Using a template column, as suggested, allows you to control your binding pretty precisely. So you can have as many asp controls inside a single column as you want, with appropriate databinding expressions for each. Keep in mind, that you can also have a databinding expression that calls a function in your code behind file. For example, you could have this function in your code: Public Function GetAutoAssignIndex(ByVal AutoAssign As Boolean) As Integer Dim index As Integer = 0 If AutoAssign = True Then index = 1 End If Return index End Function Your databind might look similar to this: This example is for a dropdown containing objects with an "AutoAssign" property defined.