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seasonal-planning skill

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This skill helps you implement seasonal planning in fast-moving industries, balancing agility with direction through seasons, loose OKRs, and short sprints.

npx playbooks add skill coowoolf/insighthunt-skills --skill seasonal-planning

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SKILL.md

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---
name: seasonal-planning
description: 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
---

# 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

---

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

Overview

This skill teaches a Seasonal Planning Protocol for fast-moving industries like AI where annual roadmaps quickly go stale. It replaces calendar-driven plans with "seasons" based on secular industry shifts and emphasizes directional OKRs, short execution cycles, and built-in slack. The approach helps teams stay aligned to long-term slope while remaining highly responsive to new capabilities and disruptions.

How this skill works

You define a season by a dominant secular trend (for example, "Season of Agents") rather than by quarters. Set loose, directional quarterly OKRs that can adapt as capabilities change. Execute work in 4–6 week squad sprints focused on concrete deliverables, and keep intentional capacity unallocated to absorb disruptive opportunities or new model features.

When to use it

Working in high-velocity industries where six-month plans become obsolete
When you need to balance strategic direction with rapid tactical shifts
If traditional annual roadmaps cause missed opportunities from new capabilities
Launching products that depend on external model or platform changes
When teams must remain outcome-focused but flexible in approach

Best practices

Define seasons from observable secular trends, not calendar dates
Write OKRs as directional guardrails, not immutable deliverables
Run 4–6 week squad sprints with clear, testable outcomes
Reserve deliberate slack—avoid filling capacity to 100%
Use a rolling review every season to reassess strategy and priorities

Example use cases

A product team adjusting priorities after a major model capability release
Companies shifting investment from infrastructure to agent workflows during an "agents" season
Startups avoiding sunk planning costs by using loose seasonal OKRs
Engineering squads delivering incremental value in short sprints while waiting for external APIs
Leadership reallocating budget mid-season to capitalize on a sudden market shift

FAQ

How long is a season?

A season is defined by a secular industry shift and has no fixed calendar length; it lasts until the underlying trend meaningfully changes.

How do seasonal OKRs differ from regular OKRs?

Seasonal OKRs are directional and intentionally loose, allowing teams to pivot as capabilities or market signals evolve rather than locking to fixed deliverables.