City Leader and President of the Northiside Development Group, Mr. Bill Barnet, has been instrumental in the gains taking place at The Cleveland Academy of Leadership.

In 2011, Cleveland Elementary transitioned to a Leadership Academy adopting The Leader in Me eucation model based on Stephen Covey's, The 7 Habits of Highly Effective People. The Leader in Me initiative promotes and challenges each student to become a leader. The entire school community incorporates the 8 habits in all daily work and activities as well as their personal lives. Cleveland Academy was the first school in South Carolina granted permission to add extended mandatory days to its academic calendar. The added weeks of instuction are heavily focused on literacy and math. Students attend school an additional 15 days (195 in total) and teachers work an additional 15 day contract.

In November 2013, Cleveland was distinguished as a Leader in Me, Lighthouse School - joining one of only 103 other schools in the world (at the time) with Lighthouse School status.