My initial take is that there’s actually less to this policy than meets the eye. Obama isn’t ordering federal employers not to explore an applicant’s criminal history or to disregard it; he’s simply deferring the point at which they learn about the crimes of applicants who receive serious consideration. The government will obtain this information for such applicants via a background check.
Obama says he wants employers to look at the qualifications of ex-cons before they disqualify them. But employers typically don’t weigh qualifications against criminality — the two criteria are entirely separate. If your past criminality is deemed to present an undue risk, it doesn’t matter how qualified you are. The federal government presumably uses this common sense approach to hiring.