The straight answer
Never open with “tell me about yourself”, or you’ll get the press release. Start with an object, then ask about one day instead of one era. Use 4 follow-ups: what did that feel like in your body, who else was in the room, what did you actually say, and (late, once they trust you) what do you wish you’d done instead. Then stop talking. Keep sessions to 90 minutes.
The worst question you can ask somebody about their own life is the one everybody opens with.
“So, tell me about yourself.”
Watch what happens. They’ll hand you the potted version they’ve given four hundred times, in the same order, with the same three anecdotes buffed to a shine. Born here, studied this, joined that, started the company in whatever year. Forty minutes of a press release delivered by a human being.
You’ve learned nothing, they’re bored, and you both quietly conclude that their life isn’t very interesting. It’s a lie you told each other by accident.
This is what I do for a living, so let me hand you the actual method. There are conversations you should be having with people while you still can. A parent. A founder about to retire. The person who built the thing you now run.
Start with an object
The potted version lives in the chronology. Step outside the chronology and it has nowhere to go.
Ask about a thing. What was on the walls. What the office smelled like. What they wore to the first meeting and why they picked it. What was in the car.
Objects work because nobody has rehearsed them. Ask a woman who built a company from her kitchen table what was actually on that table and you’ll get four minutes of unguarded, specific, gorgeous material, and somewhere in the middle of it she will accidentally tell you the truth about that year.
Ask about one day, not one era
“What were the early years like” produces summary. Summary is where stories go to die.
“Walk me through the day you nearly lost it” produces a scene. Where were you standing. What time was it. Who called. What did you say to them, in the actual words you used.
Every good book is made of days. Get days.
The four follow-ups that do all the work
“What did that feel like in your body?” Sounds like therapy, works like a crowbar. People remember physically long after they’ve sanded the emotional version into something presentable for dinner parties.
“Who else was in the room?” Puts other humans in the scene, which turns a statement into a story. It also reliably surfaces the person who mattered most and who they hadn’t thought to mention.
“What did you actually say?” Not what they decided. The words. Dialogue is the difference between a chapter somebody reads and a chapter somebody skims on the way to the next one.
“What do you wish you’d done instead?” Ask it late, once they trust you. The answer is almost always the real chapter.
Shut up
The single hardest skill and the one that separates a usable interview from a nice chat.
When somebody stops talking, count to five before you say anything. Most of what I’ve ever got that was worth printing arrived in second four. People fill silence, and what they fill it with is the thing they were deciding whether to say.
Nodding is allowed. Filling it for them is not. The urge to rescue somebody from a pause is the most expensive politeness there is and it has cost more good books than writer’s block ever has.
Practical things that matter more than they sound
Record everything, with permission, and say plainly it’s so you can listen properly instead of scribbling. Nobody has ever objected.
Get it transcribed. Read the transcript rather than relying on memory, because memory keeps the bits that moved you and loses the bits that will actually build the book.
Never correct their grammar while they’re talking, and never tidy their phrasing in the transcript. The odd construction is the voice. Somebody who says “and then the whole thing went sideways on us” has told you more about themselves than any properly built sentence could.
Keep sessions to ninety minutes. Past that people get tired and start performing again.
Ask the same question again six weeks later. You’ll get a different answer, and the second one is usually truer, because the first time they told you the version they’d built and the second time they’re telling you what they remember.
If you want somewhere to start, StoryCorps publishes its list of great questions for exactly this, free, and it’s better than most paid courses on the subject.
The one to save for last
When you’ve done a few of these and the person has stopped managing you, ask this.
“What’s the part of this you’ve never told anyone?”
Sometimes you get nothing. Often you get a long pause and then something that reorganises everything you thought the book was about.
Whatever comes back, it is theirs and not yours. Ask before it goes anywhere near a page, and take no for an answer gracefully. I’ve had extraordinary material handed to me and handed it straight back, and I have never once regretted it. Trust is the only thing that makes the next interview possible.
Go and do it
There is somebody in your life whose story is going to leave the building with them. A parent, a mentor, the person who started the company you now run.
You do not need a book deal to sit down with a recorder and ask them what was on the walls. You need ninety minutes and the discipline to stop talking.
Do it this year. That’s the whole advice, and it’s the only one on this site that costs nothing.
Your Next Fave Read
- How to Write About Real People in Your Book
- Is My Story Worth a Book? How to Know Before You Write One
- The Storykeeper Manifesto: Why Your Most Powerful Business Asset Hasn’t Been Written Yet
Ready to get your wisdom into the world, however you write it? Book a free validation call. I’ll figure out the right approach for your specific book and your actual goals, whether that’s coaching, ghostwriting, or the two of us writing it together. writewordmagic.com
