A situation where there is little to lose and lots of gain by shipping something fast.
HOW IT'S USEFUL
Freerolls typically emerge in product when the current user experience is so bad that by making any reasonable change based on intuition is likely to make it much better. They are different than fixing bugs because bugs refer to something that’s not working as designed.
If you’re in a situation where your team is thinking, “Let’s just do something… we can’t really make it any worse”, you likely have a freeroll in front of you.
(r/CrappyDesign on Reddit is a treasure trove of such situations)
—Brandon Chu