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Use this checklist of questions from the First Round Review annual planning guide as your team kicks off the annual planning process. (If you’re already in the midst of a planning cycle and don’t have a clear answer on some of these questions, that could be a signal to pause and regroup

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<aside> <img src="/icons/timeline_gray.svg" alt="/icons/timeline_gray.svg" width="40px" /> APPROACH:

• What style of annual planning is right for our company?
• Where are we drawing external inspiration from?
• How are we tailoring it to our business model and stage?
• Is there anything we explicitly don’t want to do, because it’s not a fit or we don’t agree with it? </aside>

<aside> <img src="/icons/telescope_gray.svg" alt="/icons/telescope_gray.svg" width="40px" /> VISION:

• ****How far forward are we looking?
• How are we balancing a big vision with what we can practically do in the next year? </aside>

<aside> <img src="/icons/arrow-down-line_gray.svg" alt="/icons/arrow-down-line_gray.svg" width="40px" /> CONSTRAINTS:

• How (and when in the process) are we allocating headcount?
• How do we rate our team’s current operational maturity and forecasting ability? </aside>

<aside> <img src="/icons/subtask_gray.svg" alt="/icons/subtask_gray.svg" width="40px" /> ORG DESIGN:

• ****Does our strategy show up in our org chart? How does our organizational structure support (or hinder) our strategic goals?
• How should we adjust org design to align with our plan? </aside>

<aside> <img src="/icons/run_gray.svg" alt="/icons/run_gray.svg" width="40px" /> EXECUTION:

• How will we monitor our progress throughout the year to make sure this is a living and breathing document?
• How will we adapt our plan as circumstances change throughout the year? What triggers will prompt us to revisit and potentially revise? </aside>

<aside> <img src="/icons/swap-vertically_gray.svg" alt="/icons/swap-vertically_gray.svg" width="40px" /> PROCESS:

• ****How long are we aiming for our process to take?
• How will we sequence our planning?
• How are we involving input from the entire team?
• How are we handling dependency mapping across teams? </aside>

<aside> <img src="/icons/groups_gray.svg" alt="/icons/groups_gray.svg" width="40px" /> ROLES:

• Who is “holding the pen” for this exercise? Who is making the final decision?
• How much autonomy are we giving our teams in planning? </aside>

<aside> <img src="/icons/bullseye_gray.svg" alt="/icons/bullseye_gray.svg" width="40px" /> GOAL-SETTING:

• Are we aligned on how we’re defining success?
• What is the math that’s required to make our business work? </aside>

<aside> <img src="/icons/robot_gray.svg" alt="/icons/robot_gray.svg" width="40px" /> DISRUPTION:

• How is AI impacting our planning process, product roadmap and business strategy?
• How are we factoring AI into our productivity assumptions? Do we need to create new teams or roles? </aside>

<aside> <img src="/icons/playback-fast-forward_gray.svg" alt="/icons/playback-fast-forward_gray.svg" width="40px" /> LOOKING AHEAD:

• What can we do to improve on our annual planning process next time? Where did we encounter bottlenecks or challenges?
• Pre-mortem: If it’s the end of next year and we’ve failed to reach our targets, why might that be? </aside>