# Seasonal Planning

> 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

- Skill: `coowoolf/seasonal-planning` (Agent Skill)
- Install (CLI): `npx skillmds@latest add coowoolf/seasonal-planning`
- Raw SKILL.md: https://api.skillmd.com/api/skills/coowoolf/seasonal-planning/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Coding & Dev Tools
- Author: Coowoolf (https://skillmd.com/u/coowoolf)
- Updated: 2026-09-10
- Page: https://skillmd.com/skills/coowoolf/seasonal-planning

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# 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

| Principle | Description |
|-----------|-------------|
| **Season-based** | Secular changes define seasons, not calendar |
| **Loose OKRs** | Direction, not destination |
| **Short sprints** | 4-6 weeks, concrete outcomes |
| **Built-in slack** | Reserve 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

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