As any CIO will tell you, the buck doesn’t always stop at all, let alone with the CEO. More often than not, upper C-level decisions are made and then passed down to IT for implementation. TechRepublic contacted about a half dozen CIOs and CTOs and asked them about their most difficult business decisions. We found that those decisions can be boiled down into two categories, as the stories below demonstrate: decisions that lead to a major shift in the way the company performs its everyday tasks, and decisions that entail the creation of systems and applications that never existed before.

Not doing it the way it’s always been done…
Some of the toughest decisions a CIO will make aren’t tough because they require a lot of thought. They’re tough because they come out of nowhere.

Bill Glassen, director of IT at Cashman Equipment, recalled such a decision back in the late 1990s. He had to decide, quickly, how to get day-to-day information and reports to management-level employees in a way that would allow them to continue to do their jobs, but by using a system that was new. He had to do what had not been done before—very scary ground in conservative corporate America.

Glassen recalled that it amounted to an immense change in corporate communications, “almost a cultural change for our company.”

The company had, historically, accumulated and distributed data through the old general ledger and the AS/400 system. While the AS/400 backbone would remain, the company had decided to move away from the old general ledger system. Glassen was directed to deploy this decision.

Glassen said he had no way of knowing he was about to make the most difficult decision of his career. He was, after all, not changing the way information was accumulated, only how it would be deployed. What he and his colleagues did not understand, at first, was they just couldn’t do what they’d always done.

Initially they tried “the path of least resistance” by building on the existing system during the deployment. “That was a major mistake,” Glassen said. “We assumed we could use the same reports and indicators that we did before…. What ended up happening was no one could communicate. Everyone was looking for information on the new system, but they were looking for it the old way.”

After reviewing the resources they had and how best to get information into the hands of the employees who needed it, Glassen decided to set up a company intranet.

To implement this decision, Glassen and his associates met with management-level employees and immediately encountered the path of maximum resistance. “Everyone wanted their information at 6 A.M. every morning in the same format they always had their information,” he said. “I was the one who had to tell everyone they weren’t going to get what they got in the past. What they had before wasn’t going to work now.”

At first, all the management level could see was bad news. Not only would they not receive the financial reports in the same format as in the past, but the reports they were going to get were not going to be relevant to the old data format. Glassen’s team also encountered difficulty in getting information from management-level employees. Then there were headaches when employees saw initial figures from the intranet and thought the company was losing money when, actually, it was making money.

Glassen found he not only had to explain to the employees at large the benefits of an intranet, but also had to explain to them how to use an intranet. “They needed to know how to work with the new system,” he said.

“What we needed to do was reinvent the whole Hyperion model and to restructure finances into a whole new set of reports and other means of communication,” he said.

New report templates were developed. “We changed the way we looked at our information and our numbers,” Glassen said. “Once we had this in place, we would be able to change the numbers from one year to the next.”

What they were not going to be able to do was make it relevant to prior years’ reports. The company’s decision to move away from the old system effectively meant looking at the same numbers in a whole new way.

Glassen recalled that there were growing pains during the transition. “It was a very tumultuous period,” he said.

However, the benefits of disseminating the new reports over a company intranet soon became clear. Management-level employees soon realized that they could be more flexible in the kind of information they shared and requested. And it was simpler than the old system. “The end user still had their day-to-day tools they needed to do their job,” Glassen said.

That deployment was almost half a decade ago and Glassen said he has seen other deployments and tough decisions since then. But he said he learned from that one. “I learned that I just can’t let things go like that,” he said.

Doing what hasn’t been done before
Back in the 1990s, Nancy Markle set out to do what reportedly had never been done.

Now President Elect of the Society for Information Management, Markle was almost a 30-year IT veteran when she approached her career’s toughest decision. She was then America’s CIO for Arthur Andersen and was responsible for strategy and change for the Global Technology Organization and for meeting business needs with technology solutions for the firm throughout the US, Canada, and Latin America. Markle was informed of a company decision to buy some branch offices from Wells Fargo.

At first glance, this may not seem like a serious IT issue. “And if we had been a normal bank, it would have been no problem,” Markle said.

But there were other issues involved, including changes in the business ledger and trends toward business banking. There also were federal requirements that said Markle had only six months to bring the new branches on board. “So we had six months to bring up four new lines of business,” she said. “And we had to do this on the application and the system side.”

Markle had to decide how to do this and do it quickly.

Despite the short time period, Markle said she knew she would need input from employees at the management level and above, so she went out and got it. She also got input from senior consultants and other experts in the field. And she had one question for every one of them: Has this been done before? “And every one of them said, ‘No. This has never been done before.'” Markle also noted, grimly, that quite a few consultants indicated they would be willing to take control of whatever decision she implemented, provided it showed signs of success.

Markle didn’t implement a single decision. Instead, it had multiple tiers. For instance, she decided to outsource the applications merger. “This meant our first outsourcing experience,” she recalled. “It would become our largest outsourcing experience.” However, Markle said this part of her decision would help provide the applications merger in the time she had.

Markle also wanted the additions of the four new branches to be as seamless as possible. This meant training for bank employees in such a way that they would be comfortable during and after the new deployment. She also wanted to maintain the bank’s history of professionalism and service.

The six months passed very quickly, but Markle got the results she wanted. The systems and applications were merged seamlessly and with very little publicly noticeable difficulty. Markle said this happened not because she made the right decision, but because she made the right decision that was carried out by a team, which included the company’s chairman and vice chairman.

“CIOs don’t make decisions by themselves,” she said. “Systems are a tool of business. The goal of a CIO, in my opinion, is to be a part of the decision making process.”