Here are some recent videos from WordCamp Europe 2014 covering the past, present, and future of WordPress development.
Matt Mullenweg: Q&A with Om Malik
Matt Mullenweg, the founder of WordPress, in conversation with tech writer Om Malik on the WordPress past and present, as well as where we are going for the future.
Andrew Nacin: Post-Modern WordPress
Andrew Nacin, lead developer for the WordPress open source project, discusses the philosophy of WordPress development, and the course it should and will take to keep growing.