When Les Duncan was a bold lad of three, a backyard bee-catching expedition ended badly, with him sputtering, "Oh damn! Oh damn! Oh damn!" as he fled from the yard.

The importance of risk mitigation was not lost on Duncan, who developed stealthier bee-catching techniques and, before branching out into snake catching, made sure to find out which snakes were poisonous. Now that he’s CIO of Bold 100 honoree Atmos Energy, an upstart utility in Dallas, Duncan has put those early lessons in risk mitigation to good use. When his company acquired a same-size competitor, he had plenty of risk to contend with as he led the integration effort.

Risk mitigation is just one of many strategies that increase the chances that bold gambles will, in fact, pay off. Here’s a roundup of bold leadership secrets from five of this year’s CIO 100 honorees.

1. Build credibility through accomplishment

Bold initiatives are most likely to work if you’ve established a winning track record. From day one as director of IS at Bold 100 honoree Boy Scouts of America (BSA), Nate Langston knew that a portal would vastly improve information access, making it easier for executives and volunteers alike to do their jobs. But the existing IT system was in such bad shape—searches in the membership system took three to six minutes; membership reports often took more than a day to run—that he knew that before he could do anything else, he needed to fix the information pipeline. Accomplishing this reestablished credibility for IT and helped him pave the way for a portal pilot. "When IT comes to a meeting saying, ’You have to do things this way,’ the relationship with our customer starts to go south," he says. "But if I can go into a meeting with a number of wins already under my belt, I get a much better response from the organization, and a willingness to follow where I want to take them."

2. Identify risks and implement mitigation strategies

Before Atmos Energy effectively doubled its size by acquiring Texas Utilities Gas, Duncan had already identified the risks involved in leading the integration effort. In addition to the usual timing and budget pressures, he had to worry about implementing brand-new, untested billing software and the fact that the parent company of Texas Utilities Gas was in the midst of outsourcing its back-office staff and systems. Undaunted, Duncan came up with appropriate mitigation strategies—including negotiating fixed-price contracts, splitting the work into manageable chunks, and doing early benchmarking in Hewlett-Packard’s labs to test and fine-tune the new software well before the scheduled launch date. He also minimized the involvement of the acquired company’s outsourcer, whose employees were worried about losing their jobs and whose managers were resisting giving up the business, by hiring a third-party vendor to handle data conversion. Today, the integration effort is on track to wind up successfully, on time and on budget.