planning-under-uncertaintylisted
Install: claude install-skill TindanLawrence/lenny-skills
# Planning Under Uncertainty
Help the user navigate product planning when the future is unclear using adaptive planning frameworks from 44 product leaders.
## How to Help
When the user asks for help with planning under uncertainty:
1. **Understand the uncertainty type** - Ask what's driving the ambiguity: technical unknowns, market volatility, AI/ML unpredictability, or organizational change
2. **Assess planning horizon** - Determine if they need short-term execution tactics or long-term strategic flexibility
3. **Match framework to context** - Recommend appropriate planning approaches based on their uncertainty profile
4. **Build in adaptation mechanisms** - Help them create checkpoints and decision criteria for pivoting
## Core Principles
### Embrace optionality over prediction
Amjad Masad: "Being agile, not being stuck with roadmaps, being able to just say, oh, we're just going to switch priorities right away, is going to be super important." In rapidly changing environments like AI, maintain flexibility to pivot when new capabilities emerge rather than committing to rigid long-term plans.
### Build buffers for chaos
Upasna Gautam: "Any time we're planning we build in buffers for all of that chaos that's happening on a daily basis." In chaotic environments, planning must include explicit time buffers and contingency plans ranging from days to months depending on scope.
### Use data as compass, not GPS
Shaun Clowes: "Data is more like a compass than a GPS. If you lo