November 2, 2023 • 38 mins
In this first episode of Unserious, J.B. and Molly speak with design leader and coach Courtney Kaplan about practical ways to manage creativity and personal growth during a particularly difficult time in the workplace. She shares advice from founding design operations at Facebook, highlights how leaders can create safe spaces for their teams and manage stress effectively. Finally, Courtney discusses coaching and the benefits it can bring from navigating fast-paced work environments to working toward larger personal transformations.
“The promise of being your best self or transforming that self - people get excited about those promises. But the truth is that true transformation comes from practical ways of being a little bit different over time.” - Courtney Kaplan
00:00 - Intro
03:02 - What’s keeping creative people up at night?
06:30 - Demonstrating value to the business
12:24 - Hire, Fire, Boss!
15:24 - Creativity through structure
25:44 - Navigating stress and finding moments of calm
27:56 - Transformational coaching
35:58 - Wrap-up
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
J.B. Skelton (00:04):
It might be the most often repeated observation
about modern living, but it'sundeniably true.
The only constant is change.
David Bowie wrote his classicChanges 50 years ago, when
people felt like they couldn'tkeep up with transformation in
society, in values, intechnology.
That was true long before hewrote it and it feels more true
(00:28):
now than it possibly could havebeen.
It seems there's nothing morehuman than the feeling that the
roller coaster is just roundingup the top of the climb and
about to fall fast.
We can't get off the ride, wecan't slow it down, whether we
like it or not.
The only way we can go isforward Change, generative AI,
(00:51):
automation, corporate downsizing, industry transformation.
So if we can't stop theonslaught of change, how do we
manage to work, create andcommunicate during what feels
like a constant barrage ofdisruption?
As creative people, part of theanswer is to band together and
try to have some goddamn funwith the problem.
(01:11):
Laugh, fail, scream a little,because when we can get some
distance from the seriousness,we see the problem space in a
new light.
We see opportunities we mightnot have otherwise, and lowering
the stakes helps us take careof our teams and ourselves.
In this first season of ourpodcast, we're going to explore
(01:32):
how we manage and manifestcreative impact amid constant
change with some extraordinaryindustry leaders who we know and
admire.
I'm host JV Skelton.
Molly McMahon (01:42):
I'm host Molly McMahon, and our producer is
here as well.
J.B. Skelton (01:47):
And this is Unserious.
There's an old trope thatcreative people are disorganized
or they can be chaotic to workwith.
But we know that creativeinspiration doesn't just come
from a bolt of lightning whileyou're pouring your orange juice
, and developing great creativeideas can require big teams from
lots of different disciplines.
(02:07):
A successful career ofcreativity requires structure,
planning and rigor toconsistently solve problems in
interesting ways.
Nobody knows that better thanour guest today, courtney Kaplan
.
Courtney has a knack forhelping designers and creative
leaders find their path togreatness.
With over 25 years ofexperience in the design world,
(02:29):
she's seen it all, from agencylife at Hot Studio to founding
design operations at Facebook,to now her transformative
coaching business iconicleadership coaching.
She's been in the trenches andtoday she's going to share her
insights on how individuals andteams can maximize creativity in
these turbulent times.
Let's give a warm welcome tothe one, the only, the truly
(02:53):
incomparable Courtney Kaplan.
Courtney, welcome to Unserious.
Courtney Kaplan (02:59):
Thank you so much for having me.
I'm really excited to be withyou all.
J.B. Skelton (03:03):
This is a really odd time for a lot of people
working in Silicon Valley and inthe tech sector more broadly.
Resources are constrained,trust is low and people are
tired.
In your business iconicleadership, coaching and as an
industry leader, what are youobserving out there?
What's keeping professionals inthe creative industries up at
(03:25):
night these days?
Courtney Kaplan (03:27):
Yeah, I mean.
I think the truth is it'sdifficult times.
Either you're looking for arole, and that has a lot that
comes with a lot, or you're in arole without most of your team.
You're either overwhelmed orout looking for work.
I think what keeps people up atnight is we've heard this
(03:49):
happen in other industries.
You hear it happen in differentindustries across time, but it
hasn't this is the first timethat this digital world is
cannibalizing itself of.
Let's take these principles ofefficiency and doing more with
less and apply them to ourselvesand get rid of all of this
(04:10):
talent.
That's really hard to reconcile.
As I talk to my clients,they're concerned.
The rules of the game are stillthere.
Expectations are highperformance, requirements are
high, review cycles happen acouple times a year, plus, plus,
plus.
(04:31):
But they don't have theresources to make these things
happen.
Their bosses or the peoplethey're reporting to still
maintain the high expectations,because they have high
expectations of them, plus, plus, plus.
There's no adjustment offocusing, condensing, slowing
down, pivoting, doing more withless.
(04:53):
With it, at some point, youjust hit capacity that people
just don't have the capacity todo more.
J.B. Skelton (05:01):
How should leaders be thinking about getting great
creativity in an environmentwith very resource constrained?
Courtney Kaplan (05:11):
I don't think the constraints aren't the
problem with creativity.
Any kind of great creativityusually has some kind of
constraints or parameters thatyou have to perform with it,
unless you're an artist out inthe world doing your own thing
however you want to do it.
Any professional field whereyou are creative, there's a
(05:31):
budget, there's a timeline,there are constraints.
I don't know that theconstraints are wrong.
I think it's the expectationsor the ability to really focus
of what's absolutely mostimportant, what we're actually
trying to do, and included inthat mix having some care of
those creative folks, because aburned out creative is not going
(05:54):
to be very creative.
Constraints are fine.
Reduced resources that happens.
We've all had very creativemoments under reduced resources.
But if the expectations arestill sky high and people are
feeling burned out and not caredfor, that makes it tough to be
very creative.
I think that good leaders aregoing to need to through this
(06:16):
whole moment, remember their ownhumanity, care for their teams,
make their teams feel trustedand cared for.
It's a difficult time, butwe're in it together.
We'll get through it.
Just make sure that I'msupporting all of you to get
through this moment instead ofoperating from fear and being
like hey, the expectations arestill the same.
(06:37):
Keep cranking it out.
Molly McMahon (06:40):
I wanted to talk to you a little bit about design
teams.
You have been one of theleaders in design operations or
design ops, and we're going totalk about this a little bit
later.
But design ops is basicallywhere organizations
operationalize and scale designprocesses and teams to make
design more efficient andeffective.
(07:02):
But I'm curious to know yourthoughts about why so many
design teams and designers werecut by tech companies this year,
particularly when you thinkabout what designers can do,
their ability to do more withless creative problem solvers.
It seemed to be a field thatreally took a lot of heat in the
(07:25):
layoffs that have beenhappening across Silicon Valley.
Courtney Kaplan (07:29):
I feel like there's this belief of as long
as we have engineers, we canbuild it and everything else is
secondary to that, for better orfor worse for the rest of us,
for consumers who have to usethose outputs or those what is
actually shipped.
I think that there's that corebelief, especially out here,
that engineers are the mostimportant and if we can build it
(07:52):
, that's the most importantthing.
Then research, design, contentstrategy, some of these other
roles are really nice to haveand can be super useful, but we
just don't need as many of thosefolks.
We don't know what they do allday.
Then I think that even insophisticated organizations that
can somewhat be the attitude Inorganizations that aren't as
(08:16):
sophisticated certainly theydon't value or feel that they
can't put resources towardsdesign, user experience, content
strategy.
Those things are nice to have.
J.B. Skelton (08:29):
How do designers demonstrate their understanding
of business objectives better?
Courtney Kaplan (08:34):
Yeah, it's interesting I've seen it happen
really well in many cases acrossmy professional experience
where a designer will latch on,usually not to a big, big, big
KPI or a really big problem, butsomething that they can get
their arms around.
That offers a great case studyor a great example of what
(08:55):
design can do They've been ableto put together.
This is what we're trying toachieve and why.
Here's how design could helpthat.
Because I've done some researchand I've unpacked the problem
more deeply than just making thechart go up and to the right,
and so I can represent what'sactually happening and what the
real problem is and how we canchange it, and I've even shown a
(09:17):
couple of solutions that wecould test to see if I'm right.
I might be wrong, but we couldtry it.
Then someone's like we couldtry it.
Then, if you try it, then ifyou're saying, oh wow, this
person has, there's some actualrelevance here.
This makes a lot of sense, thenyou gain trust and I think that
for most designers you'reprobably not gonna understand
(09:37):
the big business capital B,capital, b, big business.
But if there's a feature on aproduct or a specific way that
you see huge inefficiencies,jump in, dig in, articulate it
and tell the story to everybodyyou know Don't assume that they
see the problem the same way youdo and then come up with
(09:58):
solutions and explain how yougot to the solution.
Those kinds of conversationscan be really illuminating and
great practice for designers.
Molly McMahon (10:09):
Yeah, it's interesting because I've been
recently doing work consultingfor product teams and design
teams inside of product teamsand one of the biggest
challenges that I've been seeingis that the design teams really
focus on process or they'relike this is my design process
and this is how weproblem-solving this way, but
(10:31):
sometimes that can be reallyisolating to the product
designers or the productmanagers and the engineering
team because they have adifferent process for problem
solving.
What advice would you give whenyou think about designers today
and thinking about all thesechallenges that they're facing,
and what advice would you givethem for how to work inside of
(10:54):
their current organizations?
Courtney Kaplan (10:58):
One of the things that I tell people right
now is to kind of define what'syour commitment, because right
now people are burned out,they're resigned, they're
resentful, they're angry, right,but they're still pushing
themselves to do great work, andso they're still working late
but they're bitter about it.
Plus, plus, plus.
This kind of builds thisbitterness snowball, if you will
(11:19):
.
And so I say look, step back.
What are you committed to?
Are you committed to getting apromotion?
What's that gonna mean?
Are you committed to being homewith your kid?
What does that mean?
Where is your commitment?
And then be in it with bothfeet because that divided
resentment, but I gotta show up,resignation.
Nothing changes around here,but I gotta be here.
(11:40):
That's not a creative,generative, exciting position to
take.
You're just kind of, you know,hamstringing yourself a little
bit.
You're a little hamstrung toactually take action that's
going to get you anything youwant.
Listen, if you're like look,this is just a terrible time in
the industry, I'm just going toput my head down and do my work
(12:01):
and do my thing and not expectto promotion or not expect
anything specific for the nextcouple of years, because it's
terrible.
At least that's where yourcommitment is and you can sleep
well at night knowing that'swhat you've decided.
But there's a lot more.
There's a lot more you can openup and decide.
What am I committing to rightnow?
J.B. Skelton (12:24):
Let's take a sharp break and when we get back
we'll dig deeper on designoperations with coach and design
leader Courtney Kaplan.
So, courtney, we've all playedMaryfuck kill before with our
friends, but we put a differenttwist on it here at.
On serious, it's a rapid firegame that we call higher fire
boss.
The rules are the same, exceptyou will have to choose one of
(12:47):
the three people on yourfictional list to hire, one to
fire and one to be your boss.
Courtney Kaplan (12:53):
OK.
J.B. Skelton (12:55):
You ready.
Courtney Kaplan (12:56):
Yes.
J.B. Skelton (12:57):
OK, jalo Beyonce or Shakira.
Courtney Kaplan (13:01):
Oh gosh, I would say Jalo hire Beyonce boss
, shakira fire.
J.B. Skelton (13:12):
OK, oh.
Molly McMahon (13:18):
That was fighting words.
I don't know.
I'm a big Shakira fan.
I'm like, oh wow, shakira gotkicked to the curb.
Oh, wow, ok.
J.B. Skelton (13:29):
Molly, do you want to give the next three?
Molly McMahon (13:31):
Oh sure.
Well, Courtney, you have been acoach to some of us here,
including myself, and we werethinking about who in the self
improvement section of theKepler's bookstore would you
want on your team.
So the options are Brene Brown,adam Grant and Dale Carnegie.
Courtney Kaplan (13:59):
I think Brene Brown.
I'm kind of a Brene fan girl.
Adam Grant is great, but Breneso where is she?
J.B. Skelton (14:10):
Where is she?
Is she your boss?
Do you hire her?
Courtney Kaplan (14:13):
Oh she's, I hire her.
J.B. Skelton (14:16):
Congratulations.
Courtney Kaplan (14:17):
And Dale Carnegie fire, because I don't.
I think he's kind of done, youknow what I mean.
And Adam Grant's boss, I think,because he's level headed and
very calm and rational.
I'm.
Molly McMahon (14:30):
Molly, your face still looks like.
It's not cool.
You're like what?
No, no, no, no, I can getbehind that.
I can get behind that.
We were chuckling over DaleCarnegie being tossed in there
with those two as well, daleyeah, he's old school.
J.B. Skelton (14:46):
We were trying to decide Tony Robbins or Dale
Carnegie.
Do you want to hear something?
Courtney Kaplan (14:50):
so earnest and so sadly earnest.
When I was 13 years old I wassuper, super shy, like really
shy, and I could tell I wanted abetter social life and I was
kind of in like the Bible studygirls social group and I read
Dale Carnegie's how to makefriends and influence people.
But because I was 13, Iearnestly put each suggestion to
(15:13):
work.
Wow, and it was really popularin high school.
Okay, one of the things thathappens is an engineer can build
something and it works or itdoes not work.
Right, they kill a bug and theycan check a box or not check a
box.
For a designer, that's just notthe case.
(15:35):
They generally have to connectacross multiple teams, have
research, understand what'sgoing on.
I have a conversation withengineers.
So so much of their job iscommunication, which is fine,
but having design operationshave a way.
Where does this communicationlive?
How do we structure it in a waythat we're having conversations
(15:56):
that move us forward, work inthe next new person that joins,
find these conversations fromthe past and get up to speed
really quickly?
All of those kinds of thingsmake it so that the design team
can actually be effective.
Otherwise they would just be inmeetings all day and, by the
way, a lot of folks that areamazing, incredibly talented
(16:19):
designers might not care for thepolitical hustle of going
around setting hey, let's makeour comms plan.
Hey, let's set up what we'regoing to do for our all hands.
They're not interested in someof the work that goes behind the
scenes to do all of thesedifferent roles that help them
stay robust and healthy.
Molly McMahon (16:37):
Yeah, I always think about design operations
and or design program managementas an opportunity to set
structure, and so I'm curiouswhat your thought is around what
the importance of thatstructure is for catalyzing
creativity and catalyzingproblem solving Right.
Courtney Kaplan (16:53):
Right.
So for anyone to have kind oftheir container for creativity,
having a rhythm of what yourweek is going to look like makes
it's a big help.
Knowing Wednesday is your makerday.
You don't have any meetings onWednesday.
Knowing every Monday you'llmeet with your full team and
have an opportunity to presentif you need to.
Knowing quarterly there's anall hands and there's an
(17:16):
opportunity to finish work andpresent to the larger group.
Knowing what your review cyclesare like, or your design reviews
or your critiques If you knowall those things, you can work
and work freely within thatstructure and container.
But if no one's setting that upin a way that's well designed
itself, you kind of have a getyanked around like oh my God,
(17:36):
critiques today.
Oh my God, we've got to presentto our leads tomorrow.
Wait, we can't present that toour leads, we haven't presented
it to our cross functionalpartners.
It can be really messy andreally churning.
And so, being able to havedesign program managers set up a
logical path or some logicalcheckpoints or some logical ways
that this work can happen, letthat part of your brain relax so
(18:00):
that you can focus on doinggreat design work right, because
someone else is making surethat there's a check-in and
there's next steps available ina predictable place.
Molly McMahon (18:10):
Yeah, I often think about that structure
creating certainty in anambiguous process.
Yes, I love that.
So it's like calms you a littlebit.
You're like, oh, okay.
Well now you have the chance tobe expanded.
I'm not going to be offensivehere, but I can only do it for a
certain amount of time and thenwe're going to have to make a
choice at this moment, and Ithink it's really powerful.
Courtney Kaplan (18:30):
That's right, creating those kind of packets
of those containers of creativetime where you can think how the
discussions, have explorationsand not just be on a constant
hamster wheel of to-dos andmeetings.
Yeah, yeah, but that's aconscious creation, it doesn't
happen naturally.
You have to actually make thoselittle, that design, that
(18:53):
structure, so that you have thatspace to be creative and
thoughtful and connect and havedeeper conversation than
otherwise.
Molly McMahon (19:00):
Yeah, I agree.
J.B. Skelton (19:03):
Now, courtney, I remember this story.
It was in the middle of this.
I think it was the summer of2012.
And I was working with KateAronowitz, who was the head of
design at Facebook, on a clientpresentation to a big European
(19:24):
fashion house that she washelping me on, and she was like
so I came over to her desk on aFriday afternoon and she was
just like we just made thebiggest acquisition I just
closed, the biggest acquisitionthat Facebook has ever made,
which, of course, was theacquisition of Hot Studio.
At the time where you were, andat the time, that was the
(19:47):
single largest acquisition thatFacebook had made.
We went on to spend $23 billionon WhatsApp, but we started
with Hot Studio, and that wasreally the introduction of
design operations to Facebook.
So what are the lessons thatyou have for people that are at
(20:12):
that starting point?
What are the things that youwould absolutely say are
essential and the things thatyou would never do again?
Courtney Kaplan (20:19):
Yeah, I think that things that are absolutely
essential is there are going tobe fans that are excited to hear
about what design operationscan do and the support that's
available.
Work with those people andthere are going to be people who
aren't fans.
They just don't buy it right.
Just stop selling.
You don't need to find.
Let them run their team the waythey want and sooner or later
(20:42):
something will happen andthey'll be like oh well, that
would have been really helpfulto have design ops.
Then you can be gracious andhelp.
But don't try and sell peoplewho aren't ready or who aren't
bought in, because there areplenty of folks that are excited
, they're ready, they're eagerto learn and understand how to
partner, and there's more thanenough work among them, and
there's more than enough work,so for sure, that's one of the
things that I think that'sreally important.
(21:04):
Secondly, I think that a lot ofnew design ops teams myself
included was we were like asmall team of generalists at the
very beginning and we werewilling to do it all right.
Anything you need help with,I'm happy to help.
That wasn't a great strategy.
I think we are still feeling itout to feel where let's do it
(21:25):
all and then see what we'reactually best at or where we add
the most value.
But in that doing it that way,I think it's easy to burn people
out or make people moreconfused about what you're doing
because it's unclear.
So if I had to do that partagain, I would at least start
with a stake in the ground.
So here's what we do.
Here's probably what we don'tdo.
(21:46):
That could change, but for nowhere's what we do.
Pick a major, do well in yourmajor, and then you can always
expand and kind of havedifferent flavors later.
J.B. Skelton (21:56):
I love the way that you put that.
How has managing creativeoperations influenced your own
personal growth?
How has it changed yourperspective on creativity?
Courtney Kaplan (22:10):
There's a lot of pressure to do something new
and amazing and flawless andseamless and frictionless and
all these things.
There's a lot of pressure andthat these designers can be kind
of sensitive souls that needsome TLC and some care.
As a leader realizing it makessense to put in some time to
(22:30):
connect with people as a person,let them know they're cared for
and that they can, you can calmdown.
Keeping people calm and feelinglike it's okay, they're safe
and Safety, then you can becreative and generative.
But if you're worriedconstantly that something bad is
gonna happen or some somethingyou don't know is you know that
(22:53):
you can't expect is gonna happenaround the corner that's not a
great creative place to be.
So if you're a leader and youcan kind of like Keep people
chill, reassured, to be atransparent communicator yeah,
you know, be honest and upfrontand be a trustworthy person that
helps create kind of theenvironment that you're gonna
(23:14):
want to see creatives working,thrive, stay and grow and Tell
their amazing friends to comework for you too.
J.B. Skelton (23:22):
So that's something that comes very
naturally to you, like you areable to, you are, you were able
to and I say this is someone whoworked on your team and you,
you, you show a lot of care, you, you create safe spaces and you
lower the stakes Of projectsand not everything feels like
(23:45):
this do or die situation.
What is your advice to folkswho are, who are in new
management, who may not come by?
That is naturally and asInstinctually as you, you do.
What is your advice to them inways to create that and to
create saver spaces for everyone?
Courtney Kaplan (24:06):
right.
I think for new managers, a lotof times they act out of fear,
right.
Yeah, they just got a new role,they just got that promotion.
They don't want to let anybodydown and they're gonna finally
be able to show everybody thatthey've got some control and
power.
You know, they've got an ounceof power and they're gonna use
it.
So, I think, to be able to notact out of fear, to be able to
trust your team People makemistakes, but you can also work
(24:28):
through mistakes.
There are performance issues,but you can also work through
performance issues, and that'sthe job.
A lot of my clients come to meTalented, amazing people.
They've just gotten theirnewest role and they've hit
their edge right.
I was pretty confident when Iwas the manager.
I was pretty confident when Iwas a manager of managers.
Nah, I'm a director, I don'tknow what the heck I'm doing.
(24:50):
I'm terrified, yeah.
And so when you can admit thatto yourself, say I'm terrified,
then it's time to kind of sayokay, what kind of support do I
need?
You know, what kind of help doI need?
Is it a coach?
Is it a mentor?
Is it a group of peers I trust?
How can I make myself feel moresafe, to create a more safe
space and operate from a senseof care and dignity, not a reign
(25:13):
of terror.
Molly McMahon (25:15):
I love that, and I say that because when you do
move up into leadership roles,it's isolating and you can
really feel like you're shootingfrom the hip or you're alone in
your decisions.
Because, and because it's hardto get time with your, with your
peers, you're also Earningtrust with your peers.
(25:39):
The people who can help andsupport you in that leadership
role tend to be even busier.
Yeah, absolutely.
Courtney Kaplan (25:46):
Absolutely.
I couldn't have said it bettermyself.
It's true, when you're a leader, you are alone, you are
shooting from the hip, you arenavigating really tense
situations on uncertain moments,and then you layer that with
some of the other things thatwe're all experiencing on this
planet and you know politicalscenes plus, plus, plus, all
these Things that kind of piledon everyone's a little bit.
(26:07):
You know fried, yeah, yeah,finding those I call them Stress
management strategies, to havea true strategy that you're
committed to to reduce yourstress.
It's not gonna happen,naturally, it's not gonna become
easier, it's not gonna happenover the weekend.
So, what is your strategy toreduce stress?
(26:27):
You shut your phone off atnight.
Do you Meditate, yoga, run, geta dog, whatever the heck it is,
so that you that you know thestress is a part of my life.
Yeah, it seems like it'sgetting more intense.
I need to actually activelyaddress this and not hope that
it goes away.
I used to do a thing atFacebook that I called meeting
(26:49):
meditation and all I would do isrealize I'm in a meeting room
with people.
I don't need to clench my jaw,that's not helping.
I don't need to hold tension inmy shoulders might they aren't
doing anything.
In this meeting I can actuallyfully relax my body, still pay
attention and participate.
Follow my breath, participate,follow my breath, participate,
(27:13):
and then your body is.
J.B. Skelton (27:15):
Existential life-changing?
Courtney Kaplan (27:21):
Yeah, you don't have to have.
You don't have to hold ameeting with your face like a
scrunched you can.
Physically relax, like go sinkinto those beautiful chairs that
they have Focus on your presentZen out a little too much.
J.B. Skelton (27:37):
No, she says that with a huge smile on her face.
Molly McMahon (27:47):
A little.
J.B. Skelton (27:47):
Colgate glint on a teeth.
I know I was known as a shittydegree.
Molly McMahon (27:56):
When we come back .
Transformational coaching withCourtney Kaplan more and serious
in just a moment.
Courtney, so you and I metbecause I was seeking a
(28:16):
professional coach.
I was also curious to learnmore about design operations and
I was wondering if I shouldbecome a coach myself, and I'm
actually not alone in that.
There is a rise in coachingright now.
The number of professionalcoaches out there has risen 30%
in recent years and there'ssomething like 71,000 coaches
(28:38):
worldwide.
As One of those 71,000 coaches,what's driving this increase in
demand for coaching?
Is there a paradigm shiftthat's happening around what it
means to lead organizationstoday?
I think things are changing sofast Right now.
Courtney Kaplan (28:55):
Things are changing so quickly and you're
expected to kind of like be anexpert in whatever is happening
now, when that's reallydifficult to do.
And someone compared it toprofessional baseball players
practice, and practice andpractice all week long.
They practice spring training,they practice, and then they do
(29:18):
one game a week, right, For acouple hours.
You go to work and you're onthe spot doing it.
There's no practice work, it'sall just doing it, expecting to
hit home runs Left and right.
Molly McMahon (29:32):
That's very hard.
There's no rehearsals.
Courtney Kaplan (29:34):
That's very hard.
There's no rehearsal, there'sno practice.
So I think that bringing incoaches helps shortcut a lot of
the learning cycles that peoplewould otherwise have to go
through, helps people realizeand get more honest with
themselves more quickly, right?
Oh, you know what?
I'm not a good listener.
I've kind of heard that from afew people at work, but I
(29:56):
haven't really taken any actionbecause I don't know what to do.
A coach can help you figure outwhat to do.
Hey, you can do this.
Hey, you can practice this.
Let's do that, let's do this.
That's very useful, and so thattakes.
So, for leaders today that areworking in fast changing
environments less resourcesdependent on their leaders, all
the way down to brand newmanagers to keep things rolling
(30:19):
you want all of those people tobe trained and have some kind of
support, and it's not gonnacome naturally.
And I think also in the oldendays it was easy to kind of ask
the older people at work.
Sometimes now there are noolder people at work, right,
things have changed so much thateither industry is new and it's
(30:40):
a lot of younger folks, or theway that older people did it
isn't as relevant to what youneed to do in your role, right?
I think about it like Iwouldn't be able to ask my dad
how to resolve something overSlack.
It's just not.
It wasn't his world right.
So in a lot of cases things arejust moving so quickly that
(31:04):
that support even making thespace to give yourself the
support, have the conversationsreflect, unpack the problems
that you're having makes a bigdifference.
Molly McMahon (31:16):
Can you talk to us about what transformational
coaching is?
That's your promise at IconicLeadership Coaching.
Can you tell us a little bitabout what it is and how it sets
you apart from other coaches?
Courtney Kaplan (31:32):
Yeah, for sure, I think.
When I talk abouttransformational coaching, I
think there's a radical shiftthat we have a possibility to
make.
That's not far away, but weresist making it because we
think we're gonna have to giveup too much, right?
So, for me, I wanna be a coach,but if I am a coach I'd have to
give up my job and that means Ihave to sell my house and I'd
(31:54):
have to be.
We make it so hard for us tojust do what we want to do, and
so in transformational coachingwith my clients, we make this
space to just let you explorewhat might be possible for your
life, professionally andpersonally and a lot of my
clients are coming forprofessional reasons.
Let's break down some of thestories you've created about why
(32:16):
it can't happen or why it's nothappening, or who's preventing
you from happening, from makingthat happen, and then let's make
a little, have some littleexperiments where you can try a
few things.
Right, If you're like, oh, I'mintroverted, I just don't speak
up in meetings, let's make acommitment just to speak up in a
couple meetings, not the bigones with the CEO, but some
smaller meetings with people youtrust.
(32:37):
Push through some of these oldstories that you've got to see
what might be possible there,right?
And so suddenly, slowly andsurely, I'm moving people from
where they are, square A, tosquare B, C, D, E, whatever,
without the fear and terror ofthat big, huge jump.
(32:59):
I have to make a big, huge leap.
You don't have to make a big,huge leap.
Let's start with someexperiments.
Where do you feel comfortable?
What might be possible, right?
So that allows people to havethat creativity and freedom to
explore things.
So I've had clients that arelike I want a promotion, that's
all I want to do.
I want to get a promotion.
So I'll say listen, let's talkto some of the people that have
that job and see if that's whatyou want to spend your time
(33:22):
doing.
And they've changed their mind.
I don't want a promotion, Iwant to stay in my role.
J.B. Skelton (33:29):
I want to do exactly what.
Courtney Kaplan (33:30):
I'm doing, but I want to do it in a different
way, or I do need more money, orI do want a bigger bonus.
That's fine.
You know a lot of times thepromise of being your best self
or transforming that self.
People get excited about thosepromises, but the truth is that
true transformation comes frompractical ways of being a little
(33:53):
bit different over time,unpacking uncomfortable topics
and understanding them better sothat you can understand
yourself better and make changesin your life.
And so I think that I reallyget excited when I get to work
with clients and help themactually shift the way they show
(34:14):
up at work and at home and thenrealize promotions, new jobs,
moves, new relationships,traveling the world, whatever it
is.
That is a blast to not onlysupports people in what they
want to accomplish, but to seethem accomplish.
It's super fun.
J.B. Skelton (34:39):
Courtney, you are just an incredible design leader
, thought leader, people leader.
You're a coach, you're afounder, you're a writer and now
you're even a teacher.
Where can people keep up withyou online?
Courtney Kaplan (34:55):
You can find me at my website,
iconicleadershipcoachingcom.
You can also find me onSubstack under
iconicleadershipcoaching.
Molly McMahon (35:05):
I do a bi-monthly newsletter twice a month
newsletter which I always sendout to my pals.
I'm always like this is gold,so get on the newsletter.
Courtney Kaplan (35:17):
Love writing that newsletter super fun.
Yeah, those are probably thebest spots.
And, yeah, this fall I'mteaching at California College
of the Arts.
It's a blast.
I just had one class so far.
My class is Communication byDesign.
So excited to get in there.
(35:40):
Yeah.
J.B. Skelton (35:40):
I love it yeah.
Thank you.
Thank you for being a friend,thank you for joining us on
Unserious.
Courtney Kaplan (35:47):
Thanks, Courtney.
Thanks for having me.
This is a ball.
So great to see the three ofyou.
J.B. Skelton (35:52):
You're a star, thank you.
Courtney Kaplan (35:54):
Oh, thank you.
Molly McMahon (35:58):
Oh wow, courtney, really named the complexity.
The plus, plus, plus we are allfacing in our personal and
professional lives and sharingtransformative ways to commit to
ourselves amidst constantchange.
Jb, what were your takeawaysfrom that one?
J.B. Skelton (36:14):
Well, first off, I'm always struck by how
Courtney creates space forhumans to work as humans and
that safety turns just a groupof random people into a very
connected team Totally.
I also was really struck by herstory from Junior High about
saying hello to everybody in thehallways.
(36:36):
It's something that I do tocreate more community and real
warmth and communication amongthe people I work with as well.
Molly McMahon (36:46):
Yeah, I love that too, and I also am taking away
with me the meeting meditation.
I'm definitely writing a stickynote with meeting meditation in
my notebook for my next complexmeeting, yeah.
But additionally, I alsoadmired the radical candor
Courtney shared in asking us tobe honest about addressing our
own areas for growth, beingclear that it's up to us and our
(37:07):
commitment to transform or not.
J.B. Skelton (37:13):
And that's the show.
Unserious is in its firstseason.
Please subscribe, rate us,share it with your friends.
It means so much to a new showlike ours.
Keep tabs on us on our website,Unseriousfun, or find us on
Instagram, also at Unseriousfun.
Special thanks to ourincredible producer, Micah Vonow
(37:36):
, who's had a huge hand inshaping the content and the soul
hand in editing it for us today.
Thank you so much for tuning in.
It might be the most often repeated observation
about modern living, but it'sundeniably true.
The only constant is change.
David Bowie wrote his classicChanges 50 years ago, when
people felt like they couldn'tkeep up with transformation in
society, in values, intechnology.
That was true long before hewrote it and it feels more true
(00:28):
now than it possibly could havebeen.
It seems there's nothing morehuman than the feeling that the
roller coaster is just roundingup the top of the climb and
about to fall fast.
We can't get off the ride, wecan't slow it down, whether we
like it or not.
The only way we can go isforward Change, generative AI,
(00:51):
automation, corporate downsizing, industry transformation.
So if we can't stop theonslaught of change, how do we
manage to work, create andcommunicate during what feels
like a constant barrage ofdisruption?
As creative people, part of theanswer is to band together and
try to have some goddamn funwith the problem.
(01:11):
Laugh, fail, scream a little,because when we can get some
distance from the seriousness,we see the problem space in a
new light.
We see opportunities we mightnot have otherwise, and lowering
the stakes helps us take careof our teams and ourselves.
In this first season of ourpodcast, we're going to explore
(01:32):
how we manage and manifestcreative impact amid constant
change with some extraordinaryindustry leaders who we know and
admire.
I'm host JV Skelton.
Molly McMahon (01:42):
I'm host Molly McMahon, and our producer is
here as well.
J.B. Skelton (01:47):
And this is Unserious.
There's an old trope thatcreative people are disorganized
or they can be chaotic to workwith.
But we know that creativeinspiration doesn't just come
from a bolt of lightning whileyou're pouring your orange juice
, and developing great creativeideas can require big teams from
lots of different disciplines.
(02:07):
A successful career ofcreativity requires structure,
planning and rigor toconsistently solve problems in
interesting ways.
Nobody knows that better thanour guest today, courtney Kaplan
.
Courtney has a knack forhelping designers and creative
leaders find their path togreatness.
With over 25 years ofexperience in the design world,
(02:29):
she's seen it all, from agencylife at Hot Studio to founding
design operations at Facebook,to now her transformative
coaching business iconicleadership coaching.
She's been in the trenches andtoday she's going to share her
insights on how individuals andteams can maximize creativity in
these turbulent times.
Let's give a warm welcome tothe one, the only, the truly
(02:53):
incomparable Courtney Kaplan.
Courtney, welcome to Unserious.
Courtney Kaplan (02:59):
Thank you so much for having me.
I'm really excited to be withyou all.
J.B. Skelton (03:03):
This is a really odd time for a lot of people
working in Silicon Valley and inthe tech sector more broadly.
Resources are constrained,trust is low and people are
tired.
In your business iconicleadership, coaching and as an
industry leader, what are youobserving out there?
What's keeping professionals inthe creative industries up at
(03:25):
night these days?
Courtney Kaplan (03:27):
Yeah, I mean.
I think the truth is it'sdifficult times.
Either you're looking for arole, and that has a lot that
comes with a lot, or you're in arole without most of your team.
You're either overwhelmed orout looking for work.
I think what keeps people up atnight is we've heard this
(03:49):
happen in other industries.
You hear it happen in differentindustries across time, but it
hasn't this is the first timethat this digital world is
cannibalizing itself of.
Let's take these principles ofefficiency and doing more with
less and apply them to ourselvesand get rid of all of this
(04:10):
talent.
That's really hard to reconcile.
As I talk to my clients,they're concerned.
The rules of the game are stillthere.
Expectations are highperformance, requirements are
high, review cycles happen acouple times a year, plus, plus,
plus.
(04:31):
But they don't have theresources to make these things
happen.
Their bosses or the peoplethey're reporting to still
maintain the high expectations,because they have high
expectations of them, plus, plus, plus.
There's no adjustment offocusing, condensing, slowing
down, pivoting, doing more withless.
(04:53):
With it, at some point, youjust hit capacity that people
just don't have the capacity todo more.
J.B. Skelton (05:01):
How should leaders be thinking about getting great
creativity in an environmentwith very resource constrained?
Courtney Kaplan (05:11):
I don't think the constraints aren't the
problem with creativity.
Any kind of great creativityusually has some kind of
constraints or parameters thatyou have to perform with it,
unless you're an artist out inthe world doing your own thing
however you want to do it.
Any professional field whereyou are creative, there's a
(05:31):
budget, there's a timeline,there are constraints.
I don't know that theconstraints are wrong.
I think it's the expectationsor the ability to really focus
of what's absolutely mostimportant, what we're actually
trying to do, and included inthat mix having some care of
those creative folks, because aburned out creative is not going
(05:54):
to be very creative.
Constraints are fine.
Reduced resources that happens.
We've all had very creativemoments under reduced resources.
But if the expectations arestill sky high and people are
feeling burned out and not caredfor, that makes it tough to be
very creative.
I think that good leaders aregoing to need to through this
(06:16):
whole moment, remember their ownhumanity, care for their teams,
make their teams feel trustedand cared for.
It's a difficult time, butwe're in it together.
We'll get through it.
Just make sure that I'msupporting all of you to get
through this moment instead ofoperating from fear and being
like hey, the expectations arestill the same.
(06:37):
Keep cranking it out.
Molly McMahon (06:40):
I wanted to talk to you a little bit about design
teams.
You have been one of theleaders in design operations or
design ops, and we're going totalk about this a little bit
later.
But design ops is basicallywhere organizations
operationalize and scale designprocesses and teams to make
design more efficient andeffective.
(07:02):
But I'm curious to know yourthoughts about why so many
design teams and designers werecut by tech companies this year,
particularly when you thinkabout what designers can do,
their ability to do more withless creative problem solvers.
It seemed to be a field thatreally took a lot of heat in the
(07:25):
layoffs that have beenhappening across Silicon Valley.
Courtney Kaplan (07:29):
I feel like there's this belief of as long
as we have engineers, we canbuild it and everything else is
secondary to that, for better orfor worse for the rest of us,
for consumers who have to usethose outputs or those what is
actually shipped.
I think that there's that corebelief, especially out here,
that engineers are the mostimportant and if we can build it
(07:52):
, that's the most importantthing.
Then research, design, contentstrategy, some of these other
roles are really nice to haveand can be super useful, but we
just don't need as many of thosefolks.
We don't know what they do allday.
Then I think that even insophisticated organizations that
can somewhat be the attitude Inorganizations that aren't as
(08:16):
sophisticated certainly theydon't value or feel that they
can't put resources towardsdesign, user experience, content
strategy.
Those things are nice to have.
J.B. Skelton (08:29):
How do designers demonstrate their understanding
of business objectives better?
Courtney Kaplan (08:34):
Yeah, it's interesting I've seen it happen
really well in many cases acrossmy professional experience
where a designer will latch on,usually not to a big, big, big
KPI or a really big problem, butsomething that they can get
their arms around.
That offers a great case studyor a great example of what
(08:55):
design can do They've been ableto put together.
This is what we're trying toachieve and why.
Here's how design could helpthat.
Because I've done some researchand I've unpacked the problem
more deeply than just making thechart go up and to the right,
and so I can represent what'sactually happening and what the
real problem is and how we canchange it, and I've even shown a
(09:17):
couple of solutions that wecould test to see if I'm right.
I might be wrong, but we couldtry it.
Then someone's like we couldtry it.
Then, if you try it, then ifyou're saying, oh wow, this
person has, there's some actualrelevance here.
This makes a lot of sense, thenyou gain trust and I think that
for most designers you'reprobably not gonna understand
(09:37):
the big business capital B,capital, b, big business.
But if there's a feature on aproduct or a specific way that
you see huge inefficiencies,jump in, dig in, articulate it
and tell the story to everybodyyou know Don't assume that they
see the problem the same way youdo and then come up with
(09:58):
solutions and explain how yougot to the solution.
Those kinds of conversationscan be really illuminating and
great practice for designers.
Molly McMahon (10:09):
Yeah, it's interesting because I've been
recently doing work consultingfor product teams and design
teams inside of product teamsand one of the biggest
challenges that I've been seeingis that the design teams really
focus on process or they'relike this is my design process
and this is how weproblem-solving this way, but
(10:31):
sometimes that can be reallyisolating to the product
designers or the productmanagers and the engineering
team because they have adifferent process for problem
solving.
What advice would you give whenyou think about designers today
and thinking about all thesechallenges that they're facing,
and what advice would you givethem for how to work inside of
(10:54):
their current organizations?
Courtney Kaplan (10:58):
One of the things that I tell people right
now is to kind of define what'syour commitment, because right
now people are burned out,they're resigned, they're
resentful, they're angry, right,but they're still pushing
themselves to do great work, andso they're still working late
but they're bitter about it.
Plus, plus, plus.
This kind of builds thisbitterness snowball, if you will
(11:19):
.
And so I say look, step back.
What are you committed to?
Are you committed to getting apromotion?
What's that gonna mean?
Are you committed to being homewith your kid?
What does that mean?
Where is your commitment?
And then be in it with bothfeet because that divided
resentment, but I gotta show up,resignation.
Nothing changes around here,but I gotta be here.
(11:40):
That's not a creative,generative, exciting position to
take.
You're just kind of, you know,hamstringing yourself a little
bit.
You're a little hamstrung toactually take action that's
going to get you anything youwant.
Listen, if you're like look,this is just a terrible time in
the industry, I'm just going toput my head down and do my work
(12:01):
and do my thing and not expectto promotion or not expect
anything specific for the nextcouple of years, because it's
terrible.
At least that's where yourcommitment is and you can sleep
well at night knowing that'swhat you've decided.
But there's a lot more.
There's a lot more you can openup and decide.
What am I committing to rightnow?
J.B. Skelton (12:24):
Let's take a sharp break and when we get back
we'll dig deeper on designoperations with coach and design
leader Courtney Kaplan.
So, courtney, we've all playedMaryfuck kill before with our
friends, but we put a differenttwist on it here at.
On serious, it's a rapid firegame that we call higher fire
boss.
The rules are the same, exceptyou will have to choose one of
(12:47):
the three people on yourfictional list to hire, one to
fire and one to be your boss.
Courtney Kaplan (12:53):
OK.
J.B. Skelton (12:55):
You ready.
Courtney Kaplan (12:56):
Yes.
J.B. Skelton (12:57):
OK, jalo Beyonce or Shakira.
Courtney Kaplan (13:01):
Oh gosh, I would say Jalo hire Beyonce boss
, shakira fire.
J.B. Skelton (13:12):
OK, oh.
Molly McMahon (13:18):
That was fighting words.
I don't know.
I'm a big Shakira fan.
I'm like, oh wow, shakira gotkicked to the curb.
Oh, wow, ok.
J.B. Skelton (13:29):
Molly, do you want to give the next three?
Molly McMahon (13:31):
Oh sure.
Well, Courtney, you have been acoach to some of us here,
including myself, and we werethinking about who in the self
improvement section of theKepler's bookstore would you
want on your team.
So the options are Brene Brown,adam Grant and Dale Carnegie.
Courtney Kaplan (13:59):
I think Brene Brown.
I'm kind of a Brene fan girl.
Adam Grant is great, but Breneso where is she?
J.B. Skelton (14:10):
Where is she?
Is she your boss?
Do you hire her?
Courtney Kaplan (14:13):
Oh she's, I hire her.
J.B. Skelton (14:16):
Congratulations.
Courtney Kaplan (14:17):
And Dale Carnegie fire, because I don't.
I think he's kind of done, youknow what I mean.
And Adam Grant's boss, I think,because he's level headed and
very calm and rational.
I'm.
Molly McMahon (14:30):
Molly, your face still looks like.
It's not cool.
You're like what?
No, no, no, no, I can getbehind that.
I can get behind that.
We were chuckling over DaleCarnegie being tossed in there
with those two as well, daleyeah, he's old school.
J.B. Skelton (14:46):
We were trying to decide Tony Robbins or Dale
Carnegie.
Do you want to hear something?
Courtney Kaplan (14:50):
so earnest and so sadly earnest.
When I was 13 years old I wassuper, super shy, like really
shy, and I could tell I wanted abetter social life and I was
kind of in like the Bible studygirls social group and I read
Dale Carnegie's how to makefriends and influence people.
But because I was 13, Iearnestly put each suggestion to
(15:13):
work.
Wow, and it was really popularin high school.
Okay, one of the things thathappens is an engineer can build
something and it works or itdoes not work.
Right, they kill a bug and theycan check a box or not check a
box.
For a designer, that's just notthe case.
(15:35):
They generally have to connectacross multiple teams, have
research, understand what'sgoing on.
I have a conversation withengineers.
So so much of their job iscommunication, which is fine,
but having design operationshave a way.
Where does this communicationlive?
How do we structure it in a waythat we're having conversations
(15:56):
that move us forward, work inthe next new person that joins,
find these conversations fromthe past and get up to speed
really quickly?
All of those kinds of thingsmake it so that the design team
can actually be effective.
Otherwise they would just be inmeetings all day and, by the
way, a lot of folks that areamazing, incredibly talented
(16:19):
designers might not care for thepolitical hustle of going
around setting hey, let's makeour comms plan.
Hey, let's set up what we'regoing to do for our all hands.
They're not interested in someof the work that goes behind the
scenes to do all of thesedifferent roles that help them
stay robust and healthy.
Molly McMahon (16:37):
Yeah, I always think about design operations
and or design program managementas an opportunity to set
structure, and so I'm curiouswhat your thought is around what
the importance of thatstructure is for catalyzing
creativity and catalyzingproblem solving Right.
Courtney Kaplan (16:53):
Right.
So for anyone to have kind oftheir container for creativity,
having a rhythm of what yourweek is going to look like makes
it's a big help.
Knowing Wednesday is your makerday.
You don't have any meetings onWednesday.
Knowing every Monday you'llmeet with your full team and
have an opportunity to presentif you need to.
Knowing quarterly there's anall hands and there's an
(17:16):
opportunity to finish work andpresent to the larger group.
Knowing what your review cyclesare like, or your design reviews
or your critiques If you knowall those things, you can work
and work freely within thatstructure and container.
But if no one's setting that upin a way that's well designed
itself, you kind of have a getyanked around like oh my God,
(17:36):
critiques today.
Oh my God, we've got to presentto our leads tomorrow.
Wait, we can't present that toour leads, we haven't presented
it to our cross functionalpartners.
It can be really messy andreally churning.
And so, being able to havedesign program managers set up a
logical path or some logicalcheckpoints or some logical ways
that this work can happen, letthat part of your brain relax so
(18:00):
that you can focus on doinggreat design work right, because
someone else is making surethat there's a check-in and
there's next steps available ina predictable place.
Molly McMahon (18:10):
Yeah, I often think about that structure
creating certainty in anambiguous process.
Yes, I love that.
So it's like calms you a littlebit.
You're like, oh, okay.
Well now you have the chance tobe expanded.
I'm not going to be offensivehere, but I can only do it for a
certain amount of time and thenwe're going to have to make a
choice at this moment, and Ithink it's really powerful.
Courtney Kaplan (18:30):
That's right, creating those kind of packets
of those containers of creativetime where you can think how the
discussions, have explorationsand not just be on a constant
hamster wheel of to-dos andmeetings.
Yeah, yeah, but that's aconscious creation, it doesn't
happen naturally.
You have to actually make thoselittle, that design, that
(18:53):
structure, so that you have thatspace to be creative and
thoughtful and connect and havedeeper conversation than
otherwise.
Molly McMahon (19:00):
Yeah, I agree.
J.B. Skelton (19:03):
Now, courtney, I remember this story.
It was in the middle of this.
I think it was the summer of2012.
And I was working with KateAronowitz, who was the head of
design at Facebook, on a clientpresentation to a big European
(19:24):
fashion house that she washelping me on, and she was like
so I came over to her desk on aFriday afternoon and she was
just like we just made thebiggest acquisition I just
closed, the biggest acquisitionthat Facebook has ever made,
which, of course, was theacquisition of Hot Studio.
At the time where you were, andat the time, that was the
(19:47):
single largest acquisition thatFacebook had made.
We went on to spend $23 billionon WhatsApp, but we started
with Hot Studio, and that wasreally the introduction of
design operations to Facebook.
So what are the lessons thatyou have for people that are at
(20:12):
that starting point?
What are the things that youwould absolutely say are
essential and the things thatyou would never do again?
Courtney Kaplan (20:19):
Yeah, I think that things that are absolutely
essential is there are going tobe fans that are excited to hear
about what design operationscan do and the support that's
available.
Work with those people andthere are going to be people who
aren't fans.
They just don't buy it right.
Just stop selling.
You don't need to find.
Let them run their team the waythey want and sooner or later
(20:42):
something will happen andthey'll be like oh well, that
would have been really helpfulto have design ops.
Then you can be gracious andhelp.
But don't try and sell peoplewho aren't ready or who aren't
bought in, because there areplenty of folks that are excited
, they're ready, they're eagerto learn and understand how to
partner, and there's more thanenough work among them, and
there's more than enough work,so for sure, that's one of the
things that I think that'sreally important.
(21:04):
Secondly, I think that a lot ofnew design ops teams myself
included was we were like asmall team of generalists at the
very beginning and we werewilling to do it all right.
Anything you need help with,I'm happy to help.
That wasn't a great strategy.
I think we are still feeling itout to feel where let's do it
(21:25):
all and then see what we'reactually best at or where we add
the most value.
But in that doing it that way,I think it's easy to burn people
out or make people moreconfused about what you're doing
because it's unclear.
So if I had to do that partagain, I would at least start
with a stake in the ground.
So here's what we do.
Here's probably what we don'tdo.
(21:46):
That could change, but for nowhere's what we do.
Pick a major, do well in yourmajor, and then you can always
expand and kind of havedifferent flavors later.
J.B. Skelton (21:56):
I love the way that you put that.
How has managing creativeoperations influenced your own
personal growth?
How has it changed yourperspective on creativity?
Courtney Kaplan (22:10):
There's a lot of pressure to do something new
and amazing and flawless andseamless and frictionless and
all these things.
There's a lot of pressure andthat these designers can be kind
of sensitive souls that needsome TLC and some care.
As a leader realizing it makessense to put in some time to
(22:30):
connect with people as a person,let them know they're cared for
and that they can, you can calmdown.
Keeping people calm and feelinglike it's okay, they're safe
and Safety, then you can becreative and generative.
But if you're worriedconstantly that something bad is
gonna happen or some somethingyou don't know is you know that
(22:53):
you can't expect is gonna happenaround the corner that's not a
great creative place to be.
So if you're a leader and youcan kind of like Keep people
chill, reassured, to be atransparent communicator yeah,
you know, be honest and upfrontand be a trustworthy person that
helps create kind of theenvironment that you're gonna
(23:14):
want to see creatives working,thrive, stay and grow and Tell
their amazing friends to comework for you too.
J.B. Skelton (23:22):
So that's something that comes very
naturally to you, like you areable to, you are, you were able
to and I say this is someone whoworked on your team and you,
you, you show a lot of care, you, you create safe spaces and you
lower the stakes Of projectsand not everything feels like
(23:45):
this do or die situation.
What is your advice to folkswho are, who are in new
management, who may not come by?
That is naturally and asInstinctually as you, you do.
What is your advice to them inways to create that and to
create saver spaces for everyone?
Courtney Kaplan (24:06):
right.
I think for new managers, a lotof times they act out of fear,
right.
Yeah, they just got a new role,they just got that promotion.
They don't want to let anybodydown and they're gonna finally
be able to show everybody thatthey've got some control and
power.
You know, they've got an ounceof power and they're gonna use
it.
So, I think, to be able to notact out of fear, to be able to
trust your team People makemistakes, but you can also work
(24:28):
through mistakes.
There are performance issues,but you can also work through
performance issues, and that'sthe job.
A lot of my clients come to meTalented, amazing people.
They've just gotten theirnewest role and they've hit
their edge right.
I was pretty confident when Iwas the manager.
I was pretty confident when Iwas a manager of managers.
Nah, I'm a director, I don'tknow what the heck I'm doing.
(24:50):
I'm terrified, yeah.
And so when you can admit thatto yourself, say I'm terrified,
then it's time to kind of sayokay, what kind of support do I
need?
You know, what kind of help doI need?
Is it a coach?
Is it a mentor?
Is it a group of peers I trust?
How can I make myself feel moresafe, to create a more safe
space and operate from a senseof care and dignity, not a reign
(25:13):
of terror.
Molly McMahon (25:15):
I love that, and I say that because when you do
move up into leadership roles,it's isolating and you can
really feel like you're shootingfrom the hip or you're alone in
your decisions.
Because, and because it's hardto get time with your, with your
peers, you're also Earningtrust with your peers.
(25:39):
The people who can help andsupport you in that leadership
role tend to be even busier.
Yeah, absolutely.
Courtney Kaplan (25:46):
Absolutely.
I couldn't have said it bettermyself.
It's true, when you're a leader, you are alone, you are
shooting from the hip, you arenavigating really tense
situations on uncertain moments,and then you layer that with
some of the other things thatwe're all experiencing on this
planet and you know politicalscenes plus, plus, plus, all
these Things that kind of piledon everyone's a little bit.
(26:07):
You know fried, yeah, yeah,finding those I call them Stress
management strategies, to havea true strategy that you're
committed to to reduce yourstress.
It's not gonna happen,naturally, it's not gonna become
easier, it's not gonna happenover the weekend.
So, what is your strategy toreduce stress?
(26:27):
You shut your phone off atnight.
Do you Meditate, yoga, run, geta dog, whatever the heck it is,
so that you that you know thestress is a part of my life.
Yeah, it seems like it'sgetting more intense.
I need to actually activelyaddress this and not hope that
it goes away.
I used to do a thing atFacebook that I called meeting
(26:49):
meditation and all I would do isrealize I'm in a meeting room
with people.
I don't need to clench my jaw,that's not helping.
I don't need to hold tension inmy shoulders might they aren't
doing anything.
In this meeting I can actuallyfully relax my body, still pay
attention and participate.
Follow my breath, participate,follow my breath, participate,
(27:13):
and then your body is.
J.B. Skelton (27:15):
Existential life-changing?
Courtney Kaplan (27:21):
Yeah, you don't have to have.
You don't have to hold ameeting with your face like a
scrunched you can.
Physically relax, like go sinkinto those beautiful chairs that
they have Focus on your presentZen out a little too much.
J.B. Skelton (27:37):
No, she says that with a huge smile on her face.
Molly McMahon (27:47):
A little.
J.B. Skelton (27:47):
Colgate glint on a teeth.
I know I was known as a shittydegree.
Molly McMahon (27:56):
When we come back .
Transformational coaching withCourtney Kaplan more and serious
in just a moment.
Courtney, so you and I metbecause I was seeking a
(28:16):
professional coach.
I was also curious to learnmore about design operations and
I was wondering if I shouldbecome a coach myself, and I'm
actually not alone in that.
There is a rise in coachingright now.
The number of professionalcoaches out there has risen 30%
in recent years and there'ssomething like 71,000 coaches
(28:38):
worldwide.
As One of those 71,000 coaches,what's driving this increase in
demand for coaching?
Is there a paradigm shiftthat's happening around what it
means to lead organizationstoday?
I think things are changing sofast Right now.
Courtney Kaplan (28:55):
Things are changing so quickly and you're
expected to kind of like be anexpert in whatever is happening
now, when that's reallydifficult to do.
And someone compared it toprofessional baseball players
practice, and practice andpractice all week long.
They practice spring training,they practice, and then they do
(29:18):
one game a week, right, For acouple hours.
You go to work and you're onthe spot doing it.
There's no practice work, it'sall just doing it, expecting to
hit home runs Left and right.
Molly McMahon (29:32):
That's very hard.
There's no rehearsals.
Courtney Kaplan (29:34):
That's very hard.
There's no rehearsal, there'sno practice.
So I think that bringing incoaches helps shortcut a lot of
the learning cycles that peoplewould otherwise have to go
through, helps people realizeand get more honest with
themselves more quickly, right?
Oh, you know what?
I'm not a good listener.
I've kind of heard that from afew people at work, but I
(29:56):
haven't really taken any actionbecause I don't know what to do.
A coach can help you figure outwhat to do.
Hey, you can do this.
Hey, you can practice this.
Let's do that, let's do this.
That's very useful, and so thattakes.
So, for leaders today that areworking in fast changing
environments less resourcesdependent on their leaders, all
the way down to brand newmanagers to keep things rolling
(30:19):
you want all of those people tobe trained and have some kind of
support, and it's not gonnacome naturally.
And I think also in the oldendays it was easy to kind of ask
the older people at work.
Sometimes now there are noolder people at work, right,
things have changed so much thateither industry is new and it's
(30:40):
a lot of younger folks, or theway that older people did it
isn't as relevant to what youneed to do in your role, right?
I think about it like Iwouldn't be able to ask my dad
how to resolve something overSlack.
It's just not.
It wasn't his world right.
So in a lot of cases things arejust moving so quickly that
(31:04):
that support even making thespace to give yourself the
support, have the conversationsreflect, unpack the problems
that you're having makes a bigdifference.
Molly McMahon (31:16):
Can you talk to us about what transformational
coaching is?
That's your promise at IconicLeadership Coaching.
Can you tell us a little bitabout what it is and how it sets
you apart from other coaches?
Courtney Kaplan (31:32):
Yeah, for sure, I think.
When I talk abouttransformational coaching, I
think there's a radical shiftthat we have a possibility to
make.
That's not far away, but weresist making it because we
think we're gonna have to giveup too much, right?
So, for me, I wanna be a coach,but if I am a coach I'd have to
give up my job and that means Ihave to sell my house and I'd
(31:54):
have to be.
We make it so hard for us tojust do what we want to do, and
so in transformational coachingwith my clients, we make this
space to just let you explorewhat might be possible for your
life, professionally andpersonally and a lot of my
clients are coming forprofessional reasons.
Let's break down some of thestories you've created about why
(32:16):
it can't happen or why it's nothappening, or who's preventing
you from happening, from makingthat happen, and then let's make
a little, have some littleexperiments where you can try a
few things.
Right, If you're like, oh, I'mintroverted, I just don't speak
up in meetings, let's make acommitment just to speak up in a
couple meetings, not the bigones with the CEO, but some
smaller meetings with people youtrust.
(32:37):
Push through some of these oldstories that you've got to see
what might be possible there,right?
And so suddenly, slowly andsurely, I'm moving people from
where they are, square A, tosquare B, C, D, E, whatever,
without the fear and terror ofthat big, huge jump.
(32:59):
I have to make a big, huge leap.
You don't have to make a big,huge leap.
Let's start with someexperiments.
Where do you feel comfortable?
What might be possible, right?
So that allows people to havethat creativity and freedom to
explore things.
So I've had clients that arelike I want a promotion, that's
all I want to do.
I want to get a promotion.
So I'll say listen, let's talkto some of the people that have
that job and see if that's whatyou want to spend your time
(33:22):
doing.
And they've changed their mind.
I don't want a promotion, Iwant to stay in my role.
J.B. Skelton (33:29):
I want to do exactly what.
Courtney Kaplan (33:30):
I'm doing, but I want to do it in a different
way, or I do need more money, orI do want a bigger bonus.
That's fine.
You know a lot of times thepromise of being your best self
or transforming that self.
People get excited about thosepromises, but the truth is that
true transformation comes frompractical ways of being a little
(33:53):
bit different over time,unpacking uncomfortable topics
and understanding them better sothat you can understand
yourself better and make changesin your life.
And so I think that I reallyget excited when I get to work
with clients and help themactually shift the way they show
(34:14):
up at work and at home and thenrealize promotions, new jobs,
moves, new relationships,traveling the world, whatever it
is.
That is a blast to not onlysupports people in what they
want to accomplish, but to seethem accomplish.
It's super fun.
J.B. Skelton (34:39):
Courtney, you are just an incredible design leader
, thought leader, people leader.
You're a coach, you're afounder, you're a writer and now
you're even a teacher.
Where can people keep up withyou online?
Courtney Kaplan (34:55):
You can find me at my website,
iconicleadershipcoachingcom.
You can also find me onSubstack under
iconicleadershipcoaching.
Molly McMahon (35:05):
I do a bi-monthly newsletter twice a month
newsletter which I always sendout to my pals.
I'm always like this is gold,so get on the newsletter.
Courtney Kaplan (35:17):
Love writing that newsletter super fun.
Yeah, those are probably thebest spots.
And, yeah, this fall I'mteaching at California College
of the Arts.
It's a blast.
I just had one class so far.
My class is Communication byDesign.
So excited to get in there.
(35:40):
Yeah.
J.B. Skelton (35:40):
I love it yeah.
Thank you.
Thank you for being a friend,thank you for joining us on
Unserious.
Courtney Kaplan (35:47):
Thanks, Courtney.
Thanks for having me.
This is a ball.
So great to see the three ofyou.
J.B. Skelton (35:52):
You're a star, thank you.
Courtney Kaplan (35:54):
Oh, thank you.
Molly McMahon (35:58):
Oh wow, courtney, really named the complexity.
The plus, plus, plus we are allfacing in our personal and
professional lives and sharingtransformative ways to commit to
ourselves amidst constantchange.
Jb, what were your takeawaysfrom that one?
J.B. Skelton (36:14):
Well, first off, I'm always struck by how
Courtney creates space forhumans to work as humans and
that safety turns just a groupof random people into a very
connected team Totally.
I also was really struck by herstory from Junior High about
saying hello to everybody in thehallways.
(36:36):
It's something that I do tocreate more community and real
warmth and communication amongthe people I work with as well.
Molly McMahon (36:46):
Yeah, I love that too, and I also am taking away
with me the meeting meditation.
I'm definitely writing a stickynote with meeting meditation in
my notebook for my next complexmeeting, yeah.
But additionally, I alsoadmired the radical candor
Courtney shared in asking us tobe honest about addressing our
own areas for growth, beingclear that it's up to us and our
(37:07):
commitment to transform or not.
J.B. Skelton (37:13):
And that's the show.
Unserious is in its firstseason.
Please subscribe, rate us,share it with your friends.
It means so much to a new showlike ours.
Keep tabs on us on our website,Unseriousfun, or find us on
Instagram, also at Unseriousfun.
Special thanks to ourincredible producer, Micah Vonow
(37:36):
, who's had a huge hand inshaping the content and the soul
hand in editing it for us today.
Thank you so much for tuning in.
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