You're essentially describing pulse and engine-on gliding. Albeit with gentle pulses.
I wouldn't worry about trying to adopt that technique any more than you already are.
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my boss who still swears he got better mpg when he was careless with a Corolla than when he was overly cautious
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If that's the case, the most likely reason is because he didn't know how to drive for good MPG when he was trying to be "overly cautious". Or he wasn't measuring things well.