I give an outline of what I want to do, and give some breadcrumbs for any relevant existing files that are related in some way, ask it to figure out context for my change and to write up a summary of the full scope of the change we're making, including an index of file paths to all relevant files with a very concise blurb about what each file does/contains, and then also to produce a step-by-step plan at the end. I generally always have to tell it to NOT think about this like a traditional engineering team plan, this is a senior engineer and LLM code agent working together, think only about technical architecture, otherwise you get "phase 1 (1-2 weeks), phase 2 (2-4 weeks), step a (4-8 hours)" sort of nonsense timelines in your plan. Then I review the steps myself to make sure they are coherent and make sense, and I poke and prod the LLM to fix anything that seems weird, either fixing context or directions or whatever. Then I feed the entire document to another clean context window (or two or three) and ask it to "evaluate this plan for cohesiveness and coherency, tell me if it's ready for engineering or if there's anything underspecified or unclear" and iterate on that like 1-3 times until I run a fresh context window and it says "This plan looks great, it's well crafted, organized, etc...." and doesn't give feedback. Then I go to a fresh context window and tell it "Review the document @MY_PLAN.md thoroughly and begin implementation of step 1, stop after step 1 before doing step 2" and I start working through the steps with it.
