Walking 1:1s in person is one of my favorite forms of conversation. When I worked at One Medical, it was quite common to see heaps of people walking outside of our office to chat. During my last few months, we moved to a beautiful office right by The Embarcadero. Before that, we were right on Sutter street, surrounded by Blue Bottle coffee shops. One of my favorite ad hoc 1:1s was with Suneel—our head of mobile who joined through an acquisition. He always knew the right things to say to me when I needed guidance or a thought partner on anything I struggled with.

The funny thing about advice is the most important ones resonate with you much later than when the words were expressed. In this particular 1:1, I mentioned to Suneel I was a bit lost about what I wanted to do with my career.

"Have a lot of conversations,” he replied to me.

That’s it. That was the advice. At that moment, I was confused and felt what he said was so obvious. Later on, and repeatedly having conversations, I understood what he meant by that, and now I’ll share it with you. Later that summer, I took time off to return to a very hot New York and scheduled conversations with a mix of close friends, people I’m inspired by, and others I’m curious about. I queued up coffee conversations, breakfasts, and walks along the Highline. Ever since that 1:1 with Suneel, I make sure I am intentional about setting time to have conversations.

That’s it. That was the advice that was it. Talk to a lot of people? At the time, I thought I was doing that already. It wasn’t until later during a hot New York summer, I decided to be more intentional about it. I did a conversation tour to get inspiration in the city that inspires me the most. I reached out to people I really look up to or was curious about what they did. It was at this moment when I realized what Suneel meant. Conversations are about breaking bread, sharing experiences, and going beyond speaking to each other. It was an experience you take with you.

This isn’t networking. In fact, I do not like the term networking. Your networks are built on the great conversations that form life-lasting relationships. Let’s discuss the value of conversations, some of the elements that make great conversation, and some ideas on how you can set some up.

The value of conversations

Hopefully, I don't need to convince you of the value of conversations with your friends and loved ones, so we can move along to more of a passion and professional context. Do not conflate talking to people as a conversation. Some people are very transactional and self-serving. I have some thoughts on what makes talking conversational and great.

Great conversations are generative, spark serendipity

Conversations are not meetings. They do not need an agenda or a desired outcome (though they can). They can be generative and a way to explore. In my opinion, the best conversations are the ones you don’t know where they’ll go. They spark an idea or a serendipitous moment nobody planned. Have you ever left a conversation glowing and feeling energized about the exchange of energy between you and someone? That’s the goal.

Great conversations feel like mutual mentorship

The one thing people get mentorship very wrong is forcing it too much. Like any good relationship in your life, they happen organically. Great conversations feel like a mutual exchange of mentorship. Mentorship should never feel like speed dating and age doesn’t matter with mentorship. In fact, one of the most important mentors in my career now is a twenty-something-year-old! Great conversations feel like mentorship sessions where it doesn’t matter who is the mentor and who is the protégé¹.

Great conversations show new perspectives and directions

I try to avoid the echo chamber effect. For me, conversations are boring when you’re looking for agreement on everything or a confirmation bias. Great conversations aren’t necessarily easy conversations. Having a conversation that challenges your belief, asks you to consider other perspectives, and leaves you with empathy and new directions is what you should strive for.

New directions might be a new path. This week I had a conversation with a former coworker where we were discussing this. Early in my career, I basically knew the path of being an individual contributor and moving into a management path, but there is so much more than that. As I connected with interesting people, I learned more about different things people can do in their careers. If it wasn't for early conversations in my career, I would never think of management or investing as a path.

Great conversations are about listening and helping

Vulnerable conversations are powerful. I get disappointed when friends have conversations with me that sound like an Instagram post, where they are unwilling to share the reality and curate every word to make it everything sound okay. I know it takes trust to have these conversations. That said, the best chats I’ve had with friends or people in the industry are when you can bring your absolute worst and have a space to express yourself. For the quieter folks, you are some of the great conversationalists because of how great you are at listening—never forget that.

The elements of great conversation

It’s going to take time to figure out what types of venues and formats you like having conversations. What works for me will not work for you. For example, I do not like going to meetups because it’s exhausting.

David Hoang @davidhoang

Me five minutes into a tech meetup.

7:47 PM ∙ Feb 25, 2023

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This doesn’t mean it’s wrong. You might be an extrovert and get a lot of energy in groups vs. 1:1s as I do. Andrew Yeung is an incredible community builder at scale. He’s a great example that you can do a many-to-many conversation and I know for a fact people who attend his events get a ton of value. Consider the elements of what fosters great conversation for you as I share a few that are optimal for me.

Foster an intimate environment

Not every conversation needs to feel like an exclusive sit-down with Oprah (though it’d be dope). The environment varies based on your personality of you and the people you’re chatting with. It could be a walk in the park with awesome dogs, a quiet conversation at a cafe, or even on a hike.

Quality over quantity

There are some close people in my life with whom we’ve actually only had a handful of conversations, but they were as meaningful (sometimes more) as someone you’ve known for years. The quantity of time conversing with someone has nothing to do with how meaningful it is. I’ve been practicing the idea of having 15m phone calls with people who inspire me and in that short amount of time fill my energy well more than an hour conversation. In addition, some of my closest friends are people I talk to once every year or so. What are the energy gainers in a conversation for you? How can you maximize those attributes?

Synchronous

Text messages, voice memos, and other asynchronous methods great tools for communication, but don’t necessarily lead to great conversation. Don’t treat meaningful conversations like a task in your CRM or inbox.

Great relationships spark from conversations

It surprises a lot of people when I say I’m an introvert. “But you have such a great network!” people will say. Though I get their intention, it makes me cringe. I don’t consider myself a networker at all. I’ve just been around this industry for a long time and hold deep relationships with people—fostered over many incredible conversations.

Instead of messaging people with a calend.ly link and asking if they’re available in the next few days, let the relationship breathe. Treat conversations like you’re growing a garden instead of being a contestant on A Shot at Love with Tila Tequila.

Step away from the Twitter posts, and curated Instagram updates from friends that have no substance, and instead, go for a walk, grab a meal, send a thoughtful email, or pick up the phone to catch up.

I have a goal of calling 40 important people in my life this month and next month. So far, it’s been rejuvenating. Some ideas:

• Go on a conversation tour virtually or in person.

• Send an email update to your career advisors

• Write a blog post about what conversations you enjoy to send a beacon for those discussions

• Send a (non-creepy) DM to someone you’re inspired by to set up a conversation

Happy conversing.

Weekly recap

Silicon Valley Bank imploded this week and we’re still in the midst of it. I have a lot of thoughts on this, but not enough to write about it. I don't think in binaries and there are a lot of levels of challenges. Right now, my focus is on founders who are trying to figure out how to navigate it.

Tweet of the week

MacTheVC.eth @MacConwell

Hey Everyone. If you can, hug a founder today

6:55 PM ∙ Mar 10, 2023

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Hype links

• Devin Fountain just launched a newsletter. Subscribe to support him!

• Read.cv launched an iOS app called Posts I know, it’s always iOS-first). It’s a really nice place to post like the old Twitter days

• Unlocking AI and opportunity - Great interview with Chris Lattner

• The 3rd Linking Your Thinking conference is happening!