713 episódios
713: Ken Chenault - Leadership Lessons from 17 Years as American Express CEO: How to Earn the Top Job, Hire Great Leaders, Build Culture, Challenge the Status Quo, and Lead with Character
02/11/2026 | 53minThe Learning Leader Show with Ryan Hawk
www.LearningLeader.com
New Book - The Price of Becoming
www.LearningLeader.com/Becoming
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This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver.
My Guest: Ken Chenault was chairman and CEO of American Express for 17 years, and Warren Buffett called him "the gold standard for corporate leadership." Today he's chairman of General Catalyst. His new memoir is Equal to the Task.
Key Learnings
"The only thing that you can control is your performance, so focus on your performance." His father's answer whenever Ken complained about a barrier. Ken says what makes it empowering rather than harsh is that it's both accountability and control at the same time.
"Ken, never forget that you are equal to the task." First day of kindergarten, Ken froze, started crying, and ran out of the room to hide under a bench. His father found him, pulled him out, sat him on his lap, put a hand on his shoulder, and said it. At five, Ken had no idea what the words meant. They became a measuring stick anyway.
What his father actually meant took decades to understand. Equal to the task is a challenge, not a reassurance. You still have to work for it.
"If you wish to be a king, you need to have followers. A king looks after his people." Ken's teacher in grade school, Mrs. Lacraw, called him down and told him that isn't what kings do. It wasn't enough to protect the hill. He had to protect people.
That became his North Star: judge a leader on the quality of their followership. Ken is emphatic that he's all about outcomes and driving results. The question is how those results were achieved and whether they'll endure.
The Followership Tree. Who are the best-performing people who came out from under this leader? Who do other people look up to? Who delivers on an ongoing basis? Coaches have coaching trees. Ken looks for a followership tree. Does this person train, develop, and attract the best people to work for them?
Trust is the core requirement, and everything flows from it. Intelligence and drive are givens on Ken's list. Trustworthiness is the thing that has to be there first.
Then: is this person willing to go against the status quo? It's the attribute that surprises people most when he names it, because what he's really screening for is courage.
So he asks directly. "Take me through when you had to go against the existing product set, the existing strategy. How did you do it? How did you go about it? Why did you do it?"
Decisiveness and caring is not a contradiction. The best leaders connect with the hearts and minds of people. Being caring doesn't mean you're afraid of the hard call, it means you're more effective when you make it.
"You could not imagine Amex without membership rewards." Membership Rewards was built in stealth mode. At the time, the culture at American Express held that rewarding card members for using the product was a form of discounting that damaged the brand's prestige. Ken disagreed, assembled a team across the company, and deliberately kept it quiet for about four months because he was afraid the traditionalists would kill it. He describes it as feeling like a startup. It launched in the early nineties and became one of the foundations of the company.
Take the assignment nobody wants. Ken decided American Express needed to re-engineer, meaning changing its processes and its structure. Most people avoid those projects because they're high risk and they can end a career. He took it because the company needed it done.
He never set out to be CEO. His objective walking in was to stay a few years and learn. He thinks making the top job your goal is dangerous: you start optimizing for what's best for you rather than the company, you stop taking the risks worth taking, and you can freeze.
The marker that mattered wasn't promotion. It was someone saying, "Ken, you can make that decision. Ken, you can handle that." The hardest thing to delegate is judgment. The way he earned it was by doing the assignment well and then working out its broader implications for the company.
"The role of a leader is to define reality and give hope." From a biography of Napoleon. Ken thinks about it every day in regards to leadership.
Defining reality is what earns you credibility. It doesn't mean having all the answers. It means being present, aware, and engaged, and doing real diligence with people inside and outside the company to find out what's actually happening.
But reality alone isn't leadership. Consultants can define reality. The second half is the specific, tangible reasons to be hopeful: a strategy, a product, something concrete. Sometimes the probability is five or ten percent, and the job is explaining why it's still worth the risk.
Simplify the mission. Simplicity doesn't make it easier; it gives you focus.
The three operating principles, written on a napkin at lunch. Provide superior value to the customers and clients we serve, do it in a way that achieves best-in-class economics, and make sure everything we do supports and enhances our brand. He went straight upstairs to Harvey, the CEO, and said these should decide which businesses the company is in. They took the board through it. Ken works from principles rather than a rule book.
"You should never make withdrawals in the brand bank. Only deposits." From Shelly Lazarus, then CEO of Ogilvy & Mather, and it shaped the third principle. Ken's extension: you have a brand, I have a brand, and the question is whether you'll knowingly do things that work against what you actually stand for.
Profit and purpose shouldn't be in conflict. Ken's first principle at General Catalyst: business exists because society allows it to exist; therefore business has a responsibility. Purpose is a real advantage in building something enduring, and you won't be around to make that purpose mean anything unless you're profitable and growing.
He wrote to four consulting firms admitting he didn't know much about business. Three almost certainly threw the letter away. Bill Bain happened to have just decided to hire two or three lawyers and two or three medical school graduates, looking for one thing: intellectual horsepower and drive. Bain himself hadn't gone to business school. Ken calls it a needle in a haystack and says that without it he doesn't think he would have had a business career at all.
Vernon Jordan's note. The day the board voted Ken in as CEO, Jordan folded a note and passed it down the table. It said the day was momentous, that he was proud, that their ancestors would be proud, and that many people had struggled so Ken could have this opportunity. Then, in classic Vernon: "If I were in church, I would say hallelujah, but the people in this boardroom would think I was crazy." Ken watched it pass through three or four pairs of hands, and nobody opened it. When it reached him, Jordan winked. Jordan believed strongly that nobody gets there entirely on their own, helped even by people they never see.
He was born three years before Brown v. Board of Education. His read on that: if he'd been born twenty years earlier, he would not have become CEO, and it wouldn't have mattered how good he was. Which is why the people, Black and white, who were in that struggle mean so much to him.
Feedback from Arthur Ashe. Ken was 35, told a business magazine, "I believe I can learn anything," and Ashe phoned him to say it sounded arrogant and that people would be looking for any reason to discount him. Ashe called it an unforced error. Ken's first reaction was to push back. Then he decided Ashe was right, and what he took from it wasn't to stay quiet but to operate with a higher level of intentionality. He would still challenge something or someone when it needed challenging. He just couldn't be careless.
Celebrate differences, and still hold the values that aren't negotiable. Ken loves team sports partly because you can't program them. You get thrown in with people whose background and beliefs are nothing like yours, and when alignment happens anyway, it's genuinely rare.
Warren Buffett's line about your most important decision being who your partner is. Ken and Kathy have been together 49 years. He describes her as down to earth, willing to speak her mind, with uncanny intuition about people. Someone once told him you have to feel it in the fingers, and he says Kathy feels it in the fingers. His four requirements for lasting that long: deep love, consistent communication, real trust, and patience, which took him several years to learn.
Ken's champagne moment a year from now: people talking about character and values. He didn't want to write a business book. His concern is that we're over-indexing on intelligence and success as a society, and he's careful to say he believes in both, but not at the expense of character. If he can get people talking about living a life with purpose, that's the celebration.
Action
Write your operating principles down on one page. Can you get them small enough to fit on a napkin, and would your team recognize them as the ones you actually use?
If you enjoyed this conversation, please check out Episode #662 with Nick Thompson: Move at an Uncomfortable Pace.
Episode Chapters
01:17 The Only Thing You Can Control
02:52 Where "Equal to the Task" Came From
05:03 If You Want to Be a King
08:35 What He Looks For in a Leader
11:31 Building Membership Rewards in Secret
14:20 Profit and Purpose
16:47 The Letter That Started His Career
21:40 How Bain Took On McKinsey
24:04 Define Reality and Give Hope
27:04 How He Earned the CEO Job
32:09 Vernon Jordan's Note
34:43 Business as the Next Civil Rights Frontier
37:12 The Call From Arthur Ashe
40:25 You Can't Program a Locker Room
42:44 Three Principles on a Napkin
47:20 49 Years With Kathy
48:54 The Champagne Question
51:15 EOPC712: Matt Abrahams - How to Become a Better Communicator: Speaking With Confidence, Structuring Your Message, and Thinking Fast on Your Feet
25/10/2026 | 54minThe Learning Leader Show with Ryan Hawk
www.LearningLeader.com
New Book - The Price of Becoming
Connect on social: Twitter - @RyanHawk12
Instagram - @RyanHawk12
My Guest - Matt Abrahams is one of the world's foremost experts on communication. He's a lecturer in strategic communication at Stanford's Graduate School of Business and bestselling author of Think Faster, Talk Smarter. His focus is the hardest kind of communication: not the rehearsed speech, but knowing what to say when you're put on the spot: in the interview, the Q&A, the hallway, the toast.
This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver.
What you'll learn in this episode:
Matt's father was quiet but not shy. A lawyer, skipped a couple of grades so he was always younger than his colleagues, a man of few words and very detailed ones. Matt says what he most wants to live up to isn't the intelligence, it's that his father believed in being truthful and trustworthy.
His parents asked two different questions about communication, and he's still answering both. His mother taught elementary school and wanted to know how you make it engaging and how you hold attention. His father wanted to know how you organize it and make it structured and understandable. They debated it constantly at home. Attention and structure are still the two halves of everything Matt teaches.
When You're Interviewing Someone
The best interview question he was ever asked: "If you were an onion and I peeled back the first several layers, what would I find?" It was the CEO's opening line, before anything else. Matt's answer: "Onions make me cry." He got the job. When he asked about the question months later, the CEO said he uses it to knock people slightly off center, and what he remembered was that Matt committed to an answer and connected it to something bigger.
That's the whole move when you're put on the spot. Commit, then connect what you said to the larger picture. The content matters less than refusing to hedge.
Warm call, don't cold call. Matt doesn't cold call at Stanford and won't do it in an interview either. He tells candidates up front: I'm going to ask you things that are difficult, the goal isn't a right answer; the goal is seeing how you process and how we'd collaborate. Then he asks the hard question. Blindsiding someone tells you how they handle being blindsided, which is not the job.
Watch how they treat everyone who isn't you. Matt always asked whoever greeted the candidate how the interaction went, because plenty of people are rude to the front desk and flawless with the hiring manager.
Teach candidates how to answer. Matt tells people at the top: answer the question, give me an example so I understand what it means, then connect it to what that would look like if you worked here. Otherwise people ramble, and you're left wondering why they told you any of it. He says it changed his interviews completely.
When You're Giving a Talk
Intention, attention, then relevance. How are you showing up, what energy and emotion are you bringing, and what will grab the room? Then, fast, why this is worth their time. "Attention is a gift people give you. If they don't see a return on that, they're gonna check out."
Start like an action movie. How does an action movie start? With action. Not "hi, my name is, and today I'm going to talk about," which is also just reading your first slide out loud. Tell a story, ask a question, take a poll, give a startling statistic, and introduce yourself afterward if at all.
The first thing Matt's students hear him say each term: "Communication is critical to your success in business and in your personal life."
If you're a nervous speaker, NEVER pre-apologize. Saying you're a nervous speaker feels like buying empathy. What it actually does is prime the room to notice every piece of evidence that confirms it, and it pulls attention off what you're saying. Just start.
How you end matters almost more than how you start. We remember what we hear last, and it recolors everything before it. A wonderful vacation gets remembered a little less wonderfully if the flight home is delayed and the luggage is lost.
But the second you signal you're ending, people leave. Say "in conclusion" on a video call and, like Pavlov's dogs, they're opening their calendar. You don't have much runway, so know exactly what the last thing is.
Know, feel, do. Every communication should have a goal in three parts: what you want people to know, how you want them to feel, what you want them to do. Build everything on it, then close by restating it in your own words. It summarizes and gives a sense of completion at the same time.
Don't memorize. It's connection, not perfection. A memorized script means part of your brain is permanently comparing what you're saying to what you meant to say, like having too many apps open and each one running slower. That's the bandwidth you need for the actual goal. There's also research showing the more you memorize, the more you forget.
Write it out, then distill it to a structure. Writing the whole thing out is fine, especially if you're new to the topic or not a native speaker. Then reduce it to a roadmap. Problem, solution, benefit is one, and most people already know it because television ads are built that way. Practice from the structure, not the script.
What, so what, now what. The what is the information. The so what is why it matters to this particular person. The now what is what happens next. It fits an update, a teaching moment, an email, where the subject line becomes the now what and the body carries the rest.
Structure isn't decoration; it's retention. Cognitive neuroscientists have found structured information is remembered at least 40 percent better. The goal is fidelity, and a leader's job isn't just to communicate but to deliver a message other people can repeat accurately.
If a number or a quote has to be exact, read it and say you're reading it. "I wanna make sure I get this right." That's cleaner than memorizing, which just makes you more nervous and builds distance.
Slides should simplify, amplify, or clarify. If a slide doesn't do one of those three for your audience, it doesn't need to exist. TED proved you can give a powerful talk with none.
A slide full of words forces people to multitask. Spoken and written language run through the same part of the brain, so text on screen competes with your voice. Images and charts run through visual processing instead, and the two together make the point more memorable. Slides are for your audience, not a teleprompter for you.
Humor is black belt level engagement. It's the riskiest tool there is. Never run a joke for the first time in a high-stakes room, and listen to what happens when you test it. Questions, stories, and asking people to do something physical are all safer ways to get the same engagement. And the rule that keeps you out of trouble: humor about yourself, not about others.
Never lose your tour group. Matt was a campus tour guide in college, and the single most important thing they trained him on wasn't storytelling or vocal variety. It was not losing anybody. The same applies to an audience: set expectations so they know where they're going, connect where you've been to where you're headed instead of jumping between points, and keep them motivated to move. And notice where every campus tour ends. The bookstore. People need something to take away.
When You're Making Small Talk
Small talk leads to big things. Think about your actual friends, not your social media ones. At least one of them exists because of small talk.
The goal is to be interested, not interesting. From Rachel Greenwald, who studies how people form relationships. Which means asking questions and then leaving room for the answer.
Three words make you good at it: "Tell me more." Ask a question, listen, then ask for more, and mean it.
Exit with a white flag. Not surrender. In auto racing, the white flag goes out on the final lap. Most people end small talk by reaching for biology, saying they need the bathroom or another drink, which backfires the moment the other person needs the same thing. Instead: "This has been great. In a minute I'm going to go talk to someone over there, but before I do, I want to hear more about..." They know it's ending, you get one more real question, and you both walk away clean.
When You're Trying to Get Better
A few filler words now make you sound human. Some disfluency is normal and natural, and in a world where anything can be polished by AI, a few verbal foibles are evidence a real person is talking. The problem is only volume.
The breathing trick that kills the filler words. Try saying "um" while inhaling. You can't. Speaking is an exit-only event. The filler words that stand out are the ones sitting in silence between sentences, so if you train yourself to land every phrase out of breath, you're forced to inhale before the next one, and nothing can fit in that gap except a pause. To practice, read a list out loud once or twice a day, your calendar works, and run out of air at the end of every item.
Watch and listen to yourself, and read out loud. Reviewing your own recordings is awful, which Matt compares to the dentist: nobody enjoys it, everybody's glad they went. Reading aloud builds vocal stamina the same way a treadmill builds a marathon. Nobody wakes up and runs 26 miles untrained, and most leaders aren't used to speaking for long stretches either.
Costco credibility beats college and career credibility. Your background and your resume are real credibility, and they matter. But Costco hands out free samples because an experience of the thing beats a description of it. Most people over-index on listing credentials. Tell stories, give examples, use testimonials, and let people taste it.
There is no right way to communicate, only better and worse ways. Matt resists the word expert. Early in his teaching, he'd gesture and watch an entire class decide that was the correct way to move your hands. Saying it out loud takes pressure off the room and off him.
Matt's champagne moment a year from now: people being more confident, clear, and compelling in how they communicate. He thinks the world needs to hear everyone's voice and that clarity is what makes that possible. He knows it's working when an email arrives from a town he has to look up on Google.
Daily reflection, one minute, for 16 years. Every night before bed, Matt writes down one thing that went well in his communication and one thing that didn't. Every Sunday he spends about five minutes reviewing the week and picks one thing to work on.
Action
Take the next talk or meeting you're running. What are the first fifteen words out of your mouth, and would they work as the opening shot of a movie?
Who did you talk to today where you were trying to be interesting instead of interested? What would have happened if you'd said "tell me more" one more time?
If you enjoyed this episode with Matt Abrahams, check out episode #709 with Vanessa Van Edwards: How to Connect With Anyone & Make Every Interaction Count
Podcast Chapters
00:00 Apply for the Learning Leader Circle
01:36 Meet Matt Abrahams
02:56 What He Carries From His Father
04:53 "If You Were an Onion..."
07:16 Warm Call, Don't Cold Call
08:52 How He Got Better at Hiring
13:35 Going From Silence to Brilliance
16:20 Know, Feel, Do
19:04 Never Tell Them You're Nervous
21:34 Why Memorizing Backfires
23:50 Simplify, Amplify, or Clarify
25:34 Start Like an Action Movie
27:03 The Question That Moves a Room
29:56 Never Lose Your Tour Group
32:21 Humor Is Black Belt Engagement
33:44 Three Words: "Tell Me More"
36:51 One Minute Every Night for 16 Years
40:06 What, So What, Now What
42:42 Breathing Out Your Filler Words
46:00 Read Out Loud for Vocal Stamina
47:44 Costco Credibility
49:43 The Champagne Question
52:25 EOPC711: Seth Godin - Creating Tension, Solving Problems, the Savannah Bananas, Leading Without Authority, Using AI, Hidden Entanglements, and Getting Unstuck (The Knot)
18/10/2026 | 47minThe Learning Leader Show with Ryan Hawk
www.LearningLeader.com
Connect on socials: Twitter/X - https://x.com/RyanHawk12
Instagram - @RyanHawk12
LinkedIn - @RyanHawk
My new book, The Price of Becoming, is a USA Today, LA Times, Success Magazine, and Publishers Weekly Best-Seller! I think you'll find it useful.
This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver.
My Guest: Seth Godin is the author of more than 20 bestselling books, including Purple Cow, The Dip, and This Is Marketing. He has written a blog post every day for more than two decades, and it remains one of the most widely read blogs in the world. Before the books, Seth founded Yoyodyne, one of the first internet marketing companies, and sold it to Yahoo in 1998. He later created the altMBA. His new book is The Knot: Problems Can Be Solved.
Key Learnings
Being early is a courtesy, not a personality trait. "I don't understand why someone would willfully waste somebody else's time."
The knot is the point. You can't have a pretzel without the knot, and if you try to undo it you end up with crumbs. Real life isn't like that. Our knots can actually be untied.
Teach so that people teach themselves. Seth builds everything around a metaphor that gives people scaffolding, because "the only kind of learning that really happens is autodidact self-learning." Give someone the structure to figure it out and they'll never forget it.
Name the baggage, drop the baggage, ship the work.
The easiest thing to do with our freedom is pretend it doesn't exist. A man with nine million dollars in the bank told Seth he has to keep doing the work he's known for, because he needs to make a living. No, you don't. Same with the student three years into a four-year degree he hates who says he has to finish. You can choose to finish. Nobody is making you.
We stay stuck because it's comfortable. It keeps us safe, guarantees an excuse, takes us off the hook. No agency means no responsibility.
It isn't friction, it's hidden entanglements. Friction sounds like a law of nature you can't argue with. Entanglements are long-told stories about how the world is, who we are, what we fear, where our status sits. They form an invisible web, and unlike physics, they're ours to cut.
The tell is when a problem gets treated like a situation. In Canadian Inuit territory, people are 500 times more likely to contract tuberculosis than someone in Toronto. We know how to cure it, for a tiny fraction of the healthcare budget. Calling it a situation is what lets everyone off the hook.
The blue sweater. As a high school sophomore, Jacqueline Novogratz wore her favorite sweater, a gift from her uncle, blue and white wool with the Alps on it. Cheerleaders teased her for it. She went home and dropped it in a Goodwill box. Fifteen years later, running through the streets of Rwanda at 7:00 in the morning, she saw a seven-year-old boy wearing it. She chased him down, looked in the collar, and found her own name on the tag. That was the moment she let go of being the Stanford grad on the fast track at a New York bank. She has spent the decades since building Acumen and its patient capital model, and by Seth's last count, 600 million of the poorest people on earth live better because of it.
What makes someone a leader: they decide to. It has nothing to do with your title. You can lead from anywhere in an organization.
Seth gets stuck every single day, and most of the time he stays stuck. That's fine. What matters first is clarity: who is this for, and what is it for?
Getting unstuck always means leaving something else behind. The woman with more figure skating gold medals than anyone in history didn't get them by having a life. She got them by having no life for fifteen years. Completely unstuck on gold medals. Deeply stuck on everything else.
It's the word "but" that traps you. We only feel stuck when we want one thing and another, and won't be happy without both. Swap the but for an and, or admit which one you're trading away.
Six to nine ideas a day, one gets published. Most never get past three words. If you need the perfect idea before you begin, you will never begin.
Find the room inside the system, then leave when the system is the obstacle. Jesse Cole inherited minor league baseball's constraints and worked inside them: ridiculous name, puns, a cheering section of seventy-year-old women called the Nana Bananas, players recruited for charisma over hitting. Years of sellouts, home and away. Then the league itself became the thing in the way, so he left it.
Multiple things fail at every Bananas show, every single night. That's the price. The question worth sitting with is what it actually costs you to not be perfect. If Seth's book The Practice were one page long, it would say give up your commitment to being perfect and be useful instead.
The reason most people don't try isn't cost or risk. Before an event with 185 people, Seth turned the 80-page PDF of bios into a 7,000-word article about everyone there, then had it read back to him in a clone of his own voice, and listened on the drive over. Thirteen minutes, twenty dollars. Nobody else at the event had tried anything like it. "So what's keeping you from doing something like that?"
It's not a failure muscle, it's a generous failure muscle. The internet version has become a failure Olympics, asking a donut shop for a dozen free donuts just to get rejected. Seth calls that selfish. The real question is "Who might I be able to help with the next thing that might fail?"
Stress and tension are not the same thing. Stress is wanting two things you can't both have. Reduce it. Tension is the engine, and you can't shoot a rubber band across the room without pulling it backward first. Taylor Swift announcing 8,000 seats is inflicting tension on her fans, and that tension is what releases into joy. No concert, no tension, no joy.
Great teachers create the conditions for people to see the gap. There's always a moment where you know you could learn something and haven't yet, and that moment feels like incompetence. Some people meet it and opt out because nobody convinced them the tension was worth it.
Effective leadership is voluntary. Force people to follow you and you're a manager. Teaching canoeing at summer camp in 1977, Seth was competing with windsurfing and horseback riding for twelve-year-olds who could choose anything. He couldn't require anyone to come to his dock, so he built the conditions instead. And when a kid said he'd rather go sailing: "It's not my job to persuade everyone. It's my job to persuade someone."
Jackson Pollock wanted two things and got neither. Three years as the most celebrated American painter of the century, then he told Lee Krasner he didn't want to spend his life painting cover versions of Jackson Pollock. He changed his method, format, even his canvas sizes. His momentum guaranteed a big first show. Everyone hated it and nothing sold, and what followed was a spiral that ended in a fatal crash. Coming up, he had accepted rejection as the cost of the work. Later he wanted that and acclaim and wealth. Needing both, he got neither.
Rules in one area free up energy for another. No alcohol, no drugs, no meat in forty years, no dairy. The point isn't the rules, it's that Seth never renegotiates with himself about any of it.
Seth's answer to the champagne question: he doesn't celebrate. The day he sold his company to Yahoo he wasn't happy, because it was the end of something. Hitting the New York Times list a second time, he cried, not from joy but because he felt nothing. "I had done the work. I didn't need to make the list." His prize is noticing that someone he talked to yesterday is closer today to where they want to go.
Action
Name one thing you tell yourself you have to do. Say it out loud as a choice instead. Do you still choose it?
What's the thing you'd try this week if the only cost of failing was that it didn't help anyone? Who would it help if it worked?
If you enjoyed this episode with Seth Godin, check out my in-person conversation with Jesse Cole, owner of The Savannah Bananas!
Podcast Chapters
00:00 Apply for the Learning Leader Circle
00:59 Meet Seth Godin
03:06 Why There's a Knot in the Pretzel
06:10 Name It, Drop It, Ship It
09:30 Not Friction, Hidden Entanglements
10:59 The Blue Sweater in Rwanda
14:42 Seth Gets Stuck Every Day
16:25 How He Blogs Every Single Day
17:10 The Bananas Found Room in the System
21:42 The Book That Weighs 18 Pounds
25:11 Thirteen Minutes, Twenty Dollars
27:05 The Generous Failure Muscle
28:05 Tension Is the Engine, Stress Is the Trap
30:17 You Can't Make Anyone Follow You
33:05 Pollock Wanted Two Things
35:22 Designing the Default
39:35 What Canoeing Taught Him About Leadership
41:26 The Champagne Question
45:17 EOPC710: Ravi Gupta - The Anti-Dabbler's Guide to Mastering One New Skill Every Year, Why Presence Isn't Enough, Bourdain's Masterclass in Humility, and Pairing Reasonable Goals With Delusional Ones
11/10/2026 | 1h 2minThe Learning Leader Show with Ryan Hawk www.LearningLeader.com
New Book - The Price of Becoming www.LearningLeader.com/Becoming
Connect with me on socials
Twitter/X - @RyanHawk12
Instagram - @RyanHawk12
Join 10's of thousands of leaders, subscribe to Mindful Monday
My guest:
Ravi Gupta is the founder of RePublic Schools, whose flagship Nashville schools became the first in Tennessee to rank in the top 5% statewide for both growth and achievement. He co-founded Arena, which trained more than 7,000 political staffers, worked on the first Obama campaign, and wrote speeches for UN Ambassador Susan Rice. Today he runs The Branch, a media company fighting polarization. His new book is The Invisible List: One Passion a Year, Every Year.
Key Learnings
One new passion a year, every year. When Ravi left his job running schools, he decided to treat every year like a school year with himself as the only student. He's done it for seven years. Surfing, tennis, screenwriting, a novel, Italian cooking.
Be an anti-dabbler. The seductive version is a little boxing, a little salsa dancing, a little cooking. You get fifteen years of sampling and none of the skill. Pick the thing, commit to the year, see it through even if you come to regret the pick.
The rule that makes it work: no new thing midyear. You can maintain old passions. You cannot start a new one.
He broke his own rule and learned why it exists. Bored one day and avoiding his cooking, Ravi walked into a Muay Thai gym on his corner. He loved the class, walked out, and told himself it was off the table until January 1. The pull wasn't interest. It was the rush of early wins, and that rush is the most convincing form of procrastination there is.
Trying something and quitting can be worse than never trying. Once you've tasted it, you start seeing it everywhere, and you replay the version of your life where you stuck with it.
Pair a reasonable goal with a delusional one. Ravi almost always hits the reasonable one. He almost never hits the unreasonable one right away, but he often gets there eventually. The pairing is the point.
Tim Ferriss's observation on why that works: there's less competition for big crazy goals, because so few people think that way anymore.
December is the meta-learning month. Thanksgiving to New Year's, Ravi wraps up the current year and pulls together the next one: the books, the experts, the sequence, what it actually means to be great at the thing.
Don't start researching it in August. He has next year's candidates in his head by late summer, but he refuses to buy books or line up coaches until December. Planning next year's passion is an elaborate way to avoid this year's.
Output goals need a skill set attached. Example: hiking an outrageous number of national parks. Ravi's counter: keep the output goal, but build the skills underneath it. Pitching a tent, starting a fire, navigation, survival prep. Then the year leaves you with something beyond a number.
Each year becomes a chapter. 2020: surfing. 2021: tennis. Childhood is memorable because it's divided into grades with names attached. Adult years blur into one undifferentiated stretch, and Ravi thinks that blur is part of why people get depressed looking backward and forward.
The reframe on aging: turning 50 in seven years is only grim if those are seven blank years. Seven more passions is a different sentence entirely.
Join an accountability group. The Invisible Posse is a group of readers all pursuing their own skills at the same time, at readinvisiblelist.com. New challenge every two weeks, a leaderboard, points for doing the work. The list is a solo project. The accountability isn't.
Do the thing publicly in the first two weeks. The group's first challenge was to do your new skill in front of people immediately. The winner was a man learning to sing who sat his cousins down on vacation and performed a whole song. Once you're past being judged, you're doing it instead of planning it.
The second challenge is the one most people skip: get feedback from someone who actually knows how to do it, then do it again.
Protecting your time is on you. From Neil Strauss, in a writing group Ravi joined during his writing year: "It's nobody's responsibility but your own to protect your time." The complaint that nobody respects your boundaries is a complaint about your own boundaries.
Which means the conversation has to be explicit. You take Saturday, I take Sunday. One of us has mornings. I've carved out 45 minutes and you know about it. Writing is especially hard to defend because it doesn't look like work.
Treat your session time like a flight. Strauss again, this time on writer's block. Nobody waits to feel motivated before going to the airport. You wake up early, sit in the security line, get wedged next to someone taking up too much room, and you never treat any of it as optional. Put the sessions on your calendar and defend them the same way, whatever your thing is.
The question that ended writer's block for good: your mom is a nurse, does she get nurse's block? When Ravi still stalls, he falls back on Hemingway's one true sentence, and since the surgery, he dictates rather than types if that's what it takes to get words out.
Teach tools, not answers. The book's dedication is to the teachers who gave Ravi tools instead of answers. He trained his own teachers not to be "the sage on the stage." He can't name a single fact those teachers gave him. He can name what they built in him.
A doctor friend gave him a portable framework instead of an opinion. When Ravi tore his bicep, friends told him to take peptides. Rather than answering yes or no, his doctor friend walked him through the questions: what's the theoretical mechanism, what do controlled peer-reviewed trials actually show, what are the downsides? Ravi now uses it on everything.
In a disagreement, show your process, not just your conclusion. If you lay out how you arrived at an answer, the other person may not accept the answer but can engage the method, or show you where you went wrong. It lowers the heat.
The 10 out of 10 version of humility. Andy Greenwald wrote a piece ripping Anthony Bourdain, comparing him to a lion declawed and put in a zoo. Bourdain read it, told his staff, "This guy got me," then had the team invite Greenwald over for a conversation.
Nurturing your own passions is not stealing from your family. The oxygen mask applies. Your kids will be more inspired by you and your spouse, more drawn to you if you're a person who is actually lit up by something.
Presence alone is a thin theory of parenting. Ravi would rather have had a father who skipped a game to pursue something real and then talked about it over dinner than one who dragged himself to the bleachers out of obligation. Availability matters. So do wisdom, example, and energy.
People are drawn to anyone who is fully activated. The musician playing a Nashville bar at 2:00 PM on a Wednesday who is completely in it, playing like the room is full.
Ravi's champagne moment a year from now: settling down. Not flying airplanes, not the bestseller list. He says he needed the seven years of this process to come out a whole person capable of devoting himself to someone else again.
A relationship or parenting year is a legitimate list item, but not the first one. Most people have been too selfless already and need the selfish pursuits first. And it only works if you attack it systematically, with real metrics, because that kind of goal gets squishy fast.
Action
What is your one thing for 2027? Name the reasonable goal you'll hit with consistent effort, and the delusional one that scares you a little.
Look at your calendar for next week. Where is the time for that thing, and who in your life needs to know it's protected before Monday?
If you enjoyed this episode with Ravi Gupta, check out episode #647 with Tim Ferriss: Chasing Your Curiosity
Episode Chapters
00:00 Apply for the Learning Leader Circle
01:36 Meet Ravi Gupta
03:09 Three Injuries, One Arm
05:03 Teachers Who Give Tools, Not Answers
06:58 A Framework Instead of an Opinion
10:36 Why Hosting a Show Changes Your Mind
13:59 Bourdain: "This Guy Got Me"
16:28 His Mom and the Yale Law Tour
20:31 One Delusional Goal, One Reasonable One
23:56 The Anti-Dabbler Rules
29:13 Nobody Protects Your Time But You
33:25 How He Actually Became a Writer
37:06 How He Picks the Year's Skill
38:50 Salsa and the Unfinished Ending
40:35 The Burnout Wake-Up Call
43:09 Your Passions Make You a Better Parent
48:19 The Invisible Posse Challenges
51:09 The Champagne Question
54:05 Make Relationships a Skill
55:55 Skills Underneath the Goal
01:00:19 EOPC709: Vanessa Van Edwards - How to Connect with Anyone, Master Small Talk, and Ask the 9 Power Questions That Deepen Every Relationship
04/10/2026 | 52minThe Learning Leader Show with Ryan Hawk www.LearningLeader.com
New Book: The Price of Becoming www.LearningLeader.com/Becoming
Connect with me on X: @RyanHawk12
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My Guest: Vanessa Van Edwards is a behavioral researcher, Harvard instructor, and founder of Science of People. Her books Captivate and Cues have been translated into 18 languages, and her work reached more than 300 million people last year. Her new book is Conversation: How to Connect with Anyone and Make Every Interaction Count.
Key Learnings
Small talk is required for big talk. You can't skip it. You can do it better. Conversation is a skill with micro skills underneath it, and small talk is one chapter.
Two traps make small talk painful. Autopilot (asking questions without actually connecting) and going for facts instead of stories.
Awe is the best small talk ingredient. "Wow, that's amazing," or "What is that?" Positive awe is wow. Negative awe is compassion: "Everything okay? Can I help?" Both solicit stories. Both work only if you mean it.
Awe beats a compliment. A compliment lands. Being visibly wowed by something invites the story behind it.
Be story ready. When someone asks how you are, don't hand back good, fine, busy. Have something loaded: "Today the craziest thing happened." You break the script with your answer before anyone has to break it with a question.
Flip your questions into story hunters. Not "how are you" but "What's been good?" or "Tell me something good." Slight change, big shift toward optimism.
Or check in on something specific from before. "I noticed you dedicated the book to your daughters. How old are they now?" The update question does the work that the generic one can't.
Katie Couric never asks "what do you do?" She asks "What do you like to do?" Vanessa found it in Couric's memoir. One-word swaps have major potential.
Turn small talk into a treasure hunt. Everyone has gold. You don't know what it is yet. Your job is to ask the questions that find it.
Treasure hunting also kills the awkwardness. Vanessa calls herself a recovering awkward person. Her problem for years was that her goal in conversation was to be impressive. No good conversation comes from that.
Curiosity has to be innate. Vanessa thinks nearly everything is teachable. Not this. If you aren't actually curious about the person, the techniques will read as manipulative, and eventually you get found out.
The rule on using someone's name: if you're already thinking about it, use it. If you're not thinking about it, don't. That's the whole test.
Three levels of connection, and you have to go in order. From Dr. Dan McAdams. Level one is general traits: occupation, hometown, family status. Level two is personal concerns: goals, motivations, values, what drives and worries someone. Level three is self-narrative.
Put your work relationships in level two. That's the practical instruction. Most people stall at level one and assume level two isn't work-appropriate. It is, and conversations get more engaged, collaborative, and productive once you're there.
Level three is about frames, not facts. Two people can have identical facts and completely different stories about what those facts mean.
Self-narratives are self-creating. People who see themselves as lucky approach the world as lucky people. They spot more opportunities, think more laterally, and create more surface area for good things. Unlucky people do the same thing in reverse.
Narratives are editable. They're not Enneagram or Myers-Briggs. They shift, usually on an annual scale, most often through conversation with someone you trust. Journaling alone rarely does it.
The five re-storying questions. Who am I now? Who do I want to be? How do I get from here to there? How do I make change stick? Who can help me?
Be a loud liker. A friend asked Vanessa to assess a date named Tim. Her read: meh. Before she could say so, the friend told her Tim had loved her, thought she was fun, and bought all her books. Vanessa's opinion of Tim reversed on the spot. She was embarrassed by how fast.
The lesson from Tim: when someone clearly likes you, you feel at ease, you feel more likable, and you like them back. Very few of our impressions of people are fixed.
You can't like too loudly if it's authentic. Vanessa's hot take. Gushing is fine. The only failure mode is inauthenticity, or liking so loudly you prevent the conversation from happening.
Warmth, then competence. Susan Fiske's research, quoted directly: "Competence without warmth leaves people feeling suspicious." Leading with data and numbers reads like you're hiding something. Warmth is the lubricant that lets people accept your competence.
Powerful people get informal fast. BJ, a CEO I hadn't seen in a year, leaned into the camera on a Zoom and said, "This makes me so happy." Straight past the formality. The myth is that power requires sterility. The most powerful people have enough confidence in their status to give likability away.
Proxemics: we read physical space as emotional space. Four zones. Public is five to seven feet. Social is four to six. Personal is a foot and a half to three feet. Intimate is under 18 inches. Leaning toward the edge of someone's intimate zone signals that you want to be close, and it works on camera too.
Let your body do what it wants when you like someone. It already wants to lean in, make eye contact, get closer. Most of us hold it back.
Shared language is the key to our hearts. I give my daughter's friends nicknames. Millie is Mill Dog. Georgia gets "What up, G?" Vanessa calls that an inside joke, and inside jokes create belonging. It also proves you remembered them.
Availability is more attractive than attractiveness. In Dr. Monica Moore's bar study, the most attractive women were not approached most. The women who sent the most availability signals were: brief glances, long glances, body angling, smiles. It took roughly 35 signals an hour to get approached.
Never ask "been busy lately?" It invites the other person's brain into pessimism, primes them to search for everything they're behind on, and reminds them they should be somewhere else. Then they complain, and listening to complaining is the most exhausting form of conversation there is.
Bragging about being busy makes you look less competent. The research is counterintuitive. People think volume signals importance. It reads as someone who doesn't have a handle on things.
"Oh, good busy or bad busy?" 90% of the time you get a real story about a project or a goal. The other ten percent opens the door to "What's going on? Can I help?" Either way, you just moved to level two.
Two secret doors into level two at work: goals and learning. A goal taps motivation, core values, and future self. Learning activates growth mindset.
Test yourself on the five people you work with most. Do you know each one's current work goal and personal goal? Vanessa knows who on her team is training for a marathon and what their KPIs are.
Make it a norm, not an occasion. Vanessa's global team opens every weekly call with "tell me something good." One quick win each, personal or professional. It gave wins a place to live that isn't bragging, and it replaced the boring small talk that used to open the call.
The nine power questions, for the most important people in your life. Three per level. 1) Working on anything exciting these days? 2) Have any fun plans coming up? 3) What's your personal passion project? 4) What's your biggest goal right now? 5) What have you always wanted to learn? 6) What do you love to talk about? 7) What book, movie, or TV character are you most like and why? 8) How do you feel most misunderstood? 9) What would you do if you weren't afraid?
Question four is also a secret to strong marriages. Partners discussing shared dreams is vision casting. It reminds you both where you're going and shapes what you do today. Some marriages live in strategy. Most get trapped in logistics.
Question seven is the backdoor to level three. Asking someone their self-narrative directly doesn't work. Asking what character shares their values, choices, and personality gets the richest narrative answers, because it makes them step outside themselves.
If you don't like people, treat it like a social gym. The first few reps hurt and you can only do three. And when you're stuck with someone you don't like, the intention becomes: how do I get to know this person enough to find one thing I authentically like? That's a muscle.
Go to the gym with a plan. Wandering machine to machine is aimless and exhausting. So is walking into a room with no conversational intention. Vanessa's plan is always the same: discover.
Vanessa's champagne moment a year from now: a conversation coach in every company and every school. She thinks the chief conversation officer role is coming. We've moved our small conversations onto Slack, which is transactional, and lost the water cooler. If we want engaged teams and less burnout, someone has to build the safe spaces and the prompts. She has already certified 70 coaches.
Reflection Questions
Who in your life has clearly told you they like you? Now flip it. Who have you been quietly appreciating without ever saying it out loud? Say it this week.
Pick the five people you work with most. Can you name each one's biggest goal right now, at work and at home? If not, that's your next five conversations.
Where are you using a conversational technique as a tool instead of out of genuine curiosity?
If you enjoyed this episode with Vanessa Van Edwards, watch our first conversation together, Episode #468 - The Secret Language to Charismatic Communication. (Show notes)
Episode Chapters
00:00 Apply for the Learning Leader Circle
01:17 Meet Vanessa Van Edwards
02:37 The Small Talk That Kills Your Soul
03:52 The Two Traps of Small Talk
06:11 Awe Is the Best Opener
09:10 Turn Small Talk Into a Treasure Hunt
11:32 Curiosity Can't Be Faked
12:58 The Rule on Using Someone's Name
16:02 The Pressure to Be Impressive
18:34 Three Levels of Connection
21:18 The Five Re-Storying Questions
24:40 Be a Loud Liker
28:11 The Social Gym
29:33 Warmth, Then Competence
33:01 Proxemics Works on Camera
34:40 Nicknames and Shared Language
36:45 Availability Beats Attractiveness
39:18 Never Ask "Been Busy Lately?"
42:37 Two Secret Doors to Level Two
47:07 What Character Are You Most Like?
49:09 The Champagne Question
50:33 EOPC
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