It can be a real difficult situation, and from my experience, its not uncommon to be at or near one of the following two extremes:
1 - The attitude of the "Boss" is that what we are doing is working, so we don't need technology. They have no clue about how to utilize technology, and almost seem not to want to know. Perhaps that a defensive reaction because it means that part of the business is being "run" by something the boss has no working knowledge of.
2 - The attitude of the "Boss" is that you can do anything with the web, so how come we don't have it already.
I've also run into the problem which starts something like:
Me: Ok Boss, what is it that you want to do?
Boos: Tell me what I can do and what are my options.
I, like others, have found the use analogies as one method that often has worked well. Some of more well-used go something like this:
How does it work
You don't have to be a mechanic to drive a car.
Why is taking so long to get started, or when can I see a sample screen
You don't start building a house without drawing up and approving the plans
Why do I need two of them - Do we need redundancy
There is a reason why commercial airplanes all have at least two engines.
What are my options
You need to travel from Los Angeles to New York (or two appropriate cities a few thousand miles apart) - You have several options - Ride a Bike, Drive a Car, Take a Train, Fly Commercial, Charter a Jet. How fast do you need to get there, and how much money are you willing to spend?
On a different note, I have also tried to understand what the boss is really after, but having him/her explain to me the actual business problem that needs to be solved. I've found it much easier to communicate at the business problem level, as espoused earlier in this thread.
The bottom line is of course, that communication is the key, and just like any teacher, professor, public speaker, or even an author, we have to talk on the level of our audience to be successful. Good Luck
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As a circle of light increases so does the circumference of darkness around it. - Albert Einstein