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From managing people to managing AI: The leadership skills everyone needs now | Julie Zhuo

By Lenny's Podcast

Summary

# From managing people to managing AI: The leadership skills everyone needs now | Julie Zhuo ## Key Takeaways * The fundamental skills of management—setting goals, understanding resource strengths (now including AI models), and establishing processes—are directly transferable to effectively working with AI agents. (02:36) * AI empowers individuals to perform tasks previously requiring multiple specialists, leading to flatter organizations where traditional role boundaries dissolve, emphasizing the role of "builders." (10:27) * Defining success with crystal-clear, objective criteria is crucial for both managing human teams and prompting AI, making evaluation frameworks essential. (07:11) * The core of effective management, particularly for new managers, lies in self-awareness, understanding one's own strengths and weaknesses as distinct dimensions, and managing oneself to be sturdy yet flexible. (25:33) * Feedback, when practiced consistently and delivered with genuine intent, is a critical tool for accelerating team improvement and calibrating perceptions to reality, fostering growth and better outcomes. (37:07) ## Smart Chapters * **00:00:00 Introduction and Book Re-release:** Lenny introduces Julie Zhuo, her background, and the re-release of her book "The Making of a Manager," highlighting the inspiration she provided for the podcast. * **00:02:36 The Managerial Skills for AI:** The conversation delves into how traditional management skills, like setting goals and understanding resource capabilities, are crucial for effectively managing and working with AI agents. * **00:10:27 The Rise of the "Builder" and Flatter Organizations:** The discussion shifts to the trend of organizational flattening due to AI, where individuals are empowered to do more, blurring traditional role lines and creating a need for "builders." * **00:17:42 AI as an Accelerator for Learning and Prototyping:** Julie shares insights into how AI tools are accelerating learning curves and enabling engineers and others to prototype and build more effectively. * **00:22:34 Data Analysis in the AI Era:** The conversation explores how fast-growing companies are leveraging data, the challenges they face, and the evolution of analytical methodologies in the age of conversational AI. * **00:28:44 Diagnose with Data, Treat with Design:** Julie explains the synergy between data analysis and design, emphasizing that data identifies problems and opportunities, while design provides creative solutions. * **00:33:35 The Evolving Role of Management Amidst AI:** The discussion focuses on the increasing rate of change and uncertainty managers face, highlighting the need for sturdiness and flexibility, likening it to a willow tree. * **00:41:45 Timeless Wisdom for New Managers:** Julie shares essential, timeless advice for managers, focusing on self-management, understanding personal dimensionality, and objective self-assessment. * **00:53:00 The Art of Feedback:** The importance of consistent feedback as a daily practice for team improvement and calibrating perceptions to reality is discussed, along with tips for delivery and reception. * **01:03:11 The Win-Win Mindset in Management:** The conversation emphasizes the necessity of adopting a win-win approach in management, particularly in difficult situations like team member departures. * **01:06:22 The Power of Conviction and Purpose:** Julie stresses the importance for managers to have personal conviction in the purpose and vision they are executing, even when it's not their own creation. * **01:14:28 AI Corner: Creative Uses of AI:** Julie shares personal anecdotes about using AI for creative projects, including a talking raccoon for her son and generating parody songs. * **01:17:58 Contrarian Corner: Infinity in Every Direction:** Julie shares her contrarian belief that there is infinite complexity and potential in every direction, even in mundane situations. * **01:22:44 Lightning Round: Books, Shows, and Products:** Julie recommends books, shares her limited TV watching habits, and discusses products like Cursor, the Madic robot, and the Limitless pendant. * **01:27:38 Life Motto and Future of Kids' Learning:** Julie discusses her motto "Make it happen" and emphasizes the critical importance of teaching emotional regulation to children in the age of AI. * **01:30:30 Closing and Future Collaborations:** Julie and Lenny express mutual appreciation, discuss future collaborations, and provide information on how to connect with Julie and her work. ## Key Quotes * "Management is just about in my mind having an outcome. So you want to get something done. That's the thing. You have a northstar. You have a vision and you're just trying to figure out how to use the resources that you have to get that thing done." (02:36) * "We need to dissolve the boundaries of these traditional roles. So in the past again we would have a traditional team engineers product manager designer researcher data scientist and I think now the teams can look more like well it's just two people and again they could be any of these traditional disciplines but uh the the key thing is they can now use AI to help themselves do a lot of the things that the other folks used to be able to do." (10:27) * "My big motivation to write it was, I think, largely because I felt if I had to write this thing, I was likely going to become a better manager. And that was actually a huge part of it." (04:46) * "I think today management is really about this idea of like be sturdy while being flexible." (14:30) * "Data is not a tool that's going to tell you what you should build or what the solution is or how we're going to, you know, cure the fact that you don't have really great retention. It's just not. But it can tell you if you have a problem and where that problem or opportunity might be." (28:44) * "I think all of us are of course like any human being, we have things that we're strong at. We have things that we're weak at. And I am a very big believer that every strength is its own weakness and every weakness is a strength." (25:33) * "The best way the first tip on getting feedback or delivering hard feedback is first go and actually establish that our relationship is one in which we value each other's contribution. We want to help each other grow and therefore we're going to be the kind of people that want to give feedback to each other every week." (37:07) * "My general impression for both myself, everyone I've worked with is that we don't value feedback enough or we don't kind of think about enough." (37:07) * "I think that the rate of change is accelerating and we've seen that over the last couple of decades." (13:48) * "Emotional regulation is still really, really, really important. That's probably the thing that I think about the most in terms of what I want my kids to learn." (31:37) ## Stories and Anecdotes * Julie shares how she created a talking raccoon toy for her six-year-old son using AI, inspired by a friend who had a similar AI-powered parrot, demonstrating the creative potential of AI for personalized gifts. (1:14:28) * She also describes creating an album of personalized parody songs for her middle son's birthday, using AI to generate lyrics for video game-themed parodies of popular songs, which she then records herself. (1:16:08) * Julie recounts receiving feedback that she was quiet and didn't think quickly on her feet, realizing this was the flip side of her strength in being thoughtful and deep in her analysis. (26:50) ## Mentioned Resources * The Making of a Manager: Julie Zhuo's best-selling book, re-released in paperback with new chapters on remote management and managing through change. (04:06) * The Looking Glass: Julie Zhuo's newsletter that inspired Lenny's newsletter. (01:03) * Sundial: Julie Zhuo's AI-powered analyst company. (01:31) * OpenAI, Gamma, Character AI: Companies that use Sundial. (01:31) * Mercury: A banking platform for startups. (00:07:37) * DX: A developer intelligence platform. (00:08:48) * Zen and the Art of Motorcycle Maintenance: A book by Robert Pirsig that Julie recommends for its insights on quality and change. (1:22:44) * Conscious Business: A management book by Fred Kofman that Julie highly recommends for its tactical advice on win-win scenarios and aligning work with values. (1:23:41) * Good Inside: A parenting book by Dr. Becky Kennedy that Julie recommends for its insights on relationships and sturdiness. (1:25:18) * La La Land: A movie Julie rewatched this year that she loves. (1:26:30) * Cursor: An AI-powered coding application that Julie uses. (1:26:57) * Granola: A product Julie enjoys. (1:26:57) * Replet: A coding platform Julie uses. (1:26:57) * Madic Robot: A robot vacuum cleaner with AI vision capabilities that Julie recently acquired and finds delightful. (1:27:16) * Limitless pendant: A wearable device that records and summarizes conversations, providing feedback, with Julie being a small investor. (1:27:38) * Ethan Evans' guest post: Mentioned by Lenny as a resource for a framework on figuring out what to work on and gaining trust. (01:01:52) * TikTok: Social media platform mentioned for viral content and parenting advice. (00:28:44, 01:25:18) * Twitter/X: Social media platform mentioned for sharing thoughts and ideas. (00:14:11, 01:31:09) * Alexa: Voice assistant mentioned for playing parody songs. (01:16:08) * Spotify: Music streaming service mentioned in the context of parody songs. (01:16:08) * Facebook: Mentioned as Julie's former workplace and as a place with a poster about motion vs. progress. (01:07:54)

Topics Covered

  • Management Skills Translate to AI: Understand Your Models.
  • Dissolve Traditional Roles: Everyone is a Builder.
  • Diagnose with Data, Treat with Design.
  • Be Sturdy While Flexible, Like a Willow Tree.
  • Self-Management is Core to Leadership.

Full Transcript

We're seeing this kind of flattening of

orgs. Everyone's becoming an IC again.

It used to be, okay, I don't have the

skills to do 10 different jobs, but now

with AI allows me to do many of those

jobs myself. We need to dissolve the

boundaries of these traditional roles

and call ourselves builders. I'd love

for us to get to the world where that's

the title.

I also just saw a stat Google let go of

so many of their middle managers.

Management is still really critical. You

have a northstar. You have a vision and

you're just trying to figure out how to

use the resources that you have to get

that thing done. Used to be people, but

now it's basically models and different

models have different strengths. You

kind of have to assemble the adventures

so that you can use the right tools for

the right purposes.

What do you feel is the biggest change

in the role in life of a manager these

days?

It's always been manager's job to manage

change. I just think the rate of change

is accelerating. Today management is

really about this idea of be sturdy

while being flexible. So I think about

this metaphor a lot of the willow tree.

It can survive a lot of storms,

disasters, etc. But it's also very

flexible.

You have such an interesting trajectory

from being head of design to now being

obsessed with data and analytics.

You want to diagnose with data and treat

with design. Data is not a tool that's

going to tell you what you should build.

I don't actually think a lot of the fast

growing companies are using data well at

this point. Traditionally things just

didn't grow that fast. These companies

are totally getting by on just good

instincts and good vibes. But what

always happens is eventually things stop

growing.

Today my guest is Julie Zoo. Julie was

my first ever guest on this podcast

which I recorded over 3 years ago. So

this is a very special conversation. As

I've shared many times before in other

places, Julie's newsletter, The Looking

Glass, was the inspiration for my

newsletter and basically led to

everything that I do now. If you're not

familiar with Julie, she was the

longtime head of design for the Facebook

app used by over 3 billion people. She's

also the author of the best-selling and

very important book, The Making of a

Manager. And most recently, she started

her own company, Sundial, which is an AI

powered analyst used by companies like

OpenAI, Gamma, and Character AI. Julie

is one of the most thoughtful and

insightful product leaders that I've

ever come across. And she's also got one

of the most interesting perspectives on

product building. Having worked at a

mega-arge corp like Meta as head of

design and now as a founder at a tiny

startup that's all about using data to

help you make decisions. It's really

rare for someone to have this spectrum

of experiences. In our conversation, we

talk about how learning to be a great

manager directly translates to learning

how to use AI tools extremely well.

Which specific skills will become more

valuable in the next couple of years?

Her most valuable and timeless advice

for new managers, why she's not hiring

product managers at her startup, her

simple heristic for knowing when to use

data and when to use intuition in making

decisions. There's something in this

episode for everyone. And if you enjoy

this podcast, don't forget to subscribe

and follow it in your favorite

podcasting app or YouTube. It helps

tremendously. And if you become an

annual subscriber of my newsletter, you

get 15 incredible products for free for

an entire year, including lovable,

replet bold nad linear superhuman

descript, whisper flow, gamma,

perplexity warp granola magic

patterns, recast, chappd, and mobin.

Head on over to lennisnewsletter.com and

click product pass. With that, I bring

you Julie Zoo. This episode is brought

to you by Mercury. I've been banking

with Mercury for years and honestly, I

can't imagine banking any other way at

this point. I switched from Chase and

holy moly, what a difference. Sending

wires, tracking spend, giving people on

my team access to move money around so

freaking easy. Where most traditional

banking websites and apps are clunky and

hard to use, Mercury is meticulously

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ways that you use money into a single

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entrepreneurs love about Mercury. Visit

mercury.com to apply online in 10

minutes. Mercury is a fintech, not a

bank. Banking services provided through

Mercury's FDIC insured partner banks.

For more details, check out the show

notes. Today's episode is brought to you

by DX, the developer intelligence

platform designed by leading

researchers. To thrive in the AI era,

organizations need to adapt quickly. But

many organization leaders struggle to

answer pressing questions like which

tools are working? How are they being

used? What's actually driving value? DX

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leaders need to navigate this shift.

With DX, companies like Dropbox,

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productivity. To learn more, visit DX's

website at getdx.com/lenny.

That's getdx.com/lenny.

Julie, thank you so much for being here

and welcome back to the podcast.

Thank you, Lenny. I'm so excited to be

here. I've been looking forward to this

all week. I love your podcast. I love

where you've taken it since our very

first conversation, and I'm super

excited to have a fun and engaging chat.

Can you believe that first episode, the

very first episode of this podcast was

over three years ago at this point. Holy

I'm not sure you had that fire in the

background back then.

So, funny enough, I don't know how many

people have noticed this Easter egg that

I've stuck with. Uh, in that first

studio, I was just watching the episode.

I had like this funny little mirror. I

don't know if I had in the first episode

with a fire uh place that was showing up

in that mirror because the mirror was

showing something stupid. And so I've

just kind of kept this fireplace across

every studio I've moved across in my in

my various places.

I even remember when we chatted video

was like kind of a newer thing. You're

like we'll record it but like it's

really about the audio and now we moved

into the video era.

So as you were saying that I realized my

fire was broken so I just had to turn

that on. So we just cut a little piece.

Uh yeah that fire was my little fun

Easter egg for myself and I I don't

think anyone's ever realized this.

It's very cozy. I love it.

That's the idea. Uh, I was actually just

looking at the stats. So, since that

first episode, this podcast has done

over 20 million downloads. It's

approaching 30 million downloads.

It's really incredible. I think it is a

testament to just your curiosity and how

much you really care about the craft of

building great products and sharing that

with the world. And I know I listen to

your podcast and read your newsletter.

My team does. We're constantly sharing

things from all the amazing speakers

that you've had. So, thank you for doing

this.

Uh, my pleasure. I really appreciate

that. So, the reason we are chatting

again three years later is uh you're

re-releasing your incredible book, The

Making of a Manager. I've got it right

here. Uh you've sold a bazillion copies.

It's been on every list I've seen. Uh

you're releasing the paperback version.

You're adding some chapters. I guess

first of all, just how do you feel on

the reflecting back on the the success

of this book?

It honestly went beyond my expectations.

So, I'm super happy with it. My big

motivation to write it was, I think,

largely because I felt if I had to write

this thing, I was likely going to become

a better manager. And that was actually

a huge part of it. Um, because thinking

about and writing something, you know,

I've been blogging for a long time and I

know that part of my process is when I

really sit down to try and put down

everything I feel and write letters to

myself, it really helps me. And so that

was honestly a huge motivation. I hope

that it would go out there and it would

sell some books. I was thinking about

that maybe for people who grew up in

companies like mine like Facebook, you

know, high-scale Silicon Valley, it it

might resonate. I couldn't have expected

that it would have much wider reach than

that. And um and that's been really

awesome. And just how many people will

tell me things like, I thought I was the

only one who felt this way, but this

book made me realize that, hey, these

are very normal feelings. And that's

certainly how I felt just stumbling

through and feeling like an imposttor

for so many years. And so I'm it really

is very gratifying to hear that from

readers.

I feel like it's the modern-day high

output management. It feels that's the

book that's been mentioned most on this

podcast. And it feels like this is just

like a modern version. I feel like that

date book is actually out of date in a

lot of ways. So I can see why people are

really drawn to it. And this is a great

segue to the first area I want to spend

some time on, which is it feels like a

lot of the skills you learn as a manager

translate to being really good with AI

and using AI tools really well. And I

want to talk through a few trends that

uh I want to get your take on that

relate to this general theme. The first

is it feels like just everyone is going

to become a manager in the near future

because of agents being so integrated

into our workflows. there's this agentic

society that we're that we're coming to

and it feels like the same skills of

being a manager make you really good

working with agents. Uh just thoughts on

on that and where you think that's going

to go.

I 100% believe that and agree with that

which is that management is just about

in my mind having an outcome. So you

want to get something done. That's the

thing. You have a northstar. You have a

vision and you're just trying to figure

out how to use the resources that you

have to get that thing done. And

typically when we talk about management

in traditional settings, we talk about

the resources being people and getting

the right talent and making sure that

there you know you've got the like

assemble the adventure. So you've got

the right mix of skills that you need.

The second lever is around okay what's

the purpose? Does everyone know what

they're supposed to do with their

talents? Like do we have a goal? Do we

have a purpose? And then the third thing

is process which is how should all of

these different people and tools come

together. And these are still the

fundamentals of working with agentic

systems. Like you still need a goal. You

need to be very clear about what the

outcome is. And you have to understand

the strengths of of you know used to be

people but now it's basically models and

different models have different

strengths. So it's like they have

different personalities and so you kind

of have to get to know it like um you

know develop an intuition for it so that

you can use the right tools for the

right purposes and I mean we talk about

agents but we also talk about like what

are the tools that agents have access

to. So you still have to make decisions

around that and then there's of course

process which is how you do it. Now, now

I think with better and better models,

perhaps the agents get smarter so they

can deal with um higher and higher

levels of figuring out how to do

something, but I think it's still very

important for us to be able to provide

the right context, provide the right

highlevel instructions so that we get

what we want. So really, it's the same

principles. Uh and I absolutely agree

with you that more and more of us are

going to have to double down on these

skills to be able to use these tools

very effectively.

So along those lines, I have your book

right here. You have this list of a

manager's job is to build a team that

works well together, support members in

reaching their career goals, and create

processes to get work done smoothly and

efficiently. Uh, which is basically

exactly what you just said.

Interestingly, that middle bullet is the

part you don't have to worry about

anymore with agents. You don't have to

worry about their career development and

progress. And

that's true. That's true. Uh, though

some people do joke that if we don't

treat our agents nice, what's going to

happen when AGI comes? And, uh, you

know, maybe it's still it still might

benefit us to be kind. I'm one of those

people that says thank you to the Whimo

when I leave and just like thanks uh

chatbt when I'm in voice mode. Just like

thank you that was really helpful. So

along these lines, I know there's a lot

of ways to go here, but just in terms of

skills that are important to a manager,

which do you think are most valuable to

develop in working with agents in AI

systems? I think about things like

clarity, communication, just like what

comes to mind when you think about like

here's the things you want to double

down on as you're learning to be a

manager that will also help you be

really good at AI tooling and working

with agents.

Like the first is defining the goal and

defining the outcome and being really

really crystal clear on what does

success look like. I mean there's

obviously lots and lots of like if you

ask a company to do this we'll know that

this is challenging for humans right I

think a lot of times when you talk about

you know why is alignment so difficult

at a big company it often comes down to

this question which is different people

may have different pictures of what

success looks like and even if I

describe in human words oh you know

Lenny I want to build this product and

it's going to be amazing or this podcast

episode which you asked me I want lots

of people to hear it and take away

things that's very general like how do

we get even more specific so that we

know without question whether we've hit

it or not. This is actually a really

really difficult problem. It's a

different difficult question for us

because again we tend to think very high

levels. So figuring out how to boil it

down so that an agent can really

understand what success and failure

looks like is a lot of the game. And I

think this also relates to things like

well that's why we have to write eval

and that's why they're so important

because they're helping us understand

what is the objective criteria and these

days I work in data and my company is

all about trying to automate data

analysis and the forever question goes

the whole point of data and the whole

point of metrics and KPIs is we're

trying to put a little bit more of an

objective measure or get as crystal

clear as possible about what success

looks like and I think it's really an

art more than it is like a science. But

that's like the first thing I think if

you're really unclear about what success

looks like the prompt, you're probably

not going to get the most amazing work.

Um I think that's true for managing

teams and it's very much true for

managing AIs.

Okay. So let me actually flip this on

you and talk about another trend that

we're seeing which is this kind of

flattening of orgs. Uh managers being

let go. Everyone's becoming an IC again.

I just had the CEO of Air Table on the

podcast and his his whole shtick was

that CEOs have to become IC's again.

They have he's coding more than he's

ever coded again and his feeling is you

have to know what's possible by being in

the weeds in order to figure out what

your product should be. I also just saw

a stat that Google let go of so many of

their middle managers of smaller teams.

It's just like this flattening trend.

So, do we even need managers? I guess is

one question in the future. and then

just thoughts on how this uh will play

out.

Yeah. So, I think the real promise and

magic of AI that we're seeing in the

workplace is that it leads us to each

individual is far more empowered. So, it

used to be okay, I don't have the skills

to do 10 different jobs, so I need to

supplement by hiring people to do these

jobs. I need someone who's really good

at design. I need someone who's really

good at coding. I need someone who's

really good at data analysis. and then

I'll assemble that team. But now with AI

and my companion, it's like, wait a

second, AI makes allows me to do many of

those jobs myself. Now, I'm not going to

do them at the it's called the PhD or

the highest 1% 10% level, but if I was,

you know, at the zero or 10th

percentile, it can certainly get me even

today very quickly up to like the 60th

70th in terms of um what the state of

the art is. And I think that that

unlocks so many doors. And so the main

thing that I felt so excited about and

this is something I tell my team all the

time is we need to dissolve the

boundaries of these traditional roles.

So in the past again we would have a

traditional team engineers product

manager designer researcher data

scientist and I think now the teams can

look more like well it's just two people

and again they could be any of these

traditional disciplines but uh the the

key thing is they can now use AI to help

themselves do a lot of the things that

the other folks used to be able to do.

So, in some ways, we can drop all of

these different role distinctions and

call ourselves builders. I think that's

sort of the most general purpose way of

thinking about what we can all be. We

can all be builders. We can all be

builders. And I I I'd love for us to get

to a world where that's just that's like

the title. That's funny. That's the term

I've been actually using more and more.

I used to orient this podcast as a

newsletter around product managers and

then I started using just product to be

a little more broad and now I'm actually

using that term builder. Uh uh so and I

and I love that term because because

it's exactly what you're saying and this

is very much a theme that comes up often

in these conversations more and more

just the lines are blurring. I'm curious

at your company how does that look like?

What are you doing differently? What are

you seeing in on the ground within your

company that maybe would be different

from a few years ago?

So we have eliminated

more roles. Um for example we thought

trai we would need a bunch of product

managers. It's turned out that actually

um if you don't have a product manager,

I know this might be going against a

little bit of the ethos of of where

here we go.

Where Lety started, but I find that

sometimes when you have like a designer

or product manager and let's say I'm an

engineer, then when I have a problem

like, oh, I need to figure out the

product definition, my default will be,

well, I've got these people and that's

kind of their job description, so I'm

just going to delegate that to them. And

I think that in in doing so, you know,

again, where we want to be polite, we

want to respect everyone's lanes. I

think that's a missed opportunity for

that, you know, if I'm the engineer to

look be like, wait a second, I should

probably focus a lot too. Like I need to

understand and have an opinion about

what to build or what the user

experience is. And so we found that if

we actually make teams smaller and we

kind of even like in the past, you know,

prei like just have fewer of these, it

allowed everyone to be like, oh wait, we

don't have product manager on the team.

Okay, so communication's up to me.

Figuring out how we get greatest value

to users is something that is now

strictly in my charter. And so that's

why I'm such a big fan of like we can

make teams smaller and we can eliminate

these lines. Sure, again, there's still

I'm not trying to say like everyone has

to do everything. We still can respect

the fact that you might be much better

at this particular skill than me, but

it's less about the role and it's more

about the specific context that we're

in. And I find that whenever you have

teams and you empower them to be able to

take more action on their specific

context rather than having these higher

level rules or policies or like this is

how it's supposed to be then you get

better work, you get faster work uh and

you get happier employees because you

know people feel like they actually can

you know have the power to create the

thing that they want. That's really

interesting that just that constraint of

not having a PM makes the engineer

realize they're not going to wait for

someone else to do it. They have to

figure it out. The obvious kind of trick

there is they have to be good good at

this.

It's a very different job from

engineering to be really good at

articulating here's the problem we're

going to solve. Here's why it's

important that we're solving. Here's how

we're going to prioritize everything

we're thinking about. Here's how do we

get alignment? Is there something you do

differently when you're hiring these

engineers knowing you're gonna probably

not hire a PM and and just that feels

really hard to hire for someone that's

really good at all these things?

It is true. And I'm not trying to say

again that everyone needs to be good at

everything. I don't think that's very

realistic. I do think for example, if we

were going to create a team and we're

going to have uh a couple engineers and

none of them are very good at at

thinking through product requirements or

what the user angle is, we probably do

need to supplement the team with

somebody with that skill set, right? And

that might be a designer or that might

be another engineer who's really good at

that or that might be uh you know a a

traditional product manager or some or

even sometimes a data analyst who's

really good. So that skill is still

important and the team still needs to

have that skill otherwise it's probably

not going to produce the best outcome.

But I like to think of it as like what

are the skills that are needed for this

and can we now find a couple people but

it doesn't mean we just automatically go

to that script of need a PM need a

designer need three engineers need need

that you know um another example for us

is like even thinking about frontend

backend engineering and used to be like

oh some people are front end engineers

from a back so if you have a project and

it's got some front end some backend the

shortcut is like I need one of these and

one of these and that's how it's going

to go but if you say look you're an

engineer you're a builder You can this

has a little bit of front end but you

know what you can probably figure that

out like use AI to help you figure it

out you know get obviously someone who's

a specialist to review the code or to

give you um some highle guidance on

things but just do it and ever since we

started to implement that as well we see

yeah again a little bit of um you know

you have to kind of invest a little bit

in the beginning so people are are not

as comfortable they have to learn so you

initially things take longer takes a

little bit of extra time Right? Versus

if you did slot in a front-end

specialist and this is a front-end

project, it probably would have gone a

little bit shorter. But in the long run,

that investment really pays off because

now you have a lot more people who are

again a little more well-rounded and can

take on many more pieces just on their

own. And then in specific scenarios

like, oh, this is super front-end heavy.

Sure, let's still bring in somebody who

is more specialized in that particular

skill. I love that you've had the

experience of working at a mega large

company at Meta and now you're building

your own startup that's small and in the

middle of this trend of just staying

very small and and staying really lean

and just everyone doing more things.

It's so cool that you're experiencing

that. So, a couple questions there. Just

which functions are you seeing most

accelerated with all these AI tools? Is

it engineering? Is it something else?

And then are there are there tools that

have been most helpful to you? Just AI

tools for folks would be like, "Oh, I

should check it out." Like I'm guessing

cursor, but curious if there's anything

else.

Yeah, certainly engineering. Engineering

is one that we I mean most of our

company is engineers. So that's the one

that we focused on a bunch. I certainly

do see more people also prototyping

things. And so it's not just we have not

we have like two designers, but we also

see engineers. Um we have one uh we have

a team that's called product science

which is this interesting blend of c

it's you can think about as like a

forward deployed person who is uh has a

lot of data analysis background um and

is kind of playing a customer success

role and also kind of playing like a

product role um and you see them

starting to take on building more

prototypes or getting into some of the

engineering. And so it's really lovely

to see that blend of everyone can do a

little bit of everything else and we're

all encouraging each other. Um the other

thing that recently we've we've also

been trying to do a lot more is just you

know obviously we say hey engineer now

you can do analysis and their first

thing is like oh I don't really know

analysis. This is where chat GBT comes

in and it's like well you know

traditionally we would say well I have

to learn that from a human. I have to

ask this person and now I'm going to

take a bunch of their time because I

want them to explain everything to me.

And in fact, I think these days, you

know, TAGBT or these other AI tools are

better teachers. Um, I find that we tend

to maybe not use them quite as much, you

know, just for the purposes of

accelerating our education or or even

going through something like sometimes

what I'll do is I'll find a curriculum

online and u, you know, if you like take

a course, it'll be like this whatever

12-week curriculum and I'll just feed it

into chat PT and I'll say help me

customize a program for me, you know,

using the ways that I like to learn.

Like I am a person who really needs

examples. I need a lot of like explain

like I'm five, give me an analogy. And I

know some other people on my team,

they're like I don't get like these

examples don't make any sense. Like

we've we're different types of learners.

And so the idea of like a a you know a a

tool that personalizes learning for each

of us really helps us I think accelerate

and and just learn these skills much

faster than before. So yes, the tools

are great. We can use cursor. It helps

us. It autocompletes. It writes a bunch

of things. But the acceleration of

learning I think is another maybe

underutilized tool in all of our

arsenals just because I know whenever I

talk to people we just we forget like we

don't we don't think that like oh wait

yes we could be doing that and just

sitting down and probably in 30 minutes

or an hour learn so much faster than

what we used to be able to do before.

That's such an interesting point.

There's like these tools that are in the

just in time helping you move faster and

then there's but you also need to learn

how to do something. Yes. Like to some

foundational lessons. Uh what's an area

that your team did that like what did

they work on learning?

So I'll give you an example. I was just

talking to an engineer this morning and

he's written a bunch of these

algorithms. So one of the things our

company does is we're trying to automate

data analysis. So one of the things we

have to do is obviously understand the

best practices like if there's a type of

question hey what features are are

really the ones that people pay for we

need to kind of figure out what is the

right analysis to do and so the engineer

was saying to me you know Julie I feel

like I really understand the how like I

know the algorithms I know we do root

cause analysis like how we do that but

what I don't really understand is why or

when this would be most useful like in

what context text in a company would

this company come up because he's an

engineer. he hasn't done that job of

being like a PM or an executive that

asks these types of questions and that

was like the perfect thing where like

yeah you know traditionally you might

have asked someone but this is more

general purpose like there's so much

resources in the world on the internet

about it this is like the perfect type

of question where if you just talk to

chat GBT it's probably going to give you

a much better answer and allow you to go

deeper and a secondary thing we we've

been learning too is this idea of almost

like as a uh using chatgbt it's like you

test your learning so it explains a

bunch of things and so what I often like

to do is like okay I read this so this

mean try to explain back what I heard

right so does this mean is the right way

to think about it that this is kind of

like this analogy and chatbt will

critique me yes that is right or no you

didn't quite get that right like in fact

and it always tries to say it nicely

this is a funny part like that's close

and then eventually it's like you were

completely wrong just in in the the

style but like it it helps so much

because it It's in interactive and so we

can really test whether we really

understand the concept by trying to

retell it back in our own way.

It's incredible just how many ways all

this AI

breakthrough is helping us in advance

and do more and learn more and become

better. I know there's some downsides

but this is incredible and so many ways

of getting better and faster. I want to

spend a little more time on this data

analysis stuff. So again, you have such

an interesting trajectory from working

at a big company to starting your own

small company. Uh from being head of

design to now being obsessed with data

and analytics. So let me spend a little

time there. Um what do AI companies that

are have kind of figured out how to use

AI for data analysis and data work doing

differently? What can people what are

people missing and sleeping on in terms

of getting better at working with data?

And let me just ask add this point. I

feels like we're almost working through

here's all the blockers to a team moving

forward. There's like a waiting for the

PM to write the PRD and then there's

like waiting for the data scientist to

give you answers analysis. So this is

like another really cool unblock that

every team member will have.

So your first question was how are a

bunch of AI companies using data. So the

funny thing, my funny answer to this is

I don't actually think a lot of the fast

growing companies are using data well at

this point. And the main reason why is

because traditionally things just didn't

grow that fast. And so you know if you

got to 100 million users, your company's

probably been around for a while. And if

your company's been around for a while,

you've had time to set up things like

logging and you've hired a growth team

at that point and you've hired a data

team and they've like done a bunch of

work to log and instrument and then

transform the data and like we've talked

about like what is the observability for

our business and you just usually had

years to build and develop that because

of the the rate of growth. And so today

we see companies that are growing insane

and they're still about 10 people or two

people or however many people but

they've got hundreds of millions in ARR

and hundreds of millions of users and

you know what they don't actually have

all of that infrastructure that logging

and all to be able to truly do data

analysis. So it's I would say that these

these companies are are totally getting

by on just good instincts and good

vibes. And we see that, right? Like you

don't really need um a data analysis to

sometimes make something that works. But

I think what data helps us do is it just

it it in my mind it's it sort of is like

helping us reflect back what is really

reality. And so of course if AR is

growing, awesome, you know, great, keep

doing what you're doing. But what always

happens is eventually things stop

growing. Growth does not happen forever.

And usually when grow stop grow stops

everyone has this question of like

what's going on why did it happen and

then you start to be able to see the

power of if you've obs if you've

instrumented everything very well and

you have a very good observability model

for your business it's much easier to

start to get into the root cause. It's

easier to even predict whether growth

will slow down at a certain point. it's

easier to catch these trends earlier. If

you don't have good observability over

how your business runs and what the

company's um key levers are, then you

will be scrambling. And at that point,

that's usually when people start

investing a ton in data. So, I wouldn't

say that we're do a lot of these hot

companies, you know, are are quite there

yet. But what I also think is a trend is

that every time there's a new

technological shift, we actually have to

change the way that we think about anal

like analysis has to answer the

questions that we have. And if

technology changes or context changes,

we need new methodologies of analysis.

So for example when mobile came to the

forefront right looking at sessions or

sessions per day or or um time spent on

mobile or um you know kind of uh length

of sessions became something that was

important for us to understand are

people getting value in this new medium

I think that's the same with what we

have today conversational analytics is

totally different used to be let's say

in the Google world right I knew you

were interested in shopping if you click

the shopping tab I know you're

interested in maps if you click the maps

tab, we can measure clicks. Today, it's

just all conversation. And so, it's

actually harder for us to tease apart

what is the user intent. You know, if I

worked on um any of these LLM, uh I

would say like one of the probably the

biggest questions is, hey, what use

cases are growing or what use cases are

shrinking? And that's much harder to

tell today because it's not just clicks

on tabs or pages. It's like we have to

probably use an LLM to or a machine

learning model to bucket user intent. We

probably have to ask questions like is

the flow going really well in

conversations, you know, like a like if

I just ask one question and I don't go

back and forth like did the user get

value, right? It's always trying to get

back to like we're trying to figure out

if this was a good experience, but now

it's it's like we need to actually

invent new methodologies to help us

analyze that. Yeah, I think there the

question is always uh like with

conversations, do you want it to be a

long conversation? Do you want to be a

short convers like what's the right

answer? What's better?

I had uh the head of chat PT on the

podcast, Nick Turley, and turns out one

of the uh ways they found the most

common use cases early on was watching

uh Tik Tok comments and things going

viral on Tik Tok after they launched.

About that.

Yep.

Okay. So I want to come back to this

really interesting uh unusual path that

you took from uh being a head of design

at Facebook. Uh you're an inspiration to

so many designers. Now you spend your

time on on a data startup obsessed with

data. Uh I don't know classically

designers aren't the biggest fans of

experiments and data and making

decisions based on data. When you look

at designers and you hear designers kind

of push back on like no we don't want to

be super data driven. and we want to uh

we we know better than we have a sense

of what's beautiful and great and

intuition all these things. What what do

you think designers are are missing when

when they feel that and say that when

they they're afraid of writing

experiments and data and kind of want to

push that out?

There's one phrase that my co-founder

and I would always discuss with us uh

amongst ourselves very early on and

which we shared with like a lot of the

companies that we work with which is

what you really want is you want to

diagnose with data and treat with

design.

So data is not a tool that's going to

tell you what you should build or what

the solution is or how we're going to,

you know, cure the fact that you don't

have really great retention. It's just

not. But it can tell you if you have a

problem and where that problem or

opportunity might be. But you still need

to go back and undergo a very creative

process to figure out what's the best

way to solve that. So that's the first

thing I would say is this framework of

like data helps you figure out what's

actually happening. what do people like?

What are they engaging with? What not?

Right? It's just it gives you a story

that better reflects re reality. Um

because again, we all have stories,

right? We're like, "Oh, my my company's

amazing. People love us." Blah blah.

That's story I want to believe. But

reality may be a different picture. And

so what data is trying to do is capture

reality. And by the way, I don't think

of data just as like it's AB test and

it's quantitative things we can measure.

It's to me data is also well what did

people put onto Tik Tok and which things

went viral and what are they saying in

the Twitter verse or Xverse I guess is

what it's called now

and uh um and and what are you know and

if you do a customer interview like what

like that's still all data it's just

that that is you know a little harder to

distill and quantify although now with

AI you know we better better tools for

synthesizing so that that's all data in

my mind and it's just all trying to help

us understand what is really happen what

is the phenomenon that's happening in

reality and how do we understand it you

still have to go and invent and create

and dream and there's no formula and

there's no science that will tell you

exactly how you're going to make a hit

um you can experiment which is allows

you to try more things maybe and um and

more rig rigorously understand what that

does in the short term you're going to

have to it's all very contextualized

right because it tests don't tell you

what will happen in the very long run

and That's still get again that's all

still data you still have to synthesize

and figure out what to do. So that's

this thing I'll say diagnose with data

and treat with design. I think the

second thing I will usually talk tell

designers about is I find that sometimes

and maybe it's the let's call it the uh

false precision of numbers that we kind

of fall into, right? Because it's like

okay we got these numbers and the

numbers go up. It's like no, the fact

that you still have to choose which

things you look at is an art, not a

science. And your interpretation of if

the number went up 5%, is that good? Is

that not good? Is also an interpretation

and is an is an art, not a science. It's

just that sometimes I think we can give

ourselves this feeling and I get it like

we sometimes there's this instinct to

want to control things and we want

everything to be button up and we want

to know that if we did ABC everything

will be great. our career is going to be

awesome. Our product's going to rocket

ship. And I think designers are rightly

often pushing back and saying, "No, the

reality is like this stuff is ambiguous

and there's uncertainty and we can never

know for sure." And I think all that is

quite true. So the other thing I would

say that I really support is like you

just actually can't make a really great

product by thinking you can AB test your

way into it. So that's I fundamentally

believe that. But I don't think we

should throw the baby out with the bath

water. I think there's actually, you

know, these it's not either or. It's not

like data or design. It's like these are

just tools for us to use. And I would

say every amazing designer that I've

ever met is absolutely obsessed with

trying to get a better understanding of

reality. They want to know what users

really think. They want to know what

they're really doing. if they could read

every user's minds, that's like the the

thing we would all want, right? As a

designer is like, if I could just know

what everyone is thinking and feeling

every time they used it, my life would

be a lot easier because then I would be

able to build better and better things.

And so that's what it's trying to help

us do. It isn't perfect. No metric is

going to tell you whatever ever we hope

that it can in terms of the the true

certainty and precision, but it doesn't

mean we can't use it to better our our

product development.

I was going to say exactly what you just

said, which is every great designer that

I've worked with was obsessed with data

in the most leaning into the data versus

designers that are just like, nah, I

think I'm going to I have a sense of

what's right and why why would we let

that tell us what to do? And to your

point, it's not going to tell you what

to do. It'll tell you where

opportunities arise. Let me take us back

to the management chat and maybe just

let me ask something broad. What what do

you feel is the biggest change in the

role and day-to-day work and life of a

manager these days with the rise of AI?

I think that managing change, it's

always been manager's job to manage

change and there's always the chaos of

what's going on. I just think the rate

of change is accelerating and we've seen

that over the last couple of decades.

And so I find that there's just a great

deal more uncertainty that people have

about things like we all you know where

is AI going to be in two years from now

I don't know who know who really knows

right and so you know are we going to

have AGI in 5 years that kind of changes

a lot about the landscape not to mention

I think there's quite a lot of fear that

many organizations are feeling you know

it's like if my career has always been

in design and now these tools are

getting better and better at what I'm

doing, then holy what happens to

my career and my future and do I need to

pivot? Do I need to learn different

things? And so, it's this change. It's

this feeling of uncertainty. And I think

a lot of times managers have to deal

with that in addition to what you were

saying before, which is they also have

to learn these new skills, which is

managing AI and managing kind of like

these more powerful tools in their

arsenal of trying to get things done. So

that is very different I think than

maybe you know 10, 20, 30 years ago. Um

and so I think that the skills that

become more important are obviously

communication feedback compassion but

just being able to work with humans and

to have them understand that like yes,

we are in a state of change. I think

every leader has to do this now. every

startup founder that I know, every CEO

is how do you land this message that

things are changing and we need to be

very like we need to be very open to

change. If we go and stick to our old

ways, we're probably going to get left

behind. Uh our product's going to get

left behind. Even our way of doing

things is going to be left behind. So,

we need to change, right? We we need to

change our product and we need to change

the way that we work as we all talked

about in terms of smaller teams, more

nimble, blah blah blah. Um but at the

same time it's like how how do we do

that in a way that doesn't just freak

everyone out and it's like ah it's chaos

everything's changing like so so I think

about this metaphor a lot of like the

willow tree which is like the willow

tree is a very sturdy tree you know it's

um it's it it can survive a lot of

storms disasters etc but it's also very

flexible like the branches are very very

flexible and that's in some ways what

allows it to be very sturdy so I Think

today management is really about this

idea of like be sturdy while being

flexible and that is a very hard thing

to pull off but I think that's like at

least when I even go into be like like

be like the willow tree Julie just

imagine the willow tree and like try and

channel that as as the the kind of

feeling of of what it is that we're

trying to do together.

This reminds me of a couple things from

other guests. Uh I had Mark Beni off on

the podcast and I asked him just how do

you deal with all this change? Things

are it's like agents now. It was uh I

don't know a there's a GI coming as you

said just like how do you survive

through this and his advice is just he's

like I'm always just like good this is

great I I this is what we want this is

exciting we have so much opportunity

it's just not boring we can always

reinvent and he's always embracing what

this is good and I just I'll never

forget the way he responded to that

I think if you don't think it's good

it's kind of a painful way to live it'll

be very very difficult over these next

So, I do think that it all things be

equal, lean into it. Like, if you can

wake up every day and see it as

opportunity and excitement rather than

fear. Again, they're all flip sides of

the same coin. But I think if we can

lean more into what could it be while

recognizing that the other side does

exist and it's still there. And I think

if managers who try to pretend like it

isn't there, like it's all good, no

one's upset, etc., But there's something

also missing about just addressing and

being able to be like, "Yeah, it's hard.

Change is hard. We're probably going to

get upset. We're going to have some

chaos. Like, this is going to happen,

but we will work through it because

we're going to be flexible and we're

going to be able to put our eyes on the

big picture of what is possible, which

is exciting."

There's another quote that stuck that

kind of came up as you were talking. I

forget who it was exactly. Maybe Kevin

Wheel, maybe Mike Kger. They said that

this is the most normal things will be

ever.

Like it will only get weirder.

And I think giving people that sense of

like, okay, just enjoy this normal

because this is going to be only weirder

because we'll at least give people an

expectation, real expectations of where

things might be going.

Yes. Yes.

What a time to be alive.

What a time.

Okay. Let me uh zoom out even further

and chat about I want to ask you just

outside of AI management in many ways is

unchanged. It's still a lot of the same

work managing people helping them be

successful producing great work. What

are just some of the I'd say maybe most

timeless most important uh lessons that

you think managers especially new

managers still don't totally understand

need to hear more. What are just some

that come to mind and then we'll see

where this goes.

The first thing that comes to mind is

the importance of managing yourself and

understanding yourself. This was chapter

five of my book. It's called managing

yourself. In fact, when I wrote it, I

kind of wanted to be chapter one. And

then my publisher was like, well, maybe

you should get into some of the tactical

like people don't necessarily think

managing other people or managing team

starts with them. But I really do

fundamentally believe this because I

think all of us are of course like any

human being, we have things that we're

strong at. We have things that we're

weak at. And I am a very big believer

that every strength is its own weakness

and every weakness is a strength.

There's no such thing as you're going to

somehow, you know, get every dimension

to be 100%. In fact, I think one of the

most interesting concepts that we can

like or frameworks for myself and also

even this is also kind of like a data

frame concept is this concept of

dimensionality. So what dimensionality

means is like you're a human being but

we can kind of look at you in infinite

dimensions. There is for example how

good is Lenny at throwing an axe? That's

one dimension. There's

pretty good.

How good is Lenny at uh being a podcast

uh moderator? Fantastic.

So so okay, thank you.

How good is Lenny at doing a zero to one

type of project in the AI space? Right.

So again just you can think about these

as infinite dimensions and the reality

is each of our profiles is very unique.

It's like a fingerprint you know. So for

you it's like these are all these areas

that you're really great at you know

much better like in the top 1% and then

there's some areas we're in the top 10%

then there's some areas where you're

like kind of average and then there's

some dimensions in which you're worse

than average compared to other people.

And that's just true for all of us. And

what I like about that is therefore if

you if you take that as the model,

right? Things that then you you realize

that none of these dimensions are you

entirely. So we can be you know I can

make a comment like Lenny your ax

throwing really could use some

improvement. And ideally you're not like

Julie is saying I'm a bad person. I am a

I my identity is at risk. Right? Because

it's just one dimension of who you are.

Uh but what happens sometimes is that we

can get very attached to certain

dimensions because we start to think

that that's who we are and I think

managers can do that. um and uh clearly

individuals, you know, on their teams.

And when that happens, it starts to get

very difficult to have, I think, more

objective conversations about, okay,

what can you get better at? What can you

get worse at? And so, I say all this

because I think this framework for me at

least and many people that I've talked

to has helped them realize that somebody

can give you feedback or you can be

maybe not great at certain dimensions.

You can have room to improve and that's

not who you are because you are all of

these infinite dimensions in one. And

none of them is is um representative of

like your true worth as an individual. I

am a big believer that we are all

beautiful and worthy and sure we have

all of these skills and yes we want to

improve those skills but it does not

speak to like who we whether we are

worthy or not by saying whether you know

we are strong or weak in these skills.

And so I think if you can take that and

really internalize that then you can

look at yourself a little bit more

objectively as a manager and you can

realize that there are areas where

you're going to be really strong. There

are areas where you have biases and

often they are one and the same. So I'll

give an example. People have often told

me as like I would get this in my

performance reviews from managers in the

past like hey Julie you're really

thoughtful. Uh so you know when you

think about something you have like a a

way to think about it you've clearly

thought about it in depth and you've got

like these frameworks and all this

that's a great thing and then on the

flip side I'll get feedback like well

Julie you know you're you don't really

say a lot um in in a dynamic discussion

like you're kind of quiet and uh you

know you don't really think that quickly

on your feet and what you realize is

like these are kind of again two like

because I don't do that And I'm not just

off the cuff. That's what allows me to

oftentimes be very very thoughtful,

right? Or like that at least again when

I was younger like it's sort of it's

very clear that that that particular

weakness is also very much speaking to a

particular strength which is I am the

kind of person that doesn't always have

a snap judgment. I have to really think

about it and internalize it and sometime

get to how I feel and then I can share

it and present it in the world. And so

just knowing that about me is supremely

helpful. Um now doesn't mean of course

that I can never get better at this

thing. But what I often think about is

mastery is where we realize that both of

these we can get better at. And what we

want to do is just

figure out in the context what makes

sense to be. So I got this feedback and

I'm like cool. One of the things I need

to work on is figuring out how to be

more open in person, how to speak a

little bit more clearly in person. Maybe

say things like, "I don't know exactly

how I feel about it yet, but this is

what I'm thinking right now." Like,

there's still clear tactics that will

allow me to be a more effective team

member and to do a better job in the

context of what I'm trying to do with my

team. So I've tried to build those

skills but the meta skill is now being

able to step back and say okay in

certain context it is really important

that we move fast and we are decisive

and we just do something and even if

it's not perfect we just kind of have to

do it and if I struggle with that I

should realize that that's an area to

improve upon. But there are other

contexts in which the right thing to do

is actually to take a step back and be

very thoughtful and to not rush into

decisions. And so that's like so what I

want to get to is not like let's reject

this strength or this weakness, but just

know that that's like where we come

from. That's naturally we might be wired

in a particular way. Our growth often

looks like getting better at doing the

opposite, but not rejecting again the

thing that we're good at, but rather

over time getting to this balance where

we can read the context in the situation

and know should I lean a little more

thoughtful or is this a time where I

need to try and be a little more

decisive and just share what I need to

what's on my mind right now? I love this

advice that things that we are

incredible at have a downside and

oftentimes the feedback we're getting is

is something we're not great at. There's

like a good version of that that people

appreciate.

And I was going to ask you and I I think

you answered most of this, but just when

you got this feedback of, hey, Julie,

you're not speaking enough in these

meetings. You're not uh contributing

quickly enough. Uh it sounds like so one

option is just like, okay, cool. That's

me. That's how I am. and I'm just going

to solve the problem this other way and

I'm just not going to change anything.

What I heard you say is find

opportunities where that's actually you

want to actually change that behavior

even though it doesn't come naturally wi

in specific situations where things are

moving fast. Um I guess just how far do

you recommend people push themselves in

things they're not great at versus

leaning further further into their

things their their strengths. Let's say

I think that's a really great question.

So the way I think about it is it is

very dependent on what is your goal. So

for example, let's say that you are

let's even take for example IC's versus

managers. I think often about the

pathway of an IC an individual

contributor as wanting to deepen a craft

like you just you love this thing and

you just want to get better and better

and better at this very specific skill

or this craft, right? So think about in

our dimension infinite like you pick a

couple dimensions like I just want these

to be I want to be like the top 01% and

that's that's kind of the pathway of

extending as an IC.

Now, if that's your high level goal and

you're like, I want to be able, let's

say your high level goal is, I want to

be able to do this, you know, 10 or

hours a day because I love it and I want

to be able to support myself doing it,

meaning I get paid and I have like a

great job and I want, you know, to um

have a bunch of impact in the world by

doing this thing, right? So, again, you

still have goals. Then you have to see

okay does my strategy of just deepening

these things um is that is there a

pathway to reach my goals according to

that and if there is awesome then if

someone's like hey do you want to be a

manager you're like nope don't need to

because these are my goals and this

pathway actually allows me to do that

but if somehow you get to a point where

I don't know the skill you really want

to perfect is not something that may be

commercially viable in the world that's

going to somehow allow you to buy the

the big mansion that you want to buy to

support your family, then I think you

have to ask yourself, okay, so if I just

do this, it's not going to cut it. I

might actually need to learn some of

these other skills in order to be able

to fulfill the job that is going to be

valuable enough that people are going to

pay me a bunch of money at this certain

level so that I can afford my mansion.

So, I just think it has to go back to

like what are your goals? And there are

cases in which yes like it supports it

will support your goal to do this and to

deepen your craft and there are cases in

which it won't and I think it's

important it's a very individual

question for each person but what I

often think suffering is is when these

things are not align

so what you want is like the giant

mansion and all of that and that but

you're like but I also just want to

spend all my time perfecting my egg

omelette and then you're just like in

this tension place and you it's very

hard to feel satisfied and fulfilled

because you're a little bit like oh why

doesn't the world value my my deep egg

omelet skills um like okay you can be

egg omelet you just have to you know

maybe not do this thing or if you want

this thing you may actually need to be

better at just egg omelets like perhaps

you need to expand your repertoire of

cuisines and like go and build a

Michelin star restaurant or something.

This is really good advice. It's not

just like definitely always work on your

weaknesses or don't worry about them.

It's if you need to do this thing to

achieve this goal that you have. Make

sure you understand what your goal is

and then is this thing a thing you need

to work on. For example, if you want to

become a VP, you probably need to be

really good in big important meetings

and not being on the spot and just not,

you know, waiting until everything's

over and then sharing an email of your

all your thoughts.

That's right.

Um, yeah. For me, I actually went

through a period where I was like, I do

not want to get promoted. I'm so happy

in this very specific role. Just like

leave me alone. And and and that path is

very different from the skills I need to

build to be a manager. And then things

change and then okay now these are the

things I need to work on.

Yeah. I love that you knew that about

yourself because I think it's so easy

for you know a young person to go into

their careers and everyone is telling

them maybe their whole family has been

telling them like you need to get you

need to level up. You need to get paid

more. You need to get that manager

title. You need to get a VP. And at a

certain point I think sometimes people

opt into this without knowing what

they're actually signing up for. Like

what are the tradeoffs and is that

really what you want to do? Does that

really align with your passions? And of

course, you know, sometimes we have to

again it's like it's a compromise for

us, right? But we get to design like we

get to design what are goals and what's

the right pathway. Um and I go back to

usually when people are unhappy it's

because these things are a little bit

out of sync. Like they want this big

thing, but they don't actually they're

not actually excited about what it takes

to do that thing and therefore it's just

going to be a mismatch. And along those

lines, uh it sounds like, oh, sure, I

can design my life and design my role.

But what I find is if you at least first

of all know what you'd love and ideally

do and then at least mention that to

your manager, it often is a lot more

possible than you think.

100%. I think it's so important to be

like we often also have this mental

model of like oh our managers are a

judge and they're going to judge me on

whether or not I got it I did well I

should get a promotion I should be fired

so there's this sometimes fear that

people have but I think in the very best

relationships the manager is like a

guide it's like look the manager has a

job and if you understand your manager's

job which is how to get outcomes better

outcomes from the team and also you

understand what exactly would your

manager consider success for the team?

It also makes it easier for you to then

be like, "Oh, well, if I do this

project, then that clearly seems like

it's very, you know, direct path to

creating value for the team." And that

also is a kind of project that suits my

skills. It's something I'm excited

about. Like you should suggest that to

your manager. But the other is true,

right? So you would know that if you

actually asked your manager, what is

your job and what do you consider

success to be and what is your greatest

hopes and dreams? And then you might be

able to help your own career and

yourself um because you know that

context. And conversely, if you say,

"Hey manager, these are my hopes and

dreams. This is what I think I'm good

at. I really want to get better at this

skill. You know, I really want to get

that VP promotion, but I don't know what

it entails. Can you tell me like what

does it take?" That's a really wonderful

conversation as well because then you'll

get all of that context and then you can

actually decide whether you want to do

it or not. And if you want to then ask

your manager for help, okay, if you see

opportunities that are going to help me

become a better presenter or increase my

communication, please tell me. Even

better, if you have feedback for me

about communication, I want to hear it

because that's what's going to help me

grow in this particular skill. And so it

becomes this collaborative relationship

much more so than this almost like

adversarial like I'm trying to get you

to give me a promotion and you're trying

to get me to like work harder. Like it's

yeah like that is not a a very good

vibe. There's a It reminds me of a guest

post by Ethan Evans that I'll link to

that has a really good framework for how

to actually do exactly what you're

talking about called the magic loop

where it it's kind of a framework for

figuring out what to work on and how to

help your manager see you're capable of

stuff and earn that trust.

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So along the lines of timeless manager,

especially new manager advice, you've

shared a bunch. Is there anything else

that you think is really important,

really interesting, valuable?

Feedback is one of the other topics that

I am super duper passionate about. And

my general impression for both myself,

everyone I've worked with is that we

don't value feedback enough or we don't

kind of think about enough. Again,

companies have these performance cycles

and so we're all like, "Yes, every six

months we're going to go and do these

reviews." That's when I'll get feedback.

But feedback really in my mind ideally

should be like a daily practice because

the thing that matters for us in the

long run as a team is how quickly are we

getting better.

So a team that just gets 1% better every

week compared to a team that gets 1%

better a month is even if they start off

at a much lower baseline is going to

outperform in a very short amount of

time the team that doesn't get better.

And so what is the best tool for us to

get better? It is feedback. And what I

think about in feedback is is it's very

similar to what we said earlier about

data and metrics. It's essentially

trying to put your hypotheses and test

them against reality. So as an example,

maybe I have this perception right now

that I am a positive and engaging

speaker. So I have this sense that like

I'm smiling and I'm very engaging and

I'm telling great stories. But is that

really true? I don't know. Like the

reality is that I'm often biased and we

all have, you know, we know these like

psychological effects, right? We're like

sometimes the Dunning Krueger effect

like people think they're way more

expert at something than they actually

are. You ask people, "Hey, are you

better than average driver?" And it's

like 70 or 80% of people like, "Yes, I'm

better than average." How could that

possibly be? We have biases. And

imposter syndrome is a bias on the other

side. It's like me feeling, "Oh, I suck.

I don't actually belong here." Whereas

that also is a bias. Like it may not

actually be true. In fact, I might very

well be here and other people value my

contribution. So we are just wildly out

of sync a lot of times in our

perceptions of ourselves, our strengths,

our weaknesses, what's going on. And the

way that we're going to understand and

truly get better is we need other people

to reflect back what is actually their

their truth. And the way I think about

it is like I'm going to ask you for

feedback after this podcast episode and

you're going to tell me something and

what you're going to do is you're going

to give me a gift because it'll be a

gift of reflecting something back of

what you see that I can't see. Right?

Just like if I have a leaf in the back

of my head, I can't see that. And so if

you tell me, hey, Julie, I have a leaf.

Oh, wow. Thank you. Okay, maybe I can

get rid of the leaf or or whatnot. Um,

but that is what feedback is. It is

essentially reflection back. It helps us

calibrate to re reality and it allows me

to get this information about whether or

not um I'm moving in the direction of my

goals. I I love that. I completely

agree. The challenge for most people, as

you know, is giving feedback that people

receive and don't feel defensive about

and then receiving feedback and not

being like, "Oh, no, they don't know.

They don't know anything. How dare they

say this about me?" Could you give us a

maybe a tip or two for delivering

feedback well and for receiving feedback

well and maybe even just like seeking?

How do you get more feedback? Because

this all makes a lot of sense. Most of

the time people don't get any feedback.

The best way the first tip on getting

feedback or delivering hard feedback is

first go and actually establish that our

relationship is one in which we value

each other's contribution. We want to

help each other grow and therefore we're

going to be the kind of people that want

to give feedback to each other every

week. So when you first start working

with someone, don't wait until something

bad has happened. Now you have to give

them feedback because that's already a

pressurized situation. Start by saying,

"Hey, really excited to work with you. I

feel like our best collaboration is I

want you to help me get better. I think

I'm good at this stuff. I'm not so good

at this stuff. What about you? Okay, you

think you're good at this stuff. You're

not. How about we just work together and

we just help each other get better at

these things? And the way we're going to

do that is all feedback is open. I want

you to tell me everything. Ideally,

you're going to then be say, "Yeah, I

want you to tell me everything." And

we've already established that.

And this is colleagues or manager or

colleagues.

It's like everyone. It's like people

you're dating. It's like, you know, your

children like it's it can be with

everyone. Just establishing what kind of

relationship do we want to have? I think

most people want to opt into a

relationship where you can be close, you

can be tight with one another. You can

say things to one another and not have

to hide behind like I think most people

will opt into it and if you opt into it,

everything gets easier down the road. So

the first thing is get everyone to opt

in that like this is the kind of

relationship that we want to have. One

trickle throw out that uh I've heard

that worked really well along these same

lines is asking people would you prefer

do you prefer feedback in the moment or

do you prefer it kind of uh every once

in everyone every month or or every week

or something like that and everyone's

like no no in the moment and just like

tell me as soon as something happens and

then that gives you that freedom to just

okay yeah let me give you feedback here.

Yeah. So if you get people to opt in yes

I want us to have a great relationship I

want us to help each other get better. I

want feedback. That's 60% of the hard

part of delivering difficult feedback

later on. So then the second tactic I

will say is that when you actually give

the feedback, it helps a lot. First you

have to check am I actually giving this

feedback because it's in the spirit of

trying to help

one another. And if the answer is yes,

then we're we've like, you know, moved

from 60% to 80%. It's going to go well,

right? But what can often happen is I'm

feeling like something happens, you do

something, it triggers me because I

don't know, I had like a bad experience

about that type of thing before and I'm

kind of feeling mad and I want to be

right. Like if my my real rationale for

why I want to give you feedback is I

want to validate myself. I want to be

right. I want to tell you you're wrong.

I want to punish you. It's not going to

go well. it's just already there. It's

there's no way you can deliver it and

somehow unless you're a tremendous

actor, um it's just not going to go

well. So, you have to first check your

intention. But if you've done that,

you're like, "No, no, no. I thought

about it. I'm calm now. I'm not like see

seeing red. I really think that Lenny is

just not aware that when he says this,

it makes me and other people feel left

out or whatever it is, right?" Then I

need to be able to give it to you. And

so usually then if you're like, "Okay,

now I might be nervous because I don't

want to offend you. I really value our

relationship. How am I going to tell

you, you know, I don't want you to get

defensive." What then the third tactic I

have is just say that out loud. Like if

I sit down with you and I say, "Lenny,

I'm so nervous right now is I want to

give you some feedback and I'm really

worried that it's going to impact our

relationship and I so value our

relationship and I don't want that to

happen, but I also feel like

it's just going to help you to hear it

if you can." That does so much of the

work of of it's it's humanizing, right?

It's like you're going to be you're

going to realize that I'm going out on a

limb. I'm being really vulnerable and

likely you're going to hear that so much

more than if I just find a way to like

drop it like just like lobby it over

because it's so difficult. Just actually

lean into the fact that it is difficult

and expose that because that builds a

lot of human connection.

This is amazing advice. Very tactical.

Okay. Uh is there anything else? So,

we've talked about a bunch of timeless

pieces of manager wisdom, things that

people need to hear, especially as new

managers. Is there anything else that

you think is really important that I

think people are just not fully groing

for being great managers?

I think the idea of win-win, I think

about that all the time in my mind. And

I go back to because I think that often

we have this story in our heads that

sometimes things are adversarial.

As a manager, I'm trying to get people

to be more productive. So, I'm trying to

get them to do a thing that maybe they

don't want to do. I'm going to try and

get them to work harder or I'm going to

um somehow put more pressure on them.

Like, if you start thinking like that,

that's not a win-win way to be thinking,

right? That's like you saying my getting

better outcomes has to come at the

expense of somebody else losing

something. Um, and I think if you start

thinking like that, it's very difficult

to come up with a strategy or to truly

be successful. But if you say, "Look,

actually my job is to figure out how to

create win-wins." So, I actually don't

want I don't want somebody over the long

run um to feel like what I've done is

just create a ton of pressure for them

and now they're super burnt out and

they're quick because that's not good

for our team. That's not good for me.

That's not good for our long-term

relationship. How do we find a like how

do we find the solution that can be

win-win? And I think if you think like

that, a lot of things get easier. So,

for example, with new managers, I think

this is true for me too. The first time

I had to tell someone that

they're not they shouldn't be a part of

this team was extremely fraught for me.

And the main reason was because I'm

putting myself in their shoes and I'm

imagining that this is truly horrible

and I've just done a huge disservice to

this person and that's like the most

awful thing. But there's another way to

look at it which is hey if this person's

on the team they probably want to be

successful. They want to do great work.

They want to be valued. They want to

grow their career. if this is not the

place for them because it doesn't align

with their true interests and the things

that are going to help them be

successful is just not the thing that

they either want to do or can do. Um, at

this point, it doesn't do that person

any good for me to somehow try to

continue to make it. It's actually going

to be miserable. Like I'm going back to

like prolonging that misery state. And

so sometimes a win-win thing is to just

say, "Look, it's not working. And I know

I I respect and value you so much that I

know you want to do something that you

can be proud of and you can grow in and

that's going to be really valued. And

right here, what we got, this isn't it.

That's like a win-win way of looking at

the situation, not a like, you know, oh

my firing them is just definitely going

to be a horrible, you know, I'm not

trying to say it's not going to be hard.

Obviously, it's hard, but it's in the in

the the mentality and the the the mental

model, I think, makes all the difference

because it's going to be different in

the way that I convey it to them. It's

going to be different in why this

actually in the grander scheme of things

may be great and it's going to reduce

this adversarial feeling where they're

now going to see me as like an enemy or

somebody with all this power who's

making, you know, uh choices that impact

them and they feel powerless. It has to

be a collaboration. And I think if it's

not win-win, if and I could be wrong. I

would say, "I don't think it's right."

The person could actually say, "No,

you're wrong." And that would actually

be great information because then maybe

we can go back and we can find a way to

make it win-win.

Yeah, I was just going to say they have

to believe this. You can't just s make

it sound like this. Here's the win.

You're getting let go. It's a huge win

for you.

Uh but in reality, the way you phrased

it is actually almost always true. Like

this is just not a place that you will

be happy and succeed at, and it's better

you go do something else.

Yeah.

Okay. I'm going to keep fishing in this

pool to see what else we got, but when

we run out, let me know. Is there

anything else that you think people

should know, should hear, especially new

managers that um they're still not fully

getting?

I think being aware of PE your own

energy and conviction is really really

important. So I go back like a lot of

these themes as you can see go back to

like you have to first understand this

about yourself and have the right

mindset and when you do it becomes much

easier to be able to be impactful with

other people. So this is another one. I

think it's very difficult for managers

to be able, you know, we talked a lot

about the three pillars of what are the

the major um uh tools of a manager,

right? The first is people. And so we

talked a lot about like the importance

of dimensionality and feedback and

helping reflect and grow people. I think

the second one is around purpose.

Purpose is like what are we here to do?

What's our northstar? And I think it's

very hard to actually convey that if you

don't have conviction yourself. And so

watching your conviction is really

important particularly since a lot of

people who are managers you often start

out not as like the founder and the CEO

of the company but you you might be like

the middle manager. So in some ways you

don't you didn't like create the vision

but you are in some ways expected to

execute it or take a piece of it and do

it. And I find that sometimes what new

managers don't pay attention to enough

is what is their true belief. Like they

feel like they might have to be like a

soldier. So they just get orders and

they have to execute it. But it really

makes a difference if they themselves

have gone through the work of of of

thinking through wait why are we doing

this? Does do I believe this strategy?

Does it make sense or not? And if it

doesn't make sense to go and actually

have the conversation with, you know,

their manager or whoever else just so

they un they can get to alignment on

like I really believe in what I'm doing

because if you don't really believe in

what you're doing and or you're just

kind of paring the thing that got passed

through the organization, it's very hard

for you to then be able to help other

people see what that magic is or to be

actually really effective as as a person

who can hold that vision and that

purpose. So, I just think you have to

really check in with yourself on like,

wait, I I know we're told to do this and

this is what we have to do, but how do

we really feel about it? Because if you

don't feel good about it, then it's not

going to be very likely that the

project's going to succeed. I can tell

you right now, every single manager I've

ever managed where they're like, I don't

really think this is a good idea. The

there's no case where I can think of

where the project somehow turned out to

be like wildly successful. This is such

a classic challenge of managers is

getting things done that you don't

really agree with. And uh I can't help

but ask you for advice on someone that

isn't that but in that place of just

okay we have this feature our co is

prioritizing. I just this is not a good

idea but I need to have a brave face and

not make it sound like I'm just being

told what to do and I'm just reporting

orders. I I don't believe in this. Like

you don't want to do that. You become a

terrible unsuccessful manager and you

people lose trust in you. What's your

advice to folks that are in that place

of just how to find that balance?

So, I think first if you feel that way,

you got to actually find a way to get it

out and and engage in dialogue. So, if

you're like, I think my manager told me

to do this, I think it's a terrible

idea. You got to talk to your manager

about it or you got to talk to the CEO

or whoever and feel because once you

engage in a dialogue, what will often

happen is you'll learn more like you'll

have new information, you'll have new

assumptions and maybe you'll have

influenced a project in some manner. But

often the more you can learn about okay

why did some other smart people feel

like we should do this and what parts of

it do I believe and what parts am I more

skeptical about like you can probably

decompose it and from a blanket it's

good or bad to like okay there's this is

a hypothesis this is a hypothesis is a

hypothesis I might kind of believe this

one the reason I don't like the proposal

I don't believe this particular

hypothesis but I believe these other

ones right and so when you can start to

get one level deeper into breaking it

down into a set of assumptions that

makes it much easier because then you'll

likely find something that you do kind

of resonate with and you might be able

to then steer things like okay that

hypothesis doesn't you can't I I believe

and disagree and commit but now we can

be very specific we can isolate the

thing that like and and what we can also

often do is like okay the reason I

didn't like this proposal is because I

have this this like I believe that this

assumption is wrong right so for

and they come up with like a really

stupid example, but you know, your

suggestion is I know we have a great

idea. We're going to go and put a

lemonade stand on every block. And my

core assumption is people do not like

lemonade. That's not the hot beverage

right now. And so I there therefore I

think this is stupid plan. But if I talk

to you about it and you're like, "No,

no, this is the core assumption we

disagree on." Likely what starts to

unfold is like, "Well, let's just can we

get some data? Can we get some

information? like can we just is there a

quicker way to validate whether people

like lemonade? Perhaps we should just

test it in one market before we go and

open up the lemonade stands across the

entire 50 states. And so what happens is

we can likely get to the actual specific

area and come up with something. And

then if I have to now share with my

team, you know, we're going to try this

hypothesis. I'm not sure how I feel

about it, but I actually do think like I

don't know for sure. And you know, our

our CEO seems to think this is but we're

just going to test it and we're going to

do the test in a way where that's what

we want to find out is like do people

really love like do 18 to 25 year olds

love lemonade if we put them on these

neighborhood what college campuses right

so it becomes very specific and

everyone's like well yeah I'm I don't

know for sure but like I'm happy to go

and and test that and and commit to it.

This is such a good advice. And there's

also you could layer on. Here's the

things I do agree with and believe.

Here's the ways that I see this as

totally right. Here's the piece that I'm

not so sure about, but that's why we're

going to run this test. And here's why

it's the smallest version of this test

and why it's a great idea just to figure

it out. And we'll we'll show them. I

mean, you probably don't want to say

that. Uh, as you give this answer, it's

so interesting. I almost want to do a

whole new episode with you later of just

like common conundrums managers have,

challenges that every manager runs into

that are really difficult to figure out

on the spot. We could save that for the

future. Okay, I'm going to take us to a

couple recurring uh themes on this

podcast, occasional recurring that every

episode uh corners that we uh take

guests to. The first is I want to take

us to AI corner. And what I like to do

in AI corner is ask what's a way that

you've figured out to use AI in your

work or your life that's just really

interesting, really useful.

Well, I already shared a lot about

education and learning, but I'll share

maybe a a more fun story. So, it's my

kids birthdays. One of them just passed

and my middle son's birthday is in two

weeks and my daughter's birthday is

by the way, the birthday just passed.

The kid didn't pass.

Okay. Yes, the birthday passed. That's

right. That's right. The birthday

passed. It's my kids' birthdays. And one

of my goals this year was to try and

build them something. So give them a

present that has me going back to being

the IC and making something for them.

And AI makes this really fun. And so I

just for my youngest son who is six

years old. Uh this is a an idea that I

stole from Eric Anton. And um if if you

know Eric, have you had him on your

podcast?

I haven't. I uh I'm trying to. He

actually sent me the what is it? The

It's what is it called? methophone.

Methophone.

Check this out. It's a It's like instead

of holding the phone in your pocket, you

hold this thing and then you walk around

with it and everyone's like, "What the

hell is that?"

Yeah. I too am the proud owner of a

methhone and the next version upgrades

with the little stickers.

But I don't have

Eric is great. You should definitely

have him on your on your He's such a

creative character. Um and one time I

saw him with a parrot on his shoulder

and I was like, "Why do you have a

parrot on your shoulder?" And he's like,

"Well, you can talk to my parrot. It's a

talking parrot." And then I spoke to the

parrot. And the parrot spoke back to me.

And what had happened is that he had

hooked up a microphone. He like kind of

surgically went into the parrot and

added like a microphone and a speaker

and connected it to uh voice mode on

chatbt. So that and and it spoke in I

think like a pirate voice. I was like,

"This is the best idea." And like my

six-year-old son is really into

raccoons. He has like a huge amount of

raccoon stuffies. I was like, I want a

raccoon that can talk to him. So, I made

that um using the Eric Antino method,

but it was great. It was a huge hit. And

now my middle son's birthday is coming

up and he is really into

parody. Like, he loves video games, so

Minecraft, but what he often listens to

on his Alexa are these parody songs. So,

it'll be like Justin Bieber's hit or

like Gundam style, but they've changed

the lyrics so it becomes like a a video

game parody of some video game that he's

playing. and they're horribly sung, you

know, they're like off tune. It's just

like some person who produced it. And I

was like, well, if he doesn't seem to

mind off King Seeing, I'm going to

create him an album of video game parody

songs and I'm going to create like an

So, I created an app on Replet uh that

that what and what it does is it you

just give it a song like uh you know

this is Justin Bieber's Baby and you

link to a Spotify song and I give him

some context like oh Lock likes playing

Kingdom Rush right now. we have like an

inside joke about um you know the

gargoyles being free money like whatever

it is I just give it a bunch of cont

like write me a song that just kind of

personalizes it and it's a parody of

this particular video game and it writes

me the lyrics it's pretty good at doing

this it's like pretty high quality and

then um and it you know again it does it

according to the beats of the music and

then I just sing it and record it and

then I got myself a song so I'm creating

an album of this which I'm going to give

to him he's not going to hear this

podcast so no one spoil it to him I

think he's going to go publish after his

uh birthday. But I'm very excited about

this.

Wait, so you're going to be the one

singing? Yes.

The song?

Yes.

I thought you were going to use Sununa

or some AI thing to actually sing it.

No, I think I'm going to sing it myself.

Um and it just like all of this made it

so easy. Like all I have to do is just

read like record. And again, he's not

into I'm not a very good singer, but

he's not into or he's not um it doesn't

turn them off to have to hear off key.

Wow, that is so be this. This gave me so

many ideas for gifts I can give to kids

in my life. And I just love how I love

how AI is making it I don't know easier

to be a parent in in some ways more

delightful. These are awesome examples.

Okay, I'm going to take this to a

different corner. Contrarian corner.

What's something that you believe that

most other people don't most other

people would disagree with?

I believe that

there's infinity in every direction.

So that makes me pretty contrary on

pretty much everything that anyone says.

So if somebody says something like on

Twitter, I sometimes play this game with

myself, which is in what context would

that actually not be true? And I think

the reality is that the world is so or

at least my reality and my understanding

of the reality is that the world is just

infinitely complex. And so for example,

if my kids say something like uh going

outside is boring or taking a walk is

boring or doing something is boring. My

general response will be well it's

because you're not seeing the infinity

that's in that direction. So even for

example something really mundane like

staring at a blank wall.

I think that you can make that actually

deeply deeply interesting because you

can use that as an opportunity to go

into your own mind and to figure out

like how you can make time past or you

can meditate on the the the existence or

meditate on your breath or just be

grateful for the purpose of being alive

and like two people, right? One person

you can say sit in front of a wall for

an hour and they will like my kid and

they will super complain and be like

this is the worst thing ever. But you

can put somebody else like a monk and

they'll have a wonderful experience.

And so it's not really about the

environment or the wall. It's really

about how we see it and whether we can

find the thing that is deep and rich and

infinite in that direction.

Wow. This these are some deep answers.

This is very uh I don't know Buddhist

very mindfulness oriented. this I I did

a retreat once and their their advice

was just yeah anytime you're bored just

notice all the things that are going on

around you like what does your seat feel

like right now what does the air feel

like you know what are you hearing right

now and it's exactly what you're saying

there's infinite things to pay attention

to and keep you interested it's hard

hard to actually do that for a long time

and practice that's why it's a practice

that's why it's a practice but I I I

repeat that to myself because oftentimes

if I have a bad experience I'm feeling a

certain day. It helps me to realize that

like it's often probably in my head like

it's because I haven't gained the skills

to be able to see the richness and

infinity in that and that's so like I

can maybe work on that and that feels

better than feeling like oh I'm a victim

of my circumstances like this thing

happened to me and like that's so awful

but now I'm powerless I can't do

anything about like that to me is a

worse feeling than the alternative which

is I just don't have the skill yet. I

can recognize it for what it is. I don't

have the skill yet, but I can I can

grow. I can maybe get better at it.

There is a person out there who could do

who had the same situation as me and

feels much more positively than I do.

And don't I want to be more like that

person?

That's such a beautiful circle back to

our very first episode, which a lot of

it was on imposter syndrome and

overcoming that and your story there.

So, I love that. That's a maybe a way to

close this conversation. But before we

do that and before we get to our very

exciting lightning round, is there

anything else that you wanted to mention

or share or double down on that we've

talked about?

I just want to say thank you. Honestly,

I'm so inspired by the work that you do

know. We've known each other for quite a

while. Um, and I just think from the

very first idea that you had for this

newsletter, for the podcast, it's been

incredible and I think the world gets so

much from it. I'm sure you hear that a

lot, but I am very grateful. Well, I

really appreciate that and I say this

every time we do a chat is just uh this

wouldn't have been possible without you,

Julie. Uh I was inspired by your new

longtime newsletter, the looking glass.

That's essentially my my idea was what

if I do this for product and uh I

started on Medium just like you did and

then I moved to Substack and then it's

like what if I charge for this and then

that worked and then I'm like what if I

do a podcast and then that worked but it

all began with your your concept. So

thank you truly. Yeah, and I think you

do it with so much kindness and

curiosity as you always have. So, I love

that.

That's just who I am.

Well, with that, we have reached our

very exciting lightning round. I've got

five questions for you. Are you ready?

I'm ready.

What are two or three books that you

find yourself recommending most to other

people?

The first is Zen and the Art of

Motorcycle Maintenance. I absolutely

love that book. It's beautifully

written. It's so deep. Um my whole

philosophy around quality is is

beautifully it really comes a lot of it

comes from that book. The idea and even

all the stuff that we talked about

change what does it mean to be at that

that forefront of change and dynamic

quality. I think he just talks about so

beautifully and so masterfully in in

that book. So old classic but I I try to

reread it every few years or so. Second

is

Conscious Business. It is my favorite

management book. It's a little bit of a

sleeper hit because I actually end up

recommending this one far more than my

own book.

Oh wow.

I read this one after I wrote my book

and I always tell people that if I read

it before, I'm not sure I would have

written my book because I would have

been like conscious business is really

the book that will that that that um

really really so much resonates. And I

think what um and all of the many of the

things I talked about this idea of

win-win, the idea of like being a

player, not a victim, um and how to

think about work, not just it's a job,

it's but like how do you really think

about aligning it with your own personal

values and what you want to do in the

world. I think that this book really

speaks to that so beautifully. It is

also very tactical. It's got a lot of

really wonderful examples. Um, I will

tell people the cover isn't very

attractive and I think that if you judge

a book by its cover, like this seems

very corporaty. The title also seems

like kind of like what conscious

business and the first chapter is a

little bit more technical, but if you

just could get past it and get into

chapter 2 and you start, you know, with

examples of the soccer team and it's

just like the best management book.

That is good uh good advice to get

people over the hump when they look for

it and they're like, "Okay, okay, I'm

gonna stick with it."

Yes. And okay, third book. Um, I love

the uh the book Good Inside by Dr.

Becky. It's a parenting book and it's a

very wildly popular parenting book. So,

I really recommend it to all parents.

But I also think it's just a wonderful

book for thinking about relationships

and because parenting is that it's like

a very very deep and intense

relationship and interaction that you

have with another human being. And

there's so many things that I read in

parenting books including good insight

by Dr. Becky that I think like are could

just as well been like a a management or

a team leadership book.

Uh I am thinking about trying to ask Dr.

Becky to come on the podcast. I feel

like there could be a lot of synergy

exactly for that reason

and she uses d this term sturdy which

you which is inspired maybe your

I probably got it I I mean I think she

talks a lot about sturdiness and that

just incepted right in right in here.

Yes. Yeah. Her whole thing is creating

being a sturdy parent. Strong but

flexible I imagine. Uh yeah, I love I

love her and I love her stuff. I watch

all her videos on Tik Tok and Emily

Auster. Okay, next question. Uh is there

a movie or TV show you enjoyed?

I have not watched anything that I have

no good answer for you. I think the only

thing I watched this year was a rewatch

of La La Land, which I do truly love.

So delightful. Okay. Is there a product

you recently discovered that you really

love?

I don't think there's anything too new.

I I love granola. I love Repid. I've

used all of the different coding apps.

Cursor is is big on me for for now. Um,

uh, I just got a Madic robot. I think

that's been really delightful so far. At

least the setup. I haven't used it like

a long long term, but it's the setup,

the way that it worked, the the fact

that it had little stickers and you

could make it into a dog or a cat was

like a wonderful experience.

The Madic Row bubble link to it. I am

also a huge fan. I'm not an investor.

That's uh essentially Whimo meets Roomba

for folks that don't know anything about

it. It's like a very sophisticated robot

vacuum built by like AI vision people.

Oh, I just thought of one more as well.

Uh the Limitless pendant.

So disclaimer, I am an uh a small

investor in Limitless. But uh what I

love about it is that um so okay, it's a

pendant. You wear it and it just records

everything that's going on and later it

summarizes things and it gives you

feedback. And I don't usually wear it

out because I find that maybe other

people feel like awkward that I'm like

recording everything. I usually try to

get people's permission. But I do wear

it at home when I'm with my kids. And

one of the best things that the pendant

does is it gives me feedback on

parenting.

What?

Like automatically or use throw it into

chatg? No, it will it out automatically

like if there's an app and it it will

sometimes notify me or if I check it,

it'll or I can also engage with like ask

it. Um, but what it does is essentially

it's like granola but like for your life

in in terms of capturing everything,

summarizing it and then giving you tips

and feedback and it said things like,

"Hey, there was that time you were

talking about the game and you cut your

kid off a lot and maybe next time think

about letting them speak fully and

listening better."

The app itself natively does that.

Yeah. I did not know that because I have

one. I haven't used it much recently.

That is incredible. Yeah. I wonder if it

gives you relationship advice too if

you're talking to your partner. I wonder

how he even knows.

Yeah. Um it's so I it was it was it was

did a pretty good job of inferring you

know that or I think it's a person too,

but it was it was like kind of eye

opening for me.

Incredible something. So there's a

recent episode of the our how I AI

podcast or sister podcast where somebody

uh wears that in their meetings with

CEOs with their CEO and automatically

turns what they're asking for into a

prototype from the meeting notes and

then sales teams can start showing it to

people to see if they're interested. How

about that?

That's awesome. That is super cool.

Holy moly. We don't even What is even

happening? Okay, I'll keep going. Uh do

you have a favorite life motto that you

find yourself repeating to yourself

sharing with others?

I like make it happen. Just a reminder

that at the end of the day we can do a

lot of we can have a lot of motion.

Maybe this is another one that I really

like. Um I think about this poster. It

used to be a poster at Facebook that

says don't mistake motion for progress.

So there's this idea of like be the

change you want to be in the world. I

guess there's all other ways of saying

the same thing which is like you know

I'm I can do things like we can all do

things. We're have better and better

tools to go out there and make things

happen. Make it happen.

Like the common meme on Twitter, you can

just do things.

Yes.

Final question. I like to ask this

question of folks that are really deep

in AI and been working with AI and kind

of getting a sense of where things are

going.

Is there something that you teach your

kids or teaching your kids think about

encouraging them to learn knowing that

AI is going to be a big part of their

life?

Emotional regulation is still really,

really, really important. That's

probably the thing that I think about

the most in terms of what I want my kids

to learn. I want my kids to be able to

introspect, to have a better

understanding of where their state of

mind is because we're still human. We

still have the same hardware that humans

have had for thousands of years. And

that's not changing even as the tools

and the environment around us change.

And so I feel that you have to really

understand yourself and you have to

understand what's going on for you and

where you are biased and where you are

not because AI can make it and this is

my great fear is that it makes things so

much more comfortable and I have this

great fear that this has been the

trajectory that we've been on with

technology right this is again going

back to like every strength is a

weakness technology makes things a lot

easier that's why we invent

like we're always human race has always

been about trying to better our

circumstances and in some ways control

our destiny like control our future. But

at the same time, all of that control

gets to a point where we have so many

shortcuts in our lives and you can

shortcut a lot of things. I can shortcut

relationships. You can shortcut like

hard feelings because now you can just

watch TikTok instead of actually dealing

with the very difficult emotion or

tension that you had with a colleague or

with your partner or with your children.

And AI makes it even I think more

attractive because now there's a person

who can or there's a thing that can be

very very personalized and if you're

like h I want a distraction I want to do

something you got that but how do we

actually still learn to sit with what is

our true biology that's not changing and

how do we continue to be the kind of

people that want to take on the freedom

of doing challenging things because I

find that if we don't do challenging

things we just we suffer we suffer in a

different Right. And so to me, true

freedom is you can pick the things that

are hard and you can feel pride in

becoming the the thing that you want to

be. It's not forced upon you. Like it's

not for survival sake anymore, but you

still have to pick. And I want to figure

out for my children the fact that like

it is really important to still find the

challenge. Yes, you can use AI to do

that, but really don't think about it as

a shortcut tool. Um because if that's

the case, I don't actually think that

they're going to be able to become the

kind of people they want to be in the

world.

What a beautiful way to end this

conversation, Julia. It feels like this

is just like some kind of huge milestone

of this podcast, just like having you

back three years later. It's like a I

don't know, a chapter in the in the

journey. Uh I appreciate you coming

back. I appreciate you sharing all this

wisdom with us.

Two final questions. Where can folks

find you online if they want to reach

out and maybe chat about maybe Sundial,

maybe whatever else you're up to and

then how can listeners be useful to you?

Well, I would love to work with people

who are at companies building really

cool things and want better answers to

um how we build better. And so if you

think your company would be interested

in working with us at Sundial um and

figuring out how do we make every single

decision maker into their own expert

analyst, please reach out. So that's one

area. So, um, sundial at sundial.so. Uh,

I am on X, so I've been tweeting a lot

more sharing uh uh thoughts you

know, going back to that that skill of

practicing just share what's on your

mind. But for the long form stuff, I

have my blog, The Looking Glass. It's on

Substack. Uh, I share articles and

thoughts about AI, product building,

leadership periodically. And then, of

course, I have my book, the a revised

edition with two additional chapters.

One is around managing remotely and the

other one is around uh managing in a

downturn or managing in change difficult

change scenarios. Um that will be coming

out in two weeks time.

It's going the new content will be in

the paperback. That's important and I

will I'll send you a version of this

when I get a copy myself, Lenny. But the

paperback has a gradient type of cover.

Um the hardback will eventually get the

new content but it just takes a while to

phase out from all of the different

retailers. So, if you buy one, I cannot

guarantee that it's going to have the

new content, but certainly the Kindle

and the paperback will have all of the

new content.

And then, so just for the publish date,

because this might come out later,

what's the what's the date it's coming

out? Just for folks,

September 9th.

Okay. Amazing. So, I think it'll be out

by the time this is out, so go buy it. I

imagine available Amazon, all your local

retailers.

Yes. Yes.

Amazing. Julie, thank you so much for

being here.

Thank you so much, Lenny. This was so

fun. I hope to be back in another three

years or whatever the next chapter is.

Hopefully sooner.

Bye everyone.

Bye.

Thank you so much for listening. If you

found this valuable, you can subscribe

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please consider giving us a rating or

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other listeners find the podcast. You

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about the show at lennispodcast.com.

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