Lenny's Podcast: Product | Growth | Career: Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft)

00:00:00 - 00:30:00

In this episode, Katie Dill, head of design at Stripe, shares insights on operationalizing quality and how design can drive growth. She discusses the importance of earning trust and listening to the design team, which led to improved engagement scores. The podcast also emphasizes the value of design in companies like Airbnb, Stripe, and Lyft, and the alignment between business and design goals in creating impactful products. The hosts highlight the importance of quality, beauty, and collaboration in delivering excellent products.

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00:30:00 - 01:00:00

The podcast explores the importance of setting high standards, maintaining vision and alignment, and understanding quality from the user's perspective. It discusses a process implemented by the company to ensure product quality, including regular calibration meetings and shared ownership. The podcast also emphasizes the significance of firsthand experience, judgment in decision-making, and advocating for quality at all levels of the organization. Additionally, it highlights the formula for performance, which involves increasing potential and decreasing interferences. Visual communication and prototypes are also mentioned as valuable tools for improving awareness.

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01:00:00 - 01:30:00

The podcast features a discussion on the challenges of sharing project progress in a large team and the benefits of opening up work in progress. It emphasizes the importance of aligning product and design teams for faster iteration cycles and better clarity. The guest provides tips for hiring a designer and highlights the importance of teamwork and incremental progress. The hosts also discuss their favorite project at Stripe, Stripe Press, and recommend valuable books for readers.

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01:30:00 - 01:34:00

In this episode, the guest discusses gender equality and emphasizes the importance of recognizing women's capabilities. They also share a valuable lesson from flying planes that relates to trust and support in the workplace. The episode concludes with information on how to connect with the guest and explore potential job opportunities.

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the use of the word beauty in books that have been digitized by Google has decreased pretty dramatically.

And it's aligned with this idea of functionality is king, functionality is what matters.

And as if people think about functionality and beauty as two opposite things,

like no, they're not two opposite things.

Functionality is important, and actually beauty enhances functionality

because it does make things easier to use, more approachable, more compelling to use.

And the other piece of it that is not talked about in business as often is just the importance

of how people feel, things that are more beautiful, increased trust.

And you see that we've put painstaking detail into this,

and we care about the details of how something works.

And that gives you assurance that we care about other details that you can't see too.

Today, my guest is Katie Dill.

Katie is head of design at Stripe,

where she oversees product design, brand and marketing creative,

web presence, user research, content strategy and design ups.

Katie was previously head of design at Lyft and head of experience design at Airbnb.

She's built and led design teams at three different hyper growth companies,

seeing the team scale at least 10x, and two of which Airbnb and Stripe are some of the biggest

and fastest growing companies in the world and also the best design products.

In her conversation, Katie shares stories of trials and tribulations of leading large design

teams, processes she's put in place for operationalizing quality, how she thinks about

quality and beauty very practically, how design can directly lead to growth,

and examples of this that led to big lift and conversion at Stripe.

Plus a math formula she uses to increase team performance,

how she suggests organizing your design and product teams,

what to look for in design hires, and so much more.

I was really lucky to get to work with Katie while at Airbnb

and I am so excited to have her on this podcast.

With that, I bring you Katie Dill after a short word from our sponsors.

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Katie, thank you so much for being here. Welcome to the podcast.

Thanks for having me. Good to be here.

It's absolutely my pleasure.

So as we were preparing for this podcast, you hinted at a story that you had from your time

at Airbnb, where the design team staged an intervention with you,

which I had no idea about because I was there during this time

and did not know this was happening.

I am so curious to hear the story. Can you share what happened?

Uh-huh. Starting with the easy questions I've seen.

Yeah. No, I'm happy to talk about it because, frankly,

it was the biggest learning experience of my leadership career,

or at least that happened in one moment.

And it happened in my early days at Airbnb.

So I was hired to take on the experience design organization,

that's basically the product design team, which was 10 people at the time.

And so they had been reporting directly to one of the founders,

and they were going to start reporting to me.

And during my interview process, I learned a lot about what was working

and what wasn't working and some of the trials and tribulations

with the design organization and its collaboration with others.

So it seemed like there was room for improvement

in how engineering and product management and design all worked together.

And there was also really low engagement scores in the design team.

And so I came in ready to go and excited to try to help make some change

based on all the things that I had learned from various leaders

and people across the company.

And I came in swinging, ready to go.

And then about a month into my time there,

I got a meeting on my calendar Thursday, 8.30 a.m.,

it was an hour and a half, with half of the design teams,

that was five people, and our HR partner.

I don't know, that's never a good sign.

Yeah.

And I remember this so vividly and remember walking into the office

and all the rooms in Airbnb's office are very unique spaces

that look like Airbnbs.

But of course, this was the one room with all white walls

and just like a gray, flat rectangle table.

And I walked into the room and there were five of them seated around the table

and they had a pack of papers in front of them.

And they went on taking turns, quietly reading from the papers,

all the things that they saw that I was doing wrong

and all the things that they didn't like about me.

And it was a really hard moment there.

I went through all the usual kind of stages of grief

when one hears feedback, which is this immediate want to respond

to be like, oh, well, there was a good reason for that.

And that's not how it actually was.

And this is why I did that.

But luckily, I had the sense to just listen and not respond in that way.

I mean, clearly what they were telling me

is that that was one of the things that was missing.

And so I heard them out and took it all in.

And regardless of each individual saying what was very clear

was the missing piece, the theme that was across all of that

is that I hadn't earned their trust.

So whether, how right or how wrong what I was doing was,

is like the key piece is that I wasn't bringing the team along with me.

They had no idea that they could trust in what I was trying to build

and what I was trying to shape and that I cared about them

and that I had their best interest and shared goals at heart.

And that was absolutely my fault.

And in retrospect, as hard as that was, I'm very grateful and very amazed

that they could come together and share that with me.

It can be hard to bring feedback forward like that.

And so it was an extremely valuable learning experience.

And I took from that to then immediately shift how I was operating.

And really a key part in building trust was to listen,

to hear out what the individuals and the team were setting out to do,

what they cared about, what motivated them.

And so I started to make pretty fast change

and still moving in the direction that was necessary for the org

to make a really large impact in how we were operating,

but bringing folks along with me.

You can inflict change on people, but if you want to do it with them,

you really trust is the key element there.

And then a couple months later, we had the best engagement scores in the company.

So it did objectively improve the situation.

And since then, taking that on into next steps and other companies that I've joined

and just think about instead of coming and swinging, come in listening

so that you can really set out to make change

that actually has true positive impact on the folks around you

and that you bring along with you.

Wow. I was there during this.

I did not know this was happening.

Is this the time when all the designers

were all always in one room together in there?

Is that that period?

Before I got there, I think there was a little of design

is just going to sit with design and not necessarily work

in close proximity with engineers and product managers, etc.

And one of the things that I believe as a necessary part

of building a high functioning organization

is that one, building together is important.

So having engineers and product managers and designers

be together, have shared goals and align on that

and be able to just look over each other's shoulder

and talk about things is important.

So sitting together is important.

However, that fair thing that you're talking about

actually was something that I was very devoted to,

which is bringing design together at key moments

multiple times throughout the week

to also build a community in design.

You know, like Joe Botte at Airbnb once said,

it's like, well, what t-shirt do you wear?

Like, what team are you on?

And I was like, you wear two t-shirts.

You have two t-shirts, you have the design t-shirt

and you have the marketplace t-shirt

or whatever cross-disciplinary team that you work on,

because both are really important communities to build

for slightly different reasons.

So yeah, there was a good spot for that.

Zoom me out a little bit.

I think the elephant in the room a lot of times with design

is this idea that I'd say most PM's, most founders,

intellectually understand the value of design,

understand the value of high quality.

But day to day, it's often not actually prioritized

versus new features, new product launches,

and partly because the ROI is just really unclear.

If we spent another month making this more awesome

and making this even more amazing design-wise,

experience-wise, what is that going to get us?

Clearly at Airbnb, design was highly prioritized at Stripe.

From an outsider's perspective, it clearly is.

I'm just curious what you've learned

about how to make the case for the ROI of design

and just how Stripe and Airbnb and Lyft have done that.

It's a great question.

And I think this is an age-old question

that I don't know if we'll ever go away.

And probably because the quality bar keeps evolving

and keeps rising.

But I think first to level set before we dive into that,

I would say that there are levels of quality.

There is the like, does the thing work?

Does it provide some sort of value proposition

that executes on its job?

That's baseline quality.

Next, is it like, does it do it exceedingly well?

Is it like error-free?

Actually, maybe that's not even exceedingly well,

but just error-free and it actually works

in a well-rounded way.

And then beyond that, like level three,

level four, level five, does it exceed expectations?

And it does something that you weren't even

in seeking for as a user.

And I do think the levels of quality

should be based on user expectations.

I don't believe that there are disciplines

that just don't care about quality.

I think it's more about that prioritization

and kind of like what you talked about is just like,

is it really worth getting something

to that exceedingly well state?

Or is it, what about just like another feature?

And getting that being seduced by the chase

of another feature versus actually taking your features

to a level of being great, that is hard.

And I get it when you look at your user base

and they're all shouting from the rooftops

for this additional feature that of course

you're going to want to prioritize that

over something they've never asked for.

And then the other thing would be you end up

with like you've got three things that you could possibly do

to make perhaps the next stage in your product development.

Two of them you know you can measure

and they're going to line up to business goals

and one of them you can't.

Of course that's going to be enchanting

to want to go after the things that you can actually measure

and you know that they're going to have that impact.

But the companies that know that quality is non-negotiable.

It is a long-term necessary aspect of what they build.

Don't play that numbers game or that they,

what they do is they recognize that it is absolutely

functionality but the quality of those features

that is actually going to get great usability,

desirability in their product.

And actually I think it's kind of like an analogy for

going to the gym or working out.

Like I don't know about you but literally every time

I think to do this there's like a fight in my head

of like do I really need to work out today?

You know is this one day you know going to give me six pack ads?

Like of course not.

So like why go?

Why not just like skip it today?

But of course like then at some point hopefully I realize

that it's like well if I skip it today

what's to stop me from skipping it another day.

And really in the belief of that these things can you know

it really does add up to a better outcome in the end

and so you know a longer healthier life.

And so hopefully I get myself together and go to the gym.

And I do think some of the best companies in the world

and the planet thinks that way.

And I recognize that

or customers don't always ask for it.

I mean you might see it in you know support cases for example.

Like clearly they don't know how to use this next step

and that is probably a quality issue.

And that you know they might be asking for

in a more improved features.

But some of the levels of quality that you know the level two

and three and four you know you might not get direct asked for.

But I guess I'll you know give you another analogy.

If you don't have competition that's fine right.

Like if you think about the first car I'm sure that wheel

was really hard to turn.

And I'm sure that seat was not comfortable.

And you know you could have any color you want

as long as it's black right.

But like there was no competition.

The competition was a horse so you know no big deal.

For you know cars today.

It's like the stitching.

The you know the choice of the leather.

The sound of the door.

Like these distinguish you know what okay car

to a high end special car with higher value.

And this is very much by understanding

that how the details matter

and how execution of quality will take it to the next level.

And you know lastly I'll just say that like I know

there's this saying of like its growth versus quality.

But like quality is growth.

And if you think about how you can make your product

easier to use and more understandable.

You know that will of course drive people to use it

and use more of it.

And take you know have a better experience with it

that they'll you know want to talk about with others.

You know in fact at Stripe our growth team I would say

is like pretty much maniacally focused

on building better experiences

because we've seen it tied directly to our business metrics.

We have things that we've improved on

in you know our onboarding flow for example

to make it easier to understand the products.

Understand how they work for your different use cases.

Such that then we have seen activations increase

because we've made these quality improvements

that are just directly tied to growth.

You know one of the biggest examples

that I've seen of business impact through quality

is actually in the checkout experience.

So we've done research on the checkout experience

in some of the top sites e-commerce sites.

And we found that 99% of the top e-commerce sites

have errors in their checkout flow

that actually hinder it more impactful,

more you know seamless quicker checkout

and therefore higher conversion with their customers.

And these small things really like their quality issues

they're just that if you really understand

what a consumer is trying to get out of the experience

then you can make it better.

And so we have been maniacally focused on that

over many years trying to make the checkout experience

so much better for businesses and their consumers.

So by improving the quality of the checkout experience

through details small and large

we have seen a 10.5% increase in businesses revenue

from that you know an older form of checkout

to a newer form of checkout.

And those little details matter

to have such a material impact on one's revenue.

You mentioned this before we start recording

but you guys power the checkout flow for some very big sites.

Can you mention a few of these

because they'll give people a sense of like holy moly.

Yeah, Stripe is used by millions of businesses globally

small and large from early stage startups

to SMB's larger organizations and enterprises

like Amazon and Hertz Shopify Spotify X

which I believe you use.

And you know the work that we do it ranges

we have checkout flows.

So when someone's paying online or in person

or we also provide a suite of financial automation tools

so that you can run your subscriptions business

and recognize your revenue and receive tax

essentially you know manage the complexity

of the financial space through powerful tools

that hope to make your job easier

so you don't have to sweat the details

of how these things work.

I just want to follow this thread a little bit

you talked about these opportunities

to improve the checkout flow through a design lens

you could also think of it from like

like as a product manager I'd be like

oh wow let's just find all the things

that people get stuck on and fix them.

How is it that you see that

from the quality design perspective

versus like oh there's just let's just move this metric

and here's all the things that are stopping people.

What would you say is the designer's lens on that

if there's anything there?

I honestly a pet peeve of mine is this way of talking

about things as there's business goals

and there's design goals because you know

I think maybe the first conversation

you know one should have is that you know

what are we trying to build towards?

And I would think that folks that want to create

you know really impactful products

they want to create quality products

and that they want to create things that

actually serve their customers

in a you know positive and beneficial way

because they know that will build

a stronger business in the long run.

So yes there may be you know slight prioritization

details different through the process

where you know a designer might be thinking

you know more about the emotional experience

and how somebody feels

because that's you know oftentimes how they're wired

and that is an important lens to bring on it

whereas you know somebody else might just be like

well you know just make the button bigger

and they'll click it more often

and you know that's what the outcome that we seek.

So this is again why I was talking about

how important it is to have multi-disciplinary

teams that work closely together

because sometimes we are you know

the checks and balances in the conversation

but I do think if we can align on

what are we trying to build?

Are we trying to build something great?

Then you know we can you know recognize the fact

that like it isn't just that you know

utility is an incredible important part of that

but so is usability and so is desirability

because these things together

make something truly great

and so you know beauty is an important part of that

because it does make things more useful

it does make things more accessible

and that with these things kind of coming together

you can you know build towards something better.

I think that you know beauty on its own

or just like you know like craft on its own

without utility I mean that's like

I don't know that's like blu-ray or or path right?

Like that does not lead to a high quality product

so it is like the combination of these things

and so it's like stepping towards that

but if you really want your you know product

those features to be utilized for all that they're worth

and like to actually you know gain such you know

esteem and respect and reuse

taking it to that next level

and thinking about you know how do I make this

actually you know an enjoyable use

and that it really feels like it's you know

meant for me and it maps to my mental model

that craft and that quality of you know

the execution of those details is going to be paramount.

You mentioned this word beauty

and I wanted to follow on this a little bit of just

this is a big question but just like

what is great design?

What is beauty?

Is there like a objective definition

where if designers like this is great design

is there just like yes that is true

or is it just an opinion?

How do you think about what is great design?

What is beauty Katie Dill?

I love that we're talking about this

because I feel like there's probably some people

listing that are like squirming in their seats of like

you know like beauty like we're talking about business here

and I mean that's which is great

and the actually there's a fun fact

it's Stefan Sagmeister and Jessica Walsh

have a book called Beauty

and I would highly recommend it

very very worth the read

but one of the first things they talk about in the book

is that from the 1800s to the 2000s

the use of the word beauty

in books that have been digitized by Google

has decreased like pretty dramatically

and it's aligned with this idea of like

well functionality is king

functionality is what matters

and as if people think about functionality

and beauty is like two opposite things

but what the whole book talks about is that like

no they're not two opposite things

you know functionality is important

and actually beauty enhances functionality

because it does make things easier to use

more approachable more compelling to use

and there is actually some objectivity

to whether or not beauty enhances things

but if you ask you know a wide audience

you know what color do they like more

or what you know version of things

do they like more like they tend to say the same thing

because there is this like shared understanding

and you know the other piece of it that

yes I can imagine is not talked about in business

as often is just the importance of how people feel

and you know a good example of how something looks

and how something is structured

and how that can translate to that

also from the the book beauty

they mentioned that they studied the tweets

that came from people that were traveling

through Penn Station versus Grand Central

and if you've been to those places

I'm sure you know where I'm going with this

which is just like that the people tweeting

from Penn Station it was just like

more negative than the people that were tweeting

from Grand Central Station

that tended to be much more positive and optimistic

and so you know the things that you create

have this impact and if you're thinking about

like I want people to enjoy using my product

I want them to feel you know at home in our product

of course beauty is a part of it

you know and this matters deeply to us

and I know you know as a financial infrastructure company

in the B2B space you know some may assume

that that doesn't matter as much

but it's actually a key priority for us

because number one things that are more beautiful

increase trust you see that like we've put

painstaking detail into this

and we care about the details of how something works

and that gives you assurance that we care about

other details that you can't see too

then secondly it is easier to use as I've mentioned

it gives better user outcomes

you know what we're trying to do is

we're trying to have quick businesses

to make the right decisions to be more successful

at what they do

and by you know bringing a interface

or you know our invoices or whatever it might be

to be more beautiful and more easy to use

and more trustworthy

that will lead them to better outcomes

thirdly I strongly believe beauty begets beauty

and so when you know our business users

or the consumers see you know the beauty

and the care and the creativity

that we put into the things we deliver

then you know that again reassures them

of you know the just like the care that we put into them

and actually a perfect example of this

have you seen the show The Bear

I have yes great example

all right and I know it's spoilers

but like all I have to say is peeling mushrooms

do you know what I mean

yeah yeah yeah such a good example

such a good example

someone just mentioned that same episode

recent podcast episode

okay all right well it's that good

it's that good and I wish I could remember

which episode that was but

it was seven I forget

yeah that's exactly right

oh nice okay all right

well then lastly you know quality is a matter of pride

beauty is a matter of pride

if we put that in you know kind of care into our work

more people want to work with us

because they want to see you know their time spent

and the care for their craft recognize and utilize

and see that that can can be you know

put together into something really impactful

and so you know we really put that on the pedestal

you know because we know how much it matters

to our users and how much it matters

to the people that work with us

beauty beauty is an important part of it all

amazing speaking of beauty

I think when I think of stripe and beautiful

I think of your website

and some of the specific landing pages you have

which are just incredibly nice

I'm just curious how you decide

it's time to redesign your website

and how much time and thought you put into a new website

because that feels like a

a common question founders have like

should we redo our website

and it feels like

you guys really think deeply about that

so I guess is there anything there that you can share

yeah there's definitely a couple things

we could talk about in terms of like

operationalizing quality because

I mean the gravitational pull is to mediocrity

right like you know it is it is very easy to

fall into a path of a baseline

where what is required to go to that next level

where something feels truly great is

certainly a lot of effort

and it's a concerted effort

and I will definitely say

we are a work in progress

you know we have not nailed all the things

and it is an ongoing pursuit of excellence

and so the way that we build the website

is that you know we we certainly do

you know put a lot of care into

what we're putting out into the world

and we view it as a articulation of

you know how we care about our users

and in all that we provide for them

so we take that very seriously

we try to kind of meld art and science

so it's the creativity of the work

but it's also just like the technical

kind of power of the way that we show it

how we've actually operationalized

the way we do that

is that we have design and engineering

and our product partners

and product marketing

we're really really closely on this

and actually it's one of the few teams

where all of these things report

well not all of them

but most of those functions report into one place

so engineering and design

actually all report up into the design organization

when they work on the website

and together they like quite literally

as we were talking about earlier

you know if we were physically together

they would be standing side by side

and you know they're batting ideas back and forth

because you know the engineer on the team

you know has a great idea

for how we could go about executing on it

and the designer on the team has another idea

and had to you know push that a little further

and so that kind of rapid cycle of iteration

is really really powerful

especially when we're you know trying to move quickly

but at an extremely high standard

that's super interesting

is there anything else

that you found to be really helpful

in just operationalizing

great design craft beauty

any processes systems frameworks

yeah I would love to tell you

about something that we've actually rolled out

pretty recently

that I'm extremely excited

about the positive impact on

awesome but before I get into that

one of the things that you know

kind of has been driving

a little bit of this process

and the way that I've been you know

thinking about how you know

we can build better things at Stripe

is actually I've been just talking to people

talking to different you know

design leaders product leaders

engineer leaders

at different organizations

and try to understand you know

how they go about it

and there are a couple of themes

that are clearly coming through

you know number one is that

quality is definitely a group effort

you know you're sunk

if you think that like you can just like

hire some incredibly talented person

and like and they'll do it

that'll be fine you know

the rest of us will do what we're doing

and they'll do it

or that it's just like one organization

that's going to look out for quality

or you know QA is going to solve it all for you

it really does need to be

you know an organizational and a group effort

and if you think about like you know

the way that you run you know

the the internal functions

is going to show up in the outside

and like how clear you all are

and how you're talking about it

and the standards that you set inside

and you're constantly reminding people of

in the way that you communicate inside

will then eventually show up outside

so take you know of course

keeping your talent bar high

and then thinking about how those things

you know really need to be cared for

you know that shared care

across the organization is number one

number two is that you know

there needs to be some amount of vision

and alignment

so you know if you hire all the best people in the world

and you just like set them out

to like go and do their thing

what are the chances

that they're all going to end up

with something that actually aligns pretty well

right like even if they all have incredible taste

and they're very good at what they do

you know there's subjectivity

to every decision in some part

and so that they might end up

with some things that are really great

but don't fit together as a really nice whole

like the perfect example

would be building a house right

so you have like the person that works on the roof

and the person that works on the deck

and the person that does the siting

etc etc etc

and a house is arguably far less complex

than most of the technical products

that we all know

and yet they're like

is painstaking effort put into

having the plans

and having a drawing

of what the final thing is going to look like

there's a GC

there's an architect

and these people are helping to make sure

that all those pieces fit together

and we should have that same care

when we're trying to build products together

and so I think a big pair on that

is then the next piece which is editing

and you know you might call that your GC

or your architect

or somebody that kind of sees

how all these things fit together

and then has an ability to kind of help narrow

and reduce and remove

the things that don't fit

and so like at Airbnb

you know Brian Chesky is like the editor

of all the things that you know come together

at the Economist

you know there's a chief editor

but you know other organizations

they might decentralize that approach

which is you know certainly possible

and but you know challenging

because you do need somebody to help

kind of like see these things come together

and that pairs with the next piece

which is about courage

like the ability to actually like say

you know no this isn't good enough

like to have the resolve to just be like

almost but no

which is like one of the hardest decisions

I think leaders can make

and certainly I've had to ever make

in my career too

it's just like you know a team puts like

all this care and effort into something

and then you're gonna say like

actually it's just like

unfortunately like we're just not there yet

let's try again

and that is I think you know incredibly

important part of getting there

and building that you know

kind of the fitness of what you do

and then lastly the thing that I've learned

that will lead me to the example

that you were asking about

is that in order to build quality

you really do need to understand it

also from the user perspective

which kind of gets me into you know

my fixation with journeys

because that is how a user sees it

the user very very very rarely

just like deals with any aspect

of what you build in isolation

there has to be a moment where they learn about it

there has to be a moment where they get to know it

and then there's a moment where they

actually decide to use it

and then well something just changed

and now they need to use that product

in some other way

and so you have to understand it

from that point of view

to really understand whether or not

the quality is there

and I think that's a critical piece

of building teams that have empathy for their users

so we have been operationalizing that

you know all the things that I just mentioned

but like one of the key pieces is to

you know kind of bring that approach

to understanding the quality of the product

and so our goal was to set out

to try to solve the fact that

products can be shipped

and they could be at their highest gain

when you ship them

like they go through all the processes

internally

to be you know a high quality thing

and then it gets out into the world

and then over time the quality regresses

and some of the reasons for that

is that you know other things are being shipped

and it's kind of like again

back to an analogy of a house

imagine you have one room

where you redo the molding

and you know you paint the little aspects

and you've put like new plates on the lights

now all of a sudden that room is great

but it makes everything else look worse

and the whole composite is worse

and so that is you know

something that can happen to products

is actually they you know kind of get worse over time

and then you organize a company oftentimes

and you know parts to be able to focus

on their key business areas

that's a very good thing

because they get focused

and they know what they're you know

building towards

and they get expertise

and they're you know laser focused on that

and so that ideally they move faster

but what also happens

is that they get so focused on that

they forget about that piece of the journey

and how it all fits together

and not recognizing that you know

part of their product experience

is intimately tied to another

so what we did was we set out to

number one increase the you know

kind of awareness and accountability

of leaders to own their journeys

and so what we have established are

you know we started with 15

of our most important user journeys

15 is you know

somewhat of an arbitrary number

it's a number that we can kind of

keep track of

but also you know

has pretty good breadth

but it's certainly not comprehensive

of all the most important things

but 15 of our you know

critical user journeys

the things that we know matter

so deeply to our users

and we must get right

at the highest level of quality possible

and so those 15 things

then each have

engineering product and design leaders

that are responsible

for the quality of those products

and they review these journeys

what we call walk the store

where they review them

as if they're in a walk in the floor

of their store

on a regular attendance

and they friction log

what they experience

which I know David Singleton

talked about on your podcast

and they will write

you know what they have seen

what's working

what's not working

and they're

they're viewing this from

you know they're trying to put

themselves in the shoes of their user

this is of course

doesn't replace user research

but it you know

kind of substitutes it

and it adds to that

and so they go through the experience

and noting you know

what's working

and what's not working

and very critically

it's a journey

so a lot of times

you know it starts from

internet search

it starts on you know

Google trying to understand something

goes to the website

you know they end up on docs

they end up in the dashboard

and they're seeing it

as a user might

and with that they'll be

they're able to find

you know the entailments of

you know the experience

that may or may not be working

and they drop that down

they file bugs

they reach out to the teams

that may own the different

parts of this experience

and then they score it

and then on a

you know again a regular key

and so we come together

in almost like a calibration

where we meet

and we talk about the score

of their work

and it kind of relates

to performance reviews

right like

you know performance reviews

managers are assessing

an individual's performance

which is hard right

like it's like there's some subjectivity to it

just like understanding quality can be

but what we do as managers

is we calibrate

we come together

and we talk about like

okay how well is this

you know

is our interpretation

of our

ladder's document

and you know how well

does that performance align

and are we doing it's

you know consistently

across the rest of the organization

and so we do something very similar

we calibrate

you know these scores

because what we're really trying to do

is not just you know the

15 essential journeys

and the owners of those

we want to actually like

up level

and bring more

you know shared understanding

of our quality bar

across the company

and so these moments of calibration

kind of start that

and then having leaders do this

you know kind of like

creates this like

you know number one

it like cascades

this idea

of the importance of owning your journey

and then also

has upstream impact

because when people see

the state of products

in the wild

as a user would

they learn a lot about

you know what are

you know some of the bigger opportunities

that we can make

to make the product better

what are some of the things

that maybe want to change in our process

to make sure that we have

you know even better things

coming into the wild

and you know one of the

best parts of this

is since then

we've learned that

you know folks

you know have seen that like

oh my goodness

our SEO

for this particular product

you know or

you know the way we're articulating it

doesn't align to actually

how we want people to understand it

later on in the journey

so if we improve this over here

we're going to improve outcomes later on

and so they're seeing that

and you know they're

now you know like

able to make that happen

even you know faster

to make some of the changes there

and then my you know real favorite part

is that we're hearing from folks

that maybe at first

didn't see this as as necessary

that you know maybe in different functions

that are you know just like

oh you know I was

so very focused on executing

you know the technical ability

of what I do

on this thing

but I you know hadn't seen it

from this lens before

and now they're like

actually like converts of like

yes this isn't a really important part of it

and that goes back to the point of like

it's a group effort

like you don't want just one function

looking out for the quality of the product

so having engineers and product managers

and people of different disciplines

kind of walking the store

seeing the experience

feeling it firsthand

I think will lead to better care

in you know all of the details

that will align to

better craft in the end

oh man what an awesome process

I have a million questions

I want to ask to

better understand how you operationalize this

I'll try to ask just a few

but one thing that stood out

about this process is

I think people

kind of don't trust their own judgment

when they're

looking at their own product

they kind of

especially product managers

almost have to like

feel like they have to rely and use research

or data to like

know a thing

versus like

I just see this

and it feels bad to me

and I think

I've learned over time more and more

you should really trust that

because you're

you're spending your energy

trying to use this thing

you're not that different from a potential user

so just

I love that this actually

relies on your personal judgment

trying to use a thing

which I think people undervalue

yeah

a couple just very tactical questions

how often roughly does this happen

is it like once a quarter

yeah and

yeah to your first point 100%

they're all just forms of input

like I'm definitely not saying

like do this instead of user research

do this instead of data

it's like

you know these things in additional sense

and I do think what's so powerful

about doing it firsthand

is that

although I am like

the biggest supporter of user research

even hearing somebody talk

about an experience

while that is like

really really powerful

feeling the pain firsthand

is just like this next level

of visceral understanding of like

oh this could be better

and your users

you know they might not always say

what's missing

or what's wrong

or maybe they don't

you know they don't know

that certain aspects of it could be better

so

yeah having your

you know

point of view on that

in addition to the user research

and what you've heard from them directly

is really really important

but you asked about how often

we have

you know as I've mentioned

we are you know

constantly looking at our processes

and trying to figure out

how we can

you know make them better and better

you know as an organization

you know as we've grown

you know things

you know need to adjust

we today are doing it quarterly

and the quarterly aspect of like

walking the stores

by no means meant to be like

that's the only time people do it

but that is the time where

you know we're looking for like

update your scorecard

and you know share the information

in a dashboard

where

you know everybody can see

and that is

feeling right now

to be the right cadence

because

that's enough time

that you know there can be

you know material differences

made

and so you can see

and kind of like the scores evolve

over time

but also frequently enough

that

you know you're not missing that

perhaps

you know there's been a setback since

but of course my real hope

is that is happening

you know they're happening

weekly

just perhaps in different parts of the organization

I want to ask a couple more questions

so that folks can try this at home

I was just thinking like

this podcast is the opposite of

don't try this at home

it's like here

do you try this at home

try it at home

yeah

so I want to try to

give people

a few more answers to questions

when they're probably going to try to

do this

themselves

so who's in these meetings

like do you join these walkthroughs

does like David join

what do you suggest there

yeah

so what for

what we're doing for each team

is they do them

themselves together

so

bare minimum it should be the engineer

product manager

and designer

doing it together

and the reason why we like to see

it happen together

is again

as we've talked about before

is that like people bring

a different perspective

to something

and so let's say

you know somebody in the room

might be like

oh my goodness

you know that

like

that the load time

didn't feel really good there

and like

oh whoa that like

the way we're stating this

is not consistent per page

and ah

that's not on our design system

so

you know

it is really powerful to have folks

like come together and do it

and in fact

David Singleton

who you mentioned

he and I

do these things very regularly too

like this is like

kind of outside

the essential journeys program

but like he and I

walk the store

and we'll just pick random flows

and go through it together

and you know

I can't code

but he can

and so he'll like

he'll do the code part

and I'll be

you know sitting there being

what

you know do they really do that

like you know

can we

you know

how can we make that better for them

and so it's

I really love the multi-disciplinary

approach

but then when we do the calibration

after the team has done

these walkthroughs

and they've kind of gotten their own

perspective

and they you know

fill out the scorecard

based on our rubric for quality

we will come together

in what we call PQR

product quality review

and they will take us through

what they have

you know

experienced

and

then they'll talk about

like and so this is why

we've scored this

a yellow

or a yellow green

and

and then we might have a

you know

conversation about that

it's like

well actually

like that felt

a little worse than

you know

you've described it

and actually

like I think that

you know

we probably need to

put more urgency

on solving that

or in some cases

it's like

actually like

that was pretty great

you know

if you think about

you know

what we're

we're trying to

you know

help somebody achieve

at this moment

like that actually is

is really

you know

hitting the mark

and so we will

debate that there

and in those meetings

you'll have

yes myself

David Singleton

um

Will Gabrik

who you know

leads product and business

and then various leaders

from the organization

that might be relevant

to that area

we are trying to give people

kind of like

insight to what's

happening across

so

again

it's a multi-disciplinary room

trying to keep it

you know

not too

too large

because obviously

it can be

hard to have discussion

but it is

very valuable

to make sure again

that we have

you know

the perspective of

product marketing

and the perspective of

engineering

and expected

product in the room

as we discuss

what our quality bar is

awesome

okay

that makes a lot of sense

in terms of scoring

are you scoring

individual steps

of these journeys

or is it

yellow

for like segments

what are you scoring

the way the rubric works

is so that

and we

we have a template

for the friction log

so

people fill out a friction log

and it'll be like

screenshots

and then what they experienced

and then there

is a

you know

kind of a tool

the tag

for each

kind of moment

it's like

oh

that was a nice touch

or

oh

that is

you know

not great

we should consider a fix

or

different levels

of kind of severity

of like

oh my gosh

p0 bug

we need to fix this right now

so they'll

they'll tag

for different moments

in the journey

and then

there is a

summary score

at the end

which is

based on a rubric

that we have

that talks about

you know

the importance of quality

from the point of view

of usability

utility

desirability

and you know

actually going to that next level

of surprisingly great

and then we'll ask them

to score on a whole

what they felt of these things

and then that

adds up to a summary score

which we have

also talked about

the different ways of scoring

you know

is it a number based system

is it a letter based system

like A9SB

yeah

we have so far

we have landed on

color system

because

honestly

I think people can get a little

tied around the axle

on how you're measuring it

and like to your point

and like

especially in subjective things

and it's just like

oh you know

it's like

well is it really

at six

or is it a seven

and you know

we didn't want people to get

a little too

too worried

about

you know

how does

like it's not meant to be

an objective

quality

quantitative score

it is qualitative

it is judgment

we hire people

for judgment

you know

so we want

you know

them to bring that

to the conversation

and so

that's

you know

how we chose the score

because we felt

that would actually

lead to

you know

quicker

but like

straightforward

opinions and decisions

at a lot of companies

you have these reviews

and the founders

like share all this

like oh this is broken

this is busted

and as a product team

you're like god damn

we have these goals

we got to hit

we have this roadmap

and now we're going to get

a hundred things

that the founders like

got to fix this

I'm curious just how you

and tell teams

to take this stuff

and prioritize it

amongst all the other things

they're going to do

is it just up to them

is there like

need to fix this

anything you can share there

but just like

had actually operationalized

taking this feedback

and doing something with it

yes

yeah I've seen some

organizations

talk about

you know

when they're doing

planning

you know

you do your

OKRs

for quarterly

or half year

or year or whatever

recommendations of like

10% of your time

should be spent

on you know

fixing things

and 20%

on growing things

and the rest

on you know

keeping the lights on

whatever it might be

so yes

I've seen different companies

you know

build a recommendation

based on certain percentages

of how they think

teams should be spending

their time

and we at Stripe

think that

you know

first and foremost

is that

you know

we have to

make sure that folks

are number one

you know

hired

with that fact

that they have

great judgment

and care

for what they build

and they take pride in it

like you know

that's like number one

and then

you know

you can give a lot of trust

to people

based on that

that kind of

commitment

to building great things

that they will use that

in their decision making

and then of course

it needs to be very clearly

advocated for

at the highest levels

of the company

and with that

I think that kind of like

fuels

people's thinking

as they're building

their plans

but there is iteration

in the plans

and we do have

multi

multi-disciplinary

people

you know

making

the plans together

so it's like

oh okay

are we advancing

these features

are we

are we going to be

building growth

and you know

is that

you know

improving the quality

as well

and so I think

that's how we kind of

together get to it

but we don't have

there's no formula

that we ask people to

so basically

what I'm hearing is

it's the cultural

kind of just everyone

people are hired

with this expectation

and we are going to

focus on quality

and we'll prioritize

things

even though

they may not

move metrics

because we know

that this will

generally improve

and grow the business

part of it though

is

showing how it moves

metrics

because I think

that is

a dangerous

belief

that is

absolutely out there

as we

we talked about earlier

but that

actual quality

improvements

do increase growth

they do improve

the bottom line

right that like

you know

for example

we you know saw

that folks were

reaching out to support

because

they didn't know

the state

of how

you know

one of their

invoices

was performing

and what we

when we dig in

we realized

just like

well we had a button

that like

looked nice

but it wasn't super clear

and so

they didn't know

how to access

the thing that

they were trying to do

and so

by improving that

we decrease

the need for them

to have to reach out

which is clearly

not their

you know want

to have to call somebody

they you know

find the answer

to their problem

and so with that

we made an improvement

and we of course

improve

the bottom line

because of that

so I actually think that

maybe

in one of the steps

that somebody should

consider

and the organization

is just like

you have those examples

like every company

does

where you know

quality

leads to

better business outcomes

and

to talk about those

and make them

known

because I think it's

actually a false belief

that

you know it's like

one of the others

like are we going to

work on quality

and it doesn't move the

metrics and

and

where we do

and some of them are

longer term

and so you have to look out

for a while

to see that change

and you know

the beliefs of your customers

or you know

how often they're

they're sharing your product

or how often they're

succeeding

and what they're trying to do

but some of them are

short-term impacts

and that is

an important thing

for people to be aware of

because

it will give them ideas

of like

oh we could do this

in our team too

we could have a

higher quality product

and actually move

the business metrics

is there anything you do

in how you

evaluate performance of

teams

that helps prioritize

this sort of thing

so generally

it's just like

cool this team

moved this metric

by a ton

they're doing great

I guess is there

anything that you bake

into performance evaluations

at Stripe

especially for

product teams

that help them

understand

and prioritize

some of these things

that may not

obviously move metrics

other than just broadly

we believe

great experiences

are going to improve growth

yeah

well I think

one part

is being clear

on what impact means

because I do think

that in some companies

impact

there's like

okay

what business metric

did I move

and how much

and there are

certainly

really important

impact

projects

that folks can have

that maybe

they're multi-quarter

multi-year

and so

maybe you didn't move

this incredibly

important business metric

in one quarter

but actually

like the work

that you are doing

is instrumental

to the success

of the business

so there's that

and then

like you said

there are

perhaps

quality efforts

that are harder

to measure

or their longer term

but they are still impactful

so I think

number one

is that

you know

when you're thinking

about how

to come up with

the rubric

for how you're

going to judge

performance

is just like

really honing in on

what

what does impact me

and

and then

a lot kind of

comes from that

and being able to

celebrate

and recognize

great work happening

even when

you know

it's not necessarily

materially moving

that number

and

the other part of it

is we have

a levels

and ladder system

so it's a

document

that's not meant

to like

lay out

like here's the checklist

of all the things

you need to do

but it's

you know

kind of a guide

for

this is what is expected

in your role

and at this level

and in these

documents

we talk about

the importance

of things

like quality

in that

that you know

what we pursue

is building these

you know

things that

are great

and

another part of that

is also

the operating principles

which is kind of like

the thing that we align on

underneath

all of these

kinds of levels

and letters

systems

that we have

and our operating principles

include

meticulous craft

it is one of the things

that is really important

to us

as an organization

is just like

having that meticulous care

for all that you do

like

whether it's like

you're

you know

designing the space

that we

work within

or that you're

creating the API

or that you're

building the interface

or that you're

you know

talking to people

on support calls

like the meticulous craft

is something that

you know is actually

expected of everybody

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slash leddie

I'm going to shift

to a different topic

and this is just the last area

I want to spend some time on

which is

team building leadership

that sort of thing

so you've led design

at three hyper growth

companies

two of them airbnb and striper

like two of the biggest companies

in the world

and also just known

for great design

and I'm just going to ask

a broad question

what have you learned

about building

leading

managing

scaling

large teams

are there lessons

that stick with you

anything come to mind

when I ask that broad question

one of the things

that has stuck with me

and you know

through all the trials

and tribulations of leading

and as I've already laid out

for you in the very beginning

of this call

haven't always got it right

but one of the things

that has like

been a clarifying force

is I think about

growing and leading teams

is actually something I learned

at airbnb

when we were there together

it's a formula

sort of

so performance

equals potential

minus interference

and I really like this

it's pretty simple

but like

is a good reminder

that you know

as a leader

one of the things

that you are

of course driving towards

is trying to get

better performance

you know better performance

so that you know

your team feels

you know more purpose

and motivation

and is excited

about their work

and that you're building

greater things

for you know

your customers

and you're having

more business effect

of course performance

but the key

pieces of that

of course is potential

so thinking about

how you increase potential

which would be of course

hiring really well

developing the talent

and helping them

grow and increase

their own potential

to do better

and greater things

and then

paired to that though

of course is decreasing

the interferences

which could be that

like kind of lead weight

on top of great talent

because you can hire

the best people in the world

but like a muscle

atrophying underneath a cast

if you know

there are interferences

that are holding them back

from doing great work

you know

they're going to burn out

they're not going to enjoy

the work

they're not going to be as

successful

then you will not get

as strong of performance

from it

and so I really do think

of this constantly

as to like

how can I increase potential

how can I decrease

interferences

and over time

especially as your company

grows

you know

you're going to have to

keep doing that

like you know

the design work

is never done

in designing a team

because the more people

you bring in

you know

the more it puts

your processes

in a faulty state

we

you know

intentionally

or I have intentionally

you know

run teams where

you know

you get to a point where

like it's

kind of like

running hot

right

it's just like

okay

like we've

outgrown our processes

and that's okay

because then you can learn

as to like

okay this is how

people are actually

trying to work

and

this is how we actually

can improve it

so

you know

making those changes

as needed

you know

helps to make them

you know

more

sought after

and

you know

more

informed

in terms of

as you

improve the processes

one of the things

that I've been

working on

since

I worked back at Airbnb

was this idea of

improving awareness

of the things that are

happening

what happens

at a lot of companies

especially as they grow

as people lose touch

with what's happening

in different parts

of the organization

and you know

everybody's got

like a doc that

you know

their PRD

where they've written down

what they've done

it's got like

tons of

you know

words

that nobody really

understands

and you know

keywords

for the

different projects

and that

isn't

you know

the best way

to lead to clarity

and

I'm a strong believer

that a picture

tells a thousand words

and

a prototype

tells

you know

saves a thousand

meetings

what we do

and I've been doing it

for the last

you know

I don't know

you know

decade or more

is

having people

within the design team

share

as a screenshot

or a prototype

of what they are

working on

in a shared deck

and so they add this

to a slide

and google

slide decks

and for you

a couple of weeks

and we get to see

what's happening

across the design team

and this is really important

for all the designers

because

they could see

you know

whether or not

they're a team of 10

or 170

or whatever it might be

what is happening

and they can say

like

oh my gosh

like you're working

on that surface

like

so am I

and

let's talk about it

or

oh that's an interesting

pattern

and like

you know

maybe we could use this

in more places

and

we send it

to

the product managers

and the engineer leaders

and the leaders

in the company

because it is

also a really great way

for them

to understand

what's happening

and

what are we building

together

because going earlier

is

I talked about

the importance of

thinking about things

as a journey

so like

what's happening

in the marketing side

what's happening

in the

you know

this aspect

of the product

and seeing

how all these pieces

really fit together

that has been

you know

absolutely

like one of the things

I will take where

you know

wherever I go

whatever I do

because

it has just been

like

very very

useful tool

I remember that

at Airbnb

and I

there's nothing more fun

than just looking

through a bunch of awesome

designs and products

that are in motion

and

in a deck form

is so handy

just

flip through

what's going on

around the company

and like

oh wow

look at this thing

that's amazing

and it's interesting

that ends up in a deck

like feels like

Figma would be really good

for that too

but

but somehow

decks are still really

really handy

for simple things

like that

and one of the key pieces

is just like

keeping it

really low maintenance

yes

you know

the design team

would definitely

prefer that

it would be in Figma

but I

you know

critically

I

want all functions

to be able

to look at it

and

you know

if

not everybody is on Figma

and you know

if they were

that would be great too

but if they are not

you know

it's just like

flipping through

really easy

touch up a button

you know

you can just like

send it off

it's behaviors

that people are really

used to

commenting

but

yeah

maybe one day Figma

and the way you do that

is it's just like

a scheduled call

for all designers

add your stuff

to this deck

and then you email it out

every two weeks

I think you said

yeah

yeah we

and we experiment

with like

how often

we ask folks to share

and also like

you know the granularity

of what they're doing

like it is not meant

to be a status check

we're not asking

everyone like

show us what you're doing

it's more of like

what are the projects

that are happening

and you know

we might ask

like

we'll show us

like the medium

and large projects

you know

if there's such

just too much going on

and all of a sudden

it's like a 200 page deck

and no one's going

to flip through it

so we have experimented

and evolve that

depending on the team size

and I think right now

we're at monthly

sharing of it

and that seems to be

working pretty well

it used to be bi-weekly

which I loved

because I really love

looking through

but it ends up

you know

if it's

you know

feels like

it's a arduous task

then you know

it's not succeeding

yeah and especially

knowing designers

they'd want to make sure

it's the best version

of what they've done

and then it takes

all this extra time

to like

okay we got to

make this beautiful

mock

yeah

you know and we're actually

another part of it

that you know

is another benefit

of you know

opening up

the curtain

a little bit

of like we

you know

we do

you know

certainly we have to take

things seriously

in terms of like

you know

it's confidential work

it's work in progress

you know it's not ready to go live

you know

we're not ready to

you know

critique all the details

about this

like

you know

we do need to make it

very clear to folks

that this is

like work in progress

but also

you know that

it

it is

really beneficial

to bring the work out

because

what isn't great

is that you get to the end

of the project

and people have worked

tirelessly on it

for some

long stretch of time

and then find out

that like

oh my gosh

this is the same project

that we're

doing over here

and you know

this can be completely redundant

or like

these two things

are on a path to collide

so we want to know that sooner

because it

absolutely in the end of the day

will make the work better

save time

and so

you know

opening up that curtain

and showing the work in progress

you know

it can feel

hard at first

but I think people

have started to see

the benefits

and doing that

and then

you know

usually that

will lead to better outcomes

and they'll all run

in the culture too

Going back to this

formula you shared

which I love

performance equals

potential minus interference

is there an example

that comes to mind of

helping with interference

where you

found that

oh wow

this is really slowing things down

and

you change something

it actually goes back to org design

that we talked about earlier

and where people sit

so when I joined Lyft

as I mentioned to you earlier

I was like

oh I had learned

from the experience

that I had at Airbnb

and I came in

and you know

needing to transform the organization

and was

hopefully much better at it

because I had learned so much

what actually

was going on there

is that

the

way that the team was organized

before I got there

was that actually

physically

the design team sat separately

they sat in a room

that was just like

beautifully designed

separated from

engineering and product

and all the other functions

by a locked door

and

that was really interesting to see

because of course

there were a lot of benefits to it

which is that like

design

you know

had this like

very safe space

for creative discovery

and exploration

and communication

there was

you know

work all over the walls

it was like

wall to wall

whiteboards

and it was just like

absolutely a place

where creativity could thrive

it sounds exactly

like the Airbnb situation by the way

the current Airbnb situation

the original

the fair

fair times

yeah

yeah

yeah

and you know

absolutely

there are a lot of like

tie-ins to

you know

what I had seen

and the

interesting part about like

how you know

actually teams were working is that

you would see that

there was like

a lot of wasted work

and there was a lot of like

misalignment

in what we were trying to do

because there was

you know

product managers

and engineers

that were sitting alongside each

other

making decisions

and talking about the work

and deciding things

and then designers

were sitting over here

in this other room

and they were working on something

and then they like

you know

they'd meet up

and just like

well

that's not aligned

like

no

that doesn't fit the goal

and like

what

you know

you went that way

we were supposed to go over this way

and so

you know

interference

in the sense that it was like

it was wasted work

it wasn't actually aligned to the goals

it was slower

and you know

there were definitely benefits

like there was real reasons for doing this

and I know there are companies

including Apple that have

you know

kind of like separation of these things

but I think

if you're going

into that kind of way of working

you know

there's probably a lot of other decisions

you need to make too

in terms of the way the teams work

and so what

I was seeing there was just

you know

it's kind of like

the composite of all these

you know

aspects coming together

that was not leading

to

you know

more efficient

and and less interference

and so what we did

was to evolve

the way we were working

and bring better alignment

to the different functions

and again

you know

had done it with

you know

an approach about listening

and you know

came into that with a

you know

kind of

better understanding

of getting to know the team

and getting to know

engineering and product

and see what our goals were together

so that when we were making changes

we were making the changes together

and we you know

actually were aligned

so that like

on the day that we

opened the doors

and you know

brought you know

design and engine product together

and and had you know

spaces for folks to like

work together

and like

they actually sat with each other

we still kept the creative space for

you know

this is where we'll do crits

this is where we'll do working sessions

this is where the folks that

don't work

in an embedded fashion

will sit

but we had like

you know

the best of both worlds

in that way

and so with that alignment

of the way that the

the teams were working together

there was much like

faster kind of

iteration cycles

better clarity

on how the work was working

and we still kept and protected

you know

that room for creative space

like literally the room

and literally

the room in terms of like

figuratively speaking

for allowing for

in creative exploration

but more aligned

and just to understand

essentially you

re-orged the teams

and not just

physically

move people

but you kind of changed the way

the product and design

and engine team

was even organized

yes

yes like literally and figuratively

we broke down the wall

and you know

brought the teams

physically together

so that they would work together

and then you know

we had an org chart

where it's like

okay

these designers

are working on driver

these designers

are working on rider

these designers

are working on

you know

it's the safety team

and then they would

sit with their

respective engineers

and product managers

and then

you know

we would

as I talked about earlier

like we would come together

at key moments

to make sure that

we as a design function

we're still

you know

aligning

on you know

shared goals

about

you know

the overall experience

but also

making sure that

we could work well

with our partners

so interesting

that that was a

recurring pattern

at the places you went

I imagine Stripe

was not like that

there was not

all designers

sitting in that

locked room

not in a locked room

and I joined Stripe

it was a zoom universe

so it's

a little bit different

but you know

we do

even today

we have

you know

a studio space

where you know

we have all the

great you know

tools of craft

and when you do

go into the offices

we do have places

where you know

designers sit together

especially in the functions

that aren't embedded

so we do have

for example

we have brand

and marketing creative

we have the

the website team

and

we have

you know folks that

work kind of

across all of the things

that we do

and so

you know

for sure

there

there usually is

some sort of

creative space

which

I actually think

like having a physical space

for creative discovery

and exploration

and you know

having that up on the wall

like you know

I love that so much

and you know

I go into the office

about half time now

and you know

I think over time

we'll probably build out

more and more

because it is really powerful

in addition

to having teams

like sit by

the disciplines

that they work with

every day.

It reminds me of a quote

I have on my wall

that

I think I found in the

Rick Rubin book

but it's by someone else

so I don't know exactly

where I

found it

but it's a

the object

isn't

to make art

it's to be

in that

wonderful state

which makes art

inevitable.

Ooh that's good

I like that very well.

By Robert

Henry.

Okay

by Robert.

That's what I try to do

in this little

podcast

studio that we got here.

That's awesome.

Is there anything else

that you

think would be useful

to share either

from scaling

design teams

or broadly?

I think one of the other

tendencies I see

of companies

at different stages

of their growth

is

a fear of bold ideas.

What happens

is that

it can happen

at small sizes

and then it can happen

at large sizes

actually.

It's just that

a fear of

kind of like

shaking things up too much

or big ideas

with lots of things

changing influence

are really hard to measure.

And so like actually like

you know if we just like

make an incremental approach

it's very measured

and we can

we know what the outcome

is going to be

feel safer.

You know I can get it done

in the quarter

and depending on how

your performance is managed

that might be more attractive.

And so

that is a

dangerous tendency

because I think if we go back

to like

what quality means

you know and you think

about it as like

well like

quality is really

you know your users

are the judge of that

and the way that they

experience things

oftentimes

are like across products

across surface

across time.

If you just think about

you know these like

incremental approaches

to the little

you know to the scope

of whatever that is

that you own

you are very likely

not to like

make the

the whole thing better.

So I think we have

to fight against that

and you know

the way I look at it

is you know

the way I talk about it

is like

reach

reach for the stars

and land on the moon

and what I mean by that

is that

vision work

is really important

and I think like

sometimes you can get

a bad name

because you can end up

with some folks

that are doing vision work

that goes nowhere

and they make a beautiful deck

and then it gets like

seated on a shelf

and nobody ever builds it

like that is not

what I'm talking about here

that is not

what I recommend

but actually

you know vision work

that absolutely does

look at the

you know

the entirety of the experience

a comprehensive approach

and you know

a journey approach

and thinks about

how these things

you know various things

may come together

to be better

and like

sketch out the

ideal version

and I think

Brian Jesky talks about it

I think it was

like the 11th star

experience

I think you once said

let's listen to white stuff

that we talked about

a couple of times on this podcast

yeah

looking at it as a journey

yeah like

it's not the five star approach

it's not the six star approach

but like

the 11th star approach

where they go

show what that ideal version is

like because

if you don't know

what that is

like

what are the chances

that you're going to

increment yourself

to the right

outcome in the end

and

you know as I talked about

before

like building the house

like you want to see

what that picture looks like

in the you know

the you know

how all these pieces

come together

and I strongly recommend

you want to see what it looks like

in you know

an ideal form

because you're going to

always work back from that

and so it's like

okay if this is what we want to get to

this is what like

our product is going to look like

in two years

how do we get there

and what very likely is

it's a team effort

and various parts of your

organization

are going to have to own

various parts

and you know

maybe we ship this piece first

so that we can study it

and learn

and you know

make sure that the data is good

before we move to that next piece

like I'm not suggesting

you have to ship

the whole thing at once

but that like

you know kind of

North Star

lays out the process

in a way that I think allows for

you know

big risk-taking

in a way that is measured

and thoughtful

and you know

actually also

feels like progress

as you step towards that

versus like

you know

trying to like

get there

you know

day one

and you know

likely

you know

end up

giving up

I love that

reach for the stars

land on the moon

that could be a

metaphor for so many things

let me try to squeeze in

one more tactical tip

for people listening

if someone's hiring a designer

so someone that's not a designer

you know

just founder

or product team

just like

what should you look for

that may be a red flag

or something that you want to look for

to kind of feel good

that they're going to be a good fit

the key

I think to keep in mind

is

you know

it's easier to teach tools

and process

than it is

taste and character

so I would certainly

you know

pay a lot of attention

to that

you know kind of like

their hit rate for

you know

great judgment

in

in great taste

and how they've honed that

you know

even if

you know

they're not very experienced

like

just to like

see

do they have that

you know

natural inclination

for great things

the other piece of it

is that

you know

certainly

you want to find somebody

with great talent

for sure

and high craft

but you also

want to find somebody

that's humble

you know

that like

folks that are really good

at what they do

aren't always

but

humility is a really important part

I mean

I think it's a really important part

for anybody on a team

because

you know

if you're working on a team

you know

you need to work together

and

it is important that they have

that respect and empathy

and understanding

and

you know

enthusiasm

for the folks around them

but also the users

so

you know

humility means

that they're going to

pay more attention

to what

the users are saying

and hopefully be curious

about what's working

and what's not

and you know

strive to

navigate these things

to make it better

and then I guess

the last piece

would just be

you know

hustle

or

or hutzpah

I'm not sure exactly

what's the right way

to put it

but

you know

the

design

and you know

the creative functions

is

you know

it's the act of creation

and

it's scary

you know

it's like to like

take a blank piece of paper

and

propose something

that you think is better

it's

scary

to

you know

have the courage

to say

this is not good enough

and we should do it again

is scary

and so

having somebody

that has

you know

that kind of

like courage inside them

to

you know

fight for great

is pretty important

and

that hustle

to like

try to

execute on that

you know

rapidly

is of course

essential

as you're

you're hiring

at really

any stage

company

and I guess

lastly I think

you were asking

in particular

like

is

you know

especially with younger

companies

who are startups

you know

I think

one thing that can be hard

is like

do you hire

a

you know

more junior doer

or a more senior

you know

kind of like

thinker or operator

you know

it's like

if you had all the

in the world

like

all of it

but

I do think

in your early stages

you probably do need

a doer

but it is important

to also have

that kind of lens

of

you know

how do you

build an organization

that's user focused

and the way that they

operate

and the way that they

work together

and bringing

you know

a strategy

that will

help to be

user focused

from the start

so

you know

maybe a great way

of doing that

is kind of

having like a more

you know

senior leader

design advisor

and then

a you know

kind of

executor or doer

you know

full-time on the team

that's a really cool tip

on the craft

and taste

piece

a lot of times

people don't

have that themselves

necessarily

any tip

for how to

measure that

is there

I don't know

a book

you'd recommend

or

trick

or is it just

trust your

trust your judgment

and like

does this feel

great to you

it's contingent on like

what is the thing

what is the user need

you know

so something that

you know

is is really great

like

we do

a lot of tools

that like

we strive

to make them power

tools for our users

and a lot of times

that means

like dense information

that of course

is like

still you know

easily accessible

but you know

we'll definitely

feel different

than perhaps

you know

a consumer product

that is meant to be

extremely

you know

light and sparse

and you know

directive to like

one individual

thing at a time

so it really kind of

depends on the context

of the product

sometimes

so that's why

it's hard to kind of

quote an individual book

but yeah

I mean I can think on it

and we can put it

in the show notes

there there are

definitely books

that talk about like

the principles of great design

and we can look at that

amazing

willing to extra books

that come to mind after

one other question

I wanted to ask

is what's

a favorite project

that

y'all have worked on

at Stripe?

Oh yeah

we get a good one

that I'm so excited about

we

well first off

I don't know

if everybody knows this

but Stripe

prints books

so Stripe Press

we print books

that are

we consider

of ideas of progress

it's

you know

our intention of

bringing great ideas out there

they don't

all have it

you know

most of them

don't have anything to do

with financial infrastructure

it might be

any number of

interesting

problems

and opportunities

of things

and ideas

that people have talked about

I have many of them

in my background here

I'm a

huge fan of Stripe Press

nice

and we take great care

to

you know

kind of like

deliver these ideas

of progress

in books

that hopefully

feel beautiful

and

we have a new book

coming out

that you can pre-order now

and it is

Poor Charlie's Almanac

and so it's actually

I already pre-ordered

you did

I'm so excited to hear that

I'm really excited for it

it's

it's a fascinating book

and it's

20 years old

it's actually

Charlie Munger's

words

but

Peter Kaufman

a friend

and a colleague of his

assembled

all of these documents

over the years

of things that

you know

Charlie had written

and said

and put it into this

kind of like anthology

and so this book is

really fascinating

and it's not

you know

it's

not really a linear story

so much

and so

we have

reprinted this book

uh

we also have

we created a teaser site

that I strongly recommend

you all check out

it's

oh man

it's

unreal

I remember

that when you

launched that

I was like

just keeps going

and gets

crazier

and wilder

and amazing

I don't even know

how that's possible

on a

on a website

it's

it's pretty awesome

and that's

uh

our website team

is just like

as you know

we talked about

the importance of

like design

and engineering

working

super closely together

and it's just

just like that

and wild

you know

that art and science

coming together

into something that

you know

hopefully is

is fun

and engaging

and people want to

you know

pursue it

and

so we're working on

that the book

will be coming out soon

and we're working on

an update to the site

that we're

really really

thrilled about

so you can

you know

kind of

read the book

online

um

and it really

in a special

kind of way

so yeah

very big fan of this

what's the website

for folks

that you happen to have

that you're

all otherwise

we'll link to it

in the show notes

for you

yeah

yeah

it is

uh

press.stripe.com

will be

where you can see

all the books

that we have

at Stripe Press

and I believe

the first one

in the line

and actually

what you'll see

in the

the website

is that

you know

we originally

had a kind of

like

you know

typical

buying model

of like

the squares

outlined

and

one of the things

that you know

we sought to do

with the website

is to kind of

consider like

what would be

you know

a great experience

for understanding

different books

and like

when you go into

a bookstore

like you see

like

you know

the the

spines of the books

and you

you know

kind of pick them up

and you turn them

around

and you look at them

and so that's

actually what you

will experience

I mean

I should stop

describing

it just go

and check it out

and you'll see

as we

we sought to

deliver this work

in a way that

you know

would be

aligned with what

a reader

would want to pursue

I can't help but ask

but how did that

even come together

was it just like

this passion project

of like

oh this book's coming out

I just want to

invest a bunch of time

resources into this

or is

how does that happen

at a

at a stripe

yeah

well

I mean

a stripes mission

is to increase

the GDP of the internet

like we

you know

we strive to build

global economic

prosperity

because

you know that's

greater access across the globe

but there's more ways

to do that

than financial infrastructure

financial infrastructure

is absolutely

a major part of that

right

and it is like

kind of like

the lifeblood of businesses

and it enables them

to accomplish more

but this notion of

like ideas of progress

is another angle

into that

so while it might not

be our core business

it is very much aligned

with our mission

and so

yes

it takes time

but we feel that

it's important

for what we're

setting out to do

and it also

relates to

you know

the pursuit of

you know

creativity

and excellence

it is a part of

you know

our identity

it is a part of

you know

who we

we

feel we are

or we strive to be

and you know

we're excited to

share that with people

so you know

in part

it's like

in some ways

like

how they get to know us

and they get to see

you know

the care

that we put into

you know

any number of things

Katie

is there anything else

you want to

share

or touch on

before we get to

our very exciting

lightning round

we talked a little bit

about

you know the

importance of

different disciplines

and the

you know

kind of importance

of

quality being

a group effort

and you know

I

I hope this doesn't

insult my function

as I say

but like

at the core

design

is

is simply intention

bringing

attentionality

to the decisions

that you make

and thinking about

you know

who is this thing for

so like

if you're designing

a doorknob

let's say

and it's like

okay just the doorknob

speak to

whether or not

I'm going to push

or pull

or turn

is it

comfortable in the hand

is it easy to manufacture

is it easy to put on

and remove

you'll see

these are some of the

intentional decisions

one could make

whether or not

a designer

an engineer

the product person

any old function

can you know

put that intentionality

if you think about

like

who is impacted by this

who is using this

that literally could be

anything from designing

a doorknob

to designing your org

structure

to designing your strategy

now obviously

great design

is also creative

and it also

is demonstrated with great taste

you know

for what is beauty

and so of course

that's where

you know

I would say that

like design expertise

with people that have these

you know creative skills

and these great tastes

is you know

an incredible

important thing

to you know

bring into the organization

but I think

you know

day one

everybody can bring

more care and intentionality

and I think that will result

in better outcomes internally

and externally

in the long run

like your podcast

is a great example

of great craft

and great quality

like your

you know

I would

I was just saying this

to my husband

the other day

as I was talking about

doing this

and it's just like

your podcasts

there's like

more usable learning

per you know

minute

than you know

most

I don't know if that's like

a metric

that you're measuring

but like

I love how you don't have

your guests

tell about their background

right

because like when someone tells

about their background

like that is interesting

but like

it's not really like

usable information

of like

oh I can take this information

and run with it

and then bring it to my own team

and make my work better

and so like

you have clearly thought about

that

well I don't know

if that's why you made

that decision

absolutely

that is a great way

okay okay

that's great

and I also love

you know

the way that you

you set these things up

you know

you had said to me

you know

in the thing that you set me

just like

if it's not good

we're not going to ship it

and you set it in very nice

ways by the way

but like

at first I had this like

oh gosh

like

if it's not good

what if it's not good

but I also had this moment

of like

oh well that's pretty great

because

if it's not good

he's not gonna

you know embarrass me

to the rest of the world

hopefully

and I love that

because that was that

courage

that I was talking about

earlier too

of that like

you're not gonna let

that go out

because

you know

that

each one of these little things

will end up

you know

leading to

a belief

of the

level of quality

of what somebody

you know

can

rely on getting

when they listen to your podcast

and you know

again

like

one workout

isn't going to be a six pack

but like

every one of those things

you know

will end up leading to

better

you know

quality overall

so

kudos to you

you're nailing it

so great

wow

Katie

what a nice way to end it

I really appreciate that

that's exactly how I think

about it

actually you cracked

my whole strategy

of just

making it as

concretely useful

as possible

I was actually on

David Perrell's podcast

recently and

and he

had this really good way

describing this

which is exactly what I've

tried to do

but I haven't put my words into it

of

make it as

useful as possible

per minute

without

removing the humanity

and I

realized that's kind of what I do

is like

you know

I could cut all the stories

of everyone's backgrounds

but that's

that's

that sucks

so it's just

optimized for value

and

concrete tactical advice

also make it

fun and human and interesting

yeah

so

thank you

for the kind words

and

with that

we reached our very exciting

lightning round

I've got

a number of questions for you

are you ready

I'm

ready

let's do it

let's do it

what are two or three books

that you've recommended

most to other people

one

how to win friends

and influence people

it's an oldie but a goodie

I forget how many years old it

is

but many many decades

yeah I think it was like

in the 1930s

but yes

I mean the cover is funny

you know

you might be embarrassed to

read it on a bus

I don't know

but

the learnings from it

you know

are timeless

and I've actually read it

four times

and

I'm gonna

always do for another

because

it is a great reminder

of just like

how important

the way you articulate things are

and you know

not a

you know

negative or gross kind of way

but like

people care first and foremost

about themselves

like

that's the body that they are

within

that is the context that they are

within

and

recognizing that

you know

I think can be really powerful

as you think about leading teams

as you think about

working with other people

as you think about being

a good spouse

like whatever it might be

so

a big big fan of that one

the other one is

a newer book

I think actually

I was still a couple of years old

it's about the Wright Brothers

by David

McCall

I think

I've been learning how to fly

and so like

I'm very obsessed with this

but like

I think it's a book

that's relevant to everybody

especially

even

on

Furnors

because it just like

kind of talks about

the

impossible challenge of like

nobody thought it could be done

you know

even

you know

the American like

Institute of Science

like didn't think it could be done

and you know

these individuals

that had the like

resolve

and the commitment

to

you know

make it happen

and I think also the power

of this like

beautiful partnership

of course

the brothers

that doesn't always mean

you get along

but they

their brotherhoods

and they

you know

they did so

and

it's a beautiful story

so

big big big big

big fan of that

and then

third book

I would just say

is actually

I brought it over

because I knew

you were going to

ask me this question

I don't know

if you could read that

but

the boy

the mule

the fox

and the horse

this book was given to me

by Jenny Arden

which

I think you may know

it's wonderful

it's a beautiful story

it's like

you know

it's

make you laugh

it's

you know

it teaches you

a thing or two

and

you know

one of the

best quotes

in it is

one of our greatest

freedoms

is how

we react

to things

very roots

yes

awesome

what is a recent

favorite movie

or tv show

that you really enjoyed

Oppenheimer was amazing

and tv show

shrinking

and

that one was really good

and it actually

really surprised me

how like

funny

and like

positive it was

because the

trailer for it

does not give that impression

but

it was really good

sweet

I've not seen that

what is a

favorite interview question

that you like to ask

candidates

tell me what

work you're

are most proud of

and the reason I ask that

is because

well

it helps me understand

their taste

and their judgment

what motivates them

what work they view

as good

and as a good outcome

it also helps me understand

a little bit about

you know

what they like to do

and where

you know

they're

kind of like

gravity pulls them

is their favorite product

you recently discovered

be a nap

or physical thing

anything

yeah

well as a parent

you should definitely know

the Tony box

oh I don't know this

the Tony box

so good

the Tony box

I should have brought it over too

so it's a

it's like a squishy box

but it's a speaker

and your kids can control it

and the way they control it

is these little figurines

I mean this is also like

a brilliant product

because you want to buy

all these figurines

but

the little figurine

so it could be like

you know

Belle from Beauty and the Beast

or like Elsa from

Frozen

and you know

they place the figurine on top

and that activates

the stories that this book

the thing reads to you

or the songs that it plays for you

you can record your own voice

so that you're telling stories

to your child

and they control it all

by themselves

and they can drop it on the floor

and it's all good

but the Tony box

pretty awesome

it just texted my wife to

check this out

amazing

great

very handy and timely

do you have a favorite life motto

that you'd like to

share

come back to

find meaningful

I don't say this out loud

but I do

I've had it as a post-it

like in my jewelry box

and that I

you know see regularly

tomorrow

is today

and what I mean by that

is that

so often

you know

I will like

in my head

be like

oh I'll do that tomorrow

like oh I'll eat better tomorrow

oh I'll think about that vision tomorrow

I'll you know

communicate better expectations tomorrow

and you know

it's kind of like those like

joke signs that like

free beer tomorrow

because you know

very easily tomorrow

just always moves on

and I needed to run

mind myself

that like you know

it's actually

it is now today

tomorrow is not that one

I feel like I need to

take all these

mottos

which are amazing

I love this question

that I just invented

and just put them all

my wall here in this office

yes

that's a great idea

you should make a book

look of letting go

oh man

the tribe of mentors

version of

Lenny's podcast

that's awesome

is there a lesson

that your mom

or dad taught you

that has really stuck with you

especially as a newish parent

yeah

I think about this a lot

I am a mom of twin girls

and you know

I feel so lucky

that my parents

raised me to see that

accomplishment

is based on merit

and hard work

and they never made me feel like

you know

because I was small

and that I was not as strong as

you know somebody

whatever it might be

that I wasn't able

and so like

my dad had me

you know

chopping wood

and mixing cement

as a young kid

and you know

that certainly led me

you know

in one part to be a designer

but also

you know

to be able to pursue leadership

and be you know

even though sometimes

I'm comfortable

like willing to be in the room

where I am vastly outnumbered

by people that you know

don't look like me

and you know

wanting to

or just like

not letting that hold me back

and I actually

I thought about that the other day

because I was riding in a

lift to the airport

this was also at like

4 a.m.

so it was like

really hard time to be in a lift

to go under the airport

and the driver was telling me

about his kids

and actually he had twins

it was one boy

one girl

and so we were talking about twins

and he's like

yeah yeah you know

like my girl

she's my princess

and you know

I you know

my son doesn't understand

why I don't let her take out the garbage

and like

why her job is to sweep

and you know

that's his job

he's like

I'm not gonna let her take out the garbage

like

and I was just

was sitting in the back of the car

wondering like

should I tell him like

you're screwing it up

like no

like just because

you know

she's a female

doesn't mean that like

she's not you know

able to do the jobs

even the hard ones

and even the bad ones

like taking out the trash

and you know

I really do think that

I'm so fortunate

that

you know

that was never

the way that my parents

were looking at it

and that

you know

now

today

I feel like

that is very much

a part of

a little bit of my

hutzpah

and willingness to

you know

kind of like step out there

because

I you know

hadn't been held back from those

hard jobs earlier

beautiful

final question

you mentioned that you fly planes

and this is my

actually related to my last question

I guess one that's

I was gonna ask if that's true

you mentioned it is true

is

is there a lesson

that you've taken

from learning to fly

and flying

that you can

that you've brought into

product leadership design

anything come to mind

yeah

first of all

learning fly

has been

such an amazing experience

because

there haven't been many things

in my adult life

where you feel

like yourself going

from like

knowing nothing about something

and

like being able to do something

and it's just like

what an incredible

kind of journey that is

and so

whether it's like

you know

learning a language

or whatever

like that

that is awesome

and highly recommended

but

no

one of the key things

that is definitely sat with me

from the experience

of learning how to fly

that I

definitely thought about

how to bring it into my work

is that

when I was

kind of

getting to the stage

of being able to do things myself

so my instructor

is sitting there next to me

and

you know

usually he's right there

at the controls with me

so if like

something goes wrong

when I'm

you know

flying

that he's right there

and

I remember

the

you know

one of the first times

when I was

like learning how to land

where

he moved his seat back

and like

like a lot

and so like

he was now like

kind of out of touch

for the controls

like he could jump there

if he needed to

but like

he really pulled back

and it was

such an incredible

like

visceral experience

I was like

he trusts me

like

in like

right now

he is like

he is showing his faith

in me to

take this

and like

take this challenge on

and I think about that

all the time

it's just like

you know

how can I show

you know

my team

people I work with

like

my support

and trust in them

you know

to take that challenge on

and so like

you know

I can't always move my seat back

but like

what might be the way

and so that's been a

you know

pretty

pretty great example

of like

something I want to pull forward

that is an awesome metaphor

I feel like this whole episode

is just full of

beautiful metaphors

also just full of beauty

Katie

thank you so much

for being here

two final questions

working folks

finding a line

if they want to reach out

and maybe ask some questions

and how can listeners

be useful to you

yeah

well first off

please do

you know

find me online

because

you know

as I talked about

like

we are in

the pursuit of

you know

trying to build

excellent things

and it's always a work in progress

and so I'm always interested

to learn

how others do it

and you know

see how we can improve

our own methods

I am

Lil

underscore

dill

on Twitter

and then I think

that name was taken

on threads

so I'm Lil

underscore

dilly

with a why

on threads

and then I'm Lil

LinkedIn

find me there

we're hiring

so definitely reach out

we

at our job board too

stripe.com

slash jobs

definitely check us out

we definitely

would love to hear from you

Katie

again

thank you so much

for being here

thank you Lenny

bye everyone

thank you so much

for listening

if you found this valuable

you can subscribe

to the show

on Apple Podcasts

Spotify

or your favorite podcast

also please consider

giving us a rating

or leaving a review

as that really helps

other listeners

find the podcast

you can find

all past episodes

or learn more

about the show

at Lenny's podcast.com

see you in the next episode

Machine-generated transcript that may contain inaccuracies.

Keywords

Stripe, design, quality, growth, teams, leadership, ROI, user experience, physical spaces, operationalizing, hiring

People

Katie Dill, Brian Chesky, Charlie Munger, David Perrell, David McCall, David Singleton, Will Gabrik, Jenny Arden, Frank Schätzing, Joe Botte, Rick Rubin, Robert Henry, Brian Jesky, Stefan Sagmeister, Jessica Walsh

Companies

Stripe, Airbnb, Lyft, Google, Apple, Amazon, Hertz, Shopify, Spotify

Organizations and Institutions

N/A

References

Warning: Undefined variable $clean_references in /srv/www/podtranscript.com/app/podcast_episode.php on line 376

Brought to you by Sidebar—Catalyze your career with a Personal Board of Directors | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | OneSchema—Import CSV data 10x faster

—

Katie Dill is the Head of Design at Stripe. Previously, she was Head of Experience Design at Airbnb and Head of Design at Lyft. Katie has been named one of Business Insider’s 10 People Changing the Tech Industry as well as one of Fast Company’s 100 Most Creative People in Business and received the Girls in Tech “Creator of the Year” award. In today’s episode, she shares:

• What makes a design great

• Advice on building high-performing teams in hyper-growth environments

• A pivotal lesson in leadership she learned at Airbnb

• Stripe’s focus on quality and how it’s tied to growth

• A formula for removing organizational friction

• How to increase productivity

• What to look for when hiring a designer

—

Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT.

—

Where to find Katie Dill:

• X: https://twitter.com/lil_dill

• Threads: https://www.threads.net/@lil_dilly

• LinkedIn: https://www.linkedin.com/in/katie-dill-79168b3/

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Katie’s background

(04:47) Katie’s pivotal leadership moment at Airbnb

(10:55) Advocating for design ROI

(16:07) Stripe’s quality focus

(17:50) Stripe’s vast scope

(18:45) How design enhances utility

(21:39) Defining beauty and its role in product growth

(26:19) Operationalizing quality

(28:44) Katie’s insights from dialogues with diverse organizations

(34:47) 15 Essential Journeys: Stripe’s method for holistic UX understanding and unified vision

(44:35) Stripe’s PQR quality review

(46:25) Stripe’s prioritization philosophy

(48:29) Measuring impact beyond metrics

(50:28) Performance = potential – interference

(54:09) Building and managing large teams

(1:01:46) Removing interference at Lyft: a practical example of Katie’s leadership impact

(1:06:10) Stripe’s physical workspace design

(1:07:41) Embracing bold ideas

(1:11:07) Qualities of great designers

(1:15:15) Stripe Press

(1:19:19) Katie’s parting wisdom

(1:23:17) Lightning round

—

Referenced:

• Beauty: https://www.amazon.com/Sagmeister-Walsh-Beauty-Stefan/dp/0714877271

• Terry (Olivia Colman) and Richie peel mushrooms—scene from The Bear: https://www.youtube.com/watch?v=f7D8THR_osU

• Building a culture of excellence | David Singleton (CTO of Stripe): https://www.lennyspodcast.com/building-a-culture-of-excellence-david-singleton-cto-of-stripe/

• Figma: https://www.figma.com/

• The Creative Act: A Way of Being: https://www.amazon.com/Creative-Act-Way-Being/dp/0593652886

• Quote by Robert Henri: https://www.goodreads.com/quotes/43397-the-object-isn-t-to-make-art-it-s-to-be-in

• Brian Chesky’s 11-star experience: https://www.product-frameworks.com/11-Star-Experience.html

• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034

• The Wright Brothers: https://www.amazon.com/Wright-Brothers-David-McCullough/dp/1476728755/

• The Boy, the Mole, the Fox and the Horse: https://www.amazon.com/Boy-Mole-Fox-Horse/dp/0062976583/

• Oppenheimer: https://www.oppenheimermovie.com/

• Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking/umc.cmc.apzybj6eqf6pzccd97kev7bs

• Toniebox: https://www.amazon.com/Toniebox-Starter-Lightning-McQueen-Playtime/dp/B09V7NJCD8

• Stripe Press: https://press.stripe.com/

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack

• Stripe’s job board: https://stripe.com/jobs/search

—

Books on design craft:

• Dieter Rams: Ten Principles for Good Design: https://www.amazon.com/Dieter-Rams-Principles-Good-Design/dp/3791387324

• The Vignelli Canon: https://www.amazon.com/Vignelli-Canon-Massimo/dp/3037782250

• Forget All the Rules About Graphic Design: Including the Ones in This Book, by Bob Gill: https://www.amazon.com/Forget-Rules-About-Graphic-Design/dp/0823018644

• Emotional Design: Why We Love (or Hate) Everyday Things: https://www.amazon.com/Emotional-Design-Love-Everyday-Things/dp/0465051367

• The Design of Everyday Things: Revised and Expanded Edition: https://www.amazon.com/Design-of-Everyday-Things-audiobook/dp/B07L5Y9HND

• Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/dp/0063046067

• In Praise of Shadows: https://www.amazon.com/Praise-Shadows-Junichiro-Tanizaki/dp/0918172020

• Interaction of Color: https://www.amazon.com/Interaction-Color-Anniversary-Josef-Albers/dp/0300179359

• Content Design: https://contentdesign.london/shop/content-design-by-sarah-winters-paperback

• Graphic Design Manual Principles and Practice: https://www.niggli.ch/en/produkt/graphic-design-manual/

• Collaborative Product Design: https://www.oreilly.com/library/view/collaborative-product-design/9781491975022/

• Principles of Form and Design: https://www.amazon.com/Principles-Form-Design-Wucius-Wong/dp/0471285528/ref=asc_df_0471285528

• The Timeless Way of Building: https://www.patternlanguage.com/bookstore/timeless-way-of-building.html

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe