How to Build a 2026 Playbook
A step-by-step guide to generate your 2026 Playbook and dominate the year to come.
Most of us who lead a business, organization, or team have a general sense of what we’d like to accomplish in the coming year.
And if you run EOS (Traction), you likely have an annual planning meeting on the books in which you define the measurables and rocks (goals) for the year to come.
But an additional phenomenal tool I’ve been using for the last three years has made planning for the year to come much easier: The Annual Playbook.
Here’s how it works:
Each year, in October, I create a draft of next year’s Playbook during Think Week.
When I return, I slice and dice this with my leadership teams for the next few weeks.
By the time our annual Traction Meeting rolls around in December, we already have a focused, 2-3 page playbook, allowing us to focus solely on the “how” of the following year instead of the “what.”
And this year, I added a little extra to the playbook creation process: a custom GPT I built to act as a “Socratic business coach.” This turned 3-4 hours of contemplation and writing into an hour or two of “dialog” with ChatGPT. The results were twice as good in half the time. (Curious how to build a custom GPT? Here’s how.)
In this newsletter, I’ll give you my playbook framework, then a download you can use to prompt AI (ChatGPT, Gemini, Claude, etc.) to coach you through creating your 2026 playbook.
The Framework
Each business gets its own annual Playbook. And it’s broken down like this:
1. The Story of the Prior Year - What worked and what didn’t work this year?
2. Theme for Next Year - What’s our general purpose and goal for the coming year?
3. Financial Model - What numbers must we hit in the coming year?
4. Departmental or Functional Focus Areas - What must each team do to make the Playbook come true?
5. Shared Targets & Stretch Reward - What metrics will tell us if we’re on track or off track as the year progresses? How will we reward success?
6. Looking Ahead - If our goals come true, how does this position us for the next 3, 5, and 10 years?
Resources You’ll Want On-Hand Before Starting
Part of generating your Playbook using AI assistance is “feeding” the chat context about your business. This isn’t required (if you don’t do it, the chat will ask you a ton more questions before producing the Playbook), but it will streamline the process.
Here’s what you may want saved as a PDF, and easily accessible, before diving into your playbook generation:
Past Stuff: Your current year P&L, your current year written plan (EOS = V/TO), your current year playbook, if you have one.
Future Stuff: Your forecast for next year. (Here’s a post about how to create that...)
Now that you have any or all of those items ready, let’s dive in.
How to Harness AI In Creating Your Playbook
Ready to generate your Playbook using AI? Here’s how:
Step 1: Sign up for ChatGPT, Gemini, or Claude. Any of these will work. No need for the paid version of these to accomplish this Playbook, using the free models for any of the platforms will work swimmingly.
Step 2: Download The Audacious Playbook Creation Guide here.
Step 3: Open a new chat in your AI, and upload the PDF of The Audacious Playbook Creation Guide.
(Need help with this step? Here’s a How-To Video for you!)
Step 4: Your AI will likely start walking you through the process. If not, copy and paste this prompt into your chat thread next:
“I’m thinking through the year ahead for my business, and I want to build the [YEAR] Playbook for [COMPANY NAME]. This Playbook will summarize our key learnings from last year, translate next year’s financial model into strategy, and outline priorities by department or function.”
Step 5: The AI will ask you for various documents, such as financials for the current year, forecasts for next year, your current Traction V/TO, etc. If you don’t have these, don’t worry. Just tell the AI, “I don’t have these, ask me whatever questions you need answered instead.”
Step 6: After 30-90 minutes, you should have an incredible draft of your Playbook. Share this with your team, and edit as needed until it’s ready to serve as your “north star” for the coming year!
Wrap Up
AI gets a bad wrap. People constantly complain that “no one will be able to think for themselves anymore.” And while cognitive erosion, especially of our kids, can be a byproduct of improper AI use, that’s a one-sided and narrow-minded concern.
In my opinion, the real power of AI is not in generating answers but in asking great questions.
My custom GPTs ask incredible questions that allow me to “see” a different perspective or consider alternate approaches. That’s what I love about it. I strongly encourage you to use it the same way.
Any issues with getting this set up? Email me and I’d be glad to help: scott@scottmonday.com
Thanks for reading this post. I appreciate you. In return, please share this with those you know who may be interested.
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I created 10 Custom GPTs to handle key roles inside my business—CFO, ops, marketing, HR, and more.
The full guide includes templates, my step-by-step setup, and how we rolled it out across the team.
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