Virginia Heffernan writes in the NYT Sunday Magazine:

Drill, Baby, Drill
The word “drill” has come to define bad teaching. The piercing violence that “drilling” evokes just seems not to belong in sensitive pedagogy. Good teachers don’t fire off quiz questions and catechize kids about facts. They don’t plop students at computers to drill themselves on spelling or arithmetic. Drilling seems unimaginative and antisocial. It might even be harmful.

“In educational circles, sometimes the phrase ‘drill and kill’ is used, meaning that by drilling the student, you will kill his or her motivation to learn,” explains Daniel Willingham, a University of Virginia professor of psychology who has written extensively on learning and memory. “Drilling often conjures up images of late-19th-century schoolhouses, with students singsonging state capitals in unison without much comprehension of what they have ‘learned.’” ...

Oh, those schoolhouses — with the hickory sticks and the dunce caps. “Harrisburg! Salt Lake City! Montpelier! Tralalalala!” That does sound kind of fun — I mean, authoritarian. And drilling hardly has a better reputation outside academia. On message boards, students complain bitterly about Kumon, the extracurricular Japanese system of worksheet drills that many also admit has made them superb at math. Only unsportsmanlike parents hellbent on raising valedictorians, it seems, require their kids to do such rote work. At the same time, parents dismiss cutesy, flashy apps and Web sites that drill students using elaborate animation (like PopMath for arithmetic, iFlipr for custom flashcards, Cram for custom practice tests) as superficial edutainment, on par with children’s TV.

Willingham also approves of drilling as a way to measure what you’ve learned. “Testing yourself is really good,” he told me. “It actually leads to better learning than studying” — e.g., reading passages over and over, sometimes with a highlighter. He explained, “You can’t be proficient at some academic tasks without having certain knowledge be automatic — ‘automatic’ meaning that you don’t have to think about it, you just know what to do with it.” For knowledge that must be automatic, like multiplication tables, “you need something like drilling,” Willingham wrote. He also warned, “You’d hope to make it a little less boring for the student.”

Here’s something I’ve found that makes drilling not boring: colorful, happy apps.

By the way, the family of the Mr. Kumon who founded Kumon in Osaka in the 1950s now owns $400 million dollars worth of Kumon stock. The funny thing about Kumon is, last I checked, it is resolutely low-tech: it was completely paper and pencil drilling. You fill in a huge workbook of problems, then you give it to the Asian lady who owns the franchise, she grades it by flipping through the pages at amazing speed, then she gives you either a higher level workbook or one of their endless supply of additional problem sets at the same level.

Computers can make this more efficient by grading tests automatically. Moreover, they can shuffle questions on the fly so if you are doing badly, the computer can lower the difficulty until you get the hang of it.

The big question is whether math drilling programs can do what a first-rate tutor can do: figure out why you are making a recurrent mistake and explain it to you in a way you'd understand. In theory, it doesn't sound impossible, but here we are, in 2010, and I've never heard of anybody in Silicon Valley getting as rich off math tutoring as Mr. Kumon did.