An iterative process for cognitive assessment of generated work products relies on a variety of assessors providing different granularities such as coarse, medium and fine, in combination with user guidance. A cognitive system generates candidates based on soft constraints such as user preferences. The candidates are analyzed using first assessors to compute preliminary scores which are ranked and presented to a user. Based on user selection/adjustment, the system generates a final work product which is analyzed using second assessors, and presents the final work product and final scores to the user. There may be multiple iterations of the user adjustment and refined presentation of final work products. The invention may be consummated by receiving confirmation of the final work product from the user, and taking some action such as electronically completing a purchase of a product or electronically reserving a third-party service.