I really love this (excerpt from a Techcrunch article by Roelof Botha):
Imagine it’s five years from now and your company is a massive success. you’ve got a fantastic product, you’ve achieved market leadership, and everyone else is trying to catch up. What decisions helped you get there?
Now imagine the same five years have passed, but this time your company is struggling. You failed to live up to your original vision. Your product has stalled. You’re backed into a corner. What choices led to that moment?
These two questions are the opening exercise in a strategic planning technique that Larry Summers — the economist and former Treasury Secretary — led the team at Square through recently. The process sparked important discussions about choice, risk and foresight.
Likely a useful exercise to do, whether you’re a startup, a larger company, or a VC, even. Probably useful for personal life, too.