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Your collegue has a valid point but I think he underestimates the need for assistance in the field.
It is a big challenge to avoid detrimental effects on the usibility and experience of using the application, but worth it in my opinion.
Unfortunately I have never needed it, so have no experiences to share.
I think you may end up having to weigh up the proportions of users who in need of assistance, and the of users who don't need it yet are adversly affected by its presence.
Whatever you decide, a good idea is to count how many users get part way through the web form (or whatever application) and leave without finishing, and count how many get all the way through. Some of those that laeve half way through might just have changed their mind, but some will have hit a problem and left due to lack of help. This should give you some idea of the impact field level assistance has on your web application - especially if you can do a 'before and after' study (either in testing or over two implementation cycles).
Good luck and we'de (me at least) appreciate an update when you make a decision!
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