The trick to writing about someone else? Let AI interview you first.

Today's Tip: Writing a recommendation letter that sounds like you

When someone asks you to write a recommendation letter, the hardest part isn't the writing… it's remembering the specifics. Most people try to write cold. They should let the AI interview them first.

Let me explain…

Reggie Broussard runs the Meals on Wheels route out of a church basement in Baton Rouge. He's 65, works three mornings a week, and knows every regular on his list by first name and standing coffee order.

Last week, a young volunteer named Marisela asked him to write a recommendation letter. She's applying to a Master of Social Work program. The deadline is September 12.

Reggie said yes without thinking. Of course he'd write it. She'd been showing up for two years… reliable, warm with the older folks, calm when a delivery went sideways. He knew she'd be good at the work.

Then he sat down at the kitchen table with a blank page. And nothing came.

He knew Marisela was excellent. He just couldn't remember specific stories. Not the way you need them for a letter that actually helps.

So he tried something different. He opened Claude on his laptop and asked it to interview him first… before writing a single sentence of the letter.

Here's the prompt he used.

Reggie spent about fifteen minutes on the interview. Claude asked him one question, he typed a few sentences back, then the next question came.

Somewhere around question two, he remembered the morning Mrs. Petrilli fell in her doorway. Marisela was the one who called it in, stayed on the porch, kept her calm until the ambulance came. He'd forgotten that story completely until the question pulled it out of him.

That one story ended up being the heart of the letter. Not the adjectives. The moment.

Now, I know what you're thinking. "If Claude writes the letter, isn't that cheating?"

Fair question. Claude isn't writing about Marisela… Reggie is. Claude is just asking Reggie what he already knows and organizing it into a shape that reads well — the specifics, the judgment, and the signature at the bottom are all his. That's not cheating any more than a secretary typing your dictation is.

The letter that lands in an admissions office needs to sound like you. So after Claude produces the draft, read it out loud. Any sentence that doesn't sound like something you'd actually say, rewrite it in your own words. The draft is a starting point, not a finished piece.

Reggie's letter is done. He read it out loud three times, rewrote about half of it, and sent it Tuesday morning. Total time: about forty minutes. He said the interview was the part that surprised him most… it felt more like talking to a friend than typing at a computer.

If someone has asked you to write a letter this fall — for a scholarship, a job, a school application, a co-op board — try this before you stare at the blank page. Let the AI ask you the questions first… then you write.

★ Quick Wins

Skill Builder: Get better answers by having the AI ask you the questions

Most people use AI backwards. They type a question and hope for a good answer. But the answer is only ever as good as the information the AI has to work with. And on your first try, it doesn't have much.

Here's the flip. Before you ask AI to write, plan, or advise on anything of substance, ask it what it would need to know from you first. This one move can turn a mediocre answer into a genuinely useful one, without adding much time.

It works because AI tools are trained to fill in gaps. If you don't give it context, it invents context. If you invite it to ask instead… you get context you actually agree with. The output that follows is built on your details, not on the tool's guesses about your life.

This works for almost any task where the details matter. Writing a letter. Planning a trip. Reviewing a contract. Preparing for a conversation. Anything where a generic answer would waste your time.

Try it on your next task. Watch how different the output looks when the AI has actually asked about your situation before answering.

The best prompts aren't clever. They're patient.