You will be able to have the assistant interview you to fill gaps in your brief before it starts.
Aisha's next job was an onboarding plan for six graduate hires joining the firm's audit team in August. She knew the context paragraph mattered, so she wrote one. It covered the firm, the team, the start date and what the plan was for. It still left out a dozen things she knew and had not thought to say, because she had been living with them for weeks and they no longer felt like information.
This lesson is about a way of catching those gaps before the work starts: you let the assistant interview you.
At the end of your request, add something like: "Before you start, ask me up to five questions about anything you need to know to do this well." Then stop and wait for the questions.
Aisha added that line to her onboarding request. The questions that came back were:
Will the graduates have any accounting qualifications or exam modules done, or are they starting from scratch? Who will they shadow, and how much of those people's time is available? Is there a budget for external training or social events? Should the plan cover only the first week, the first month, or the whole probation period? Are there firm policies or compliance courses they must complete in a fixed order?
She knew the answer to every one. She had not written any of them down. The fourth one mattered most: she had been picturing a three-month plan, and her draft request said nothing about length. Without the question, the model would have picked a period on its own, quite possibly a week.
The limit of five is deliberate. With no limit, some assistants return fifteen questions, many of them minor, and answering them becomes a chore. Five forces the model to pick the ones that matter most. For a smaller task, three is plenty.
Good questions bring out assumptions you did not know you were making. The usual ones are the audience, the budget, the deadline, the length and depth of the output, what has been tried before and who has to approve it. These are exactly the things lesson 1.2, Give context the way you would brief a colleague, asked you to include, and the questions-first approach is a backstop for when you forget.
The questions also tell you something about how the model has read your request. If it asks something you thought was obvious, your brief was less clear than you believed. If it asks nothing about an area you care about, it may be planning to treat that area lightly, and you can say so before it does.
You do not need to write essays in reply. Short answers work: "Two have part-qualifications, four are fresh graduates. Each will shadow a senior associate for about half their time. Small budget for one team lunch a month. First three months. Yes, the data protection and anti-money laundering modules must be done in week one."
Then add one more step before the work begins. Ask the assistant to restate the brief in its own words: "Before you write the plan, summarise in five bullet points what you are going to produce and for whom." This takes a few seconds to read and shows you whether your answers landed. When Aisha did it, the summary said the plan would cover "the first three months for six fresh graduates", which flattened her answer about the two with part-qualifications. She corrected that in one line, and the final plan gave those two a faster track through the technical modules.
The restatement is your last cheap chance to fix a misunderstanding. After it, you move into the kind of step-by-step work lesson 3.2, Ask for the plan before the work, described: outline first, then section by section.
Questions first works best for open tasks where there are many reasonable ways to do the job and the right one depends on details only you know. Plans, proposals, job applications, event programmes, training material and tricky emails all fit. A job application is a good example. Ask an assistant to help with a cover letter and invite its questions first, and it will usually ask which parts of your experience you want to lead with and what you know about the employer, which are exactly the things that make a letter specific.
It adds little to closed tasks. If you want a paragraph shortened to 80 words, or a table converted into a list, there is nothing to ask about, and the questions just slow you down.
It also does not replace a good brief. The model can only ask about what it can imagine being relevant. It will not ask whether one partner refuses to take graduates to client sites in their first month unless something in your request hints at it. Write the best context you can, then let the questions catch what you missed.
The test of whether this is worth the extra step is to try it on something real and compare. Pick an open task you need to do soon, one where you would normally write a single prompt and hope, and keep your usual prompt for it close by.
Use the questions-first approach on a real task, answer the questions, and compare the final output with one from your original prompt.
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