Plan a few steps ahead
When writing, where one on one is not possible, try to think through how the person you’re writing to will react, then prepare accordingly. What information will they want? What next steps can they anticipate?
Incorporating such details into your draft shows you’ve considered the issue from their perspective, also—and if this is a business discussion, it can provide a useful way to move past the uneasy news or awkward request you had to deliver higher up the corporate ladder.
That said, if you find your contingencies approaching a level of complexity better suited to a flowchart, perhaps just keep things short and open-ended, then see which way the recipient steers the conversation.
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