To qualify for the Misses of Missouri and Misses of Missouri Sweetheart Pageant, you must be the winner or the 1st Runner-Up in an official preliminary to the Miss Missouri Pageant, which for her was the Little Miss Jackson pageant that was held in November, 2007. It is run exactly like the Miss America pageant. Heather competed in private interview, physical fitness, evening wear, and sang "All for One" from the movie High School Musical 2 for her talent competition. Her winnings include a crown, trophy, sash, medallion, flowers, and a $50 savings bond.
Within the past year, Heather has won the the Scott City Summerfest pageant, Advance Labor Day pageant, Chaffee German Days pageant, and has placed in the Sikeston Cotton Carnival, Southeast Missouri District Fair, and the Malden SEMO Regional Scholarship pageant. She is the daughter of Richard and Donna Conaway of Jackson and will be in the first grade at South Elementary.