Honest Planning Artifacts

The documents we create shape how people understand uncertainty. Here are alternatives to overconfident artifacts.

Traditional planning documents often:

- Present single-point estimates as if they were certain

- Hide assumptions

- Treat far-future items with the same precision as near-term

- Become outdated but stay authoritative

NOW/NEXT/LATER instead of dates:

- NOW: Actively working on

- NEXT: Coming up, planned but not started

- LATER: On our minds, but not committed

This signals decreasing certainty without pretending to know dates.

Confidence indicators:

- High confidence (committed, near-term, well-understood)

- Medium confidence (planned, some dependencies, mostly understood)

- Low confidence (exploratory, far-out, many unknowns)

Visual indication of how much to trust each item.

Named assumptions:

Every plan includes: "This assumes X, Y, Z. If those change, the plan changes."

Version dating:

Every artifact has a date and a note: "Reflects understanding as of X. Check for updates."

Instead of a roadmap, try a spectrum:

ThemeWhat we knowWhat we're exploringOpen questions

Theme 1Committed itemsPossible approachesWhat we need to learn

Theme 2.........

This makes uncertainty part of the artifact rather than something hidden.

Any planning artifact should be:

- Dated

- Easy to update

- Reviewed regularly

- Versioned or historied

A living document beats a beautiful but stale one.

The artifact is not the communication—it's a prop for the communication.

Every artifact should come with:

- What it represents (intent? commitment? exploration?)

- What it doesn't show (constraints, dependencies, uncertainties)

- When it will be updated

- How to flag concerns or changes

The conversation matters more than the document.