Why Your Strategic Planning Fails (And How to Fix It)

Why Your Strategic Planning Fails (And How to Fix It) I’ve seen more agile planning sessions derailed by politics than by any technical challenge. It always starts the same way. You get the right people in a room—Product, Engineering, Sales, Finance—and for a moment, it feels like a powerful alliance focused on building the future. A spy’s guide to strategy helped me realize these sessions unfold in three acts: Alliance, Competition, and Endgame. ...

October 25, 2025 · 2 min · Aaron Held