# Strategy-to-Roadmap Cascade System — AI Context Brief (v5) An AI Context Brief for standing up a recurring strategy-to-roadmap operating system — an annual strategic frame, quarterly WSJF rescoring, a weekly drift check, and a recalibration trigger rule — delivered as a single step-by-step implementation guide. Applicable to any team or function running a competing-priorities portfolio, not just technology teams. v5 adds the corrected reference diagram below to the package — same prompt as v4, now paired with the System Summary visual as it should actually render: no stray unlabeled elements, and diagram text sized to match the surrounding body copy instead of reading as a shrunken afterthought. ``` You are helping me design and stand up a recurring Strategy-to-Roadmap Cascade System for my organization — not a one-time roadmap document, but an operating rhythm I'll actually run every quarter (and check on weekly). Don't hand back a generic OKR philosophy essay or a set of disconnected worksheets — deliver a single step-by-step implementation guide that tells me exactly how to run this, not just what it is. MY SITUATION — YOUR STRATEGIC INPUTS Before asking me anything below, check whether I've attached reference materials — a current project/initiative list, documentation on existing systems, prior strategy decks, cascaded goals from the CEO/board/executive team, or a general org profile. If I have, extract as much of the information below as you can directly from those documents rather than making me retype it, and tell me which fields came from my documents versus which you're asking me directly, so I can correct anything misread. If a document only covers part of what's needed, ask only for what's genuinely missing. If something in a document conflicts with what I tell you directly, flag the conflict and ask which is current — don't silently pick one. Don't assume an uploaded document is exhaustive; if it only covers some initiatives or a partial history, ask whether there's more before treating the picture as complete. Organization Profile - Organization size: [employee count] / [team, division, or scope this system covers] — often in an org profile document, if attached. Current State - What exists today: [nothing formal / an annual roadmap that goes stale / a rough backlog with no scoring] — often answered by an existing project or initiative list or systems documentation, if attached. Strategic Choices (do not invent these) - Do you already have defined answers for Winning Aspiration, Where to Play, How to Win, Capabilities Needed, and Management Systems? Often already answered in a prior strategy deck or a cascaded goals document from the CEO, board, or executive team — check uploads first. If yes (from an upload or direct answer), give them to me as-is. If no, say so explicitly — don't let me guess at placeholder language for you. Instead, walk me through a structured working session to draft first-pass answers I can bring to my leadership team for confirmation. Tier, Tools & Platform - Tier or investment approach: [Lean — no new software spend / Mid-market — open to a modest new tool / Enterprise — have or can get budget for a dedicated platform] - Systems already in place: [list what you actually have licensed or use today — check systems documentation, if attached] - Platform for ongoing tracking: [name one if you have it — most support Excel or CSV import. If you don't name one, I'll build a working Excel workbook with live formulas instead.] Reporting, Scale & Meeting Cadence - Who this reports to or gets reviewed by: [CEO, board, steering committee, my own leadership team] - Roughly how many competing initiatives are in play at once: [a number or range — check an attached project/initiative list first] - Existing recurring meeting(s) this could attach to: [name one, or say none exists yet] CONSTRAINTS - Never recommend adopting a new platform. My goal is documents and steps that slot into whatever I already run, not a tool decision. - Never invent my Strategic Choices. If I haven't given them to you or they aren't in what I uploaded, run the working-session exercise instead of filling the boxes in yourself. - Match the review cadence to real bandwidth. If I can't credibly commit to a weekly check-in, tell me what I lose by going biweekly or monthly instead, and let me choose. - If I haven't given you initiative-level cost/value data — directly or in an upload — don't invent scores. Ask me for the real initiatives and their rough business value, time-criticality, effort, and whether any carry a hard compliance, contractual, or vendor deadline, or mark those fields as placeholders I need to fill in. DESIGN I NEED — DELIVERED AS ONE STEP-BY-STEP HTML IMPLEMENTATION GUIDE 1. Your Strategic Inputs — restate what I gave you (directly or from uploads) organized by category, at the top of the guide, noting the source of each, so I can confirm accuracy before reading the rest. 2. Annual Strategic Frame — built from my actual Strategic Choices (direct answer or upload), or from the working-session exercise if neither existed. Include one short paragraph on when and how to operationalize this: who reviews it, how often, and what happens if a box is contested. 3. Quarterly Rescoring Worksheet — WSJF (Cost of Delay ÷ Job Size, where Cost of Delay = Business Value + Time Criticality + Risk Reduction/Opportunity Enablement), plus a Must-Do flag column for hard compliance/contractual/ vendor deadlines. Include step-by-step directions: who submits initiatives and by when, who scores them, and exactly how to load the result into the platform I named (or the live-formula Excel version if I didn't name one). 4. Weekly Drift Check — the check questions, plus directions on how to use them: attach to an existing recurring meeting or suggest creating one. Include a week-over-week tracking template — a running grid, not a single-use checklist. 5. Recalibration Trigger Rule (not "re-cascade") — restate the trigger conditions as a standing question on the same meeting agenda as the drift check, then give an explicit recalibration procedure as a decision path: which conditions only require updating the Quarterly Rescoring Worksheet, versus which require rerunning this brief and regenerating the Annual Strategic Frame — and be explicit about who does which step. 6. System Summary — a recap of every template and tool this guide produced, plus a simple diagram showing how they connect across the annual/quarterly/ weekly cycle, including where each recalibration path feeds back in. Keep every element on the diagram tied to something labeled — no decorative marks (dimension ticks, rules, brackets) that don't carry a number or a name — and size the diagram's text close to the surrounding body copy so it reads as content, not as a shrunken thumbnail. WHAT GOOD OUTPUT LOOKS LIKE One HTML guide I could hand to my team and follow start to finish without another conversation. The Strategic Frame reflects my real strategic choices — from what I typed or what I uploaded — or an honest working session, never invented language. The weekly section includes something I can fill in week after week. The recalibration section tells me exactly what to do, in what order. The closing section is a recap and a diagram, not a product recommendation. ``` *What good output looks like: an HTML guide styled with your own brand system, containing every template plus operational instructions for running it — not a text explanation of what the system is.* --- ## Reference Diagram — System Summary Visual (Corrected) The System Summary diagram from the populated example, as it should actually render: the annual → quarterly → weekly cascade in black with right-angle connectors, the two recalibration paths in dashed teal, and no unlabeled decoration. Text sizes are set so the primary labels (Strategic Frame, WSJF Rescoring Worksheet, Drift Check + Recalibration Question) render close to a 16px body-copy size rather than reading as a smaller, separate visual register. Drop this in directly wherever the guide's `
` block goes. ```html
ANNUAL Strategic Frame REVIEWED YEARLY QUARTERLY WSJF Rescoring Worksheet RESCORED EVERY QUARTER WEEKLY Drift Check + Recalibration Question STANDING 15-MIN SYNC MINOR RECALIBRATION MAJOR — RERUN THE BRIEF BLACK = CASCADE · TEAL DASHED = RECALIBRATION FEEDBACK
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