Relationships between the CIO and business executives will inevitably become strained, with broken promises and eroding trust. So how do you keep them from going completely off the rails?\n \n \u201cThat\u2019s the time that is actually the true test of leadership,\u201d says Robert Webb, CIO of Hilton Worldwide. \u201cIt\u2019s the ability to know when that\u2019s happening\u2014to sense it and see it\u2014but also to be proactively communicating when you know that\u2019s starting to occur.\u201d\n \n Webb and his team have helped develop a new Expanded Rewards loyalty program, which allows guests to use points and cash for a wider range of perks at Hilton properties. It\u2019s a complex system that\u2019s already in place at several thousand hotels. When Webb started working with the business sponsor of the project, he admits that neither of them thought they would succeed. In fact, the project didn\u2019t really begin to click, he admits, until people from IT, marketing, HR, finance and other departments on the steering committee worked through the change management and business process issues in 85 countries and 10 brands. Now the program is close to full deployment. \n\n \n But not every effort has gone so smoothly. Two years ago, Hilton decided to outsource the hotel help desk to a large global outsourcer\u2014a fairly standard move for a large company. However, no one had recognized that this wasn\u2019t a traditional break-fix support group; it handled intricate, business-specific processes for some of Hilton\u2019s most sensitive partners. \u201cAnd some of these people were not happy about the communications challenge of explaining to somebody who\u2019s not worked in the inside of a hotel what it means to, for example, do the night audits,\u201d Webb says.\n \n When he got together with the brand leaders involved in that partnership, instead of spreading blame, they examined the IT and business metrics of the contract. It quickly became clear that not only did the metrics need to be redefined, but that the business goal was no longer the one they had identified at the outset. They talked openly about how the criteria for success had changed. (For more on how Hilton improved business relationships, see "How CIOs Build Bridges With Other C-Level Execs.")\n \n \u201cWe\u2019re only able to solve this with truthful, honest communication,\u201d Webb says. \u201cWhen people say \u2018This is hard, I\u2019m not sure I\u2019m with you anymore,\u2019 you need to get everyone to remember it\u2019s about one team, one vision, and let\u2019s get grounded on why we did this.\u201d\n Contact CIO Executive Council Editorial Manager Diane Frank at firstname.lastname@example.org. Follow her on Twitter: @dtwfrank.