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Plans Are Disposable, Skills Are Durable

July 29, 2026

The Problem

We wrote about our planning skill back in February. That post covered how to write a plan: a markdown file in plans/, an index for navigation, and a rule that you delete the plan when the work ships.

Five months of running that system across three Hello Weather repos surfaced everything the first post didn’t cover — not how plans are born, but how they live and die:

  1. Docs rot. A plan written in March cites app/models/thing.rb:117. By June that line is 145, the method was renamed, and the “current” library version in the plan is two majors stale. An agent implementing from that plan will confidently build the wrong thing.
  2. Sessions end. The agent that wrote the plan has all the context. The agent that implements it three weeks later has none, and may be a smaller model. Anything the plan leaves implicit becomes an exploration tax paid on every read.
  3. Agents always find something to do. Ask an agent “what’s next?” and it will answer. It will always answer. If the honest answer is “nothing, wait for the trigger,” an agent without an explicit rule authorizing that answer will invent work instead — usually a refactor, usually the most expensive option on the table.
  4. Plans accumulate. One repo reached 135 plan files. Many self-labeled Status: Implemented or “durable record” — and those labels are exactly why nobody deleted them.

The fix wasn’t a better plan template. It was a lifecycle policy: rules for what a plan must contain, when it must die, what survives it, and what the index is allowed to say.

The Lifecycle

Research → Write (handoff-ready) → Rank in the index → Implement
    → Migrate durable knowledge into a skill → DELETE the plan → Update the index

The taxonomy that makes this work has three document types, and confusing them is the root of most doc rot:

Type Lifespan What it holds
Plan One-shot — deleted after it ships This specific change: steps, verified paths, success criteria
Playbook Permanent, versioned A procedure that recurs verbatim per instance
Skill Permanent, versioned A workflow, plus the invariants and gotchas plans leave behind

Plans are scaffolding. Skills are the building. Playbooks are the jig you keep in the shop because you’ll cut this joint again.

Ground Truth: Write for a Reader Who Won’t Explore

Every plan now carries a ## Ground Truth section. The standard is explicit in all three planning skills:

Write plans so a less capable model can implement them without exploring the codebase.

That last clause is the whole design constraint. If the implementer has to grep to find where things register, the plan has failed — and a smaller model may grep, guess wrong, and ship the guess.

Four rules make a Ground Truth section actually load-bearing:

1. Cite verified paths with line numbers.

A real Ground Truth section, verbatim except for the header:

Ground Truth (codebase-verified 2026-06-11)

Key files

File Line Purpose
app/models/api/weather.rb 26-27 Coordinate truncation: truncate(3)

Current implementation

# app/models/api/weather.rb:26-27
@lat = (@args[:lat] || @source_class.default_lat).to_f.truncate(3)

Change required: truncate(3) → truncate(2) on both lines.

The skill’s rule: never cite a symbol you haven’t confirmed exists. The section header carries the verification date so a stale citation is visible rather than merely wrong.

2. Name the registration points. The expensive part of an unfamiliar codebase isn’t the new file — it’s the four places you have to register the new file. A pass across 32 plans in the web repo added exactly that: key-files tables, the constant lists a new entry lands in, the factory method that maps a name to a class. That pass also corrected patterns the plans had invented — a base class that didn’t exist, an environment-variable lookup where the codebase used a helper. Plans written from memory hallucinate house conventions; plans written against the source don’t.

3. Date every external fact with a Verify: marker. Anything the codebase can’t confirm — library versions, upstream payload shapes, platform policy deadlines, pricing — gets flagged inline:

| cloud_cover | `cloud_cover` (%) | Recorded; `Verify:` 0-100 integer encoding per the API spec |
| alert id | `Verify:` exact key name (`id` vs `alert_id`) | Verify |

The skill states the principle directly: never present external facts as timeless — date them and flag them for re-checking. And the implementation checklist has a matching step: resolve Verify: markers before building on them. A marker that survives to code review is a bug in the review, not the plan.

4. Mark what’s cuttable. When a plan feeds a deadline-bound release, each item is labeled required or cuttable:

Effort honesty: mark items cuttable vs required when they feed a release block, so time pressure cuts the right things.

Under time pressure something gets dropped. The only question is whether the person dropping it has the author’s judgment available. This is also why one release block ends with an explicit anti-list — “Explicitly NOT required for this release (common trap — these feel related but aren’t)” — followed by six tempting adjacent upgrades. Naming the trap is cheaper than re-litigating it every session.

One more rule keeps Ground Truth honest at implementation time:

If the plan conflicts with existing patterns — follow the patterns, update the plan. The codebase outranks the plan when they disagree.

Deletion: A “Record” Label Is a Delete Signal

The February post said “delete when done.” The rule that survived contact with 135 files is sharper:

A plan is removed once the work it describes is fully implemented / shipped, or it is a completed one-time analysis — regardless of what the plan calls itself. A “Status: Implemented”, “implementation record”, “durable record”, or “reference” self-label is not a reason to keep a plan; it is a signal to remove it (after migrating anything durable).

That inversion is the useful part. Documents don’t self-label as records because they’re valuable; they do it because someone finished the work and felt bad deleting the file. The label is sentiment, not classification.

Only three things justify keeping a plan:

  1. Future / unstarted work — not built yet.
  2. Triggered / dormant work — reopens on a monitoring or external trigger, and the plan still holds the live reopen playbook.
  3. An active in-flight decision — pending actions or dates.

Anything else is done → migrate, then remove. Being linked from the index is not a reason to keep; that’s circular. And there’s a deliberate asymmetry for genuine uncertainty: when uncertain, prefer keep and say why — deleting curated plans is the risky direction.

Migrate before you delete

Nothing gets deleted until its durable knowledge is rehomed, preferably into a skill:

Durable knowledge a finished plan holds — non-obvious decisions, API facts and gotchas, operational procedures, hard-won rationale — must be moved into the relevant skill before the plan is removed. Never keep a plan alive just to hold reference material, and never delete without first rehoming what’s worth keeping.

The web repo’s big pass removed 35 plans in one pull request and migrated their contents into a dozen skills. What moved was the stuff that outlives the change: negative results (three optimizations that didn’t work, so nobody tries them again), upstream API quirks, capacity thresholds and their reopen gates, rejected vendor evaluations. What got deleted was the narrative of how we got there.

The method mattered as much as the outcome. A multi-agent audit classified all 135 plans, then adversarially verified every removal candidate — a second agent arguing the keep case against the first agent’s delete recommendation. Migrations and inbound-link repointing fanned out one agent per file. Then integrity was checked by script, not by eye:

# Orphans: a plan file the index doesn't point to is a bug
for f in plans/*.md; do
  b=$(basename "$f")
  grep -q "$b" PLANS.md || echo "ORPHAN: $b"
done

Link rot is the known failure mode here — an earlier round of deletions left 15 dangling links across surviving plans. So removal has a mandatory step before rm:

# Find every plan linking to the one being removed, redirect them in the same commit
grep -rln "plan-name.md" plans/

Both directions get checked: no orphans (a plan nothing points to), no dangling links (a pointer to nothing).

The Index Is a Ranking Surface, Not a Document Store

PLANS.md had grown to 380 lines of duplicated prose. The policy that cut it in half:

PLANS.md is a navigation and ranking surface, not a document store. Duplicated prose goes stale the moment the underlying plan moves.

  • Every entry is 1–3 lines + a link. If you’re writing more than that in the index, the extra belongs in the linked plan.
  • No implemented-work tracking, dated pass logs, or history in the index — record only the current state and what’s remaining.
  • Status updates replace, they don’t accrete. When state changes, rewrite the entry’s current-state line; don’t append another dated bullet under the old ones.
  • Content with no plan doc to link to stays very concise. If it needs more, create the plan doc and link it.

“Replace, don’t accrete” is the rule that does the work. The natural failure mode of an agent updating a status file is appending — it’s safer-feeling, it preserves history, and it turns a 3-line entry into a 40-line changelog nobody reads. Dated history is fine inside an in-flight plan, because it dies with the plan.

The same restructuring moved per-item status boards next to the procedure they describe. A multi-step rollout used to tick progress in the central index; now the board lives inside the runbook that documents the steps, and each rollout PR updates its own line in its own diff. Procedure and state in one document, updated by the change that alters them — instead of two documents that have to be kept in sync by discipline.

Every plan also needs a ranking slot, not just a catalog line:

Every plan creation/removal MUST update PLANS.md — both the Plan Catalog entry AND its slot in the ranking machinery (a release-block item, a Triggered Work row, or a Not Next row with an explicit reopen condition). A plan that exists only in the catalog has no priority and will never be picked.

The What’s-Next State Machine

The most interesting piece. The Android index answers “what’s next?” with a deterministic four-step check:

### What's Next Rule

1. Check **Hard Deadlines** — anything due within ~90 days that isn't
   already in an active release block?
2. Check **Recurring Work** for any row with `Next due` on or before today.
3. Check **Triggered Work** for any fired trigger.
4. Otherwise: work the first unchecked item in the lowest-numbered
   **Release** block. If all release blocks are done, this repo is
   idle by design — confirm against the cross-repo index before
   starting anything in **Not Next**.

Step 5 is the point of the whole thing. The skill spells out the obligation:

If all release blocks are complete, [the repo] is idle by design — check the cross-repo index before proposing anything from Not Next, and say so explicitly rather than inventing work.

This is planning for an agent that will otherwise always find something to do. “Nothing” is a legitimate terminal state, and the system has to authorize it explicitly, because the default behavior of a helpful model asked for a recommendation is to produce one. Left unconstrained it will propose the framework migration.

The Not Next table is what keeps deferred work deferred. Every row carries a reopen condition, not a vibe:

Work Reopen when
Modernization track (language/DI/toolchain majors) Feature investment reopens, or a required library forces it (none currently does). Order inside the track is fixed by hard dependencies.
Map-rendering rewrite The packaging-compliance check fails (→ jumps into the active release), the vendor SDK breaks or EOLs, or feature investment reopens
Localization Phase 2 (native UI chrome) Only when the platform decision lands and Phase 1 has shipped — highest throwaway of the three phases

And a matching hard rule: never propose Not Next work as next — its reopen condition has to fire first. Without that, “not now” degrades into “not now, unless the agent is feeling ambitious,” which is not a policy.

Triggered and recurring work are first-class rows, not afterthoughts:

## Triggered Work

| Trigger | Action |
|---|---|
| The API ships a new upstream provider | Add it via the integration playbook — small, mechanical, visible product win |
| The packaging-compliance check fails | Escalate the rendering migration into the active release |
| 30 days after Release 1 | Re-triage surviving crash groups; write new plans only if a signature dominates |

## Recurring Work

| Workstream | Cadence | Next due |
|---|---|---|
| Platform compliance check | Annually, every June (deadlines land Aug 31) | 2027-06-01 |
| Crash triage | After each release reaches ~50% rollout; otherwise quarterly | After Release 1 ships |
| Plans index review | After any release or material re-rank | After Release 1 ships |

Both tables answer the same question a stale todo list can’t: is this actionable today, and if not, what exactly would make it actionable? When recurring work completes, updating its Next due is part of the same change — the schedule can’t drift from the work.

The cached answer lives at the top of the index as a What’s Next section, and the skill says when to distrust it: re-derive only when a checkpoint arrived, a trigger fired, or the user asks for fresh eyes. Otherwise, read the cache. Re-running full triage on every question burns context to arrive at the same answer.

Playbooks: The One Exception to Deletion

One document in the Android plans/ directory is permanent, and it’s explicit about why:

This playbook stays in plans/ permanently as a living checklist (unlike one-shot plans, it is reused per source, not removed).

It’s an integration playbook for adding a normalized upstream provider — the task where a server-side API normalizes every provider to one schema, so the client work is identical every time. Its shape is the interesting part:

The test for whether something is a playbook rather than a plan: will this exact procedure run again, verbatim, for the next instance? If yes, it survives the work. If the answer is “well, something like it,” that’s a skill — the workflow generalizes but the steps don’t. If it runs once, it’s a plan, and it dies on merge.

Note that a playbook is not a plan with a longer life. Its content is different: a plan has this change’s steps and success criteria; a playbook has the invariant surface and the checklist you re-paste. Writing a plan and then declaring it permanent is how you get the 135-file directory.

Lessons Learned

How This Post Was Made

Prompt 1: “it’s been a while since we added any blog posts, see recent work in the ~/Code/helloweather projects, dispatch opus agents to search for interesting stuff that we’ve done since the last blog post, perhaps one or more agents per repo, then review and consider and come up with a proposed list of blog posts we might consider.”

Prompt 2: “draft posts for [the approved shortlist] – create one pr for the repo main / skills update we just did, then one pr per post for the approved list”

Research by one Claude agent per repo mining git history since the previous post; this draft was written by a dedicated agent from that research plus the underlying skill files and plan indexes, then reviewed before publishing.