The correct way to measure with traditional measures
Things to remember (see diagram below)
The tip of the measures goes to the nearest point on the bowl first and the adjustable end is then taken to the nearest point on the jack.
The adjustable end must always touch the jack, not float above it.
The measures must not rest on the ground.

The correct way to measure with the Bowlsline string measure
The principle of the fixed end touching the bowl first and the adjustable end then taken to the jack still applies, but both ‘ends’ must be in line, square to the bowl and jack, and rest securely on the ground.
Note that the arrows on both sides of the equipment are in alignment.

Long Tapes
With long tapes, the fixed end (tip of the tape) goes to the bowl and the adjustable end (the housing of the tape) goes to the footer. The measurement is taken from the middle of the footer to the nearest point of the jack. The distance should be at least 19 metres to be considered a mark.
References From the Laws Of The Game
D.10 MEASUREMENTS: are taken between the nearest points of the jack and a bowl with nothing to lie between. The adjustable end of an approved measure must be taken to the jack. In the case of the footer the adjustable end of the certified tape is taken to the centre of the footer.
4.2 A mark is set when the jack having been bowled, does not go off the green, is not prevented from
going off by resting against anything at the edge or in the channel or, after lawful objection, is proved by measurement, with a certified measure, to be at least 19 metres from the footer, with the footer at least 1 metre from the edge.