// week 03 · day 11 · mon

Sequence Work and Name Trade-offs.

$/roadmap-prioritization · ~25 min
// 01 · what it does

Sequence on the record.

roadmap-prioritization compares candidate initiatives on consistent dimensions — problem clarity, evidence quality, impact, cost, dependencies, reversibility, time sensitivity, and cost of waiting — then recommends a sequence with explicit reasoning for each position. It also produces a "What We're Not Doing" section for every deferred initiative: why not now, what would change the decision, and how to frame the deferral so it doesn't re-open every planning cycle.

Prioritization fails when it's implicit. When a PM can't explain in one sentence why Initiative A beats Initiative B, the rationale gets lost — and the next planning cycle starts from scratch. roadmap-prioritization forces the comparison to happen on the record, with the reasoning preserved and the trade-offs named. The deferred-initiative section is as important as the sequence: it converts "we decided not to do X" into "we decided not to do X yet, because Y, and Z would change that."

Day 11 opens the strategy week because it sequences the investments built across Weeks 1 and 2. The business cases, feedback syntheses, and data analyses from the past ten days are the inputs. This skill decides what gets executed in what order — and names what's being left behind and why.

// 02 · sample prompts

Two ways in.

prompt.basic.txt 
/roadmap-prioritization

Prioritize these four initiatives for my team next quarter. We have capacity for about two of them:

1. Add difficulty-level filtering to search
2. Build a guide response-time SLA (guides must respond within 24 hours or the booking is auto-declined)
3. Add post-experience share functionality (adventurers can share completed trips)
4. Redesign the onboarding checklist for new guides

We care most about booking conversion and guide retention. Limited data on all four.
prompt.advanced.txt 
/roadmap-prioritization

Compare Terrain's four known product problems and recommend a sequence for the quarter after Android GA ships (Android GA target: 6 weeks from now).

Candidate initiatives:
1. Guide activation — listing setup guidance and pricing transparency (from Day 1 PRD). Evidence: Day 7 feedback synthesis confirmed setup friction and pricing uncertainty as recurring themes. Day 6 discovery plan mapped assumptions; structured research not yet complete.
2. Adventurer repeat loop — personalized re-engagement (from Day 10 business case). Evidence: strong; Day 7 and Day 8 analysis support the claim. Sizing: ~$609k GMV uplift for a 7-point improvement.
3. Cancellation rate reduction — policy and tooling (problem: 14% cancellation rate, industry benchmark 7–9%). Evidence: Day 7 synthesis showed weather-related cancellation anxiety as a major theme. No discovery plan yet.
4. Instant Book flexible mode — configurable advance-notice window for guides (from the pending Instant Book rollout decision context). Evidence: 22% opt-in among eligible guides despite about 32% detail-to-booking conversion lift. Guide concern is calendar risk.

Constraints:
- Android GA is non-negotiable and consumes the single Android engineer and significant backend bandwidth for the next 6 weeks
- Instant Book rollout is already in-flight — any Instant Book work must coordinate with Jordan Lee's squad
- Team capacity post-Android GA: approximately 18–22 story points per sprint
- Dana Park's H1 OKRs: GMV growth, guide retention (71% → 80% 12-month retention), adventurer repeat rate (38% → 45%)

Include the full stress test.
// 03 · reflection

Three questions.

  1. 01Did the skill sequence the initiatives the way you would have — and if not, where does your reasoning differ from its reasoning?
  2. 02What did the "What We're Not Doing" framing reveal about the opportunity cost you're accepting with this sequence?
  3. 03What single piece of new information would flip the top priority to second place?
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