Brief It Like a New Hire

Imagine your newest hire showed up Monday morning with a business degree, flawless grammar, and the reading history of the entire internet. Sharp, eager, tireless. Also: they have never heard of your company, your clients, or you.

Would you hand them a task in six words? Of course not. You'd brief them first. That instinct — one you already have — is the whole trick to working with AI.

In Why AI Keeps Giving You Mediocre Answers we watched what happens when you skip the briefing: the model fills your blanks with the internet's average. This lesson is about what goes into the briefing instead.

Sarah's two-hour problem

Sarah is a fractional CFO in Toronto. She works solo, serves e-commerce brands, and every month owes each client a financial report that turns the numbers into plain English. The analysis takes her forty minutes. The writing takes two hours, and it's the part she dreads.

Her first attempt at handing it to Claude was "summarize this financial data into a client report." She pasted the numbers and got back something that read like a bank's annual filing — technically accurate, emotionally beige, nothing like the punchy one-pagers her clients pay for.

So she tried a different question. Not "what should I type?" but "what would I tell a junior analyst on their first day, before giving them this exact task?"

Quite a lot, it turns out. She'd explain who the client is: the founder of a skincare brand doing about $3 million a year, smart but allergic to jargon, reads everything on her phone. She'd describe what good looks like: one page, three headline numbers up top, a short "what this means" section, one clear recommendation. She'd flag what to avoid: no acronyms without translation, no speculating beyond the data. And she'd set the format: a plain email draft she can review in ten minutes.

That's not a prompt trick. That's a competent manager delegating. It also happens to be, word for word, an excellent prompt.

The briefing, written down

The draft that came back wasn't perfect. Sarah called it "an 80 percent draft from a bright junior" — which is exactly the point. Editing an 80 percent draft takes her twenty minutes. Writing from zero took two hours.

The delegation checklist

You don't need a formal framework yet (chapter two has one waiting). Before any task that matters, just answer the four questions you'd answer for a new hire:

• Who is this for? The audience decides vocabulary, length, and what to lead with.
• What does good look like? A target length, a structure, or a past example you liked.
• What should they avoid? The mistakes you'd normally catch on review — name them up front.
• What format, delivered how? Email, bullet list, table, script — whatever drops into your workflow.

Thirty seconds of answers. In practice, that's the difference between output you delete and output you edit.

Where the analogy breaks

A real new hire remembers on Tuesday what you taught them Monday. The AI doesn't. Every fresh chat starts from zero — same brilliance, same total amnesia about your business. That sounds like a flaw, and it partly is, but it has an upside: you can never over-explain, never sound condescending, and never catch it rolling its eyes at your fourth reminder about tone.

Why the amnesia happens — and what the AI actually walks in the door knowing — is where we go next.

Try it now

Pick one writing task you did by hand this week: a client email, a job posting, a policy note for staff. Say the briefing out loud, as if a new hire were sitting across the desk — who it's for, what good looks like, what to avoid, what format. Now type roughly what you just said, paste any material they'd need, and send it. Grade the result like a manager, not a judge: not "is this perfect?" but "is this a usable first draft?"