Today, I interview fellow Ottawan and the founder and CEO of Shopify, Tobi Lütke. In case you’re still new to the internet, Shopify is the largest ecommerce platform that allows people to easily set up online storefronts to sell everything from jewelry to surfing lessons.

Shopify began as a simple two man operation selling snowboards online, but it became clear rather quickly that it had the potential to grow into much more. Now Shopify employs more than 4,000 people and supports more than 600,000 businesses online. It’s a remarkable story, with a remarkable leader at the helm.

There was so much I wanted to talk to Tobi about that we hop around quite a bit. Here are a few of the topics we discuss:

• Tobi’s thoughts on how video games helped him prepare to run a company
• How selling snowboards online slowly transitioned to the creation of one of the biggest tech companies in the world
• Why Tobi intentionally headquartered Shopify outside of Silicon Valley and how that fits into his overall growth strategy
• One of the most underrated resources Tobi leans on to mine nuggets of wisdom when trying to get insight or solve a problem
• The hard and valuable lessons Tobi learned as they scaled from a 2 employee company to a 4,000 employee company
• What the “Tobi test” is, and how it helps Shopify team members become more adaptable, unified and prepared when things go haywire
• How employees use the “trust battery” and how it fosters better teamwork, communication, and productivity throughout the company
• The benefits of hiring employees in a “secondary market” as opposed to a “primary market” and how that contributes to the unique culture at Shopify
• Tobi’s decision-making process and his philosophy on making quick vs analytic decisions
• Tobi’s unusual morning routine that gets him in the right mindset to tackle the day
• His optimistic view of AI and machine learning and how they will impact the way we do things in the future

And more…

Whether you’re building a business of your own, want to create a more dynamic and unified culture at work, or just like hearing entrepreneur war stories, this episode will not disappoint.

---

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Today’s guest is Stratechery author and founder Ben Thompson. If you’re an investor in Silicon Valley, work at a tech start-up, or just love to geek out on technology and business analysis, odds are good that Stratechery is on your short list of must-read blogs.

What started as a side project, quickly ballooned into one of the most influential tech blogs on the web. The New York Times called Stratechery, “one of the most interesting sources of analysis on any subject.”

I agree.

In this interview, Ben and I cover a lot of ground. Here are a few of the things we discuss:

• Learn once and for all how to pronounce Stratechery. :)
• How Ben’s business model was developed and how he massaged it over the years to become what it is today
• The one metric Ben looks at each day to gauge the health of his business
• How Ben deals with people who rip off his work and pass it off as their own
• Ben’s thoughts on pricing, free trials, content and other important aspects of online membership sites
• How Ben structures his day to churn out such incredible content so consistently
• How Ben handles being wrong on his site, and his process for screening his work for confirmation bias
• How the internet has changed the traditional view of supply and demand, and what companies should do about it
• What Ben would teach an MBA class about internet strategy (if you do any business online, you need to hear this)
• What it would take for a start-up to overtake Google or Apple, and the vulnerabilities that all companies share, no matter how big or profitable
• The new era of technology and how companies like Netflix, Airbnb, and Amazon are doing it right (and what you can do in your own business to take full advantage)

This is one of the most jam-packed interviews I’ve done on the Knowledge Project. Ben’s answers are so thoughtful and informative that you’re going to want to have a notebook handy.

For comprehensive show notes on this episode, including a full edited transcript, go to https://fs.blog/podcast/

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There are only a handful of websites that I read religiously. One of those is MarginalRevolution.com, started by my next guest, Tyler Cowen.

Other than hosting one of the most popular economic blogs in the world, Tyler is also an economics professor at George Mason University, a regular New York Times columnist, and the author of over a dozen books, including Average is Over, and The Complacent Class.

With such a prolific guest, it’s no wonder that we cover a lot of ground. In this episode, we discuss:

• How the future of labor will look drastically different than it does today, and what we can do to future-proof our livelihood
• The pros and cons of virtual reality and the impact it could have on society
• The fate of newspapers and how information will be more and more “bundled” according to our tastes and preferences
• Race relations in the world, and how in many ways we’ve taken discouraging steps backwards
• How we’re losing touch with the physical world, and some of the symptoms that indicate that we could be in for a rough ride
• What Tyler suggests doing to improve decision making and how important (and rare) that skill will be in the coming years
• Tyler’s advice to parents about how to foster resilience, tenacity and internal drive in their children
• Tyler’s “quake books” and the reading process he’s developed over the years that keeps him sharp
• Why giving books as gifts can be dangerous
• The one skill every person should possess before Googling anything
• What playing competitive chess as a child taught Tyler about how he thinks and views the world today

And much more, including Tyler’s thoughts on minimum wage, bitcoin, and his favorite television programs.

If you want to upgrade your thinking so you’re prepared for the brave new world that’s rapidly developing before our eyes, you won’t want to miss this fascinating episode.

For comprehensive show notes on this episode, including a full edited transcript, go to https://fs.blog/podcast/

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My guest for this short episode of The Knowledge Project is a man who wears many hats.

Ali Almossawi is a San Francisco-based author of books on critical thinking and computer science education, and the creator of An Illustrated Book of Bad Arguments. He is also a principal engineer at Apple and was formerly employed as a data visualization engineer by Mozilla.

His books have been read by 3 million readers, translated into 20 languages, and have sold over a quarter million copies in print.

This interview is only 20 minutes along, but there was a lot I wanted to cover, so we move pretty fast. Specifically, we cover:

• The unique format Ali chooses when writing a book to help people understand the concepts more deeply
• The place for empathy in algorithmic thinking and how we can be more empathetic in our daily interactions with each other
• Ali’s note taking process and how he tracks the ideas and topics he’d like to explore
• Ali’s daily routine and the “algorithms” he uses to make the most of his day
• The single habit that has the most profound impact on Ali’s day to day
• The cost/benefit of sharing on social media and the impact it has on society as a whole

And more.

If you’ve ever wanted to improve the way you process information, think more clearly and make better decisions, you won’t want to miss this interview.

***

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I have wanted to do this interview for a long time. On this episode, I am thrilled to have Annie Duke, former professional poker player and author of the new book, Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts.

Annie has a very interesting background that makes her uniquely qualified to speak about high-level decision making. As an author, speaker, world-class poker player, and academic in the fields of psychology and cognitive theory, Annie understands the intersection of luck, skill, and making decisions in uncertain, chaotic environments better than most people on the planet.

This is a whirlwind of an episode, and we cover all kinds of fascinating topics, including:

• The strange circumstances that shifted Annie’s path from finishing a Ph.D. in linguistics to becoming a professional poker player
• What it was like to be a female poker player in a predominantly male sport (especially before poker had become socially acceptable)
• What drew Annie into such a high stakes, time-pressured environment and why she felt like poker was the perfect fit for her
• How her graduate work in psychology informed the way she approached the game of poker — and helped her rack up wins
• How she finds the signal in a very noisy stream of feedback
• The big mistakes Annie noticed other players making that were stalling their progress in the game but allowed her to make giant leaps forward
• The role that mental models played in her learning process (and which models Annie liked to lean on the most in a high stakes game)
• The power of surrounding yourself with people that can help you expand your circle of competence — and how that made all the difference in Annie’s development as a player
• Confirmatory and exploratory thought, and how one helps us to be “accurate” and one helps us to be “right.”
• The secret pact you should be making with the people who are closest to you

And so much more.

This episode is just under two hours long, but there’s no fat in it. Annie delivers a masterclass in making the smartest decisions we can, even when our hubris insists otherwise. Do some finger stretches before hitting play, because you’re going to be taking some serious notes.

Please enjoy the interview!

***

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On this episode of The Knowledge Project, I’m happy to have William MacAskill.

William is the co-founder and President of the Centre for Effective Altruism (CEA) and an Associate Professor in Philosophy at Oxford University. He is also the founder and president of 80,000 Hours, the co-founder and vice-president of Giving What We Can, and the author of Doing Good Better: Effective Altruism and a Radical New Way to Make a Difference.

William’s work is primarily focused on encouraging people to use reason and evidence to find the best possible ways they can use their resources to make the biggest possible impact in the world.

We cover a lot of ground in this interview, including:

• Why good intentions aren’t enough when giving to charity and how we can do better
• How William's giving philosophy was formed and how it developed into The Centre for Effective Altruism
• The best metrics to assess how good a charity is before donating a dime
• How letting our emotions guide our charitable giving can lead to ineffective, and sometimes harmful outcomes.
• How many charities today unknowingly reward low dollar donors and sell themselves short millions of dollars in potential donations
• A powerful thought exercise to help you gain a different but valuable perspective about helping the poor and suffering in the world
• The one cognitive bias William believes is the most damaging to any business, organization or individual
• William’s foundational values that guide his day to day decisions and actions
• William’s take on “radical honesty” and when honesty can be taken too far and is no longer constructive
• William’s definition of success and the imaginary conversation he has with himself on his deathbed to make sure he’s on the right track (this is awesome)
• The most common mistake William sees people make over and over (and the embarrassingly simple way to avoid making it)
• And then to wrap up, I gave him a softball question: What is the purpose and meaning of life?

If you’ve wanted to make more of a positive impact in the world around you, this insightful interview will give you plenty to think about. Your resources are precious and should be optimized to improve the lives of those you help. I don’t know of a better person to guide you than William.

***

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In this episode of The Knowledge Project, I have the brilliant Robert Greene. Robert is the

author of 5 New York Times bestsellers, including The 48 Laws of Power and The 33 Strategies of War. He's also written on mastery and seduction.

Robert’s books have been somewhat controversial over the years and have been called amoral, cunning, and even ruthless for what they reveal. Yet millions of readers, from mid-level managers to hip-hop royalty and corporate executives have revered his work as a sort of canonized scripture for the ambitious.

In this conversation, we cover a lot of ground, including:

• Why Robert believes his first book, 48 Laws of Power has continued to sell steadily for over two decades.
• What Robert calls “alive time” and “dead time” and how we can optimize each day to be filled with “alive time” and live the life we’re proud of
• The one skill that determines how far you’ll get in life, no matter how talented you are in anything else
• Robert’s research method and how he finds such unique and interesting examples
• What Robert looks for when he reads, and what qualities separate good books from excellent books
• How Robert developed his famous note card system to extract the meat out of anything he reads
• Why Robert insists on writing all his notes longhand even though it’s less convenient and less accessible than taking notes digitally
• What Robert’s daily routine looks like, particularly when he’s writing and researching for a new book
• What Robert considers to be the single greatest power any human has, and what we can do to strengthen it
• How having unfettered access to information is actually making us dumber in very important ways and what we can do about it
• How to fine tune your “bullshit detector” so you’re able to tell the difference between pretenders and performers. (As a bonus, Robert shares a few ways you can improve your bullshitting skills when it becomes necessary)

And a lot more.

Plus, Robert gives us a sneak peek into his newest project, The Laws of Human Nature, which explores the hidden motivations that drive what we do and say.

This interview is packed to the brim with interesting and actionable insights that I think you’re going to love. Grab a pen, a notebook, and a glass of wine and enjoy!

***

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Since the popularity of Obstacle Course Racing, or OCR, has exploded onto the scene, there has been one woman who has dominated the sport: Amelia Boone.

Amelia ran her first race in 2011 after some prodding from a co-worker, and though she says she stumbled her way to an unimpressive finish, she was smitten. She has since amassed over  50 podiums and two dozen victories, including the Spartan Race World Championship in 2013, and the World's Toughest Mudder (three times!) in 2012, 2014 and 2015.

Oh, and her 2014 victory came just eight weeks after major knee surgery.

Though she vehemently denies it, Amelia is superhuman.

This interview is a little different than others you may have heard on The Knowledge Project but no less fascinating.

We cover a wide variety of topics including habits, reading, self-reliance, and training.

Specifically, you’ll learn:

• Why Amelia was drawn to obstacle racing even though running was something she despised
• The complementary connection between her sport and her professional work and how racing has made her a more effective attorney
• How Amelia fights physical and mental fatigue when most people quit (she even shares a story of how she dealt with a vacant support station halfway through a 100 mile race)
• What she does to develop grit and resilience so she knows she can rely on herself when things get rough
• Amelia’s “to-do list” trick that makes sure she’s productive — you’ll want to steal this
• How a serious injury taught Amelia some of her most powerful lessons about who she is and what’s important to her
• What Amelia’s parents did to teach her to be self-sufficient from a very young age
• How she learned to deal with setbacks, and how careful she is with the language she uses when she speaks to herself when things go wrong
• Why Amelia runs with a Sharpie and the same playlist she’s listened to for the past 5 years
• How Amelia transformed herself from a casual weekend warrior to one of the most finely tuned athletes in the world

Whether you’re an athlete, a weekend jogger, or the only exercise you get is the leisure stroll from the couch to the refrigerator, there are lots of insights and plenty of inspiration waiting for you in this interview.

***

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On this episode of the Knowledge Project, I’m joined by the fascinating Dan Ariely. Dan just about does it all. He has delivered 6 TED talks with a combined 20 million views, he’s a multiple New York Times best-selling author, a widely published researcher, and the James B Duke Professor of Psychology and Behavioral Economics at Duke University.

For the better part of three decades, Dan has been immersed in researching why humans do some of the silly, irrational things we do. And yes, as much as we’d all like to be exempt, that includes you too.

In this captivating interview, we tackle a lot of interesting topics, including:

• The three types of decisions that control our life and how understanding our biases can help us make smarter decisions
• How our environment plays a big role in our decision making and the small changes we can make to automatically improve our outcomes
• The “behavioural driven” bathroom scale Dan has been working on to revolutionize weight loss
• Which of our irrational behaviors transfer across cultures and which ones are unique to certain parts of the world (for example, find out which country is the most honest)
• The dishonesty spectrum and why we as humans insist on flirting with the line between “honest” and “dishonest”
• 3 sneaky mental tricks Dan uses to avoid making ego-driven decisions
• “Pluralistic ignorance” and how it dangerously affects our actions and inactions (As a bonus, Dan shares the hilarious way he demonstrates this concept to his students on their first day of class)
• The rule Dan created specifically for people with spinach in their teeth
• The difference between habits, rules, and rituals, and why they are critical to shaping us into who we want to be

This was a riveting discussion and one that easily could have gone for hours. If you’ve ever wondered how you’d respond in any of these eye-opening experiments, you have to listen to this interview. If you’re anything like me, you’ll learn something new about yourself, whether you want to or not.  

Enjoy!

***

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On this episode of the Knowledge Project Podcast, I chat with Patrick Collison, co-founder and CEO of the leading online payment processing company, Stripe. If you’ve purchased anything online recently, there’s a good chance that Stripe facilitated the transaction.

What is now an organization with over a thousand employees and handling tens of billions of dollars of online purchases every year, began as a small side experiment while Patrick and his brother John were going to college.  

During our conversation, Patrick shares the details of their unlikely journey and some of the hard-earned wisdom he picked up along the way. I hope you have something handy to write with because the nuggets per minute in this episode are off the charts. Patrick was so open and generous with his responses that I’m really excited for you to hear what he has to say.

Here are just a few of the things we cover:

• The biggest (and most valuable) mistakes Patrick made in the early days of Stripe and how they helped him get better
• The characteristics that Patrick looks for in a new hire to fit and contribute to the Stripe company culture
• What compelled he and his brother to move forward with the early concept of Stripe, even though on paper it was doomed to fail from the start
• The gaps Patrick saw in the market that dozens of other processing companies were missing — and how he capitalized on them
• The lessons Patrick learned from scaling Stripe from two employees (he and his brother) to nearly 1,000 today
• How he evaluates the upsides and potential dangers of speculative positions within the company
• How his Irish upbringing influenced his ability to argue and disagree without taking offense (and how we can all be a little more “Irish”)
• The power of finding the right peer group in your social and professional circles and how impactful and influential it can be in determining where you end up.
• The 4 ways Patrick has modified his decision making process over the last 5 years and how it’s helped him develop as a person and as a business leader (this part alone is worth the listen)
• Patrick’s unique approach to books and how he chooses what he’s going to spend his time reading

...life in Silicon Valley, Baumol’s cost disease, and so, so much more.

Patrick truly is one of the most warm, humble and down to earth people I’ve had the pleasure to speak with and I thoroughly enjoyed our conversation together. I hope you will too!

***

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Just when I start to think I’m using my time well and getting a lot done in my life, I meet someone like Barbara Oakley.

Barbara is a true polymath. She was a captain in the U.S. Army, a Russian translator on Soviet trawlers, a radio operator in the South Pole, an engineer, university professor, researcher and the author of 8 books.

Oh, and she is also the creator and instructor of Learning to Learn, the most popular Massive Open Online Course (MOOC) ever(!), with over one million enrolled students.

In this fascinating interview, we cover many aspects of learning, including how to make it stick so we remember more and forget less, how to be more efficient so we learn more quickly, and how to remove that barriers that get in the way of effective learning.

Specifically, Barbara covers:

• How she changed her brain from hating math and science to loving it so much she now teaches engineering to college students
• What neuroscience can tell us about how to learn more effectively
• The two modes of your brain and how that impacts what and how you learn
• Why backing off can sometimes be the best thing you can do when learning something new
• How to “chunk” your learning so new knowledge is woven into prior knowledge making it easily accessible
• The best ways to develop new patterns of learning in our brains
• How to practice a skill so you can blast through plateaus and improve more quickly
• Her favorite tactic for dealing with procrastination so you can spend more time learning
• The activities she recommends that rapidly increase neural connections like fertilizer on the brain
• Whether memorization has a place in learning anymore, or simply a barrier to true understanding
• The truth about “learning types” and how identifying as a visual or auditory learner might be setting yourself up for failure.

...and a whole lot more.

If you want to be the most efficient learner you can be, and have more fun doing it, you won’t want to miss this discussion.

***

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Today, I’m joined by speaker, international executive and five-time author Margaret Heffernan. We discuss how to get the most out of our people, creating a thriving culture of trust and collaboration, and how to prevent potentially devastating “willful blindness.”

***

As former CEO of five successful businesses, Margaret Heffernan has been on the front lines observing the very human tendencies (selective blindness, conflict avoidance, and self sabotage to name a few) that cause managers and sometimes entire organizations to go astray.

She has since written five books and has spoken all over the world to warn, educate and instruct leaders to not only be aware of these tendencies, but how to weed them out of our companies, our business, and even our relationships.

In this conversation, we discuss many of the concepts she shares in her books, namely:

• How to tap into the collective knowledge of your organization so problems are solved quickly, efficiently, and cooperatively.
• The strange experiment Margaret ran to build “social capital” in one of her early businesses that transformed the way her employees treated and interacted with each other
• How to build a culture that doesn’t create in-fighting and unhealthy competition within your organization, and how many companies today are missing the mark
• One simple thing you can do as a leader to increase the buy-in, productivity and overall satisfaction of your team members (and it takes less than 30 seconds to do.)
• The dangers of binary thinking and how Margaret catches herself from oversimplifying a situation.
• Why arguing may be one of the purest forms of collaboration — and how to do it correctly.
• How to identify the environment and context where you do your best work and how to best replicate it.
• How “willful blindness” has caused catastrophic disasters in business, professional and personal relationships, and what we can do to avoid being another statistic
• The wonderful advice Margaret gave to her kids when it came to choosing a career path

And much more.

***

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When Pixar was dreaming up the idea for Inside Out, a film that would explore the roiling emotions inside the head of a young girl, they needed guidance from an expert. So they called Dacher Keltner.

Dacher is a psychologist at UC Berkeley who has dedicated his career to understanding how human emotion shapes the way we interact with the world, how we properly manage difficult or stressful situations, and ultimately, how we treat one another.

In fact, he refers to emotions as the “language of social living.” The more fluent we are in this language, the happier and more meaningful our lives can be.

We tackle a wide variety of topics in this conversation that I think you’ll really enjoy.

You’ll learn:

• The three main drivers that determine your personal happiness and life satisfaction
• Simple things you can do everyday to jumpstart the “feel good” reward center of your brain
• The principle of “jen” and how we can use “high-jen behaviors” to bootstrap our own happiness
• How to have more positive influence in our homes, at work and in our communities.
• How to teach your kids to be more kind and empathetic in an increasingly self-centered world
• What you can do to stay grounded and humble if you are in a position of power or authority
• How to catch our own biases when we’re overly critical of another’s ideas (or overconfident in our own)

And much more. We could have spent an hour discussing any one of these points alone, but there was so much I wanted to cover. I’m certain you’ll find this episode well worth your time.

***

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Michael Mauboussin returns for a fascinating encore interview on the Knowledge Project. We geek out on decision making, luck vs. skill, work life balance, and so much more.

***

Michael Mauboussin is back as a returning guest on the Knowledge Project!

He was actually the very first guest on the podcast when it was still very much an experiment. I enjoyed it so much, I decided to continue with the show. (If you missed his last interview, you can listen to it here, or if you’re a member of The Learning Community, you can download a transcript.)

Michael is one of my very favorite people to talk to, and I couldn’t wait to pick up right where we left off.

In this interview, Michael and I dive deep into some of the topics we care most about here at Farnam Street, including:

• The concept of “base rates” and how they can help us make far better decisions and avoid the pain and consequences of making poor choices.
• How to know where you land on the luck/skill continuum and why it matters
• Michael’s advice on creating a systematic decision-making process in your organization to improve outcomes.
• The two most important elements of any decision-making process
• How to train your intuition to be one of your most powerful assets instead of a dangerous liability
• The three tests Michael uses in his company to determine the health and financial stability of his environment
• Why “algorithm aversion” is creating such headaches in many organizations and how to help your teams overcome it, so you can make more rapid progress
• The most impactful books that he’s read since we last spoke, is reading habits, and the strategies he uses to get the most of every book
• The importance of sleep in Michael's’ life to make sure his body and mind are running at peak efficiency
• His greatest failures and what he learned from them
• How Michael and his wife raised their kids and the unique parenting style they adopted
• How Michael defines happiness and the decisions he makes to maximize the joy in his life

Any one of those insights alone is worth a listen, so I think you’re really going to enjoy this interview.

***

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In this episode, we get negotiation coaching from Chris Voss, former lead international kidnapping negotiator for the FBI.

***

Whether you’re buying a car, requesting a raise at work, or just deciding where to eat out with your spouse or partner, your negotiating skills will determine how pleased you are with the outcome.

Today, we have the special opportunity to learn some of the most effective tactics and strategies from a true master, Chris Voss.

Chris is the former lead international kidnapping negotiator for the FBI and author of the excellent book, Never Split the Difference: Negotiating As Though Your Life Depended On It.

In this fascinating conversation, Chris shares how you can use the same techniques that have been field tested in some of the most high-stakes, pressure cooker situations, in your daily life.

If you want to become a better haggler, a better communicator, or a better listener, don’t miss this episode. It’s packed with actionable insights you can start using today to be more persuasive and grab hold of more of what you want in life.

Here are just a few things we cover:

• What it really takes to be great at negotiating (most people approach it all wrong)
• How to keep your emotions in check in a negotiation
• The three different voices you use to connect with your counterpart and put them at ease
• How many of us “take ourselves hostage” in a negotiation and ruin it before it starts
• The biggest time-waster (and profit-killer) that plagues so many negotiations
• The main problems with traditional negotiation techniques (BATNA etc) and how they’re leaving lots on the table
• The “negotiation one-sheet” Chris uses before entering into any negotiation (and how you can use it to)
• How to use an “accusations audit” when you’re structuring winning deals (this is brilliant)
• One technique to get your counterpart to spill their guts when they’re trying to be tight-lipped. “Prospect theory” and how to use it to your advantage
• Maximizing employee satisfaction in the hiring process so you get the best talent...and keep them!
• How empathy saves time and makes you more likely to get what you want in a negotiation
• The power of deference (and when to use it)
• Chris’ go to tools that work best on all personality types, in nearly any situation
• How intentionally getting the other party to say “no” substantially increases the success rate of a negotiation

And much more.

An edited transcript is available to members of the Farnam Street Learning Community or for purchase separately ($9).

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