As for timing, I often ask what the timeframe for a task is. Asking "what's your timeframe for this?" and then responding with a yes/no/maybe on that helps. That also frames it much differently than "when do you want it done by?" or "When should we do it by?" but still basically asking "What's your expectation?"
Also, yes on the whole setting boundaries and dealing with how much work is work.
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As for timing, I often ask what the timeframe for a task is. Asking "what's your timeframe for this?" and then responding with a yes/no/maybe on that helps. That also frames it much differently than "when do you want it done by?" or "When should we do it by?" but still basically asking "What's your expectation?"
Also, yes on the whole setting boundaries and dealing with how much work is work.