Illinois Aviation Academy Instructor Sydney Pilling Recognized by AOPA with 2026 Flight Training Experience Award

February 23, 2026

Q: What does this AOPA recognition mean to you as a CFI? 

As a flight instructor, we all strive to ensure we are doing our best for our students. After lessons, I regularly invited feedback from both students and coworkers to improve my own knowledge and teaching ability. 

I see this award as another form of feedback. It is incredibly rewarding to know I’ve been part of my students’ training journeys and their success. That, more than anything, is what makes this recognition meaningful. 

Q: What did you enjoy most about instructing at Illinois Aviation Academy? 

I have always said my favorite part of IAA is the people! 

I had the opportunity to work within such a diverse aviation community. I enjoyed sitting in on other instructors’ lessons to see how their teaching styles and lesson plans differed from mine. There is always something to learn from one another. 

My students were some of the hardest-working individuals I have ever met. It was a privilege to fly with them, and I know many of them will become phenomenal instructors themselves. 

Q: How do you help flight students build confidence when starting flight training? 

One of the ways I supported student development was by maintaining a group chat for my Commercial and CFI/II students. I would share upcoming lessons that were open for observers, allowing students to sit in on ground sessions, simulator training, and flights. 

Commercial students benefited from additional ground instruction, while CFI/II students gained valuable experience teaching real students in a supported environment. I would sit in the back and assist if needed, helping them build communication skills and confidence before working independently with their own students. 

This collaborative environment strengthened not only technical knowledge, but also leadership skills. 

Q: Is there a student success moment that stands out to you? 

There have been many meaningful moments, but my favorites have been working with CFI/II applicants. 

I had the privilege of training these students, mentoring them through the application process to work at IAA, and then seeing them become my coworkers. Later, as a Check Instructor, I evaluated the students they trained. 

Seeing my students become instructors — and then watching their students succeed — was the most rewarding moment of my flight instructing career. It represents the true legacy of aviation mentorship. 

Q: What advice would you give future pilots training at IAA? 

I used to tell my students, “Pilots are people, and being a person comes first.” 

Flight training is exciting, but it is also hard work. The students who show up on bad weather days for ground lessons and extra simulator practice are the ones who succeed. 

At the same time, take care of yourself both inside and outside the airplane. 

For CFI/II students and newly hired instructors, my advice is simple: 

• Listen first, then talk. 

• Ask for help when you need it. 

• Be the first to admit when you are wrong. 

Your students are watching you. What kind of instructor do you want them to see? 

It is an incredible honor Sydney received as a representative for the Great Lakes Region and Illinois Aviation Academy/Spartan Education Group at the national level. We look forward to cheering on our instructor and celebrating this achievement alongside the broader aviation community!