Little By Little Program

Little by Little in Community is a free, co-ed group mentoring program delivered by Big Brothers Big Sisters of Toronto in partnership with Toronto Community Housing (TCHC). The program takes place directly within TCHC communities, making mentorship more accessible for youth and families.

Each program brings together approximately 10 youth and 2–3 trained adult mentors in a safe, welcoming, and inclusive environment where young people can build confidence, develop life skills, and create meaningful connections with positive adult role models.

Designed for youth ages 10–16, the program focuses on helping participants navigate the challenges of adolescence while building the skills they need to thrive. Through interactive discussions, hands-on activities, and mentorship, youth will explore topics including:

Building positive self-identity and self-confidence
Mental health and emotional well-being
Identifying and navigating risky behaviours
Healthy relationships and setting boundaries
Goal setting and future planning
Leadership, communication, and decision-making skills

Program Schedule

The program runs weekly from October 2026 through December 2027.

Why Little by Little?

Positive relationships can have a lasting impact on a young person’s future. Through consistent mentorship, supportive peer connections, and engaging programming, Little by Little in Community helps youth develop the confidence, resilience, and life skills needed to make positive choices and reach their full potential.

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.