This task requires extensive vba coding to do in Word. If you don't know how to write code then it is WAY TOO DIFFICULT for you to attempt.

Nothing like this can happen 'automatically' without the computer being told via VBA:
1. What to put on the left hand column and in what order (presumably randomised in some way)
2. What to put on the right hand column and in what order (presumably also randomised)
3. How to relate elements on the left to elements on the right
4. What the lines should look like in terms of colour/thickness/positioning
5. How to reveal the lines one at a time in response to some user-initiated triggers.

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Andrew Lockton
Chrysalis Design, Melbourne Australia