Big Moments

Mentees (Littles) and Mentors (Bigs) are matched for a minimum of 1 year. On average, formal matches under our guidance last for 3 years but relationships continue for years afterwards. The pair spend approximately 1-2 hours per week together, equating to approximately 300 hours over the course of a typical match.

During these dedicated weekly meetings, matches take part in a variety of activities that are co-created by the pair. Supporting our matches through symbolic giving to activities highlighted on this page will make a huge impact on the match and allow Bigs and Littles to keep learning together.

Meal for a Match

Whether it is going out to eat at a nice restaurant or preparing a meal, BIGS and Littles have used food to engage and start conversations. With rising food costs in Toronto, food insecurity is a BIG issue for our Littles. The opportunity to cook a meal or eat out is often a BIG moment for our youth. Help support this moment for a match!

Art of a Match

Matching a Little to the right BIG is truly a science, and some can urge an art. But when you see the crafts, drawings, dances, sewing and all things creative that matches do together, there is definitely an ART of a match. Help support the artistic direction of our youth.

Game.Set.Match

A common and exhilarating moments for matches are playing sports together or attending a game in Toronto. Whether it’s a Raptors, Maple Leafs or a Blue Jays game, fun is always had! Being together with other fans, enjoying game day snacks and seeing the sport live is always a cherished moment.

STEMming from a Match

Help create a big moment through science, technology, engineering and math activities. Participating in STEM activities sparks curiosity. Having a tablet to learn to code or creating rainy day activities such building a volcano and seeing it erupt are all part of this moment.

Siobhan Calderbank's Bio

Siobhan Calderbank is an award-winning keynote speaker, leadership strategist, and Talent & Human Resources Executive with more than 20 years of experience transforming organizations, building inclusive cultures, and developing diverse leadership pipelines. Currently serving as Vice President, Talent & Performance Management at Element Fleet Management, she is recognized for leading large-scale organizational transformation, advancing talent and leadership strategies, and helping organizations build high-performing, future-ready teams.

Recognizing the need for greater access to mentorship and leadership development, Siobhan is dedicated to empowering women and youth, particularly those from underrepresented communities, through coaching, career development, networking, financial aid, and leadership-building opportunities. Her commitment to creating pathways for others to succeed is reflected in her extensive mentorship, community leadership, and advocacy efforts focused on supporting youth, women, newcomers, and emerging leaders.

As a globally recognized speaker, Siobhan has inspired audiences from more than 70 countries through conferences, corporate events, and leadership forums. She is a published author and contributor featured alongside influential thought leaders including Oprah Winfrey, Maya Angelou, John Lewis, and Deepak Chopra. Her thought leadership on leadership, change management, inclusion, and talent development has been featured across numerous publications and media platforms. Her voice has been featured on ABC, CBS, NBC, FOX, and CW, and she has appeared on Reuters and Nasdaq billboards in Times Square, as well as Planet Hollywood in Las Vegas.

Siobhan has held several leadership and advisory roles supporting diversity, inclusion, mentorship, and community development initiatives. Her contributions have been recognized through numerous honours, including being named one of the Top 100 Accomplished Black Canadian Women, receiving the Women of Inspiration Award for Diversity and Inclusiveness, and being recognized as one of the Top 100 Black Women to Watch in Canada.

She holds a Master of Arts in Leadership from Royal Roads University, a Certificate in Advanced Human Resources from Queen’s University, and a Bachelor of Commerce in Information Technology Management from Toronto Metropolitan University. Through her professional leadership and community service, Siobhan remains committed to helping individuals realize their potential and creating opportunities that enable future generations to thrive.