Are there times when it is appropriate to let someone at the senior/manager level know their emails can be a little dense?

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If you’re a staff level employee I wouldn’t do that personally. Giving constructive feedback about employees with more seniority makes waves and in this job market you don’t want to come across as difficult to work with. Seems like you could just have your company’s AI tool create a summary or check in with them on a call to make sure you understand the email.

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