by Meridith Levinson

How to Argue with the CEO–And Win

Jun 13, 201111 mins

Can't persuade the CEO to approve that infrastructure upgrade or software development project? The following 13 tips, culled from current and former CIOs and communication consultants, will get the CEO to see your perspective when arguments about IT spending ensue.

Arguments with the CEO are an inevitable aspect of the CIO role, whether they’re knock-down-drag-out battles or civil attempts to persuade the CEO on IT matters of importance. They arise in large part from CIOs’ inability to communicate on the CEO’s level and from CIOs’ and CEO’s diverging views on how best to spend the company’s money.

CIOs who’ve never previously reported to CEOs may be particularly wary of arguing with their corporate commander in chief, and understandably so. Ending up on the wrong side of the debate could put a bullet in their careers.

But CIOs who think they should avoid any kind of confrontation with their CEOs are mistaken. Not every CEO wants to be surrounded by Yes Men; some encourage debate and dissention.

“You’re not just there to be an order-taker,” says Peter Kretzman, a former CIO and CTO turned IT consultant.

Adds Bill Rosenthal, CEO of Communispond, a leadership development firm that specializes in communication, “The more successful CEOs recognize that a diversity of opinions often makes their organizations run better.”

Scrapes with the CEO don’t have to end badly. The trick to squabbling with the CEO—and winning (that is, convincing the CEO of something that will truly make your organization more successful)—is to understand your CEO’s leadership, personality, communication and decision-making style. You also need to speak in business terms (surprise, surprise) and remain respectful. Current and former CIOs and communication consultants share 13 more tips—learned from first-hand experience—for persuading the CEO.

1. Consider your enterprise’s culture. CIOs who are joining organizations that have had nothing but problems with IT can expect battles on every front, since their CEOs will be gun-shy about starting new projects when previous efforts failed.

CIOs in failure-ridden environments will likely have to navigate steering committees and portfolio management processes to get the green light on IT spending, says Mitch Davis, CIO of Bowdoin College in Brunswick, ME. To build credibility in these organizations, CIOs must respect these processes and prepare bulletproof business cases for IT investments, says Davis.

2. Consider your CEO’s style. Some CEOs like to take risks and pride themselves on their quick decision-making, while other CEOs are much more conservative. CIOs need to know which style of CEO they’re working for so that they know which communication techniques to use to influence them, says Lisha Wentworth, a senior consultant with Ouellette & Associates and a contributing author to the book, Unleashing the Power of IT (Wiley 2011).

Davis knows that his boss, Bowdoin President Barry Mills is an ENTJ, according to the Myers Briggs personality type index, which means that Mills is quick to grasp complexities, absorb large quantities of information and make decisions. Thus, Davis knows to be succinct with his explanation of projects he thinks the college should pursue. He also knows to address Mills’ specific concerns about IT, which are, what effect will the project have on people; will it enable the college to move faster; and will it enable the college to make more money.

Rosenthal, the communication consultant, says he once worked for a boss who said no to everything. The boss, it turned out, said no to filter people who weren’t serious about their ideas or requests. “I realized over time that to be persuasive, I had to accept two no’s to get an audience,” says Rosenthal.

3. Speak in business terms. Nick Goss, CEO and managing consultant of Polardene, says the arguments he’s observed between CIOs and CEOs and that he’s had as a former CIO and CTO stem from a failure to speak the CEO’s language.

“If you’re couching any IT expenditure or effort in non-business terms, two things are going to happen,” says Goss. “One is, you’re not going to be understood. Second, you’re not going to be relevant to the CEO’s agenda because CEOs are worried about growing top line revenue, expanding into new markets, increasing the stock price, reducing operational risk and improving the public perception of the company. When you’re talking to them, you have to couch your objectives in terms of their objectives.”

For example, if you’re making a case for a bigger IT budget, Goss recommends breaking your various IT costs down according to the business activities they support. “Typically, an IT budget is couched in terms of IT silos: The data center costs this many millions of dollars. Application development costs this many. Staff development that many. Maintenance costs that many, etc.,” says Goss.

Instead, show what percent or amount of data center costs support a particular business activity or outcome. Do the same for the other elements of the IT budget, such as maintenance and application development. Goss knows this is difficult but he says activity-based budgeting will prove to the CEO that IT is not simply a cost center.

4. Be brief. Ouellette & Associates’ Wentworth says one of the mistakes CIOs make when trying to persuade the CEO is being long-winded. “CIOs don’t get to the point,” she says. “They go on and on, and CEOs don’t have the time to listen to them.”

Arguments ensue when the CEO gets frustrated by a CIO who carries on about technology. Focus your pitch on what you want to do, the cost of the effort and the business outcome. If your pitch interests the CEO, she’ll dig deeper, giving you the opportunity to provide her with more information.

5. Anticipate the CEO’s questions. Kretzman says seemingly obvious questions sometimes flummox IT leaders as they make a business case to the CEO. “I’ve seen tech people put together discussions that don’t have any reference to the cost or timeline [of a project] because they get so caught up in the technology,” he says.

Be prepared to answer the obvious questions the CEO will ask, he adds, which include: How much will it cost? When can we have it? What else gets pushed aside if we do it?

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.

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.

“There is no cover for a CIO who works for a president [or CEO],” says Davis. “It’s a no-excuse environment. The projects are too big and there’s too much money associated with what you’re doing to say it’s not going to work.”

13. Know when to fold. “If you’ve presented your case in business terms and the CEO says you still can’t do it, suck it up,” says Goss. “They’re the CEO, and at the end of the day it’s their call.”

So what should a CIO do when the CEO is saying no to a project, budget or timeline that you know for a fact will endanger the company?

Kretzman left a job where the CEO was leaning on him to implement a CRM system on a timeline that Kretzman knew was way too aggressive. The CEO wanted the company to begin using the software as soon as it was installed. Forget training. Forget a phased approach. Kretzman knew this was a disaster waiting to happen, so he high-tailed it out of the company.

Kretzman says the CRM implementation was a disaster and that the company ended up abandoning the software at a high cost. If Kretzman had stayed, he would have been associated with a failed project.

A CIO should leave a doomed project the same way any other executive should leave a company engaging in fraudulent activity, notes Kretzman. “If a corporate counsel or a CFO is told to turn a blind eye to illegal activity, you have to be willing to exit the position,” he says.

Meridith Levinson covers Careers, Project Management and Outsourcing for Follow Meridith on Twitter @meridith. Follow everything from on Twitter @CIOonline and on Facebook. Email Meridith at