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The reason you are not able to do this is because Kris is part of 2 different hierarchies. Kris appears in Org 2 but also in Org 3 under Jeff's (Org 1) Organization. You will need to make sure Org 2 shows both Jeff and Kris to be able to get the right count. See screen shot below.
Do you need to be able to count the total number of times "Kris" appears in your dataset? In that case, you will have to setup a calculated Field.
Thank you for the reply. Yes, I understand Kris is in different organizations and that's what is causing me the issue.
If I were to count the number of time Kris appears in my data set, how would I do that? Can you help with the formula I write in the calculated field?
I am afraid, even after that, when I pick a value in the filter, the count will be incorrect, because it'll try and limit the count to the filter selected.