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Treat AI like a brilliant freelancer with amnesia

It knows every trade and forgets you every time, so every job starts from day one.

  1. Job 1Mon

    Day 1

    Invitations for 200

  2. Job 2Tue

    Day 1

    An email to suppliers

  3. Freelancer · AIWed

    Day 1

    Knows
    every trade
    Knows your company
    nothing
    Remembers Tuesday
    nothing

Three jobs, three badges, and every badge says Day 1. Nothing from Monday reaches Wednesday.

The thought experiment

New hire · You

Day 1

  • Budget?
  • Who signs off?
  • What went wrong last time?

The thought experiment1 / 2

You're the new hire

Most of what you need to do the job well was never written down.

You ask

The obvious questions

Plan next year’s summer party for 200 employees across Europe

  • What is the budget?
  • Where does everyone stay?
  • Who signs off on the plan?
  • Dietary needs
  • Accessibility needs

The questions nobody thinks to ask

Context that even people forget to hand over, because it lives in feedback, in the culture or in habit rather than in any document .

  • What went wrong last time?
  • Which unwritten rules apply?
  • Which tools and suppliers may I use?

Switch roles

You are asked

Now you hand it over.

Your boss expects the plan by Friday, and the person taking over knows none of what you just learned .

DueFriday

  • Budget?
  • Stay?
  • Sign-off?
  • Last time?
  • Unwritten rules?
  • Suppliers?

The thought experiment2 / 2

A brilliant freelancer with amnesia, every time

Five traits to manage, or you pay the PRICE.

The freelancer

AI

  1. Give the same brief to a new freelancer, and get a different plan.

    Give the same prompt in a new chat, and get a different answer. 

  2. Hand over the job, and they work day and night, producing stacks of polished pages, whether they’re right or not.

    Send the prompt, and it produces pages in seconds, as many as you ask for, whether they’re right or not. 

  3. Ask a freelancer who knows every trade, and get expert answers, blind to your company and culture.

    Ask AI, trained on more text than anyone could read, and get the likeliest answer, blind to your company and culture. 

  4. Give a vague request, and they start without asking, fill the gaps with their own assumptions, and sell it to you as right.

    Give a vague prompt, and it starts without asking, fills the gaps with the most common answers, and replies with full confidence. 

  5. They bill every word they read and write, so one more question means paying to reread the whole file, their own pages included.

    It charges for every word it reads and writes, so one more message means paying for the whole chat again, its own answers included. 

Five moves to brief a freelancer

AI

Day 1

  1. Break it down
  2. Requirements first
  3. Interview yourself
  4. Evaluate each step
  5. Fresh start

Five moves to brief a freelancer1 / 1

Five moves to brief a freelancer with amnesia

Five traits cost you the PRICE. Five moves make it a BRIEF.

BRIEF counters PRICEProbabilisticRelentlessInformedConfidentEvery word billed
Break it downHand over one piece at a time. Small pieces leave less to get wrong and less to pay for.
Requirements firstWrite down what good looks like before work starts. The same brief then brings results that agree.
Interview yourself with AILet the AI ask you its questions first. Your unwritten context comes out before it guesses.
Evaluate each stepCheck every step against the requirements. A wrong turn is caught early, not after the last page.
Fresh start for each pieceOpen a new chat for each piece. Old words stop piling up in the bill and in the way.
Moves that counter each trait3 moves3 moves1 move2 moves2 moves

BRIEF in action

Requirements card

signed off

  1. Venue ADay 1
  2. Venue BDay 1
  3. Venue CDay 1

BRIEF in action1 / 1

Brief the venue

Plan the summer party for 200 people across Europe: one fresh chat per job, and two gates before your boss sees a plan.

  1. Break it down
  2. Interview yourself with AI
    1. AI asks you3 questions,
      1 you forgot 
    2. Interview · the worked chat

      1. You: /grilling (opens in a new tab) Plan our summer party: 200 people from five offices across Europe, about €150 each, two wheelchair users, some vegetarians.
      2. AI: Q1 · Format: one party in one place, or one in each office?
        • A) One venue, everyone travels
        • B) Five local parties

        Recommended: A, the point is that the offices meet.

      3. You: A.
      4. AI: Q2 · Capacity: do you size the venue for peak concurrent occupancy or for average dwell time?
        • A) Peak: 200 at once
        • B) Average: about 140, with staggered arrivals

        Recommended: A, the speeches bring everyone together.

      5. You: I don’t understand this. Can you explain it with an analogy?
      6. AI: Q2 · Think of booking a restaurant: one long table for everyone at eight, or tables that turn over through the evening?
        • A) One long table: room for 200 at once
        • B) Tables that turn over: room for about 140

        Recommended: A, everyone sits down for the speeches.

      7. You: A, one long table.
      8. The one you forgotAI: Q3 · Like a restaurant review: did last year’s party leave feedback worth reading first?
        • A) Yes, read it first
        • B) No, start fresh

        Recommended: A, it shows what to avoid.

      9. You: A. Good question, I had forgotten. It was too loud to talk, and people left early.
      10. You: /to-spec (opens in a new tab) Turn my answers into a specification.
  3. Requirements first
    1. Gate 1

      Requirements card

      • 200 guests
      • €150 per person
      • Step-free
      • Vegetarian menu
      • Quiet to talk

      Signed off

  4. Fresh start for each piece
  5. Evaluate each step
    1. Rank 3 venuesagainst the cardGate 2
  6. for your boss
    1. Venue plan

      by Friday

  • A fresh chat per job 
  • Checked against the requirements card
  • Waits for its turn