It’s important for leaders to offer insights on empowering the next generation of leaders, regardless of age or background. Recently, BMO hosted an event in Chicago that spotlighted three trailblazing entrepreneurs, who shared their journeys and stories:   

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  Irma Bates, co-founder and President of Montenegro, Inc., a paper packaging and print provider  

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  Cassie Martin Graham, President of DME Manufacturing PA 

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  Aris Singleton, CEO of Thank God It’s Natural (tgin), a textured hair care manufacturer

Caroline Donlin, Head of Engineering & Construction, BMO Commercial Bank, served as the moderator. We hope their career journeys will inspire you to craft a strategy for accelerating your own personal and professional growth. Following is a summary of their conversation.  

Everyone has a different career path, but just about everyone also wishes there was one thing they’d known as they started their professional journey.   

Singleton, who has been CEO of tgin for four years, was only 28 when she took the reins. She’d worked her way through various aspects of the company, including human resources, marketing and accounting, so she knew the ins and outs of the business by the time she took over. Still, she says the transition from employee to CEO was a difficult one, which is why building a community was a lifeline.  

“I had to advocate for myself and build strategic relationships, and surround myself with other women who are entrepreneurs,” Singleton said.   

For Graham, the biggest lesson she’s learned is not to let your background define what you can be—sound advice from a manufacturing executive who has degrees in wildlife biology and marine biology. “What I would tell myself is never box yourself in,” Graham said. “Life changes, things happen for a reason. When opportunities arise, say yes. Take a risk.”  

Being an ally often means seeing potential in someone before they see it in themselves. Our panelists described what allyship looks like for them, and how they’ve been an ally for others.  

For Graham, who cited her husband as her biggest ally, allyship begins at home. “Look for people who are truly your partner,” she said. “A lot of the mental load is automatically put on the woman in the relationship, and I think it’s OK to give some of that to our partners. It’s OK to ask for it, and at times it’s OK to demand it. We are worth it, and we need to ask for more help at home.”  

Allies can also come from unlikely sources. Singleton noted, “My first mentor was a bald man who worked as an engineer at a construction firm. I thought, what do you know about hair care products? But because he pushed for me, I’m not afraid to walk into rooms where a lot of people don’t look like me. I plan to give back and do the same for women like me.”  

We bring our entire selves into our work, which is why building a company culture that allows people to be who they are is crucial. For our panelists, maintaining alignment with their core values while evolving their company culture starts with making your intentions known at the start.  

“In my organization, they call me the ‘culture vulture,’ because I am all about our culture and our core values,” Singleton said. “I went from employee to CEO, and I want to make sure everyone that’s in our organization loves our mission—to redefine beauty by cultivating a community that empowers women to be the best versions of themselves. When candidates are interviewing, I let them know these are our core values. When they come in on their first day, I’m the first person they see, not HR. I’m doing their orientation. I let them know these are not just words, this is why I wake up and do what I do every day.”  

For Bates, it also starts in the hiring process. “You need to make sure who you hire believes in your core values,” she said. “We are absolutely inclusive. We have a monthly lunch-and-learn where we make sure we continue to educate our employees and make sure they’re in line with us.”  

What kind of legacy do the panelists wish to leave behind? For Graham, it’s continuing to build on the advances made through previous generations.  

“Everybody in my generation stands on the shoulders of incredible women who came before us,” Graham said. “I’ve been the only woman in the room, but I know it’s less and less common now. There’s a shift that women in leadership used to have to try to be like the men, and I think there’s a lot more authenticity of when we are exactly who we are, and we show that way every single day. I hope that continues and I hope the next generation gets better and better.”  

Singleton’s notion of legacy relates to her mother and her late aunt, who taught her the value of hard work and leadership.   

“My mother sent me to Chicago to help my aunt during the summer,” she said. “I should have been hanging out with friends, living my best life. No, I was working. And while I was working, I was able to learn about the business. At that time, I didn’t see it. It wasn’t until [her aunt] passed that I realized these women had poured so much into me to prepare me to be the leader that I am today. I want to do the same. I want to make sure I’m leaving a legacy where women at the table is not a rarity.”  

As we celebrate these leadership journeys, BMO remains dedicated to boldly growing the good in business in life and highlighting leaders in our communities.