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How to find the right mentor for your future startup

February 19, 2021

Three of Toronto’s leading entrepreneurial women give their tips on finding the best mentor for you, and how to pop the question.

If you’ve ever talked about starting your own business, you’ve probably been told to find a mentor. But if you’re new to the world of entrepreneurship, this might seem daunting.

As a starting point, take a look at the careers of local businesswomen Emily Mills of How She Hustles, Jasmine Williams of Jasmine Williams Media and Christine Lieu of CL Designs. While the three of them have taken very different career paths, there’s one key component that bonds them: they all had someone in their corner, helping guide the way.

Here, they offer their tips on finding the right mentor.

The purpose of a mentor

Over the last decade, How She Hustles has become one of Canada’s leading social networks for professional women, hosting events, panels and pop-up shops to connect women from across the country. With 10 years of experience, founder Mills has built a business inspired by the value of mentorship, and has seen how it can unlock new opportunities for both the mentee and mentor. Mentoring is all about support, resources and an exchange of knowledge.

“The best mentor-mentee relationships are about exchanging value,” Mills says. “It’s not a one-way street. It’s about two people who are learning from each other so they can see the world from a different point of view and go out and make a meaningful impact.”

It’s especially important for BIPOC women, who “are already underrepresented in positions of leadership in Canada,” Mills adds. “Mentors are an active ally and proactive champion who can open new doors of possibility.”

“We need to think deeply about mentorship with equity and inclusion in mind, now that the world has opened its eyes to racial injustice and anti-Black racism,” she adds. “Mentoring relationships can be really meaningful when both parties are honest and authentic about how power, privilege and identity impact their lived experiences and dynamics.”

Having a mentor for Lieu meant having access to an incredible resource throughout her time at OCAD University and building her design and branding company, CL Designs. Thanks to their support, she honed in on her passion and learned how to start a business in the design world. After being paired with her current mentor, Fan Fit Gaming’s Rob Green, while in the Business In The Street Program last year, she’s increased her yearly revenue ten-fold and started her podcast, Brand Party.

“It’s having a trusted person and resource who you can get open feedback, support and guidance from,” she says. “Rob was generous enough to offer monthly guidance moving forward long after the program was completed, and has helped me grow personally and professionally.”

Choosing the right mentor

While Toronto is full of accomplished business leaders and entrepreneurs, you want to find someone who is the right fit for you, Williams says. She’s had experience as both a mentor and a mentee and for her, it means everything to work with someone who has faced similar challenges.

“Ideally, it’s somebody who has overcome these challenges so you can really learn from what they did and try to apply it to your own business,” Williams says. She met her first mentor at a Ryerson University advertising workshop when she was a journalism student. Once she realized she wanted to go freelance full-time and start her own content creation business, Williams reached out to someone she came across on a Facebook group. Both offered her consistent support—through messages, emails, phone calls and coffees—that have helped her business grow.

There are various avenues to finding the right mentor, including through word-of-mouth from colleagues, networking, Facebook groups, and more formally, through mentorship programs. Lieu suggests looking outside your own network to get a new perspective.

“Find someone who’s happy for your growth,” Lieu says. “You want to find someone who’s genuinely invested in giving back and helping you. Be critical of who you invest in and receive advice from.”

Williams and Lieu didn’t set out to find their first mentors when they did. They both stumbled upon their current mentors through casual networking within their industries, but Mills worked with a foundation, DiverseCityFellows, who helped her find a match.

“It helps to know what you’re passionate about, what areas you may need to develop and what type of mentor you’re looking to meet,” she says. “It’s also important to consider what you can offer. Even if you’re younger or have less experience, you can always bring value.”

Popping the question

While there’s no handbook on how to ask someone to be your mentor, there’s certainly an etiquette when it comes to formally making the request. For Mills, it comes down to four key steps: Do your homework, ask with clear intention, offer value in exchange and make your request manageable.

“Show the person that you know who they are and know what you hope to learn from them, based on the research you’ve done,” Mills says. “Consider how to frame your relationship in the easiest way for your mentor to say ‘yes.’” You might request a 30-minute Zoom call once a month, a bi-weekly email exchange or a coffee check-in once a quarter, depending on your own needs and the availability of your mentor.

Building a rapport before asking for mentorship is important, too, Williams says. Although meeting in person isn’t possible these days, asking someone to mentor you out-of-the-blue can be off-putting. Put the work in to build a relationship, show your interest and offer up your own experience so it’s a mutually beneficial arrangement.



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