I always get inspired by our InformationWeek 500 ranking, research, and reporting. But our annual profiles of the most innovative users of business technology always deliver a swift kick in the pants as well. That pants-kicking feeling was particularly strong this year. I kept thinking about the hard questions that our profiles of various innovative companies should raise for anyone reading them. I settled on six, but I'd love to hear yours as well.

1. What opportunity is so big that it scares us?

Think about what UPS did this year. For five years, UPS has let its customers intercept a package they're having shipped and reroute it during delivery. That takes remarkably complex technology and processes. Now UPS is multiplying that complexity by letting package receivers reroute packages, with a service called My Choice.

"We have millions of shippers, but we have extraordinarily more receivers, and the idea to empower them to essentially shift on demand what the driver was doing every day was a big leap for us," says UPS CIO Dave Barnes.

[ One of the greatest potentials of big data is the ability to let users search and analyze streaming data in real time. Read How Topsy Tames Twitter's Big Data Fire Hose. ]

UPS knew five years ago that package receivers would like to reroute packages--if they ordered a new iPad online but were suddenly called out of town, for instance, to let a neighbor sign for it or have it held at a UPS store. But technology wasn't up to the task. Servers and databases couldn't deliver the pure processing speed needed to give millions more people the option of finding their package and changing its routing, and do so with the real-time reaction time we expect on a Web or smartphone app. UPS kept the vision of that big opportunity in view and kept chipping away at the technology barriers. "In the ideation, it's easy to come up with 'we see the customer needs, we see opportunities, we can meet them,'" Barnes says. "The next layer is the engineering side."

2. Is our IT team good enough to build customer-facing apps?

Let's admit something: Software used by your company's paying customers faces higher standards than those used by employees. There's less margin for error, and if something does go wrong, there has to be a "fix it now" mentality, not "we'll add it to the list."

Vail Resorts' IT team feels the pressure for perfection with its EpicMix app for skiers and snowboarders at its resorts. It's incredibly rewarding to work on customer apps, says CIO Robert Urwiler, but IT can't pretend that it's the same as building internal IT systems. "I don't know that every CIO will be able to make the transition, and it frankly creates a different kind of IT organization," Urwiler says.

Customer-facing software is a big part of this year's InformationWeek 500 innovations, and the ideas almost always come from a mix of marketing, product engineering, and IT teams. High quality and fast turnaround are nearly always requirements of the business plan. Will the marketing and product teams be eager to rely on IT when it comes to serving customers?

3. Are we spending enough time studying our customers' needs?

CUNA Mutual Group launched a smartphone app that lets people apply for a loan, even while they're standing on the car lot. That started from CUNA Mutual teams thinking about the company's credit union customers, and their need to attract younger customers to take out more loans. Smartphone apps seemed to offer potential, so CIO Rick Roy took a few IT and product people who understood CUNA's lending software and had them learn about mobile and come back with a prototype. CUNA Mutual has landed more than 40 new customers for its lending software since offering the smartphone app as part of it.

4. Do business units turn to us when they have an idea that needs fast action?

USAA has taken agile development beyond IT. Called "Agile Labs," the initiative puts product experts, customer service reps, and IT pros together in a workspace to whip an idea into a prototype. It delivers 45% faster than its traditional waterfall development approach, USAA says.

Several InformationWeek 500 companies this year flagged the importance of getting business unit experts right in the middle of the agile process. Deere & Co. puts IT, product, and engineering people all in one location for certain agile sprints--including putting them all right next to a John Deere tractor they used for key testing efforts.

If IT is seen as slow, it will kill credibility with product development and marketing teams.

5. Are we helping business colleagues run their own analytics, and break their dependence on IT?

Look at Beth Israel Deaconess Medical Center, where clinicians, based on their roles, get select access to Clinical Query, a database of 200 million data points on more than 2 million patients. With that platform, they can do research such as searching for people who had certain combinations of conditions and treatments.

Instead of guarding data, IT needs to be seen as the expert at setting data free. If a supply chain specialist gets a wild hair about a way to cut costs, can she run the numbers without asking IT for a report? Freeing experts to run their own what-if scenarios, rather than relying on IT for stale reports, is where big data turns into dollars and breakthroughs.

6. What do we do next?

Deere & Co. built a telematics platform that lets John Deere dealers remotely monitor a farm or construction vehicle and load software onto it if there's a code fix for a problem. Now Deere has to sort out some tough questions about what it should do next with this vital new connection to customers.

Should it let third-party app developers create software for the platform, the way Ford is trying with the software inside its cars and trucks? What new services could Deere dream up for customers via wireless? And how much tech is too much for customers?

Do you have some hard questions that IT organizations should be asking themselves? Share them below and keep the inspiration flowing.

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