He is progressing, but Poles has to give him more weapons he can trust around him. Knowing he can risk a throw will help him in his progression. You see it on those improvised scramble plays... Nobody open, nobody to trust and the OL is not holding anything. He has to make that decision all by himself then and most of the time it won't work.
Throw on first down more often. I saw a graph that shows the Bears throw less on first down than any other team. Josh Allen, Mahomes, and Herbert do it the most.