---

name: strategy-to-roadmap
description: "Translate a strategic vision into a 12-month operational roadmap with OKRs, resource allocation, and the organizational friction points that will kill it."

/strategy-to-roadmap

Strategy decks gather dust because they stop at "what" without specifying "how, when, with what resources, and what we stop doing to get there." The gap between a clear strategic vision and a team that's executing against it is almost always a missing translation layer — the set of specific bets, sequenced by dependency, with resources attached and assumptions surfaced. This skill builds that layer.

Strategic Thesis

• What is the core customer insight this strategy is betting on? (Not the vision statement — the observation about customer behavior or market dynamics that makes this strategy right)
• What is the competitive thesis? (Why is this the right move now, given what competitors are doing?)
• What is the financial thesis? (Which line on the P&L does this strategy most directly improve, and by how much over what horizon?)
• What would make this strategy wrong? (The assumptions that, if false, require a pivot)

The 5-7 Most Important Bets

For each bet:

• What is the bet, in one sentence
• What capability does it require that you don't currently have?
• What does it depend on (must be completed before this can start)?
• What is the success metric — the OKR that tells you the bet paid off?
• What is the cost (headcount, opex, capex)?

Map the dependencies. Which bets are foundational (everything depends on them)? Which are parallel? Which are sequenced?

Assumption Register — for each major bet, what must be true:

For each assumption: how confident are you (high/medium/low), how long before you'll know if it's wrong, and what's the cost of being wrong at that point?

Sequencing Logic

• Quick wins (months 1-3): which bets produce visible results fast and build organizational confidence?
• Core investment (months 4-9): the heavy lifting — what are the dependencies that must complete first?
• Scaling phase (months 10-12): what becomes possible only after the core investment is in place?
• What is explicitly NOT on the roadmap? (The things you're deprioritizing deserve as much clarity as the things you're doing)

Resource Allocation

• Total budget required vs available — the gap, if any, and what it means for sequencing
• Headcount: which bets require new hires vs redeployment of existing team?
• Which current activities must stop or shrink to free resources for this strategy?
• The resource assumption that, if wrong, collapses the timeline most severely

Organizational Friction

• Which teams will resist this strategy? What is the specific reason (changes their incentives, reduces their headcount, shifts their priorities)?
• Which leaders need to be aligned before this lands — and where are the alignment gaps today?
• What's the communication plan for the teams who won't like this?
• What behavior from leadership will signal to the org that this strategy is real, not performative?

OKRs — one per major bet:

Objective (qualitative, directional), 2-3 Key Results (measurable, with a number and a date), and the leading indicator that tells you you're on track before the KR is hit.

Rules

1. Every bet must have a named owner, a resource allocation, and a success metric. Unowned bets don't get done.
2. The "not doing" list is as important as the roadmap. Without it, everything is still priority 1.
3. OKRs without leading indicators are just targets. You need to know in month 3 whether you'll hit the month 9 KR.
4. Organizational friction is not a soft concern — it is the most common reason strategies fail. Name it explicitly.
5. Assumptions must be ranked by how quickly they'll be tested. Early tests save late pivots.
6. Quick wins must be real wins — not theater designed to look like progress. If they don't build toward the core investment, cut them.

The output of this skill is an operational roadmap document: thesis, bets with dependencies mapped, OKRs, resource allocation table, and a friction log — ready for the leadership team to pressure-test.