Option Explicit

Private Sub Document_ContentControlOnEnter(ByVal ContentControl As ContentControl)
Dim oFrm As UserForm1 'The name of the userform
Dim i As Integer
Dim orng As Range
Dim sText As String
    If ContentControl.Title = "List 1" Then 'the name of the listbox
        Set oFrm = New UserForm1
        With oFrm
            With .ListBox1 'the name of the listbox
                'the items you want to add
                .AddItem "pizza"
                .AddItem "hamburgers"
                .AddItem "hot dogs"
                .AddItem "garden salad"
                .AddItem "potato salad"
                .AddItem "potato chips"
                .MultiSelect = fmMultiSelectMulti
            End With
            .Show
            With .ListBox1 'the name of the listbox
                For i = 0 To .ListCount - 1
                    If .Selected(i) = True Then
                        sText = sText & .List(i) & vbCr
                    End If
                Next i
                If Not sText = "" Then sText = Left(sText, Len(sText) - 1)
            End With
            Set orng = ContentControl.Range
            orng.Text = sText
            orng.End = orng.End + 1
            orng.Collapse 0
            orng.Select
        End With
    End If
    Unload oFrm
    Set oFrm = Nothing
End Sub

Option Explicit

Private Sub CommandButton1_Click()
    Hide
End Sub

Private Sub UserForm_QueryClose(Cancel As Integer, CloseMode As Integer)
    If CloseMode = vbFormControlMenu Then Cancel = True
lbl_Exit:
    Exit Sub
End Sub