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roadmap

skill

the memory a long project keeps of itself

Keeps a running record of what a months-long project has decided and why, what's still genuinely open, and what was deliberately left off the table.

how it fires

You never type a command. Describe your problem in your own words and MasterMind recognizes it and applies this skill. Power users can invoke it directly with /roadmap.

the rule it routes on
Use when work spans weeks and the reasoning behind it is piling up: returning to a project after time away, "why did we decide X?", "where did we land on this?", "what's still open?", onboarding someone onto a long-running build, or a choice everyone remembers making and nobody can find. Not one session's state (that's `handoff`), not scoping one feature (that's `interview`).

🧠 MasterMind ▸ roadmap

what this skill does

This is the real text MasterMind follows: generated from the source, not a summary of it.

The problem this solves

Some work doesn’t finish in a session, or a week. It runs for two months across forty conversations, and by the end almost nobody can say why the important parts are the way they are.

The code survives. It’s on disk. What evaporates is the reasoning wrapped around it. Why the database was chosen over the obvious one. Which approach was tried in week two, cost three days, and failed. Which question is still genuinely unanswered versus which one somebody quietly answered in passing. That reasoning lived in conversations that have since been cleared, and it was the expensive part.

The damage shows up as a specific, repeatable event: someone: a teammate, a future session, you, looks at an unusual choice, concludes it looks wrong, and “fixes” it. The fix reintroduces the exact problem the original choice was avoiding, and the project pays for the same lesson twice.

Map is the file that stops that. One document the project owns, appended to as the work goes, built to answer “why is it like this?” months after the person who knew has stopped remembering.

What goes wrong without it

  • Decisions get relitigated. The same trade-off gets argued in week one and again in week six, usually landing somewhere different the second time, so the codebase ends up holding both answers.
  • A reversal erases its own history. Something is changed, the old note is tidied away to keep the document consistent, and the record now claims the current state was always the plan. The most valuable fact: that the ground moved, and when: is the one thing that got deleted.
  • The plan is fiction past week two. Asked to lay out a long project, an AI will produce a confident, complete-looking roadmap, including the parts it cannot possibly know yet. Invented structure reads exactly like decided structure, and the next session builds against it.
  • Out-of-scope work creeps back in. Something is explicitly parked. Weeks later, someone working nearby does it anyway, because nothing recorded that parking it was a choice rather than an oversight.
  • Onboarding costs a week. The new person can read every file and still not know which parts are load-bearing and which are leftovers.

How it actually works

MasterMind keeps one markdown file in the project with five sections, and each has a strict job.

Destination is what done looks like, in two or three lines. It’s short on purpose: it’s the thing every later decision gets measured against, so it has to stay readable in ten seconds.

Decisions so far is the heart of it: dated one-liners, each with its reason attached, each pointing at the spec or pull request or file where the detail actually lives. This section is append-only. When a decision is reversed, the old line stays exactly where it is and a new one is added that names what it reverses and what changed. That rule is the difference between a document that explains the project and one that merely describes it. An edited history can tell you the current state; only an intact one can tell you why the state moved, and why it moved is what stops the next person undoing it.

Open questions holds only things that can be stated precisely right now, even though they can’t be answered yet. “Which queue runs the nightly export?” qualifies. “How does billing work?” doesn’t: that isn’t a question yet, it’s a region of fog.

Not yet specified is where the fog goes, and it’s the section that keeps the map honest. It records known unknowns as a single line naming the unknown and what will eventually lift it. No speculative plan, no invented milestones. The governing idea is borrowed from a map-maker’s discipline: you do not chart terrain you have not seen. A blank region is information. A plausible guess drawn in the same ink as surveyed ground is a lie the project will later act on.

Out of scope records what was deliberately left out: and things don’t quietly graduate back in. Bringing one back is itself a decision, dated, with who asked and why now.

Two further rules keep it useful. The map is an index, not a store: it points at specs, PRs, and files rather than reproducing them, because a copy is always the version that goes stale. And one open question gets resolved per session: a session that closes five has been guessing at four, and guesses recorded as decisions are worse than no record at all.

When it fires

You don’t type a command. Say something like:

“remind me where we landed on the auth thing” “I’ve been off this project for a month: what’s the state of it?” “why did we decide to do it this way?” “Sara’s joining this next week, she needs to get up to speed”

You’ll see it engage in your terminal:

🧠 MasterMind ▸ picking the long thread back up: what we decided, what's still open
   └ roadmap · destination → decisions → open questions → fog

When it does not fire

  • Pausing in the middle of one task: that’s handoff. The difference is lifespan. A handoff is written for one specific reader picking up one specific unfinished thing tomorrow, and it’s thrown away the moment they do. A map is written for whoever shows up in four months, and it’s kept for as long as the project exists.
  • Working out what one feature should be: that’s interview. A spec decides a single ask in detail before anyone builds it, and retires when that thing ships. The map records only the one-line outcome and points at the spec for the rest.
  • Anything that finishes in a session or two. Nothing accumulates, so there’s nothing to accumulate into. The ceremony would cost more than it returns.

What you get

A single file that answers “why is it like this?” long after everyone has stopped remembering: with the reversals still visible, the genuinely open questions separated from the merely unexplored, and the parked work still visibly parked. It’s the difference between a project that compounds what it learns and one that keeps rediscovering it.