Seasons Planning

Plan around secular industry shifts, not fixed time periods

Asha Sharma
How 80,000 companies build with AI

Seasons Planning

"We think about it as what season are we in? A season... can be denoted by a set of secular changes that are happening in the industry or that are happening from customers. Season one might've been the prototyping of AI, then it was all around models and reasoning models, and now it's the advent of agents." - Asha Sharma

What It Is

A planning framework that replaces fixed time-based planning (quarterly, semester, annual) with planning around industry "seasons"—distinct periods defined by major technological or market shifts. The duration is variable: a season can last three months, six months, or a year, depending on how rapidly the landscape is evolving.

This emerged from the challenge of planning roadmaps in fast-moving environments where GPT-5 can drop and invalidate your six-month plan. Traditional planning cadences assume relative stability; Seasons Planning acknowledges that the pace of change itself is variable.

How It Works

Three Planning Layers:

1. Season Definition (Variable Duration)

  • Identify the secular changes in your industry
  • Name the current season based on what's shifting
  • Define what "winning" looks like in this season
  • Establish a north star metric for the season

Examples of seasons:

  • "Season of prototyping" (early experimentation)
  • "Season of reasoning models" (capability advancement)
  • "Season of agents" (application and integration)

2. Quarterly OKRs (Loose)

  • Set objectives that put you on a path toward season success
  • Keep them loose enough to adapt
  • Focus on problem areas, not specific solutions

3. Squad Goals (4-6 Weeks)

  • Teams work in short sprints toward specific problems
  • Goals ladder up to quarterly OKRs
  • Fast enough to pivot when the landscape shifts

Key Principle: Leave Slack Reserve capacity not just for the unplanned, but for "the slope"—continuous investment in what might disrupt your own platform. You need to be thinking about the next season while executing in the current one.

How to Apply It

  1. Name your current season - What secular shifts define this period? What customer problems have emerged? What does winning look like?

  2. Align on ethos, not details - Get everyone understanding the season's characteristics. The shared context matters more than prescriptive plans.

  3. Set loose quarterly objectives - Ask: "If this is the season we're in, what must we accomplish in the next quarter to be on track?"

  4. Run squad sprints - 4-6 week focused efforts on specific problems that ladder to quarterly goals.

  5. Build in slope investment - Protect time for exploring what comes next, not just executing on what's now.

  6. Accept frequent recalibration - "We go through lots of changes all the time and I think we have to just have an openness that that is the business that we're in."

When to Use It

  • When your industry is experiencing rapid technological change
  • When traditional planning cycles feel too rigid
  • When new developments regularly invalidate roadmaps
  • When you need to align large organizations around a moving target
  • Particularly relevant for AI product teams today

Source

  • Guest: Asha Sharma
  • Episode: "How 80,000 companies build with AI: Products as organisms and the death of org charts"
  • Key Discussion: (30:49-33:24) - Explains the seasons approach to planning
  • YouTube: Watch on YouTube

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