I'm not sure how much this helps, but I use an extension method on Enum that looks like this:
    /// <summary>
    /// Returns the value of the description attribute attached to an enum value.
    /// </summary>
    /// <param name="en"></param>
    /// <returns>The text from the System.ComponentModel.DescriptionAttribute associated with the enumeration value.</returns>
    /// <remarks>
    /// To use this, create an enum and mark its members with a [Description("My Descr")] attribute.
    /// Then when you call this extension method, you will receive "My Descr".
    /// </remarks>
    /// <example><code>
    /// enum MyEnum {
    ///     [Description("Some Descriptive Text")]
    ///     EnumVal1,
    ///
    ///     [Description("Some More Descriptive Text")]
    ///     EnumVal2
    /// }
    /// 
    /// static void Main(string[] args) {
    ///     Console.PrintLine( MyEnum.EnumVal1.GetDescription() );
    /// }
    /// </code>
    /// 
    /// This will result in the output "Some Descriptive Text".
    /// </example>
    public static string GetDescription(this Enum en)
    {
        var type = en.GetType();
        var memInfo = type.GetMember(en.ToString());
        if (memInfo != null && memInfo.Length > 0)
        {
            var attrs = memInfo[0].GetCustomAttributes(typeof(DescriptionAttribute), false);
            if (attrs != null && attrs.Length > 0)
                return ((DescriptionAttribute)attrs[0]).Description;
        }
        return en.ToString();
    }
You could use a custom property getter on your object to return the name:
public class TestResult
{
    public string TestDescription { get; set; }
    public ExpectationResult RequiredExpectationResult { get; set; }
    public ExpectationResult NonRequiredExpectationResult { get; set; }
    /* *** added these new property getters *** */
    public string RequiredExpectationResultDescr { get { return this.RequiredExpectationResult.GetDescription(); } }
    public string NonRequiredExpectationResultDescr { get { return this.NonRequiredExpectationResult.GetDescription(); } }
}
Then bind your grid to the "RequiredExpectationResultDescr" and "NonRequiredExpectationResultDescr" properties.
That might be a little over-complicated, but its the 1st thing I came up with :)