Goss says a "completely reasonable question" caught him off guard when he was making a case for firewall technology while working as the technical director for IT outsourcing company Digitas. The question: "Why do we need to spend this much money? Why can't we just spend 80 percent?"
Goss says he had no immediate answer to the question because he hadn't anticipated it. Goss realized the COO, who asked it, was trying to figure out what level of risk the company might incur if it spent less money on firewall technology. Goss went back to the drawing board, and he and his staff rewrote their case in terms of risk. Goss then received approval for the investment.
6. Don't take the CEO's questions personally
Arguments can erupt when a CEO's questions push a CIO back on his heels and make him defensive. Push aside your ego and realize that the CEO's job is to ask questions.
"A CEO got to where he or she is by being a critical thinker, and a critical thinker doesn't just accept what they're told," says Kretzman. "They look for the weak side [of arguments]."
7. Give the CEO realistic answers
Nothing frustrates a CEO more than a CIO who over-promises and under-delivers. "CEOs get really impatient and frustrated when they can't get clear answers to questions, or when they get answers that they don't have confidence in," says Kretzman. "If you say a project will cost this much and you're always wrong by 50 percent and off schedule by six months, sooner or later that will lead to an argument."
Unrealistic cost and schedule estimates also erode a CIO's credibility, adds Bowdoin's Davis. "It's better to go in with the right project at the right price and explain why it has to be this way than to build something that won't be as stable," he says. "You'll reduce trust in IT across the company and with the CEO."
8. The medium is the message
PowerPoint won't always make your point. Sometimes you have to get creative when you want to convince the CEO to back an organizational change.
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.