How To Make Every Conversation Interesting With A 'Can Opener'
How I productively derailed a nice and quiet executive dinner and took us to deep waters instead
In this issue:
A Boston executive dinner that veered into existential territory
Why the best conversations begin with the right “can-opener”
A tactical approach to asking better questions
May refer-a-thon: A signed copy of The Stoic Capitalist up for grabs
Why the weird email timing?
Each issue goes out at when one of my sons were born and made me whole.
This one comes at Lucas’o’clock - enjoy!
So I Chaired An Executive Dinner In Boston That Turned More Curious Than The Executives Expected
“Why are we doing any of this” might not be the most typical question to start an executive dinner with, but it’s now cemented at the top of my go-tos for kick-staring deep discussions.
Team Lewis has taken on the delightful habit of hosting ‘editorial dinners’, and due to an unexplained lapse in their judgment (or perhaps the unavailability of someone who actually knows how to toast instead of just drink) they had invited me to chair their Boston edition this week.
The Whisky Room at SAVR wasn’t ready for what was coming, and I am afraid neither were the executives whose expectations of a quiet dinner in polite company were promptly dashed by my ask to go after the ‘deep why’ well before the first appetizer had hit the table.
My ask wasn’t rhetorical, mind you.
The one thing I’ve learned from my 498 CEO interviews since early 2024 is that most executives cherish the opportunity to think deep thoughts in safe places. The problem is that that most of the places they encounter never ask them to go deeper than their latest quarter, and they rarely have the benefits of being in a friendly harbor.
In fact, study after study has shown how the CEO job is often one of the loneliest. Now I’m not here to seek sympathy for those at the top of the food chain, but my interviews fully validate anecdotally what others have found academically. The higher you get, the lonelier it becomes, and I’ve found my current little niche in the world by giving everyone from Warren Buffett to the startup founder down the street a safe space to be vulnerable in ways they can’t afford to be elsewhere.
And when the conversation really gets going, we rarely talk about the latest quarter’s figures. Instead, we talk about what really matters to those I am seated across.
Getting to that point, is a magic act I am doing my best to perfect with each conversation.
The Hunt For the Great Question
I’ve recently taken on the habit of visualizing the alternative universes each of my potential actions might take me to.
Whether its due to being subjected to too many Schrödinger’s cat memes or having actually quite liked Doctor Strange in the Multiverse of Madness remains uncertain, but for some reason I can’t shake the idea that while only one thing will happen, many things could have.
Often, the decisive factor between which of these world’s manifest is what we do.
I reflect on this after almost every conversation I have that is of any significance.
Maybe its my take on the spirit of the staircase on steroids, or something one my readers knows the right medication for, but in either case I’ve come to appreciate the thought exercise it puts me through.
Each conversation we have is ours to guide. If we care about the outputs of that conversation, it behooves us to also care about getting them. And yet, too often we let conversations happen to us, instead of being active drivers of them.
Don’t worry, I am not suggesting that you approach each conversation here onwards like an actuary, counting the probabilities and min-maxing your way to your preferred outcomes. In fact, I believe DSM-5 has a specific name for people who do.
But there is a specific concept I want to sell to you. It’s the same I used to kickstart the editorial dinner, and I perfect my craft with it in each of my CEO interviews.
I’ve come to call it the “can-opener.”
IT’s a question so great that the response isn’t “oh that’s a great question,” instead, its a moment of silence followed by a thoughtful monologue that can go on for minutes at a time if left uninterrupted.
The can-openers are the ‘great questions’ I am hunting for, and I keep each one I find stored in a Google Keep note part as a trophy and part as the basis for remixing the next iteration of it.
I’m sure you have come across your fair share of them too, and I invite you to start treating them like the treasures they are.
Getting A Great Monologue Started
My chosen can-opener for the executive dinner was the “deep why,” and it worked like a charm.
What followed was an hour-long detour into purpose, people, and what sits beneath the surface of strategy decks and boardroom bravado. And the more we asked why, the further we drifted from AI product launches and quarterly OKRs closer to opening ourselves up as humans to a group of strangers that may or may not ever meet again.
I’m sure the open bar Team Lewis covered before the dinner started had a role to play, but I’d like to give full credit to each of our conversation partners for engaging with the ‘why’ in exactly the way I had hoped.
With curiosity and a permission to admit that we might not know all the answers.
We all need more spaces where we can say "I don’t know, but I want to find out" as well as question our job title and all it stands.
And as friends and colleagues, we need to take responsibility over steering our discussions towards the universes where we all have more satisfying conversations.
Sometimes we need help to stay curious. Sometimes we need someone else to help release that great monologue we’ve been holding back.
And sometimes, its all as easy as staying curious about the “why” of it all.
Send this issue to a friend to let them know you’re ready for their monologue the next time you meet
A book to read
Magic Words by Jonah Berger
We spend most of our lives in conversation one way or another.
Talking, writing, emailing, posting, throwing words into the world and hoping they stick.
But what if certain words actually work better? What if some words take you closer to the alternative universe you wanted?
That’s what Jonah Berger explores in Magic Words. It’s a book backed by real research on how words influence perception, persuasion, and behavior, and I loved the read.
The book breaks down why some phrases unlock buy-in and others create resistance, why adding “because” to a sentence makes it more compelling, and why certain pronouns change how others perceive your power.
It’s the kind of book that doesn’t just make you a better communicator. It makes you more conscious of the subtle levers we all pull, and how to pull them deliberately.
Read it slowly. Then listen to yourself speak, you’ll hear the difference.
And here’s my 2023 Forbes piece on it.
A thing to do
Start a hunt for the Great Question
Great questions don’t actually get countered with a “great question.” A real can-opener that makes the other person pause, shift in their seat, and say, “...hmm” before they open up.
Start collecting those today.
Seriously.
Keep a running list in your notes app or a notebook. Every time someone drops a line that unlocks a deeper layer of the conversation, write it down.
Some that I have stolen and remixed from others:
“What are you pretending not to know at work?”
“What’s the belief that most limits you?”
“Why do you think we’re actually doing any of this?”
Use them. Test them. Remix and refine them like any other craft.
If you care about better conversations, you owe it to yourself (and them) to bring better tools to the table.
A thought to have
The question-statement ratio
Think of the last meeting, dinner, or debate you had. Now do a quick mental count: how many questions did you ask? How many statements did you make?
Most of us, especially those who have taught at any point of our lives, lean far too hard on statements. We speak to signal. We speak to prove. And in doing so, we often forget the power of listening
The question-statement ratio is a mental model I use to course-correct in real time. When the ratio tips too far toward declarative, I do my best to make myself recalibrate and to ask better questions, to listen more, to say less.
This isn’t about fake Socratic technique. It’s about presence. It's about curiosity that actually reaches somewhere unexpected.
Statements might show confidence, but questions invite transformation.
A product to love
Project Gutenberg
Whatever rabbit hole I’m chasing I usually end up in the quiet, miraculous archive that is Project Gutenberg.
It’s one of the internet’s purest gifts: no ads, no agendas, just tens of thousands of books preserved and digitized for anyone curious enough to wander through them.
Right now, one tab has me deep in The Apology of Socrates, the other is a Finnish anthology of pre-Christian gods I’m struggling my best at to translate, a personal attempt at recovering threads of cultural memory that never made it into the schoolbooks.
Project Gutenberg is where I go when I want to read something not because it’s trending, but because it’s buried. And sometimes that’s exactly the point.
Recent writings on Forbes and beyond
Latest: Your Brain Hates Your Cubicle—Here’s How to Thrive Anyway (Psychology Today)
Arvind Jain: The Humble Builder Behind Glean And The Future Of Agentic AI (Forbes)
The Outsider Advantage: How Naïveté Fuels Billion-Dollar Startups (Forbes)
Never Make a Bad Choice Again by Embracing Self-Nudging (Psychology Today)
The Psychology Of Better Choices: How Startups Are Rewiring Our Habits (Forbes)
Staying Curious Is the Most Dangerous Thing You Can Do (Psychology Today)
After Arkansas: The Future Of FEMA And U.S. Disaster Relief (Forbes)
Ryan Gellert on Building a Future Where Sustainability Is Not Optional (Forbes)
Why Struggling (the Right Way) Helps You Learn (Psychology Today)
Want to Make Better Decisions? Copy the Slime Mold (Psychology Today)
Your Brain Was Built to Forget—Make It Work For You (Psychology Today)
The Case For Terminal Optimism In An Unpredictable World (Forbes)
The AI Coordination Revolution You Haven’t Heard About Yet (Forbes)
Let’s meet up, I’m talking at
Glean:GO 2025, SF
AIAI Generative AI Summit New York
A wonderful set of classes on Persuasion and Leadership at Columbia and Harvard
I am currently conducting a study on range and how it impacts people’s career trajectories. Ten questions and a name will get you on the hall of fame as we pump up the n on the study. Link below - thanks for considering it!
You’ve reached the end - thanks for scrolling all the way down.
Curiosity is best when enjoyed in great company.
Refer this issue and grab a chance to get a signed copy of Robert’s book that I got after a conversation that taught me how to properly read memoirs.
If you end up getting a copy yourself, drop a line in the chat below - let’s exchange notes!
