Ryan Scott - The skills that get designers promoted

We're entering a world where roles and

responsibilities are kind of up for

grabs. So, how can we as designers think

strategically about our career?

>> Some of the tactical skills of design

that have been a moat for us for a long

time no longer are. They're not

differentiators.

>> How can we create the type of impact

that makes us irreplaceable? There are

skills that designers are getting hired

for right now which are like visual

design skills, high craft, but what

they're getting promoted for is

providing more value to the business,

being really high ROI.

>> What skills will be the most soughta in

the coming years?

>> If you want to be more strategic, if you

want to get promoted, if you want to

drive value for organization and be seen

as someone who is extremely valuable,

that's what I teach.

>> Welcome to Dive Club. My name is Rid and

this is where designers never stop

learning. This week's episode with Ryan

Scott is a deep dive into how designers

can think more strategically about their

career. He shares a ton of practical

lessons learned from his time at Door

Dash and Airbnb. And we go deep into how

you can make data a part of your

practice as a designer, different ways

to think about getting buyin for your

ideas and a lot more. But before we get

into all of that, I wanted to get Ryan's

MBA perspective on what the heck is

happening in today's job market.

>> So important for designers to have a

good understanding of not just what is

changing. We all feel that, but why it's

changing. Because if we don't understand

why, we can't really come up with a

strategy on how to get ahead. And that's

when we get exhausted, we burn out, or

we just kind of start chasing trends.

What happened during the pandemic is

that everything shut down. We have to

think about this as an economic

function. So businesses respond and they

change their strategy which is why

you're seeing adoption of AI, a lot of

layoffs and people hiring very

differently. And the job requirements

like the job market is so bizarre right

now in terms of companies wanting like a

very specific person with a very

specific background for every hire to

the point where they're probably like

filtering out really qualified people

because they have this really specific

need for something they have in mind.

So, we're seeing all these things and I

saw this quote on LinkedIn from a design

leader and said, "Honestly, no one knows

what's going on in the current market."

And I think that perfectly encapsulates

how designers are feeling right now,

which is like, "What the heck is going

on? We're seeing all these signals, but

we're having a difficult time

contextualizing them." And when we have

a difficult time contextualizing them,

then it makes it very difficult to have

a strategy on how to get ahead in that

environment. And then we burn out

because we're just trying so many

different things and everything is

changing so rapidly that we're just

pinging ponging back and forth between

well I think I need to learn AI and this

job wanted this specific thing so maybe

I should go do that and I hope I don't

get laid off and it's exhausting to be

honest. Real quick message and then we

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a y. Okay, now on to the episode.

there's so much demand like there the

job market is actually exploding but for

a like singular slice and then you go on

and then there's people who are talking

about how they haven't been able to get

an interview for like 8 months and it's

so weird to see the combination of that

like what's happening there you think

you know like I'm like let's just try to

make sense of it for a second

>> yeah I I just was having this

conversation u with a designer this

morning who's applying to jobs and the

way I kind of articulated is it's not

she was saying I think there's too much

competition. I don't think there's too

much competition. I don't think that

you're getting beat out by a bunch of

other people who are more qualified than

you are. I think what's happening to a

lot of designers is that the the bar

changed the standard. What companies are

doing is they've defined something so

narrow that they want. They're only

willing to hire that one person with

that one specific profile that that

standard has shifted. It's not a

competition problem. It's a do you meet

this specific puzzle piece problem that

most people actually don't. And the way

I describe it is a lot of companies are

just overfiltering right now where they

might say we want you to be in this

industry for exactly this many years. I

saw a design leader on LinkedIn say that

they got rejected for a job because they

had managed five direct reports and this

job required they had experience with

six. Like really finite level of detail

here which they're overfiltering, right?

They're going to lose out a ton of

candidates because they're so narrowly

focused. And so I think that's why you

see this specific persona of designer is

in high demand and everyone else is kind

of left trying to figure out what to do.

I think that comes down to the company

having a specific strategy in mind and

maybe not knowing how to execute that

strategy very effectively. And a lot of

it has to do with kind of macroeconomic

environment, how businesses respond and

then how hiring managers have to respond

to that.

>> Let's talk to the person who is feeling

the pain of this a little bit. Maybe

they aren't having as much success

getting interviews. They feel the fact

that they're being screened out

prematurely. How do you even think as a

designer right now about repositioning

yourself and the right knobs to turn,

what changes to make, what to experiment

with? Like do you have any thoughts on

how the individual designer can react to

the changes that some of these

macroeconomic pressures are bringing on?

>> The problem that I see for a lot of

designers is two things. One, they're

not selling the right thing anymore. And

then they're also not selling to the

right people anymore. Hang shoe just

posted on LinkedIn a couple days ago a

survey a poll and said who's most

responsible for driving these changing

hiring trends in design. And about 50%

of people responded that the design

leaders themselves, the hiring managers

themselves are responsible for these

changes. I think that's not the case.

The design managers often don't have

budget control. They're not the final

approver. They're the person that has to

take that candidate and then pitch that

candidate to someone else. And it's

typically a product leader and product

leaders care about completely different

things. I also saw someone mention that

they had been approved by the design

hiring manager and then the PM said nah

and they lost the opportunity. So I

think that designers are are still

thinking of I need to get this design

manager to hire me when really that

manager doesn't have the final say. And

so what we need to be thinking about is

instead of trying to pitch that designer

on why to hire us, we should be thinking

about how do we pitch ourselves to the

business? How do we talk about the

impact that we're going to have? Um,

hiring is one of the most expensive

investments that a company can make. And

we need to think about it that way. We

need to think about it as this is an

investment and they want to know if I'm

going to put $150 $200,000 or more

behind this person, what am I going to

get for that? And so that's the story we

really need to tell. Instead of I make

these pretty things or whatever argument

we're trying to make, look at the craft.

Look at the delight I'm creating. We

need to talk about hard numbers and you

know this is on shaping behavior. This

is how the money is going to come out,

how the metrics are going to move as a

result because the design manager cares

about those things but the PM the

product leader who probably has the

final say really cares about those

things. So we need to be selling the

right thing that impact and we need to

be thinking about who the ultimate

approver is and it might not be the

designer we think it is. Can we go a

little bit deeper there and talk about

some of the ways that the messaging

might change depending on who you're

speaking to? Like if I understand that

I'm trying to sell myself to the

business, what are some of the words or

phrases or positioning mechanics that I

would be using that maybe it would be

easy to miss if I was speaking just to

the design manager?

>> Yeah. So, when designers are speaking to

other designers, we kind of have like a

shorthand and it's okay for us to do

this. We think about, oh, I did XYZ

feature. I reduce cognitive load. I

change the friction in this flow. And

other designers understand that.

Typically product leaders or business

leaders, there's a bit of a gap. There's

a miscommunication. There's something

that gets lost in translation there.

We're not saying the impact that this

creates. And you see this in portfolios

all the time. People will typically

label their portfolio projects as, you

know, XYZ project for Y company. You

know, a redesign of booking for Airbnb.

It doesn't mention what actually came

out of that project, why it was worth

doing, how much money it created,

whether it moved metrics. You know, what

design work happened, but not what

business impact was created. And so, one

of the things I really talk to designers

about and train them on is to not just

say, I did XYZ work and hope and pray

that someone on the other end of that

conversation understands that that is

impactful. You have to really try to

bring it back into their world. use

their language and say this work drove

this metric in this direction. Be much

more specific because that's ultimately

what that person who's making that final

decision really cares about.

>> Okay. Then I'm going to be the voice of

the person who's listening who has

worked at a mid-tier agency for the last

3 years. And the nature of the work

means that they'll take on this complex

project in a various industry, but then

they're kind of handing it off and they

don't always get the nice dashboards and

cohort retention over the next 6 months

and they feel at a loss when it comes to

being able to wield data as a part of

their own personal story. Any thoughts

for that person?

>> Data and metrics are only one type of

business value and designers kind of get

put in this box. We kind of get trained

to think this way because we work so

closely with PMs and we often report up

to product teams. So we care about the

metrics and we should be thinking about

those things. They are really tangible.

People are gold on them. So their

careers and their career trajectory is

really dependent upon hitting those

metrics. So that's a really important

place to start. But not every project

has all the metrics you need to tell

that story. Not every project can be

measured with certain metrics. So it's

important to zoom out and think about

what other types of business value are

created. There were projects that I

worked on where we just repositioned

oursel against the competition. Maybe we

made our team internally more efficient

or increased the velocity or the

quality. We reduced uh the bugs that

were being created as a result of the

work that we were doing. Maybe just

changed the culture and we started to

work better as a team and have a greater

sense of ownership. Those are all things

that a CEO really cares about. And when

you go to business school, they train

you to think about everything as

holistically as possible. Business

school is not here's what metrics

matter. It's here's how to think about

the holistic health of the business. And

so the metrics have to be in the right

place. The culture has to be good. You

have to be hiring the right way. You

need to be positioned against the

competition. You need to be gaining

market share. You need to have good like

brand awareness with consumers and you

need to have a good kind of brand

reputation with consumers. All of those

things matter and every project might

have bits and pieces might be moving the

needle across the board for any of those

things. So maybe you don't have the

perfect metric and that's really common

if it's not being measured or the data

science team or the PMs won't give it to

you or you left the company years ago

and you just don't have access to it

anymore. Super common for that to be the

case. In that case look at did the

company launch it then it's probably

producing value for them. Even if I

don't have the numbers I can say look we

know this is producing value because

they launched it and it's been a couple

years and it's still driving value for

them. So we know it's directionally

doing the right thing. We think about,

you know, what was the purpose of the

project? Was it just to hit a metric or

was it for something else? So many

projects are about just neutralizing

some competitor's advantage. If that was

the purpose of the project or that was

something the project did, even if you

don't have the metric, you can say like

one of the projects I worked on was

launching food photography at Door Dash,

that absolutely moved product metrics,

but Door Dash was the only company that

didn't have food photography. everyone

else did. And so when Uber Eats launched

from day one, they had beautiful food

photography. We were kind of like, I

guess we should probably do this, too.

So yeah, did it move metrics?

Absolutely. And it moved metrics in a

really significant way. But that's not

the only way to tell that story. The

other way to say is like, look, Uber

Eats launched. We had to respond. They

have this thing. We're trying to sign

national deals with McDonald's and

McDonald's on, you know, we're on these

corporate calls with McDonald's.

McDonald's is saying, "Why don't you

guys have photos? We spend millions of

dollars on photography. Why can't you

help us? We have an answer for that. And

so, did it move metrics? Sure. Did it

also accomplish other things for the

business? Absolutely. And so, you tell

the best story you can with the evidence

you have at hand. And that should really

help mitigate if you don't have all the

perfect numbers. I love that reframing

because it definitely feels in a lot of

the dialogue that I see that it's

metrics check yes check no and you're

basically saying no we're just telling a

story that is going to be compelling to

somebody that is using a business lens

to evaluate me as an investment from

which statistical evidence is one way

that you can say something that is

compelling and and moves the needle. So

definitely makes a lot of sense. And

even for myself, I'm like kind of

reflecting back on some of my own

projects like, huh, how would I spin

that in a way where it doesn't feel like

just a label, but I'm I'm telling it in

as if I'm almost writing it to the

executive or the PM that would be

evaluating my case.

>> And what I see in interviews, and I've

done this before, I kind of my approach

for telling about the results of my work

is I call it shock and awe. I want to

talk about so many different things that

the project produced, so many different

types of value or impact that it really

kind of takes the pressure off all the

numbers being exactly right or all the

numbers being impressive in some way.

So, I'm going to mention metrics for

sure, but I'm also going to talk about

the way the team learns to operate

differently and more efficiently, how

that unlocked future strategic value, um

how it moved us competitively. I'm going

to mention every one of those things

almost on their own slide in an

interview and the impression after doing

that it's like yeah this project did

this and this and this and this in

addition to hitting some metrics too.

The impression is that's amazing like we

want that value here too. We want

retention and we want conversion and we

also want to work better and we want to

have more ownership and we want all

those things as a product leader or a

business leader. We want all of those

things. producing like the talking about

the results of our work in that way has

a huge impact in people understanding

our value as long as we're zooming out

and thinking holistically like a

business leader would.

>> Okay. So, we've been talking about this

idea of positioning and I want to

transition into a little bit more like

personal skill investment. I think a lot

of people are feeling the need

especially given the macro uncertainty

that we were kind of touching on

earlier. And I want to just read a line

that you brought up when we were talking

before we hit record where you said the

only designers in trouble are the ones

that are standing still. So where do we

move from here? Like a designer who

feels the reality of the moment. How

should we even think about future

proofing ourselves so that we can

continue to earn a living as a

professional UX designer in the years to

come?

>> Yeah, I really see there being two

paths. If you go to business school, you

might study strategy and game theory.

And I think those create a good roadmap

for us to move forward and think about

our design careers really strategically.

What is happening with AI is that it's

really rapidly collapsing all these

roles onto each other. So designers can

do more PM type work. We can vibe code

and do engineering work. All those

people can also do our work. They can go

into magic patterns and they can uh

create some mockups really quickly. So

we all have more overlap with each

other. We need to think about ourselves

as really valuable partners. And I want

to think about my relationship with PMs

and engineers as a true partnership, but

we're also competing for resources.

Which function is going to be invested

in? Who's going to get promoted? Who

gets more headcount? There's always a

little bit of tension there, and that's

really uh worth acknowledging. So I

don't want to say that, hey, we're

competing with these people because

we're partners, but we are in some ways.

If we study game theory, we're thinking

about different companies. How does one

company position itself in the

marketplace? And then how do we respond?

And it's about playing out all the steps

that are going to happen. So if we have

PMs and engineers moving towards design,

they're starting to use these AI tools.

Some of the tactical skills of design

that have been a moat for us for a long

time no longer are. They're not

differentiators. I don't need to have a

deep understanding of Photoshop

necessarily to get in there and make the

thing I want. So we can't claim that

anymore. So if they're moving towards

us, the answer is we need to move

towards them. You see this in businesses

all the time where Airbnb has home

sharing and Booking.com has hotels. And

then eventually Booking.com's like we

should have some home sharing and Airbnb

is like we should have some hotels. As

they start to compete, they start to

become more similar to each other to

kind of neutralize each other and get a

little bit of bites of each other's

market share. We're seeing the same

thing happen with designers and PMs and

engineers right now. So if PMs and

engineers are coming for a little bit of

our market share, we should do the same

thing and we should respond in the same

way. How designers are predominantly

thinking about that right now is things

like vibe coding, all these AI tools to

do more technical engineering work. And

I think that is really valuable. That is

one path that is us becoming more like

an engineer and knowing how to ship

things on our own. um knowing how to get

into the codebase and change the button

color, change the quarter radius, the

things that we had to like beg resources

for before. Now we're just empowered to

go in there and make it work. And I

think that's great for everyone, right?

The engineer did not become an engineer

so they could work with the designer to

make sure every tiny little pixel is

perfect. That's not necessarily what

excites them about their job, but it is

what excites us about our job. Now we

can go in there and we can make things

the way we want. That's really powerful.

The side that I see missing is designers

being equally or more excited about

being able to do the more strategic

work. So if PMS are moving towards

designers, we need to move towards

engineers. We also need to move towards

PMs and neutralize that a little bit. So

we need to start thinking about

ourselves as driving this business

impact and being equally responsible for

that.

>> Makes total sense to me. I think that

part of the reason a lot of the

discussion has been at least from my

vantage point quite technical is there's

almost a clarity when this other path is

buoied by specific tools and tactics and

workflows that you can learn. If I can

use this tool then I can create value

down this path. Whereas when you kind

of, you know, stand at the fork of the

road and look down the product path,

it's a little bit murkier and a little

bit more uncertain what it looks like to

actually grow in that direction. So

maybe we could talk a little bit about

how designers should even think about

charting that path down the product

lane.

>> Yeah, I think the first place to start

is that designers have a lot of these

skills already and I don't think we give

ourselves credit for that. Um there are

things like kind of our customer first

thinking, right? How business value is

created is by solving a problem for the

customer and then you see the metrics be

impacted. Sometimes companies will want

to start with business metrics first and

they'll say, "Well, if we start selling

customer data, we'll make a lot of

money." That typically doesn't end up

being very sustainable or create some

kind of conflict later on. Uh, one thing

I loved about working at Airbnb was that

we always knew that if we create

customer value first, then the business

metrics are going to take care of

themselves. That's how designers think

and that's a great way to think. So,

we've already got this like foot in the

right direction. We're also really

strong about systems thinking. So, we we

understand that sometimes some of the

tools that we have at our disposal like

AB testing are great in some instances

and not great in other instances. We

know that how would you AB test a design

system? Design systems, it's a system.

You can't pick it apart. It all works

together to create value. So designers

have a really good understanding of that

systems impact. And we also think really

holistically and a little bit further

ahead perhaps than our road maps. And I

think that's great. That's what seuite

executives do. If you're a seuite

executive, you have to have that

holistic perspective on the entire

business. And you have to be thinking

ahead about what comes next, what comes

beyond. I saw Andy Bud give a talk a few

months ago in Berlin and he mentioned

how uh designers are like chess players,

always thinking a few steps ahead. And

PMs and product teams are often like

poker players. They're wanting to just

maximize the number of hands they play

because statistically it works out in

their benefit. If you fold a bad hand

and you move on to the next hand, that's

how you're going to ultimately win. I

think that's a great metaphor for the

difference between designers and product

managers. But I also think that seauite

executives are chess players, not just

poker players. And so there's this

really nice relationship and similarity

between how designers think and actually

how seuite executives think. So I think

we have a lot of things going for us

already that if we acknowledge that the

whole idea of moving in that direction

becomes a little less intimidating.

Before we get into like the specific

skills that exist in these buckets that

you've kind of laid out, I'm sure

somebody's listening that's like, well,

I have a PM already, you know, and is

this complicating things if I start

moving in that direction? What is

effective collaboration even look like

in a world where people are kind of

infringing on each other's territory and

maybe the PM is spinning up lovable and

making a quick prototype. Yeah, I think

that is an ongoing negotiation and it's

going to depend a lot on who the person

is and what the company culture is like.

I was just speaking to a VP of design

who's been working in builder IO and

working with the engineers and the

engineers have helped set up builder IO

for the designers, but there was also

this conversation that needed to happen

about well who does what now? If we're

going to empower you to take things on

on your own, what does that mean? I

think that's a really valuable

conversation. And I think everyone can

win out of that. What do engineers want

not want to do that we do want to do?

Can we take over some of those things?

Maybe there's things that the PM doesn't

like doing that the designer really

cares about. And so you can start there.

You can also start with what do you need

to be successful? What metrics are you

trying to hit? What's going to get you

promoted? What's going to get you

recognized? What I do is try to say the

things that I can bring to the table are

going to help you as a product person in

these ways. I'm not trying to take your

scope. I'm not trying to reduce your

footprint or reduce your influence. I'm

trying to get us to all win together.

And if I can take something off your

plate that you don't want to do or I'm

really excited about or can handle, then

that's great. Uh if you need support in

some way, I have some skills to support

you in those ways as well. So, I think

those conversations are delicate, but

we're all having them. The same

conversation goes for designers. like

they can go in and vibe code something

or use magic patterns to spin up some

mocks. Okay, maybe we actually want

that. Maybe it's great for some of the

lower tactical types of things for other

teams to take them over and we are

advisers on those projects and say like

the engineers move forward with this.

That's totally fine. We check the box

and said looks great. Go ahead and ship

it and we can focus on larger more

strategic projects because other people

are empowered to do the little things

themselves. So, I think that that could

be true in all directions. And if we

approach the conversation that way, it's

important to acknowledge that people

across the spectrum are probably feeling

a little insecure right now.

Everything's changing and we're all

having to renegotiate everything. But

there is a future where we've all now

had the chance to reorient our roles in

a way that fits better for all of us.

So, I think that's a good place to

start. I've been designing products

every day for the last 15 years. But in

the last 6 months, everything has

changed. With AI in the mix, I'm

cranking out ideas faster than ever. But

none of that matters if I can't get the

feedback that I need to get the team

aligned. And right now, getting async

feedback still kind of sucks. So, I'm

building the product I've always wanted,

and it's called Inflight. I use it every

day to share ideas and get feedback from

the team. and it's totally changing the

way that I work. So, I'm excited to show

you. Right now, I'm only giving access

to DiveClub listeners. So, head to

dive.comclub/inflight

to claim your spot.

We're kind of figuring out where the new

lines are getting drawn, even leaning

into a new era of my relationship with

my technical co-founder right now. Like,

I got pretty comfortable jumping in and

doing a lot of the front-end polish.

And, you know, I get this text message,

"Wow, you know, that was so helpful.

Thank you." And then one day I'm like,

"Okay, I'll do a little bit more." And

I, you know, shifted PR and then got the

next test message and it was like, "Hey

man, never again." Like never again do

this. Like this is way over that line.

>> Yeah. We found the line. Everybody's

kind of got to find the line again.

>> Yeah. And and I think that it's good to

set expectations that it's going to be a

little bit of trial and error. And

again, it comes down to that person's

personal preference. It comes down to

the culture of the organization as a

whole and what the tolerance is for

this. But I see a lot of companies kind

of mandating the use of AI. And the

problem with those mandates is they're

not very specific. Doesn't say what tool

or how. And it also doesn't acknowledge

the fact that we're going to have to

change the way we all work with each

other and draw those lines. And there's

going to be some pain in that process. I

do think there are better things

>> beyond that process for all of us. It's

going to be worth that, but that doesn't

mean it's going to be easy getting there

right away. And so I would say be

experimental about this, right? Push and

try some things. see what feels right,

see where you get some push back, then

say, "Okay, that's where the line is."

That's fine. Let's agree that this is

how we'll operate, you know, in this new

world, and you'll take care of this, and

I'll take care of that. And maybe

project by project, it changes, but it's

worth having that conversation maybe a

little more literally, uh, really

stopping and taking a moment to say,

"Okay, how do we want to approach this

right now?" Because all of our past ways

of working are kind of being remixed at

the moment, and it's all back on the

table. So, it's worth being really

conscious of it, asking the question out

loud, having the conversation in a

really literal way, and then we'll find

kind of a new normal, all of us

together, but is going to take some

time. Okay. So, I want to get specific

about some of these more PME skills and

ways that designers can invest and can

pursue that path that we kind of laid

out earlier. And maybe we could start to

use your metaphor again of of playing

chess. I really like that. And I'd like

to know what the traits of great chess

playing designers even look like. Not

only to be able to see a little bit

further into the future, but given an

array of opportunities,

how do you know which ones are actually

worth pursuing and putting your name

behind? One of the best things designers

can do, and this typically falls to

product teams, but I don't think there's

any reason designers can't do this as

well, is to find new opportunities for

your business. That is something that I

have kind of specialized in and I've

always considered myself a hybrid

designer PM type person. I identify as a

designer but I realize that's not really

accurate. One of the things that I have

always enjoyed doing is going and

finding new opportunities for the

business. And I didn't understand in the

past why it's like no that's not your

lane. Don't find new value for us. There

are skills that designers are getting

hired for right now which are like

visual design skills, high craft, but

what they're getting promoted for is

providing more value to the business,

being really high ROI.

If you want to be part of the strategic

conversation, I think we need to be

comfortable being willing to start and

then drive that conversation. So, a good

example of finding new opportunities.

There's a lot of ways to do that. One

thing that designers do is we kind of

overindex on user research. That's our

primary tool. And engineers and PMs,

they want to AB test everything. And

we're both kind of stuck in these camps.

But there are so many other ways to

uncover new opportunities that are going

to also provide a lot of evidence that

something is worth doing. So you can do

some competitive analysis. You can uh

look at the market. You can see what

competitors are doing. And not just the

product, not just what the competitor is

building, not just the pixels or the

features or the scope, but also how are

they positioning themselves, how are

they pricing their products. Think

really holistically about what it is

you're seeing in the market and how

they're they're operating. I started

working at Door Dash when it was like 50

people and I reported to a co-founder.

There were four designers, eight

engineers, and no PMs at all. And so it

just fell on us to kind of figure out

what to do. One of the things I noticed

was that from a design perspective, from

an empathy perspective, when I was the

design lead on the Dasher product, I

really wanted Dashers to get paid

faster. Oftent times drivers have a

little less financial security. That's

why they're on a platform like Door

Dash. But we were only paying them once

a week. And so we would say, "Hey,

there's a rush right now. You need to

get off your couch and go do the lunch

rush. We'll pay you in 6 days." And it's

not a very compelling argument. you're

not going to drive a lot of behavior

like that. And so I realized like from

an empathy design perspective, what I

wanted to do is say, "Hey, these people

need this money. Let's do that for them.

Let's help them." That wasn't a very

compelling argument just by itself. So I

analyzed what competitors were doing and

realized that this once a week pay

structure was the least flexible system

on the market. Um, if you were driving

for Uber or Lyft, you could get paid

instantly. If you were driving for

Amazon, it was like rolling every 3 days

you'd get paid. We were making people

wait the longest. So, we were the least

effective from a competitive standpoint.

And then I just posted a survey onto a

Facebook group and said, "Would you use

this if we launched it?" And a bunch of

people raised their hand and said they

would. So, I started with user research

as there's maybe something here, but I

was also able to move beyond that and

say, "And there's competitive value

here. We're going to neutralize a lot of

the competitors. We're going to get

ahead. We're going to stay really

relevant. And there's customer demand."

All of those things really matter.

>> Okay. I'm going to paint a hypothetical

scenario here because what you're

describing is you kind of have the voice

of leadership in that world, but maybe

there's somebody listening who perhaps

they work at a larger company where

there's at least one level of separation

between the true decision makers and

maybe they actually haven't cemented

themselves as this opportunity spotter

and they're inspired by this episode.

They kind of want to try to do it for

the first time. They have something.

Maybe they've even went out and done the

research and they've put together what

the story, what the angle is. It's going

to be a very specific question, but how

do you then think about strategically

introducing that? At what levels, in

what format? That's a black box of its

own. So, could we speak to a person in

that situation for a second?

>> There are right ways and wrong ways to

do this, and I've done them both. Uh,

the ways that I found is the the wrong

way is to skip a bunch of levels. I've

literally just gone to like the CEO of a

company and said, "Here's my idea. I

think we should do this." And I got buy

in and that person said, "Yeah, go take

this to the teams." And then I took it

to teams and said, "CEO said we should

do this. We should do this." And ended

up pissing off a lot of people because I

didn't include them in that process. So

that would be the wrong way to approach

it. Even if you have great evidence, you

know, great evidence is about user

research, but it's also about all these

other things. And if you can bundle them

all together, you've got a really

compelling argument. But if you just

take it to the CEO and use that to

strongarm everyone, they're not going to

be very happy and you're going to lose

credibility as a designer. I have done

that. Do not make that mistake. A better

way to approach it is to more casually

introduce ideas. I think designers think

about our work in terms of either low

fidelity or high fidelity. And you're

seeing this strong push for jumping to

high fidelity right now as quickly as

possible because we can just prototype

everything so fast and it's so cheap and

easy to do that. Where PMs excel is in

no fidelity. It's just the idea. What do

you think about this? What do you think

about that? You have to be sensitive to

how you approach this conversation

depending on the culture of your

environment. If you're in a really

accepting, open, warm culture where

people want to collaborate, it's easy to

put yourself out there. If you're in a

really competitive environment where

people are like competing for resources

and butting heads a lot and holding

grudges, uh you have to be really

careful about how you propose your

ideas. What works really well in both

environments is to say, "Hey guys, what

do you think about XYZ thing?" And you

might not have everyone in the room

think that's the best idea, but what you

need are just a few people, these kind

of early adopters for our idea that

we're bringing to the market, bringing

to our company. And if we've got a

couple people who are like yes and type

people, who are how might we type

people, those are the people we want to

start with because they'll help us bring

this to fruition. They'll help us bring

it to life. they'll kick the tires a

little bit with us in a collaborative

sort of way. Not everyone's going to be

on board right away. They're going to

want to see some traction and see some

evidence. And that's okay. We can build

that progressively over time. So, what's

worked really well for me is to say,

"Hey, I'm seeing this opportunity.

Here's a bunch of evidence. I've got

user research. I've got some product

data. We've done past experiments that

say something along these lines as well.

I'm looking at the competitive landscape

and other companies are doing it. We

should probably pay attention to this."

Put that out in a meeting. see who

responds. Go develop relationships with

the people who are potentially

interested in that. Start with that

smaller and safer group and then bring

it to people and say, "Look, we've

kicked the tires on this. There's really

something here. Let us show you the

evidence and kind of bring that to

larger and larger and larger groups."

Um, that's worked really well for me as

a way to carefully bring my ideas to

market in a way that is inoffensive but

also really effective. Returning to our

kind of metaphorical PME path that we're

talking about, what are some of the

other skills that exist that you think

are kind of top of the list that

designers who are interested in growing

in this area could start to not only

adopt but actually grow the muscle and

think about ways that they can bring

more of this to the table in their org.

>> Two other areas I think are really

important are prioritization and

metrics. And those are two things that

uh can be challenging for users. We're

not trained in either of those things.

If you went to art school like I did or

you went to a boot camp, you're learning

about the tactical aspects of design,

but you're not trained on those types of

business thinking. The first thing I'll

say about prioritization is that I have

been so guilty of this. I will do some

user research and a user will say I want

this and I'll go to the team and say

user says they want this. We should do

this right away. The answer is almost

always no. And I for a long time felt

like PMs just existed to tell designers

no. And what I realized when I went to

business school was that there are so

many variables that go into making these

decisions, the the joke in business

school, especially the first year, was

that the correct answer to every

question is it depends. And that's what

they train you to do. They train you to

look at every possible variable and

think about, well, yeah, that might be

the right idea, but is now the right

time for that right idea? Maybe not. It

depends on a bunch of different

variables.

One thing that can feel unintuitive when

it comes to prioritization for designers

are some of these existing product

frameworks. So things like Rice, reach,

impact, confidence, and effort. And you

kind of use that to calculate what's the

value of a project. Now, I don't know

about you, but outside of work, I have

never used Rice as a prioritization

framework to make any other decision in

my life. It's something that's really

specific to the work, but then as soon

as you leave the office, you never think

about it again. A more intuitive way for

me to think about prioritization as a

designer is a relationship between

value, cost, and risk. And what's great

about this is humans evaluate value,

cost, and risk in every decision that we

make. From what car to buy, who to

marry, where to live, what to eat for

lunch, we're always thinking about uh is

this going to be worth it? and is there

any risk that I'm taking on by making

this decision of where to live or what

car to buy? You can actually evaluate

projects that same way. And it's useful

because when we talk about rice and we

think about impact, often that gets

boiled down to a single metric. Impact

equals conversion. Okay, that's what

we're gold on. That's what the, you

know, business needs from us right now.

But let's not joke ourselves that that's

the only form of business value that's

being created by this project. There are

so many other things that we need to

acknowledge that competitive

positioning, the strategic opportunities

that are unlocked by this project. Does

it impact our overall brand awareness or

overall brand reputation? Those are all

forms of value that we should consider

across every project if we're going to

compare apples to apples. The problem

with value is that it is so intangible

feeling. A lot of this is just

estimation. And so what's useful is if

you can come up with a bunch of

different ideas on the value that this

project creates, we can have a more

holistic conversation about it. The

thing about cost, if we're thinking

about value, cost, and risk being the

three things that drive all decision-m

cost is super tangible. Engineers will

just say, I think that will take 20

hours and you know exactly how much

money it's going to cost you. I think

engineering effort is one form of cost.

You also need to think about other forms

of cost in terms of like organizational

cost. Do we need to get legal involved?

Does marketing need to be involved? Um,

how complex is this? All of those things

factor into cost. Now, cost is tangible

and so it can dominate the conversation,

but there are really tactical things we

can do to mitigate cost in any project.

We can ship an MVP. We can ship just a

pilot. We can do a little bit less in

scope. There are levers we can

absolutely pull to make it acceptable.

If cost is dominating the conversation,

we should talk about reducing costs

where we can. and upplaying how much

value is created. The last thing

designers can think about is risk. And I

love this for designers because risk is

a really human psychological factor that

drives all of our decision-m. It's kind

of the fight or flight that occurs when

I do the mental math on anything that's

proposed. So, what do I think this is

going to do? How much do I think it's

going to cost? And am I exposing myself

in this project or is the business

exposing itself? Do we have the right

team in place? Is the morale good enough

to handle this project? Is the project

too complex? Do we have enough time?

Maybe there's some external risks like

are we going to trigger any type of

legal repercussions from this project?

And so risk is something that's worth

thinking about. And if you acknowledge

that those three things exist, you can

pull on those levers to push people

towards the direction you want. So you

can say we should do this project

because the value is really high and

there is some risk but we can mitigate

it this way and there are some costs and

we can mitigate it in that way. You can

also use it in the opposite direction.

You can say if we don't do this, we're

leaving a lot of value off the table.

We're potentially increasing a lot of

risks by letting this debt just compile

forever. Then risks are increasing. At

Airbnb, I use this really effectively

once. The last large redesign that I let

was of the entire host calendar. And

this is how all hosts on Airbnb open all

their nights and set all their prices,

which if you think about it is the

foundation for all of Airbnb supply and

all of its revenue. So huge, huge

pressure.

>> The fundamental unit economics are at

stake.

>> Don't mess it up. uh another like high

uh risk project that I led at Airbnb and

literally I was talking to the CTO of

homes and presented a few different

options and one of the options was if we

go down this route like Brian's probably

want to get really involved and have a

lot of opinions on this direction

because it's really different and really

kind of shocking and so we decided maybe

we didn't want to open that can of worms

that wasn't the thing we wanted to do

because it would increase cost of the

project it would increase risk of the

project and we're going to do something

a little more in this direction so you

can use value and cost and risk as a way

to move people towards an idea or

emphasize what's being left if we don't

pursue an idea. But it is far more

intuitive for designers because that's

how all humans make all decisions

anyway. It's not a really type framework

you have to memorize. You can think

about it at a human level and designers

really excel when we think about things

on human levels. I like the Brian

example a lot because I actually do

think some of these calculations are

becoming a little bit murky because in

past years for me the dominant anchor of

these discussions is engineering effort

which is something that you were

alluding to. It's so easy to understand

the cost of something as a function of

time. But now we're entering this world

where it's like goodness you can make

really significant changes to the

software element of a product in days

not weeks or months. That changes the

discussion a little bit. You know, you

can you almost sit from this vantage

point of we can do anything. You know,

in three months we can do anything. So

now how do we think about sequencing and

the right levers to pull and risk kind

of changes you know I spend my time

thinking more about the potential for

bloat and complexity than gosh we only

have this many manh hours to allocate.

What is the best way to use them? You

know it's really kind of changing even

in the last six months. I've started to

feel it.

>> Absolutely. I created this framework as

a way to understand the complexity of

the interactions between all of these

different levers. Right? If you reduce

cost and you say we can ship so much

more so much faster, you may or may not

be producing value. You might just be

shipping a lot of stuff. And so

>> you might be going backwards.

>> You might be going backwards. You might

need to think about value more

holistically and say, "Cool, we can do

anything. Should we do everything?"

Probably not. So, we should think about

how does the value lever change and our

perspective on value if cost is

dramatically reduced. Like everything at

the grocery store is super cheap, does

that mean you should buy and eat it all?

Probably not. Some of those things

aren't as healthy for you. I think

there's also that kind of risk lever. If

cost goes down and you can do

everything, does that increase the risk

of now everyone's just doing everything

all the time and there's not we've lost

some organization or we've lost some

stringency in how we decide what to do.

And so it can be beneficial, but you

have to balance all of these things

against each other. And so I think it

that framework creates a really nice

visualization of yeah, cost might have

gone down, but maybe that

correspondingly increases risk. One

thing you'll see is sometimes a really

great other way of looking at this is

you have to invest a sufficient amount

to get value. And this is where

designers really struggle with MVPs is

if you don't actually meet a need or

solve a problem for someone because

you're underinvesting in the solution,

then you didn't check the box for them

and no value is created. So you can't

just reduce cost to nothing and think

you'll still get value. There's a

there's a line where cost has been

reduced too much. It's too sub MVP and

then value just plummets as a result.

And so I think sometimes teams think

about like oh we get all this value and

if we just reduce cost then all that

value is preserved not always the case

and so it's worth thinking about those

three levers and they do influence each

other. If cost goes down maybe that

impacts value maybe that impacts risk.

>> So the other thing that you mentioned

outside of the sequencing piece was more

of the data analytics getting into the

numbers and I know that comes more

naturally for you. A lot of designers

frankly don't spend any time in Postto

or Metabase or wherever this is living.

Maybe they have access but it's not part

of their practice. So I kind of want to

take this in two pieces if that's cool.

Maybe first we could talk about easier

onramps for someone who is not

considering this a regular part of their

practice. They're completely rellyant on

the PM for access to data even. How do

you get started? and then maybe we can

jump into some slightly more advanced

use cases from there.

>> The right place for designers to start

if they want to get involved in metrics

is actually not just opening a tool and

trying to find a dashboard and jumping

right in. A couple things have to happen

first if you're going to get there

eventually. That's like step number

three. The first step is if the product

team or executives or data science has

these numbers, are they willing to share

them with you or not? Sometimes you just

need to ask and they will provide

access. And if you're in that type of

environment and people are

collaborative, they might help, you

know, coach you on it, walk you through,

explain it to you, they might not want

to share those things with you. In which

case, this isn't a tooling problem. It's

a relationship problem. And so, we need

to get to that point of why does that

person not feel like they want to share

this with me? Is it because they don't

think designers should have an opinion

on that? Maybe. oftentimes it's because

they don't want designers kind of taking

control or having more power, having

more influence and being empowered in

that way. So that's where starting with

that relationship and if someone's

pushing back, start to understand what

might their incentives be, maybe they

feel a little insecure about their

position at the company, maybe if

designers start talking about metric,

they feel like they're losing some

control. If we start to understand where

they're really coming from, then we can

work on our relationship where we are

seen as someone who's going to help them

with their goals, not take away from

their goals. We're not going to go rogue

and start advocating for all these

things and they're going to lose control

of the narrative or they're going to

lose control of the road map in some

way. We're here to compliment them and

support them and find opportunities and

bring those opportunities to them. If

someone's feeling really insecure, I'm

just going to try to make them feel as

safe as possible so they don't get

defensive and kind of block me out. So

that's the first thing that is the most

important is the foundation of that

relationship. The next thing that has to

happen if you're going to like go into a

dashboard and figure out what's going

on. You have to have some good

foundation in those key metrics. I over

the last year have run data science

workshops like 4 hours with designers

and one of the first things we do is

just brainstorm what metrics do you know

and you'd be surprised like sometimes

groups of people know quite a few

sometimes they struggle. So knowing

having some familiarity with kind of the

metrics and especially the metrics that

matter to your business and matter to

your team. So you should be aware of

conversion and retention and customer

acquisition costs and annually recurring

revenue and all of these basics but your

team might not be gold on all of those

things or that might not be the OKR for

the quarter. So start with what is the

highest priority right now? What is the

success metric on this project or a few?

We should probably be measuring multiple

metrics for every project and want to

understand

what's being created, what's being

moved. Rarely does one project move just

a single metric. So let's be part of

that conversation. And if you're not,

the first place you can start is just by

asking, hey, I want to do a good job as

a designer PM, can you tell me what

we're trying to hit here so I can shape

the design in a way that's going to help

the team be successful? So having that

familiarity and developing that

relationship are really important. And

honestly, the best thing you can do to

check the box on both of those things is

just start talking to those stakeholders

and showing curiosity. Not coming out

strong with an opinion, not saying, "I'm

a designer. I deserve access to this or

I need access to be able to convince you

otherwise." Like, say, "Hey, I care

about us all winning. I care about being

successful. I care about this product

being impactful. I care about us all

getting credit and promoted for those

things. I'm sure you do, too. help me

understand what we're trying to do here

so that I can help us do that. Um,

that's a good way to develop that

relationship. It's a good way to then

leverage their expertise and have you

learn some of those things and then you

can get access to the tool. But those

two things have to come first.

>> If level three is getting into the tool,

what do some of those more advanced

levels even look like? for people who

understand the importance of writing out

the list of the key metrics that matter

most and keeping tabs on them, but maybe

want to go a little bit further that,

you know, even spotting patterns that

are slightly not obvious or being able

to make connections that would spark new

ideas that otherwise wouldn't surface in

a road map discussion. What is that look

like in practice for you?

>> Yeah, I've got a few good examples of

that. One of the first things you can do

is just look for weird outliers. And

when it comes to data, the thing that

really matters about all data is it's

about human behavior changes. Everything

we're measuring is someone's doing

something differently. So when you see

an outlier that's really bizarre, it

might signal this human behavior or

human attitude. That's where metrics and

data becomes really accessible for

designers. If we don't think about it as

a math function, but we think about it

as a reflection of what humans are doing

differently, I'm comfortable with human

behavior. That's what I'm here to shape

is human behavior in our product. So

looking at outliers is a really good way

to uh get started. Anything just like

seem really unusual or out of place.

Designers might look at the data, the

same data as a PM or a data scientist,

but have a different perspective because

they're looking at it from that human

angle. A really good example is when I

was at Door Dash very early on, eight

engineers, no PMs, I just asked for

access to Amplitude just to look at what

was going on in the website. And the

first thing I noticed was you have this

like perfect funnel. You got a lot of

views on the homepage and then fewer

views on the restaurant and then even

fewer in the cart. But after the cart

once someone checked out the page that

showed people the status of their order

had three times more page views than the

homepage. So people were there just

clicking clicking refresh refresh

refresh. And what was happening was

they're getting angry. They're getting

upset. They're getting nervous about

where where's my order? Where's my

order? Where's my order? So I noticed

this really strange behavior. This does

not look like a funnel. This looks like

a funnel and then kaboom huge number of

page views. So I thought maybe people

are angry, hangry, getting frustrated,

getting nervous. Refresh, refresh,

refresh. We might want to just surface

this information to them in a more

dynamic sort of way before they start

contacting us. Every support call is

like $8. If we can mitigate traffic away

from that, it would be huge for the

small business we are. And so I was the

person who at Door Dash proposed live

order tracking. I said, "You should be

able to go to the website and it should

just update its status for you in real

time and you shouldn't have to refresh.

You should always feel confident you've

got the most up-to-date information."

And we launched a super minimal textonly

MVP of that. But that was the foundation

of live order tracking. And now you go

to Door Dash and you can see exactly

where your driver is on a map. All of

that is about preventing that hanger,

preventing that anxiety. And that just

came from looking at a dashboard and

seeing something that seemed out of

place and coming up with a hypothesis

about it.

>> I love it because it's the perfect

example of wrapping the data in that

human story that's coming from the user

empathy that design is uniquely

qualified to bring to the table.

>> Absolutely. Another thing designers can

do or kind of look for patterns even in

past experiments. As a designer, it was

difficult for me to sometimes advocate

for resources for new experiments. the

road map is already set and they'd say

well we need evidence to go expend these

resources. I'd say great can I have some

you know resources to go get the

evidence and they say no and you get

stuck in this catch22.

>> One thing you can do is go look at like

maybe past experiments and reinterpret

the data with your uh designer lens. So,

at Airbnb, we had a system called ERF,

and it was all the experiment data from

the past, and I just kind of had access

to it. I'd look around at all of the

different experiments we had done. And

there was one experiment in particular

was really interesting, which was we

were not showing guests the final price

until they went through the entire

booking flow. This was years ago. And

so, you had to like go all the way

through. I want to book this home. I

want to introduce myself to the host. I

want to make a bunch of decisions. Step,

step, step. And then you get to this

final page and that's where we took the

time to calculate this is the taxes,

these are the fees, here's the total

price. And so the team realized like

that's not a great experience. You don't

want to make people jump through a bunch

of hoops to get to the end and realize

that oh I can't afford this place. All

the fees make it too expensive. You want

to surface that information as early as

possible. So the team launched an

experiment and they put a little modal

that calculated everything. And what was

great is that you could go right from

the listing to that modal and it would

show you how much it cost and you could

decide whether to move forward from that

point or not. Page views through the

whole flow went way down because people

didn't have to go through it anymore and

conversion went way up and the team was

like great successful this is a win. I

looked at that and I thought this is

great but it signals something so much

larger. It's that people really value

when this information is at their

fingertips. And it occurred to me, why

are we making people go through this

flow at all then? Why can't all of this

information just be a single page? And

so that was kind of the insight of

looking at past experiments and kind of

recontextualizing it. I'm like, this

shows us what works. Why don't we really

commit to this direction? And so I was

the person at Airbnb who proposed, why

do we have a five-step checkout flow?

Let's have a single page with a single

button that people can just tap. All the

information is there and the action is

now there as well and that really

dramatically improved conversion for

Airbnb right before the IPO.

>> One of my favorite parts of interviewing

you is you have this unique combination

of past experience and very clear

stories that you can learn from by

listening, but then also you're just an

educator at heart, you know, like it's

just clear listening to you talk that

you thoroughly enjoy teaching. And I

want to give people an opportunity if

they're interested in going deeper. you

have, you know, bestselling courses on

all of Maven for uh, you know, it's an

important time basically for designers

who want to grow in these areas. So, can

you just take a minute to give people an

idea of what do you teach, who's it for,

and what can people expect to get out of

it?

>> What I teach are business skills for

designers and it is that piece of the

pie. It's like yes, if engineers and

product managers are moving towards us,

we have to move towards both of them.

There are a million vibe coding courses

and and learning how to do the technical

side of engineering and that is awesome.

I teach the other half of the coin. The

if you want to be more strategic, if you

want to get promoted, if you want to

drive value for organization and be seen

as someone who is extremely valuable,

that's what I teach. So, uh I bring

everything from all of my experience

working at all these companies and being

a designer for 20 years and everything

I've learned succeeding and failing a

lot at some of these companies on these

big projects. I like to bring designers

behind the scenes on a lot of these

projects, but I also complement that

with everything I've learned in my MBA

about how businesses work, how people

think about, you know, making decisions

in a business and how designers can get

involved in that process. And so, uh,

I've got a few courses. The most popular

one this year has been my PM master

class for designers and is teaching

designers how to find opportunities,

assess them and pitch them using data

and some really strong stakeholder

analysis and negotiation skills to bring

ideas to the table and actually see them

through to launch. And that is not only

really good for users, it's good for the

business when designers participate and

drive that process. And it's really good

for our careers and really good for our

portfolios.

>> Hey, real quick. if you're listening to

this and you want to learn directly from

Ryan. I asked him if he'd be up for

giving a discount code for the dive club

community and he said yes. So if you go

to dive.comclub/yan

you can get a special offer on his PM

masterclass course. Okay, back to the

episode. Yeah, one of my favorite lines

from this talk is the visual skills get

you hired but it's this more product

strategy business skills that get you

promoted resonates completely. I never

thought about it quite that way, but

you're right. This is the way that you

if you really want to advance your

career ultimately, you're employed to

drive value for an employer and thinking

very strategically about how to make

that work is the way.

>> Yeah, you are an investment that they

are making and they want to understand

what they're getting for that investment

and that is not wrong. That makes a lot

of sense, especially when the

macroeconomic environment is so bizarre.

It has been so disrupted over the last

few years. We all are spending money

differently, care more about what we're

getting for our money. Businesses are

the same. So, they just want to have a

clear picture of what's going on. And

the more value we can produce and the

more clear we can be about that value,

the more we're going to be rewarded and

the less likely we are to be laid off,

it works really better for everyone.

>> Well, I I feel very confident in the ROI

of people listening to this discussion.

It's always dense, action-packed when we

talk to you. So Ryan, thank you so much

for coming on today and dropping the

knowledge bombs. It's always fun.

>> Thank you for having me again. I really

appreciate it. It's been a great time.

Before I let you go, I want to take just

one minute to run you through my

favorite products because I'm constantly

asked what's in my stack. Framer is how

I build websites. Genway is how I do

research. Granola is how I take notes

during crit. Jitter is how I animate my

designs. Lovable is how I build my ideas

in code. Mobin is how I find design

inspiration. Paper is how I design like

a creative. And Raycast is my shortcut

every step of the way. Now, I've hand

selected these companies so that I can

do these episodes full-time. So, by far

the number one way to support the show

is to check them out. You can find the

full list at dive.club/partners.