EP 233 Fail to Plan, Plan to Fail? Your AI Annual Planning Skill!

EP 233 Fail to Plan, Plan to Fail? Your AI Annual Planning Skill!

June 16, 2026 · 10 min · Season 2 · Episode 233

About this episode

In this episode, Brooke Elder discusses how to effectively plan for annual goals using AI tools to break down strategies into actionable steps.

Sound familiar? You set big goals back in January, and now it's the middle of the year and you're nowhere near where you wanted to be. Trust me, you are not alone, and it's almost never because you didn't work hard enough. It's because the plan never got broken down into something you could actually do. "If you fail to plan, you plan to fail" is a cliché for a reason, so in this episode we fix the plan itself. I walk you through a free Claude skill for annual planning that you can grab inside our free community, the AI Ops Yacht Club. It interviews you about last year (your revenue, your wins, your misses), pulls out what to start, stop, and keep, then builds your theme for the year, your goals, your metrics and targets, and the resources you'll actually need to hit them. From there it cascades everything down into quarters and even hands you a one-page plan you can share so your whole team is rowing in the same direction. Every business needs a visionary AND an integrator, and this is how Claude can play that strategic-partner role for you. By the end you'll know how to upload and run the skill, how to feed it your existing business knowledge through a Claude project, and…

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