it in one line:

Output
Expected cost of errors = volume x error rate x share NOT caught x cost of one uncaught error

Then compare it with the value of the right answers. Do this separately for each type of question, because one average hides the case that sinks you. Here is the first pass Imran did for Ask Ops, per week, on today's volume:

Output
Rule questions, 1,350 a week, split by what a wrong answer costs:
Most of them     1,200 x 8% wrong x 50% not caught x $6     = ~$288
  (a wrong markdown, a re-done task; citations let managers catch half)
  value: 1,200 x ~$1.10 (6 desk minutes + 5 manager minutes) = ~$1,320
Customer data      150 x 8% x 50% x $2,000 (an incident)    = ~$12,000
  value: 150 x ~$1.10                                        = ~$165

The same 8% error rate is fine for procedure questions and unacceptable for customer data. The fix is a different design. For customer data, use a hard rule in code that never returns an address or phone number, with the model only explaining CD-1, the customer data procedure. Releasing customer data must be impossible by design, whatever the model does.

Three more things change the cost of an error:

  • Errors are asymmetric. "Can I give this caller the customer's address?" answered yes by mistake is a privacy incident. Answered no by mistake costs one minute. Design for the expensive direction.
  • Reversible or not. A wrong answer that someone reads can be corrected. A refund sent, stock adjusted or a supplier emailed may not be.
  • Ease of checking. If a person can check the answer in seconds because the source and the data sit next to it, most errors are caught cheaply. If checking means redoing the work, the AI saved nothing.

Quick check

An AI feature is wrong 5% of the time on two question types. Type A errors cost about $2 and are obvious. Type B errors cost about $800 and look like correct answers. What follows?

Assist or automate

There is a spectrum between "AI suggests, a person decides" and "AI acts on its own". Lesson pm-50 turns it into autonomy levels for agents. For choosing a first problem, two questions decide where to start: how costly is a wrong result, and how quickly can a person check it?

Quick to checkHard to check
Cheap if wrongAutomate, and spot-check a sample. Tagging desk questions by topic.Assist, and measure quality with evals. A weekly summary of what stores asked about.
Costly if wrongAssist with approval. AI drafts, a person approves with the evidence in view. A supplier correction for a stuck GRN.People decide. AI may find information. Approving a $2,000 write-off; anything that releases customer data.

Assist and automate create value in different ways. Assist saves search time and spreads expert knowledge to 320 stores, but a person still spends time on every case. Automate saves the whole task, but needs a much lower error rate, because nobody looks before it happens. Many good AI products start as assist and earn automation one task type at a time, with evidence from real use.

Assist only works if the person can really check. If the evidence isn't on screen, or approvals come in a stack of fifty, people approve without looking. Psychologists call this . Then you have automation with an extra click and someone to blame. Lesson pm-48 shows how to design checking that people actually do.

An AI idea Is there an exact, stable rule? yes Write the rule such as EX-3 no Messy text, photos or many languages? no Query or forecast data in tables yes Do experts agree what good looks like? no Define good first 50 agreed examples yes Costly if wrong? price the uncaught error no Automate with spot checks yes Quick to check with the evidence on screen? yes Assist: AI drafts a person approves no People decide AI only finds information
A first screen for any AI idea. Rules and queries come first because they are cheaper and always right. An idea where experts can't agree on a good answer goes back for definition. Then the cost of being wrong and the ease of checking set the starting level.

Screening AI ideas, and saying no well

Run every idea through the same seven questions before anyone builds. Each needs an answer with a number or a name, not an adjective.

  1. Pain. How often does the problem happen, how long does it take, and for how many people? Measured today, not imagined.
  2. The boring baseline. Would a rule, a report, better search, a clearer form or a fixed procedure solve most of it? Try that first, or at least price it.
  3. Input. Is the input messy language or images (AI's strength) or structured data (rules' strength)?
  4. Data. Do we have the knowledge or data the answers need, is it correct, and are we allowed to use it?
  5. Cost of being wrong. Per type of case, in money and in trust, and who catches errors.
  6. Can we measure it? Could experts write 50 real examples with agreed good answers? If they can't agree what good is, AI won't settle it. This set becomes the start of your evals (pm-49).
  7. Unit economics. Cost per answer (pm-46) against value per answer, including the time people spend checking.

Most ideas that fail the screen fail on question 2 or question 6. That is good news: you have found a cheaper fix, or a definition problem worth solving anyway.

Saying no well means saying "not this, not yet, and here is what would change my mind", with the alternative attached. "AI markdowns" becomes "the EX-3 rule in the Store app in two weeks". "AI forecasting" becomes "a forecasting pilot with the data team, judged by forecast error". People asking for AI usually want the outcome, not the technology, and they accept a faster route to it.

Big ideas usually contain several problems. Ask Ops is a good example. When Tomás, Mangrove's data analyst, tagged a sample of 400 desk questions, they fell into three groups with different fits, shown below.

Quick check

An idea fails question 6. Store experts disagree about the right answer to a third of the sample questions. What do you do?

3,000 questions a week from 320 store managers 1,350 1,050 600 What's the rule? 45% Why is this happening? 35% Please fix it 20% procedures + citations read-only live data desk acts; AI drafts later Ask Ops v1: assist, answers only phase 2, approve
One big idea, three problems. Rule questions fit retrieval with citations; status questions fit read-only tools on live data. Requests to fix something involve actions, so they stay with the ops desk in v1 and come back as drafts for approval in a later phase.

Do it

Write a one-page AI opportunity memo that compares at least three candidates and recommends one.

  1. Write each idea as a measured problem

    Replace "use AI for X" with who has the problem, how often, how long it takes and what it costs today. If nobody has measured it, take a sample this week.

  2. Write the boring baseline next to each

    The rule, report, search, form or procedure change that could solve most of it, and what it would cost.

  3. Split each idea into case types

    Tag a sample of real cases. Different types often need different designs, or no AI at all.

  4. Price being wrong, per type

    Volume × error rate × share not caught × cost of an uncaught error, against the value of right answers. Note which errors are asymmetric or irreversible.

  5. Choose a starting level

    Rule, query, people decide, assist with approval, assist, or automate with spot checks, per type.

  6. Write the memo

    Markdown
    ## AI opportunities: recommendation (Imran, Store app and back office)
    Recommendation: build Ask Ops first, as assist (answers only).
      Second: the app-review summariser. No AI for markdowns.
    
    | | Ask Ops | Review summariser | Invoice auto-approval |
    |---|---|---|---|
    | Pain today | 3,000 q/week, 300 desk h, ~3 h wait | 10,000 reviews/month unread | ~900 differences/month, 2 buyer days |
    | Boring baseline | better search of procedures: helps rule questions only | a tag dashboard: no themes | stricter tolerance rule: covers ~40% |
    | Input | free text, several languages | free text | numbers + scanned invoices |
    | Data ready? | 10 procedures, live GRN/stock/order APIs | yes | invoice scans poor in 1 DC |
    | Cost of wrong | low for rules; customer data handled by a code rule | low | high, hidden |
    | Measurable? | experts agreed 46 of 50 sample answers | yes, 50 reviews labelled | not yet: buyers disagree |
    | Starting level | assist; status questions read-only | automate + weekly spot check | later: drafts for a buyer |
    | Unit economics | ~1.5 cents/answer vs ~$1.10 of time | small | unknown |
    
    Risks: managers over-trust answers (mitigation: sources on every answer);
      question volume grows (budget for 2x).
    What would change my mind: fewer than 70% of pilot answers marked solved,
      or any customer data returned in testing.

Bring it to your team

Ask these whenever an AI idea reaches a planning meeting.

  • What is the problem in numbers today, and who measured it?
  • What is the boring alternative, and why isn't it enough?
  • Which kinds of case are inside this idea, and does each one need AI?
  • What does a wrong answer cost for each kind, and who catches it before it does harm?
  • Could our experts write 50 examples with agreed good answers this week?
  • Which kind of AI do we mean: a language model, a forecast, or image recognition?

Red flags

  • "Use AI to…" with no measured problem behind it.
  • An exact, stable rule being sent to a language model.
  • One error rate quoted for every kind of case.
  • "A person will check it" with no time, evidence or screen designed for checking.
  • Experts disagreeing on the right answer, and the plan is to let the model decide.

Practice

Screen four ideas

For each idea, say whether it suits a language model, another kind of AI, or no AI, and the starting level. Give one reason based on the screen.

  1. Rider app: "AI picks the order in which a rider delivers a batch of orders."
  2. Partner app: "Shop owners type their order in their own words and language; AI builds the cart for them to confirm."
  3. Store app: "AI decides whether to reject a damaged delivery at the door."
  4. Back office: "AI writes each store's weekly performance summary for its manager."
  • Idea 1 is a routing problem for optimisation algorithms and maps, not a language model
  • Idea 2 suits a language model as assist: the owner confirms the cart, so errors are caught
  • Idea 3 keeps a person deciding (RC-1), because errors are costly and judgement is local; AI may show the checklist
  • Idea 4 splits: numbers come from a query, and AI only writes the words around them
  • Each answer gives a reason tied to input type, cost of error or ease of checking
Show a model answer
  1. No language model. Delivery order is a routing optimisation over distances and time windows; use routing algorithms and map data, judged by minutes per order.
  2. Language model, assist. Messy text in many languages is its strength. The owner sees the cart and confirms, so most errors are caught for free. Measure with 100 real messages.
  3. People decide. A wrong rejection or acceptance costs money and supplier trust, and depends on what the clerk sees. AI could show RC-1's checklist and fill the paperwork after the decision.
  4. Split. Sales, stock accuracy and order cuts come from a query, exact every time. A model writes two short paragraphs around the numbers, and a code check confirms every number in the text matches the query.

Break down a vague ask

The managing director says, "Use AI to fix stock errors." The facts: stock accuracy is about 82%, and about 9% of app orders have an item cut because it is out of stock. In a sample of 200 stock differences, 35% came from receiving mistakes on the goods received note, 25% from damage or theft not recorded, 20% from items scanned as the wrong product at the till, and 20% from counting errors. Split the ask into problems, say which parts suit AI and which kind, which suit rules or process, and propose a first candidate with its starting level.

  • You split the ask by cause and keep the numbers
  • You name at least one part where a rule or process change beats AI
  • Any AI part names the kind of AI and the starting level
  • Your first candidate is justified by size, fit and cost of being wrong
  • You say how you would measure success (stock accuracy, order cuts)
Show a model answer
Markdown
Receiving mistakes (35%): biggest share. AI can read the supplier's
  delivery note photo and pre-fill quantities; the clerk confirms each
  line against the count (assist). Also a rule: block signing a GRN
  with a line 20% off the order without a second scan.
Damage and theft not recorded (25%): process first. A one-tap
  "damaged" button in the Store app and a weekly check; no AI needed.
Wrong product scanned at the till (20%): rules and data. Flag
  products with the same price scanned in swaps; fix lookalike
  barcodes in master data.
Counting errors (20%): process. Guided counts in the Store app
  (ST-4), recount when a difference is over $100.
First candidate: delivery note reading at receiving, assist level,
  because it is the largest cause, the input is messy paper, and the
  clerk's confirmation catches errors before the GRN is signed.
Measure: GRNs corrected later (1 in 12 today), stock accuracy,
  share of app orders with a cut item, in pilot vs other stores.

Check yourself

The head of buying wants "an AI chat where buyers ask for any product's margin". Margins are a column in the data warehouse. What is your best response?

An idea: AI reads photos of supplier delivery notes and fills in quantities on the GRN. A wrong quantity costs a later correction. Which starting level fits best?

Two candidates promise the same time saved. In A, errors are cheap and obvious to users. In B, errors are rare but expensive and look like correct results. Which do you start with?

Flashcards

Open my review

Key takeaways

  • Language models win on messy language and variety. Rules, queries and spreadsheets win on exact logic, arithmetic and data already in tables.
  • Price the cost of being wrong for each type of case. The same error rate can be fine for one and unacceptable for another.
  • Start at assist or automate based on how costly errors are and how quickly a person can check them. Automation is earned with evidence.
  • Screen every idea with the same questions, especially the boring baseline and whether experts agree on what good is.
  • Say no with an alternative and the evidence that would change your mind.

Further reading

  • Prediction Machines: The Simple Economics of Artificial Intelligence, Ajay Agrawal, Joshua Gans and Avi Goldfarb, Harvard Business Review Press, 2018 (updated edition 2022)
  • People + AI Guidebook, Google PAIR, read in 2026, especially the chapter on user needs and defining success
  • Building effective agents, Erik Schluntz and Barry Zhang, Anthropic, 2024, on finding the simplest solution first
  • Your AI Product Needs Evals, Hamel Husain, 2024, on why a measurable definition of good comes first
Episode transcriptSome AI ideas are spreadsheets in disguise · about 10 minutes · tap any line to play from there
  1. NadiaImran, what came back from the leadership off-site?
  2. ImranFive AI ideas and a request for a plan by Friday. Ask Ops, AI markdowns, AI demand forecasting, AI approving supplier invoice differences, and a summariser for app reviews.
  3. NadiaAnd your gut says?
  4. ImranThat at least one of them is a spreadsheet in disguise. But I need a better argument than my gut.
  5. NadiaThat's today. How to tell the good AI problems from the ones a rule solves better, and how to say no without sounding scared of the future.
  6. NadiaStart with a picture. A vending machine and a new shop assistant can both hand you a cold drink. The machine is cheap, never tired, and gives the same can for the same button every time.
  7. ImranBut it can't help when I ask for something without sugar that my grandmother would like.
  8. NadiaRight. The new assistant can. She understands messy requests in any words. She's right most of the time, costs more, and needs her manager to check her work for a while.
  9. ImranAnd nobody hires a person to dispense cans.
  10. NadiaOr asks a vending machine to handle a complaint. A language model is the new assistant. A rule in code is the vending machine. Pick the one the job needs.
  11. ImranSo when does the model win?
  12. NadiaWhen the input is messy and varied. Free text in many phrasings and languages, photos of documents, long procedures. When a draft that's quick to check beats a slow perfect answer. And when there's too much variety to write rules for.
  13. ImranLike all the ways a store manager can ask about a stuck delivery.
  14. NadiaExactly. Rules win when the logic is exact and stable, when the answer is arithmetic, when the data already sits in tables, and when an auditor needs the same answer every time.
  15. ImranWhich is my markdown idea. The expiry procedure, E X three, says two days before expiry, thirty percent off.
  16. NadiaOne line of code in the Store app, right every time. No model needed. And watch the word AI itself. Demand forecasting is a prediction from sales numbers. That's a forecasting model for the data team, judged by forecast error, not a chat model.
  17. ImranI like the line from Prediction Machines. AI makes prediction cheap, and judgement stays with people.
  18. NadiaSo for every idea, name the prediction and name who owns the judgement. Now the part most teams skip. Every AI feature is wrong some of the time. What does a wrong answer cost?
  19. ImranYou wrote a one-line formula for that.
  20. NadiaVolume, times error rate, times the share nobody catches, times the cost of one uncaught error. Then compare it with the value of the right answers. And do it per type of question.
  21. ImranMy first guess was one number for all of Ask Ops. Eight percent wrong, fine.
  22. NadiaAnd that's the trap. Take the rule questions. For most of them a wrong answer is a wrong markdown or a re-done task, maybe six dollars, and citations let managers catch about half. Roughly three hundred dollars a week of errors against about thirteen hundred of value.
  23. ImranBut about a hundred and fifty a week are about customer data.
  24. NadiaSame eight percent, but one uncaught error can be a privacy incident costing thousands. That's about twelve thousand dollars a week of expected damage. The fix is a hard rule in code that never returns an address or phone number. The model only explains the customer data procedure, C D one.
  25. ImranImpossible by design, whatever the model does.
  26. NadiaNicely put. Errors are also asymmetric. Answering yes by mistake to, can I give this caller her address, is a disaster. Answering no by mistake costs a minute. And some actions can't be undone, like a refund sent or a supplier emailed.
  27. ImranWhich brings us to assist or automate.
  28. NadiaTwo questions set the starting point. How costly is a wrong result, and how quickly can a person check it? Cheap and quick to check: automate and spot-check. Costly but quick to check: AI drafts, a person approves with the evidence in view.
  29. ImranAnd costly and hard to check?
  30. NadiaPeople decide, and AI only helps find information. Approving a two-thousand-dollar write-off, or anything that releases customer data.
  31. ImranI worry about assist, though. If I hand a manager fifty approvals at once, she'll tap approve fifty times.
  32. NadiaThat's automation bias, accepting a machine's suggestion without checking because it's usually right. Then you've built automation with an extra click and someone to blame. Assist works only if checking is designed: the evidence on screen, one case at a time. That's the next lesson.
  33. ImranAnd the first diagram puts all this in order.
  34. NadiaIt's a decision tree. If you can see it, the questions run down the left and the answers sit on the right. If not, here it is in words. Is there an exact, stable rule? Then write the rule. Is the input messy text, photos or many languages? If not, it's a query or a forecast.
  35. NadiaDo experts agree what a good answer looks like? If not, define good first. Then, is it costly if wrong? If not, automate with spot checks. If it is, can a person check quickly with the evidence? Yes means assist with approval. No means people decide.
  36. ImranThe experts question surprised me. Why is that before cost?
  37. NadiaBecause if the people who know the work can't agree on the right answer, nobody can tell whether the AI is right. And the disagreement is usually a real problem in the procedure. Models don't settle it. They repeat whichever version they find.
  38. ImranThat happened to us. Experts agreed on forty-six of fifty sample answers, and the four disagreements led to a clearer refunds procedure.
  39. NadiaWhich is useful even if you never ship the AI. The full screen has seven questions. Pain in numbers. The boring baseline. Input type. Data you have and may use. Cost of being wrong. Can you measure it with fifty agreed examples. And unit economics.
  40. ImranAnd most ideas fail on two of those.
  41. NadiaThe boring baseline and the measurable one. That's good news, because you've found a cheaper fix or a definition problem worth solving anyway.
  42. ImranAnd big ideas often hide several problems. The second diagram shows what Tomás found when he tagged four hundred desk questions.
  43. NadiaThree thousand questions a week split three ways. About forty-five percent are, what's the rule. Those fit retrieval with citations. About thirty-five percent are, why is this happening. Those need read-only tools on live data.
  44. ImranAnd twenty percent are, please fix it.
  45. NadiaThose involve actions, so they stay with the ops desk in version one and come back later as drafts for approval. One idea, three designs.
  46. ImranSo here's how my memo came out. Ask Ops first, as assist. Markdowns become the E X three rule in the Store app, about two weeks. Forecasting goes to the data team as a separate project.
  47. ImranInvoice auto-approval later, as drafts a buyer approves, because the errors cost money and look like correct approvals. And the review summariser as a quick second, because errors are cheap.
  48. NadiaAnd the markdown rule shipped before the Ask Ops pilot even started.
  49. ImranWhich bought me a lot of credibility for the hard project.
  50. NadiaThat's how saying no well works. Not this, not yet, and here's what would change my mind, with a faster route to the outcome attached. People asking for AI usually want the outcome, not the technology.
  51. ImranSo the do-it is that memo.
  52. NadiaWrite each idea as a measured problem. Put the boring baseline next to it. Split it into case types from a real sample. Price being wrong for each type. Choose a starting level per type. Then one page with a comparison table and the evidence that would change your mind.
  53. ImranAnd in planning meetings I'll ask three things. What is the problem in numbers today, and who measured it? What's the boring alternative? And could our experts write fifty examples with agreed answers this week?
  54. NadiaGood. A pause-and-think. AI reads photos of supplier delivery notes and fills in the quantities on the goods received note. A wrong quantity means a correction later. What starting level? Take a second.
  55. ImranAssist. AI pre-fills each line, and the clerk confirms it against the count, with the photo beside it, before signing.
  56. NadiaRight. Costly if wrong, but quick to check at exactly the right moment.
  57. ImranLet me sum up. One: language models win on messy language, rules win on exact logic, arithmetic and data in tables. Two: price the cost of being wrong for each type of case, because one average hides the dangerous one.
  58. ImranThree: start at assist or automate based on cost of errors and ease of checking.
  59. NadiaAnd add this to the third. Automation is earned with evidence from real use, one task type at a time.
  60. ImranNext time: designing Ask Ops so managers trust it the right amount. Not too little, not too much.
Finished reading?Mark it complete to fill in its stop on your course line.

Use it at work

Cost estimate for an AI feature

A prompt, the expected reply length and traffic, and what it costs per call, per day and per month on each model.

Open in the AI Lab
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