Arne Duncan was CEO (?!) of the Chicago Public Schools from 2001, and part of the system from 1998. That's more than think-tank or advocacy.
Clinton
travelled to 79 countries, had offices in the West Wing, did a tour on behest of the State Department, and I recall lots of people thought she was an awesome appointment on account of experience, popularity overseas, and knowing the people she'd be dealing with. Plus half the Democratic electorate thought she was qualified to be *President*. And Rice's "qualifications" don't seem to have helped much. As Senator, "She is also a Commissioner of the Commission on Security and Cooperation in Europe[207] (since 2001).[208]"
LaHood seems a fair cop. Locke was governor of Washington for 8 years; appointed after Richardson and Gregg. Napolitano was a governor. Qualifications admittedly not obvious, but there's a clear gubernatorial trend... and governors are traditionally good fodder for becoming President. (What were Bill Clinton's qualifications for running the country? What were George Bush's?) LaHood is Republican and expected to be overshadowed by the committee chair in Congress.
At that level, it's not clear to me if what matters most is area-competence or administrative-competence and political savvy and influence in Congress. Having all would be nice, but there's the Undersecretary level for wonkery.
Gates is almost certainly retained for purposes of continuity regarding the wars we're running, more urgently relevant than his Iran-Contra sins. Blame Bush for the appointment.
Bush:
2nd Education was less qualified than Duncan
http://en.wikipedia.org/wiki/Margaret_Spellings
First one had run schools (not that the Secretary of Education does... not clear what that office *does* do), but in office called the NEA a terrorist organization, backed No Child Left Educated (snark), and got fined for illegal propaganda.
http://en.wikipedia.org/wiki/Roderick_Paige
Mineta, Transportation. Legislature in transportation issues, Commerce under Clinton. Followed by Mary Peters, state and federal transportation administrator. Strong picks.
Mel Martinez, Housing. Had been chair of Orlando Housing Authority but not clear why, career seems to be lawyer+executive.
Alphonso Jackson, Housing 2. Strong pick.
Steve Preston, Housing 3. No obvious housing experience whatsoever.
Spencer Abraham, Energy. As Senator, proposed abolishing the Department. No obvious experience.
Samuel Bodman, Energy 2. Chemical engineering degree, no obvious experience.
O'Neill, Snow, Paulson, Treasury -- CEO of Alcoa; government jobs; Goldman Sachs. None an actual banker.
We'll draw a discreet veil over the Attorneys General, though the third was at least a judge.
Unmentioned Obama appointees:
Hilda Solis, Labor. Congresswoman; father was a union shop steward. Dealt with labor issues through her legislative career, including organizing and funding a minimum wage initiative; seems a strong pick.
Vilsack, Agriculture. Governor of Iowa; previous two secretaries were also farm state governors. Traditional pick.
Salazar, Interior. Seems to have a strong career into Interior-type stuff, which doesn't mean he'll be good from an environmentalist view. Better than his predecessor. Traditional pick.
Shaun Donovan, Housing. Past Housing career in NY. Strong? pick.
Conclusion: yeah, a few of Obama's may seem weak, most obviously in the bipartisan pick (LaHood), but as a whole the Cabinet doesn't seem any weaker.