Raw Content
How AI Can Cut Your Planning Cycle From Two Weeks to Two Days
Core Argument
Austin Tedesco, Every’s head of growth, demonstrates how intentional AI implementation can compress quarterly and annual planning from weeks to hours while improving strategy quality and team energy levels.
The Problem
Traditional planning cycles consume excessive time through multiple rounds of meetings, document revisions, and alignment discussions. Teams often find themselves still finalizing goals in January, creating tension between day-to-day execution and strategic work.
Three Essential Tools
Shared Knowledge Hubs: Centralized AI-supported repositories containing previous plans, templates, style guides, company strategy, performance data, and meeting notes. Users query this system rather than starting from scratch.
AI Notetaker: Recording tools (Granola, Notion, Zoom) that capture planning conversations for efficient drafting and revision.
Speech-to-Text Tools: Monologue or similar dictation platforms enabling rapid brain-dumping of ideas without worrying about tone or formatting.
Seven-Step Implementation Process
- Align on strategy with leadership (90 minutes)
- Brain dump via speech-to-text into document template (5-10 minutes)
- Have the AI interview you with clarifying questions before drafting
- Voice-over revisions to refine initial draft to A-quality (under 1 hour)
- Integrate across teams using AI to spot resource conflicts and dependencies
- Implement leadership feedback with AI assistance
- Generate deliverables (executive summaries, presentations) in multiple formats
Key Benefits
- Earlier execution: Gaining 2-4 weeks of productive work time
- Sharper thinking: AI probing reveals strategic gaps
- Preserved energy: Reduces planning fatigue and maintains momentum
- AI adoption: Demonstrates compelling efficiency gains that build organizational buy-in
Critical Success Factor
Specify in AI project instructions: “Always ask probing, clarifying questions before large tasks.” This prevents the model from making unfounded assumptions about strategy based on incomplete context.