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September 26, 2025 52 mins
Tonight on The Brian Crombie Hour, Brian interviews Kirsten Eastwood. Kirsten is the President of Dress for Success Toronto and leads a charity dedicated to empowering women through work attire, career development tools, and a strong support network. She highlights the role of clothing in balancing authenticity with professional expectations during interviews and at work. Dress for Success focuses on women facing systemic barriers, addressing high unemployment rates among young women aged 18-29 by building confidence and networking skills. Kirsten stresses LinkedIn, research, clear goals, and gratitude as key to effective networking. She shares Yodi’s journey from persecution in South America to success at Legal Aid, inspiring the upcoming Beyond the Suit fundraiser on October 8.
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Episode Transcript

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Speaker 1 (00:00):
The views expressed in the following program are those of
the participants and do not necessarily reflect the views of
Saga nine sixty am or its management.

Speaker 2 (00:18):
Good evening, everyone, and welcome to the Brian Crombie Radio
are I've got Kirston Eastwood with us tonight. She is
the president of Dress for Success Toronto. What a fascinating
title name for an organization.

Speaker 3 (00:30):
I'm looking forward to hearing all about it.

Speaker 2 (00:33):
She's going to talk to us tonight about not for
profits and charitable organizations and the challenge of raising money
for not for profit and charitable organizations. You know today,
I think the Fall is number one a season where
there's a lot of events and a lot of.

Speaker 4 (00:47):
Fundraising, but it's probably pretty challenging today because of the
economic situation, because of competition from a lot of other
you know, charities and not for profits and just you know,
inflation and all the economic you know reality that we're
all in.

Speaker 2 (01:00):
And frankly, probably that at the same time as you know,
some of us are feeling stressed because of the economic situation.
They're not for profit sector.

Speaker 3 (01:08):
Probably needs money even more than it may have in
the past because of increased need.

Speaker 2 (01:13):
So we're going to talk a little bit about raising
money and the challenge that they're not for profit sector has,
and we're also going to talk about Dress for Success
Toronto and what it's all about. So Kristen Eastwood, President
of Dress for Success Toronto, welcome to the show.

Speaker 5 (01:29):
Thank you so much, Brian. It's my pleasure to be here.
I'm looking forward to our conversation.

Speaker 2 (01:33):
So to start with, tell us what the heck is
is Dressed for Success Ranto.

Speaker 3 (01:38):
You're a charity and what's your mission?

Speaker 5 (01:41):
So our mission is to move women to economic independence.
And we are actually part of an affiliate organization, So
we have about one hundred and thirty affiliates across the world.
There's thirteen in Canada, but we all function as our
own standalone charity and so our mandate is to provide
services to women in the city of Toronto. And every

(02:01):
affiliate has a core program called the Suiting Program. And
so we're probably best known as our name in fers
for providing clothing to women who need it to go
for job interviews or to go back to work. But
we looked at our mission and said, a great jacket
won't get you a job, and so how do we
really develop the programs that women need to become job ready,

(02:24):
and so we transformed a lot of our programs and services.
We still have the clothing program and women can come
and access an outfit to be able to wear for work,
but we also have career specialists who meet with clients
to talk about things like their LinkedIn profile and resumes.
They help them to look at their LinkedIn profile, but
they also help them with things like networking, because I

(02:46):
think we all talk about networking, but it's kind of
a scary thing to do, and so we really provide
women with that safe space to be able to practice
those skills. And over the past couple of months, we've
realized that we're not content just moving women to be
job ready. We want to move women to good jobs,
and so our focus now is on creating that pipeline

(03:06):
with a lot of our corporate partners and looking at
some funding to be able to move women from being ready,
which is what we do to actually finding them jobs,
good meaningful jobs. In the city of Toronto.

Speaker 3 (03:19):
Is having the right jacket really important?

Speaker 5 (03:22):
It can be. It depends on the work environment that
you're in. We're actually doing a lot of thinking right
now about the impact of clothing, because we've heard a
lot from our clients about what clothing means when they
go into an interview. We have clients you still look
at that old sort of expectation of wearing a little
black suit when you're going into a job interview, and
that really doesn't apply very much anymore, perhaps in some

(03:45):
more traditional environments like banking, But we want our clients
to be their authentic selves, to show up as themselves.
We have a lot of clients who are newcomers, and
so we want to make sure that they feel that
they can honor their religious traditions, their cultural traditions as
well too. And we also work with women who identify
as being gender fluid, and so we want them also

(04:07):
to find clothing that makes them feel great about themselves.
So it really is what the clothing can do to
make you feel confident. And so when you go into
that job interview, you know the skills, you have the
right background, your resume looks great, and you feel great
about yourself, and so when you're sitting there in the
interview chair, you're much more likely to be confident. And

(04:28):
that's really part of what the clothing does.

Speaker 2 (04:30):
So I had a person coming for a job interview,
but two weeks ago in a T shirt and a hoodie.
Should I have been negatively impacted by that or not?
I think it depends on probably being their authentic self.

Speaker 5 (04:44):
Yeah, I think it depends on the job. So I
think we have to look at how do we balance
that authenticity with what the expectations are of the workplace.
We're actually doing a number of sessions this fall working
with corporations to talk about decoding the dress code. I mean,
what does dress code really mean anymore? After pandemic, everyone
was wearing hoodies and T shirts and they were doing

(05:06):
a zoom call. And then now people are coming back
into the office as they are with a lot of
the banks and the ops, and people are trying to
figure out what does that look like now? And so
are clothing dress codes? Are they changing? Are they shifting?
Are companies being more rigorous about it? Are they focused
on the kind of client facing roles that they want

(05:27):
people to be dressing for, or are people dressing for
the job that they want? So I think it depends
if someone came in and had an interview with you
and that was an appropriate outfit to wear for the work.
But if you want this person to be facing your
clients and representing you in your brand, that may not
be the image that you want to portray. So it's
a little bit nuanced, but certainly that's work we do

(05:48):
with our clients is the clothing helps them to be
fully I guess connected, and have a sense of belonging
to an organization that they're joining.

Speaker 3 (05:58):
I had a man once that told me that you
should dress for the job you want to get promoted to,
not for the job that you currently have.

Speaker 5 (06:07):
Yeah, I agree with that. I agree. I think it's
just that how do you make sure that you're looking
at where you want to go. It's kind of like
the gret Ski quote as well too, about skating to
the puck. How do you make sure that you're going
in the direction of what you want your career to be?
And there are expectations in certain workforces. I know that

(06:28):
when I used to work in banking, there was a
long list of things that you could and could not wear,
and people were sent home if they were not wearing
the appropriate clothing. I'm not sure that happens anymore, but
I think that organizations want people to come and work
for them wearing clothing that reflects their brand, reflects how
they want to present themselves to the world, and a
lot of times our clients who are newcomers don't understand that,

(06:52):
and so that's a big part of our work was
we want them to fit in, we want them to
be part of an organization, but at the same time,
we want them to be comfortable being themselves, whatever that
might look like.

Speaker 3 (07:04):
I want to I want to pressure you again on this.

Speaker 2 (07:06):
So I had someone else tell me that if you
feel more comfortable wearing a suit and a jacket and
a tie.

Speaker 3 (07:11):
Then wear the suit jacket a tie.

Speaker 2 (07:13):
And if you feel far more relaxed dressing comfortable and
you don't want to be in a relaxed situation because
you want to be confident and you want to, you know,
present your put your best friot forward, put on that suit,
jacket and tie.

Speaker 3 (07:26):
What do you think about that?

Speaker 5 (07:27):
I think it depends on what you're doing. For example,
we did a networking event with a company, and our
clients and our staff all showed up dressed for a
networking event. And the person who was the HR had
there had told her team, who typically come into the
office in jeans and hoodies that they had to get
dressed up. And so I think it depends on the situation.

(07:48):
Perhaps jeans and hoodie or something that that's an informal
attire is fine if you're going to be, you know,
working in an environment where you're on the floor and
you're and you're doing some work in connecting cables underneath
your desk or you or you're doing some heads down
work on a proposal or a grant application. But if

(08:09):
I'm going to see someone about a proposal or a partnership,
then I'm looking at what their expectation might be of
that conversation. And if it's someone who's in a more
traditional business line, then I'm going to be thinking about
that as well too.

Speaker 2 (08:26):
You also mentioned, you know, unemployment, and the unemployment levels are.

Speaker 3 (08:32):
Like, you know, fifteen to seventeen percent for young people today.

Speaker 2 (08:34):
They're in some in some segments like twenty five percent
for new immigrants and people of color, et cetera.

Speaker 3 (08:44):
You focus on females only, Why only females.

Speaker 5 (08:48):
We used to work with both men and women, but
because we're part of this affiliate program and our core
mandate is to support women, that's where we focused on
over the past sixteen years since we've since we've been
in Toronto, and I think that for some of that,
it's that we have expertise that's very much aligned with
women's economic development. That's what my team brings. And women

(09:12):
approach work differently than men do. They bring different kinds
of systemic barriers with them. We have clients who've experienced
domestic abuse, who've experienced all kinds of isms in the
workplace and in life. They have children, they might be
single parents, and so we tailor our programs to support
their needs. And so it's a very holistic approach. So

(09:35):
if someone identifies as a woman, then we will provide
service to them. And we have a very broad definition
of women on our website, and so we do work
with a range of people who aren't necessarily, you know,
white middle class women who come to see us. We
certainly have our very diverse range of people that we

(09:55):
work with. There are organizations who certainly provide those supports
to men as well. Too.

Speaker 3 (10:00):
Are unemployment levels between women and men similar?

Speaker 5 (10:06):
That's a good question. I think it probably depends on
the demographic young people, and this is an age group
that we've just started to work with women eighteen to
twenty nine. We find that a lot of our clients
are very well educated, but the challenge for them is
that confidence in applying for jobs that they may or
may not be fully qualified for. So I'm sure you've

(10:26):
heard this before, but a woman will make sure that
she's got eighty five percent or ninety percent of the
skills that they're looking for before she will apply, whereas
a man might look at having a third or fifty
percent and apply for the job. And so I think
part of it is a different level of confidence. It's
also different approaches to networking, and many of our clients

(10:47):
don't have the kind of networks that other people have,
male or female. If they've been living in Canada and
have established connections to different community organizations, to different organizations
in their neighborhood, that they'd be part of a community
for a long time. So I think that the job
employment levels, it probably depends because a woman might have

(11:08):
to say I can only work part time because I
need to look after my children. But I would suspect
that there are very high levels for both men and
women under twenty nine, and that it probably depends on
the field as well too. Most of our clients come
here with credentials in engineering or healthcare, and so they're

(11:29):
highly qualified, but they also can't work here because they
don't have that credential lets them be a nurse that
they were in the Philippines, for example. We also have
clients who'll come here and leave their families behind so
that they can earn a living and then send money
back for them and the hope their family can join
them too. So there's just different complexities when it comes

(11:50):
to working with our clients. And as I said, I
think what we've learned in the nonprofit sector is that
we can't be everything to everyone. That we do need
to be a bit more specialized and focused so that
we can be much more supportive of those women who
come to us.

Speaker 2 (12:06):
We'rech I tonight with Kirstin Eastwood. She's the president of
Dress for Success Toronto, a charity whose mission is to
empower women to achieve economic independence by providing them with
a network of support, work at tire and career development tools.
We're talking about the not for profit section as sector
as well, and I think we're going to touch on
unemployment and whether the need for the services that Kirsten's

(12:28):
organization provides is increasing because I think it probably is
fairly dramatically. Going to take break though for some messages
and be back in just two minutes talking about Dress
for Success Toronto. Stay with us. Back into.

Speaker 1 (12:44):
Stream US live at SAGA nine am dot CA.

Speaker 2 (12:59):
Welcome back everyone, the Brian Crombie Radio Hour. Kirsten Eastwood,
the president of Dress for Success Toronto, is with us
tonight and we're talking about dressing for success and whether
what you wear is important. I always was told that
a suit makes a man or something like that, and
so I got to believe that how you dress as
a female probably is critically important as well.

Speaker 3 (13:21):
We chat a little bit about that.

Speaker 2 (13:22):
It seems like you've really focused on being authentic and comfortable.
I think you still got to dress what you need
to dress in to look successful, look confident, and feel
confident yourself. And maybe there's a happy medium between that.
But let me turn if I could, to the need.
I had a career counselor text me saying that, and

(13:43):
I've interviewed him before on my radio show and saying
we got to do a show because he says he
has an ever in his career been inundated by as
many resumes. He says, layoffs Brian or rampant. You may
not have heard it yet, but they're rampant. And people
are really worried about their jobs and want to send
out resumes. And this is a big issue. I mentioned
in the last section that I did a show with
some people that were saying that youth unemployment is the

(14:06):
third highest it's been in the last twenty five years,
and that in some of those segments of society, I
think some of the ones that you were talking about, immigrants, colored,
non non white sectors, et cetera, it's as high as
twenty five percent. One in four people are unemployed. Is
the need up? Are there is unemployment? You know, unemployment

(14:28):
statistics that we see are up, but they're all sort
of historical.

Speaker 3 (14:32):
Looking.

Speaker 2 (14:32):
What's your sense of people calling your organization for help?
Is there a lot of fear out there? There's a
lot of concern out there is need up?

Speaker 5 (14:41):
Yeah, the need is definitely up, and there is fear,
there's anxiety. I think there's also a sense of impact
on mental health because it's very dispariting looking for a job.
I mean, we've all been there where you apply and
you may or may have got a call back, and
then if you get an interview, you may or may
not get the job. And the whole process is very

(15:03):
very discouraging, and so the mental health implications are very
very difficult, and that's part of the work that we
do as we bring women in so that they can
share with each other, they could share with their career
specialists and feel that they're not the only ones there.
If you look at people who are in there in
their twenties, they had part of their early career, perhaps

(15:23):
in COVID, living on their own, living in a hybrid situation.
A lot of them have not been in a workplace
on a full time basis ever, and so understanding the
norms and behaviors and how do you perform in that
workplace are also very difficult for them. And there's a
strong sense of social isolation. I mean, this is something
that the Toronto Foundation highlighted a couple of years ago

(15:44):
as being a growing issue and impact on the economy
for people who were experiencing true feelings of overwhelm and
burnout as well. So I think all of those are
things that we're seeing manifesting in the clients who come
to us. They might be able to hide it, but
when they start talking about the fact that they've applied

(16:05):
to one hundred, two hundred and three hundred jobs and
not had one callback, not have one interview, it's very
hard to be able to get yourself back up into
the game of applying for jobs. And a lot of
people do what we have traditionally done is that you
see a job, maybe on LinkedIn, you submit your resume,

(16:26):
you submit your cover letter, you make sure your LinkedIn
profile looks good, and then you wait. And the reality
is that for a lot of those jobs, they may
already have been filled internally and there's no requirement now
there will be in January for employers to contact you
if you've come for an interview. And so people are

(16:48):
navigating this minefield of an employment landscape with a lot
of difficulty, and many of our clients just don't know
how to respond, They don't know what to do. They
keep on sending in resume after resume me and the
whole part about networking is something that's very difficult for them.
They think that networking is going and talking to someone
and asking for a job, but it's building those connections

(17:10):
knowing it takes time and for a lot of our clients,
they don't have the time because they've got to put
food on the table, they've got to pay rent, and
many of them don't have a lot of resources. Here,
we have a client who came from Sri Lanka with
three hundred dollars in her pocket and so her sense
of urgency about getting a job and being able to
cover her basic costs was enormous. The good news is

(17:33):
that after a few years of coming to see us
and working with other community organizations, she is working now.
Her family's still in Sri Lanka, and so that's the
tough part for her is that she's working now, but
she's missing out in a lot other parts of her life,
and that's her reality. Her economic situation is better than
it was when she was at home, but she's highly

(17:54):
trained and not doing the work she was trained for.
So she's that's.

Speaker 2 (17:57):
Slight a different issue because that's how we, you know,
integrate people into our society and how we engage with
immigrants and give them opportunities. But just generally, networking is
pretty critical, is it not, And what advice do you
provide people on networking? As an example, this career coach
said that the person that emailed him said, you know,

(18:18):
I didn't listen to your advice about networking before I
needed it. Now I need it. What do I do?

Speaker 5 (18:22):
Yeah? And networking is hard. I mean people don't know
how to network. But networking is really about building relationships
and being a good listener, but being very clear and
precise as to what you want from someone. So if
I was referred to you someone said you need to
go and talk to Brian, I would make sure I
did my homework and prepare questions, and then when I

(18:43):
asked for your time, I would say, can I have
fifteen minutes of your time? We could meet for a coffee,
or we can do a zoom conversation like this, and
my goal would be to get information from you about
a specific field. So maybe I was interested in media,
and at the end of it, my goal should be
to say, Brian, can you connect me for three people
who I could continue the conversation with. So my goal

(19:06):
in talking to you is not about Brian, can you
get me a job? It's I'm looking for some specific
information about the sector that you're in, and I'm asking
whether you can connect me with a few other people.
So the whole idea is to build this web of
contacts so that your LinkedIn profile is one that is
attractive to people that other people want to connect with

(19:27):
on sources like LinkedIn. But it's also just to have
conversations to really fine tune what it is that you
want to do. And it's then that group of people
who might say, you know, you might say, oh, I
had a conversation with Kirsten, and then I recall that
someone down the road or in an office next to
me was looking for someone with her skills. I'm going
to connect her. And so I think it's that whole

(19:50):
idea of how do you build your comfort in articulating
what you want to advocating what you want because no
one's going to do it but yourself, and then bilding
up that group of people that you can call on
if you have maintained good relationships and you find some
way to provide value to the other person. Okay, so
that was a come.

Speaker 2 (20:09):
There's a couple of things that you said that I
think are worth underlyining.

Speaker 3 (20:11):
So first is you've got.

Speaker 2 (20:12):
To have a good LinkedIn profile and so therefore and
it's got to be up to date, it's got to
be accurate, and it's got to be, you know, as
compelling as it possibly can be. Some are completely blase
a some have got a picture from fifteen years ago publication,
and other people don't sort of keep it up to date.

Speaker 3 (20:29):
And and so I think that, you know, ensuring.

Speaker 2 (20:32):
That it's up to date is critically important. The second
thing you mentioned, which a lot of people don't do,
and I think is really critically important, is do a
little bit of research on who you're going to be
talking to. I can't tell you how many people come
and interview with me or set up a networking thing
with me or whatever, and they don't even.

Speaker 3 (20:46):
Know anything about me.

Speaker 2 (20:47):
They haven't looked me up on LinkedIn, they haven't you know,
they don't know anything about my own resume, and they
therefore come without any good smart questions. And I think
that that's really that's really silly. And even if you
only do it for a couple of minutes before you,
you know, you show up at my at my office,
do it for a couple of minutes before you show
up at my office. And then the third thing you
said is have an ask and ask to me to

(21:08):
some other people. And so I think that that's critically important.
I think that you don't you know, what's the line about,
you don't get any you know, you don't make any
sales if you don't ask for them. If you you know,
you miss every shot you don't take, you miss every
goal you don't take a shot for. So whatever the
line is right that I'm trying to think of, you know,
it's appropriate. You got you you've got to have an ask.
The one thing you didn't say, which I think is

(21:30):
really also really important is follow up afterwards and say
thank you and uh, And I can't tell you how
many people come and ask for my time or meet
with me or whatever that don't follow up afterwards. And
the follow up is critically important because that reminds you
that you had the meeting, It reminds you that the
person's a nice person, It shows gratitude and it and
it gives you, you know, the logic of potentially continuing

(21:52):
the conversation. So I think that's that's critical. Tell me,
how do you how do you tell some of the
people that you're that you're counseling to go to an
event though, like searching someone on LinkedIn is one thing,
but going to an event.

Speaker 3 (22:07):
What do you say about that.

Speaker 5 (22:09):
Events are tough? I mean I always think of networking
as you know, there's there's dinner party conversations and then
there's cocktail party conversations. I much prefer the dinner party
conversations where you can sit beside someone you know, you've
got a period of time you can really sort of
build a relationship, whereas cocktail party conversation is a much
more transaction. And so for our clients, we say what

(22:31):
are the ones that you think you'll be most comfortable
in and when we do our own events. So we
do a number of events as fundraisers, and then we
do events for our clients. There's an element of networking
built into all of them, and so they have a
chance to be able to practice in a in a
safe space. But we always say to clients, you know,
go with someone, Go with someone who you've met at

(22:53):
an event. Go with someone you've met in a program
at least that gets you into the door, But don't
stick with that person. Because if you and I are
going to an event and we know each other and
we're sticking to each other, then we're not going to
meet other people in the room. So walk around the room.
You know, find someone who is engaging in an interesting conversation,

(23:13):
insert yourself into the conversation. I know it's awkward and
it's tough, but people will stop a conversation and they'll
say hello. Or if you're walking around and you've got
a business card and you've got some kind of a brochure.
As a way to be able to break the break
the ice, think of some questions to ask people ahead
of time so that you can start with an opener

(23:34):
that's not going to be too cheesy. It could even
be something about the weather, or it could be look
at how the j's are doing. Whatever you feel comfortable
talking about. But it's important for people to walk around
the room. And so if two people come together. If
we have two clients who go to an event, they
need to go in opposite directions. They need to meet people,
and they need to come back and then talk about
what that experience was like, because that's a way for

(23:55):
them to be able to build their confidence and to
egg each other on in a positive way.

Speaker 2 (24:00):
Tines and I watched a TED talk by a professor
h psychologic psychology professor from the United States recently who
said that if you ask people what about the weather
or about the jays, or about you know, what do
you do? Or you know, are you busy? Things like
this people have they're just in in in sort of uh,

(24:21):
automatic responsible. They don't even registerate, it doesn't impact them,
and you're completely forgettable.

Speaker 3 (24:27):
And so what they said is.

Speaker 2 (24:28):
That you got to think of questions that really motivate
people to think and then respond. And so one of
the suggestions they had was have you got any exciting
projects that you're working on right now? Or have you
got any interesting travel plans coming up? Or something like that.

Speaker 3 (24:43):
So something that makes someone stop and.

Speaker 2 (24:45):
Think and uh and and and and really respond with
with a little bit hopeful of excitement rather than yeah,
I'm just really busy or you know, yeah the weather's crappy.
And I thought that was interesting advice.

Speaker 3 (24:58):
What do you think of that?

Speaker 5 (24:59):
Yeah, And we actually there's a number of tools that
have cards in them when we have many of them
in our office where you can look at some of
those different questions to stand out from the group. And
I think it depends on the situation. Yeah, I'd love
you know, someone coming up with a different question makes
you stop, It makes you think, and so I think
that it's always interesting to see what the nature of

(25:21):
the question might be. But it could be something that
you want to learn about that person, or maybe you
know about that person and you've got a way to
ease into the conversation. And so yeah, so maybe it's
not the weather and the jays. Maybe it's something that
you're really curious about, or it's something that is an
I wonder question that causes the person to stop and

(25:42):
to pay attention. But there's loads of tools that people
can buy that have some really fun questions that are
good ice breakers. And so you know, we say to
our clients, take some of those or learn some of
those and have them in your literally in your back pocket,
not to pull it out and read it, but really
to have that as a tool to be able to
support you and make you feel more comfortable.

Speaker 2 (26:01):
But is that working important?

Speaker 5 (26:03):
Yes, it's very important. It's very important.

Speaker 2 (26:06):
People still get jobs based on who they know and
who they are rather than based.

Speaker 3 (26:10):
On just the resume.

Speaker 5 (26:11):
I think so, so THEE is not.

Speaker 2 (26:12):
Just a purely objective place that that it's somewhat subjective
and it's based on who you know, how your interaction
is whether you're impressed by someone, et cetera.

Speaker 5 (26:22):
Yeah, and I think it may be that it's not
that that people are using it to get through the system,
but I think that's a way to differentiate. If a
job is getting a thousand applications, then no one's going
to read through that. I think if there's an opportunity
for someone, if someone reaches out to me and wants
to make a connection, I will always make time for them,
because especially someone who's a young person, because it's important

(26:43):
to be able to give people some advice. And so
if people are taking that information information and acting on it,
then kudos to them. You know, there are certainly people
who got jobs because their parents knew someone or they
connected with someone, But the person who's getting the job
still has to do the hard work. They still have
to do the heavy lift of meeting with someone and
talking about them and trying to convince that person that

(27:05):
they're a great hire. So I've made lots of connections,
but then it's up to the person who follows up
to be able to make it happen for them. So
I don't have an issue with it. I think if
people are trying to use it to get through the
door and not have earned their way in. Then that's
a problem. But I think that networking is about building
those relationships, and we do that with our clients with

(27:27):
a whole bunch of corporate partners. We bring corporate partners
in to talk to our clients about the work that
they do, but also to be able to get to
know them and to talk about the sector. So someone
might say, Okay, after talking to Brian, maybe media is
not for me, maybe I'm looking at something else. But
that was a really helpful conversation. So networking might not
be about getting a job in an area that is

(27:51):
close to what you do. It might be about okay,
so I've learned enough that this is something that probably
isn't the right fit for me. So it can work
both ways.

Speaker 2 (28:00):
A lot less about you know who you know and
getting you know your father, your mother, or your uncle's recommendation,
because that might help you get one job, but it's
certainly not going to help you get a good career.
I do think it's a lot about personality, about the individual.
I think people want to work with people that they
want to work with, that are nice, that can contribute

(28:20):
to their team, that can contribute to their organization, and
how do you assess that from a resume.

Speaker 3 (28:26):
It's pretty difficult to assess that.

Speaker 2 (28:27):
From a resume. And so therefore the way you get
it is through a recommendation, through a reference, through someone saying, hey,
you know, Brian is hopefully they say a nice guy,
or Kirsten's a wonderful lady and you should hire her,
or you should do business with her. And so I
think that it's only natural that people want to have
someone else vouch for them and say nice things. And
so therefore youve got to get out and meet people

(28:49):
to get that opportunity. We're going to change gears now
after the break, and we're going to change and talk
about the not for profit sector and some of the
challenges that our guest is run into and advice that
she's gone on raising money in a pretty challenging economic time.
Stay with us, everyone back in two minutes.

Speaker 1 (29:09):
No Radio, No Problem stream is live on SAGA nine
six am dot C.

Speaker 2 (29:25):
Welcome back everyone to the Brian Crimby Radio War. I've
got Kirsten Eastwood with us tonight. She's the president of
a really interesting organization called Dress for Success Tonto sounds fantastic.
I want to check out more about this Dress for
Success DRON was a charity whose mission is to empower
women to achieve economic independence by providing the network of support, work,
attire and career development tools. Christ And we've had Kirsten,

(29:49):
I apologize, We've had a good conversation about dress. We've
had a conversation about networking. Now I want to change
if we could and talk a little about.

Speaker 3 (29:59):
The current state.

Speaker 2 (30:00):
Is it not for profit sector, is it good or
is it challenging.

Speaker 5 (30:03):
It's challenging, and it's been challenging for a while, and
I think it's going to be challenging for the next
at least five years. And the reason I say that
is that we had talked earlier about demand. So demand
is up, and demand is up across all kinds of organizations.
You know. We see that through food bank usage, We
see that in terms of housing and other social services.

(30:25):
We know that funding is basically stagnant or it's going down.
Government grants are increasingly hard to get. Often that government
grants are based on the government that we have in
terms of their inclination to supporting social programs, and when
governments change, as they have, both provincially and federally over

(30:47):
the past. Here that leaves the nonprofit sector with some
question marks about what funding is going to come back.
The other thing is the staffing, is that nonprofit sectors
don't typically pay a lot of money for staff because
it's limited to the funding that they that they have.
A lot of the jobs that we can offer are

(31:08):
part time or contract positions without benefits, So it's not
exactly ideal for someone who although that might be passionate
about the cause, it doesn't make for a lot of sustainability.
And that's part of the challenge in my opinion, is
it's the sustainability of the sector is it's very hard
to talk about making systemic change, so, you know, addressing

(31:29):
some of the issues of newcomer women in barriers that
they're dealing to get jobs that can't be done in
six months, and so if we had funding for three years,
we could make a lot more impact. But it's very
hard to be able to get funding like that. So
that's the big challenge that we have right now. It's
around the funding, it's around staffing, and it's around demand

(31:50):
for services. The other thing that we're starting to see
more of is the impact of the economy and tariff's
play a role in this on people's ability to be
able to give. So individuals who typically would support organizations,
as well as corporations that typically have supported organizations, you know,
for things like events sponsorships, for example, that's changing. I've

(32:12):
been at the organization for almost two years and our
ability to attract organizations to sponsor events has changed significantly
over that time, and so we as an organization have
to think completely differently about how we're going to engage
with individuals and companies. How are we going to make
our organization look relevant and interesting, and how do we

(32:33):
provide value to people who do come to our events
or do want to become a monthly donor, or for
a corporation who wants to partner with us, And so
a lot of that has has led us to doing
some fairly innovative work. And we're able to do that
in some ways because we don't have core funding, So
that means we have no funding from government, we don't

(32:54):
have United Way funding, and so we raise most of
our money through some foundation grants and fundraising. But it
means then that we can change things up, we can
change programs, we can pivot to use that overword pandemic word,
but we can also be much more nimble in terms
of how we change what we're offering to organizations. So

(33:15):
I always say we don't want to be a charity
with our handout. We want to partner with companies to
be able to show community value. So when I talked
about sponsorships being more challenging, now, companies really want to
engage their employees. They know that when people are coming
back to work, that employee well being is a big deal,

(33:35):
that people are going to be going back into offices
four or five days a week, and how do they
focus on that employee retention and make sure that their
employees are feeling happy and connected. And one of that
is working for companies that do good things in community
that they show a philanthropic spirit. So that could be
giving people some money to be able to support a

(33:56):
local organization, giving them days to be able to volunteer
company time, and then we have tapped into that. So
we have created a whole series of programs that we
call our employee engagement Opportunities where we bring companies into
our space for mentoring, for networking, for sorting clothes that
we get as donations and we've monetized them. And so

(34:18):
my goal is that over the next year that ten
to fifteen percent of our budget is now coming from
revenue that we've generated ourselves. Revenue that's unrestricted. We can
use it for whatever we need. And that's become a
big way for us to engage with companies, and I
think has helped us to stand out a little bit
because not all organizations can do that kind of thing.

Speaker 2 (34:41):
I got to ask you about some trends though, and
where people want to put their money. You know, in
the United States ESG. Environment, society, governance, DEI, diversity, ECU,
inclusion are sort of out of fashion. A lot of
the company's charities, not for profits, et cetera that we're
focused in that area are finding a difficult to attract
either government money or private money. You've mentioned a lot

(35:04):
of things that some people in the United States are
on the right would call sort of woke, whether it
be uh, you know, newcomers or people that identify as women.
You know, you've said a whole bunch of things that
that that might be sort of not in a Canadian
context necessarily, but in a US context sort of.

Speaker 5 (35:25):
Woke.

Speaker 2 (35:26):
Are you seeing that trend in Canada? Are people reacting
negatively to that in Canada at all or yet?

Speaker 5 (35:33):
No, we're not seeing any of that now. I know
from talking with our US counterparts that they certainly are
dealing with that and they've had to change how they
have positioned their messaging in some of their programs. We're
seeing that perhaps from some companies that are headquartered in
the US, but the Canadian organizations are still able to
make a lot of their own decisions, so we have

(35:54):
not seen that negative impact. We have seen actually people
embracing the work that we do. And one of the
challenges is that how do we engage people with the
support that we need. Often the perception is is that
because we're an organization that has a clothing program, that
that's our number one need is clothing, and so we

(36:15):
need to We have found ways.

Speaker 2 (36:17):
To be at a bunch of old suits if you
need it.

Speaker 5 (36:19):
That's typically what happens when I say what I do,
People say, I'm cleaning out my closet this weekend. But
that's part of we being very intentional about saying, you know,
thank you for that, but this is actually what we
need and this is how we can engage you in
your company. So we have this this series of opportunities
and we have a range of organizations. So we work
with you know, banks, we work with pharmaceutical companies, we

(36:43):
work with tech companies, and none of them have expressed
any concern about the work that we do.

Speaker 2 (36:49):
Our digital or AI or social media impact.

Speaker 5 (36:53):
What you do, Oh, social media becomes a great channel
for us in terms of how we put our message
out there. It doesn't cost us much. The challenge with
social media, as you know, is that there's a lot
of noise out there and so we have to be
very clear with our messaging. So you know, we use
it a lot to talk about impact and the storytelling
about what we do. But interesting you talked about AI.

(37:14):
So we are actually putting together some funding asks to
create AI literacy programs for our clients. So our goal
is to have eighteen hundred women become AI literate in
the city of Toronto because AI literacy is a huge
problem in Ontario right now. Ontario is behind other provinces
in terms of having people who have embraced AI, and

(37:36):
I think we all know that this is something that's
here to stay. So we want to get ahead of
the curve and provide opportunities for our clients just to
be that much more job ready, because it's a need
that everyone's being asked from the interview desk all the
way up to people who are working in companies where
this becomes a reality. Now, So.

Speaker 2 (37:58):
Is there a role for your organization and advocacy. Do
you do anything to sort of change you know, how
people think about politicians, government thinks about social policy issues
and you know, systemic change in the area rather than
just sort of helping people get a job.

Speaker 5 (38:14):
Yeah, it's certainly part of our strategic plan right now.
Organizations like nonprofits often can't advocate if they get funding
from different levels of government because that's not our reality.
At this point, we haven't really advocated, although we're looking
at what are the causes that we really want to
be behind, you know, when we're talking about issues that
affect women, what are the things that we want to

(38:35):
be seen as the expert on. But we have been
doing a lot more government relations. We've been working with
our members of parliament both at Queen's Park as well
as in in Ottawa to really educate them on what
we do. So talking about the impact of what we
do building those relationships and sharing outcomes of programs with

(38:56):
that impact story. So we just started that work, we've
had success us and we are hopeful that that's work
that we can continue to do because then that becomes
the opportunity to talk about the issues around the systemic barriers.
So the credentials foreign trying credentials. We can't do anything
about that ourselves. Are there people who can influence that

(39:17):
decision and an expedite some changes there. So I'm hopeful
that that will become a role that we can step
in more fully, because yes, to your point, it's great
that we can support and help women, but we need
to also look at this from a systemic level as
well too, And right now, if we get short term funding,
we can't do that. We're just scratching the surface.

Speaker 2 (39:40):
You told me ahead of time that you're going to
tell me something about a story of Yodi, not Yoda,
but Yodi. Who's Yod And what's the story of Yode?

Speaker 5 (39:47):
So Yodi is one of our first clients. She came
to Toronto from South America. She left because she and
her family were being persecuted and her husband was a
little and so he was being threatened by darg cartels
in South America, so they came here and so she

(40:08):
found Dress for Success and had a young child as
well too, and so we provided her with the support.
At that time, it was really around the clothing. And
so she has now moved on to a job with
Legal Aid, an organization that provided her with support fifteen
years ago, and so she's now employed there. And full

(40:30):
circle moment, we had a group of students from Seneca
College reach out to us earlier in the year. They
wanted to do a placement around public relations, and her
daughter was one of those students, unbeknownst to us. So
now we've connected with mother and daughter and Yodi will
be speaking at our Beyond the Suit fundraiser on October
the eighth, and she will also have with her the

(40:53):
clothing that we gave her fifteen years ago because she
kept it because she saw that as the first thing
that someone gave her. There was no judgment, it was
all support, and it was designed to make her feel
better about how she went into the workplace as a newcomer.

Speaker 2 (41:09):
How did you get to where you are? You know,
it's interesting because you've got like a master's graduate degree
in social innovation, and then you worked in what an education,
You were a professor at Senega College, and then you
were also working for York Region. So you've had a
whole bunch of different careers. How did you end up

(41:30):
where you are today?

Speaker 5 (41:32):
That's a good question. My career journey has not been
linear at all. I started off my career in tourism
and then worked in banking, and then spent ten years
as an entrepreneur. And I think I just looked at
opportunities and took them. But I think that everything that
I had done up until I started working at the

(41:53):
Women's Center of UK Region was finding that passion for
the nonprofit sector. So I think that when I started
working at the Women's Center, I saw that I could
apply the skills that I had, you know, in terms
of thought leadership, strategic thinking, partnership development, and I could
bring all of those to the nonprofit context. So I

(42:14):
really fell into it. It was not an intentional looking
for it. I hadn't really even thought about the nonprofit sector,
but it was something that maybe come home at the
end of the day and laugh about what I had
done at work, to cry over what I had done
at work. You know, ten years in banking, I never
cried about what I had done at work, and so

(42:35):
it was an opportunity for me really to make a difference.
I know that sounds pretty trite, but really knowing that
I've connected with people whose lives could be changed because
of the work that we're doing.

Speaker 2 (42:46):
You know, I think that's so critically important in life
and careers, is to do something where you think you're
really contributing. And so I congratulate you for that.

Speaker 3 (42:53):
But I got to ask you.

Speaker 2 (42:55):
One of your businesses was a salad dressing business.

Speaker 3 (42:57):
What's your favorite salad dressing?

Speaker 5 (42:59):
Oh, Caesar salad for sure. Yes. I had a salad
dressing called it was let us dress. So it was
a play on the words. Actually, the necklace I'm wearing
is something I wore. From a marketing perspective, it is
actually ahead of lettuce. And so I created the salad
dressing that I had been making for friends for years

(43:21):
and people had said, you know, I should try it,
and I did no expectations, but I got it into
a number of food specialty stores across Toronto. I still
have the trademark of the product, and maybe at some
point I'll bring it back. But I didn't want to
be someone who made a whole line of salad dressings.
I only wanted to make the one. But it was
one of those windows of opportunity. I learned a huge

(43:43):
amount about the food industry and also about marketing a
food product, and I had fun with it. So it
was one of those things that I didn't want to
have regrets about never doing it.

Speaker 2 (43:54):
You've got a big event coming up on October the eighth,
I understand, called Beyond the Suit. Tell us a little
bit about it if you could.

Speaker 5 (44:00):
So this is our signature fundraiser. It's a CIBC square
right downtown and it's a chance for people to come
together to be able to have some good food, good drinks.
We have an amazing action auctioneer called Laying the Auctionista.
We have some fabulous experiences that we're going to be

(44:21):
auctioning off, and then we have fun activations. We have
a balloon pop, we have a photo booth, and one
of the trademark characteristics of our events is that they're fun.
People come after work, they mix with each other. We
have a combination of clients of volunteers, our board, our staff,
and we have a lot of our corporate and individual partners,

(44:41):
so it really is a fun celebration of the work
we do. People leave with a better sense of what
the organization does and all the funds that we raise
will support our career development programs. So it's having fun
and making a difference.

Speaker 2 (44:56):
People are potentially interested or maybe want to buy a ticket,
where do they go is their webs site.

Speaker 5 (45:00):
They can go to our website, which is Dress for
Success Toronto.

Speaker 3 (45:04):
Dot org.

Speaker 2 (45:06):
Toronto dot org. We're gonna take a final break and
when we come back, our guest Kristian Eastwood has got
six summary recommendations for us on how we can be
more successful and some of the things that she tells
some of her clients and what they got to do to.

Speaker 3 (45:20):
Be more successful. So this is something that's going to
be a chine.

Speaker 2 (45:21):
To hear back into.

Speaker 6 (45:23):
Stay with us, everybody, No Radio, No Problem.

Speaker 1 (45:30):
Stream is live on Sagay nine six am dot C.

Speaker 2 (45:33):
A welcome back everyone to that. Bran Crumby Radio R.
We've got Kristin Eastwood with us tonight. She's the president
of Dress for Success Toronto. We've talked a little bit
about how you got to dress for success and whether

(45:54):
you got to wear that suit and I think you
got to wear a jacket and you got to dress
up and get that confidence. I'm not sure whether Kristen
agrees with me or not. She talks about being authentic
and being natural, but probably she agrees that you got
to at least be confident, So that's helpful. We've talked
a little bit about networking and some of the things
that you got to do to be networking, and I

(46:15):
think we've agreed fairmount on that. And we've talked about
the challenge and not for profit sector, and she's got
a fascinating career where she's spent time in banking and academia,
in schools from an administrative standpoint, and now she's in
the not for profit sector, and I think there's probably
a real lesson in that, in being open to change
and sort of career experience. And we're gonna end with

(46:36):
six recommendations she has that she wants to give us
all that she gives some of her clients on how
to be successful and successful in the not for profit sector,
successful in life. And I think they're really interesting. So
what are your six recommendations to us?

Speaker 5 (46:50):
Please? So I mentioned before, but sees those windows of opportunities.
Those windows aren't open very often, and it could be
someone calls you, or you get an email, or that
you see something in passing on a street. But those
windows of opportunities have gotten me to where I am
now because the second point is take risks. And so

(47:10):
I took risks on something that was an unknown and
I have no problem doing that. I failed sometimes in
other places I've been successful, but they were all learning
opportunities focused on building long term relationships. I'm not interested
in transactional relationships, and that's something in my personal life

(47:30):
as well as in my work. Transactions are like quick
and they're cheap. You know, someone gives you money for
you know, a one time event or a one time need.
But we have found that we've had a lot more
success a Dressed for Success Toronto when we build relationships.
We work with some fabulous organizations who have been wonderful
about giving back and now they understand us and they

(47:53):
come to us with opportunities. We don't have to chase them.
So focused on their relationships. It takes time, it takes
good listening, but it's really important and be clear on
impact as a nonprofit, you need to have great stories
and you need to have data. So when you're trying
to convince someone to give you money, whether it's fundraising
or a funder, you need to talk about impact. You

(48:14):
have to have the stories like a yode or you
also have to have the knowledge that people want to
be part of something that makes a difference and they
want that return on investment. So if you're going to
give me one hundred thousand dollars, I need to be
able to say we were able to help X number
of women or these number of women got jobs or
went back to school, so that you feel to be
part of that change. When I worked in a school,

(48:36):
we talked about the framework of head, heart hands. When
I was working in an elementary environment. Is it for
people who want to give you know? You need to
have a combination of noticing something or hearing something on
the radio might be a story that connects, and then
you need to figure out is this something that I
can feel in my heart? Is this something that makes

(48:57):
me excited and passionate about. So it could be around
working with animals, or it could be around working with children,
or it could be an environmental cause and then think
about what you can do about it. So the combination
of head, heart hands connects people their logic, their hearts,
and then their ability to make a difference. And then
the last is the whole idea around collaborating. You know,

(49:17):
organizations like mine were often pitted to compete against other
nonprofits because of the funding model. But how do we
collaborate more together? How do we use our resources together?
If we have common missions, how do we work together
to share? And there will be some cases, I'm sure, Brian,
over the next few years where charities will have to

(49:38):
come together and merge because they will not be able
to function on their own. And that's probably okay because
we want clients to continue to be supported by the
nonprofit sector and not for organizations to go under. So
those are my sort of tips as to how I
found that we've made a difference at dress or Success
And just on the comment about the jackcket jacket, so

(50:01):
the number one clothing item that our clients want. So
I think there's something on what you're saying and something
about the authenticity because people find something about a jacket
that's very appealing.

Speaker 2 (50:12):
I'm going to offer one last suggestion to everyone that
sort of takes into account some of the six recommendations
that you made, and the networking conversation and the LinkedIn
and the connection and the challenge of the not for profits,
and that is I have found one of the best
ways to connect with people and establish long term relationships

(50:34):
and have an impact on society is to actually volunteer
for an organization, a charity or not for profit and
or frankly a political organization, because I think the way
you do when you volunteer for an organization like that
is that you meet people like our guests, who are
passionate about what they're working about, and you get together
with some people and you work on something of common cause,
and they're not necessarily the people you work with every day.

(50:56):
There's something that you work with, you know and have
got content with people you know throughout the economy, throughout
the community, and you hopefully do something that's a benefit
to the not for profit or the charity and for
benefit for the community and for.

Speaker 3 (51:09):
Benefit to yourself.

Speaker 2 (51:10):
And so I think one of the best ways to
actually get involved, to network, to make long term relationships,
and to benefit yourself and your community is to get involved,
volunteer get out there.

Speaker 5 (51:23):
So I absolutely absolutely agree. We have a program that's
just wrapping up our Newcomer Volunteer program where our clients
got volunteer experience as well as Canadian work experience, so
that was important. But yes, you're exactly right. Volunteering is
a way to be able to build up your experience
that you can do something outside of your work, maybe
put it on your resume, and make a really good

(51:44):
connection to other people. We have volunteers. He've been at
Dressed for Success for over ten years, and they're there
because they love the work and they want to be
part of it. So that's a really great point. I'll
add that to be my.

Speaker 2 (51:54):
Seventh Christianity's with Dress for Success. Chronald, thanks so much
for joining us.

Speaker 3 (51:58):
I really appreciate it.

Speaker 2 (51:59):
That's our show for tonight. Everybody, thank you for joining.
I remind you I'm on every Monday through Friday at
six o'clock on nine sixty am. You can stream you
online at Triple W Saga nine sixty am dot CA.
All my podcast and videos go up on my website
Briancromby dot com, on YouTube channel, on social media, on LinkedIn,
and a whole bunch of podcast servers as soon as
the radio show gets broadcast to air.

Speaker 3 (52:18):
Thanks for joining.

Speaker 6 (52:19):
Good Night everybody, Thank you, No radio, no problem.

Speaker 1 (52:26):
Stream is live on Sagay nine sixty am dot CA.
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