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I'm surprised how much time is spent thinking about planning and execution, and so little is really discussed about defining goals well. Because I've found that goals are often really vague, and frequently, they shift. And, shocker, if you change your goals you need to change your plans. Also, if you're not able to see progress against your goals, you probably need to change your plans.

A basic framework like "SMART" can help. But it does require some careful management; people can get really, really conservative if you're not careful, i.e., "undercommit and overdeliver" becomes a mantra. Some engineers and their direct management will throw up a lot of roadblocks to avoid looking bad.

This tension between trying to deliver consistently vs trying to take on bigger problems absolutely wrecks plans. If you want to deliver consistently, just focus on small problems. But not all problems are small, and some are even hard to break down because there's a lot you simply won't know. Periodically redefining and re-evaluating your goals is probably "step 1" in this process, and from there, the plans should flow.




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