Scaleflow plans at three horizons that feed each other. Initiative Planning produces The ApproachThe ApproachThe multi-week narrative roadmap — titled weekly outcomes ("The one where…"), each with a demo, planned backwards from success.. Week Planning produces the weekly plan. The Daily Check-inDaily Check-inA 15-minute daily ritual where the team surfaces reality and unknowns rather than reporting status. commits the daily 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). Each horizon is the same idea at a different zoom level, and each one refines the one above it.

Initiative Planning

Initiative Planning is a 120–240 minute team workshop, run once per initiative and refined as the work demands. It turns the Initiative DocumentInitiative DocumentThe PR/FAQ-shaped document where an initiative's context lives — customer, solution, plan, business case, and success metrics. into a multi-week narrative roadmap — The Approach.

Work through it in order:

  1. Brief the team on the problem, the customer, the solution, and the success metrics from the Initiative Document.
  2. Commit to timeline OR outcome — not both. Fixing both is how teams quietly start lying to themselves. Pick the one that matters and let the other flex.
  3. Validate the metrics. Every success metric must be specific, measurable, relevant, and time-bound. No ambiguity survives this step.
  4. Write down every unknownUncertaintyWhat the team does not yet know — sized and tracked deliberately rather than hidden inside estimates. and size it. Apply the sizing heuristic — small initiatives name one key Uncertainty, medium ones name the top three, large ones name the top five. Phrase each as a question (If/Then or Will/When).
  5. Specify the total weeks the initiative needs.
  6. Add the events to consider — holidays, conferences, freezes, dependency deadlines.
  7. Work backwards. The last week’s outcome is success from the Initiative Document. Title it, then move back week by week. Give each week a “The one where…” title that captures its main outcome.
  8. Give each week an outcome and a demo — what the team 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 that week.
  9. Assign every Uncertainty to a week. Each one becomes a TFO or a planned demo objective. The Approach is partly an uncertainty schedule.
  10. Optionally add tracks — workstream titles like Design, Frontend, Backend, Research — with each person listing outcomes per track per week.

The Approach is a sliding window, not a fixed Gantt chart: six to twelve weeks of real detail, then a few months at lower resolution, then quarters, then halves. You adjust it weekly. It starts early and unrefined — often just the Initiative AuthorInitiative AuthorThe person accountable for an initiative's context — they write and keep the Initiative Document honest. sketching weeks alone — and grows up as the team forms around it.

Example · #REALITY

A team rebuilding onboarding fixes the outcome — “new users reach first value in under ten minutes” — and lets the timeline flex. Working backwards, the final week becomes “The one where the new flow is live for all signups.” The week before is “The one where we proved the new flow beats the old one in an A/B test,” which carries the desirability Uncertainty. Two weeks earlier sits “The one where we figured out why users stall on the integration step” — a pure figuring-out week. Read top to bottom, the titles are the plan.

Week Planning

Week Planning translates this week’s slot of The Approach into concrete deliverables and demo commitments, blending multiple initiatives and non-initiative work into one coherent week. Look ahead at events and holidays, collect the work (on track, leftover, to demo, uncertainties to reduce), then distribute and assign it. The hard rule is the 75% capacity rule: load only about three-quarters of the team’s capacity and leave a quarter for the unknown, because the unknown always arrives. If a week’s title or goals shift materially, update The Approach to match.

The Basic Approach Plan

When full Initiative Planning is overkill, there’s a leaner alternative:

  • Each week gets a “The one where…” title.
  • Each week lists the events to consider.
  • Each week lists its Weekly Goals — the outcomes.
  • A bi-weekly stakeholder update covers outcome reflection, lessons learned, plan changes, and next week’s title and goals.
  • Optionally, keep master lists of uncertainties, impediments, and lessons learned.

Approach → Tracks → Weekly Goals

The Approach sets the direction. Tracks break it into parallel lines of work. Weekly Goals are what the team commits to this week. Each level is a refinement of the one above, so a single daily TFO can be traced all the way back to the initiative’s north star.