How to Push Back on an Unrealistic Deadline From Your Boss
How to push back on an unrealistic deadline from your boss: say yes to the goal, then return within a day with the math, 3 options, and your pick.
Notes from strategy work · decisions · reporting · AI
Protect your judgment, and your reputation. Waiting for perfect information is a decision too — usually an expensive one. Pick Enough is where I write down the rules I actually use to decide, report, and work with AI when the clock is running.
How to push back on an unrealistic deadline from your boss: say yes to the goal, then return within a day with the math, 3 options, and your pick.
How to escalate an issue without going over your boss’s head: decide by authority, go to your boss first with a proposal, and escalate together. Free email template.
How to ask your boss to make a decision: one line, two or three options with your recommendation, and their questions answered before they ask. Free email template.
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Short answer: A pre-mortem is a short meeting held before a project starts. The team imagines the project has already
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