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2019-20 Staff Awards
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- Certified Master Athletic Administrator designation from the National Interscholastic Athletic Administrators Association — Kaleb Stoppel, Olathe EAst High School
- Kansas Outstanding Biology Teacher Award from the National Association of Biology Teachers — Andrew Taylor, Olathe Northwest High School
- A recipient of the 2020 Arts Inspired Network Courageous Creativity Challenge — Heather Schoonover, Community Development Office
- High School Middle School Athletic Director of the Year by the Kansas Interscholastic Administrators Association — Scott Appell, Pioneer Trail Middle School
- 2020 Presidential Award in Recognition of Exceptional Service to Children and School Psychology from the National Association of School Psychologists — Tyler Kitson, Fairview and Washington elementaries
- Elected as Southwest regional chair of the School Nutrition Association — Cindy Jones, Food Services
- Elected as national chair for Choral Repertoire and Resources on the American Choral Directors Association — Gretchen Harrison, Frontier Trail Middle School
- Spirit of Education Award from National Safe Schools Convening — Jessica Sadler, Oregon Trail Middle School
- Elected as a representative at large for the National Council for the Social Studies — Tina Ellsworth, District K-12 Social Studies Coordinator
- One of eight 2018-19 Sectional Coaches of the Year as named by the National Federation of State High School Associations — Mallory Krug, Olathe district gymnastics coach
- Inducted in the Kansas Thespians Hall of Fame — David Hastings, Olathe South High School
- Kansas Thespian Region 2 Teacher of the Year — Dustin Pence, Olathe North High School
- Kansas Horizon Award — Bennett Johnson, Heritage Elementary School; Samantha Collins, Chisholm Trail Middle School
- Kansas 6A Girls Cross Country Coach of the Year from the Kansas Track and Field and Cross Country Association — Kelsey Carbajo, Olathe West High School
- Coach of the boys West Team in the 2019 High School All-American Game — Terry Hair, Olathe East High School
- Earned Certified Athletic Administrator status — Kaleb Stoppel, Olathe East High School
- 2019 High School Teacher of Excellence Award from the Secondary Section of the National Council of Teachers of English — LuAnn Fox, Olathe Northwest High School
- 2019 Distinguished Service Award from the Kansas School Public Relations Association — Maggie Kolb, Education Center
- Certificate of Excellence for the 2017-18 annual report and a Certificate of Merit for the district's social media platforms from the Kansas Association of School Boards and Kansas School Public Relations Association — Cody Kennedy, Education Center
- Certificate of Merit for "Azalia's Story" video from the Kansas Association of School Boards and Kansas School Public Relations Association — Tony Rangel, Technology Support Center
- Certificates of Merit for the 2019-20 parent guide and the winter 2018 edition of School News magazine — Communications Division
- One of three Outstanding Recent Graduates from Emporia State University's College of Liberal Arts and Sciences, The Teachers College, and the School of Business — Josh Stock, Santa Fe Trail Middle School
- 2019 Kansas Social Studies Teacher of the Year — Ashley Umphrey, Chisholm Trail Middle School
- 2019 Educator Award from the Olathe Human Relations Commission — Phillip Simons, Olathe North High School
- 2019 Humanitarian Award from the Olathe Human Relations Commission — Angie Powers, Olathe Northwest High School
- President of the American Association of School Personnel Administrators — Cathy Donovan, Education Center
- Emporia State University Athletics Hall of Fame — Bree Beattie-Ederer, Olathe North High School
- "Baseball America" Assistant Coach of the Year by the 2019 American Baseball Coaches Association — Derek Leppert, Olathe West High School
- 2019-20 Outstanding Overall Art Educator of the Year by the Kansas Art Education Association — Megan Wendleton, California Trail Middle School