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I have over 15GB of emails. I have one employee that requires hard proof in order to understand a concern. Otherwise this person gets very defensive. I hope to avoid this by showing the insane number of tasks and emails that they never completed or replied to, even after bump and reminder emails. So they can't get defensive and we can work on a solution going forward.

So, how do I search all the emails I have sent to a specific person/email, that they did not reply back on, or they were not the last person to reply (in the sense of a chain email, they replied, I replied back, they then didn't)?

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In Gmail I was able to use this search:
"to:(specific person's email address) -from:(specific person's email address) from:me"

This found messages sent to a particular person with no replies from them on that conversation.

Downside: My company sends a lot of messages to mailing lists that include all of our employees, and these messages also match this search. You can keep adding "from" and "to" search terms with a minus side in front of them to help narrow down your search results.

I recommend using the Gmail Advanced search terms to continue to narrow down your results. Perhaps you can include a specific date range or label that is on the messages you are looking for.

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