I thought it was just lack of experience (on both our parts). My mom suggested I use a sturdier spoon and I was willing to try anything if it meant a cleaner baby and a cleaner high chair. I went out and bought some simple, cheap plastic spoons.
MAGIC! Mealtime mess has been cut down by at least 90%.
Gabriel really doesn't care what spoon I use as long as there's food on it! So for you new or soon-to-be mothers out there, take heed! The flexible silicone spoons are not worth the time, money, or frustration!