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The concept of a professional development organization in Canada started with Alberta Schools Athletic Association (ASAA) ,Executive Director, John Paton. In 2008 the ASAA member schools voted to create a new professional development organization called the Alberta Interscholastic Administrators Association (AIAAA) that was modeled after the US athletic administrator's association, the NIAAA. Many discussions and meetings were held and the process of formalizing the organization began with electing a Board of Directors and creating Canadian course content for Leadership Training Program Courses. 

The first Canadian Leadership Training Program Courses were delivered in Banff, Alberta in 2009 to approximately 120 people. Feedback from the courses was outstanding and reaffirmed the need for professional development for Athletic Directors in Canada. Following the success of the first course deliveries, work began creating more courses and developing instructors. 

John saw the importance of the association and wanted to see it grow to support Athletic Directors across Canada. He presented annually to the School Sport Canada delegation, which included all of the school sport association Executive Directors from across Canada. After many presentations, in 2011 a motion was passed for School Sport Canada to support in principle the development of initiatives aimed at supporting school Athletic Directors. In 2012 Saskatchewan created the Saskatchewan Interscholastic Athletic Administrators Association (SIAAA) and began offering Leadership Training Program Courses in their province. 

In 2013 the AIAAA met and discussed the creation of a National Athletic Directors Association as a duplication of effort was happening between the AIAAA and SIAAA. The Canadian Interscholastic Athletic Administrators Association (CIAAA) was officially launched in June of 2013 with the association taking over a number of responsibilities for the entire country. Scott Bezubiak was elected to fill the role of President in 2014 and lead the organization.

The AIAAA (CIAAA was not formed yet) began talking about partnering with Universities to open the door for for school Athletic Directors to have access to Masters Degree programs in school athletic administration similar to the NIAAA. Approval was received for Masters programs through Indiana State University and Grace College in 2012 and work began to move from talk to action.The first students were admitted to the program in September 2014. The program took off  at Grace College, and the program was successfully approved for salary purposes in Ontario, BC, Manitoba, Alberta, and Saskatchewan. Due to the relationship between attainment of a Masters Degree, demand for the CIAAA's programming increased dramatically as a result of the salary-approved university degrees. 

Despite several years of presentations to the Executive Directors and Presidents of Canada's provincial and territorial school athletic associations, gaining traction across the country has been a challenge. Leadership Training Courses were being offered in several provinces but there was no-one who pursued the initiative to expand offerings. 

After continuing conversations and course deliveries, in 2019, the CIAAA and BC School Sports signed an MOU to become the third province to be a member of the CIAAA. This partnership brought over 400 new members to the CIAAA as well as further financial support. In September 2022, the PEISAA Signed On as a Partner Province. The CIAAA now has four official partner provinces, Alberta, BC, and Saskatchewan & Prince Edward Island. 

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