I agree.  When the position of the Church is that the hierarchy is always right, and that it's the job of the laity to listen, the hierarchy will not be prepared for any actual dialogue.  Moreover, when theologians are told (as they were during the past two pontificates) that the mere suggestion of alternate thought is not allowed, priests and hierarchy quickly learn that there is no room for dialogue. Sadly, many of the newer priests are thoroughly steeped in that view.  It will take many iterations of Cupich to change this.  
Too many younger (no longer really young) people have grown and are growing up with the belief that the Church is, at best, marginal in their lives.  I don't know if Cupich and those like him will be able to work quickly enough and with sufficient forcefulness to make any markable difference.  I hope that I am wrong.