For example, Davis created a video when he wanted to automate certain HR processes, such as hiring and payroll. He knew that Bowdoin's president didn't want to mess with HR and that the only way to convince his boss was to show him just how broken the business processes were. So Davis made a video that showed exactly what it took to hire someone and pay them. The CIO showed the video to Bowdoin's trustees, who gave him their blessing, and the president soon followed.
9. Get other people to back you. Another strategy for winning arguments with or persuading the CEO is to build an army of supporters. Davis employed this strategy when he was trying to convince his boss to invest in a multimillion-dollar student information system to replace a costly, inefficient home-grown system.
First, he spent a year rallying the support of students and faculty, who began pushing the president for the upgrade. The president still wasn't convinced. So Davis worked on reducing the cost of the project and getting the trustees to back him. Three years later, when the president saw that the college community was behind the project--and all the business process changes it was going to create--he gave it the green light.
10. Play to the CEO's desire to be successful. A second reason why Bowdoin's president authorized the student information system implementation was because doing so would make him very popular on campus, given the support the project had from students, faculty and trustees, notes Davis. If the president put the kibosh on the project, he might have become the enemy of everyone in the community.
11. Watch your pronouns. Don't make the CEO look stupid. If you're having trouble getting through to your CEO and you're starting to get frustrated, an argument can take an ugly turn. And the more emotional the argument gets, the more likely you are to lose it. So take a breath and be careful of what you say and how you say it.
For example, says Wentworth, instead of telling the CEO, "You don't understand," which makes the CEO look stupid, say, "I'm not sure if I was clear in the advantages I was trying to stress." In so doing, she adds, you take ownership of the problem and give the CEO the opportunity to ask questions. "He won't ask you to tell him more if you're telling him he doesn't get it," Wentworth notes.
12. Put your job on the line. One of the most dramatic statements you can make to demonstrate that undertaking a certain project is in your company's best interest is to tell your CEO--in all seriousness--that you'll leave if the project isn't successful.