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When You Suspect the Customer Might Be Wrong

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In these situations, I try to lead the customer to the appropriate decision. The easiest way to do this is to decide on the course you believe meets their needs, and offer it up, and make them tell you what they want that is different. Generally the less technical don't quite know enough of their options to argue something put right in front of them. Of course, this requires that you take some time to really get a good feel for the customer and their business and needs.

In your example, where the client wants to opt-in to a dummied down system, that you feel would have to be changed later I would suggest the following:
1. Stress that it's easier to "get it right the first time", than to fix it (add features) later.

That's not only from a development / project management standpoint, but from a user perspective. Users would have to re-learn the system a second time after the addition of these features.

2. Re-development / adding features costs money. (Shoot, even removing features costs money.) Stress that you feel this is where the user base will want to go, and that the costs will be drastically higher later, including his internal staff training costs, and that he's getting less value for his money if he waits and does it later.

3. If you feel very strongly about it, push for a pilot with some users of the advanced system. You might re-iterate the 1-10-100 rule of project management and stress how important it is to get the direction correct at the design and pilot stage, rather than get to a deployed/ production stage, only to go back to the drawing board.

In general this is going to rely heavily on your people skills. Charisma, confidence, the customer's impression of your experience. Good use of anecdotes of previous customers that you've taken through similar decisions may help. You may also put the project on hold and let him sit and think about it, which will convey how seriously you take this decision.