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seasonal-planning

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Use in rapidly evolving industries like AI where 6-month plans become obsolete, when needing to balance direction with agility, or when traditional annual roadmaps fail

2 stars
1.2k downloads
Updated 1/19/2026

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SKILL.md

The Seasonal Planning Protocol

Overview

A planning framework for the high-velocity AI era where traditional annual or rigid roadmaps fail. It replaces fixed timelines with "Seasons" defined by secular industry changes.

Core principle: Build for the slope, not the snapshot.

The Framework

┌─────────────────────────────────────────────────────────────────┐
│  1. DEFINE THE SEASON                                           │
│     Based on secular trend (e.g., "Season of Agents")           │
│     Not calendar-based                                          │
├─────────────────────────────────────────────────────────────────┤
│  2. SET LOOSE QUARTERLY OKRS                                    │
│     Directionalize, don't lock down                             │
│     Allow for capability changes                                │
├─────────────────────────────────────────────────────────────────┤
│  3. EXECUTE 4-6 WEEK SQUAD SPRINTS                              │
│     Tight execution loops                                       │
│     Concrete deliverables                                       │
├─────────────────────────────────────────────────────────────────┤
│  4. LEAVE SLACK FOR DISRUPTION                                  │
│     Don't fill capacity to 100%                                 │
│     Room for new model capabilities                             │
└─────────────────────────────────────────────────────────────────┘

Key Principles

PrincipleDescription
Season-basedSecular changes define seasons, not calendar
Loose OKRsDirection, not destination
Short sprints4-6 weeks, concrete outcomes
Built-in slackReserve capacity for the unexpected

Common Mistakes

  • Adhering to rigid annual plans
  • Filling capacity to 100% without innovation buffer
  • Treating all quarters the same despite industry shifts

Source: Asha Sharma (Microsoft AI Platform VP) via Lenny's Podcast

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AI Quality Score

65/100Analyzed 2/25/2026

A solid strategic planning framework for fast-moving industries with clear structure and useful 'when to use' guidance. The ASCII diagram and principles table are effective. However, it lacks concrete implementation steps, examples, and templates needed for high actionability. The 'ci-cd' tag is mismatched - should be 'strategy' or 'planning'. Overall a good conceptual framework that would benefit from more practical guidance."

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Metadata

Licenseunknown
Version-
Updated1/19/2026
PublisherCoowoolf

Tags

ci-cd