How to plan?

Kellan Elliott-McCrea provides strategic planning guidance for engineering leaders focused on practical execution principles: do fewer things (reduce complexity and high-stakes coordination), avoid pure bottom-up planning (teams lack full organizational perspective and become emotionally invested in their proposals), don't introduce new ideas during planning (too hectic for meaningful innovation—develop separately through 'Funding Proposals'), and provide clear frameworks with metrics, investment guidelines, and 'even over' prioritization structures. Critical practices include killing bad ideas quickly, minimizing cross-team dependencies, recognizing headcount planning won't perfectly map to plans, and treating plans as hypotheses that emphasize learning and iteration. The framework suggests holding back ~20% budget for flexibility and focusing on impact over detailed project management. Engineering leaders will learn that planning's core purpose is synchronizing organizational efforts and creating alignment through a collective 'forcing function' to get 'on the same page.'