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Bask Iyer, CIO of VMware and Dell Technologies, is not afraid to voice his opinions. “Only the paranoid survive,” he likes to say. “I ask my VMware teams, ‘If we were a start-up, how would we kill VMware?’”

Iyer’s acute wit and sense of humor were on full display at the VMworld session “CIO Whisperer: How to Successfully Become Your CIO’s Trusted Advisor,” part of a new conference track specifically designed for IT leaders, CIOs, CISOs and CTOs, senior directors, cloud and network architects, and other next-gen IT managers.

CIOs Caught Between a Hammer and an Anvil
In a fireside chat-style panel discussion, Iyer and his co-host for the session, Elan Yanovsky, VMware’s principal solutions strategist, discussed the challenges confronting CIOs in the digital age. Iyer has been in IT for more than 30 years, and the industry has changed dramatically over that time. “There wasn’t even a CIO position or DevOps role when I began,” he told Yanovsky and the packed room.

Now Iyer is the CIO of two companies with two separate sets of priorities. At VMware, he said, the focus is on digital transformation. Dell, however, is in a different phase, focused more on integration and the cultural and operational challenges that brings. This dual perspective on companies deeply invested in business transformation gives Iyer a unique insight into the role that CIOs often find themselves in today: “caught between the business hammer and the technology anvil,” as Yanovsky phrased it.

CEOs often don’t understand what business transformation really requires, Iyer explained. Today’s business needs demand swift technology and operations response that is hard to deliver with existing IT infrastructure. Yet many technologists find it challenging to position themselves as the “technology whisperer” in their CIO’s ear.

In a free-wheeling conversation with Yanovsky, Iyer shared the insights he has gained as a CIO going through precisely this transformation at both VMware and Dell Technologies. Based on his experiences, Iyer believes technologists should not be afraid: CIOs value their input.

Talk Tech Through Business Priorities
Iyer suggested several different strategies to engage CIOs in this conversation. Foremost, he stressed, is to learn how to talk technology in a business context. Start by creating a dialogue based on defining IT’s top three priorities in terms of helping the business achieve its goals. The conversation then naturally evolves into how IT should or could best support these tangible objectives.

Iyer also shared that research demonstrates that an increasingly larger percentage of IT budgets are funded by enterprise business units (BUs). He suggested engaging the dialogue around how best to link the two together (IT and BUs) to budget technology for the right outcome. He then offered cautions to both. To the BUs he warned, “If you ignore IT, you’re going to lose a lot of sales.” And to IT he advised, “Don’t call it ‘shadow IT’—embrace it. Call it business IT.” This, Iyer said, is another strategic way technologists can help their CIOs.

In response to a question from Yanovsky, Iyer said that security provides another great opportunity to discuss IT from a business point of view. He argued that security conversation should shift from the need to invest in security because of regulatory or compliance reasons, to how it brings business value to the enterprise. And if IT wants to see successful security efforts, Iyer added, “Make the most secure way for employees to do something the easiest way for them to do it.”

Tips for Driving Business Transformation
“To help push change, treat your IT team with respect,” Iyer said in response to another audience question. “Look at everyone as a colleague.” And when approaching the CIO with new ideas, “bring data points to help make your case,” he said. He suggests trying what he calls “pretotyping,” essentially prototyping at a micro-scale. Start with small victories, he said in conclusion. Because the “best way to push change is to build your own credibility with your CIO.”