The best time to ask this question is when you’re talking to a customer. The next best time to ask this question is when you’re talking to someone on your team who regularly interacts with your customers. This is a question designed to generate ideas–lots of ideas from many sources. So your job with this question is to ask it of as many people as you can, as often as you can.
The worst possible position to be in when it comes to ideas is to have too few of them. That’s why the primary rule of brainstorming is to amass quantity, not force quality. Unfortunately, many people forget this rule, ask for ideas, stifle the conversation by judging each idea as soon as it’s mentioned, and then wonder why their people just don’t brainstorm well. If you want to hear about ideas that might make your customers happy, you need to generate lots of ideas and consider them all–even the ones that are too costly, too time-consuming, or too outrageous.
Creativity is messy. The best ideas never appear fully formed and practical. They are often hidden inside an idea that is impractical and silly. These best ideas need to be coaxed, nurtured, and defended. Creating an environment that encourages creative thinking isn’t always easy, but it’s usually fun.