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CDCR’s Retiring CIO, Kristin Montgomery, Offers Reflections on Corrections

“We have a great group of directors and a really strong team,” said Montgomery, the outgoing CIO for the California Department of Corrections and Rehabilitation. “And I think the CIO coming in really needs to learn from them, listen to them.”

Kristin Montgomery sitting at a table at an event participating in a panel discussion.
Kristin Montgomery has been a frequent speaker at tech forums, briefings and conferences, including at the California Public Sector CIO Academy in June 2022.
Theo Douglas/Industry Insider — California
Kristin Montgomery, the award-winning chief information officer for the California Department of Corrections and Rehabilitation (CDCR) since June 2021, announced recently that she’s retiring from state service at the end of this month. She has a career that’s spanned the private and public sectors, and as she prepares to move on, she offered Industry Insider — California some insights into her challenges, her achievements and her plans. Montgomery was featured in an Industry Insider One-on-One interview in August 2022.

(This interview has been edited light for brevity and style.)

Kristin Montgomery.
Kristin Montgomery
Industry Insider — California: Do you have any overall reflections on your career, and state service specifically, as you look back? What are your own personal takeaways?

Kristin Montgomery: I had a really a short stint with the state — it was only 10 years, and it was only two agencies. And I was a first at both of these agencies: I was the first comptroller at CalPERS [California Public Employees’ Retirement System], so I thought, “Wow, I got to create the position.” I fixed a lot of things. I came in, did some org changes, did some internal controls, and really was able to fix that within four years and implement a bunch of new things. And then at Corrections, I was the first female CIO. So again, another first. I was just so lucky with the state. It was a really good 10 years. I had done the consulting gig, and I really wanted to own something. And I was with two large organizations, and I had a lot of people under me, and I really needed to take my consulting and really lead people.

IICA: You’ve spent significant periods in both the public sector and the private sector. What would you say the public sector does better than the private sector? And what would you say the strengths are that the private sector brings that the state might learn from?

KM: Let’s first start with private: I think what the public sector can learn is that the private sector has to be nimble. They’re able to move things quickly, because it really is required and they really have to look at the bottom line, make sure that they are profitable, that they can stay in business. To do that, sometimes you have to take some risks. So from that perspective, I think the state could learn from the private sector, “How can we still be compliant but take the necessary risks to move the needle faster?”

And then from the public side to the private side, I think, is the public sector’s dedication and devotion. The people at the state are so devoted to the mission. At CDCR, most of those people have worked there their whole entire career. I talk to them about, “Well, are you going to move?” And they say, “Oh, no, I’ve got to retire from CDCR. It’s my career.” There’s such a devotion to the mission.

IICA: You’ve mentioned previously in various forums that CDCR is unique among agencies because you have to be, basically, reactive. You’re sort of at the mercy of legislation, lawsuits, budget change proposals, that sort of thing. Does that need drive CDCR to become a little bit closer to that private-sector strength of being nimble and having to be reactive and pivot?

KM: Yeah, I think they are, but they still have that bureaucracy around them. I think that’s what I brought into the state positions that I had: I had to teach people that this is what we have to do. And we’re getting really good at it. But it’s hard to be that strategic when the map keeps changing.

IICA: Everybody talks about AI. For CDCR, do you see any game-changers ahead in technology?

KM: I think it’s more about digitalization than it is AI or whatever. And what I’m saying is, we’re converting the paper into technology. Whether it’s applications that we need to build to capture it, it’s the data that we need to capture the classifying data. It’s all around data and making sure that we get rid of the paper; that’s what’s going to happen with CDCR. CDCR can be ready for AI when it comes, but if the data sits on paper, there is no way that CDCR is ever going to get there. And I see more and more, with the retirements of the correctional officers that hated technology, all the new guys are coming in, going, “Where’s the technology? I’m used to having a phone, I’m used to this, I’m used to that.’ So I think that’s what’s going to change with CDCR — I just really think we’re going to really do a lot of automation for our staff, and it’s just going to be easier for them.

I think, really, what’s going to happen with CDCR — and this is something that the secretary and I always cared about — is it’s going to be like a campus: The incarcerated walk around, they are badging into their job, they are badging into education, they go back to their housing, they badge in, they get their food, they have a badge, all the food comes out, everything’s tracked. So the correctional officers have an easier time to be able to provide safety, provide programming, all that kind of thing. The secretary and I have talked about this over and over again.

IICA: At the Member Briefing that you and your team did for us, Deputy Director of IT Operation and Support Richard Gillespie said one of the technological difficulties for CDCR is the physical infrastructure — the foot-thick prison walls that prevent Wi-Fi, for instance. That’s got to be a big workaround for CDCR.

KM: Yeah, it is — but they can get there. With the technology changing, the carriers like T-Mobile and AT&T have come talk to us: “Hey, you can do it with cellular, you don’t have to deal with Wi-Fi.” And you could, with a combination between the Wi-Fi, cellular, whatever, the institution could have that and be able to do things electronically. And that’s not just for the incarcerated, but also for the staff at the institution. So I think CDCR is going to get there in the next five years.

IICA: Does it feel incomplete to be walking away at this point?

KM: Yes, but there are talented people there. I’m handing it off in a good spot, and if they want to keep pushing on this vision and stuff — and it’s really the secretary’s vision — it’s just a matter of the IT people have to implement it. … It was hard in these budget years — you can’t get stuff done. And that’s hard for people like me — the pushers — and you don’t have the money and you’ve got to be frugal and you’ve got to cut positions and you’ve got to cut budgets.

IICA: Is there anything that you would see going forward that CDCR can do to avoid the pitfalls like lawsuits and BCPs?

KM: You know, I think they just need to be proactive, so that they don’t get sued. The world is changing. … In the private and public sectors, the lawsuits kill us. So if we could really be proactive with that, and if we could just really understand, with the friends and family of the incarcerated, what is going on out there that we need to kind of listen to, so that we aren’t reactive to stuff? Because if they’re not happy, they’re going to go to the Legislature. … I think if we can just stop the lawsuits, and having to deal with that, I think it would be a better thing. The regulation and all that kind of stuff. I don’t know that we can do much with that, because somebody wants something done, and we’re just going to have to react to that. I think every state agency has to do that. So I don’t see that changing, but in particular to CDCR, that’s what I would love to see, those lawsuits being closed and no new ones.

IICA: Do you have any advice for whoever your successor may be?

KM: In these tight budget years, I think they really need to be creative with how we need to keep moving forward. So if the vision is, let’s say, Wi-Fi at the institutions, then really digitize everything. What can we do in an inexpensive way while we’re in tight budget years?

And then, my biggest thing, and I’ve always had this, is you have to have a great team. Use that team, encourage the team. There’s a great group of people there; they are great leaders, they are good team members, and they are very creative. So listen to them, and leave it at that. We have a great group of directors and a really strong team. And I think the CIO coming in really needs to learn from them, listen to them.

IICA: What are your plans in terms of retirement?

KM: I’ll probably get to work part time, probably do some consulting and that type of thing. And I’m going to be traveling a lot. I have grandchildren that do not live in the state. The future’s bright. That’s all I can say. There’s a lot of opportunities out there for someone like me, and I’m not just going to sit around and fish. It’s hard for me to say I’m retiring, because my mindset is not retired.

IICA: Do you feel good about what you’ve been able to do and what you’ve been able to bring to the position?

KM: Yes, I do. CDCR was the best thing I could have ever done, for my career. I got so much support from the secretary, the undersecretary, the team. I had a great time; I had fun. I had the support of everyone from the Governor’s Office all the way to the 700 employees that I had. It was such a fun experience. I just would like to thank CDCR for, you know, pushing me to do this. Everyone supported me, and I just really appreciate all that they did.
Dennis Noone is Executive Editor of Industry Insider. He is a career journalist, having worked at small-town newspapers and major metropolitan dailies including USA Today in Washington, D.C.