Howardco Interview Series with Katina Rosker

Howardco Interview Series with Katina Rosker

By on Dec 7, 2021 in Interview Series | 0 comments

Join me for this month’s inspiring interview on Leadership where I speak with Katina Rosker (our youngest leader so far to be interviewed!), Managing Director at Milkbar Digital.


If you’d prefer to read this interview, please see the transcript below.


Well, hello and welcome to our
leadership interview series.

I’m Warren Howard and at Howard Co.

We help our clients build sustainable,

high performing organizations
that attract and retain the best people.

Now today I’m going to reflect

on leadership and particularly
with a focus on emerging leaders.

In the past, I’ve asked our guests about

their advice and tips for people
who are new to a leadership role.

Well, today we’re going to be talking

to someone who is in fact an emerging
leader, and they are well-placed to give

us their insight into what it’s
like to being a senior leader for the first time.

Now the business environment we’ve all

been experiencing in the last 18 months
has been challenging,

even for the most experienced senior
leaders amongst us,

because the things we’ve had to work with
and deal with have been unprecedented.

But what if you’re a new leader and you
don’t have those years of experience behind you.

Is approaching things
with a fresh set of eyes an advantage,

since so much of what we’re going through,
we really haven’t been through before.

So today’s guest is someone who I’ve known
for over five years,

and I’ve had the pleasure in seeing her
evolve and grow in both ability

and responsibility into her role today as
the managing director of Milk Bar Digital.

So I’m so looking forward to our
discussion, and I have great pleasure

in welcoming Katina Rosker
to our interview today.

Hi, Katina, how are you?
Good, thank you.

I’m really looking forward
to our chat today.

Well, me as well, Katrina, as I said,
I’ve known you for over five years now.

It’s been such a thrill to be
working with you and the team at Milk Bar Digital,

and so I’m really, really looking forward
to having this interview and this

conversation where we can
share what you’ve learned and

some of your thoughts about
being a new leader in your role.

So let’s ask you

a brief overview of your career and your

background to Milk Bar and what
brings you to where you are today.

So I’ve been at Milk Bar Digital
for just over five years now.

When I first joined Milk Bar,
it was quite a small team.

So that was Sam, who is our founder
and director and two other people, two days a week.

I joined the team and started off part time as well, and I was a social media coordinator.

So I essentially helped out some clients with whatever they really
needed across their social media channels.

And sort of over the years,

that role developed into being a social
media manager, and I started looking after

my own team, which was very nerve
wracking, but also very exciting.

So that was my first time managing.

I was in that position
for about two years.

And then probably just over a year ago,

I started the very exciting role
of managing director Milk Bar.

So a bit of a transition
and a shift for me.

So no longer taking care of my own clients,

which I had been doing
for four years so, a big change.

And I’m mainly taking care of an immediate

team, the team as a whole,
new business development,

a lot of strategy work and basically
whatever anyone else needs a hand with.

So it’s a very varied role,
no two days look the same.

And I guess prior to Milk Bar,

I had a small contract role at a social
media agency for a few months.

And pretty much before then it
was all just Uni and internships.

So I had a lot of internships in my final
couple of years at Uni,

and thats when I really discovered
the world of social media,

and that’s when I realized
that’s where I wanted to head.

Well, thanks Katina.

Let me ask, a couple of quick questions there
based on all of that wonderful information

when you started you said what, there was three or four in the team?


How many today?

Officially as
of today, we had a new starter, officially 21.


So from 4 to 21

Over what period of time?

About five years.

About five years.
So that’s pretty rapid growth, isn’t it?

It’s a great time to be on board.

And of course, that that growth has

mirrored the explosion
in social media over the time.


It has really, really grown.

When I was at uni,
it wasn’t part of the curriculum.

It just didn’t exist, really.

I think I had
one unit at Uni, that was called digital

marketing, but they never even
touched on this concern.

So I’m sure its very different these days.

Well, that really is very,

very different. I imagine back then would
it have been Facebook

the only sort of social media platform
that people were talking about?

Yeah, pretty much.

I think Instagram was new when it
came to businesses being on there.

I think it was there for your personal

use, but it’s definitely
really taken off now.

Well, exciting time to be on board.

And obviously you must be doing a good job
because you don’t get to 21 people unless

people like what you’re doing and there’s
more demand for your services.

So fantastic.

I know there’s a lot more story behind all

of that, and I’m sure we’re going
to dig a bit deeper as we go into.

The next questions,
but let’s reflect on your experience,

particularly over the last 18 months,
as they have been challenging times.

What three words would you use to describe
your own personal experience as a leader?


During the last 18 months,
I think the first would be ever changing.

I think, you know, no two
days are really the same.

You didn’t know it was around the corner.

And I think because of that as well,
it was a little bit scary.

The unknown,
you know, just not knowing where things

would head, what’s next
week even look like.

But I think overall as well,
it’s also been a very rewarding year.

I think it’s been particularly
a big year of growth for Milk Bar.

And I think we’ve been one
of the lucky businesses during COVID.

So yeah, I think I’d probably pick
scary, ever-changing and rewarding.

How have you grown as a person,

Katina as the, you know, apart
from the responsibilities of the role?


What have you learned about
yourself in that time?

If I was looking back at myself 18 months
ago, I probably would have been very

scared like I mentioned,
just not really knowing what was ahead.

I’m a lot more resilient
than I probably thought,

able to think on my feet more
than I thought I could too.

I’m someone who’s very process and yeah,
anything to do with systems and whatever

can be organized is sort
of my default way of thinking.

So that’s been a bit of a challenge,

but I think I’ve learnt that I can do
whatever is needed on the fly,

even though I might be
a bit hard sometimes.

And I think that’s probably like a big
part of my growth in the last years.

Having to adapt to that kind of mindset
and that way of working.

Great answer Katrina, resilience is certainly something

that we’ve all had to learn
if we didn’t have it already.

And the other thing you talked about
being adaptable and agile, you know,

being able to move with the times
and adjust your style,

adjust the way you’re going about managing
so, you know, resilience and agility.

I think two very positive outcomes
of our experiences in the last 18 months.

So well done.
Thank you for asking that question.

That was a bit of an impromptu one, but
I knew you’d answer it well, thank you.

What are some of the challenges

that you’ve experienced in your new role,
particularly something perhaps you weren’t expecting?

Theres kind of two that come to mind,

one of them is probably just the best way
to make decisions,

and I think that was a big part of what I
was concerned about. I guess stepping

into this new role,
like how do I make the right decision? How

do I make sure it’s right for everyone
involved? How do I make sure I’m not

taking too long because obviously some
decisions have to be made quite quickly?

And I knew that going into it.

But then when you’re kind of in it
for real, when you have a lot of things

going on at the same time,
it can be a tough one.

So I think yeah, making decisions and you

know, it’s different when you’re working
on your own clients and things that you’re

across every single day because
you’ve got all the information.

But whereas with a team member,

they might come to you and you might have
to make decisions, but you might not have

all the facts, and you might have to spend
a bit of time looking into it and trying

to figure out what’s the best thing for
the team member as a whole or for the client.

So that’s been a bit of a challenge.

to try to navigate.

And I think with decision making too,
everything is always new,

so you can’t really default on a past
process that you might have had in place

because there’s no such thing as
the same problem, kind of twice.

So that’s been a bit of a challenge.

And then I’d say the other one
is probably time management.

I think that’s a big one because when

you’re in a leadership role,
you of course have your own

responsibilities and things
that you have to tick off.

And you know, you might go into tomorrow
thinking, I’ve got the whole day

to literally do admin and I can
have no meetings.

It’s looking like a lot of desk time.
It looks great.

And then all of a sudden you get

in and there’s a lot of things
that suddenly need your attention and you

have to kind of really shift your mindset
and move things around because you

obviously don’t want to be a bottleneck
and hold things up for people.

But then if you’re moving your things

to the other side, it’s like,
when are you going to have time for that?

So that’s been definitely a bit

of a challenge, trying to
move things around and try to find time

for my own things versus
whatever the team needs.

So that’s been a bit
of an interesting one as well.

Thanks, Katina.
I’m sure many people will relate

to exactly what you were
talking about there.

You know, first of all,

the ever changing nature of making
decisions, no two decisions are the same.

But the other thing is about

the the constant demands on your time
and having to set priorities.

And with all those competing interests,

whether it be customers,
other stakeholders, your team,

the business owner,
there’s a lot of juggling that has to go

on in a day to actually get the important
things done and making sure that you’re

doing that, the important not
just the urgent ones as well.

Okay, some really great insights.
Thank you.

What about the flip side of this?

What would have been the rewards of being

a new managing director?
Theres been heaps.

Yeah, I think a lot of the time when you
can reflect, you might think about

the challenges and that sort of thing,
but I feel like I’ve been able to have

a look at a lot of the positives
and a lot of the rewards.

And I think

particularly for me,
a lot comes down to where Milk Bar first started

and where I was in my journey
and where Milk Bar was five years ago.

So I guess to to see
Milk Bar where it is now.

It’s really nice knowing I’ve played a bit

of a part in that and I feel like
a piece of the furniture, really.

So yeah, for me, a lot of the rewards are
based off,

I guess, training new team members,
seeing where they end up,

whether that’s progression for them
internally at Milk Bar or it’s seeing them

move on to somewhere amazing and then
being able to bring all those skills

and things that I’ve
personally helped train them with.

And I find that that’s been great.

And I think that some other advantages or
other rewards this year has again just

been the growth, but particularly in terms
of the project side of our business.

So we’ve started doing a lot of project
work, which never really was a thing

for us a few years ago, and it’s
really great to see that happen

and I think a big one
too moving into this role,

I never expected it,

I guess this early on in my career,

I never thought that this would be
where I’d be five years down the track.

So I think a massive reward of it is
really how much Sam,

the founder of Milk Bar,
also trust me to be in this role so

that in itself is probably one
of the biggest rewards, I think.

And Sam, I’m sure, would agree with all
of that, and I know Sam very well also.

So look what you said,
that was really interesting and made me

think about, you know,
the nature of your industry.

As we said, it’s, you know,
it’s quite a young industry and therefore

it’s a it’s an industry
for younger people.

It’s, you know, it’s definitely
a younger generation industry.

And for Milk Bar, you know,
it’s been for some of your and probably

many of your team, a starting point
for their career, which is just terrific.

And it was really nice to hear how you how

you look at that role that you play
in developing up people and even if they

end up leaving that you’ve added to their
career development and their future.

And I think, you know, we know
that people are looking in that for jobs.

They want a good place to work somewhere

with a purpose where they
can make a contribution.

But people do want to grow.

They want to develop their
skills at the same time.

You’re obviously doing that well, well done.

Next question. Can you tell us about your

own approach to leadership
now as you have developed it?

And also who or what has
inspired you in your career?

perhaps in some of the more

challenging times when you may
have even doubted yourself?

Yeah, that’s a great question.

I think in terms of my overall leadership

approach, I think I’m quite collaborative
and I like to think nurturing as well.

I kind of see myself as someone who loves
really working closely with the team.

So whether that’s my direct team or anyone
at Milk Bar, I love the training aspect.

I love really helping people up
skill, helping people problem solve.

I love being in that team
environment as well.

And then I think whenever I do have
to make those decisions whenever possible,

I love really being able to consult
with other people to try to get a few

opinions like feel like I’m
really covering all bases.

Really, I think I’m also

a bit nurturing in the way where I like
to kind of like, think the best of people.

And, you know, if someone might
skip out on something,

it’s not necessarily like a finger wagging
moment or anything like that,

but it’s like, Oh, like,
is this something I actually could have

done to help support them? Like,
what’s that extra bit of training

that I need to do to make sure
this doesn’t happen again?

And then I’m also quite process
driven, like I mentioned.

So sometimes that’s in the mix a little

bit too. I guess, in terms
of who or what has inspired me.

Definitely, Sam.

I think from day one being at Milk Bar,

I’ve always found the way
that Sam leads and manages.

I’ve always found that really inspiring.

She struck the balance of being someone
that you can have a great relationship

with at work, but also feel
a really good personal connection with.

And I feel like that’s always been

a management style that I’ve
wanted to pick up myself.

I think that you can still have
a successful business and a team

that respects you and works towards goals,
but you don’t always have to necessarily

be someone who’s very strict
or that type of thing.

So I think that’s something I always
try to remember in my own style.

And obviously there’s times
to be more assertive.

But overall,
yeah, I feel like Sam’s really inspired

me, and that’s definitely impacted
how I like to manage or lead.

And in terms of, yeah,
what’s inspired me during challenging

times or what’s
helped when I’ve doubted of myself? I guess

just talking to others getting, you know,
some reassurance,

you’re doing the right thing or little
bits of feedback even from the team.

And could even just be like really
small things that people mention and kind

of just gives you a little
bit of a tap on the back.

I know I’m doing all right

and I think, yeah, it’s like every day is
a new day, a day to try something new.


yeah, I think especially in the last year,

it’s like a lot of the time has been
challenging, not even just because

of the pandemic and everything
but moving into this new role.

So I think it was almost just a case

of needing a few months to really find
my feet and everything like that as well.


Thanks, Katina.

You know, I mean,

everyone is inspired by somebody or some
event in their life,

and we learn things both
positive and negative, don’t we?

From from people we’ve worked
with and situations we’ve had to face?

And look, it’s really, you know,
it’s really lovely to hear what

what you’ve gained from working
with Sam as well.

I agree with all of that.

But here’s the interesting thing, while
you’ve been watching and observing Sam,

others have been watching
and observing you.

So, you know, as you said,

being a leader is also
being that inspiration for others.

And I really like what you
said about your coaching role

leader as coach is a really,

really important attribute for, you know,
leaders of today and everyone’s a leader.

Everyone has the potential to be a leader

and everyone has the potential
to influence and help others grow.

Here’s the last question.

Well no its’s actually the second last.


If you hadn’t chosen this career, you said

before, you’re not sure what you would
have been doing. But what do you think you

might have been doing right now if
you hadn’t got into social media?

I feel like if you’d asked me five years
ago, like before I started at Milk Bar,

I probably would have had
a much different answer to now.

I think before this, this job,
I probably would have…

I don’t know.
I might have even wanted to go into like

graphic design or maybe a different
part of digital marketing.

I think things like

SEO and that kind of thing always
kind of tickled my fancy as well.

But yeah, now that I’m I’m here and
I’ve I’ve obviously learnt everything.

I feel a really interesting part

that I’ve learned about myself is how much
I love to manage

or how much I love to organize or,
yeah, take care of processes.

So I don’t know what that would look like,

but I think, yeah, if I had these skills
five years ago,

I think I could potentially have
gone down a different path.

Yeah, it’s interesting, I don’t know,
but it’s interesting because

my whole job now, the part that I probably
enjoy the most, is the management

and like the leadership sort
of aspect, but the process is always

there. So I’m like, what can
you give me and what can I organize?

You know, I think that’s a really,
really good thing to reflect

on for many people these days,
because sometimes it’s difficult to try

and project forward what your career might
look like or even what job you might be

doing, given the jobs seem
to be changing so rapidly.

What’s more important isn’t it is

to actually think about what
are the things I’m good at?

What do I like doing

and how can I apply those in my career?
Because that way

you open up a lot more options to
yourself, for your self-growth.

So it’s really good, you know, really,

really good sound information
and advice there.

All right.
Here’s the last one.

This is really the last one.

Knowing what you know now,

what advice would you give to your younger
self about how to approach your career?

I feel like for me personally,

it’s interesting because, and we sort of touched on it, and it’s like,

I didn’t think a place like this
existed when I was studying.

So it’s not something that I could have

dreamt of if that makes sense,
because it wasn’t there.

I’ve always been a really big advocate of
internships like I know that’s a thing

that I will always pass
on and talk to people about.

I think I’d definitely pass that advice
on to my younger self again.

It kind of connects with the idea of just

wanting to be a sponge and soaking
up as much as you can.

So from anyone at uni that you
feel like is doing a great job.

People at an internship, a tutor, managers, anyone.

And it could even be like pulling out tips

and tricks from jobs that aren’t actually
related to what you want to actually do.

But you might have a retail job that you

did when you were in high school,
but you can still pull out some skills or

pull out some key learnings
from different situations.

So I think just being a sponge as much as

possible is probably something, and I think
a part of the internship thing as well

is just trying things out,
because when you’re in uni,

you might have an ideal career in mind
and you might have an internship

and realise, hey, this isn’t actually
anything that tickles my fancy.

I don’t actually think
I want a career here.

Let me try something else
instead at another internship.

And I think internships themselves,
you can just open a lot of doors,

whether that is
a potential job offer or is the connection

that you can have
and that kind of thing too.

I think probably another thing for me

that I probably would tell myself because
I know, especially years ago,

I was a lot more more strictly
like process or goal driven.

And I think that while that’s great,
it’s not always practical.

So I think just reminding myself that,

you know, it’s OK to go
with the flow or trust your gut,

live in the moment sometimes because,
yeah, it doesn’t really matter.

As long as you’re putting your best foot
forward, you’re probably going to keep

learning and get to the spot
that you want to anyway.

Wise words,

very wise words.

There’s a little piece of the jigsaw here
that I thought we probably should add back

in just for people who were
listening, who don’t possibly know

the full scenario here
because we’ve mentioned Sam.

Yes, sound of the business.

We know you are now the managing director.

Probably, what we haven’t really covered off on is

what were the circumstances
that lead Sam Sidney,

to hand over responsibility for running
the business to Katina Rosker?

Yes, that is true.

Let’s explain that.


I guess like to even
backpedal a bit from there.

When I joined Milk Bar, I always sort
of knew that it was somewhere special.

It was something that I felt really
hungry for, I guess from day one.

And I kind of knew early on and I was

like, wow, I was like,
Milk Bar is going somewhere.

It’s so exciting.

And from, I think even like six months in,
I was already saying to Sam my like,

I’d love to put my hand up like,
I really want to help.

Like, what can I do?

How can I help?

And I wasn’t even thinking about
the next step or anything like that.

I was literally just like
Sam’s doing everything.

What can I do?

So I think that’s kind of been my attitude

since day one, and I think that’s probably
helped my progression to this point.

I guess the real transition
into this exact role was I was that social

media manager for a couple of years and
I feel more recently to

getting this new position,

I started helping out with some
other things around the business.

So whether that was new business
development or putting together pitches

and talking to potential
clients and all that.

I started doing a lot more of that,
and in my previous performance review,

I remember Sam saying something like,
Oh, you know, in the future,

can you imagine yourself in
a kind of role where you’re taking care

of my clients and you maybe helping me out
with more of the business side of things?

I was like, Yeah, that sounds good.

Maybe in the next like three to four
years or something like that.

And then fast forward, turns out Sam is
going to be going on maternity leave.

So that was all basically incredibly fast

forwarded a lot earlier than
I think we both anticipated.

So, yeah, it was basically a chat of,
Hey, do you want to try this new rollout?

And I said, Yes, so

here we are.

So yeah, it was definitely
a challenging transition as well.

Obviously, Sam getting ready
to go on maternity leave as well.

So it made handover not as

straightforward or I guess as process
driven has been probably both wanted.


So that probably made it a little bit more
challenging, but also exciting as well.

Thanks, Katina.
I really wanted to sort of join the dots

there for everyone because you
know that it is not obvious to everyone.

But can I just say thank you very much.

I’ve really enjoyed listening to your

insights and your learnings from from your
career, your wonderful career so far.

It’s been an honor to have been part
of that as a coach to yourself

and to the business and to see
the growth that you’ve all experienced.


For me, it’s very,
very rewarding and satisfying.

I’ve learned a lot from you as well

and I would hope that anyone who’s
listening to this has also, you know,

really taking something on board,
whether you are that person who is new

into a leadership role and now hearing it
from someone else’s perspective,

or perhaps like Katina was
earlier in her career as someone

who aspired to this role but was
looking for the opportunity.

There’s been a lot in this
conversation for everyone.

There’s also something in it for business

owners as well for you to reflect on what
would happen if you wanted to step out

of the business. Needed to, wanted to.
Who would run the business for you?

And do you have someone in the pipeline

who you’re developing and growing
to be able to do that?

Succession planning is such an important
role for any business owner to think about

who would run the business if
I didn’t want to or couldn’t.

And maybe a bigger question,
could they do it better?

I’ll leave you with that thought.

Katina, thanks so much.

You’ve been a delight, as always.

Fantastic answers.

I’m sure people are going to get
a lot out of this interview.

I hope you enjoyed it as well.
Oh, I did.

Thank you so much Warren .

It’s been great and thank you
for all your help over the years.

I just wouldn’t be here with all this
wisdom and with all these ideas,

if not for your help as well.

Thats wonderful Katina. Thanks so much.
See you soon.


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