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

Laila Arain: 0:01

Hi, everyone. Welcome back to the next episode of the Bay Street Capital Holdings podcast titled How'd You Do It & Why Should I Care? This series aims to highlight women doing amazing work in various industries. So today, we are so lucky to be joined by Kelli Thompson, who is a Women's Leadership Coach and Speaker. Hi Kelli, lovely to have you on the show.

Kelli Thompson: 0:19

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

Laila Arain: 0:22

Amazing. So let's dive straight into the questions and start off with an introduction about yourself. And also maybe a brief overview of the question, how do you do it? And why should I care?

Kelli Thompson: 0:32

Absolutely. So I'm a corporate veteran, I was in corporate America for over 15 years. And I spent the majority of my career in banking and investments where I was oftentimes the only woman in a lot of decision making rooms, I left and then went to a technology company. Same story, often the only woman in the leadership table or making decisions, surrounded by men, went to work for a leadership consulting company, but ultimately went out and started my own business. And so why did I do it? Well, one, I was tired of traveling, I was tired of being on the road all the time. And I really loved loved loved coaching. One of the things that I especially love to do as a woman leader, was to coach and mentor other women leaders in the workplace, because there were only men in the senior leadership teams. And so there was just different challenges and different things that we, you know, had to work through. And so you know, now in my coaching practice, I solely focus on helping women advance to the rooms where decisions are made. So why should you care, because if you're listening, and you are a woman, there are just some systemic challenges that need to be addressed in the workplace today. And so I love helping women, I've built my practice around helping women not only address those challenges, and leave with more confidence in the workplace, but really also working with workplaces as well on what things need to change systemically so that there can be more diversity and leadership teams. And when there's more diversity and leadership teams, organizations make more money, this is an economic issue that we should care about.

Laila Arain: 2:00

Definitely, highly important. And I can see how your previous roles in tech and finance kind of inspired your journey this way. And in this direction. So I'm kind of curious, after leaving those welds and starting your own company, what were the best resources that helped you along your along the way?

Kelli Thompson: 2:16

Oh, gosh, the best resources were other entrepreneurs. Let me give you one an example. So in the in the last kind of corporate job that I had, I actually worked for a small company and I worked for an entrepreneur, she was an author, she had built a leadership development consulting company. And can I just tell you that the best resource for me was watching her watching her being an entrepreneur watching her make decisions, talking with her about how she did things and how she started things up and how she made the decisions that she made. And just watching the inner workings of her running her business helped me become my own entrepreneur, there's no way I could have done it had I not seen her do it. And that's kind of the the bottom line of this whole thing is, is get in touch me getting in touch with other female entrepreneurs who were starting their businesses and were successful learning from them was absolutely critical to my success.

Laila Arain: 3:12

No, definitely very important. And I'm kind of curious, coming off of the How did you find out about these entrepreneurs? Did you have a network that you tapped into? Or what was it like?

Kelli Thompson: 3:22

Yeah, so I found one of them. The one that I mentioned, she was an author, and she was actually a consultant, she came in and did training in corporate America when I was there. And so that's how I met her. And her and I had just stayed in touch. So that was one connection, that just was long lasting. And that's how I ended up working for her. And then when I went off on my own, what I started to do was I started to reach out to other women I had met in some of my training and coaching programs. And so what I was doing was I was taking training programs to help me be a better coach. And so there were other women in there also learning how to be a better coach, and they were running their own businesses. And so that's just how I met them. And then social media is just phenomenal for this. The third thing that I did was I found this local women entrepreneurs group in my hometown, this was pre COVID. And we I would go on sites, the meetings and just meet with other local women entrepreneurs, and again, learn share stories, talk through challenges. And we of course, continue the discussion, you know, through COVID online and everything. But that was so critical to really build my own network, you know, through someone, just the existing structures that I was in.

Laila Arain: 4:33

Definitely very incredible. And I like the three different ways very contrasting, but definitely helpful in your career. Yes, yes. Um, and kind of further about your entrepreneurship ventures. I'm curious, are there any lessons that you wish you would have known before starting in this industry?

Kelli Thompson: 4:49

Yes. Where do I even start? Okay, so this one is going to surprise you and I talked about this in my upcoming book. I He was not aware of how many mindset issues I had. And let me kind of unpack that a little bit. So when I was in corporate America, I had and struggled with many of the same things that other women struggle with. And I write about this in my book, doubt, impostor feelings, staying silent when I should be speaking up, not asking for the things that I need. I mean, a lot of that is mindset driven, there are some systemic issues we need to address. And I also discussed that, but a lot of that was my own doubt, my own lack of confidence, my own what I call expensive mindsets, I always say expensive mindset, expensive thinking thoughts cost you in your peace, your potential and in your paycheck. Well, what I didn't know, was just how expensive those were going to be when I went out on my own. Because you see, in corporate America, if you don't speak up on a few things, or maybe like some doubt, or perfectionism makes your project turned in a little bit late, you're still getting paid every other Friday. But when you start your own business, and you have some of these expensive mindsets, these expensive thoughts, these doubts, they were keeping me from launching programs all together, they were keeping me from reaching out to people that could be potential clients, or business partners sources of revenue. And so when I was not doing these things, and I was allowing these doubtful expensive thoughts to stall, to not act to not launch programs to not do things that would generate revenue for my business, they became like financially expensive, because then I wasn't getting paid. So in corporate America, I kind of hid them, because I'm getting paid every two weeks. But when you're an entrepreneur, if you don't launch things, and offer products and your mindset, junk is in the way of all that you don't get paid. And so what I wish I would have known was how important just mindset work was going to be and how not getting in my own way, you know, it's not the things you think about, you always think about, like the nuts and bolts of starting the business, like your website or your payment systems or something. But it's your mindset. And I really wish I would have been more prepared for that going in

Laila Arain: 7:04

ICIC and sort of carrying on from that, how did you change your mindset? Because sometimes it's set in stone, something that you're so used to?

Kelli Thompson: 7:12

Yeah, good question. So I changed my mindset, because I had to learn the hard way, which is how I learned all things. And like, my business just wasn't accelerating as quickly as it should be. You know, I mean, when you start a business, you want to do it, because you want it to replace corporate income. And, like, I just started to realize, Oh, I'm really holding back on launching this training program I want to offer to women or I'm really holding back on promoting my services. And so when I started to notice that my business wasn't making some of the financial targets that I wanted to make, like I had to go inward and be like, well, what am I doing? Or what am I not doing? And so that's kind of how I figured it out was like, oh, oh, like this is on me. Now, I don't have any other co workers to help me. And so that was a huge aha, that recognizing that, you know, my financial results weren't coming, because my mindset wasn't there. And so for help. That's where I really leaned on my coaching network, to be honest, the people, the other women entrepreneurs that I met along the way, and honestly, just having the conversation with them was so healing because we could all sit around the room and say, You know what, I struggle with that, too. I struggle with pricing my services a certain way, too. I struggle with asking people to do business with me, too. I struggle with doubt and confidence. And what I realized through all of that was just how ubiquitous it is not only an entrepreneurship, but for corporate women. And honestly, you struggling with that myself made me help corporate women better now on the back end, because now I can see how much I struggled with that in the work environment, but I just wasn't aware of it because I'm still getting a paycheck. Yeah. So yeah, really working with other women, other coaches was really, really helpful for me and normalizing it and then finding solutions to work through it.

Laila Arain: 9:01

Okay. Okay. I see. And on in a similar vein, actually, what kind of advice would you give to somebody who is wanting to pursue a career similar to yours?

Kelli Thompson: 9:10

So if you want to pursue a career in entrepreneurship, one, I think it's just really important that you have some realistic expectations by how long it can take for your business to fully realize its full potential I often say, and I used to be in sales before this, that three years, three years is how long it will probably take for your business to really start turning through some revenue. If you want to start a business, you know, be an entrepreneur like mine, I also think it's really important to have experience in the thing that you are, I'll just speak to coaching you are coaching on I think one of the things that makes me successful as a women's leadership coach, is because I spent 15 years in corporate America and I know what it's like to be a woman in a male dominated field. I'm Not saying that you have to have that what I am offering is it's quite helpful, because you sat you sat in their shoes. And I would say the third piece of advice that I have for individuals who would want to run you know, a business similar to this would be, you know, it's going to be really important that you're comfortable with taking risks. For you risks could be like asking people to do business with you. I often say that the job that prepared me the most for being an entrepreneur, was when I was in phone sales in corporate America, I made 80 phone calls per day, to sell people and businesses to take credit card processing. And what that was terrible job. It was worse than McDonald's when I worked there, and I was 15. Because it was rejection all day long. And it was building resilience of getting rejected learning from that, what do I need to do differently and moving on and not getting cooked to it. And that is what entrepreneurship is, it is every day, making outreach, making contacts, you know, selling yourself selling your business, getting excited about what you have to offer in the world, you have to if you want to get other people excited, and then knowing that some people are gonna love it, and some people aren't. And so how am I constantly learning from that? And continuing to adjust so I can meet the needs of my clients. So

Laila Arain: 11:21

yeah, but through all that difficulty, I'm sure it's definitely worth it. In the end, when you see your company kind of prospering?

Kelli Thompson: 11:27

Yes, yes, I'm actually in my third year, and I say to my like, I'm so grateful that I stuck with it. And some really, really hard times, especially through COVID, because it's starting to turn the results I was hoping for and I think it's just such a reminder, I always say this to my clients, but it's this consistency isn't sexy. It sure does work. Yeah. And that's really what a lot of entrepreneurship is, is it's consistency, day in day out, even when you think no one cares, no one's listening. It's continuing to do that thing that you believe in. And you're passionate about knowing that if you're consistent, it will start to turn some of those results. And so that's where I am in about year three. So

Laila Arain: 12:06

let's say Well, congratulations on hitting the year three, Mark, I know that entrepreneurship is especially difficult for women. So that's a great achievement. Yes, thank you. And finally, kind of what is one common myth about your profession or field that you want to debunk?

Kelli Thompson: 12:21

Hmm, that's such a good one. I would say a common myth that I've heard out there is that those who can't do it, Coach it or those who can't do it, teach it? Oh, yeah. And so a lot of a lot of people, I've just kind of heard Oh, well, they became a coach, or they're a coach, because they can't hack it in the corporate world, or they were never a good leader, and they couldn't make it. And so I think that's one of the things that one is, is untrue. I know a lot of really great coaches and teachers and consultants who were very, very excellent and corporate. They just like me, I wanted to stop traveling, and I wanted to be my own boss, I want to set my own schedule. And so I think that's what makes me different and unique is I did do really well in corporate, I enjoyed it, I still have a lot of connections from my corporate days. I just wanted to be my own boss, I wanted to drive my own ship, and I love being an entrepreneur. So I think that finding the right coach can be really, really helpful. And it's okay to ask that individual about their credentials about their experience. And to find someone that's the right, that's the right fit. So

Laila Arain: 13:32

very important. And thank you for that. And more into the kind of person you are, I'm really curious, what have you read or listened to recently that's inspired you?

Kelli Thompson: 13:42

Oh, okay. So I am just finished think, again, by Adam Grant, obviously, which, you know, you may be familiar with, I love all of his books, but I really love how research driven his book is in terms of, you know, looking at the studies of competence versus competence, and how we need to show up at work and how we can really set our egos aside, and how it's okay to be wrong about some things and think, again, I think that's the crux of entrepreneurship is the willingness to be wrong. Like I have to be willing to be wrong every single day about my assumptions so that I can find the right things for my clients. And so in terms of reading, I read lots of books, but that's the best book I read so far. So I would highly recommend that one if you haven't taken a look yet.

Laila Arain: 14:27

Definitely amazing. And Adam Grant is an extremely great author. So I'll definitely check that out. And who are three people who have been the most influential to you in your career? You mentioned, obviously, your network, but I'm curious, are there three people that really stand out to you? Yeah.

Kelli Thompson: 14:42

100%. So I would say the first person that was the most influential to me in my career, was one of my early leaders. Her name was Vicki. And I was a very young, entitled, egotistical person, like an employee, I thought I was going to shoot up the corporate ladder. I mean, I came into the workplace He's probably like lots of young people a little entitled, A little too much ego. I applied for a job working for her and I didn't get it. I was in sales, I wanted to be a sales trainer. And so when I asked her why she sat me down and asked me if I knew the difference between confidence, and cockiness, and I told her I did, but then she went on to give me some really good and helpful coaching, tough coaching that, in fact, made me realized I did not know the difference between confidence and cockiness. And so she became a wonderful leader and mentor to me, and really honestly just helping me grow up to grow as a leader to grow as a woman in the workplace. And so for my corporate time, it was absolutely her. The second person that was most influential to me was the leader that I had that was an entrepreneur, she was an author, her name is Sai. Wakeman. She's fantastic. She's written wonderful books, I highly recommend reality based leadership. You know, she showed me how you could be an entrepreneur in the world, she showed me what it looked like to give so freely of your time and your talents and make connections and just taught me not only how to run a business, but taught me the value of like giving of yourself and your thought leadership and how that creates connections. And I would say the third person that's been really influential to me, is someone I've never even met, she's my great grandma, she ran our 1000 acre family farm as a widow. And at a time when in the 1950s, and 60s, when women just didn't have voices, women couldn't even borrow money in their own name in the United States till 1974. And so really hearing about her and hearing her stories and hearing how she really challenged the status quo. I'm sure people had lots of names that they called her back then, because she was a direct and assertive and shrewd really reminded me that you know, when you show up, as the person you are, and you ask for what you need, and you're unapologetic about it, like you can build a legacy not only for your family, but she also employed people in her community and her farm fed hungry families. And so you know, being yourself and being unapologetic about that she taught me really can help you build a legacy.

Laila Arain: 17:07

So really great women in your life. And that's awesome to hear that they were your inspirations. And finally, to wrap up our conversation, is there any advice that you wish you gave yourself at any point in your life?

Kelli Thompson: 17:20

Oh, yes. So much. I look back. I talked about this in the first chapter of my book. When I look back, and I could give my younger self some advice, it would be this. Know what you stand for? Because if you don't know what you stand for, you will fall for anything. And that's kind of a hammock the quote spun off of Hamilton the musical Yep. Because I think that I thought I had to follow a list of things to be happy and successful. I had to make other people happy. And I was willing to sacrifice what I stood for to keep other people happy. But what really happened was, the only person that I was making miserable was myself, and I wasn't making anybody happy. So the advice that I would give to my younger self is this know what you value and know what you stand for. Because if you know, if you don't stand for something, you'll fall for anything and be unapologetic about what you stand for. And that's okay, if other people don't like it, because those probably aren't your people.

Laila Arain: 18:23

Very, very important. And I feel like that kind of mantra can be applied to anywhere and work so and in life in general. So, thank you so much, Kelli for talking with me today. This was truly an eye opening experience and discussion. And thank you for joining us on the show.

Kelli Thompson: 18:38

Thank you so much for having me. Appreciate it.

Laila Arain: 18:40

All right, then take care. Thank you. Bye bye.