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Laila Arain & Kelli Thompson | How'd You Do It & Why Should I Care?

Laila Arain & Kelli Thompson | How'd You Do It & Why Should I Care?

Released Friday, 28th April 2023
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Laila Arain & Kelli Thompson | How'd You Do It & Why Should I Care?

Laila Arain & Kelli Thompson | How'd You Do It & Why Should I Care?

Laila Arain & Kelli Thompson | How'd You Do It & Why Should I Care?

Laila Arain & Kelli Thompson | How'd You Do It & Why Should I Care?

Friday, 28th April 2023
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Episode Transcript

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0:01

Hi, everyone.

0:01

Welcome back to the next episode

0:03

of the Bay Street Capital

0:03

Holdings podcast titled How'd

0:06

You Do It & Why Should I Care?

0:06

This series aims to highlight

0:09

women doing amazing work in

0:09

various industries. So today, we

0:13

are so lucky to be joined by

0:13

Kelli Thompson, who is a Women's

0:16

Leadership Coach and Speaker. Hi

0:16

Kelli, lovely to have you on the

0:19

show.

0:19

Oh, thank you so much for having me. I'm glad to be here.

0:22

Amazing. So let's

0:22

dive straight into the questions

0:25

and start off with an

0:25

introduction about yourself. And

0:27

also maybe a brief overview of

0:27

the question, how do you do it?

0:30

And why should I care?

0:32

Absolutely. So

0:32

I'm a corporate veteran, I was

0:35

in corporate America for over 15

0:35

years. And I spent the majority

0:39

of my career in banking and

0:39

investments where I was

0:42

oftentimes the only woman in a

0:42

lot of decision making rooms, I

0:46

left and then went to a

0:46

technology company. Same story,

0:49

often the only woman in the

0:49

leadership table or making

0:52

decisions, surrounded by men,

0:52

went to work for a leadership

0:55

consulting company, but

0:55

ultimately went out and started

0:58

my own business. And so why did

0:58

I do it? Well, one, I was tired

1:01

of traveling, I was tired of

1:01

being on the road all the time.

1:05

And I really loved loved loved

1:05

coaching. One of the things that

1:08

I especially love to do as a

1:08

woman leader, was to coach and

1:11

mentor other women leaders in

1:11

the workplace, because there

1:14

were only men in the senior

1:14

leadership teams. And so there

1:18

was just different challenges

1:18

and different things that we,

1:20

you know, had to work through.

1:20

And so you know, now in my

1:24

coaching practice, I solely

1:24

focus on helping women advance

1:27

to the rooms where decisions are

1:27

made. So why should you care,

1:30

because if you're listening, and

1:30

you are a woman, there are just

1:34

some systemic challenges that

1:34

need to be addressed in the

1:36

workplace today. And so I love

1:36

helping women, I've built my

1:39

practice around helping women

1:39

not only address those

1:42

challenges, and leave with more

1:42

confidence in the workplace, but

1:45

really also working with

1:45

workplaces as well on what

1:47

things need to change

1:47

systemically so that there can

1:50

be more diversity and leadership

1:50

teams. And when there's more

1:53

diversity and leadership teams,

1:53

organizations make more money,

1:57

this is an economic issue that

1:57

we should care about.

2:00

Definitely, highly

2:00

important. And I can see how

2:02

your previous roles in tech and

2:02

finance kind of inspired your

2:05

journey this way. And in this

2:05

direction. So I'm kind of

2:09

curious, after leaving those

2:09

welds and starting your own

2:12

company, what were the best

2:12

resources that helped you along

2:14

your along the way?

2:16

Oh, gosh, the

2:16

best resources were other

2:18

entrepreneurs. Let me give you

2:18

one an example. So in the in the

2:22

last kind of corporate job that

2:22

I had, I actually worked for a

2:25

small company and I worked for

2:25

an entrepreneur, she was an

2:28

author, she had built a

2:28

leadership development

2:30

consulting company. And can I

2:30

just tell you that the best

2:34

resource for me was watching her

2:34

watching her being an

2:39

entrepreneur watching her make

2:39

decisions, talking with her

2:43

about how she did things and how

2:43

she started things up and how

2:47

she made the decisions that she

2:47

made. And just watching the

2:49

inner workings of her running

2:49

her business helped me become my

2:54

own entrepreneur, there's no way

2:54

I could have done it had I not

2:58

seen her do it. And that's kind

2:58

of the the bottom line of this

3:00

whole thing is, is get in touch

3:00

me getting in touch with other

3:04

female entrepreneurs who were

3:04

starting their businesses and

3:07

were successful learning from

3:07

them was absolutely critical to

3:11

my success.

3:12

No, definitely very

3:12

important. And I'm kind of

3:15

curious, coming off of the How

3:15

did you find out about these

3:18

entrepreneurs? Did you have a

3:18

network that you tapped into? Or

3:21

what was it like?

3:22

Yeah, so I found

3:22

one of them. The one that I

3:25

mentioned, she was an author,

3:25

and she was actually a

3:28

consultant, she came in and did

3:28

training in corporate America

3:31

when I was there. And so that's

3:31

how I met her. And her and I had

3:34

just stayed in touch. So that

3:34

was one connection, that just

3:37

was long lasting. And that's how

3:37

I ended up working for her. And

3:41

then when I went off on my own,

3:41

what I started to do was I

3:44

started to reach out to other

3:44

women I had met in some of my

3:48

training and coaching programs.

3:48

And so what I was doing was I

3:50

was taking training programs to

3:50

help me be a better coach. And

3:54

so there were other women in

3:54

there also learning how to be a

3:57

better coach, and they were

3:57

running their own businesses.

3:59

And so that's just how I met

3:59

them. And then social media is

4:03

just phenomenal for this. The

4:03

third thing that I did was I

4:07

found this local women

4:07

entrepreneurs group in my

4:11

hometown, this was pre COVID.

4:11

And we I would go on sites, the

4:15

meetings and just meet with

4:15

other local women entrepreneurs,

4:18

and again, learn share stories,

4:18

talk through challenges. And we

4:22

of course, continue the discussion, you know, through COVID online and everything. But

4:24

that was so critical to really

4:28

build my own network, you know,

4:28

through someone, just the

4:31

existing structures that I was in.

4:33

Definitely very incredible. And I like the three different ways very contrasting,

4:35

but definitely helpful in your

4:38

career. Yes, yes. Um, and kind

4:38

of further about your

4:42

entrepreneurship ventures. I'm

4:42

curious, are there any lessons

4:45

that you wish you would have known before starting in this industry?

4:49

Yes. Where do I

4:49

even start? Okay, so this one is

4:54

going to surprise you and I

4:54

talked about this in my upcoming

4:57

book. I He was not aware of how

4:57

many mindset issues I had. And

5:05

let me kind of unpack that a

5:05

little bit. So when I was in

5:09

corporate America, I had and

5:09

struggled with many of the same

5:12

things that other women struggle

5:12

with. And I write about this in

5:15

my book, doubt, impostor

5:15

feelings, staying silent when I

5:20

should be speaking up, not

5:20

asking for the things that I

5:22

need. I mean, a lot of that is

5:22

mindset driven, there are some

5:26

systemic issues we need to

5:26

address. And I also discussed

5:29

that, but a lot of that was my

5:29

own doubt, my own lack of

5:32

confidence, my own what I call

5:32

expensive mindsets, I always say

5:35

expensive mindset, expensive

5:35

thinking thoughts cost you in

5:39

your peace, your potential and

5:39

in your paycheck. Well, what I

5:42

didn't know, was just how

5:42

expensive those were going to be

5:46

when I went out on my own.

5:46

Because you see, in corporate

5:48

America, if you don't speak up

5:48

on a few things, or maybe like

5:52

some doubt, or perfectionism

5:52

makes your project turned in a

5:55

little bit late, you're still

5:55

getting paid every other Friday.

5:59

But when you start your own

5:59

business, and you have some of

6:01

these expensive mindsets, these

6:01

expensive thoughts, these

6:04

doubts, they were keeping me

6:04

from launching programs all

6:07

together, they were keeping me

6:07

from reaching out to people that

6:11

could be potential clients, or

6:11

business partners sources of

6:14

revenue. And so when I was not

6:14

doing these things, and I was

6:18

allowing these doubtful

6:18

expensive thoughts to stall, to

6:21

not act to not launch programs

6:21

to not do things that would

6:24

generate revenue for my

6:24

business, they became like

6:28

financially expensive, because

6:28

then I wasn't getting paid. So

6:31

in corporate America, I kind of

6:31

hid them, because I'm getting

6:33

paid every two weeks. But when

6:33

you're an entrepreneur, if you

6:37

don't launch things, and offer

6:37

products and your mindset, junk

6:41

is in the way of all that you

6:41

don't get paid. And so what I

6:43

wish I would have known was how

6:43

important just mindset work was

6:48

going to be and how not getting

6:48

in my own way, you know, it's

6:52

not the things you think about,

6:52

you always think about, like the

6:55

nuts and bolts of starting the

6:55

business, like your website or

6:57

your payment systems or

6:57

something. But it's your

7:00

mindset. And I really wish I

7:00

would have been more prepared

7:03

for that going in

7:04

ICIC and sort of

7:04

carrying on from that, how did

7:07

you change your mindset? Because

7:07

sometimes it's set in stone,

7:10

something that you're so used to?

7:12

Yeah, good

7:12

question. So I changed my

7:14

mindset, because I had to learn

7:14

the hard way, which is how I

7:17

learned all things. And like, my

7:17

business just wasn't

7:22

accelerating as quickly as it

7:22

should be. You know, I mean,

7:25

when you start a business, you

7:25

want to do it, because you want

7:27

it to replace corporate income.

7:27

And, like, I just started to

7:32

realize, Oh, I'm really holding

7:32

back on launching this training

7:37

program I want to offer to women

7:37

or I'm really holding back on

7:40

promoting my services. And so

7:40

when I started to notice that my

7:43

business wasn't making some of

7:43

the financial targets that I

7:46

wanted to make, like I had to go

7:46

inward and be like, well, what

7:49

am I doing? Or what am I not

7:49

doing? And so that's kind of how

7:52

I figured it out was like, oh,

7:52

oh, like this is on me. Now, I

7:56

don't have any other co workers

7:56

to help me. And so that was a

7:59

huge aha, that recognizing that,

7:59

you know, my financial results

8:04

weren't coming, because my

8:04

mindset wasn't there. And so for

8:07

help. That's where I really

8:07

leaned on my coaching network,

8:11

to be honest, the people, the

8:11

other women entrepreneurs that I

8:15

met along the way, and honestly,

8:15

just having the conversation

8:18

with them was so healing because

8:18

we could all sit around the room

8:22

and say, You know what, I

8:22

struggle with that, too. I

8:25

struggle with pricing my

8:25

services a certain way, too. I

8:28

struggle with asking people to

8:28

do business with me, too. I

8:30

struggle with doubt and

8:30

confidence. And what I realized

8:33

through all of that was just how

8:33

ubiquitous it is not only an

8:36

entrepreneurship, but for

8:36

corporate women. And honestly,

8:40

you struggling with that myself

8:40

made me help corporate women

8:43

better now on the back end,

8:43

because now I can see how much I

8:47

struggled with that in the work

8:47

environment, but I just wasn't

8:50

aware of it because I'm still

8:50

getting a paycheck. Yeah. So

8:53

yeah, really working with other

8:53

women, other coaches was really,

8:57

really helpful for me and

8:57

normalizing it and then finding

8:59

solutions to work through it.

9:01

Okay. Okay. I see.

9:01

And on in a similar vein,

9:04

actually, what kind of advice

9:04

would you give to somebody who

9:07

is wanting to pursue a career

9:07

similar to yours?

9:10

So if you want

9:10

to pursue a career in

9:13

entrepreneurship, one, I think

9:13

it's just really important that

9:19

you have some realistic

9:19

expectations by how long it can

9:22

take for your business to fully

9:22

realize its full potential I

9:27

often say, and I used to be in

9:27

sales before this, that three

9:31

years, three years is how long

9:31

it will probably take for your

9:34

business to really start turning

9:34

through some revenue. If you

9:39

want to start a business, you

9:39

know, be an entrepreneur like

9:42

mine, I also think it's really

9:42

important to have experience in

9:46

the thing that you are, I'll

9:46

just speak to coaching you are

9:49

coaching on I think one of the

9:49

things that makes me successful

9:52

as a women's leadership coach,

9:52

is because I spent 15 years in

9:55

corporate America and I know

9:55

what it's like to be a woman in

9:58

a male dominated field. I'm Not

9:58

saying that you have to have

10:01

that what I am offering is it's

10:01

quite helpful, because you sat

10:05

you sat in their shoes. And I

10:05

would say the third piece of

10:08

advice that I have for

10:08

individuals who would want to

10:12

run you know, a business similar

10:12

to this would be, you know, it's

10:17

going to be really important

10:17

that you're comfortable with

10:20

taking risks. For you risks

10:20

could be like asking people to

10:24

do business with you. I often

10:24

say that the job that prepared

10:29

me the most for being an

10:29

entrepreneur, was when I was in

10:33

phone sales in corporate

10:33

America, I made 80 phone calls

10:37

per day, to sell people and

10:37

businesses to take credit card

10:41

processing. And what that was

10:41

terrible job. It was worse than

10:45

McDonald's when I worked there,

10:45

and I was 15. Because it was

10:48

rejection all day long. And it

10:48

was building resilience of

10:52

getting rejected learning from

10:52

that, what do I need to do

10:54

differently and moving on and

10:54

not getting cooked to it. And

10:58

that is what entrepreneurship

10:58

is, it is every day, making

11:03

outreach, making contacts, you

11:03

know, selling yourself selling

11:06

your business, getting excited

11:06

about what you have to offer in

11:08

the world, you have to if you want to get other people excited, and then knowing that

11:10

some people are gonna love it,

11:13

and some people aren't. And so

11:13

how am I constantly learning

11:16

from that? And continuing to

11:16

adjust so I can meet the needs

11:19

of my clients. So

11:21

yeah, but through

11:21

all that difficulty, I'm sure

11:23

it's definitely worth it. In the

11:23

end, when you see your company

11:26

kind of prospering?

11:27

Yes, yes, I'm

11:27

actually in my third year, and I

11:30

say to my like, I'm so grateful

11:30

that I stuck with it. And some

11:34

really, really hard times,

11:34

especially through COVID,

11:37

because it's starting to turn

11:37

the results I was hoping for and

11:41

I think it's just such a

11:41

reminder, I always say this to

11:43

my clients, but it's this

11:43

consistency isn't sexy. It sure

11:48

does work. Yeah. And that's

11:48

really what a lot of

11:50

entrepreneurship is, is it's

11:50

consistency, day in day out,

11:54

even when you think no one

11:54

cares, no one's listening. It's

11:57

continuing to do that thing that

11:57

you believe in. And you're

11:59

passionate about knowing that if

11:59

you're consistent, it will start

12:02

to turn some of those results.

12:02

And so that's where I am in

12:05

about year three. So

12:06

let's say Well, congratulations on hitting the year three, Mark, I know that

12:08

entrepreneurship is especially

12:11

difficult for women. So that's a

12:11

great achievement. Yes, thank

12:14

you. And finally, kind of what

12:14

is one common myth about your

12:18

profession or field that you

12:18

want to debunk?

12:21

Hmm, that's such

12:21

a good one. I would say a common

12:26

myth that I've heard out there

12:26

is that those who can't do it,

12:32

Coach it or those who can't do

12:32

it, teach it? Oh, yeah. And so a

12:37

lot of a lot of people, I've

12:37

just kind of heard Oh, well,

12:40

they became a coach, or they're

12:40

a coach, because they can't hack

12:44

it in the corporate world, or

12:44

they were never a good leader,

12:46

and they couldn't make it. And

12:46

so I think that's one of the

12:49

things that one is, is untrue. I

12:49

know a lot of really great

12:53

coaches and teachers and

12:53

consultants who were very, very

12:56

excellent and corporate. They

12:56

just like me, I wanted to stop

13:00

traveling, and I wanted to be my

13:00

own boss, I want to set my own

13:03

schedule. And so I think that's

13:03

what makes me different and

13:07

unique is I did do really well

13:07

in corporate, I enjoyed it, I

13:10

still have a lot of connections

13:10

from my corporate days. I just

13:14

wanted to be my own boss, I

13:14

wanted to drive my own ship, and

13:17

I love being an entrepreneur. So

13:17

I think that finding the right

13:22

coach can be really, really

13:22

helpful. And it's okay to ask

13:25

that individual about their

13:25

credentials about their

13:27

experience. And to find someone

13:27

that's the right, that's the

13:31

right fit. So

13:32

very important. And

13:32

thank you for that. And more

13:36

into the kind of person you are,

13:36

I'm really curious, what have

13:39

you read or listened to recently

13:39

that's inspired you?

13:42

Oh, okay. So I

13:42

am just finished think, again,

13:46

by Adam Grant, obviously, which,

13:46

you know, you may be familiar

13:50

with, I love all of his books,

13:50

but I really love how research

13:54

driven his book is in terms of,

13:54

you know, looking at the studies

13:58

of competence versus competence,

13:58

and how we need to show up at

14:01

work and how we can really set

14:01

our egos aside, and how it's

14:04

okay to be wrong about some

14:04

things and think, again, I think

14:07

that's the crux of entrepreneurship is the willingness to be wrong. Like I

14:09

have to be willing to be wrong

14:13

every single day about my

14:13

assumptions so that I can find

14:16

the right things for my clients.

14:16

And so in terms of reading, I

14:19

read lots of books, but that's

14:19

the best book I read so far. So

14:24

I would highly recommend that

14:24

one if you haven't taken a look

14:27

yet.

14:27

Definitely amazing.

14:27

And Adam Grant is an extremely

14:29

great author. So I'll definitely

14:29

check that out. And who are

14:33

three people who have been the

14:33

most influential to you in your

14:36

career? You mentioned,

14:36

obviously, your network, but I'm

14:38

curious, are there three people

14:38

that really stand out to you?

14:41

Yeah.

14:42

100%. So I would

14:42

say the first person that was

14:45

the most influential to me in my

14:45

career, was one of my early

14:48

leaders. Her name was Vicki. And

14:48

I was a very young, entitled,

14:54

egotistical person, like an

14:54

employee, I thought I was going

14:57

to shoot up the corporate ladder. I mean, I came into the workplace He's probably like

14:59

lots of young people a little entitled, A little too much ego.

15:01

I applied for a job working for

15:06

her and I didn't get it. I was

15:06

in sales, I wanted to be a sales

15:08

trainer. And so when I asked her

15:08

why she sat me down and asked me

15:12

if I knew the difference between

15:12

confidence, and cockiness, and I

15:17

told her I did, but then she

15:17

went on to give me some really

15:20

good and helpful coaching, tough

15:20

coaching that, in fact, made me

15:24

realized I did not know the

15:24

difference between confidence

15:27

and cockiness. And so she became

15:27

a wonderful leader and mentor to

15:30

me, and really honestly just

15:30

helping me grow up to grow as a

15:34

leader to grow as a woman in the

15:34

workplace. And so for my

15:37

corporate time, it was

15:37

absolutely her. The second

15:40

person that was most influential

15:40

to me was the leader that I had

15:43

that was an entrepreneur, she

15:43

was an author, her name is Sai.

15:45

Wakeman. She's fantastic. She's

15:45

written wonderful books, I

15:48

highly recommend reality based

15:48

leadership. You know, she showed

15:52

me how you could be an

15:52

entrepreneur in the world, she

15:56

showed me what it looked like to

15:56

give so freely of your time and

16:00

your talents and make

16:00

connections and just taught me

16:03

not only how to run a business,

16:03

but taught me the value of like

16:07

giving of yourself and your

16:07

thought leadership and how that

16:10

creates connections. And I would

16:10

say the third person that's been

16:12

really influential to me, is

16:12

someone I've never even met,

16:16

she's my great grandma, she ran

16:16

our 1000 acre family farm as a

16:21

widow. And at a time when in the

16:21

1950s, and 60s, when women just

16:26

didn't have voices, women

16:26

couldn't even borrow money in

16:28

their own name in the United

16:28

States till 1974. And so really

16:32

hearing about her and hearing

16:32

her stories and hearing how she

16:35

really challenged the status

16:35

quo. I'm sure people had lots of

16:39

names that they called her back

16:39

then, because she was a direct

16:42

and assertive and shrewd really

16:42

reminded me that you know, when

16:46

you show up, as the person you

16:46

are, and you ask for what you

16:50

need, and you're unapologetic

16:50

about it, like you can build a

16:54

legacy not only for your family,

16:54

but she also employed people in

16:58

her community and her farm fed

16:58

hungry families. And so you

17:01

know, being yourself and being

17:01

unapologetic about that she

17:04

taught me really can help you build a legacy.

17:07

So really great

17:07

women in your life. And that's

17:09

awesome to hear that they were

17:09

your inspirations. And finally,

17:14

to wrap up our conversation, is

17:14

there any advice that you wish

17:17

you gave yourself at any point

17:17

in your life?

17:20

Oh, yes. So

17:20

much. I look back. I talked

17:26

about this in the first chapter

17:26

of my book. When I look back,

17:31

and I could give my younger self

17:31

some advice, it would be this.

17:36

Know what you stand for? Because

17:36

if you don't know what you stand

17:40

for, you will fall for anything.

17:40

And that's kind of a hammock the

17:43

quote spun off of Hamilton the

17:43

musical Yep. Because I think

17:48

that I thought I had to follow a

17:48

list of things to be happy and

17:52

successful. I had to make other

17:52

people happy. And I was willing

17:57

to sacrifice what I stood for to

17:57

keep other people happy. But

18:00

what really happened was, the

18:00

only person that I was making

18:03

miserable was myself, and I

18:03

wasn't making anybody happy. So

18:06

the advice that I would give to

18:06

my younger self is this know

18:09

what you value and know what you

18:09

stand for. Because if you know,

18:13

if you don't stand for

18:13

something, you'll fall for

18:15

anything and be unapologetic

18:15

about what you stand for. And

18:18

that's okay, if other people

18:18

don't like it, because those

18:22

probably aren't your people.

18:23

Very, very

18:23

important. And I feel like that

18:26

kind of mantra can be applied to

18:26

anywhere and work so and in life

18:29

in general. So, thank you so

18:29

much, Kelli for talking with me

18:32

today. This was truly an eye

18:32

opening experience and

18:35

discussion. And thank you for

18:35

joining us on the show.

18:38

Thank you so

18:38

much for having me. Appreciate it.

18:40

All right, then

18:40

take care. Thank you. Bye bye.

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