Seems this may work best as a Pivot table.
If you repeat down the employee name, name in rows and CLE*** in columns and drag the date in question into values.
Otherwise.... I pasted your first example into Excel.
Michael in A3, ENTERDATE in H3.
=VLOOKUP(I4,INDIRECT(ADDRESS(MATCH($H4,$A:$A,0),2)&":"&ADDRESS(MATCH($H4,$A:$A,0)+4,5)),MATCH($H$3,$B$2:$E$2,0),0)
You basically use MATCH to locate where things are on the sheet, then ADDRESS turns them into a reference like $A$1, then INDIRECT turns that into a useable address.
The +4 in the 2nd MATCH is assuming you have 5 CLE items per name, if this is not the case this can be extended but only if the CLE names are always the same per person. Otherwise you'll need another solution.