4 Things Tim Ferriss’ Interview Style Taught Me About Building Meaningful Relationships

1. Do Your Homework

• Takeaway: “Before I even invite someone, [I’m] looking at long-form video and audio to the extent possible…I’m looking for any odd hobbies or comments that weren’t fleshed out…It will prove to the interviewee that I have actually looked at the details and done my homework, which is really important for a lot of interviewees. Because if you don’t prove that early, they’re going to go on autopilot and they’re gone."

• Tip: If you have a planned meetup with someone new—like a job interview, a networking intro, etc.—you should always do your research on them. Take a look at their LinkedIn, find out what they like, speculate on their goals, and anticipate how you can be helpful. It helps direct the conversation and shows that you are interested in them. If you show up unprepared, expect awkward gaps in an unmemorable conversation.

2. Talk About Topics that are Being Neglected

• Takeaway: “I will try to identify what has been neglected, what has not been mentioned, and that can lead to some interesting places. Not always comfortable places"

• Tip: Even when we research someone, we still are only seeing part of the picture. I like to think there are multiple sides to everyone (like Everything, Everywhere, All at Once). Be curious and ask questions that lead to topics they may not get to talk about often. It’s the difference between asking “what are your strengths?” and “if your best friend was your job reference, what would they say about you?”

3. Understand Their Motivations

• Takeaway: “Then I ask them, and people comment on this because almost no one asks this, ‘What would make this a home run for you? Looking back after it’s published, say two months after it’s published, what would make this one of your favorite interviews or something that you would point people to?’"

• Tip: The quicker you understand someone's ambitions and goals, the quicker you can speak in terms of their wants and (most importantly) demonstrate how you can help them achieve those wants. This puts you in a very valuable place by establishing the grounds for a mutually beneficial relationship. Now you evoke a sense of reciprocity once you help them.

4. Open Up so They Feel Comfortable Doing the Same

• Takeaway: “If I want to try to unbox something that hasn’t been explored before, there’s probably a good reason it hasn’t been explored. So, I will find something in that same category. Could be relationships, could be a business failure. I will volunteer that information from my side first just to provide some transparency."

• Tip: No discussion should silo either person into “the question asker” and “the responder.” Conversations go two ways, especially when they’re meaningful. Mention upfront how a question relates back to you (i.e. if you answered the question, what you would say). This sets the stage for earning reciprocity, getting the person to be more comfortable answering the question, and feeling more connected to you after knowing your perspective.

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What I am committing to this week for both networking and building relationships (time commitment ~2 hours):

• 🌆 Making new connections at Andrew Yeung’s Rooftop Tech Mixer (~1 hour)

• 🧐 Incorporating Tim Ferriss’ interview prep techniques as I prepare to interview the founder of a DEI executive search firm for the buildbetter newsletter (~30 minutes)

• 🎙 Sharing this interview podcast on how Khan Academy was founded with three connections (~10 minutes)

• 🤔 Reflecting on my week this Friday: Am I putting in the work in advance to make conversations meaningful or am I jumping in without any prep (~20 minutes)

What are you committing to this week? Reply to this email!