Design Meets Business

Christian: Josh, it's a pleasure to
have you on Design Meets Business.

Welcome.

Josh: It's great to be here.

Thank you for having me.

Christian: Yeah, of course, of course.

Let me start by saying on air to be
witnessed by everyone listening to this,

that you are one of the best, if not
the best designer I've ever worked with.

I appreciate that you're taking
the time to chat with me today.

You've touched just to give a
little bit of an introduction,

products from booking.com

to Ford spent years at Google
designing for billions of people.

Then you had a Stinted Zoe, and now you're
at Microsoft working on AI in healthcare.

Needless to say, your work has,
and my bet is that it'll continue

impacting a lot of uh, people.

So let me ask before we go into all
of that, how did your journey begin?

What's your design story,

Josh: I go all the way back to school.

And it's interesting because I see
a bunch of people I walk my dog with

in the morning who ask me about this
because, typically I think the thought

of working at like big process tech,
Google, Microsoft, half my team are

gps that I work with at the moment.

And I did not do well in school at all.

I think I passed two GTCs, GTCs are
like what we get in the uk, right?

And I didn't do well.

I didn't know what I was gonna do.

I spent a long time trying to
understand why I wasn't great in

school and what I was good at.

And it just turns out that
my brain is better at like

kinetic thinking ultimately.

So I'm better at doing than I am sitting
and reading a book and processing those

things, I just wanna go out and do things.

And so it was really when I left
school and said to my parents,

I'm not gonna do school anymore.

I'm gonna go and study this
thing called like multimedia.

And I started to do well in it and I
went from the bottom of my class to

the top of my class very quickly just
because it aligned with my process

and my way of working ultimately.

I then went and studied advertising off
the back of that, we had a teacher come in

and pitch to us when we were in college.

And I was like, I'm
gonna go do advertising.

Sounds great fun.

And then the reality of like
finishing that degree here and I

was walking around London with a
portfolio knocking on agency doors,

just going can I have an internship?

And they were like, no, why are you here?

Go away.

And it just happened to be at
the same time to make some money.

When I was in uni I was like
designing websites on the side, which

I never thought I'd make money of.

I didn't know it was a
thing, being in South Wales.

And I got offered a job I can't even
remember how I got for this job.

A John Lewis right?

To be a digital designer.

At the time there was
no John Lewis in Wales.

So I'd never been to a John Lewis
and I went for this interview.

My dad drove me up and I was
like, I don't want to do that job.

I don't know who John Lewis.

I like, I want go and
work in an ad agency.

And my dad was like, you
are gonna take that job.

It's a good job.

And ultimately it worked out in
the end and I bounced around a bit.

I loved my time there.

It was a really fun job.

And I spent some time there, I
moved back towards Wells when

I had a girlfriend at the time.

Went to an agency for a year.

Ended up calling my old manager John
Lewis, be like, I wanna come back.

I really miss it.

Have you got any work?

And he's like, no, but I know
someone who does in the company

and they needed designer.

My PM at the time, Victoria
Ludlow, who's fantastic.

she was like, can you do product design?

' cause we just need a product designer.

And I was like yeah.

I could definitely

do

Christian: Of course I can.

I

Josh: Yeah, of

Christian: it can I can figure it

. Josh: yeah, Yeah.

And I just made it up from there.

And here I am.

And I've loved every minute
of it so far as well.

It's been great.

So

it's a rollercoaster.

Christian: you work doesn't seem to me
like you're making it up, so I dunno.

I think that's a heavy understatement,
but uh, everyone has their own perspective

and then uh, you know, John Lewis.

Okay.

You had a, a good time there.

How did you end up in Big
Tech and why Big Tech?

Why was it so attractive
for you to try Big Tech out?

Josh: It's a great question.

I did some work after John
Lewis where I went to Hive and

I worked on Connected Home.

I've always been into tech, right?

Like, I've always been into like
computers and just stuff like nerdy stuff.

I just didn't know how to like,
express myself in that world.

And I had this might not maybe
look the best, but like I'd always

applied for jobs at Google, whatever.

They came up and it took me
seven years to get an interview.

And it was so funny, I was working at Ford
at the time and I got a call just because

I saw this job come up and I applied and
they were like hey, we're interested to

talk to you about this job on YouTube.

It was on YouTube at the time.

and I was like, oh my God, yes.

Amazing.

This is what I wanted.

Like, I just want to
get into this process.

And she was like um, cool.

So we, we, we wanna start this
process with you and start

speaking to you about this role.

You know, It's in Zurich, right?

And I was like yeah, yeah,
yeah, yeah, yeah, yeah, yeah.

Like I, of course, of course I knew
that, I know, I didn't even realize I'd

applied for this job in Zurich, basically.

And then I, took a break, so I was
contracting forward and so I said,

I just need like two months off.

I was so like, I want this job so badly.

I don't even know if I
need to move to Zurich.

I don't know how I'm gonna do
that, but I wanna do this job.

I like stopped working for two
months to do this interview and.

Just like work my, it was my birthday
and I remember sitting in a cupboard

at my parents' house, my birthday
when everyone was having a party

in the garden for my birthday.

And I was like, I can't join the party.

I need to do this portfolio piece.

And I was just sitting in this
dark cupboard for like, most

of the day doing that work.

And it ultimately was just a, it was
an ambition of mine because I wanted

to work on things that touched lots of
people's lives, And there's not really

a bigger scale you where you can work at.

I didn't even end up working at YouTube.

I ended up working on maps, which
is the product I'd always wanted to

work on very fortunately as well.

And it's like one of the, my
favorite jobs I've a today as well,

Christian: I think that's
just a great story.

You should tell that story more often.

. I didn't know about, as in I knew
that, but I didn't know about the seven

years of applying or hoping for it.

And I guess it also shows, you said it
might not make me look good, but I think

it does the opposite because it shows that
sometimes to get the things you want, you

gotta put in a bit more work than most
people probably give up after applying.

A couple of times they'd be
like, nah, doesn't work for me.

They don't want me I
don't think I fit here.

I'll go try something else.

You tried for years until you actually

Josh: So, and it's one of these really
interesting things I think where it's easy

if you know someone there at well, right?

'cause you can get a referral
and you can get to the process.

And I think one of these walled
gardens places, I never knew

how to get into because I was,
I didn't know anyone at Google.

I didn't know how to
meet people at Google.

I was going to design talks all the time.

Like I remember the time that, when
Monzo was like skyrocketing and

they were doing like these design
talks once a month, design club.

And I'd go all the time and I would like
talk to people and I'd be like actively

looking for people who worked there.

And I just never met anyone that worked
there to be able to get into enough.

And so it's one of those things
where as you said, it was just

me, being persistent essentially.

Christian: Ah.

I mean, That is, if there's one
quality that matters a lot, it's

being persistent, I think, and it's
one of those things that you don't

necessarily have it when you're born.

It's one of the things that
everyone can be, you don't need

to be talented to be persistent.

You just need to be persistent.

So I love that.

Josh: Agree.

There's the other side
of that though, right?

Which is failure is like the enemy
of persistence in a way, right?

Because it, because if you fail, I
think you can ultimately be so down,

so downtrodden, you just move on to
the next thing, And I do think that

like stubborn persistence gets you
there in the end, ultimately as well.

Yeah.

Christian: So you finally end up
at Google, you work on maps and

you realize, oh, now I'm designing
for A billion people, if not more.

. What does that mean?

How is, how do you do that shift of, okay,
now I've designed on, you know, for Ford

for a few people, you know, booking.com,

obviously big scale, but not that big.

What does that mean on a daily
basis for you as a designer to

now just design on that big scale?

Josh: I, it's interesting 'cause I think
the, because I've done both and I jump

between the two as in like big scale and
startup, and I think ultimately people's

expectations are, if you're in a big
company, you are just redesigning a bun.

That's not true.

The hardest I've ever worked is in these
big companies and , one of the kind

of pivotal points when I joined Google
was I, I had this sort of mentality

that I had when I was at Booking.

We were designing these taxi
flows for their booking agency.

It would be very quick, it'd be me and
three engineers in a room with my PM just

being like, okay, what are we doing today?

This thing, we're gonna go and
design this and push it out.

Whereas when I started Google,
I had that mentality in my

head and I had to unpick it.

So I started to, I went to my manager
and I was like, yeah, here's a flow.

What do you think?

Best, one of the best
managers I've ever had.

And he looked at me and was
like you know that you have all

of this uh, your will, right?

You can go and work on street view.

You can tap into like user reviews.

You have the world mapped and you're
just showing me this little flow.

take it away and think bigger.

And I think that was such a pivotal
moment for me because it taught me that

I didn't always have to think small
and constrained and iterative, right?

Like, I can go big.

It may not be the ultimate thing
that I end up shipping, but I

think it's effective to do so.

and I think partly that's down to aligning
people behind like a mission, right?

That's why that's good to do.

But also because it really is
the power of a designer, right?

Is to think ahead of everyone
else and like tell that story that

it rallies everyone behind it.

And that's something I like really learned
when I went into these big companies is

in my view, a designer's power is the
ability to like pull everyone together

and align everyone behind a problem.

And I think you can do that
in a lot of different ways.

The way I was typically doing that
back then was to think big vision

this, pull everyone into this and show
everyone how amazing this could be.

And then gradually what
towards it as well.

There's a lot of other things, right?

There's a lot to do with
managing people, right?

There's a lot more people to
get designs through, right?

If you're just like in a scrappy
team doing stuff and pushing stuff

out, you don't really have anyone to,
that you're accountable to big tech.

You do.

Right?

And there's a lot of VPs and there's a
lot of people with a lot of opinions.

And so I think now that I learned a
lot about navigating that and building

conviction in your ideas and helping
others to build conviction and why your

ideas are the best direction as well.

I also think the responsibility
is so much bigger So there's

these two pieces, right?

Which is like thinking big, making
sure everyone's bought in, but on top

of it, responsibility to it, right?

And we, and we're gonna talk about
this later around ai, but that's like

ultimately true with AI now, right?

It's like we're working at speed.

These companies are working at like
incredible speed, but there's a

huge responsibility behind that.

You're starting to see the unraveling
of that now with like open AI

getting sued recently as well.

And so I think those are
the three biggest things

I learned about moving into companies like

Christian: to dive a bit deeper into that.

One of the interesting parts of your
work that you've mentioned there was

aligning people behind the mission.

What does that mean practically?

How does that look like?

How do you do that on a daily basis?

Josh: There's a few parts behind that.

One is storytelling A super power of a
designer is being a good storyteller.

I think that is true for
many different things.

But I think one of which is like
getting people bought into your idea.

The second I think is making
sure people are heard.

I think that's really important.

But I think the third is knowing
who to listen to the most.

And who has the loudest voice in the
room isn't necessarily the person that

will be signing your work off, right?

And so there is this there is
a bit of a balance with like

accountability here as well.

And I, I take this stance of
I'd rather ask for forgiveness

rather than permission.

Which sounds counterintuitive to
like what we're talking about.

It sounds like the opposite thing.

But actually what I'm doing is like
showing my work proudly showing my

work and like asking for feedback.

I'm not Asking for people
to tell me what to do.

That balance is very nuanced because
ultimately I'm in reviews now and I'm

talking about really difficult subjects,
Um, and a lot of people have opinions.

I think the best stance you can take
is everyone's very clever in a room

typically when you're there, right?

There's a lot of very
clever people in tech.

So a lot of people are gonna
have opinions about your work.

I think it's really important to
sort of try and cut through the

noise and understand ultimately whose
opinion will help you get your work

across the line the most, right?

, There are people who will have lots of
opinions that ultimately don't need to

sign your work off to get it live, right?

And I think what you should have
is like a deep trust in yourself

that you know what you're doing and
that you understand your craft, and

you can get this across the line.

I think people's feedback is really
useful to help shape a product and

help shape your view of things.

But ultimately, you
are responsible, right?

Like you are the direct, responsible
individual for this work.

So you should have conviction about that,
you should learn who you need to work with

to get that work across the line as well.

That was a bit rambly,

Christian: No, it makes a lot of sense.

And I want to touch upon something
you said there, which I think is very

important, making people feel heard.

When you do a design review or you share
your work, async or whatever it may

be, everyone can have an opinion and
everyone will give you their opinion.

But you as a designer, you have
conviction, like you said, and you

know that some of these are perhaps
not valid because you are the only

one who knows the full context.

Someone comes with an opinion,
they're just, the opinion is just

based on what they're seeing, but
they, they're not seeing the work

you've done behind the scenes.

Right.

But how do you communicate that?

'cause nobody wants to hear actually
your opinion is not valid in this case.

Even if it's not, nobody
wants to be told that.

So it's a very fine balance.

how do you deal with feedback from people
who maybe don't have the full context,

but what, how do you make them feel heard?

That's so important.

Josh: I think that partially that
comes down to listening to them

what I'm not saying is that like, I
don't listen to those to those ics.

Or managers or staff in that respect.

So, I think what I'm saying is that
I, you should know when to listen

to your gut versus listening,
like telling someone, telling you

what to do, ultimately as well.

You as the owner of this work, as
you said, will know best, right?

Like you have the detail behind this.

You've done a lot of thinking and
craft behind this, and part of it is

hearing someone out and understanding
their view noting that, and either

explaining why you think that might
not be the right direction or aligning

on a direction forward based on
that there's two parts you can take.

Sometimes people come in with
like sweeping assumptions, right?

And then ideally when you take it to
these meetings, you would have some

like data to back up your work, right?

Whether that's like uxr.

It could be quant, qual, whatever
you think whatever you have

behind you to back up that.

And I think evidence is always
a really strong way to have

conviction about your work as well.

Or ultimately understanding the person
in the room that you can note feedback

from and and follow up with, but
not let it overwhelm you and change

the direction of a product, right?

I think that's like a
nuance balance as well.

And so I think it depends on who
the individual is on how much

you drive that as well, right?

For example, is it, top level senior
leadership that's giving you this

feedback from a different product,
you know, a different product area

that's maybe giving this feedback.

It's probably worth following
up with that person right?

As well.

Maybe the thing you can do is lean
into whoever the product person

is in your team that's helping you
drive your product as well, right?

And pushing that towards
them to help manage that.

Maybe it's an IC designer from
another team that has a view on

like, how you should design this.

And I think then that's down to you
to align on that can be a quick,

10 minute syn to kind understand
their opinion and hear them out.

It can be something that you follow
on with as a, you know, like a B 1.2

or whatever with off
the back of your work.

There's a bunch of different ways
and I think the scale changes

depending on who the person is that
you are the feedback comes from

Christian: It's so nuanced, all of
this, and there's so much to balance.

I am often thinking when people
say, oh, AI will come and take

your jobs, which part of the job,
because the designer's job is.

Not only to create the artifact, right?

If anything, that's probably perhaps
one of the most straightforward

parts, but is managing people's
opinions and knowing, like you said,

who, whose opinion to follow and
who do you need to just communicate

with in a bit of different manner.

There's just so much management of
opinions and feedback and other people

yeah, it's just not so straightforward and
it sounds like this is the type of thing.

This also segues into a different thing
that I wanna talk to you about, which is

staying on the IC track and gaining more
influence in the company on the IC track.

And I think this segues really well
because one of the things you're

describing is that once you become
a bit more senior and you choose

to stay on that IC track, or part
of your job becomes managing all

of this, not, it's not just design.

If you think that you're gonna stay on
the IC track and not have to deal with

people and just stay in Figma all day.

You are probably wrong, even on the
IC track, you will still probably even

more than before, have to deal with
people and opinions and, all of that.

So what does that mean then?

Okay, you are you're a senior
designer, you have done really well.

You decide, I don't think this
management thing is for me, I want

to gain more influence by, leading
craft or, getting better at the work.

But again, practically for you on
a daily basis, what did that mean?

The moment you've made a
decision to stay on the IC track?

Josh: I think that ultimately what
happens when you move into that space

is you move outside of a remit of
delivering something within the realms

of your core functionality to like
influencing other teams and working

with those other teams broadly.

And I think something I'm working through
now is it's a lot of very busy people

. And the role moves away from, um.

hey I'm, I'm designing this lovely
flow that I'm really into, and I'm

gonna rethink about this and go really
deep here to how do I get alignment

and drive change between teams, right?

Within an organization.

And so, if you think about where
I'm now in Microsoft Health,

there's three to four squads.

I'm like the core designer across those
squads who ultimately have this one goal.

And so the question becomes how do
you align all of those people before

you even do the work then right.

As well.

And part of that is
doing the work in tandem.

Part of that is getting people
in a room to like bash heads

and like, make decisions, right?

And so I think of it as being
more of a shepherd of product, To

help people align and make these
decisions as well as jumping into

the tools and icing and designing.

There's a lot of influence to
be had outside of design, right?

That carves a path in front
of you and makes it easier to

move forward with your design.

I think that's something that extends
from being a senior to a lead and a

principal is like, how do you, how
do you get ahead of where you are

to make things easier when you are
ready to deliver the design as well?

Christian: I think something you
said earlier perhaps already plays

into this, which is you have to
be really good at storytelling.

You have to be able to rally the
team around, and not just your team,

not your squad, not your immediate
squad, but everyone in the company

or perhaps other squads as well.

Rally them around the vision,
whether it's your vision.

Or the vision that us as
a company have decided on.

Is that something you get better at
with experience or is that something

you can learn or is that innate in you?

What are your thoughts on that?

Josh: I definitely think you can
get better at it it comes back to

that point before around like having
conviction in your skillset, right?

So I think there is a, I think there's
a tipping point as a designer, like

when you know you can design, broadly
outside of that, then being able to

rally people around an idea or get
people aligned around an idea to drive

that forward is just something I think
you can iterate on and learn over time.

That partly is down to being willing
to just like, give anything a go

and having confidence that like none
of us really know what we're doing.

Ultimately all of this is made up, right?

Everything is made up.

So like why not make new things up, right?

And try new things here as well.

There was a job I was in at Hive when
I was like designing smart homes and

I just read the Google Sprint book and
I was like, I went to my manager and I

was like, cool, I wanna do the sprint.

And she was like, why?

What are you talking about?

i'm gonna go speak to my pm.

I'm gonna see if I can
convince them to do it.

And I think you end up in this interesting
place where what you have to let go of

is this idea of like, perfection, right?

in the Sprint book, everything's
over five days and here is the

five days and here is the schedule

I don't know about you.

I've never been able to find anyone
with five days free in a row.

So I'll tell you what , Let's
take it, let's do part of it.

Let's just do the half day, maybe I
can get someone for half a day and I

can get started on this thing , that
will unblock me and get me ideas.

And I think what I start to learn off the
back of that is you can do this however

you want, there's no rule book really.

There is this idea of rules and this
idea of process, but ultimately like

it ebbs and flows and changes depending
on what you're working on, who you're

working with, how busy people are.

And so what I started to do is take this
sprint process and do half day, maybe an

hour, maybe like an alignment sprint for
an hour where I just get people in the

room and I think I'm taking that with
me now where I could just get people

to like talk for an hour, which they
won't usually do interestingly, people

don't make time to do that, right?

To like just sit in a room, throw things
on a board and have a discussion about it.

in the pace of business
that's gone away now.

I think part of it is just saying
fuck it and giving it a go.

And having the confidence to fail and
try again is a really big part of that.

And I think you'd learn by just
doing that ultimately and just

iterating on that process and it
doesn't need to be structured.

Right.

If you were to ask me how I run
my workshops, I wouldn't have

an answer for you because the
workshop changes every single time.

I do a workshop.

I did three one hour workshops last week
and I can't remember what I did in them

because the week before I did three more
different one hour workshops as well.

Ultimately each goal is different and
what it's taught me is that you're

better off just like rolling up
your sleeves and giving it a go and.

You can learn and craft off the back
of that, and that can help direct you

to where you need to be to get there.

I always think that, I always think
that if you just give anything a

go, you can do anything you want.

It's just about having the
confidence to be a bit shit at

first, and I think that's fine.

Christian: Yeah, and it is one of the
things that I've noticed about how

you work is that There's no set way.

You don't have a playbook per se.

You break the playbook.

But I think in order to be able to break
the rules, you need to know the rules.

So you said in the beginning you gotta
have your foundations, you need to know

or believe I can design if everything
fails, I can always go back to the craft.

And I'm good at that.

And then you build from that.

Because I think it's much harder to do
the things that you're talking about

if you don't have the confidence that
you do know what you're talking about.

And I like this idea of experimenting.

You don't only experiment with your
product, you also experiment with ways

of working , the workshops and whatever.

So that's one of the things
that I've noticed about you is

that you never have a playbook.

You never know what a Josh
workshop would look like.

You just know it's gonna be new,
it's gonna be different, and you're

gonna get something at the end.

What you said, I think if I miss remember
correctly, is the willingness to fail,

the willingness for it not to work out.

The more senior you become, the more
likely you are to wanna do that because

you think, oh, I have this reputation now
that I want to keep and I can't be seen

to fail, or I can't be seen to run a poor
workshop but at the end of the day, it's

those people who are willing to take those
hits that do the best work, isn't it?

Josh: Yes, I agree.

I think there is something else as
well, which is just work is serious.

Sometimes the work you
do is really serious.

As well.

Some of the things I'm working
through in this role in

particular are like very serious.

But also work has to be fun And I
do think that's another lens that

design stuff's another superpower.

It's like a card you can pull
out you are crafty, you, like

we color things in, right?

We are the colorful fun people in the
room and I think we should carry that

through and I think it builds energy in a
room that most people don't have as well.

So I do think there's an opportunity to
make it fun for people by doing that.

I'll constantly go in and just be
like, okay, I need like an icebreaker.

What can I do?

And I'll try and find like the
funniest thing I can find online.

My favorite one, I come back to time
and time again, which is always fun

and everyone has a good time doing,
and I'm pretty sure I've got you two

is ten second animal where I just drop
a picture of an animal on the screen.

I get everyone to draw it with
like the janky Figma tools in

Fig Jam and they have 10 seconds.

No one does a good job of that.

But it's fun.

And it's funny and it's funny ultimately,
'cause I think people's expectations

are, you're gonna come in and like
do this beautiful Platy person.

It'll look amazing.

Ah, mine's the worst by far in that.

And I think it sets the playing field.

It like evens it out for us all
to have a nice discussion without

boundaries and roles in here as well.

And I just, my ultimate goal
is to like, make this fun and

collaborative as opposed to serious

Christian: I love that
point our job is also fun.

And it reminds me, many years ago I used
to work for this very serious consultancy

where the type where people go in, in
suits and all of that, and inside of that

we had a sort of the tech department where
it was not suits and ties, but it was,

pretty serious type of clothing, right?

You had to look a specific way.

And without even thinking about
this, on my first day, I turned

up to work in this oversized white
t-shirt with colorful ice creams on

it and jeans and I, some funky hair.

And I remember getting in the elevator and
feeling in instantly that I'm outta place.

But the funny thing is, you do that for a
while, you lean into who you are and you

start pulling people in that direction.

And suddenly, not just the work,
but the team dynamics are a bit

more fun and a bit more loose.

And like you said, work.

It's serious and I'm not saying it
shouldn't be, but can you do serious

work while also having a bit of fun or
leaning into who you are personally?

And I think that's another
way of influencing the team.

We've been talking a lot about influencing
today, and I think that's another way.

It's not just influencing through
your work, it's also influencing

through the way we're working.

And then when everyone else is
at ease, then their brains can

focus on the brainstorming or
coming up with ideas or Yeah.

You kind of set the playground for
them, like you said, rather than, Hey,

we're here to have a one hour serious
workshop now come up with some new ideas.

That's just not gonna work.

Josh: Yeah, a hundred percent.

And it's interesting 'cause I, this
was if you indulge with me for two

seconds, I'll tell you about like how
I learn this like really young as well.

Right.

And it primarily is through
like my mom and my nan right?

Who are the most creative people
I know to an extent where like, I

don't feel like, I'm like, how am
I, how are you not doing my job?

Because they are like next level, right?

The two of them and I grew
up in an environment where.

It wasn't shamed to dress up and look
stupid, We go to these events and my

nana dressed me as like a little pig, And
we'd like dance around or like a clown.

nearly every picture of me as a kid
is like, all of us are just dressed

up doing something stupid, right?

And I think part of that then lent into
me coming forward with the confidence

that like, you can look stupid, but
like, have fun at the same time.

And that's something I learned like really
young and take with me wherever I go.

Like I, I put that squarely down to
like my upbringing I prefer to be

the silly, stupid person in the room.

'cause I think that's like a, it's a bit
of a what's the word I'm looking for?

Like it's a bit of a palette cleanser
And if anything, I think that's like

another power . And I think that a lot
of designers I've met have that skill.

They just need to leverage that skill

Christian: yeah I, I think environments
we work in sometimes, because they are

so fast-paced, because they're super
serious, because we're dealing with these

complex products and complex ecosystems
and data and analytics push people

towards the more serious, and again,
work can be serious and is serious.

I do think that there are a lot of
benefits to unlocking some of the

other part of joy and fun and a bit
of just being a bit loose, especially

when it comes to being creative.

It's hard to be creative when
you are stiff whether that's,

physically or up in your head.

One of the things that I like doing
with you and something I've discovered

a few years ago is jamming.

Jamming is fun, and it is.

People will say how fun is jamming?

Jamming is as fun as you make it.

I'm gonna give our listeners a bit
of a, like a 32nd overview of how

our jamming sessions look like.

Then we can unpack some of that and
talk about why do they look like that.

What was good about them and why do we
continue doing them after we started?

So we get on a huddle.

I reach out, Josh, do you got 10 minutes?

Yep, I got 10 minutes.

It never ends up being 10 minutes.

Usually it's about at least half an hour.

But sometimes it, sometimes
you cancel calls because you're

still jamming and it's good.

I have this problem.

I've looked at it for two days.

I have no idea what else I can do here.

I've, I've, you know, when you
look at a problem for too long, you

can't see the forest for the trees.

Help me.

What is it?

Why am I missing here?

We jump in Figma.

You go, Ooh, have you thought about this?

Lemme just draw it real
quick . off the back of that,

you start unlocking thoughts.

It's oh, I haven't thought about that.

Ooh, off the back of
that, we could do this.

And then after half an hour to an hour,
there's this very messy Figma file in

which half of the things are not done.

Half of the things are in the
wrong place, things are duplicated.

And it's just the messiest
thing you have ever seen.

But by the end of it, you have something
better than you had in the beginning that

you've co-created with another person.

And a lot of other ideas that you can
now then go and explore on your own

because this other person came in and
with their creativity and thinking.

So sometimes outside of the box,
sometimes without having the full

context of what you're working on,
which I think can also be valuable,

has allowed you to unlock some more
of your own creativity and thoughts.

And it is the way that we've often
worked on different things together.

And I found that to be, and jamming is
something that I've done before, but with

you, it was very messy in a positive way.

Why did that work so well?

What?

What's up with jamming?

Tell me about jamming.

Josh: I love jamming So
much 'Cause it's so fun.

I think partially I
would do the same, right?

Like I would ping you and be like,
Hey man, like I'm deep in this.

I dunno what to do.

How do we just and I think partly
it's the burden of knowledge, right?

you can very easily get yourself into a
rabbit hole and start like going down it

and I think having someone there
to pull you out of that and

come with less knowledge, right?

Helps you to create your best ideas.

Because ultimately i'll start and I'll
start looking at like a bunch of screens

and how other people do it, how, and I'll
get and I'll go, oh, I like that one.

And I'll just gather all these things
and I'll start to point myself towards

a direction from maybe find out it's not
working and having someone come in with

a different perspective is working on
something completely different, helps

me as a bit of a palette cleanser as
well to abstract myself away from it and

understand that there's probably other
ways you can deal with this as well.

I think that's one route.

The second route is coming back to
that point of perfection, right?

It's like none of this perfection
is all like ideas and fun and trying

to drag yourself into this route of
what is something cool and fun I can

do with this piece of work as well?

And it doesn't mean you necessarily
have to do that, it's just a nice lens

to apply to it because it can give you
ideas that you may not have had before.

And then.

Ultimately there's this idea of
like pushing yourself beyond what

you think is the max you can do.

Right?

So sometimes I'll approach a
project and say, okay, but I

know I won't be able to do that.

So I'm gonna start like at this
point and like make sure this thing

is like shippable and buildable.

I'm not gonna have pushback from engineers
or pm but that's not the healthiest

place to come at with a project as well.

And so I think it's healthy to get
together, bash heads with another

designer and really challenge yourself
and like push yourself as well.

And so I think partly we're scrappy
'cause we're drawing boxes on a screen.

We would, we talked about like things
exploding and like characters doing stuff

and it being like a bit nuts, right?

And I think that's a fun angle
to take because it abstracts your

thinking and it drives you in a
different direction as well and helps

you builds something that is very
different to where you're at before.

But also potentially
scalable to that point.

Which is like something really
creative and fun and endearing as well.

Christian: Something else that was
different I've noticed about the way

you were working is if you look at
how most other projects start, there's

perhaps a PRD defined by product or
a problem someone has passed onto you

and at some point you take that into
Figma and then you start looking at what

others have done to solve that problem.

You go to Mobbin or you go to Dribble
or wherever you get your inspiration

from, and you see how others
have designed a say a list item.

Let's see.

How can a list item look like?

My assumption is that most
designers start like that.

Once they've done their research and
understood the problem, they want to see

how others have solved that same problem.

I think that makes sense, and I
think there's a space for things

that you're designing where you
probably should start like that.

If you're designing a settings page
again, to use that same example, do

you really need to revolutionize it
or should it just be a settings page?

So sometimes I think that's okay.

One of the things that I still remember
and I take it into my work today, is we

started a jam session and I presented
you the problem and you said, tell

me what brings you joy these days.

What products bring you joy these days?

And that took me by surprise.

what do you mean what brings me joy?

We're working on this screen.

How is what brings me joy relevant?

But I played along and I even remember
one of my answers was, uh, a Henry Hoover.

I bought one at that time and I
told you it brings me joy because

Hoovers are usually U as hell.

And then there's this smiley little
thing that everyone seems to love.

And you go on Hoover, your house, and you
look at it and it just makes you smile.

'cause it smiles at you
and it brings me joy.

And then we came up with a few
examples of what brings us joy.

We drew the principles of why those
products bring us joy, and then we started

designing from there rather than, what do
other products do to solve this problem?

And I found that to be a
different way of thinking.

In our fast-paced world where we're
being pushed more and more to be

functional and everything has to
be according to the design system.

And you can't do this complex
motion design piece because you'll

get pushed back from engineering,
or your product manager doesn't

think it's worth prioritizing.

So we always start from a very functional,
very stripped back context instead of

thinking, well, how can we design this,
that it brings people joy or how can we

design it that it's just the greatest?

Experience that we've created, and
it's okay to strip back a bit from

there, but the goal is to design the
best experience you can think of.

Josh: I remember that conversation,
and I just think that it comes

down to this like core thing we
were talking about earlier, right?

About like bringing a bit more fun into
work as well and trying to extend yourself

beyond, to your point, setting a sense.

List items.

List items, right?

Is this, there's gotta be something that
we can do to drive things forward and like

create these better experiences, right?

And better is better doesn't necessarily
mean like more, better metrics,

Better for us means it feels better.

It looks better.

It is nicer to use.

I think partially that comes from
building on each other's ideas . So

I think the other stance I take on
this is this idea that um, you and

I have experienced this, right?

You go in a room with someone and
they'll go um, why did you do this?

Why did you do that?

That's an unhealthy
approach to product, right?

Ultimately me understanding
your perspective, building on

that is a healthier route to
building great experiences.

And so the healthy route could be, tell
me something that makes you happy and

let's talk about why that makes you happy,
and like how we can like extensively use

that to build better experiences, right?

Christian: The last
thing I'll say, jamming.

That if you're now listening and
you're thinking, oh, I want to do

jamming at work, I wanna try this out.

Actually, I'll say two things.

First of all, I don't think it
needs to always be with a designer

because there might be someone who's
just the sole designer on the team.

I think you can easily jam
with a PM or with an engineer.

We all have access to Figma, and
again, it's not about designing, like

I said earlier, it was all messy stuff.

It's not about designing high fidelity.

It's about generating ideas and figuring
out how else could we solve the problem.

So I would say the first thing is don't
let yourself be stopped by the fact that

you maybe do not have another designer.

It's okay to jam with other people too.

The other thing I'll say is that what
I have found is that in order to be

a good jamer and to get the most out
of it, you need to have a low ego.

' cause the reality is that you're gonna
come in and we're gonna build upon

each other's ideas, but by default.

We're gonna ignore other ideas
so you might come up with an idea

and might say, well I like that,
but I don't like the other thing.

So we just take what I like.

Then you go and build upon mine
and I think you have to have a low

ego to go in thinking maybe nothing
that I come up with will be what

we end up with, and that is okay.

As long as we end up
with something better,

Josh: I couldn't agree more.

Can I add to that first part, which is I
would go as far as saying you should jam

with engineers, PMs, leadership, why not?

Ping someone and hop on a call with 'em.

Like I think I took a stance for
a long time that like I would

find like VPs really scary, right?

Ultimately they're just
another person, right?

Who's got really good opinions on
things, who's very clever and so like

leveraging other people's skills and
brain and opinions can only ever enhance

your work I think the best kind of
engineers and PMs are ones that hold you

accountable to a higher quality of design.

And the best way I found to like
pull that out of them is to just

like hop in a room and do something
that doesn't look great, right?

Because you're working really quickly
and then it, it helps them understand

your process, how you work, but also
gives them an opinion as well, and

gives them a voice in your design.

I think that's really important as well.

Christian: Yeah.

And off back of what we were
talking about earlier trying

to make other people feel heard.

It's very rare that a designer
reaches out to some, so a

non-designer and jams with them.

And that is one way of
making everyone feel heard.

It's like, oh, I co-designed this,
or I came up with an idea because we,

two weeks ago we jammed on the first
idea for this project that now, goes

to engineering or whatever it may be.

I think that is another way of making
people feel heard and being a bit

more influent in the business as well.

I don't think that we can avoid talking
about AI I also know that you are

using ai, first of all, you're using
AI in your day to day extensively, but

you're also working in AI right now.

You are at the intersection of it.

Let's split the two.

And first of all, talk a little
bit about practically, how have

you found AI in your day to day?

How are you using it?

Where do you think is really powerful?

Where are you not convinced yet?

And then after that we can
talk about working in ai.

Josh: True in the middle of it.

Throw myself directly
into the fire as well.

I use AI for a lot of things, right?

Like it is another jamming partner for me.

I'll use multiple tools, I'll transcript
with granola and I'll create a project

in Claude and I'll put transcripts
in and have conversations and use

it as someone to go back and forward
with right as well on these things.

This is something we
didn't talk about earlier.

That is like cret into my
mind as you going forward.

I think something that extends when
you get beyond the senior is the.

The flexibility to, I, I'm writing
PRDs in the teams I'm in, right?

And I'm out there just being like,
here was my understanding of this.

And for a while I pushed back
against that Ultimately actually

there's like a power in doing it.

'cause you own the specs
for the work that as well.

Right?

And you get everyone rallied and aligned
around it and you get it all written down.

I use it to write Ps I use it to
prototype, whether I jump in like

Figma make, or I'll start with
Claude Code or I go to Lovable and

I'll just build out prototypes that
I can send to people and say like,

Hey, gimme some feedback on this.

And actually it gives me such
a strong lens on analyzing

my own design work, right?

Being able to like,
use it quickly as well.

And build these things out.

I use it to make myself work quicker and
I work quick already, but like, this is

like another lens to work quick, right?

And so I'll give you an example I did
a couple of weeks ago working in the

space of like an LLM model, right?

And so, user puts in a query
model gives you a response back

it's layer, it's long, right?

It's structured, it's in markdown, get it
into Figma was taking me like some time

because I'd be like, okay, this is like a,
this is like a H one, it's like a H two.

The spacing here is this da, da, da.

da.

There's no like, structured
components like could just pull from,

because each time it's different.

So I went into, Claude Code, gave it
text stylings, spacing everything from

the ds and built a new Figma plugin.

I've never built a Figma plugin before.

I had no idea what I was doing.

So first of all, I was like.

How do I build a Figma plugin, right?

Then I got it to build a Figma
plugin and we iterated on that.

And now I have like a markdown plugin
where I can put in the markdown that

comes from the response, click insert
into my Figma and it'll structure it

based on the design system as well.

And so that has meant that like my
design works got quicker so I use

it all day, every day for everything.

Christian: There's that saying
that if you can imagine it, you can

create it or something like that.

And I think with AI that is perhaps
not entirely true, but it is

becoming a bit closer to reality.

What you've done there is you
have a problem that before

you just could not solve.

You didn't, you did not have the,
coding skills to be able to solve it.

And I think it's that curiosity
and willingness to figure

out now with these new tools.

Can this be done?

You just go and ask, can I
build a plugin that does this?

And it'll tell you Yes.

And half of the time it tells you yes.

It just tells you yes 'cause
he wants to please you.

But half of the time
it actually does work.

And I think it's just, I dunno where I've
read something just very recently, but I

don't recall where something like we go
around in our life accepting that a lot

of the things are just the way they are.

And a lot of the problems are
just problems that we can't solve.

'cause we don't have a
lot of control over them.

This is an example of how
you haven't accepted that.

You said, I have this problem and I
kind of wanna solve it and I'll try to

figure out with these new tools if I can
solve it and voila, you have solved it.

AI is nothing else than just a new tool
that you need to, it's a new hammer

that you need to learn how to wield.

Josh: Agree.

Christian: I do think there's a bit
of a mentality shift there as well,

because now you can do anything.

you can just do anything, right?

You can code anything.

You, even if you don't have the
skills, you can probably code

something very basic, very rough.

You have to change your mindset
from, this is just not possible.

I'm not gonna go, I'm not gonna go
through that door at all 'cause I

don't belong there to, maybe I'll
go through the door 'cause that will

allow me to enhance my own work.

So yeah, it's a mentality
shift, I think, now with Ai.

Josh: I couldn't agree more.

And I think again, this comes back to what
we were talking about earlier, about being

willing to step outside of the tools to
just do more I don't think design anymore

is about sitting and figma, designing
a screen and pushing it out, right?

If you can do more, have
fun, be creative, right?

I think there is an opportunity to
be more creative creativity without

limits I think is something new.

And I think that's
incredibly exciting, right?

I take the stance that I don't
think jobs are going away.

I think that there is these, this new
tool that it's more than like Aham, right?

Millionaire.

It's like the, this amazing thing
you can use to do lots and lots of

different things I couldn't do before.

If you asked me to write a document
before, it would take me ages, right?

Like, I'm not great at sitting
down and write a document.

It's quick now it's great, right?

And I can brain dump and talk the way
that my brain works and it can digest

it and spit something out that works
in a more corporate environment, right?

But it means like I don't have to put
on my corporate lizard skin, right?

And do the thing and then take it
off again and go back to design.

It just it enables me to do more,
be more productive and be more

creative as well at the same time.

Christian: I've heard the argument
of it allows you to do more.

I've also heard the argument of it
allows you to do just the amount you

were doing before, but go deeper.

So I think there's two
different axis here, right?

You can, you've saved um, the time that it
would have taken you to do the document.

Now you've done it in a few
seconds you can do more work.

Or you can say, well now this half
an hour that I've saved I'll spend

it, go, going deeper into the design.

So I think there is both, and again,
on what you were saying earlier,

there is no right or wrong way.

There is no playbook for this.

You just make it up and you do it however
it makes more sense to work for you.

But I, I have heard both and
I think they're both valid.

Josh: I love that

Christian: Let's talk about
what does it mean to work in ai.

And some of the complexities you deal
with and perhaps tell us so everyone

is aware the, of the context of what
exactly do you do at Microsoft now and

what does that mean on a daily basis.

How is it to be on the inside of
this massive beast and what are the

complexities you're dealing with there?

Josh: I'm still trying to
figure out what it means myself,

to be on the inside of it.

It's big.

It's complicated.

It's messy.

Right.

And I think that's like the point in which
like I work at my best, I think AI is

particularly interesting and I think it
depends what lens you apply to ai , right?

I think one of the challenges
we've got now is that AI is broadly

applied to everything, right?

Like I've got a coffee cup and I'm sure
if I buy the new model of my coffee cup,

it's probably an AI coffee cup, right?

We're talking specifically
about, like currently I'm at

Microsoft Health Microsoft AI
working in health I should say.

And so there's many lenses you can
apply to that And so broadly, I think

part of our team's remit is trying to
push and figure out what that means and

what we can do in an emergent space.

And I think that's really exciting.

So do you enable doctors
to triage patients better?

There was a paper that our team released
called like DXOA couple of months ago

that's had like huge waves, really
great like press behind it as well.

That's helped shape a path
forward for one direction, right?

Which is a way to like triage patient.

Using models, right?

And these are like, this is
an agnostic model platform.

So like which model is best
to triage patients, right?

And how do you do that effectively?

Then there's this like a
consumer lens to it, right?

So if you are like using copilot,
15% of queries that go into

that are health related queries.

How do you help

people?

and I think what's so interesting about
working in a model like that is that

it has its own reasoning skills, right?

So you go from what we've been talking
about earlier to like, cool, I am

creating a settings page with list view.

And there is this like very
structured flow that I can map out

to working with this thing that has
its own thinking behind it, right?

Its own process behind it.

Now there are some mechanisms
behind that, that you can send it.

Do you need it to think more?

Do you need it to like
structure in a certain way?

But ultimately the goal is to
give users the best answer.

And so.

stepping outside of design, again, there's
things that we're trying to put in place,

like safety tools, for example, right?

A lot of people come with
very personal problems.

And as you mentioned earlier, these
tools are like sycophantic right?

As well.

This is something that like a lot of
the bigger providers are trying to work

through . But they'll tell you what
you want to hear, and that's dangerous,

It's useful, but also really dangerous.

How do you work with this thing that
has its own reasoning skills to like

inject and create design around it?

And it's really challenged the way that
like, I think about design today because

ultimately, you have a few options.

One is you break the fourth
wall of the design, right?

You don't really wanna do that.

So if you are chatting And
something happens outside of

your chat, is that expected?

Is it.

Meant to be expected.

How do you build something into
a chat and work with the model to

reason that out and push that forward?

There's a lot of really interesting
challenges behind it, even down to

like new things it can do, right?

Like you can go to copilot and use
this thing called portraits now

where like you can chat to a face and
that's something that's built quick.

This is like new emerging
tech again, right?

And it's using a static image, but
like animating that image behind it

or turning things into 3D shapes.

Ultimately, I think as the companies
start to narrow down on the direction

of these products and broadly understand
like what's most useful for them and

intersect these points it will just
keep changing as you go forward.

And I think it's about like
adaptability in that space.

And I think it's really interesting and
fascinating to be in the middle of it

. Christian: It sounds to me like it's
not even in the classical sense, a

lot of design work, you're not always
sitting in Figma just drawing rectangles.

But it's a lot of decision making,
a lot of thinking through that.

A lot of even perhaps, considerations
of ethics you've mentioned, like

how do we make sure that it is
not always a good thing that it's

tells you what you want to hear.

So how does a designer
fit into that, right?

Like you're a visual person, you wanna
create things and suddenly you're

sitting in, in these meetings or in
these circles or whatever, async,

whatever they may be, where you have
to make these decisions that in the

past I think designers have not made.

So I think it more power to design
for being at the table, let's call it.

But how does that fit with, your
background in designing products?

Josh: I, yeah, it's a great question.

I think it comes back to what we
were talking about earlier, right?

This idea of rolling up your sleeves
and like stepping outside of like your

comfort zone being the tools you're in.

So, A really good example about
some work that like I can't

talk about publicly, right?

Is that.

And there's like several streams
to this work and one core, PM on

a stream of work who's really busy
on what is essentially like the

non-design aspects of that work, right?

There's a lot that goes into a model.

There's like policy changes,
there's legal requirements.

It's a whole ton.

When you work into this
scale, they're really busy.

And whereas when I started in big
tech, I'd sit there, I'd be like,

I'd get really frustrated 'cause I
wasn't getting what I wanted and I

wasn't getting the direction I needed.

I'll just go out and do it, right?

And I'll write the direction, I'll
carve the direction, I'll speak to

the people I think I need to speak
to, and broadly like start to narrow

in on alignment by surfacing things,
asking for people's feedback, right?

And moving forward, right?

And it comes back to that point about
like asking for forgiveness, right?

If I get six months into this
and I've shipped a bunch of

stuff and someone's whoa.

Sorry, I'm just getting into this.

Now.

Why have you done all this?

Then we can pair back and we could talk
about the data I've got, and then we can

always move away from that point, right?

And intersect away from there.

But actually we've progressed, we've
done work, and that means that,

you know, I'm part of this, I'm
like engineer managing, so I'm an

engineer on this piece of work, right?

As well.

I'm PM in policy advising.

I'm doing the stuff I, I have no idea
how to do, but I'm just giving it a go

because ultimately I like, I want to keep
moving this piece of work forward as well.

And I think that's probably
true more for this, right?

For AI in general when you're
working in a model because the

things you're gonna do need to ship
quickly, the competition is high.

And the way to do that is just by rolling
up the sleeves and like giving it a go.

Christian: Timely advice for anyone
working in design is just, competition

is fast and you gotta get things out
there rather than sitting around and

designing in Figma for six months, which,
it doesn't really improve anyone's life.

Josh, we got to almost at
the end, and we survived.

I do have two more questions that I
ask everyone at the end of the show

, The first one is, where do you look
for inspiration in your day to day?

Josh: It depends on the day . As you
know, I have a newborn downstairs.

I'm like six months old.

I'm not newborn anymore.

Have I slept that day?

Is it been a tough day?

Have I been commuting a lot?

What's happened over the weekend?

it sort of ebbs and flows, right?

I think I take a lot from
do you know Darren Brown is

Christian: Yeah, the magician, right?

Josh: love him.

He's brilliant, right?

And there was a show a many
years ago when I was sitting in

uni he took these different ad
agencies to pitch for an idea.

And what happened is each ad agency along
the way experienced the same things.

He'd stop them, something happened
in the car, blah, blah, blah.

And what happened is they all got in
and pitched the same idea because they

had the same experiences along the way.

So something I struggled with
uh, as you know before, right?

Like in my previous role I was remote.

I struggled to be creative
because I found myself not

getting out of the house, right?

I get my inspiration from getting
outside and seeing things.

That thing might be, Hey, there's a
new coffee shop in town that's really

nice, that looks really pretty and
they've got really nice branding

and maybe there's a furniture store.

I walk in and there's a piece of
furniture and it just sparks something

in me that gives me new type of energy.

Maybe I'm up in the fields 'cause
I haven't slept with my, not

just on my own, but the dog.

I don't just go up to the
fields when I haven't slept.

And I'm walking the dog in the
mornings and I'm speaking to someone

in the fields and they ask me a
question that sparks something.

But I think there is just like a bunch
of experiences I have outside of product

that gives me an energy to be creative,
that being in product all day doesn't

give me . And so I try and take myself
out of it and abstract it and see things

in person rather than trying to look
online 'cause I used to do a lot of that

and it, as we know, nothing's that great
at the, in the world at the moment.

So it's a bit of a rabbit hole you can
get into off the back of that as well.

Christian: Nice.

And then the second question, and last
one is, what is something that you don't

believe AI will be good at and therefore
designers could or should double down on?

Josh: It is not that I don't think ai,
it depends what good means cause I

think AI is good at a lot of things.

I don't think it's gonna be
perfect at a lot of things.

And I think that, and this is why I
think it's good as like a, a partner

assistant in some ways, right?

Because ultimately you have context.

You have context that
AI can't have, right?

Whether that's like social cues, right?

Whether that's like tone,
it's conversation, right?

It's like broadly like looking at a
canvas of things you're working on, right?

And understanding that, this thing's
happening here, this thing is

happening here, this thing's happening
here, this, and all it's got is

the context that you are giving it.

At some point maybe it'll have that
context, i'm not convinced it will.

I think that your job again is as well
as like shepherding product and people,

it's like shepherding this thing to help
you, give you the best work as well.

A lot of the documents that I work with
in like Claude, GPT, Copilot, whichever

one I'm working in give me really good
context, but it's never perfect, right?

Take some iteration off the back of it.

It just gives me a, canvas to start
working with, which helps me work

quicker . To not answer your question
and answer your question, right?

I think that it will be
good at a lot of things.

I don't think it'll be perfect
at a lot of things, right?

And I think that's your job, that is to
like, take control of that and steer the

tool to give you the answer you want.

Christian: I mean,

You did answer.

The answer is your job will be to
close the gap between the output

and what you put out in the world,

Josh: That's a beautiful
summary of a rambling answer.

Christian: Josh, where
can people find you?

Where can um, they get in touch with you?

All of that good stuff.

Josh: You can find me on
Instagram under @joshswatt.

You can find me on LinkedIn
under Josh Swattridge.

it's great to have a surname
that no one else has got.

Ping me, reach out to me always here to
answer questions, to jam, to do whatever.

Christian: Josh thank you and
if anything, this podcast, I was

thinking has been a lot of jamming.

It's like building upon
each other's ideas.

So there you go.

We kind of embody what
we do at work as well.

That's, uh, that's the, that's
the loop closed right there.

Josh, thank you so much for
being on Design This Business.

Appreciate you.

Josh: Thanks for having me.

Thank you.