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State Tech Leaders Offer Takeaways on Guiding IT Work

There’s more than one right way to accomplish major technology work but sometimes, tough decisions have to be made for the project to move forward, officials at the California departments of Technology, Motor Vehicles, and Corrections and Rehabilitation said recently at the California Public Sector CIO Academy.

From left, Kristin Montgomery, director of enterprise information systems at the California Department of Corrections and Rehabilitation; David Cross, vice president, enterprise sales, Comcast Business west division; Ajay Gupta, chief digital transformation officer at the California Department of Motor Vehicles; and Russ Nichols, deputy state CIO and California Department of Technology chief deputy director, discuss “Owning Your Own Journey” at the California Public Sector CIO Academy.
Theo Douglas/Industry Insider — California
The path to IT success is rarely straight and flat, state technology leaders said earlier this month at the first in-person California Public Sector CIO Academy since 2020; and, to a very great extent, staffers and teams must find their own way there.

In a frank discussion of “Owning Your Own Journey,” Kristin Montgomery, director of enterprise information systems at the California Department of Corrections and Rehabilitation; and Ajay Gupta, chief digital transformation officer at the California Department of Motor Vehicles, shared perspective from their own roles with the state and offered ideas for making initiatives happen. The panel was co-moderated by Brenda Bridges Cruz, deputy director of the Office of Professional Development in the California Department of Technology (CDT); and Russ Nichols, deputy state CIO and CDT chief deputy director. It also featured David Cross, vice president for enterprise sales with Comcast Business west division. Among the takeaways:

  • There’s no “cookbook” for an IT project or for leading one as a CIO, Nichols said, telling the room that many times, “especially in the state, what happens is in the CIO role, you have so many people pulling at your coattails and telling you which way to go.” Whether that means advice from a “control agency,” the California Department of Finance or your department’s own chief financial officer, it can feel paralyzing. “You’ve got to own that journey — and own it means for the good and for the bad. Sometimes you’ve got to operate outside your positional authority,” he said. “‘Well, it’s really not my call to make.’ But what bad thing happens if you do? Take the risk. Sometimes it’s worth the risk.” And, if something doesn’t go to plan: “Own it. Be willing to stand up in front of your boss, in front of the Legislature, in front of somebody else, and say ‘You know what? That did not work out the way I intended.’ OK. Might cost you your job but you’ve still got your integrity and frankly, I’d still hire you.”
  • Montgomery, who helped guide CDCR through the modernization of its Strategic Offender Management System in a time period when Nichols was its CIO, said officials and staff must maintain a close relationship. A culture of trust and open communication are key when people are asked to step outside their roles or job descriptions, she said, emphasizing: “You have to be able to talk to anybody about the good, the bad and the ugly.” Another vital piece is seeking ideas from your team — and delegating tasks to your staffers. “Giving people an outcome,” she said. “There are so many ways that you can go with any kind of project. And I think that’s the biggest thing that I try to instill with my team ... is, ‘Look, I’ll tell you what I’m looking for, I’ll give you the vision. How you get there, there’s many different ways, and own your mistakes, own your journey, you can do this.’”
  • Gupta, who has helped DMV automate and take its processes online since joining the department in 2019, said capacity is crucial to allow for experimentation and to foster innovation. At Google, he said, 20 to 30 percent of staff time may be left unplanned with the expectation that it will be needed for research. That’s difficult and potentially costly in state government but it can be accomplished, he said, by giving staff the right tools and the space to do the work; by removing “some of the work that’s needed to do critical thinking”; and by instilling a sense of purpose. “And in the case of the DMV, we care about our customers and that customer-centricity, always thinking about the customer has become very paramount. It’s a constant message that we drive to the staff,” he said. “Creating awareness — creating awareness about what needs to change and what needs to improve.” So, too, is the drive — the motivation, and “some tolerance for failure. ... But you want to make sure you calculate that failure, meaning you start small and then you go big, which means if you fail small, you learn from it and then you go big, learning from that,” Gupta said.
Theo Douglas is Assistant Managing Editor of Industry Insider — California.