How to think in Pencil

Most planning tools let you put work anywhere. That flexibility is the problem — six months in, you have epics inside stories inside initiatives inside themes and nobody remembers why. Pencil picks the shape for you. There are four levels, they nest one way, and the nesting is the meaning.

The four levels

• Product — something you ship to people. "The web app." "The CLI." Most teams have one to three.
• Feature — a capability of the product, big enough to be worth describing in prose. "Self-serve billing." "Offline mode."
• Iteration — a thin vertical slice of a feature that you can finish, ship, and learn from. "Self-serve billing — Stripe Checkout for solo plan, no team plan, no proration." If you can't ship it, it isn't an iteration; it's a wish.
• Task — a unit of work that fits in one person's head. If you'd describe it to a teammate in one sentence, it's the right size.

Two rules that make the model work

Rule 1: An iteration must be shippable. If the iteration ends and you can't put it in front of a user (real or internal), it wasn't a slice — it was a milestone. Milestones are fine, but Pencil tracks them as goals, not iterations. Iterations are the unit of "we made something better today."

Rule 2: A task is for one person and one sitting. If a task needs three people or three days, it's actually a small iteration. Split it.

Features vs tasks: when in doubt

If the work needs a paragraph to explain, it's a feature. If it needs a sentence, it's a task. The PRD/FRD writer in Pencil is your tell — if you'd want to draft a spec for it, it belongs as a feature with iterations underneath. If a spec would be silly, it's a task.

Where bugs fit

Bugs are first-class — they don't pretend to be tasks. A bug has a severity, a status, and a tie back to the feature it broke. The rule of thumb: anything a user could report as "this is wrong" is a bug. Anything a teammate would describe as "we should also do X" is a task.

When a bug is bigger than a fix — when fixing it properly means redesigning something — promote it to a feature and close the bug with a link. Don't accumulate "bug" entries that are really backlog.

What to try next

Read Writing features and specs to see how the PRD/FRD tools help you turn a feature into something you can actually start work on.