Currently we do not support binding to the ToggleState.Indeterminate state automatically because it would require a change in the behavior of the Checked property. If you use the CheckedMember, the ToggleState.Indeterminate state is represent like ToggleState.On. 

Workaround: 
Subscribe to the NodeFormatting and NodeCheckedChanged events: 
void radTreeView1_NodeFormatting(object sender, Telerik.WinControls.UI.TreeNodeFormattingEventArgs e)
{
    Child child = e.Node.DataBoundItem as Child;
    if (child != null)
    {
        e.Node.CheckState = child.Status;
    }
}

void radTreeView1_NodeCheckedChanged(object sender, Telerik.WinControls.UI.TreeNodeCheckedEventArgs e)
{
    Child child = e.Node.DataBoundItem as Child;
    if (child != null)
    {
        child.Status = e.Node.CheckState;
    }
}