Write Down Shitty Questions. (20 minutes.)
First, write down every possible question you could ever think to ask your mom or dad. (Let’s start with dad.) What's his favorite color, sport, gardening tool, Mexican restaurant? Have him describe the moment he arrived at college, hit a home-run, lost his virginity. Fill three notebook pages worth of shitty questions. Don't think about it, just keep the pen moving.
When you finish, circle the questions that most pique your curiosity. I've included a few sample questions at the bottom of this post to jump-start your imagination.
Call Your Mom or Dad
Tell them you want to interview them. Say that the interview will last somewhere between 20-40 minutes. (It can always go long, but this won’t feel too intimidating.)
Offer to send a few question prior.
Stories make for great audio. So if they can answer the questions with stories, ask them to think of a few bangers before the interview.
Start with A Positive Topic.
I like to dive into interviews by asking my guest to tell a story about a specific positive moment in their life, or a subject they know a great deal about. When they recount the story, it puts a smile on their face and allows me to take the conversation into deeper waters. The purpose of the first question is to get your dad talking, so ask about a subject that makes him comfortable. If your dad loves to fish, ask him to tell you the story of the biggest salmon he ever caught.
Asking a heavy question early on can come across as confrontational, and cause your mom or dad to get defensive. Maybe don't ask heavy questions at all. Your interview doesn't need to be a therapy session. Some of the best podcasts I've ever recorded have been with guests who told a few good stories, then walked away. Stories make for great audio, and it's essential that the beginning of the interview puts your dad at ease.
You never want an interview to feel like an interrogation, so if things get uncomfortable or you feel the energy dip, have an array of topics written down that you can pivot to at any time.
Followup Questions
The followup question is just as important as the initial. Often it can be as simple as asking, "What was that like?" or "What do you make of that?" One of my personal favorites is, "At that moment, what was the conversation like inside your head?" (I stole that from Alex Bloomberg.)
A question like this will get your dad to talk about his decision-making process.
Keep in mind that your Dad's life, like everyone’s life, is a series of choices, and if you can get him to expound on how he navigated forks in the road, it will reveal deeper truths. Also, and this is no small thing, you'll be able to listen back to his voice long after he's gone as you traverse the difficulties you have yet to face.
Don't Interrupt
People interrupt each other constantly. And often, when the other person is speaking, we are miles away, grasping for the next awesome thing to say, hoping to impress them or ourselves—or someone. Don't do this. When your dad is speaking, shut up. Pay attention. And then when you ask him a question, base it upon what you’ve just heard in order to advance the conversation, rather than show him how smart or funny or wise you are.
Have you ever tried to give a speech to an empty room? It's nearly impossible. When we speak, we want to know that someone is listening. In daily conversation, we show people that we're listening by saying things like, "wow, uh-huh, cool."
Don't do this.
If your dad is telling a story about the time he was deployed in Vietnam, taking enemy fire, and he looked up at the smoky sky and saw a cloud in the shape of a ballarina, and that was the moment he realized that he wanted to be a dancer, don't fuck up his story with, "uh-huh's." During a Zoom interview, look at your dad's face on the computer screen, smile, nod, and keep your mouth zipped.
Prep Your Tech
You can conduct the most fabulous interview in the multiverse, but if there's a lawnmower in the background, it's worthless.
The most minimal way to record an in-person interview is to use your cell phones’ voice recorder app.
The quality of your audio is directly proportional to the proximity of your device to your guests’ face.
Put your cell phone on the table just in front of your dad or mom. Know that your voice will sound distant this way. I recommend investing in an external mic that connects to your phone, but cell phones are fine too. (Keep it on Airplane mode.) Here’s a list of the best for 2023.
Alternatively, you can get a whole podcast setup, but this might be superfluous if you’re just planning to do one or two interviews.
For remote interviews, ask your mom or dad to find a quiet place with fast internet. It's OK if she uses the built-in computer mic, but better if you have an external mic, or Apple earbuds. If you're new to Zoom, record a test call with a friend so you can focus on the interview when it's go-time. Make sure you're in a room with light on your face, so you don't look like an extra from World War Z. Your computer should be about eye level, so if it's too low, prop it up on books.
On your Zoom call, have your questions written down next to you. Keep your questions on one page, so you're not flipping back and forth between pages. Oh, and when it's time to go, remember to press the big red button.
Sample Questions
Below are a few sample questions, to get you started. The rest is about following your own curiosity. I stole some of them from Tim Ferriss and the rest from my dad.
Tell me about how you fell in love with ____ (fishing, writing, cave diving.)
If you could give your 30-year-old self one piece of advice, what would you say?
What is the stupidest thing you've done for money?
What skill are you working to improve most right now?
What is the best lesson your father ever taught you?
What gets you out of bed in the morning?
What were you good at from an early age?
What did your childhood house look like?
What sports and hobbies were you into as a kid?
Was there a book that impacted you when you were young?
Who was your best friend growing up?
What would you do together?
If you would change one thing about the way you were raised, what would it be?
If you could wake up having gained one quality or ability, what would it be?
What would you tell someone to consider before they embark on an intimate relationship with someone?
What is the best part of your day, and why?
What causes you to be frustrated or angry, and why?
What makes you happy and why?
What makes you worry or feel fear and why?
Is there anything that you have a hard time forgiving yourself for, and why?
What are some of the things you're most proud off having done in your own life?
How would you like to be remembered?