Annual Planning

Annual planning is useful for coordinating across a multi-threaded company and forcing leaders to take stock of where they are going1. When conducting a technical organization’s annual planning, use the time to understand where your company and department are at, where your company wants to go, and how your department gets your company there. Lena Reinhard provides a template for this planning2. After the plan is developed, take the department along by first sharing in a meeting with all managers. Follow by sharing it with your department and broader stakeholders.

Annual planning seeks to do a lot (leadership buy in, roadmapping, headcount planning, etc.), and by seeking to a do lot, it fails to do one thing well. Try to break apart and solve for each one individually1.


  1. Try to get planning done before the year starts. Knowing high priority objectives for early in the year can help this2.
  2. Include your direct reports early in the process2
  3. Leave room for adjustments based on external and internal parties2
  4. Do not introduce new things, the rush of the yearly plan results in shallow planning for new things. New things require budget, buy-in, coordination that the yearly process does not lend itself to1.
    1. Minimize dependencies by focusing on building on what exists (avoid introducing new things)1 .
  5. De-couple headcount planning from this process to avoid the incentives of headcount from corrupting the planning process1.
  6. Bottom up planning process do not work because teams do not have the perspective of other teams, additionally they are unlikely to understand what other teams will have to do to accomplish a task. Finally, this sets a floor for their expectations1.

Develop Frameworks and constraints for prioritization

Frameworks themselves can introduce constraints, some prioritization frameworks1:

Make sure that you account for the keeping the lights on work and other (non-obvious) constraints1.


In rolling out the plan, hit these communication points2:

What is the corporate strategy? What is our engineering vision (what does the team look like by x date)? What is our engineering strategy (the why behind the what)? Investments in delivery, tech, organization, teams, and people


  • Anticipate the “what does this mean for me?” question2
  • Continue to discuss and share the strategy throughout the year2


Elliot-McCrea, K. How to plan? Kellan elliott-mccrea at (2022).
Reinhard, L. How to do annual planning and strategy for an engineering organization. Lena reinhard Blog at (2023).