It is difficult to ascertain the etymology of this phrase. It is seldom attested in texts from the colonial period and prior, and might have Northern origin if one of the interpretations below is correct.
In current Vietnamese, the form vụng chèo khéo chống is absolutely the dominant form of this idiom, and usually interpreted as roughly "bad at rowing, skilled in moving the boat with a cane". However, some articles suggest that the last element of this phrase might be instead trống (“drum”). This vụng chèo khéo trống ("bad at (acting in) chèo, skilled on the drums") form is attested in Nam ngạn chích cẩm (1918), which is a work written in a Northern Vietnamese dialect when the ⟨ch⟩-⟨tr⟩ merger already completed, as seen the multiple unetymological spellings involving these initials, including one in the title of the work.