Microsoft's Jamie Young on Storytelling and the Need for Designers to Evolve

Christian: Welcome to Design Meets
Business, a show where design leaders talk

about practical ways to quantify design,
about making our work more transparent,

and about how designers can make a bigger
impact in their organizationI'm your host,

Christian Vasile, and before we begin, I'd
like to thank you for tuning in today..

On the last episode of season two, one of
my favorite conversations with Jamie Young

principal design manager of Microsoft.

We're talking about the need
for designers to evolve.

We're talking about why storytelling is
an important skill to have, and we're

talking a bit about being an individual
contributor and staying an individual

contributor versus moving into management.

We are ending season two on a high
and I hope you liked this episode.

Just as much as I do.

Jamie welcome to Design Meets
Business you have got 20 years

or so in the design world.

And during that time you've been
an interaction designer, visual

designer, mobile web designer,
graphic designer, brand designer.

And that's probably not all of it.

So on top of that, you've worked at
early stage startups agencies, and now

we're tied to any company like Microsoft.

So it would be interesting to hear a bit
about that journey and a bit about why

you've been in so many different roles.

And what's exciting about

Jamie: exploring different roles.

Of course.

Thank you, Kristin.

thanks for bringing me into
this and asking me to talk

about some of these things

To introduce myself briefly, I'm
currently a design manager on ML

or Azure ML for Microsoft, but
I've also spent time in Microsoft

running the developer tools team.

And before that, and worked in a
software company called canonical,

which made a, an open source
operating system called open to which

probably people have heard of you.

And as you described kind of the run-up
to, that has been at a whole mishmash of

different things from marketing, websites
through to mobile apps and way back in the

midst of time 20 years ago, or so I was,
I kind of, you know, branded communication

and campaign designer as well.

Um, and I think, yeah, I think that's,
it's, it's, it's an interesting,

Christian: it's an interesting

Jamie: one is in the front door.

So, uh, it has been an
interesting journey.

I think we can leave them
to be at the front door.

Um, it's been a, yeah, it's been
a really interesting journey.

And I think that.

One of the things that has, does, I
guess connect, I suppose, all of the

experiences that I have, is a strong
belief that I have that kind of like

design principles and design values
that are arguably, consistently useful

through, out all of those kind of form
factors in which we design within.

The importance of, and the value
of design, um, was important

when I was a brand designer.

it's important to in your mobile,
I think good design is good design.

And although I work in what this, what
I sort of sometimes pinch myself as a

very slightly weird, very technical area
of design right now, you know, working

on kind of machine learning tools for
Microsoft the importance of good design

and good user experience is still, yeah.

Top of everything that we do.

And that the thing that I think about
it and think I talk about all the time,

the user is still the user and they
still need a good user experience.


Christian: How have you seen
design change over these years?

I assume the value of design was no
different 20 years ago than it is now, at

least two different how, at least how to
help businesses, we're thinking about it.


Jamie: I think that's it.

I guess the, you know, 20 years ago
to now the, my involvement in those

conversations about the value of
design was very different as well.

When you were a kind of, you know,
uh, a graphic and a brand designer,

um, it was it's, it's weird.

It was almost when the clients I worked
for back then, it was almost a given.

Th that you needed a designer to do
some of the work that you did like, and

that's, what's quite interesting actually.

You know, when I, when I started
working, I worked in things like express.

I worked on print, I worked, you know,
I did really, really kind of arcane

things that a lot of your listeners may
never even heard of, hopefully somehow.

and, but the portions of design or rather
the importance of the involvement of

designers was unquestioned in some ways
in as much as like you needed a designer

to deliver on a, on a brochure or a book
or a piece of brand work was kind of a

piece of communication, a campaign that
was a sort of an essential component

of doing any of those bits of work.

I think what's really interesting.

Now as we evolve the design discipline.

And I, you know, I was having
conversations with designers in

my team just this week about like
the kind of idea of a full stack

designer or a generalist designer.

And I think we'll get into
that a little bit, cause that's

a really interesting topic.

The essential need of
the design capability.

As a kind of discipline
is, is, gets blurrier.

these days in software design, because of,
and because of tooling, I think because

of like the, there are, um, what's the
word for it, our access to the tools now,

whereas before it was incredibly expensive
and you needed a lot of training to do

a lot of the work, you know, these days,
arguably that's not the case anymore.

And what's interesting with
it, you know, we, yeah.

So it's interesting.

I think that's the big change,
which is, I don't know.

Some people might see as a fearful thing.

Some people might see as a worrisome
kind of like, well, we've got

cheap access to design tools.

Therefore everybody's a designer
does it democratize design?

I think it challenges that
design, uh, discipline to.

Look hard at themselves and figure
out what it is that makes design

important component in the process.

Again, I think that's an interesting time.

Christian: Yeah.

So you said a bit earlier in
the beginning, it was very

much around delivery, right?

The value of design was, was you
had to deliver a poster or whatever

it was, but in the present, it's
not so much about delivery anymore.

Eh, It's much more about how can you as
a designer provide any business value

or how can you help the business grow?

Because the way I see it then, and
very much to the point that you've

made is tooling is not as complex
as it used to be in the past.

Access and tutorials are
free on the internet.

Anyone can really anyone with enough
time on their hands, anyone can design

a wireframe where anyone can put
together a flow in Figma today, or

in sketch, whatever people are using,
however, the skills that are necessary.

And if anything really valued, have
changed over time from delivery to

more strategic, if you will, would
you say that's accurate, you know?

Jamie: Yeah.

Honestly, that taps right into
what I, I'm pretty passionate about

talking with people I work with kind
of day to day about and have done

over kind of my time at Microsoft.

And I think it was Almost certainly the
realization when I started managing a

team and having to figure out how to make
a team of 30 people that were suddenly

looking to me for kind of guidance and
strategy, how do you make them, how

do you make them have the most impact
of that you can with a team that size.

And it's when I really started to dig
into just what you described, Christian,

where honestly speaking, when your design
team of 30, back in the day, science

quite big when you're sitting inside
Microsoft and your closest partner is

PM who are probably in the hundreds
and then engineering or almost in the

thousands, you need to start to really
think about like, okay, how do I make

impact and how do I bring value out
of every single one of those people?

And We talked about this thing when
you're in dev tools, the idea of

shifting left the idea of, tackling
problems that may become kind of

bigger gnarlier things later on in
the process tackling them earlier.

And I started to think about
design in that kind of capacity.

So I started to really think
about, okay, if we have 30 people

really making everybody a Uses
Figma and turns out screens is

not a good use of everyone's time.

And so how do we in fact engage design
as a discipline much earlier in the

problem-solving in the concept creation
in the strategic thinking in the process

to have ultimately more impact it's
that early point that you can engage.

Um, and it's what I've been pushing where
I am right now for the last kind of 18

months in Azure ML as well, and trying
to get the team thinking that, and, you

know, I think the other thing that I have
experienced and been quite interesting

in my time, kind of working in two teams
now in, in Microsoft and spending most

of my time in developer tools, where we
actually had that arguably centralized

design organization and challenged by.

The fact that on the whole, how getting
that early involvement was a kind of, you

know, it was something that we had to push
for and ask for and try and drive towards.

More recently I've spent the
last we've had about six can't.

Remember how many months exactly was five
or six months ago where I am in Azure ML.

We actually did a mini reorg and we work
as, as much more cross-functional group.

And I've noticed one of the, one of the
interesting things my goal of always

pushing designer in the process, because
I think it has a bigger impact earlier

has been much easier to do when you
have a set of cross-functional squads

of design, where a designer is matched
to the PM, match with an engineer,

matching the researcher, because
everybody's just, it's one team and

everyone understands the value of that.

And so, that's been, I think.

Whereas I've been on this journey
to try and make design impactful and

arguably push it earlier in the process.

I think one of the realizations I've
come to recently is like the organ,

like the, the ship, like the way that
we also work with partner functions

is incredibly important to how
effective you can be in that place.

Christian: For sure.


Did you find that having these
smaller teams, smaller squads allows

design to get involved earlier?

Jamie: Yes.

I'm going to say yes.

What has been interesting, you can
set up the groundwork for, for that

to be effective, but, um, I think
there's also an aspect of like

culture where you need to really have.

The designers who are often, you
know, in these enormous organizations.

And I have only experience of Microsoft
at that scale, but even up until

we were a centralized design organ,
actually, arguably were challenged

by some of the kind of aspect of not
necessarily having as much impact

early as we would've liked to.

We weren't design wasn't a
function that was kind of involved

earlier in the process, of the
product or doing to either.

I think it is up to you much more now,
but certainly my time, it wasn't then

you could set up the kind of groundwork
for success and for involvement early,

but you also need to often guide a
set of designers or design group into.

Feeling comfortable in that space as well.

And so I would actually say, I can say
this openly they would agree with me

themselves, the designers on my team.

It took a while to climatize, to
the fact that like, they suddenly

had the ability to impact and to
be part of that early process, much

more than they had in the past.

And it was a bit of a, oh, okay.

I can do this now.

So the moment which was really exciting.

It was exciting for me to see that,
we're working on it right now.

It will get better and better
as we get better and better.

Christian: Yeah, that's interesting.

I've never thought about it that
way, because everyone talks about,

we want the seat at the table.

We want to make a difference.

We want to get involved earlier,
but when you get that, how does

that change your, your daily life?

It as in your job, right?

It changes your job almost completely
because suddenly, suddenly what's

more important for you as a designer
to do is to get involved earlier.

You, you need to do
more strategic thinking.

You need to be in those early
conversations with other business

stakeholders versus I just need
to deliver some, some design work.

So it's kind of like careful what you ask
for, because you might just get it yeah.

Jamie: A hundred percent,
a hundred percent.

And like, I know the designers in my
group are a hundred percent capable of

doing that delivery, understanding that
strategic partnering with the PMs and

engineers that we work with on that.

And actually having a unique
perspective that the other groups

don't have on the experience.

They come from a kind of user kind of
focused kind of angle that always will.

I think it's really interesting.

Like you're totally right.

And I think that's some of the, kind
of like the shifting and adjustment

that has taken needed to be a
bit of a mindset shift as well.

And as much as it's been, what's also
been interesting when I, even, when I

worked within the bigger Oregon developer
tools with, with kind of much, much

more people the program management and
engineering by and large have always

been open to design's involvement.

It's just been a capacity of
like, how do we get to there?

How do we get early?

And I think one of the kind of changes
I re like I really understood this

year is like, actually, you really
need to think about how the teams are

structured to allow for that to happen.

Um, and so the partners we have
in PM and engineering are like

more than happy to have designs
involvement at that early stage.

We don't feel any
resistance in that capacity.

And that's great.

Like, that's super great.

And I don't know if it's part.

My working with the leadership in those
things as well as it is just the designers

that we have on the team are very, you
know, like they're highly capable of

stepping into those strategic places
too, but it's a, you know, kind of

pivoting into this, but it's interesting
because it sort of touches a little

bit on the conversation that was had
again, having this week, we wanted to

designers about the idea of sort of,
and this is kind of probably quite a

familiar term for maybe some people
like the idea of the kind of full-stack

designer and is that important and, uh,
a company as large as Microsoft we have

people that are happy to not do that.

Strategic thinking, you know, people that
are kind of happy to be kind of designers

almost in the truest sense of the word
where, where the craft is, the thing that

defines them as a designer and that's it.

But I do see in large parts of
our company, certainly that the

need for that evolvement or that
the need for that to evolve into

more of this kind of like business
focused business thinking designer.

And certainly we have design
leaders at the very highest level

who are driving that and push that.

And, you know, Jonah's starting VP
diff design in Microsoft is one that

definitely Springs to mind as somebody
that's very passionate about the idea

that design is a business function and
should be involved at these early stages.

but it, as you kind of touched on earlier,
Christian, it pushes us to think about

what the designers core functions are.

and one of the things that I
have noticed recently, this is

part of that conversation is the.

The importance of research
and research being a kind of

skill that designers can wield.

Um, because often again, we complain
and worry about design being a

small discipline within a huge
software organization research,

or even smaller, like, you know,
they're half the size of design.

And so like they're even more challenged
by some of the things that we talk

about and , the levels of kind of
ratio and of what they can get to.

So I, something I've definitely noticed a
trend of and it's maybe not that uncommon,

but it's certainly something that's kind
of happening in Microsoft at the moment is

the desire slash neat for designers to be
able to wield some research skills, to be

able to, I think, to be able to qualify a
lot of the design decisions that we make.

we're incredibly, data-driven credibly
research driven to do more of that.

We need more people doing those
things, if that makes sense.

Um, so.

Christian: So I think we should go
back to talking about full-stack

designers and all that, but just before
I, I have a question too, regarding

something that you said earlier, you
said they might be required a slight

organizational change in order to allow
design to get involved a bit earlier.

So my question to that is, is there
for therefore, do you think it's

not possible for that change to
be driven from the design sides?

Does it have to be first some sort of an
organization change there in order for

design to be able to get involved earlier?

Jamie: It's an excellent question.

I have, I have an opinion on it and
this is just my opinion, but like I

would say that, I think now there's kind
of two parts of my answer, I suppose.

I think, yes.

I think that to see designs impact
earlier in the product making

process, we probably need to have.

We have need to think about where
we're designed sets and, and

who it works with most closely.

and I think that, you know, there's
lots of different ways of organizing

design teams and there's this kind
of like, you shouldn't organize them

depending on the business need and
things like that, but they're kind of,

you know, broad, the broad shapes are
kind of embedded or more centralized.

And having been part of both, I'm
seeing much more effective, early design

participation in a, in an embedded team.

And that said I think that there is
definitely, there's definitely ways of

making a centralized design team, but I
think much more like a more impactful or

involved earlier in the product process.

Um, it probably requires a lot
more advocacy on the part of the

design leader and maybe just.

Any design leaders that work
underneath them, and also a great

relationship with PM and engineering
to understand why that's important.

if you embed everything the value is
immediately apparent because you can

see the squats working together as one
they're responsible for the same things.

They're accountable for the same things.

They're engaged in the same process
that trying to, they're trying

to work towards the same goals.

If you do it as a centralized.

You have to proxy for some fat, you
have to make sure that everybody's

aware there's an alignment aspect
where you're always reminding people.

This is why it's important that
designers involved does this.

And this is why it's important.

This is why it's important.

This is just my experience, but certainly
that's the sort of the shift I've seen.

Christian: Yeah.

We've, I mean, we've had quite a few
heads of designs and design directors

on the podcast and every single
one of them says the same thing.

So something along the lines of the work
that I do is I don't push any pixels.

Obviously I don't do that anymore.

But the work that I do is, is the
work that's required to allow the

designers on the ground so to speak,
to do the work that they're here to

do, there has to be someone at the top
to frame design, to advocate for it,

evangelize if it's necessary and the
older the organization in the more.

The less design driven it is the more you
need someone at the top to kind of pick,

pick that battles and fight them really.

Jamie: Yeah.




Just, you know to make sure that design
is represented at all of the touch points

or the moments that the organization
comes together to make sure that

people remember, you know, like the,
remember the importance of design as a

discipline as part of what we're doing.

Um, no, I totally agree.

And it's been interesting, I think, and
this is maybe somewhat of a function of

my remote aspect of it because the whole
time I've worked at Microsoft, I've been

five-year years worked from east London.

And my team has always, almost
always been based in and around

Seattle with the leadership kind of
based in and around Seattle as well.

So again, when you talk about a
design leader needing to have, uh,

needing to pick those battles and
reminders, so then advocate for

design at the kind of highest level.

When I'm working eight hours
separately, that's always a challenge.

Like that's always a challenge to do when
you're having to sync with those other,

oh, the other leaders in the organization.

Whereas I can see how quickly
we're getting to that point

already with an embedded model.

And it doesn't require so much
of me having to do the advocacy.

And so much of that kind of, I have a
group of people I work with very closely.

They understand that the team understands
that and we're sort of often going,

Christian: yeah, that makes total sense.

Let's go back to full stack,
but let me first ask you this.

If I go on your website, the only
thing you see, I thought that was so

funny when I was doing my, my research
says, like go into a website, the only

thing you see is a Swiss army knife.

And I thought, I think I know what
that means, but I'm going to ask him,

so tell me about this Swiss army.

Jamie: Well, no, you know what,
so it's w so the Swiss army knife.

It's interesting.

I think so when I put the Swiss army
knife in, there has a sort of, you know,

cause I think when you're a younger
designer, there's always, everyone's

always doing their own logos and
they're doing their own, this and that.

And they're trying, they're trying
to kind of set their personal brand.

And I think before personal brands
were even a fun and cool thing

to have and an important thing to
have, they're not just finding cool.

I think, you know, designers were trying
to define themselves through, and always

show off some of the craft or, or even
talk about some of the way that they

designed and, and the Swiss army knife.

One of those things where I was trying
to think of a way that I could, Sort

of visually depict my impression of my
background and your right, essentially.

That was my longest.

And I actually, oh, I
don't know where it is now.

I have a small five-year-old son now.

And so leaving Swiss army knives
around the house and stuff, it's

just something that's not really
done, but somewhere I have it.

And you can in fact, get you a
Swiss army knife personalized.

So there was no Photoshop involved.

That was literally, I got, that's why
this type of graphy is a little shonky

because it was done by the company
that directs that, that make it.

But yeah, I got a Swiss army knife with
my name printed on it, as a, as you

say, as a way of depicting the iHub
at that point up until that point.

Anyway, I had a variety of,
of different backgrounds and

different things that I'd done.

and arguably, that has only
proliferated since then.

And so I guess the Swiss army
knife is still kind of applicable.


I, the interesting thing about that when
we talked a bit talking about generalists

and full-stack designers as well, I was
super nervous about using that as a.

Representation of myself.

There was definitely a time when I made
that image and I use that to represent

myself that like being a generalist,
actually, wasn't a good thing.

You kind of want it to be a UI designer or
you wanted to be a UX designer or you want

it to be a typography for graph brand.

Like we had those, the industry at that
point was like, being a specialist or

someone super good at one particular
area, it was actually more benefit,

like was, was judged to be better.

I think that in a funny way
has flipped on its head.

And I think the idea of this kind of
generalist or this full stack designer is,

is been around for a while and is only,
only becoming more important, I think.

And, and just for the reasons we talked
about earlier, the tools are cheap.

Anybody can pick up Figma.

you can watch a bunch of
videos about how to use it.

the skills that we now need to learn and
to understand are much, much different.

So yeah, this be nice.

This is the depiction of me
as a generalist back then.

Christian: I don't anything's exchanged.

No, that's good.

It's probably has evolved.

As you said, you've added
another tool to the,

Jamie: I need, I need to, I think I
only had something like six or seven

of those different things, poking out
this just how mean I need the bigger

one now the one with all the bits.

So that'd be my update.

Keep an eye on that, that
your logo is coming soon.

So it's,

Christian: it's interesting you said in
the past it was very important to have

one skill to be really good at that.

I think it also comes down to what the
organization you're working as part of

needs, because I can think off the top
of my head of a lot of startups that

I've worked with, that didn't really
have the budget for a, an individual.

Or UI designer, strategist and all that.

They just needed one
person who could do it all.

And I also can think of quite a few
large companies that had the budgets

and have the organization structure to
support all of these different roles

that could be done by one person, but
they would prefer to have them separate.

So it's a, I think it also comes down
to the organization you're working as

part of, I am a big, big, big fan of
generally sell I'll openly admit I am one.

but with that being said, I think
it's really important to have one

thing that you're really good at.

So you're kind of like a T-shaped,
you're a generalist, but it's

more of a T-shaped generalist if

Jamie: you will.

Yeah, I think probably everybody
is even if they don't quite realize

what that T bit is, but normally
it comes from the background that

has gotten them to where they are.

Like, as you say, I think that.

We've we joke quite a lot.

We have a lot of very talented
interaction and technical interaction

designers on my team at the moment.

And we joke quite a lot that I'm doing
a visual designer because I'm the one

with the visual design background.

And I make, and spend quite a lot of
time helping the team with kind of,

the direction around design systems or
I cannot graphy or color or, you know,

type of wifi and things like that.

And so, that's yeah.

I say, as you say, we're all probably
T-shaped and sometimes it's good to

sort of sit back and figure out what
your kind of where your depth is, but,

our top of our tee is getting wider.

I think maybe the kind of like,
I dunno, that's probably the,

Christian: the Vista the vertical line.



We're supposed to know these are,

Jamie: but back in the day, I
probably wouldn't have done, but yeah.

It's not ever, it is apologies to
any time photographers listening

yet definitely should know that.

But yeah, the vertigo is
probably getting shallower.

I think that's the thing that I'm
certainly seeing anyway, in the

experience I've had at the moment,

Christian: It's not only technical
skills, it's getting wider than that.

Like the top, the horizontal line
is getting wider because now.

Unlike I'll agree.

10 years ago, soft skills are becoming
really important for a designer that

wants to work at that intersection
of design and business wants to be

part of those conversations a bit
earlier on needs to build trust with

the rest of your organization needs
to understand how to frame design and

talk about design from the perspective
of whoever you're presenting to.

So all of these are soft skills.

They're not technical skills.

You really learn by sitting
down and watching a tutorial.

It's more through experience.

So we'll talk about soft skills a bit
later, as part of the, you know, the,

the, the end of podcast question, but
what do you think that, that is becoming

more and more important in terms of

Jamie: soft skills?

Yeah, no, that's so, as you say,
like, I ha you know, soft skills.

Everything you need, if you
want to be at that intersect.

Because if you think about, if you
think about it, like, the, the sort of

activities that you're doing at this
early stage are in practice and hopefully

not all the time, but in practice.

And hopefully there are much more of
these kinds of collaborative, white

boarding activities that prioritization
activities there, they're not productive

activities that necessarily need you
to have a graphic design or any kind

of creative background whatsoever.

Everyone could pick up a pen and
draw on a whiteboard and put up

post-it notes and things like that.

And again, that comes back to that sort
of like, how do we define what it is that

makes design design or makes interaction,
design, design, and again, you know,

in a way, this is a little bit back
to what I was talking about earlier,

where the sometimes designers need a
bit of time to claim the ties to this

new way of working, and then the kind
of things that they're being expected.

Bring to a meeting or, or kind
of a conversation or a workshop.

and you're right.

Like soft skills are
super like invaluable.

Um, and in a lot of times, because
actually I think I'm okay to say

this, but not everybody is blessed
with a skill in soft skills.

Particularly if the discipline
they're working in doesn't

necessarily need, require them
to have soft skills, you know?

And, and so like being, uh, a great
facilitator or a great Collaborator

a brilliant user I'd like advocate
for the user or the customer.

We talk about a lot insight,
Microsoft is enormously important.

It's a huge thing of how I
believe design again, can be

impactful early in the process.

How design becomes important to business.

I think the one thing I.

Really learned through my time
so far Microsoft is, is just

framing how we talk about it.

This is not like rocket science.

You know, it's not rocket science,
but I came into Microsoft,

not fully understanding this
as well as I now understand it.

And, and in part that's because I
was very quickly having conversations

with engineering leaders and PM, PM
leaders about why it's important.

And I saw how they talked about
the importance of their work.

And we talked about this inside Microsoft
a lot, but I think it's very common.

It's like most large organizations
and it's just the idea of

impact, the idea of impact.

It's just it's in some ways
to describe it, very simple.

It's like you have, you do
things, but why do you do things?

We talk about activities and impacts.

So you do things, every day,
every week you've done something.

It is sadly rare.

that we regularly sit and talk and
think, and sort of analyze ourselves

about why we're doing those things.

It's not always rare and it depends on
kind of like the seniority of designer you

are or the type of designer you are, we
will avoid a lot of trade secrets here.

We will often come round to kind
of like these review processes

we have with insight Microsoft.

And we're asked to describe the impact
that we had over a given period.

And that is hard P designers,
every, almost every single person

I've worked with on those sorts of
appraisal processes, really struggled.

And in fact, I've worked with
managers and in teams to try and

clarify how design can talk about
impact or how design can take impact.

And I have a kind of like, I have an
opinion, which I know is not, um, not the

same as some of the people I worked with,
but, um, I'm happy to go there anyway.

and I think this is it's interesting.

I think this is more true
in my more recent team.

I, I actually believe to an extent
and just to be clear it's very

easy to talk about impact when you
were saying I moved to metric eight

to, from zero to 20 or something.

And we by NPS score from zero
to 40, over a given period.

And I see our partner disciplines in,
in PM and engineering able to very

easily talk and look at, but point out
rather tangible statistics or metrics

that they have shifted the needle on.

And, and that can be great.

That can, that's a very easy
way of understanding the impact

of the work that they did.

Design I think has a harder
job because it often is.

Involved in some of the things that are
talked about at the end sort of later on

down the line or they've been involved
early, but like, how do you quantify what

the impact of that, of the design of being
in that initial kind of workshop was?

And so we tend to look at the sort of
the end game, almost what did we deliver?

You know, what do we deliver from a kind
of like output and assets and red lines?

And I've seen so many kind of those
conversations where someone's kind of

like, I deliver this, this, this, this,
this isn't a huge bullet pointed list.

And I was like, well,
why, and is this a blank?

look how like, uh, okay, so we
need to kind of unpick it all.

And I spend a lot of time talking
with designers about how we pick

that and try and get to the nugget
of like why the work that they did.

And it's always there.

Do you know what I mean?

It's like the five why's it's like,
you just keep asking until we get

to this nugget of like, why it's
important, but the thing that.

I know that I'm, you know, I'm not
maybe alone, but certainly I'm not

always in agreement with people I work
with about is that I do, I do believe

that design and I believe there's more
and more now, the way that my team is

organized as embedded teams with squads,
I believe that the impact of the work

that they collaboratively do should be
attributed to the designers as well.

Like I believe that like design should
be able to say, you know, our NPS

score went from zero to 40 again.

we can draw a line to the work that we did
around NPS where something or usability,

that was an NPS theme, to saying that
actually we can say we contributed

towards that, that, that metric.

but it's hard, I would say, like,
it's hard to find those hard things

that people feel good about saying.

Yes, eight to be that thing and
draw a line back to some design

work or some design involvement.

Maybe even the same for research.

I'm not sure maybe, or maybe not.

I don't know.

That's an interesting

Christian: one.

Well, the way I think about it is
in any other industry, if you want

to talk about impact, you would
count the impact of the entire team.

So this goes both ways.

It's, it's it's whatever the PMs
and the engineered team is talking

about in terms of improvements.

Design has likely had an impact on
that, but the other way around as well,

because I sometimes talk to designers
and ask, well, what's the impact here?

Okay, well, we've moved
metric a to metric B who's.

We are, well, we, the
design team who else?

Cause you can't ship products.

You just you're a designer.

So surely the is the testers is the
analytics team is everyone else.

And analogy is if you build a, uh, who
gets credit, just the brick layers.

It's the architect, it's the brick layer.

It's the carpenters is everyone else.

And similarly I find because
design is a team sport and that's

why I think it's interesting.

Sometimes I have conversations.

Well, who's more important in a
productive, there's no such thing.

There is no such thing.

Everyone is a piece of the puzzle.

And without the piece of the puzzle,
regardless of which piece of the

puzzle, that is not a complete
puzzle, that doesn't make sense.


So I also think it should go the other way
where designers should give more credit

to the remain, to the rest of their teams.

And I'm wondering how are you empowering
your teams on a daily basis to talk

about design too, whichever stakeholders
they need to talk about design to it

from the perspective of, of impact
from the perspective of here's what

this team has achieved over this
period of time, how are you doing?


Jamie: do we know?

So well, it's, I mean,
so it's interesting.

I like, again, this comes back
to this idea of like, how do

you shape the team as well?

It's much easier to say this team achieved
this and this team have these different

pieces of a puzzle that achieved this.

And without that piece of puzzle,
obviously the puzzle isn't clear as much

as you do that, when you have distinct
squads and like, but your question was

how do we kind of empower design or,
or talk about it on a regular basis?

One of the things that we set out
to do, um, this is another example.

So one of the things that we
set out to do when we were.

We w when we set up this kind of
squad model, which we're doing

now was that, we have regular
check-ins for the entire team.

So there's a couple of things, actually.

Um, we do a regular check-in every
month for the entire team, and everyone

brings together and we walk through
experiences that the cross-functional

teams have worked on together.

And a lot of time it can be a
designer and a PM presenting it,

but the engineer will also be there.

Like, it is very much
like a, a group effort.

So whenever we're sharing, it's not
designed, did this thing, or PM did this

thing, or engineer built this thing.

It's like, everybody feels like it's
a, I hope everyone feels anyway , that

it's something that they all worked on.

And they're all seeing
the benefits of that.

The other thing that I really enjoy.

At the moment is we do a
weekly what we call UX review.

It's not a sort of a particularly snazzy
name or particularly kind of like clever

format, there's a need sometimes to do
some form of kind of UX gate, um, for

experiences coming through that, the
work that we're doing and what I've been

really in the past when I've done those
as a centralized designer work, what

what has happened is we've had without a
bunch of incredibly talented, very senior

designers and one or two PMs kind of
walking into this environment and showing

their work and often with the engineers.

And sometimes those
conversations are great.

And sometimes the
conversations are quite spiky.


It wasn't until kind of close to my
end at my time at dev tools that I

heard some lateral feedback, that those
are quite scary things to step into.

This is a bunch of my colleagues and
people I knew well and friends of mine.

And I certainly thought, and I was always
very careful to try and be as inclusive

and low stress, although there's a
kind of function of those forums where

it was a kind of go, no go aspect.

If it really wasn't up to snuff,
we needed to ask them to come

back and do some work on it.

Um, but I heard laterally that those are
quite there were, they had, they have

been quite kind of imposing intimidating
forums to step into as a PM or engineer.

The thing that we're doing now is, uh,
is like from the get-go a completely

cross-functional conversation.

And so like every UX review that we have
every week, We'll have the experiences

that the PM engineer designers will bring
in, but it's like the room is full of like

engineers asking questions about the user.

We've got PMs asking technical questions.

We've got designers ask and it's
a really much more, um, Lively

vibrant conversation, I think.

I think there are less intimidating and
maybe find out later, I don't know, after,

Christian: after they
listen to this, they'll

Jamie: tell me exactly what

Christian: all you on about

Jamie: this.

I'm expecting a lot of that.

Hopefully all positive.


Christian: totally.

We were talking earlier about soft
skills and I like to use that as a

segue, into talking about hiring and
portfolio reviews and all of that

from the perspective of a manager.

And what do you see a lot
of designers do wrong?

What do you see a lot
of designers do, right.

And all of that, but let's, let's
use the soft skills, a breach.

How do you, cause it's easy to
look at a portfolio and say,

this person has a technical.

But he's much harder to look at a
portfolio and say, this person is a

great communicator, or this person knows
how to frame design for stakeholders.

It's so hard.

So how do you even find out
about that before you hire

Jamie: someone?

Well, that's interesting cause
that last bit of the question

is the really tricky bit.

so yeah, so I think I mentioned this
before we're hiring or have been

hiring a lot of people at the moment.

I've been doing a lot of these sort
of thinking and conversations at the

moment and I've kind of, you know, the,
I guess , it comes back to a little bit

about what we were talking about earlier.

Like the, what I see now in the
sort of skill sets of folks coming

through and looking to join our
team is By-in-large kind of like

the same set skills everybody has.

Everybody kind of understands
that they have to do a bit

of research on sound stands.

They have to talk to the users.

Everyone understands that they have to
do where our friends don't understand

that they have to have feedback.

And the challenge then is because it
becomes, it becomes a bit noise and I'll

be, I'm going to be frat very Frank.

It becomes a little bit noise.

And so, you know, we've just listed me
today, finished hiring for four roles.

So that means I probably have talked
to 40, so plus people and I've looked

through just now countless CVS and
portfolios and online things as well.

So, um, what I think sets folks
apart, and it's just what you were

alluding to is the F you know, is
the storytelling aspect, like what.

That they can bring to this thing
that they're sharing with us.

And that doesn't have to be
something that had millions of users.

It doesn't have to be something that
they could, you know, had a whole

research team working on before they
worked with the whole research team

and they did all this validation.

There's almost always something like
unique to the way either the way that

they approached it or the project itself,
because humans are inherently interesting

and different and fickle and weird things.

And that's, what's great
about being a UX designer.

We get to work most of the time with
human beings who are very difficult

people, things and drawing that
out of their work is the things

that have always set folks up.

And then the ones that I'm like, okay,
actually those are the people that I

really want to bring in for an interview.

And even then sometimes that doesn't
work sometimes even then sometimes you

think you've got a great storyteller
and it transpires that, that isn't

quite the case, sadly, in the moment.

And I think it is, it is, again, it
comes back a little bit to the why a

little bit, it's sort of like when the,
when you're sitting down and you're

thinking of like, from the perspective
of the people applying, like when you're

sitting down and thinking about like
how you want to set yourself apart,

via online, be it in the conversation
we have as an informational screen,

be it in the interview itself you are
uniquely different to the next person

that hiring manager will talk to.

Um, what is it that you can help them
with you buy and, you know, I think that

we have, we've had so many portfolio
presentations that I've asked the team

to sit through and they've given me great
feedback, there are a couple probably

that were just brilliant storytelling
and just stuck in the mind of everybody.

Um, and it's, I think that you talked
a little bit about like how when

you're looking for people, again,
this comes back to this soft skill

idea, and it comes back to like how
design continues to be an important

function in software as the tools
that kind of like as all democratized

and the skills are all democratized.

How does design or interaction design
or UX design, whatever you want to

call it, become unimportant function.

It will, I believe it will become through
the skills that folks bring through

things like, as you say, storytelling
and like advocacy for, and so when you

see those people start to pop up on
portfolio reviews, you're like, okay,

those are the ones that want to try and
get on the team because I think they are,

they're not, I think everybody can be
taught these skills, like to be clear,

like, I think you can learn this stuff,
it's practice and things like that.

Some people come in to these
things inherently easier.

They just feel more comfortable in those
environments and doing that kind of work.

I enjoy that kind of work.

I think that's why I
like being a designer.

I like telling stories.


Christian: Well, would you say that
storytelling and all those soft skills

is something that shines through
face-to-face or in an interview,

but in order to get the interview.

It's probably still the technical work.

It's the technical skills.

Would you say that

Jamie: sort of, but if
you think like yes and no.

Like I think as I say I think that
there is, I think technical skills,

my honest opinion, technical skills,
by and large, particularly things

like Figma, particularly in, uh like
if you're applying for somewhere like

Microsoft or one of these other big tech
companies know that you will come into

an environment where there is almost
certainly like a very strongly defined

design system, things like that, that,
that will kind of, I'm not going to say

restrict your creativity, but they will
guardrail what you're able to do as

an interaction as I like, that's just,
I'm pretty confident in saying that's

probably prevalent across the other
big tech companies that exist as well.

It's certainly the kind
of case inside Microsoft.

And so, I remember the portfolios that
I review where they've tried to kind

of like, you know, you're showing.

You're trying to take the person,
like take the viewer of this portfolio

on a journey or through a story.

Like, so if you're going to
do a case study don't make it.

There's a, not like we don't, we
have sadly little time to read

the, kind of that to understand the
real technical skill that you have.

We will make very quick judgment calls
about those things based on what you

sort of share on in that portfolio.

But like, if you can hook with a little
story and maybe make that story just

slightly quirky or unique or something
to you or some way you approached it.

You'll probably be more likely
to kind of have a conversation

with a hiring manager after that.

And maybe if you can have that
conversation that goes, well, maybe even

an interview after that and who knows.

but yeah.

It's I am.


I'm always looking for something a
bit different when I'm looking at it.

Cause there's so much that's
that sensei and it's the same.

And it comes a little bit to sort
of, you know, when I graduated

20 years ago, gosh, that's a
terrifying thing almost 20 years ago.


It was 20 years ago.

There, there wasn't any of the
courses that there are existing

in things like UX and UI design
interaction, design there's courses.

I don't think that, you know, that
go back and further in the discipline

was a sort of nascent thing.

I know talented designers
inside Microsoft.

Who'd been there for sort of 30 plus years
and came in with a background as kind of

artists and could have print designers and
worked on some of the very first UI stuff.

But before that was even a thing.

and I think that one of the
challenges probably for the education.

established it's these
days is that there's.

So they're filling the market
with kind of people was round

about the same sort of skills.

So like, maybe it's interesting, like
with this idea of soft skills, like

what are the skills we can equip young
designers with to have them stand out?

and there were some colleges do that.

Well, some colleges focused
on the technical stuff, you

know, dependent on their,

Christian: yeah.

Well, I think that if more people
think the way you do, which is

it's a question then frightening,
potentially it could be potentially,

it's maybe easier to get into design.

Bye call me by coming from
a different background.

So if the texting, the technical
skill is not that important, I mean,

obviously it's important to have that
baseline fundamental, but if what's

more important is how we can build
relationships with people, how you can

foster trust, how you can talk about, or
I can still tell a story, all of that.

Then you might be able to do to start
in design from another industry as well.

Jamie: And you know what, that's a
great segue cause actually it touches

a little bit on this question.

You can ask me, I think at the end
of, by like what the self skill is,

is it, but also it reminds me that,
you know, And I think to start with,

this was a function of a little bit of
working in such technical design areas.

So, you know, I was design manager
for developer tools for years and

now we're working in design manager
for effort machine learning tools at

Microsoft, trying to find folks that
had a mixture of interaction, design

skills, a bit of those research skills,
and also had an understanding of ML.

I'm thinking about kind of most recently
the kind of to hiring up and doing that

sort of Venn diagram is finding that
people in the middle of it's super hard.

So you start to think actually one of
the most important bits and what are the

least important bits and what are the
beats I can teach people on the role,

what are the bits that like leads on
our team can help support kind of like

designers without maybe some of those
kinds of like, when I say technical,

I mean, when you say technical to me,
Technical as in, to kind of come to

understand this kind of AIML space, but
it's really a kind of the design craft

skinless, as well as the cross goes to.

I was thinking about
across dev tools in ML.

Like I have, I think I might be one
of the only people with an actual

arts graphic design background that
I've hired into one of these teams.

They almost, almost all of the
brilliant people that we've brought

into Microsoft have come through a,
what we call non-traditional background

almost all of them and many of them.

And I can't think of one
that hasn't flourishing.

Do you know what I mean?

Cause they can, they have the, the
guidelines and the foundation of a,

kind of like a good structure around
a craft and an understanding of that.

And it comes a bit back to that design
idea that you're kind of working within

guardrails and these big companies.

Um, but they also come in with a
slightly different, like a different

approach and if perspective things,
and I think that's really interest.

Christian: Well, let me know
what you think about this.

Cause you said earlier that Venn diagram,
when you look to hire someone, most of

the time you have a problem that you need
solved or, or that you need to field.

And then you, you have a
specific person in mind.

And whenever someone in an interview
is kind of like that person that

you have in mind, that's the
person you would try to hire.

So if, if it's a matter of the
person I need to hire is a person

that kind of fits what we need here.

Do you think that on the, on the
side of someone who's looking for a

job, it's also a matter of focusing.

So first of all, thinking, well, what type
of, what type of work do I want to do?

Which do I want to do consumer,
do I wanna do enterprise?

Do I wanna do super technical stuff?

Do I want to do, and then polishing
your skills and everything else that

you need around that to match the
type of job that you want to do or.

You just go as wide as possible, cast
the fishnet as wide as possible and

hope you're going to catch something.

Jamie: Um, it's probably the
former Christian, I think.

And I think, although I'm like personally,
I wish it was the latter and that people

were able to do all sorts of different
creative things and that, that would allow

them to get whatever job they wanted.

Having sat in the design
hiring managers sort of seat

for the last couple of months.

I know that I have preferred candidates
and been more interested in the

candidates that have a more enterprise
bent to the work that they do the

kind of enterprise kind of business
to business, internal tools stuff.

And it's, and it's, it's a sad fact
of like, and it's, it's not a sad fact

so much, but it's like, I'm thinking
kind of thinking about the candidate

as I'm looking at this stuff, because
I also want them to be successful.

I want, I don't want them to come into
a design team in Microsoft in this.

Consumer and other types of
work that Microsoft does anyway.

Um, but I w I wouldn't want them
to come into this very specific

space and not succeed and be a
struggle and really, really struggle.

I feel like, you know, in seeing that
I'm taking the opportunity away from a

bunch of people that may not have that
background, but want to get into AI and

ML space or, or developer tools as well.

But as you say as a hiring manager
you're kind of balanced with,

normally, if you have an open
role, you are, you have a gap.

And that normally means that things
are like leaking all over the place.

And you've got PLN engineering asking you
for when that design is going to start.

And these are all things that I've been
experiencing the last couple of months,

like how quickly can we fill that role?

There's always an, a speed, a speed
up that you're very rarely sitting

with an open job position going,
I just fancied hiring a designer

it's always, like, we need to fill
this role as fast as possible.

I mean, I, I think I've been very
lucky in the last, as I said,

the last one, the rules I've been
hiring for is that we hired so many.

We had three, three for my team
and one for a partner team.

And the advantage of having a few open at
the same time is that you, as you say, you

might meet somebody and you're like, this
is that perfect person for that thing.

But then you might need even
more perfect person, but you've

got a little bit more latitude.

Like we have a little bit more latitude
in the type of work that we're doing to

sort of go, actually, let's put that this
other person in this place, or let's put

this, you can figure it out often when
you've got one role as you've described,

you've got one gap that you're trying
to show that you're probably just trying

to fill that gap in the same, with the
same shape of person that you lost or

that's moved on from the team as well.

So, yeah, it's an interesting.

I love

Christian: change the topic a little bit.

Something that I wanted to
ask you is you're a manager.

Now a manager is a different career path
than the one of an individual contributor

than the one of someone who's sitting in
Figma all day and delivering or meetings,

reviews, whatever it is, I would assume a
lot of your day is spent around managing

one-on-ones hiring, maybe all of that.

So, but get one day know, a few
years ago you were a designer too.

And at some point you've decided
to make that shift into management.

And I'd like to talk a bit about that.

why have you done it and how do you think
looking back, what was the, what was it

at that point that made you want to move
into management versus staying a country?

Jamie: So I can only, so, so here's,
that's an interesting, so I I've just

started doing a bit of mentoring on
the ADP list website and I have to

say I've had a lot of people already
coming to me saying, I w either I want

to be a manager or I've been made a
manager and, or even just asking me

kind of consider the questions to that.

My journey to management was actually
genuinely, uh, I was incredibly

lucky to have a manager I had at
that point or a skip level manager.

So someone, someone moved out of
our team and we spent a good deal

of time in dev tools, trying to find
an alternative to that director.

And I was working, I was kind
of co-leading the team at that

point with the other very senior
design manager on the team.

And I just had a conversation with
the VP of program management and

he's, you know, he said, would you
be interested in, in taking this on?

And I was incredibly lucky for him to, I
think he saw a mixture of kind of a bit

of people skills that obviously design
an understanding of design and also a

kind of an aptitude around technical
that he thought would fit well for that.

So sometimes, you know, the step
into management is circumstantial

and I guess mine was circumstantial
and I'm kind of like, I, you know,

it wasn't my five to 10 year plan.

Probably I came into Microsoft as an IC.

I was enjoying being an IC and I
didn't also, I, you know, I don't

think one of the other things I say
to other people as well, I genuinely

don't believe you have to step.

I don't know if this is true everywhere.

I know it choose at Microsoft
and I know it's true.

I know it's not true everywhere
as well, actually, as is my point.

you shouldn't have to step into
management to continue a career like,

cause it's very, very different and I, I.

Experienced that very quickly,
you very quickly go from yeah.

Working in Figma.

And gosh, we used illustrator back then.

Um, and I'm into just talking about
appraisals and figuring out team structure

and having one-to-one with kind of unhappy
members of the team and trying to figure

out how you can help them support them.

and I.

I sort of grown to love that bit.

I think you have to sort
of love a bit of that.

I know lots of people that have stepped
into management and really not enjoyed

it and wants to go straight back to
IC or, or have, you know, in, in some

cases we've lost talent to the company
because they couldn't, they didn't

feel like they could step back an IC.

And I think there's like a very old
school way and I don't think this

is don't exist, just Microsoft.

, but I think that generally in industry
or business, it is seen as a step

down, if you go into management and
then decide you don't like it anymore.

And I think that's totally
broken because I think that

companies will continue to lose.

Great, great, great talent.

If, if we don't and it's not the companies
say that that's how it should be, but

we don't say that it can be different.

We don't say that enough.

You know, like we don't push that
enough and people still have this.

Nugget in their head where they
think they can't can't stay at

company because they cause they
don't want to be a manager anymore.

And I think that's a real
shame, but I've stuck at it.

I was incredibly lucky to work with
some really talented managers at the

time who really helped me on my kind
of like a management or management

manager transformation journey, as
well as having a brilliant manager

myself who would help me with that too.

So, but yeah, it was a circumstantial
change that ended me doing this.


Christian: enough.


All right.

Let's go to the end of podcast questions.

You might already have answered this
one, but I'll ask again, just in

case you have a different answer.

So what's one skill that you
wish more designers with.


Jamie: it is different.

Um, and I think I was thinking about this
earlier, that curiosity, I wish, and it

comes back to why I think, uh, why I think
the shape of designers needs to change.

And I, like, I think I, I wish
more folks were more curious

about the different things.

Of making products.

Like I wish more designers were
more curious, like, and that they

were more curious about research
and how to get involved in that.

They're more curious about like,
how do we measure things and

keep a track of that measurement?

They were more curious about like the
the code that goes in to building the

thing that they've designed to figure
out, how do we keep a track of that

and help the engineers Polish it like,
like all of that for me is curiosity.

I'm incredibly nosy.

and I'm curious, I think it comes
from my mum, uh, who won't ever listen

to this, so I can safely say that.

And then, and I think that I've
just, that's helped me connect

lots of dots, I think in the past.

And it's helped me build relationships
in spaces that aren't naturally designed,

because I'm just curious about what
they're doing and how that ties into

what we're all trying to do together.

This is not thinking about my team,
but just in general, I'd love.

If more kind of designers were more
curious about what else goes on in that

organization and how, how they might be
involved or even just informed about it.

Christian: Okay.

Curiosity is an answer
we haven't had before.

So I like that one.

That's pretty good.


What's one piece of advice that's has
changed your career for the better.

Jamie: So yeah, I mean, this
is, this is somewhat easy.

We've touched a little
bit on this as well.

And it probably was that moment
where I became a manager of the dev

tools team in, in, in Microsoft.

And it's when I started working
with my manager back then.

And although he wasn't a
designer he pushed me to think

about why for everything.

It's the idea of activities to impact.

And as like that, for me, the
idea of impact when you get it

unlocks everything unlocks, like it
helps you really think about even

your day to day or week to week.

What is the most important
thing I could be doing now?

X, like for me, it's for the team,
for the designer, it could be for

the project for, you know, everyone
has a different answer to that, but

like, why am I doing this thing?

I can always come back to this
idea of like, we are only given

eight hours time in a day.

And so you have to try and make sure
you're using it as wisely as you can.

I think, yeah, that's so it's
just keep thinking about why I

think is the thing that I I've
always been remote reminded of.

Christian: Good.

That's a good one.

I don't think we've had that one either.

So you've got two out of two.

Jamie, this has been such a great
conversation in case anyone wants

to follow up or they want to know
more about you, where can they

Jamie: reach out?


So, yeah, I am on LinkedIn
and you'll feel free to reach

out yeah happy to chat there.

also I'm, I'm enormously enjoying
the conversations I'm having

on ADP list at the moment.

If you want to have a chat with me
there about any of the stuff we've

just talked about or anything else
to do with kind of like design or

management or any of those things,
then I'm happy to kind of like, yeah.

Happy to chat to you.


Christian: Timmy, once again.

Thank you very much for being part
of the design mitzvahs, this journey.

This has been really cool.

A great conversation.

We'll catch

Jamie: up soon again.


Thank you.

Christian: What a season?

This has been 10 shows, 10 fantastic
conversations about the value of design,

how we can become better and more
efficient and more effective at our work.

How can we set our best foot
forward when looking for work?

We've also talked a lot about
building trust with your product

team and your internal stakeholders.

We've talked about learning how to
use daytime metrics to your advantage.

This has been a season
packed with knowledge.

I am beyond excited for
season three next year.

And until then, I'd appreciate it.

If you could leave the podcast a review,
and if any of these conversations

has been useful to you, I hope you'll
share them with your community.

I'll sign off for now.

And thanks a lot for listening.

I cannot wait to bring you 10 more of
these conversations in the next season.

Creators and Guests

Christian Vasile
Christian Vasile
🎙️ Host & Growth Product Designer
Microsoft's Jamie Young on Storytelling and the Need for Designers to Evolve
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