My answer to How do I help someone get caught up on computer skills for business?
Answer by Ken Larson:
I have found the two biggest factors in achieving that which you have questioned are confidence and motivation in that order.
Start by finding out what the individual already knows and has practiced and build on it. Then move into a closely related new area and ease them into it As they gain confidence they will be motivated to grow further.
Observe what the individual likes or is good at on the computer and use those elements to sculpt how you proceed. As they learn they will stay involved and practice on their own those tools in which they have an interest and in which they grow proficient.