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You don't necessarily need to know what people are fighting about, because you want to find out what they're fighting for.
The subject is irrelevant.
This week on the show, we have therapist, author, and podcaster Esther Perel.
Her coveted advice on relationships is the centerpiece for books, her TED Talks and her podcast.
Where Should We Begin?
We talk with Esther about cultivating healthy workplaces and how to keep co-founders from having ugly breakups.
65% of startups fail because of relationship breakdowns.
Between founders.
Yes, founder conflict.
And why we must insist on more human connection at work even, and perhaps especially, amid rapid technological shifts.
We are flawed people.
And what AI is trying to offer us is a flawless reality.
And it prides itself on that.
If people are by their very nature imperfect and unpredictable, we need to help them live with that.
Before we get to my conversation with Astaire, we gathered some of our production team to try out the conversational card deck she just released.
It's a spinoff of Astaire's original Where Should We Begin?
A Game of Stories.
This new edition called Where Should We Begin?
At Work is specifically for co-workers.
The first question we pulled out of the deck is, what is your go-to emoji instead of using words?
Masha, I can tell you're itching to go first.
I actually realized that I only use emojis at work.
I don't use them as much with my Gen Z friends, but my go-to emoji at work is the high five emoji.
Hi, my name's Aaron.
I think my favorite one is the rock on emoji because it's very versatile.
That's a good one.
Hi, my name is Leetal.
I stand out as a Gen Xer because I use thumbs up, which is so boring.
And I was told by someone else younger that do not use thumbs up.
Like that's offensive.
It feels a little passive aggressive.
Yeah, exactly.
Oh, really?
I'm like, okay.
I know you hate me.
These cards are designed to deepen connections between colleagues and, in this case, surface intergenerational misunderstandings in a playful way.
I don't mean anything as passive aggressive, I swear.
Also, Brian on our team, he has made some custom emojis, which I don't even know how to do.
Like we have Johnny, which is Nikki's dog, that you can just react to things as Johnny.
How about you, Trish?
My favorite is the dancing party dino.
Yeah. which is not just an emoji, but a dancing dino emoji when something really good has happened.
I'm Jeff Berman, your host.
And I would say that talking with Esther Perel for this week's episode is most definitely worth a dancing dinosaur emoji.
You gotta have incredible talent at every position.
There are fires burning when you're going out.
Can you believe it?
Such an idiot.
And then you go back to, this is totally going to be amazing.
There are so many easy ways.
I have no idea what to do.
Sorry, we made a mistake.
But you have to time it right.
Oops.
Working out of a three bedroom apartment.
Stuff that just seems absolutely nut balls.
Ten years later, we're like, well that's just how you do it.
We haven't made it just how you do it.
This is Masters of Scale.
Esther, welcome to Masters of Scale.
It's a pleasure to be here.
I am so excited to talk to you.
What's different about work relationships from personal, intimate, romantic relationships?
I would say there's a lot of similarities at this moment, but there's also very big differences.
I mean.
The language of psychology has entered the business world and we talk about authenticity and trust and vulnerability and psychological safety in the same breath as we're talking about performance indicators.
But on the other hand, in the romantic sphere, in the personal, intimate space, people are talking about the deal that they didn't sign up for and the hedging their bets.
So it's a very interesting thing how the business world has entered the personal space and the psychological personal vocabulary has entered the business space.
It's a form of emotional capitalism is where they both meet.
On the other hand, what is unique to the workplace at this moment?
A it's global.
B it's remote.
C it's distributed.
4 it has five generations working together.
We used to have five generations living together, but that no longer happens in the West.
But we work together.
We brought in belonging and community at work.
And both of them have evolved to an identity economy.
In love, I want you to bring out the best version of myself.
And in work.
I want you to help me with my sense of meaning, my personal development, my sense of self-fulfillment, my purpose.
It's a fascinating meeting ground between those two spheres.
And why they have come to actually mirror each other in this way is another question, but it has a lot to do with the breakdown of communal structures and of religion.
The other breakdown that you allude to there in the business world is we frequently no longer share space.
And I miss the interstitial time.
I miss the walk to get a coffee and the catching up.
Ability to read body language and pick up on nonverbal.
And now we're on Zooms and by and large, we disappear from each other.
What are you seeing is working to improve communication and connection in work relationships that are primarily remote.
The first thing I would like to say is that what you just highlighted is not benign.
It is huge.
People say, well, do you think people should come back to work in person?
I say absolutely.
People should come back to work in person.
Maybe not five days, but that's not enough.
Because the people who are coming back are socially atrophied.
The people that are coming back have been de-socialized and have lost skills, and the younger ones never developed them.
And so to just come to work and sit next to you at my laptop while you're sitting at the other laptop, each one in our cubicle is not creating any connection, is not creating any different type of communication.
It's basically we are there, but we are not present.
We are in a state of artificial intimacy, you know, mediated by the devices.
Esther has just released a new edition of her conversational card game called Where Should We Begin?
At Work.
I created a first game originally during the pandemic because I thought, what am I going to do?
I'm going to talk about how people are disconnected isolated lonely, or I'm going to do something about it that I can provide.
That fits my identity.
And so I created a game thinking, what should people talk about in this moment?
How do they laugh even when things are really serious?
How do they ask daring questions without it becoming therapy speak?
People started to play, where should we begin the game of stories?
And then I began to notice that when they want to bring them at work, they would have somebody taking out the cards with the pink triangle, which were the sex questions.
The new version removes those spicy cards from the original game to make it appropriate for playing with colleagues and fine-tunes the questions based on the data-backed insights of her partner, the HR company CultureAmp.
It's a clever example of letting insights from customers lead your product development.
I bring my clinical experience and CultureAmp brings the data science, the people science that backs some of my suggestions.
So we develop together what are the four main dimensions of relational intelligence in the workplace.
And what are the best prompts that can elicit the experience of these dimensions in the workplace between two four ten, you know, large groups.
So the science gives me the confidence, backs with data, things that I sense, think about feel, have seen, but cannot deliver at scale.
And they offer that.
So it's an incredible marriage of complementarities and skills.
Can you talk to us a little bit about how the game works and some of the questions that are in this hundred card pack?
How do you envision people using it?
Maybe just before I tell you how we'd use it, I'll tell you why it matters.
The business world understood for the first time that companies with strong relational intelligence basically have a better culture.
If they have a better culture, they have a better engagement.
And if they have a better engagement, they have a higher performance.
Hmm.
That is now validated and corroborated by tons of data from CultureAmp.
At the same time, relationship skills.
For most of history in the business world have been considered soft skills.
And soft skills usually meant feminine skills, and feminine skills usually meant that you can idealize them in principle and disregard them in reality.
It was a nice thing to have, but that's not what you get promoted for.
What has changed is that relationships is the competitive edge at this moment.
It's the one thing for the time being that AI cannot compete with yet.
So there is a rush in the business world and in the tech world to compete, create cultures that have strong relational skills.
And it's skills is not even the word.
It's really a form of intelligence.
It's much richer than skills.
So it looks like this, the game.
Just so we can see it.
It's a one deck.
For folks who are just listening, it is like a large deck of cards, effectively almost like a tarot-sized deck of cards.
And then you open it like a box of chocolates.
You know, I am Belgian after all.
And then you have questions like the feedback that I wish I had heard sooner in my career.
The last time I was really proud of our team.
Now you can see in each question where you would play this.
Onboarding, offsite, team building, management, feedback session, one-on-one with colleagues.
This one I really love.
A first impression I had of a colleague that has changed.
What is the first impression of a colleague that you had that has changed?
In my own team I had a person who I thought was very kind of flat affect, terrific sense of humor dry, didn't think that.
Had a broad range of reactions and emotions until one day something happened in their family.
And I just asked, and what's happening?
And I said, you know, I am a person people talk to about this.
If you care to please let me know.
And I saw a range, an arc of emotion.
From grief to hope to sorrow to loss to fighting.
And I just thought, wow, I wouldn't have known any of this.
We could have worked another three years and I would continue to just say, great sense of humor.
Now, if you don't like the question, by the way, when you play you just say I'm not inspired by this.
I can't come up with anything.
And you move on to the next.
The goal is not to have to answer everything.
You can do it virtually.
You can do it in person.
You decide what's the best use of it.
It has multiple ways of being handled.
It feels like we had an era in kind of the mid-teens leading up to COVID, where there was this emphasis on bringing your whole self to work.
But my sense is that there's been a pullback from that.
That didn't feel great and people want boundaries and you know, come to work, do your job and go back to the rest of your life.
I'm curious one if you were seeing that, or if that is a skewed perception, and how that tension between bringing your whole self and having work-life balance, how that plays out in your mind.
I think that people have always brought their whole self to work.
It's just been unconscious.
I always say we bring two CVs the official CV that has the resume of your titles and your job, and the unofficial resume, which is your relationship history.
And that relationship history is.
It's everything about how you actually show up at work.
Relate to authority, deal with asking for help being with taking responsibility.
Deal with depending on others.
Deal with how much you think that only you can do it because you can't rely on anybody.
It's an amazing thing how people in the business world do not pay enough attention to this.
And yet we know that 65% of startups fail because of relationship breakdowns.
Between founders.
Yes, founder conflict.
I'm struck by this 65 statistic that 65 of startups that fail fail, at least in part, because of conflict between co-founders.
That's Noam Wasserman's research.
Given that, how should co-founders and how should investors who are backing co-founders be thinking about that relationship management to minimize the chance that they're in that 65 cohort?
I was beginning to be called in into these situations.
But like couples therapy, you often kind of say why didn't you come a little earlier when stuff wasn't yet completely encrusted?
You know, my colleague who created the game with me here.
We're starting a company and they went away with partners the three founders and their partners for a few days just to be together, just to get an understanding of who you are when you're not, you know, in this small circle here between you and I, or the three of us, discussing what we're going to create.
I thought that was a beautiful idea.
Tell me about your divorces.
I mean, every time I do founder workshops, the divorce stories are terrible.
Terrible.
People carry grief and rage and frustration.
And the way you ended your previous relationship is going to influence A who you're going to choose and, B how you're going to manage the next one.
So you want people to really have an opportunity to discuss their endings of previous businesses the good ones, the ones where people stayed in touch and in a good way, and the ones where people just carry with them a litany of resentments.
You know, and what about conflict?
I rely a lot on the work of a guy named Howard Markman, who actually talked about it in the personal sphere.
But what he highlighted is that you don't necessarily need to know what people are fighting about, because you want to find out what they're fighting for.
What they're fighting for is the form.
What they're fighting about is the particular subject of the day.
If the fight is that I constantly am in a power struggle with you because I think that you're putting your priorities ahead of mine, it doesn't really matter if we're talking about expansion or hiring or layoffs.
The subject is irrelevant.
People fight for power and control.
Who's in charge?
Whose priorities matter?
Who makes the decision?
People fight for care and closeness.
Can I trust you?
And do you have my back?
Will you stand up for me?
You know, what are you saying behind my back?
Et cetera.
People fight over respect and recognition.
Do you value my contribution?
Do I matter?
Is my presence meaningful?
Do I exist here?
So it's what I get and what you receive.
If you deal better with conflict, you don't just fight better, you have better relationships.
All together.
Still ahead, more with Esther Perel on how to build stronger relationships at work.
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Expanding your business in the US can feel like a maze.
Every state has its own payroll benefits and compliance rules, which can pull your focus away from growth.
That's why founders use Deal.
Deal is the professional employer organization, or PEO, that gives you a dedicated HR expert plus Fortune 500-level benefits for your team.
The National Association of PEOs says businesses can grow twice as fast if they use one.
So if you're scaling, make it simple with Deal.
Go to deel.com slash MOS and get up to three months free.
Welcome back to Masters of Scale.
You can find this conversation and more on our YouTube channel.
If someone wants to get better at this, what do you recommend that they do to build these soft skills and position themselves for this next moment in the business world?
It depends on your age.
Why?
Because a boomer has a retrofit.
A boomer has had a whole other experience of working in a different way.
A Gen Z and an Alpha experience has grown up with predictive technologies that basically tell you where to go, what to eat, what to do, and they give it to you in a frictionless, polished way.
And I am a user of them, so this is not an AI and tech, all good, all bad, seriously.
But basically, what you learn is is to have expectations with people that are based on the algorithmic perfections that you have been trained on with the machines and with the applications.
So people by definition are imperfect and unpredictable.
When you are constantly fed predictability and frictionless delivery on demand of your every delight, you become incapacitated in your ability to tolerate uncertainty unknown, unexpected frustration conflict experimentation, making mistakes, then figuring out what you can be responsible for and how to change it.
That is the crucial realm of relational skills.
When you don't practice that, then you become an avoidant.
You will create situations where, instead of having a complicated relationship with you, where I need to have a difficult conversation, I basically avoid.
I cut off, I disconnect, I cancel you, I unfriend you, you name it.
Most relationship problems are complex problems.
They're not problems that you solve, they're paradoxes that you manage.
And you manage them in a kind of a choreography.
You dance.
You know, I listen to you.
I tolerate hearing what you have to say.
That is completely the opposite of what I thought it was about.
It doesn't mean that I agree.
I realized that wow, you know, you didn't come an hour late because you don't care about what we're doing.
But in fact, you have somebody that you need to take care of there.
And I understand that your face and your sourpuss is a completely different story than what I had imagined.
And I do what Peter Senge used to talk about in terms of conflict the steps of the ladder of inference.
I observe something.
I make an assumption about it.
From the assumption, I make a conclusion.
And from that conclusion, I change my behavior.
Well, now I take my behavior and I look at the conclusion what is driving this behavior?
Which then lets me to see what are the assumptions underneath.
Then lets me see that my observation was completely subjective, which means flawed.
We are flawed people, you know.
And what AI is trying to offer us is a flawless reality.
And it prides itself on that.
So, as we enter this next era, this AI era, we're on the verge of having AI agents that represent us and engage with other people's AI agents.
And advance to the point of 98 99 percent, so the humans can come in and finish that last one or two percent.
What have you learned from the algorithmically driven world that we've been in for the last 15, 20 years?
That Sam Altman should know, that Anthropic and Google and Inflection should know.
What should they be doing differently based on what you've learned?
That's a question with a big responsibility.
I think when you have a polarization, the point is not to convince the other people that what they do doesn't work or has danger in it, etc.
Basically, when you do polarity management and that's the beginning of the conversation, Polarity management usually you start by highlighting all the great things that are coming up with machines and AI learning and biological intelligence and affective intelligence, et cetera, et cetera.
Then you go and you talk about all the weaknesses that have existed in the systems that we have known.
Then you go and talk about the weaknesses that exist in the new systems, because every system has weaknesses.
And only then do you highlight why it actually is important that, if people are by their very nature, imperfect and unpredictable, we need to help them.
Live with that.
So what do I do?
Is I create tools that they can integrate, that invite conversation, that invite exploration, that invite curiosity, because these are the most important elements that make you feel alive.
You don't just want to survive.
You want to feel alive.
You don't just want useful information.
You want curiosity.
We are embodied creatures.
I don't care that we can replicate pieces of us in a machine.
It's great.
It's fine.
That's not my point.
My point is that we are people who touch, who smell, who look, who listen, who whisper.
We have a whole sensorial world.
And that world is is essential to the fact that we are mammals.
We are not just machines.
We are mammals.
And mammals play.
Play is the most important adaptation for uncertainty.
It is the way we practice uncertainty, is by playing.
And these things have existed long before humans ever came onto the planet.
I say to them go and study biomimicry and learn about systems in nature and then see what is relevant for you in terms of the social, ecological systems in our society.
It actually shows you mutualities matter.
What I bring, what you bring, complementarity is essential to relationships.
We have had new machines throughout history, with whom we have learned to live and to do better certain things that we couldn't do before.
So if we could create a psychology of complementarity rather than of canceling out and competition, it would make a lot of difference for many, many things.
When I go to those companies, the very ones you just mentioned.
I've been to a few of them and others.
That's what I talk about.
There's a sociological framework that divides our world into three basic spaces.
The first space is our home.
The second is our workplace.
And the third is any other place where we find community.
This could be a church, a mosque, a synagogue, a barbershop, a coffee shop, a bar.
There's plenty of data to show that Americans are spending less and less time in these critical third spaces, and remote workers have mostly lost their second space.
I wanted to ask Astaire how that's affecting us.
So we lose the second space.
And now people say, you got to come back to work.
And I say, I think that's a great idea, but it's not enough to just show up.
You have to create intentional premeditated interactions.
And that's different ways of running meetings.
That's part of where the cards come in.
Start every meeting with one of these questions rather than just with, OK, who has the report?
Create sports, create opportunities to eat together, do the things that for centuries human beings have done.
That really creates bonds that allow people that are different to meet.
Because this is where democracy resides.
It's in that meso level, that space in between where you actually learn to deal with differences.
The third space the library, the neighborhood, the community center is the space where people used to come together around a shared mission with people that are different from them, which work has done as well.
And once you lose that, you lose the space where you cultivate tolerance.
And once you lose the space where you cultivate tolerance, you increase polarization and you threaten democracy.
This is not just psychological.
This is sociopolitical.
I don't have a solution.
I think I can educate about what's happening, but I can't solve it.
Does it put more burden on the romantic relationship is a different question.
And does it?
Both work and home today are carrying the burdens of a ton of needs and expectations that used to be distributed in religion, extended family and communal structures.
And all these needs have been transferred into work and into love, which are the two primary poles of our lives.
So we demand things at work that have to do with purpose and identity and meaning and self-fulfillment, and all of this, which we also demand in our romantic relationships.
And I think we need to expand.
You know, we can't use the word intimacy and love just in the romantic sphere.
It needs to really extend to friendships and to mentorship and to all kinds of other relationships that involve closeness and trust and recognition, etc.
I appreciate that you didn't set out to be as famous as you are.
And yet you are a paradigm of the ability to scale ideas, to scale your impact and your reach.
What have you learned over the last 20 years about scaling ideas and impact?
I would say a few things.
I think that psychology for a long time was tucked away.
We were not able to advertise or do anything public.
And so we also didn't participate in the culture at large.
We were not in the public square.
And that meant that other people would talk often about things they didn't know much about.
So I decided at one point that I wanted to open my office.
I wanted you to hear the incredible revelations that happened in my office.
And that was through the podcast, Where Should We Begin, which is now eight years.
It was the first therapy podcast, but not with patients.
They have never been patients, but there's enough people who want to know. participate.
And then I wanted to bring the office to the public square, which means to create with you in life events what actually happens in my office, so that you could have that experience as well.
One of the things I say at every one of these events, which I think is really about whatever being a public intellectual or a thought leader or things like that is that even when I sound very confident, I am sure of nothing.
And that is the difference of some of us.
Some people are in the public square convinced that they are right and they have the answer.
And I am in the public square sounding confident because I have to be, but that doesn't mean that I think I know.
I have it all figured out.
And so I give space for the debate, for the doubt, for the dilemma, for the complexity.
And I help articulate all of that.
But again, complex problems are not problems that you solve.
They're paradoxes that you manage.
And I've kept myself on that level.
You know, you don't choose to scale or to be recognized.
People recognize you.
And from that place, becoming relevant on a cultural level is not something you orchestrate.
Fundamentally, it's the listener who shapes the speaker.
As we sit here in the spring of 2025, we're in graduation season.
If you were standing before a group of new college graduates giving their commencement address, what's a piece of advice you would be offering them?
You know, I just did a whole conference with 2500 therapists and coaches and the likes and I had a phenomenal surprise.
At one point, I said, how many of you are in the field as a second career?
And probably half the people in the audience said So.
I would say to the young student where you start is not where you will go, nor where you will end.
It doesn't really matter where you start.
Start by finding people who will teach you to work, to think, to solve problems.
Because it's like a teacher in college.
You can be passionate about a subject.
If you have a bad teacher, they'll ruin it for you.
But if you have a subject you know nothing about and couldn't care less, but you have a teacher who can pique your curiosity, they will open an entire world to you.
So go for the teacher.
Don't go for the topic.
Go for the particular manager.
Don't go for the company.
The urgency that Esther Perel feels about preserving and improving our relationships at work is palpable, and I couldn't agree with her more.
We are losing human connection at an alarming rate, which has effects on mental health, on community civility, productivity and even democracy.
Her new card game is Where Should We Begin at Work.
We'll put a link in the show notes.
And to take us out, let's listen in on a little more of our team playing a stairs game.
I'm Jeff Berman.
Thank you for listening.
All right, next question from the game.
I will never forget my manager who... Aaron, why don't we start with you on this one?
I'll never forget my manager, who I worked at a studio as an assistant engineer, and they just never looked out for the assistants.
That place burnt through assistants.
I almost left working in the music industry.
And then, on the flip side, the studio that I worked at right after that, the studio manager was the complete opposite.
I will never forget my manager, who hated me, which I think I can pretty safely say only has happened once in my career.
You're so not hateable, Lital.
What happened?
I just failed on every front of this job.
It was my first paid internship out of journalism school.
I always disappointed her.
Masha, were you going to say something?
I had some good managers and some bad ones.
No comment.
What about you, Jeff?
I feel like you've worked for some characters.
I'll go back to when I was at MySpace and Google bought YouTube and I was given the responsibility for figuring out our video strategy.
I got a strategy approved and I asked my boss if he wanted me to go find someone to run it.
And he said, well, you're going to run it.
And I said, I don't know what the F I'm doing.
And he just stage whispered to me, no wonder.
And it was one of those profound moments in my life and great lesson for my whole career.
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Master's of Scale is a Wait What original.
Our executive producer is Eve Tro.
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The production team includes Masha Makotunina and Brandon Klein.
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Mixing and mastering by Aaron Bastinelli and Brian Pugh.
Original music by Ryan Holiday.
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