Sometimes when you feature many posts at once by ticking Make this post sticky button in all posts quick edit section then what WordPress by default does is that it shorts those sticky posts in date wide order which simply means if you make many posts sticky then your most recently posted sticky post will be coming on top. This tutorial explains you how you can manually sort and rearrange sticky posts in your WordPress site easily.
Install and activate Sortable Sticky Posts. Using this new WordPress plugin you can sort all your sticky posts using AJAX based drag and drop interface. After activation visit your admin area Dashboard -> Settings -> Reading, scroll down to reorder stickies and rearrange all your sticky posts in the order you want.