Watkins tenure with the Chicago Public Schools has included teaching at  the Louis J. Agassiz and Arthur R. Ashe, Jr. Elementary Schools and serving as an administrator in the Chicago Public Schools' Office of Specialized Services. She is the recipient of several awards including the Golden Apple Award for Excellence in Teaching, Kathy Osterman Award for Superior Public Service and the Michael Jordan Education Club Teacher Achiever Award. Watkins is currently the principal of the John J. Pershing West Magnet School.