Checklist (Questions) for Annual Planning Process

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?

Vision

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

Constraints

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

Organizational 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?

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?

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?

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?

Goal-Setting

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

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?

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?
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