OLLI-Mason holds its annual election for one third of the Board of Directors in the spring of each year. At its first regular meeting following the annual election of Board members, the new Board meets to elect the president and other officers (vice president, treasurer and secretary) for one-year terms, effective immediately. Here is a list of all OLLI-Mason presidents since OLLI's founding as the Learning in Retirement Institute in 1991.
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- Kathryn Brooks, 1991/1992
- Shirley Fox, 1992/1993
- Lilyan Spero, 1993/1994
- Laura Cambern, 1994/1995
- Laura Cambern, 1995/1996
- Janice Dewire, 1996/1997
- Janice Dewire, 1997/1998
- Michael Styles, 1998/1999
- Ray Beery, 1999/2000
- Ed Mentz, 2000/2001
- Ed Mentz, 2001/2002
- Bob Bohall, 2002/2003
- Bob Bohall, 2003/2004
- Charles Duggan, 2004/2005
- Charles Duggan, 2005/2006
- Deborah Halverson, June 2006 – June 2007
- Deborah Halverson, June 2007 – August 20, 2007
(resignation) - Ben Gold, August 20 – August 31, 2007 (vice president serving as acting president, pending election of president)
- Pat Carroll, August 31, 2007 – June 2008
- Pat Carroll, June 2008 – June 2009
- Emmett Fenlon, June 2009 – June 2010
- Manuel Pablo, June 2010 – June 2011
- Manuel Pablo, June 2011 – June 2012
- John Woods, June 2012 – June 2013
- Martha Scanlon, June 2013 – June 2014
- Glenn Kamber, June 2014 – June 2015
- Glenn Kamber, June 2015 – June 2016
- Ray Beery, June 2016 – June 2017
- Ray Beery, June 2017 – June 2018
- Bill Taylor, June 2018 – June 2020
- Paul Howard, June 2020 – Updated: November 4, 2020