Event Recap: SheMentors Matching Day!

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YWiB Toronto just launched our brand new SheMentors mentorship program, and we got things rolling with our September 10th Matching Day! We are pleased to announce that we made 20 mentorship matches in our pilot, including 9 mentors and 11 mentees. They were carefully chosen from a pool of 51 applicants (16 mentors and 35 mentees), and we are happy to report that these established and emerging leaders truly signify what our YWiB community is about: ambitious and self-motivated women working towards their own definitions of success.

For more details on the SheMentors initiative, visit our programs page.

Also, as our team hopes to ensure all mentorship relationships are a success (and because we always go the extra mile for our community!) we wanted to add structure and fun to the SheMentors Orientation process.

Our Matching Day event was held at Eureka Hub, a vibrant coworking space in Toronto’s East End. The atmosphere was full of energy as attendees arrived, completing registration and enjoying some refreshments. The YWiB team was on stand-by to greet everyone and ensure they had everything they needed.

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 As they entered, attendees were asked to select a ‘Feelings Sticker’ that described their current mood or experience after the work day. Stickers ranged from ‘Excited’ to ‘Emotionally-Drained’, the objective being to spark conversation and break the ice. We were very excited about the cheer amount of attendees choosing ‘Excited’ as their Feeling Sticker. That said, one attendee added ‘Jet-Lagged’ to hers as she had just landed in Toronto after a long flight, and this was a great conversation-starter as the night progressed!


Our YWiB Toronto Chapter President, Sandra Riano, started things off by welcoming everyone to the event and introducing them to YWiB and our mandate. Her trademark motivational energy, sense of humour, and welcoming nature got the room ready for the things to come.

VP of Programs & Philanthropy, Lara El Shawa, followed up with an informative presentation about SheMentors and an overview of the mentorship process, SheMentors Toolkit, and expectations for the matches. Adding extra details and examples were needed, Lara clearly communicated the amount of work and thought that went into crafting and developing the SheMentors program.

Next came the moment everyone was waiting for; the matchings reveal! Programs Manager Daisy Gao announced assigned mentors/mentees and excitement filled the room. Some pairs had already met earlier in the evening and realized they were already sitting beside each other — talk about serendipity!

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Olivia Cummings, our Events Manager, was next to the mic to explain the ice breaker activity, referring back to the ‘Feelings Stickers’ everyone was wearing. Mentors and mentees then had a chance to sit down, make introductions, and review the SheMentors agreement. Mentors and mentees also reviewed the comprehensive tools and documents the SheMentors team prepared to help them along their 6-month journey. Each pair also walked away from the evening with a great start on a mini action plan, based on their discussion of the mentee’s goals and aspirations. 

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We then shifted gears with a ‘Human Bingo’ game; attendees were given bingo cards to identify individuals in the room that had particular job titles or business ventures, worked in specific industries, and more. This was a great opportunity to meet any attendees they may not have previously spoken to. The first two who completed this activity won a lovely gift basket full of goodies from Shoppers Drug Mart!

SheMentors Bingo activity

SheMentors Bingo activity

After some additional unstructured networking, Nora Cottrill, YWiB’s Content Coordinator, introduced the group to our online community platform, newly launched to support SheMentor matches. This forum is intended to unite attendees outside of the SheMentors events and facilitate more connections and opportunity sharing. Community members are also encouraged to share #SheCelebrates posts, including personal achievements and other exciting announcements.   

Lara and Sandra gave closing remarks and after a few group photos, everyone began to say their goodbyes. Our team was so happy to have completed a successful Matching Day, and we are excited for the potential of these mentorship relationships. We also want to thank Eureka Hub and their Community & Operations Manager, Avree Scarcello, for being so accommodating and providing and excellent space for our kick-off event!

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Stay tuned for more SheMentors updates and other events from YWiB! If you are interested in participating in our second cohort of our mentorship program, either as a mentor or mentee, please email us at SheMentors@ywib.ca for waitlist details.