Gumshoe RPG has the Preparedness skill that helps minimize planning and maximize execution. I'm fuzzy on the details though. I don't remember if it just gives you access to equipment in hindsight or if it gives you more freedom on what you planned. Dusk City Outlaws and I think Blades in the Dark have a similar planning mechanic to address this issue.
I wish that had made it into Trail of Cthulhu.