Planning in Seasons
Replace rigid roadmaps with secular 'seasons', loose quarterly OKRs, and deliberate slack
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 4
- Confidence
- 92%
A planning cadence for environments changing too fast for six-month roadmaps. Ground everyone in the current 'season' (defined by secular industry/customer shifts), set loose quarterly OKRs beneath it, run squads on 4-6 week goals, and deliberately leave slack in the system for both the unplanned and the 'slope' of future disruption.
Origin
Asha Sharma's adaptation of Microsoft's traditional six-month 'semester' planning, evolved for the pace of AI where a model like GPT-5 can drop mid-cycle and invalidate a roadmap.
Core principles
- 01A season is defined by secular changes in the industry or from customers, not by a fixed calendar
- 02Ground everyone on the ethos: what's changing, what customer problems to solve, what winning looks like, and the northstar metric
- 03Seasons are uncomfortable and variable — they can last three months, six months, or a year
- 04Leave slack not just for the unplanned but for the slope — how you'll disrupt your own platform
- 05Openness to constant change is the business you're in, not a failure of planning
How to run it
- 1
Name the current season
Define the season by the set of secular changes happening in the industry or from customers (e.g. prototyping of AI → models and reasoning → the rise of agents). Align everyone on the ethos and northstar metric.
Pro tip Give the season a shared name so the whole org centers its strategy on the same secular shift.
Watch out Don't force a season onto a fixed six-month calendar — its length is dictated by the change, and could be 3, 6, or 12 months.
- 2
Set loose quarterly OKRs
Ask what you need to do next quarter to put yourself on a path toward the season's goal, and set OKRs loosely enough to survive mid-cycle surprises.
- 3
Run squads on 4-6 week goals
Have teams operate in squads with four-to-six-week goals for specific problem areas that ladder up to the quarterly OKRs.
- 4
Leave deliberate slack in the system
Reserve capacity not only for unplanned events but for the 'slope' — continuously investing in how you'll disrupt your own platform.
Pro tip Treat slack as a permanent line item; it's what lets you absorb a GPT-5-style shock without derailing the whole plan.
In the wild
Sharma's teams moved through seasons — prototyping of AI and early GPT work, then models and reasoning models, and now the rise of agents — re-grounding the org on each secular shift rather than a fixed roadmap.
→ Teams stay aligned on the current secular change while absorbing frequent disruptions, currently operating in the 'rise of agents' season with 15,000 customers deploying agents.
Common mistakes
Over-baking a six-month roadmap
Committing to a detailed half-year plan when the frontier can shift underneath you mid-cycle, leaving the plan stale and rigid.
No slack for the slope
Planning every unit of capacity against known work leaves nothing to invest in self-disruption or to absorb the unplanned.
Is it for you?
Best for
Product and platform leaders in fast-moving categories (especially AI) who need alignment without a brittle long-range roadmap
Not ideal for
Stable, slow-changing domains where predictable multi-quarter roadmaps still hold and seasons would add needless churn
From the transcript
“we kind of think about it as you know what season are we in? And so a season which is very uncomfortable can be denoted…”
“we have kind of loose quarterly OKRs. So like okay if we believe that what do we need to do next quarter”
“teams are operating in squads and they're kind of setting out you know four to six week um goals”
“we try to leave slack in the system not just for the unplanned but for the the slope”
From the episode
How 80,000 companies build with AI: products as organisms, the death of org charts, and why agents will outnumber employees by 2026
Asha Sharma (CVP of AI Platform at Microsoft)