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?
Source: Annual Planning Sucks — A CPO, CRO, CFO, and COO Share Advice on How to Make it Better
Subjects: Management Questions, Strategy Questions
Subjects: Management Questions, Strategy Questions
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