Let's assume that you have a simple userform with check boxes and a command button with default names, and in the document you have inserted check box content controls with tags of Check1 and Check2 etc. The userform code would be
Option Explicit
Private Sub CommandButton1_Click()
Me.Hide
Me.Tag = 1
End Sub
In an ordinary module the following macro would call the form and process two check boxes - add as many other check boxes as required using similar syntax.
Option Explicit
Sub RunUserform()
Dim oFrm As New UserForm1
Dim oCTRL As ContentControl
With oFrm
.Show
If .Tag = 1 Then
For Each oCTRL In ActiveDocument.ContentControls
If oCTRL.Type = wdContentControlCheckBox Then
oCTRL.Checked = False
End If
Next oCTRL
If .CheckBox1.Value = True Then
For Each oCTRL In ActiveDocument.ContentControls
If oCTRL.Tag = "Check1" Then
oCTRL.Checked = True
Exit For
End If
Next oCTRL
End If
If .CheckBox2.Value = True Then
For Each oCTRL In ActiveDocument.ContentControls
If oCTRL.Tag = "Check2" Then
oCTRL.Checked = True
Exit For
End If
Next oCTRL
End If
End If
End With
Unload oFrm
Set oFrm = Nothing
End Sub