How to Argue with the CEO--And Win

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.

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Mon, June 13, 2011

CIO — 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.

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