How AI Can Cut Your Planning Cycle From Two Weeks to Two Days

Quarterly and annual planning is a painful process that many of you have likely experienced. Every’s head of growth Austin Tedesco describes how the intentional use of AI can cut the process from weeks to hours, leaving you and your team with more energy and focus. If you’re already seeing your annual planning spilling over into January, this one’s for you.—Kate Lee

Was this newsletter forwarded to you? Sign up to get it in your inbox.

The quarter is closing. You’ve spent hours compiling data about your team’s performance. Your calendar is filling up with planning meetings, but your team is messaging you for help on the final push to meet this year’s targets. You feel pulled in a million directions.

I’ve seen organizations struggle with this tension throughout my career in media and startups. Focus too much on the day-to-day of the business at yearly and quarterly junctures, and you lose the chance to extract lessons from previous work. Focus too much on strategy, and growth stalls.

This doesn’t mean that you need to bypass formal cycle planning, as many startups do. Taking time to align on goals and build a focused roadmap is necessary to drive growth. The problem is how long the process takes—finding yourself in mid-January without your annual goals finalized.

Innovative companies are now solving this conundrum with AI, and it’s something we are also rolling out at Every. Bringing AI into the process saves time, leads to more refined goals, and preserves energy for the work that matters.

The tech stack

It’s helpful to start with a standard framework for the planning itself. In the past, I’ve used the W Framework. Outlined by Lenny Rachitsky and Nels Gilbreth, previously at Airbnb and Eventbrite, respectively, this approach to quarterly and yearly planning involves four steps:

1. Context: Leadership shares a high-level strategy with teams.
2. Plans: Teams respond with proposed plans.
3. Integration: Leadership integrates into a single plan and shares it with teams.
4. Buy-in: Teams make final tweaks, confirm buy-in, and get rolling.

When done well, these documents are immensely valuable. They outline what each department will and won’t do, who owns those projects, and a standard for success in a concise and data-driven way. Call it what you will—OKR, KPI, or DRI—but the most important thing is driving focus and alignment on the few things that matter most.

I’ve worked at companies where each of these steps takes multiple days—sometimes entire weeks. Here are three tools I’ve used to shrink that down to just a couple of hours.

Shared knowledge hubs

A central LLM-supported source for all relevant information: what happened last quarter or year, what you’re planning in the next period, concrete examples, data, templates for briefs. A COO or chief of staff can compile this in projects via Claude, ChatGPT, or Notion.

You can include:

1. Previous plans and reflections on previous work
2. Templates and examples for written documents and presentations
3. Guidance on tone and audience (such as a style guide)
4. Company strategy docs and OKRs
5. Relevant data (actual performance, targets, year-over-year comparisons)
6. Meeting notes from planning conversations

When you have this set up across your entire team, you never have to start from a blank page. You don’t have to go hunting for examples for a client presentation or run data analysis from scratch. You ask, and it answers. At some forward-thinking companies, I’ve seen these knowledge hubs automatically pull in new meeting notes, Slack conversations, and up-to-the-minute data.

If you are using a knowledge hub like Claude Projects that can include instructions for how the model should behave, telling the model to ask clarifying questions before doing any work. It’ll probe for gaps you didn’t know you had.

AI notetaker

Granola, Notion, Google, Zoom—there are a lot of good options for recording meetings before and during the planning process. These notes are helpful for the initial draft of the planning documents, but they’re most powerful when you are making revisions to the documents and integrating goals with other teams.