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\u2019s 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\u2019s a roundup of bold leadership secrets from five of this year\u2019s CIO 100 honorees. \n\n1. Build credibility through accomplishmentBold initiatives are most likely to work if you\u2019ve 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\u2014searches in the membership system took three to six minutes; membership reports often took more than a day to run\u2014that 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, \u2019You have to do things this way,\u2019 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 strategiesBefore 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\u2014including negotiating fixed-price contracts, splitting the work into manageable chunks, and doing early benchmarking in Hewlett-Packard\u2019s labs to test and fine-tune the new software well before the scheduled launch date. He also minimized the involvement of the acquired company\u2019s 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. Duncan won\u2019t pull the trigger on a bold move that could radically improve the business until he\u2019s sure he can minimize the risks. 3. Speak your customers\u2019 languageMake it easier for customers to embrace your plan by framing it in terms they\u2019re comfortable with. After Langston presented his portal vision in his second week at BSA, the CFO put an arm around his shoulder and said, "Nate, that may be your vision, but it\u2019s not necessarily the vision of the Boy Scouts of America." BSA leaders saw computers as data entry terminals, not executive tools. In fact, during Langston\u2019s interview, the COO had told him it would be snowing in Texas before he\u2019d put a computer on his desk. After his portal proposals were shot down twice, he repitched the idea as an electronic newspaper and won approval for a pilot, which ultimately led to a full rollout.4. Fight for your visionIf you\u2019ve got a great business case for your bold initiative, don\u2019t back down. At Bold 100 honoree Constellation Energy, CIO Beth Perlman says that her boldness in pushing for such things as a common desktop platform\u2014an effort IT believed in but, given past failures, didn\u2019t think was feasible\u2014has rubbed off on her staff."They saw me always pushing and not taking no for an answer, so they got bolder," she says. Perlman got her common desktop platform, as well as an overhaul of the entire computing platform (servers, storage, backups, management software), garnering the same savings the company had hoped to achieve through an outsourcing deal she convinced her colleagues to nix.5. Pick your battlesWhile it\u2019s important to stick to your guns when it matters, you also need to know when to back down. At Constellation, Perlman picks her battles by deciding what she can and can\u2019t live with. While she can\u2019t live without standards, for example, she might be able to live with putting an extra 10 PCs in the field if users insist it\u2019s absolutely necessary. "If it\u2019s just a difference of opinion and doesn\u2019t make a big difference to the bottom line of the company, it\u2019s not worth fighting about," she says.6. Build buy-in on the front linesBy definition, bold business moves require change. And change requires management. So bold business leaders must make sure that employees who will be affected by the change buy into the strategy. At Bold 100 honoree 7-Eleven, CIO Keith Morrow resuscitated a failing business intelligence project by backtracking and engaging end users. Addressing their specific but relatively straightforward needs got them on board. Similarly, Morrow and his colleagues are involving frontline employees in the rollout of 7-Eleven\u2019s new Model Market strategy. Model Market, which relies heavily on a proprietary retail information system and training technology, empowers each of the company\u2019s 5,800 North American stores to take ownership of product and ordering decisions. An internal trade show and sampling event called the University of 7-Eleven gives store managers and franchisees a sneak peek at forthcoming products and new technologies (such as the wireless store platform rolling out this year), emphasizing what\u2019ll be in it for them to stock the new products and apply the new technologies. "You\u2019ve got to get people involved, excited and energized to where the change is something they\u2019re a part of, something they make happen as opposed to something that happens to them," says Morrow.7. Cultivate champions of changeIn addition to energizing frontline workers, bold leaders must also rally the troops at the executive level. "You have to create champions across the whole organization who will embrace your vision of changing the organization," says Bold 100 honoree UNICEF CIO Andri Spatz. "That will multiply the power of the CIO." Spatz, who boldly chose an IP-networking standard back in 1998 and pioneered running it over satellite two years later, has coached business colleagues to become highly engaged project owners, leading by example. "I banned sponsors who are spectators and instead demanded owners," he says. "Owners have skin in the game. We don\u2019t want spectators, only actors." Through repetition and Spatz\u2019s perseverance, engaged ownership is now an embedded business practice at UNICEF.Engaging obstructionists is also critical. "It\u2019s never easy to change, and there\u2019s always a squeaky wheel," says Perlman. "When certain people speak up, they get everyone else twisted. You\u2019ve got to give them a lot of attention so that they don\u2019t rile everyone up." Perlman identifies naysayers and assigns someone to work with them one-on-one to make sure they come around.8. Shoot for evolution, not revolutionIf bold, transforming initiatives are overly disruptive, they\u2019ll be rejected. "I\u2019ve seen many disruptions that were not evolutionary," says Spatz. "The organization would not embrace them. To make [change] sustainable in the long run, you have to address people, process and technology\u2014without exception, no shortcuts." Although it can be slow and painful to deal with all three at once, Spatz insists there\u2019s no other way to effect change. "Certain things take root; others you keep on reinforcing, reinforcing," he says. "It takes a long time. You need a lot of support, relationship and backbone to sustain changes over the long run."Senior Editor Alice Dragoon can be reached at email@example.com.