Freelancing Tips: The Art of the Interview

Over the years, I’ve interviewed Oscar winners, bestselling authors, billionaires, mad men (and geniuses). Here’s a tip sheet on what I’ve learned about the one-on-one.

Arrive 10 minutes early. Expect them to be 20 minutes late.

Dress well but not so well that they’ll remember.

The first 60 seconds tells you everything. Take note of eye contact, palm sweat, shoulder tics, head scratches, impulses to command the room.

Have a long list of prepared questions but try not to take it out of your pocket.

Make sure you know which questions your editors need you to ask. Ask them all.

Start gently. Open with a self-deprecating aside. Introduce yourself, your plan for your time together and then your recorder. People need to feel comfortable before opening up.

Running two recorders simultaneously is not a bad idea.

Get them in a car, a plane or on a walk. Conversation flows best when two people are side-by-side, eyes gazing forward.

It’s not about you. Until you sit down at the keyboard.

Don’t fill in their pauses. Let the awkwardness be a prompt for unexpected commentary.

Practice good manners with publicists, agents, managers and assistants but the interview must always be one-on-one.

Remember you’re the eyes and ears of the reader. Ask questions you would normally be afraid to ask.

Get them to talk about their childhood bedrooms.

Ask them about the best day of their lives.

If you’re bored, your editor and reader will be, too. Change the subject by saying “Let’s change the subject.”

Don’t be above stealing questions from Table Topics.

Reassure, comfort, affirm but make no explicit promises.

Sometimes it’s best to address the white elephant in the room right up front.

Then again, you might want to save the scariest question for last.

Leave the recorder running until you’re back in the car on the way home.

Photo of Jon Hamm by James Minchin III for Rolling Stone’s “Inside Mad Men” shoot.