The problem is that you are caught in a catch 22. You don’t understand enough about their jobs to recommend ways that digital can help, and they don’t know enough about the web to make suggestions either.
Start by asking them about their job. What is it that they do in a typical day? You might even choose to shadow them for a day so you can see what they get up to.
Ask them what is the hardest part of their job. It often helps to focus on communication problems because the web is exceptionally good at helping in that area.
Next, ask them about the biggest complaints they receive from either customers or colleagues. You often find opportunities in these kinds of problem areas.
Then ask them about their future plans. What new areas are they looking into? What opportunities do they see in the future? This can often spark conversations where digital can play a role.
Finally talk specifically about the website. Do they like it? What issues do they have with it and why?
Tools that might help
Finally, you might also want to check out my post on how the web can be used as more than a marketing tool.
I hope that helps and good luck!