How to Influence Through Communication, With Alastair Simpson (VP of Design at Dropbox)

Alastair Simpson is a design leader and mentor, serving as VP of Design at Dropbox. Prior to Dropbox, Alastair was Head of Design at Atlassian, where he helped scale the design team from 20 to over 250. On today's show we chat about craft and how important it is for designers at any level, persuasion, how to present work, and how to deal with puzzling feedback.

Timestamps:

• 00:00 – Intro
• 02:28 – Alastair's journey into Design
• 06:34 – On building the right habits
• 11:24 – Sharing work, getting feedback, and storytelling
• 27:45 – How to get good at presenting work
• 31:44 – Soft skills that are important for designers
• 33:56 – Craft of Design vs. surgical optimisation
• 41:29 – Leading through craft
• 47:16 – The importance of inspiring others
• 50:06 – What Alastair hopes will happen over the next decade
• 52:02 – End of show questions

Connect with Alastair

LinkedIn, Medium

Selected links from the episode

The one critical skill most designers overlook, by Alastair
Influence: The Psychology of Persuasion, by Robert Cialdini
Start With Why, by Simon Sinek
Atomic Habits, by James Clear

Creators & Guests

Host

Christian Vasile

🎙️ Host & Growth Product Designer

What is Design Meets Business?

Design Meets Business is a podcast that inspires designers to think beyond pixels. On this show you'll hear design leaders from all over the world talk about their stories, lessons they've learned during their careers, and how you can use Design to make a bigger impact in your organisation.

Alastair: If you actually present
your work in a really structured

way, and you actually do a really
good job of presenting that, then

what you'll actually find, to your
point about puzzling feedback,

you'll start to get better feedback.

Because, again like, whilst it's
important just to show your work, and

it's good just to riff with people, and
just to go back and forth, how you frame

things can change the conversation.

Mhm.

Christian: The discipline of design
is now key to building great products.

More and more companies are making
space for it at the higher levels.

More people than ever
want to become designers.

And most of us who already do the
job wants to find ways to have just a

little bit more impact in our teams.

Welcome to design meets business.

I'm Christian Vasile and on this
podcast, I bring you world class

product and design leaders who found
ways to shape products, companies,

and entire industries, and who are now
sharing what they know with you and me.

My hope is that we all get to learn
from the experiences, ideas, and

stories shared on this podcast and, in
the process, become better designers.

If you've ever wondered whether
design executives still care

about craft wonder no more.

Today I talked to Alistair Simpson,
Vice President of Design at Dropbox.

Alastair and I talk a lot about
craft and how important it is

for designers at any level.

We talk about the art of the pitch,
about how to present work, how

to deal with puzzling feedback.

This episode is full not only with
tactical advice you can take and apply

today, but also with a lot of inspiration.

Talking to Alistair really feels
like you're talking to a designer

who at his core truly and deeply
cares about the work he does.

This is one of my favorite
episodes on the show, and there's

no need to delay it any further.

Alistair Simpson, everyone.

Alistair, it's a pleasure to have you on.

I first heard about you around 2015 when
you were leading design at Atlassian.

And back then in my wildest
dreams, I didn't think one

day you'll be on the podcast.

So, I mean, There was no podcast
back then, on my future podcast.

So yet here we are very excited
for today's conversation.

For people who don't know
who you are, let's give them.

a little introduction of your
background so they can understand

where you're coming from and how
you got to where you are today.

Alastair: Sure.

And thank you for having me on Christian.

It's the pleasure is all mine.

And hello everyone.

My name is Alistair Simpson.

I'm English.

I live in California and kind
of France a little bit but I

spent 12 years in Australia.

So that's the kind of weird mix
of accent that you can hear.

I'm a father of two, before I'm anything
to do with design and business, I'm a

father of two young kids, Frankie, my
daughter, who's nine, and Buddy, who's six

and they keep me entertained all day long.

And I also interesting fun
fact that might come up.

I played professional soccer until I
was 16 in England, and then I played

semi professional soccer until I was 37.

And I always like to say
that I retired at 37.

I had to give up because I got
too many injuries, it's nice.

It sounds nice.

You say you retired on the design side.

I started as a design team of one.

I did everything in a small well, a large
publishing company, but a small digital

division of this publishing company.

I did everything.

I built my own usability testing
laboratory using software called

Moray, for anyone who's as old
as me who can remember that.

I did branding, visual
design, interaction design.

And then I scaled a small team.

I then have traveled
around the world a lot.

I spent a couple of years traveling
around the world in South and Central

America, and then came back, worked in an
agency, did cool technology, things like

in flight entertainment gaming console,
app design, lots of different fun things.

And then, as you mentioned,
Christian, I went to Atlassian,

where I spent six years there.

Help scale the design team from, I
was designer number 20 and helped

scale the design team to over 300.

Uh, I worked on all the tools that
Atlassian have, Jira Confluence,

Trello, Bitbucket, SourceTree.

And then after six wonderful years,
I left and I'm now at Dropbox, which

is where I am now in California.

I run design, brand, research,
content design at Dropbox.

And also, interestingly, I ran our
shift to remote work for two years

because we saw that as a design problem.

And I've been here almost
four years in California.

And it's, as I said, a pleasure
to be on your show, Christian.

Thanks for having me.

Christian: Yeah.

Thanks for being here.

I uh, well, look, first of all, we
can't go into talking about design

without talking a little bit about
your football career, because I

actually did not know about that.

How did you how did you turn
a designer from a footballer?

Is it because football didn't
work out or what happened there?

Alastair: Oh, totally.

No, no, totally.

Football was my dream.

Up until the age of 16, I was
at a professional club called

AFC Bournemouth who are now in
the Premier League in England.

So up until 16, I was there.

But at 16 in England, you get
your first professional contract.

I didn't get a contract but I
then went and played in the kind

of minor leagues in England.

So if you've been following Welcome to
Wrexham on Apple TV, it's the league

just below where Wrexham started.

That's where I played.

So I was playing semi
professional in England.

And then I continued when I moved
to Australia, when I was 25, I

continued playing in Australia for
An amateur club to start with, but we

then went semi professional into the
kind of state leagues in Australia.

That was my first passion was
football and, linking a little

bit to design and leadership.

I mean, I learned a lot.

From elite sports that I applied
to just my career day to day.

When people often ask me, what's it
like to like train at a professional

club or a semi professional club?

And honestly, the answer is it's
monotonous and boring because all

you're doing is practicing the
same drills over and over again.

Because you're trying to give yourself
muscle memory so that when the

game comes, you can actually like
focus on the moments in the game.

So the skills are just
there, they're innate in you.

And so training is all about habit
formation, doing the simple things

over and over again, and then in
design, like honestly, in leadership,

that is a lot of what the job is.

It's doing the simple things.

It's turning up to design
critique twice a week.

It's showing your work.

Early and often it's doing the simple
things over and over again, like speaking

to customers, understanding their
problem, partnering with stakeholders.

It's a lot of simple things
and habits that actually then

create great experiences.

And so I honestly took a lot.

For my football career that I applied to
kind of design and leadership and habit

formation is probably the biggest one.

Christian: I really like what you
said there that even being a designer

it's, it's a lot about, I mean, you
said being, you know, doing design

leadership or being a design leader, but
obviously for just being an individual

contributor is roughly the same.

Yeah.

Most of the time, at the end
of the day, if someone asks

you, What have you done today?

Probably the same as yesterday,
probably the same as the day before.

And I think that there's a bit of
a lost art and probably not art.

I don't know what the right word
is, but this idea of patience

and on working on something for a
long time until you actually get

good and design education today.

Maybe we'll get to touch upon
this a bit later, but I just

wanted to draw a parallel.

Tells you that just do this bootcamp and
when it was three months, six months,

and then you're a designer and yeah,
you are a designer, but that doesn't

necessarily mean you are a good designer.

You're at the beginning.

And I think the expectations need
to be adjusted a little bit there.

And the reason people.

are good at design is because they've
done the same things time and time again,

they've built those habits, and perhaps
not a habit, but perhaps a gut sense

for you look at two designs and you
think, I think this one works better and

I can't tell you why, but it's probably
because you've done that so many times.

So I just wanted to draw that
parallel really interesting.

Something that I believe in is that
to be good at something, you need

to do the same thing over and over
for a very long period of time.

Alastair: It's true.

It's incredibly true.

And the people that I think talk
about, or the person I think talks

about this a lot is James Clear,
like his book, Atomic Habits.

And, when a lot of people, they'll, for
example, they'll train for something,

like they'll try and run a marathon,
because that makes quite a good story.

But actually, if you want to
get really good at exercise and,

managing your weight, then you
should just exercise every day.

For two years, like not just for the
kind of leading up to the marathon

and then ending like you don't run the
marathon and then stop, it's like just

being consistent over and over again.

And then I think something you touched
on, which I believe in design is if

you keep doing the same things over and
over again, you will learn, you'll make

mistakes, you'll build your own intuition.

And as a designer, you're also building
your taste, because I think this is

something that we've lost in designers
is having an opinion and having great

taste about what great looks like.

And again, if you've done it over and
over again and seen it many times.

Then you're building that
muscle and I think that, it's

people lose the sight of that.

They think that there's something
you can just get very quickly, where

actually it takes a lot of time and
a lot of repetition and just habits.

And but people don't necessarily like that
because it doesn't make for a good story.

They're like can I just, take the pill
and actually automatically be faster?

And it's no, it's.

Just it takes a lot.

Christian: If you'd have to look at
the life of an individual contributor,

I think these are the three most
important aspects of your career that

you can build these habits around.

What would those be?

What would you ask someone who's
pretty new to the job focus on is the

three main things to try to do on a
daily basis to build those habits?

Alastair: The important things
for me are know your customer.

Okay.

So what is the customer problem?

Also know your internal customer.

So what is the business problem,
but know your customer really well.

So however you'd get close to
it, there's dozens of methods

to get close to customers.

Many of the people miss are
things like shadowing sales calls.

Shadowing customer support calls like
we always think about knowing your

customer is like doing some fancy piece
of research where actually it's like

just go listen to some support calls.

See what the customers are
saying about your product.

Go listen to some sales calls.

See how customers are
reacting when they're looking.

Keep it being given a
demo to your product.

So I think knowing your customer and
knowing the internal customer as well,

your partners and your stakeholders, I
think then just doing the work if you

know the customer and the problem then
what are ideas and solutions that you can

actually solve that problem with so there
are dozens of ways that you can solve a

problem but we too often get to like oh
this is the way and it's is it like but

how have you actually like thought about
this and then the third one other than

just doing the work on your own is then.

Sharing your work and
showing your work, right?

I'm a big believer in iteration and
showing work early and often, which again,

I think we've lost in design where we try
and hold on to things for too long, where

I believe that designers should be showing
work every 48 to 72 hours, because if

you then get a piece of feedback, you'll
think differently about your solution and

you can modify it and you can build on
that idea and actually make it better.

So I think if you're really pinning
me down on three things, it would be

the three things like knowing your
customer generating solutions, like

coming up with lots of ideas, and
then also just showing your work to

peers and partners, customers, other
designers, and getting feedback and

being brave enough to get that feedback.

Because again, that's something I
think that we've lost is like, You

know, it's, it's vulnerable when
you're sharing your work, you're

putting a piece of your soul up for
people to like give you feedback on.

And that can be hard, but I
think that's the only way to

make really great products.

So there are two

Christian: threads that
I want to pull on here.

This one around feedback and sharing work,
there are specific questions I have there,

but first of all, I wanted to mention
that a few years ago as I was working

for a larger company, I got to sit on a
few calls in our customer support center.

And I swear that I have learned on those
two hours more than I have learned in,

weeks of just doing other work and it's so
understated how or under under appreciated

just how good of a technique it is.

Technique.

I don't know if technique
is the right word, but yeah.

Let's talk a bit about sharing
work because as you said, it's a

very vulnerable position to be in.

You've done all this work.

Sometimes you've easily fall in love with
some of your work and then you present it

and people just perhaps sometimes like it.

Perhaps they trash it.

Perhaps like one of my colleagues
says, I don't hate it, which is a

very neutral way of saying it's okay.

How do you deal as an individual
contributor with feedback?

And then how do you deal with
puzzling feedback, meaning feedback

you don't necessarily agree with.

Alastair: I'll pull out a
few thirds of my own there.

From my, I mentioned that I traveled
around the world, and when I was traveling

I took a job in a, I had to earn a
little bit of money when I was traveling,

and I took a job in a call center.

And I always say that My design career
started in a call center because if

you've never worked in a call center,
you can't see people like you do on zoom.

Nowadays, you literally have a screen
in front of you that just says the

person's name that's calling in or that
you're calling to their account number.

And that's it.

Three seconds later, they're
on the phone with you.

And sometimes they're angry.

Sometimes they're happy, but you have to
like Communicate really effectively with

these people and part of communication
is actively listening and asking really

good questions and ask going, you know,
the five why's is very like common.

It's like trying to get to the problem
beneath the problem because quite often

when you're in that call center situation,
somebody's angry about something, but

the problem is actually not that thing.

That's the surface issue.

The actual problem is deeper down and you
have to communicate effectively with them.

Okay.

Make them feel safe, make them feel
heard, ask good questions to uncover

the true need, which is actually
what we're doing in design, right?

A great designer is uncovering the
real need from a customer or from

the business and then designing
a solution that meets that.

And so that's the first thing that I
think many designers miss is, okay,

if I'm sharing my work, how am I
communicating that work effectively?

And in that call center situation,
I also got training on a good sales

technique around how you set up the
work, make sure people understand the

problem, make sure they understand
the true need, press on that.

And then present your solution
in a way that clearly

solves for the customer need.

And I think if you actually present
your work in a really structured

way, and you actually do a really
good job of presenting that, then you

will, what you'll actually find to
your point about puzzling feedback,

you'll start to get better feedback.

Because again, like whilst it's important
just to show your work and it's good

just to riff with people or just to go
back and forth, how you frame things.

Can change the conversation and so as a
designer I think it's very important and

this is something I learned from the call
center is you've got to frame your your

pitch your solution so that it's very easy
to either get great feedback or get people

to agree that this is the right solution
because I've done the work I've already

understood the problem this is the best
solution based on these three things and

the goals that we've got as a company.

Therefore, this is why we
should be forward with this.

So I think your framing of when you're
presenting work is very important.

And I think, there's
a bunch of techniques.

We can probably put it in the show
notes that come from sales and sales

often gets a kind of a bit of a bad
rap, but they have some good frameworks

around how you set up your work to.

Or how you, you set up work to
present it in the right light so that

you again, get the right outcome.

Either somebody wants to go ahead with
it or somebody wants to question it

and ask you really great questions.

Now, your question about, what
do you do with puzzling feedback?

Again, I would lean on the techniques
I've just outlined, which is to listen

intently, listen like you want to learn.

That's a really good framework,
like actually listen like you want

to learn, because most people when
you're presenting work, you're

not really listening to learn.

You're like, You can be defensive you're
like they just don't like the solution

but you actually need to really listen
and then you can mimic back to them what

you think you heard but then ask for more
clarity a really simple way to try to

better understand feedback if you don't
really understand what it is is I love

that piece of feedback Christian but could
you just say a little bit more about it.

Because you're then inviting that
person, you're saying, Hey, this was

interesting, but say a little bit more.

Another technique, a very simple
technique is help me understand that

piece of feedback a little bit better.

Can you say a bit more?

And it's just those simple language
techniques again that I learned.

Decades ago now can really open up a
conversation and it makes you, like you

are asking them open-ended questions and
not closed questions where you're just

like trying to get a yes or no answer.

And I think that can really help really
open up conversations and critique.

Christian: Yeah.

So I think the key word there is
conversation feedback is an invitation to

a conversation about your work, isn't it?

That's right.

You mentioned about these frameworks
of framing your work that you've got

inspiration from the sales world.

Is there anything more tactical
that we could talk about there?

What's exactly the framework
here that someone listening to

this might take and present some
work that they're doing today,

Alastair: tomorrow.

There's a, yeah, there's
a couple like this.

I'll give one really good book
recommendation, which is Robert

Cialdini, The Psychology of Persuasion.

That's an excellent book.

If you want to know, why people buy
things basically, and the art of how you

influence, like that is a wonderful book.

One of the frameworks that I use
is called the Art of the Pitch.

And It's, essentially six stages
you initially want to set the stage,

create awareness, create need, create
urgency, evaluate your choices,

and then resolve any final risk.

And so this, they're the six
and I'll walk through them.

So initially you want to set the stage.

What can your audience expect?

So again, many people when they're
presenting work, they miss setting it up.

They assume that a lot of people
have a lot of context about the work.

And so you're just setting the stage
about this is a two way conversation.

It allows you as a presenter to
invite the audience in, to understand

the context that you're given.

And you can do that very simply.

The other mistake people make
is they spend 20 minutes on the

context which can be far too long.

But if you think about very practically,
it's okay, I'm going to present a happy

state customer flow for a brand new
customer onboarding to our product.

Not someone who's been invited to join
an existing product of ours, right?

So it's brand new, happy stay.

Okay.

Somebody brand new
onboarding to our product.

That simple sentence.

Like it takes five seconds to
say, everyone's okay, great.

And now again, coming to your point
about feedback earlier, nobody's going

to give you feedback about, Oh, what
about if you're an existing customer?

And it's no, we're not talking about that.

Like we've already set the stage.

Like people have the context.

The second stage is
like creating awareness.

And I think this part again is key.

It's like.

because many people, when they're sharing
work, it's the middle of the week.

People are busy and it's easy
to switch off in presentations.

And so you need to create awareness
about what you're trying to

show and why it's relevant and
important for people to care about.

Okay.

I think that's what's important is like,
why should they care about this problem?

Because they're probably
designers, they're designing

hundreds of different things.

Like, why is this thing more important?

Or maybe you're presenting
to product managers.

It's like, how do you actually.

Make them care about
this problem and I think.

You can do that in very relatable ways
and a kind of technique in Cialdini's

book is like creating a relatable frame.

It's okay, what's, and it's more simply,
that's like an analogy, like, how do you

actually make a real world analogy so that
people can really understand the problem?

And again, using a concrete example,
if you're presenting this onboarding

journey to make it relatable, it's okay,
if you all remember how overwhelming

your first day of your new company felt.

Lots of information to take in.

That's what our customers feel
like when they experience our

product for the first time.

Okay, so you're then making
it very relatable and creating

awareness for the problem that
you're trying to solve, right?

And so everybody can relate to that.

The next section again, very important
is like creating a need, right?

What is the actual need for the
thing that you're presenting?

Because you're going to present a
solution in a minute, but you need

to make sure that you actually
Make sure there's a real problem.

Customer problem that you're
actually designing for.

And I think, there's a great
quote from Charles Eames.

He says, recognizing the need is
the primary condition for design.

And again, we forget that it's
like we, we focus on the solution.

Here's hundreds of solutions.

It's okay, but what's the problem?

What's the need?

And how do you create that need again?

You can lean on data here,
qualitative, quantitative.

You can bring in qualitative samples of
customers struggling with onboarding.

Okay.

But you could say 30 percent of
all customer feedback relates

directly to complexity and setting
up their products during onboarding.

And then if you want to double down
with the quant qual, it's and here's

a qualitative quote from a customer.

It was too overwhelming
when I tried to set it up.

So you can deal with the hard data
and then the qualitative content.

And then it's like, how do you, the
next step of it is to create urgency.

Okay.

So people.

Your audience.

They're like, okay, this is a big problem.

There's some data behind it.

Got it.

How do you then create kind of urgency
for why we need to solve this now?

And again, there's different
ways you can do that.

But one example is social proof.

People will follow what others do.

And so you could reference
competitors there who are using a

simple, a similar design patent.

You could do loss aversion.

There's different psychological
ways that you can do that.

In this example, it's We lose 90 percent
of customers in the first 30 minutes.

Again, that's a big, that's urgent.

90 percent of customers
in the first 30 minutes.

That's 3000 real people.

You're really making this
kind of urgent for people.

And then it's about
evaluating your choices.

So you're now presenting the work, right?

It's okay, here's the work.

These are the different
choices that we have.

And comparing the thing that you're
presenting against other alternative

work can be clever, because, if you're
presenting different options, it's showing

that you've gone broad, it's showing
that you've got different solutions here.

And if you don't share different
options, your audience may be

thinking there's another solution
that I can think of, right?

And so what you're trying to do, though,
is actually compare the two things,

but then drive down to where you think.

The opinion of your opinion of actually
like what the right thing to solve

is, but then, if you want to really
try and close at the end it depends

where you're at in your process.

Maybe that's enough.

It's okay, let's discuss the merits of
these different solutions like that.

We've, that we shared, or if you
have a strong opinion and you really

want to drive to a decision, it's
like you could actually in sales,

what's known as an assumptive close.

It's you can just say, Hey,
this is my opinion based on the

data based on customer testing.

This is the best solution and
the assumptive close is like

how let's move forward now.

Like here is how we will move forward.

Like you're assuming that you're going
to move forward with the solution.

But again, it depends what your goal is.

If you're actually trying to generate
lots of feedback, you may not want

to go to that final step, right?

You may just want to
open it up for feedback.

So that's a very practical way that you
can step through and you help again.

I think the key here is that.

You're setting the work up.

You're providing the right context.

Very simply, you're creating analogies
and these relatable frames, and

then you're presenting work with
choices, and then trying to drive

down to the, to a final solution.

Christian: I think this comes down to
storytelling and just being better at

telling stories, because oftentimes we
know, we know as humans, we are creatures

that respond really well to stories.

And I think.

What I've seen, and I think
everybody has been guilty of this

at one point or another, is when
you're looking for feedback, you

just come really not that prepared.

You just come with the work and
you present it the way it is.

But I think what I'm hearing you
say, and correct me if I'm wrong, is

that before you go into one of these
feedback sessions, you might want to

prepare a little bit ahead of time.

You might want to have
all your ducks in a row.

You might want to maybe rehearse once
or twice the story you want to tell.

Because it is all about story
rather than here are three mock ups.

Which one do you like the most?

Alastair: That's right.

Story I think is very powerful.

Again, stories have been around for
thousands of years of how we share

information and communicate information.

And again, design critique and
sharing work is no different.

You're storytelling,
you're sharing information.

And also, not just design
critique, when you're...

If you're trying to, as a designer, share
that there's this really big problem

that the company should care about you
have to tell a story I think that and

what will happen we talked about habit
formation over time, is maybe you're

earlier in your career, you may need to
prepare before design critique, you may

want to actually prepare, and as you
said, get your ducks in a row around

okay, this is how I'm going to frame it.

This is the context setting.

This is how I'm going to
present the solutions.

This is how I'm going to
present my recommendation.

You may want to prepare that.

But what will happen over time, if
you're doing that twice a week, which

I'm a firm believer that design critique
should happen twice a week in modern

design organizations, you should be
sharing work every 48 hours, basically.

If you're sharing work twice a week, For
48 weeks in the year, you will need to

prepare less and less because you will be
prepared as a person and as a designer.

And then what happens is you can more
confidently present what should happen

as well is that you know the information.

Just more innately, you're not
just, as you said, creating a few

mockups without any context without
understanding the customer or the problem.

If you're presenting the work all the time
and you're framing it in the right way,

you're going to have to know the problem,
know the data, know the trade offs, know

the engineering trade offs that you might
have to make, because maybe you're further

down the line and you're getting it built.

It's like, okay, we wanted to
build it this way, but we can't.

This is the first iteration.

So you're just going to have to know it.

And then again, it's just habit
formation, time over time, doing it again.

And then over time, you should need
to prepare less and less for these

kinds of design critique sessions.

Christian: Isn't this
similar to driving a car?

First time you're in a car Oh,
there's so many buttons, you know,

to shift gears, all of these things.

Two months later, you're driving to work
and realize, Oh, when, how did I get here?

Because it's all habit.

So it's, I guess it's the same.

Another thing that I've.

had a bit of success with is doing
some sort of a pre mortem, but

that's not really the right word,
in the pre mortem, you always ask

yourself what can go wrong here?

And if you do that sometimes
with feedback, so you know,

this is what I want to present.

And then you ask yourself before
you actually go into that feedback

session, what will people push back on?

If I show them this and oftentimes if
you just ask yourself that question or

perhaps you pull another designer to
the side and say, Hey, help me pre

mortem this what will people push on?

What will their reservations be?

What that oftentimes does is that it
sends you back to the drawing board and

it allows you to adjust and optimize your
design work a little bit so that when

you actually do go and present the work,
you've eliminated that feedback because

you've already seen that it was coming.

So that's another little tactical,

Alastair: thing that I've done.

I think pre mortems are great.

We run those at Dropbox and I used to
run them at Atlassian because again,

they're forcing you to think through
what could go wrong with this, right?

As you said, how will people push back?

And then what it does is, because
this is something that I think is

also important as a designer is.

You're being curious about not
just like how it might go well,

but how it might not go well.

And that curiosity is incredibly important
for how you again, build great products,

understand your customers, understand
the business, understand all the

constraints that you need to design for.

As I said, you can do very formal pre
mortems that take a lot of time, or as I

said, just walk up to another designer.

Hey, like really quick context.

What do you think?

Poke some holes in this for me, right?

Like before, before you're going
into the formal critique session,

Christian: How do you get good at this?

If you're coming, if you're just
coming into it and you have.

No idea about these things.

Is there any way of getting good at this
fast or is the answer just, you just

need to do it and you just need to do
it and do it again and again, similar

to what we were talking about earlier
and you're just going to get better

Alastair: and you need
to do it again and again.

I think.

I actually think there is
a bit more to it than that.

But again, if I look back on when
I played football like between the

age of probably six to 16, I was for
various teams, football trainings,

at least four times a week, at least.

So I was training at
least four times a week.

Often six with two games on a weekend.

And so that is, if you think
about that over a decade, right?

Cause that was six to 16, but then
eventually six to 37, like how I played.

It's so much habit formation, right?

And it takes a lot of time.

Cause when I was six, I was, I
was obviously had some natural

talent of football, but I wasn't
that good because I was six.

But over time, like you build that.

And I think.

And then when I look at my design
career, when I started, I mentioned as

a design team of one, I was Designing
in the tool at the time was OmniGraffle

and then Photoshop and we were just
in designing every day and then I

built my own usability testing lab
and I bought customers in every week

and so it was just habit formation.

You were doing the things
and making mistakes.

But then I think I think if I
raise raise that up a little bit.

What I was doing in both of those things,
other than habit formation, was I was

very curious because when I started
my career as a designer, I was making

and doing, which I think you have to
do, you have to make do, but I also

was curious, I was educating myself on
the side, reading every book I could.

Going to design conferences because these
are the days before things like Behance

and Dribble and all the things like, but
like going to design conferences, reading

books we had the start of newsletters.

I got mentors, like I would find
people and again, it's amazing what

happens when you just ask people.

It's Hey, like I'm
starting my design career.

Can you help me?

They're like, sure.

Because often it's the greatest.

Thing that people can ask you is like
for help, because then you're saying,

Hey, you're an expert in your field.

I would love like a piece of,
time and you like and people

are quite often quite generous.

And so I was sought out mentors.

And I think then that.

Habit, curiosity, finding experts to
give you feedback like over time, like

you'll then just build up these muscles
and you'll get better at these things.

And I think.

You obviously have to have some natural
talent, but natural talent alone

without hard work doesn't do it, right?

But if you actually have talent and
you work really hard, you will over

time get better at these skills.

Christian: Yeah.

Thanks for building upon that.

Yeah.

I think that's very important to
reiterate that as you said, even if you're

talented, it still takes hard work over
time and you just need to stick to it.

Alastair: I think the only thing I'd
add as well is we've already touched

on this, but often designers ask
me, they're like, what skills, what

prototyping tool should I be learning?

I'm like how are you honing
your communication skills?

And they're often like I don't know.

I'm like, I know that learning prototyping
skills and Figma and yes, you have

to be a master in those tools because
that's the job, but how you're learning

communication and how to have crucial
conversations and how to listen to learn.

That is going to take
you a lot further, right?

How you influence people through
communication that will take you

a lot further in your career.

If you combine that with the hard skills
of Figma and prototyping and design.

And so I think I often push
people to think a little

bit more outside of the box.

And we've mentioned sales frameworks.

I'm like, learn about sales
frameworks, learn about psychology.

This is like very important as you're
working with cross functional partners.

That you can communicate and
influence them in meaningful ways.

Christian: Let's...

Stay on that topic of some of these soft
skills that are important as a designer.

You've already, we've already talked a
lot about pitching and communication.

You've mentioned quite a few times
curiosity, another important one.

What else is worth mentioning when
it comes to these soft skills?

What else should you be working on
as a designer other than learning

to prototype and learning to
build design systems in Figma?

Alastair: I think it's, it's still
related to craft, but it's like

honing your taste as a designer.

The problem that I think I've seen in
the industry is this is just generally

in the industry is we often whilst we
need to, so this is a very fine line.

So I don't want to count like
you need to listen to customers.

You need to understand the
data from your product, how

people are using your product.

You need to do all of that good stuff.

It's a very important input, but what
we've lost is, I think, the ability to

use our judgment and our taste level
as a designer, as an expert crafts

person, and have an opinion about what
we think the right or a great solution

is, because what often happens is
we're like, oh we'll A, B test that.

And it's okay, like you can maybe this
is something that you need to AB test, but

what is your opinion as a craftsperson,
as a designer, like what is the best

solution, knowing your customer, knowing
the data that you have available today,

because what, what can often happen is
you just start to AB test everything.

And then you actually end up
with something that is not

coherent as a whole, right?

And so I think that the skill
that designers need to continue

to hone is their level of taste
and judgment and intuition.

And you hone that through various ways.

Going to art galleries, , reading
philosophy actually going and talking

to other master craftsmen and going
and looking at some of the older

trades, like industrial design and how
crafts were actually made back in the

day to really understand the level of
detail that goes into something and

why something is really well made.

And that, I think, level of then taste.

and judgment that you will start
to build up will help you just make

better products and make better
intuitive decisions as a designer.

Christian: So we've gone from a lot of
years ago where design wasn't really

seen as a function of business to now
where I think A lot more businesses

are in tune with the fact that design
can make a difference because we are

measuring a bit more, what the output
of our work does for the business.

And then we're at this place right
now, where I think design has to

move some sort of a needle because
otherwise what's the point of design.

What you're saying is that perhaps that's
not the only thing that should matter.

What I'd like to ask is, You find
yourself in a company and then obviously

the company cares about metrics.

They do want to do A B tests
because, hey, if you can improve

the conversion rate by 0.

1 percent that is X dollars a year,
which is a very reasonable ask to make.

But how do you then as a designer
who has taste, who has this

craft can push against that.

Not necessarily push against that, but
can counteract that by saying, yeah, 0.

1 percent is great.

But I think we should do this
other thing because it's,

you know, what would you say?

Is it more tasteful?

Is it more, what would your arguments
be in a way against, you know, a PM or

against a business that really wants this

0.

1%?

Alastair: The honest answer is
it might be in the wrong company.

Because the company has to
care, number one, right?

The company has to care about quality
and customer centricity and craft the

big poster child is obviously Apple, they
care very deeply about how something is

made and they're still run like a big
machine, a big business, but they still

have a high degree of quality craft
taste in the products that they make.

Airbnb is another one more in the digital
age right now where they are hyper

focused on their customer and building.

Amazingly crafted products because they
believe that over the long term, if

you focus on building the best product.

That will lead to the
right business outcomes.

And so I think that, is the honest answer.

Some companies may not operate that way.

They may be looking for marginal gains.

Like they may be hyper focused on
just small growth tactics, to inch

out , like small kind of marginal gains
on their product and conversion rates.

And there's, there are, here's
the thing, there are times when

you actually need to do that.

But there are also times where you need
to take bigger swings and you need to

actually where it may not be the right
thing to just optimize this tiny thing.

And actually, if you design something,
uh, more tastefully, more highly crafted

that really solves the customer need.

You're actually, instead of
getting 1%, you might get 10%.

You might be able to 10x this.

Then you actually have to think bigger.

And again, this is where you may
be in the wrong company because

it may be that the company doesn't
want to think bigger, right?

However, it may be that the thing
that you're trying, the problem

you're trying to solve, maybe
you don't need to 10x that thing.

Maybe it is right just to optimize
that small loop, but then what

are the other bigger problems
that you need to go and look at?

And how do you actually make bigger
progress on the overall holistic

customer experience by actually
thinking about it in a different way?

Don't start with the like,
Oh, we need 1 percent here.

Start with what's the customer problem.

Start with what's the business goal.

And then if the business goal is 1%,
then how do you add a zero to that?

Let's make it 10%.

How would we actually go much bigger?

And then you start to
think more creatively.

You start to open the
aperture for what's possible.

And again, it may be the company or it
may be the problem, is an optimization

problem, or it may just be that you
need to think differently about that.

Christian: So I'm wondering how
storytelling plays into this, because

perhaps some people sit in a business,
they look at numbers all day.

They don't.

have a connection necessarily
to the people using the product.

So that it's harder for them to relate
to them versus someone who can come in

and use proper storytelling, to explain
to them how a better quality product

might actually reach those numbers, but
in different, in a different manner.

So perhaps storytelling
also plays a role in that.

Alastair: It certainly is.

And something that we're doing a Dropbox
it's been a ton of work, but I think

The design team is very engaged and
happy because we're leading the charge

on what the story for our customers
and for the product will be next year.

And so I'll break it down.

We write, we use narratives at Dropbox,
which I think are excellent, it's an

Amazon method where you diagnose the
problem, you define what the obstacles

and the opportunities are, you then create
some guiding policies around how you might

solve those obstacles and then, a set
of actions like for the following year.

And those narratives are rooted
in the customer, they're rooted

in data, so they're very customer
centric, very business centric.

But then what we've, and those narratives
generally span about a 12 month period

or a three year period, and what
we've then done is we've taken those

narratives as a design organization.

And we've worked with our marketing
partners to say, Okay, we've got a

couple of releases next year in 24.

We're working on a biannual release
cycle and so we're visualizing that

in the form of a story or a marketing
page that a customer may see.

And we're using real imagery from
the product about how we might define

the best experience for our customer
that we've, from the problems that

we've defined in that narrative.

And then we're actually working
with marketing to say, these

are the value propositions.

This is the message that
we'll send to customers.

And so it's a form of storytelling.

And it's been very effective because
it takes a lot of words, which are

excellent words, and it's very thoughtful.

But it turns it into something, a
visual story about, okay, this is what

a customer will see on our landing page.

This is the value proposition they'll see.

So that we can see the theme between
the two launches, so that we can see

that there's a strong through line.

And so again, it's it's getting us ahead
is visualizing the road map because we

can then take that and break it down
into a very linear type road map and

it's also the other thing that this is
done for us is that it's we're starting

from a place of what's possible not
from a place of like his let me tell

you the hundred constraints that we
have to work around we're being mindful

we're not being blue sky about the
experiences that we're trying to

ship . We're working with engineering,
but we're pushing the boundaries.

We're not starting from the, as
I said, the 100 constraints and

then working back from there.

Christian: And I like this idea
of thinking what's possible.

It reminds me of an example.

I think it's, it was
Microsoft decades ago.

That started from this idea of putting
a computer on every desk in America.

I think it was something like that.

And that's a very different problem
statement to start from versus saying,

we need to lower the price to 1, 000 per
computer and we need to make sure Word and

Excel are on it or something like that.

the statement is very different.

One of them is about the story and the
place we're going together as a team.

The other one is more
about what can we do today?

And it's, it feels much more, I don't
know, much, much more rigid, I guess.

Alastair: it's the only thing that it
does, because as a leader, your job is

to set the tone for the organization.

And if you're setting the tone
with the price needs to be this.

Then you're immediately putting
constraints on the team.

If you're setting the tone around what's
possible and you're being inspirational,

it's amazing what problems people will
solve when they feel inspired, right?

Because I'm sure there's a lot
of challenges to get to, what

we're proposing to ship next year,
but people are inspired by it.

They see it.

They're like, yeah, I want to
make that that's what I want

to ship for our customers.

And you're then able to, motivate
people to do more than they think that

they're capable of, which I think, again,
is the job of a leader, and it can be

the job of design, really, because you
can show what is possible, and then

people will be motivated to try and
go after that goal versus just, Doing

something incremental, doing something
small, and I think that's our job.

Christian: You mentioned leading
and the roles of a leader.

Over the past 10 minutes or so, you've
talked a lot about taste and craft.

So let's combine those two.

How do you on a daily
basis lead the craft?

Alastair: There's small
things and big things.

Some of the small things are just, I'm
well known in Dropbox for having a very

large t shirt and sneaker collection.

but all of them are
highly crafted objects.

And shows that I care about
what I'm wearing and that I have

a level of taste around that.

And I think that's a small signal,
but it's an important signal, right?

It's.

We do, again, another small thing, at the
end of every week, we have a Slack bot

that asks all of my leadership channel
to share something that's inspired them

from a craft perspective this week.

And so people share multiple different
things, like this week I shared a vinyl

record that's in the shape of a heart.

I mentioned I got married last week.

So I got married last week and,
we had a vinyl record that was in

the shape of a heart, but somebody
had cared enough to make this

piece of vinyl into a heart shape.

And it actually plays on a record player.

It's wild.

But again, so these small things
where you can show that you care about

these about craft is very important.

Bigger things um, You have to, again,
I talked about setting the tone, but

my job, I see as a leader has been
to start the movement and show that

from the top down, that I care about
craft and that it matters to me.

And so I spent, we had our, all of
our designers together in February

and Austin, Texas, and we had a whole
two day event around craft, what it

means to me, what it means to the team.

Why it's important.

But the main message was, it's
important to me, you have my

blessing that I care about this, but
really, I can't do this on my own.

I need all of the 150
people in my design org.

To start the movement from the ground
up like they need to get on board

and so your job as a leader is to
start that movement set the tone

show what great looks like but then
inspire other people to take up the

baton and actually make the change
that you need in the company and so.

that message I think is important.

And I followed that message up.

I share top of mind posts, which are
like internal blog posts every month.

And I talk about craft and I talk about
the progress that we're making and

I talk about the things that matter.

And so there's some of the bigger things.

And then also, I'm looking at
end to end customer journeys.

We follow the.

See, buy, try, use.

So it's okay, I see it on the website.

I try it.

Okay.

So that's onboarding.

I then buy it and then I
use the product, right?

Okay.

So see try, buy, use.

I actually.

Look at all of the end to end customer
flows that are shipping in our two

launch moments following year, like
for a full day every other week.

So every other week for a whole day, all
designers are coming in and presenting.

This is the progress on
the onboarding states.

This is the progress on our
preview screen, whatever it may be.

. And so literally like eight hours
every two weeks, that is all I'm doing.

And again, that's a big message to send
to a design organization that I care

enough that I'm looking at this and I'm
talking about like small details and it's

not, I don't see that as micromanagement.

I see that you're showing that you
care about the details and you're

again, so long as you're framing your
feedback in the right way, it shouldn't

come across as micromanagement.

It's just that, You care about the details
because you want the product to be great.

So therefore, how do you share that with
someone so they can improve the details?

And so I think there's small things
and big things around craft and taste.

Christian: I think some of the best
design leaders I've ever worked

for all had one thing in common.

They had differences.

Some were good at this, some were
good at that, but they all had

one thing in common and that was
that they were able to inspire.

The entire design organization.

And since we've talked about football
a little bit, I'm just watching

the Beckham documentary recently,
and I'm a big football fan myself.

Over time you've watched inspirational
leaders like, Paolo Maldini and John Terry

and Carlos Puyol and, all over the world
or over Europe, mostly I've watched and

you see all these leaders and really a
lot of what they do is that they inspire.

And the interesting part is that
they don't inspire through words.

They inspire through doing themselves.

That's right.

I guess it's what you're
talking about here.

It's just inspiring through,
through showing that you care.

Yeah.

Alastair: It is.

Because, linking it to influence, how do
you influence cross functional partners?

Show don't tell, right?

Like that's the biggest thing, right?

And how we've, we just had a big launch
in October and the product has changed

dramatically, the Dropbox product.

And it's very like the web surface
and very well designed, integrated

workflows, high care for visual
craft, interaction design.

And people would ask me like, how
did you get this on the roadmap?

How did you, it was like.

We showed like we did the work of creating
like better quality design we spent the

time and then we were showing that to
our partners and again inspiring them

that this is like this is what it could
be how do we make this do we need your

help like how do we make this happen
and so I think that is very important

that showing don't tell not telling
and leading through action because.

I'm not pushing pixels day to day,
but I am in Figma files, right?

I am showing that I care, right?

And it's again, you
have to walk the line.

You don't want it to become
micromanagement and a fear based

culture or anything like that.

But actually being in the details
and being in the files, That's

just showing that you care.

That's showing that you care
about the details and that you're

willing to put the work in with the
team to actually make it better.

Christian: On that same
topic of inspiring others.

It's not so much only at a
leadership level, but also

as an individual contributor.

I have countless examples of
showing what's possible to someone

who doesn't really care that
much, let's say to an engineer.

But once they've seen that, once
they've seen where you could take it,

they're suddenly much more likely to
appease you when it comes to a little

animation here or little things here,
because you managed to inspire them.

I think that's one of the power that we
have as designers is that because our

work is so visual we can put examples
that others have given or ideas or

thoughts into something tangible
and inspire people through that.

That's one of the superpowers that
we have as designers, I guess.

Alastair: it is.

It's interesting because I think for a
long time, we've shied away from using

that, but we've been like, Oh well, I
don't want to just be seen as the person

that's like visualizing something.

And it's I don't think we are.

It's, but that is our superpower.

And as you said, it can motivate people.

And the best design relationships
I've ever had, and I see in my teams

are where Designers and engineers,
mainly, but designers, product

managers, engineers, the kind of core
triad are really tight and they're

doing exactly what you're saying.

They're like in each other's details.

Hey, like engineer the
animation is not quite right.

Like, how do we make this
like, here's a prototype.

And again, if you show it,
you can inspire people.

They'll go above and beyond.

They'll be motivated to do more
than what they think is capable.

But also you're just showing that you
care and you're partnering with them.

And you're close to the details.

The inverse is the worst teams
where it's like a handoff process.

It's here's the file.

And it's nobody's inspired because
they don't know the why behind it.

They don't understand what
you're trying to achieve.

They just see a file.

And I think that tight partnership,
it can go so far in building,

like, better experiences.

Christian: Yeah, in my experience,
I've heard it often times.

Designers say my engineers don't care
so much about the end product . In my

opinion, that's very rarely the truth.

The truth is that perhaps you haven't
done a good enough job at inspiring

them, because I've also seen and
been part of teams where if you are

able to inspire your cross functional
partners, you have an engineer who

comes and says, I think the experience
for a user could be better here.

It's stuff that you hear
normally from a designer.

You can't hear that from an engineer.

If you bring them on board as to
why it's important, so being able

to inspire, I find that to be
a very good sort of soft skill.

Alastair: It's that inspiration,
but it's also starting with why.

There's a great book, Simon Sinek
start with why , if you can get

people to really understand why this
is important and it comes back to

that communication framework, right?

Create urgency.

Like, why is this thing important
to like really solve well?

And then you can also inspire
them with a great solution.

That's where magic's going to happen
because people are like, wow, like

I understand why this is important.

I see an amazing solution.

Let's like try and move mountains
to make this thing reality for our

customers and for our business.

Christian: Alistair, if we were
to sit here in 10 years and have a

conversation and you are, to say,
Christian, this last decade in

design has been absolutely amazing.

What would've had to happen for you
to say that to me 10 years from now?

. .
Alastair: I'd like to think that 70
percent of what I just said is still

accurate and 30 percent is wrong
, because I want to keep learning and

developing as a leader and as a person.

And so I think, I want to
keep learning new things.

And so I would like to look back
personally in a decade and be like,

all right, I learned something and
something I said was not right.

I think that, that would be important.

That's just my own growth mindset
of trying to continually learn.

I think from a design shape,
there's a couple of things.

One is it would be amazing to see
more design CEOs and design founders.

I actually think that
would be very interesting.

not because I think design is special.

It's just more designers have a different
way of thinking about problems in a

different way of like framing problems
and approaching problem solving.

And so I think having more designer
CEOs and designer founders in the

kind of fortune 500 would be like a
very interesting and inspiring thing.

The second would probably be.

Just that we've, as designers,
we've really got, really gotten

back to our roots of craft.

And this is one, again, it's a bit
more personal, but that we're, we

have to understand, as designers, we
have to understand the business, how

it makes money, be a good partner
to cross functional disciplines.

I think that's just, like you
mentioned design is now more

respected in organizations.

And so with that respect, we have to
be good cross functional partners,

understand the business, In general,
but the thing that I think we've lost

in the last five, 10 years that I think
we need to get back to is just then,

yeah, understanding the business, being
a good partner, but going deep on our

craft and just inspiring, like we've
talked about this, like being curious

and then inspiring with really great
solutions and leading through design.

I think that, that would be a really
good mark of success and attendance.

Christian: We've got a little
tradition at the end of the podcast

. We, I keep saying we, I don't
know why I say we, it's just me.

And ask the same two
questions to everyone.

And the first one is what is one
action that you think led to your

success that in a way or another
separated you from some of your peers?

Alastair: One action, I don't like to
compare because I think everyone is unique

and special in their own way, but I think
certainly something that I did early on

was I just had this curiosity to learn
about design and different disciplines.

And I then just went and did the work.

I think because of my roots in football
like, I understood that it was just

habits, doing the work, showing up.

And even the roots I have today
like, I exercise still every day.

Not every day is a great exercise
routine, but I turn up and I do the work.

And so, I think that
curiosity in doing the work.

Was really pivotal early on in my career.

Christian: The last question
is, what are we not talking

about enough when it comes to

Alastair: design?

I would probably say craft still,
like, I just think there's been

a natural tendency over the last
decade to, Hey, it's a process.

It's a double diamond.

Anyone can do it or it, or there's been
a natural tendency because I've even

written about this of understanding
the business as a design leader.

And I do believe in that, but I
think that with those shifts,

we've lost the deep focus on craft.

And the deep focus on leveraging
our craft and leading through

great design and great taste.

And so I don't think we're
talking enough about that.

Christian: It's very fascinating for
me to see that in one hour conversation

that we've had, someone who is very
high up in an organization as a designer

still cares so much about craft.

And I think that should be an inspiration
that craft is not only something you

should care about when you're contributing
on the ground and designing in Figma every

day, but also something that you can keep
with you when you go higher up as well.

So thank you for that.

This has been A great conversation.

Where can people find you if they
want to get in touch with you or

read what you're writing or any
sort of places they could go to?

Alastair: Maybe LinkedIn nowadays,
uh, I am still on X, but I

don't, I'm not active on there.

So LinkedIn, I have a lot
of older articles on Medium.

I haven't written externally
for a little while.

I write internally at Dropbox, but
yes, LinkedIn is the best place.

Christian: LinkedIn it is.

We'll put that in the show notes
where everyone can find you.

Alistair, this has been
a great conversation.

Again, thank you very much for being
part of the podcast and, I hope that

you enjoyed it as much as I think
people will enjoy listening to it.

Alastair: I always have a great time
sharing stories and anecdotes because I

genuinely believe that we're all solving
the same problems and the more stories

that we can share about how we're solving
them, the more effective we'll all get.

So thank you for having me on Christian.

It was a true pleasure.

Christian: If you've
listened this far, thank you.

I appreciate you and I hope you've
learned something that makes you just

a little bit better than yesterday.

You can check out the show
notes on designmeetsbusiness.co.

If this has taught you anything,
please consider leaving a review

and sharing the episode with someone
else who could learn from it.

And I'll catch you in the next one.