Tag: unfiltered

For years, I’ve given myself the lazy excuse. “I’m an introvert, so it’s okay if I’m bad at group conversations.” Empirically, the larger the group, the more I regress to being a wallflower. I was much more proficient at one-on-one and small group conversations than larger conversations. To be exact, to quote my friend, I was the “most David-like” in groups of 4 or less. I began to struggle in groups of 5-8. 9+ were the bane of my existence, at least on the front of contributing meaningfully to the conversation. And for the longest time, I never thought to look into that notion more, other than put myself in situations with larger groups and force myself to talk. I merely attributed my inadequacy to introversion and shyness.

For luck to stick

Yet, luck always has a way of finding its way to you. And if you’re curious, the best way to increase the surface area for luck to stick comes in two parts:

1. Say yes meaningfully to more things.
2. Have a bias to action.

What does saying yes meaningfully mean? This isn’t about saying yes to everyone and everything. This also isn’t about saying no to almost everything. I used to have a mantra, which I took from De Niro’s character in Ronin, “Whenever there is any doubt, there is no doubt.” Effectively, if I ever find myself in doubt, I shouldn’t hesitate to say no. But if you’re like me, I have the ability to second-guess everything. What can I say? I have a wild imagination. Eventually, that mantra led me to say no to almost everything in pre-2021. Subsequently, I cannot even imagine the number of opportunities I let slip through my fingers.

Saying yes meaningfully, on the other hand, meant my “yes” framework only needed to rely on a yes to at least one of two questions:

1. Does this make me jump out of my chair right now?
2. If I pursue this project, will I obtain skills, knowledge and relationships that will transcend the outcome of the project itself?

On the other hand, having a bias to action merely means to follow through with whatever you say you will do. Actions should always follow your words. If you say it, mean it.

Responsibility and accountability

A few months ago, a few of yes’s started to snowball. I began hosting fireside chats and panels, with an audience many times larger than the upper limit of my extroversion.

Unlike when I’m interviewing people for this blog or for a small podcast project I’m doing on the side with a friend, fireside chats are live by design. And because of that fact, backspace is not my friend.

Yet, despite it all, I didn’t succumb to the pressures of “extroversion”. Paired with a comparatively lower level of apprehension, I was and am more often looking forward to rising to the occasion in these conversations than in any other large group conversations. One might argue fireside chats and panel discussions are still small group conversations. It is… until you try to include audience participation during these conversations.

But why? Why did it feel more natural to host these fireside chats, panels, and group social experiments yet still struggle in ordinary group conversations?

I thrive on responsibility. The greater my sense of responsibility, the better I do in a conversation. Often times, the roles of each participant in a conversation aren’t clear. Who’s asking the questions? Who’s moderating the conversation? Should there even be someone leading the conversation? If things turn awkward, is it any one person’s fault?

At large, we also see this in group conversations – online and offline. On average, the larger the group, the less each individual feels accountable to contribute meaningfully to the group.

In 1:1 conversations, the responsibility for a great conversation is split 50-50. There’s nowhere to hide. In 3-person groups, it’s 33-33-33. In 4, it’s 25-25-25-25. And so on. At some point, often starting around the 4-person mark, people start feeling that the conversation can go on with or without them. In these fireside chats, it was very clear that it was host and guest’s responsibility for a great conversation. So despite boasting a larger headcount, the responsibility was largely split 50-50.

The lessons

While my goal is to be competitive in the top 0.1% of hosts, it’d be crass to say I started with any level of proficiency. Merely a passion. A passion to learn and help guests be their best selves. And when both guests and the audience walk away from the conversation, both will have felt that was an hour well-spent. As the theme of this blog is building in public, I’d love to share the start of this journey with you.

As such, here are a few lessons I’ve internalized so far:

1. Do your homework. My goal is always to know my guest(s) better than they know themselves at that point in time – specifically, in my rabbit hole research, finding things that warrant the “How did you know that” response from my guest. I start this process 4 weeks in advance. On average, I spend about 5-10 hours of research per guest, covering:
   • Socials,
   • Content they’ve created (if any),
   • PR/media articles,
   • Podcasts/interviews, and
   • Cross-referencing with mutual friends.
     Most of the above I find across 7-10 pages of Google search results.
     
2. Prep for more questions than you need. Usually for every half hour, you need 2-3 good questions, but always prepare 6-7 questions for every half hour as backup.
   
3. Some guests prefer having the questions beforehand to prepare; some don’t. I always ask when I invite them and respond accordingly. If they want to see the questions, I send that 1-2 weeks before the date of via email and updating the calendar invite with those questions.
   
4. Before every interview, in lieu of the pre-chat, I ask two questions. The goal is for your interview to just be another fireside chat, but that it’ll be THE fireside chat.
   1. Fast forward 2-3 years from now, what would make our fireside chat one of the most, if not the most, memorable fireside chat you would have done up to that point? I don’t need an answer immediately, and you can also tell me right before our conversation next week, but would love to use that as a north star for our talk.
   2. If there are any, what do you not want to talk about? Or are sick of talking about?
      
5. You’re running a two-sided marketplace. You want it to be THE fireside chat for both your guest AND your audience.
   
6. If, for some reason, I can’t find any good stories or anecdotes that need more context, I ask the guest a third question. Do you have one or two stories that when you told them privately or publicly earned you a standing ovation? Subsequently, rather than the full story, I ask for just a small teaser phrase that would help me transition the conversation into it. And well, I like to be surprised too.
   
7. If, for some reason, I can’t think of any specific/good questions, I ask the guest in the “pre-chat”:
   • What’s a question you wish I asked you that’s not in the itinerary? or,
   • What’s a question you wish you were asked, but never asked in previous interviews?
     
8. Make the conversation personal and relatable. Be sure to mix in both advice and story anecdotes. Despite all my fireside chats so far circle around a highly technical subject, what provides color is how much the guest is also a human with a life outside of work. Anecdotally, the more relatable a conversation is for the audience, the more likely they are to:
   1. Internalize the advice, or at least consider it, and
   2. Reach out and connect with the guest.
      
9. Depth matters more than breadth. It’s better to ask follow-up questions than to hit every question on your agenda. When sharing my questions with guests, I often tell them that “We’ll get to one, two, or some of the questions below, but I imagine we’ll run out of time before we run out of topics.” Anyone can replicate the same superficial questions as you ask. And if you only stick to the initial prompts, your interview will be like 95% of other interviews your guests would have been on. For your audience, while the strategic context is nice, the best takeaways are tactical – most of which are uncovered by follow-up questions.
   
10. Know your audience. In order for the advice and anecdotes to be useful and/or entertaining to them, you have to tailor your jokes, stories, and lessons to what would resonate with them the most. You need to find language-audience fit. Equally so, I found it extremely useful to also share the rough audience demographic with the guest beforehand.
    
11. Guests who bring their A-game are more important than guests who are just A-listers. While not mutually exclusive, there are too many potential guests out there that won’t take your interview seriously. Either via a lack of prep or treating it as a schedule write-off. It’ll be temporally relevant, but easily forgettable. And when that’s the case, neither the guest nor the audience takes much away from the conversation. Subsequently, it ends up being a waste of time for everything. When I started off, I only invited people that I knew reasonably well.

In closing

In all fairness, this essay could have been two separate pieces. But on a Friday morning watching the sun rise above the horizon with a cup of hot Pu’er tea next to me, it just felt right to share both my takeaways hosting conversations and the backstory that led me to be in that situation. Cheers. And I hope my takeaways supercharge you as much as they’ve supercharged me.

Photo by felipepelaquim on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

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