The ApproachThe ApproachThe multi-week narrative roadmap — titled weekly outcomes ("The one where…"), each with a demo, planned backwards from success. is the multi-week narrative roadmap for an initiative — deliberately loose at the edges and revised every week. Where the Initiative DocumentInitiative DocumentThe PR/FAQ-shaped document where an initiative's context lives — customer, solution, plan, business case, and success metrics. captures what and why, the Approach captures when: it turns the north star into a story the team can walk, one week at a time.

The sliding window

You cannot plan twelve weeks at the same resolution, so don’t. Detail the next 6–12 weeks week by week. Beyond that, drop to months for the following quarter, then to quarters, then to halves. The window slides forward each week — near weeks sharpen as far weeks approach. This is what lets the plan be both long-range and honest.

Plan backwards

Start from the end, not the start. The last week’s outcome is success as stated in the Initiative Document. Title that week, then move backwards one week at a time, asking what must already be true. The plan is a hypothesis about the path, not a contract.

”The one where…”

Every week gets a title — “The one where we validated with 10 users,” “The one where we shipped v1.” Read end to end, the titles should tell a coherent story. If they don’t, the plan wanders, and so will the team.

Each week also gets a demo definition: the concrete thing you will show the Product BoardProduct BoardTwo or more stakeholders who see the team's weekly demo and coach it — the human in the loop, with no single lead. at the end of the team’s week. A week without a credible demo is a week without an anchor.

The Approach as an uncertainty schedule

Assign each UncertaintyUncertaintyWhat the team does not yet know — sized and tracked deliberately rather than hidden inside estimates. from the Uncertainty ListUncertainty ListThe team's living list of open unknowns — sized 1/3/5, phrased as questions, reviewed daily and in planning, chipped away each week. to a specific week. That week’s job is to reduce it — as a Things to Figure OutThings to Figure OutEach person's one thing to figure out today, framed as a Why/How/What/When question that resolves into a Lesson Learned. (TFO) or as a weekly demo objective. This is what makes discovery and delivery happen in parallel: the Approach isn’t only a delivery plan, it is a schedule for chipping away at what the team doesn’t yet know.

Tracks and Weekly Goals

Optionally, group work into tracks — logical workstreams of things that belong together, such as Design, Frontend Engineering, Backend, or Research. Each person lists their outcomes per track per week. Within each week the team commits to a small set of Weekly Goals it believes it can finish at roughly 75% of capacity, leaving a quarter for the unknown.

Assign each activity either to a week or to the Daily Check-inDaily Check-inA 15-minute daily ritual where the team surfaces reality and unknowns rather than reporting status., and assign it to a person with an @ so ownership is never ambiguous.

Waiting for Answers

Some work stalls on a decision or input you don’t control — another team, a vendor, a legal sign-off. Track those external waits in a dedicated Waiting for Answers section rather than letting them rot inside a week. “Will Marketing help generate traffic in weeks 20–24? (waiting for answer)” The point is to make the wait visible and chase down what reduces it, not to file it and forget.

Tricks of the trade

A few habits separate a plan that gets used from one that gets ignored:

  • Start by listing what you don’t know yet. Before you draw a single week, write out the Uncertainties. The plan is, in large part, a schedule for reducing them.
  • Plan backwards from where you’re successful. If success is “conversion up by 5%,” leave the time at the end to actually test efficacy — don’t let the measurement be the thing that gets squeezed.
  • Give every week a title so the plan reads like a story of weeks.
  • Group work into Workstreams that belong together so the plan is legible at a glance.

Refinement levels: L0 to L3

An Approach starts early and unrefined and grows up as the initiative does.

  • L0 — Inception. Just the Initiative AuthorInitiative AuthorThe person accountable for an initiative's context — they write and keep the Initiative Document honest. sketching the shape.
  • L1 — Solution. Product and UX heavy; a smaller team firming up the storyboard and the early weeks.
  • L2 — Transition. Engineering heavy; the full team, plan filling in.
  • L3 — Delivered. Sales and marketing heavy; the full team taking it out.

The Basic Approach Plan — a leaner alternative

You don’t always need tracks and a sliding window. A smaller or earlier initiative can run on a Basic Approach Plan — the same thinking, fewer moving parts:

  • A disclaimer at the top. State plainly that the plan will change and that it is not a customer promise unless something is explicitly marked as one. This buys the team the freedom to learn.
  • Helpful links — the assets, the business case, the press release.
  • Uncertainties — checkbox questions such as “Will our target users want to use this?”
  • Week Plan — the weeks themselves, each titled “Week 16 (#1): The one where…”
  • Impediments — including external waits: “Will Marketing help generate traffic in weeks 20–24? (waiting for answer).”
  • Lessons Learned“Plan user interviews well on time.”

Keeping it current

A stale Approach is worse than none — it lies. Update it in Week Planning, every week: if titles or goals shift materially, the Approach shifts with them.

Template

Outcome (from the Initiative Document): the last week’s result = success

Tracks (optional): Design / FE / BE / Research…

Week-by-week (next 6–12 weeks, planned backwards):

  • Week N — “The one where…” — demo: …
  • Week N-1 — “The one where…” — demo: …

Then (coarser): months → quarters → halves

Uncertainties assigned to weeks: uncertainty → week it gets reduced

Waiting for Answers: external wait → who owns it → what reduces it

This week’s Weekly Goals: what we commit to, at 75% capacity

Fill-in template — Basic Approach Plan

For a smaller or earlier initiative, copy this leaner block instead.

Template

Disclaimer: this plan will change; it is not a customer promise unless marked as one

Helpful links: assets, business case, press release

Uncertainties (checkbox questions):

  • Will…?

Week Plan:

  • Week N (#1): “The one where…”
  • Week N+1 (#2): “The one where…”

Impediments / Waiting for Answers: e.g. “Will Marketing help in weeks 20–24? (waiting for answer)”

Lessons Learned: e.g. “Plan user interviews well on time”