First off, I think you did a pretty good job on your Entry sheet. The table is Formatted As Table which is a functionality that too few people use and it's quite powerful.
On the next page, I like the SumIfs you did referring to the column and row headings of that table, Estimator and Date. However, you are kind of reinventing the wheel a bit so I am going to introduce you to your new favorite Excel thing: pivot tables!!!
Look at the attached workbook. I have recreated your table on sheet1 with a pivot table. It took me all of about 15 seconds to set up and once you get the knack of it, you'll bang them out that quickly too. They are wicked easy and, like Format As Table, quite powerful.
I have the dates grouped by month as you have, but could have easily grouped by quarters or days. Just right click on any of the Month headings and choose Group to see how it's done. Pro tip: you usually need to select both the year and the subgroup you want otherwise the pivot will group the Septembers and Octobers of every year together.
I think I got what you want on the last tab, Pivot2, but wasn't sure. Check it out and let me know. If you need any other help on this, just let us know. Cheers!
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