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Classroom Technology

From Data Security to Digital Literacy: The 5 Toughest Tasks for One CTO

By Alyson Klein — June 11, 2019 7 min read
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Rob Dickson, the executive director for information-management services for the Omaha public schools in Nebraska, has spent this school year fending off dozens of cyberattacks, managing a shift to cloud computing, and worrying about both teachers, who’ve come to technology late in life, and students, who can’t seem to get off social media.

Like it was for many ed-tech leaders across the country, the 2018-19 school year was a challenging one for Dickson, and the year ahead could be even more so. Looking back, Dickson, who has been in Omaha for five years and is headed to Wichita, Kansas, next school year, says there were five especially big challenges he faced this year, and tackling them provides important lessons learned for other school district technology leaders. Here’s a look at those five:

1. Building Digital Literacy Among Teachers and Students


What’s the biggest digital-literacy challenge for staff members?

“We have the largest workforce gap that we’ve ever had. People don’t retire like they used to,” Dickson said. “You’ve got generations of folks that are coming into technology at such a late cycle in life, and due to that, there’s a skills gap.”

Dickson has three daughters, one is still in high school and two have graduated, and he feels their exposure to technology in school has been very inconsistent, depending largely on the expertise and interests of their teachers. “I look at their experience with technology and I don’t want that to be circumstantial anymore,” he said. “I want them all to have the same chances to be able to utilize technology and to expand their learning with technology.”

What about the biggest digital-literacy challenges for students?

There’s a real range there. “Some kids live in poverty, and their experience with devices may be just a cellphone, and they may not have internet access at home. As a district, we try to make sure that we level the playing field,” he said. What’s more, Omaha’s students—and just about everyone else their age—spend an “exorbitant amount of time on social media.” He wonders what effect that has on them and on society.

Omaha’s solution: Leaning in on “digital citizenship.” In fact, the district has a full-time staffer devoted to digital citizenship, who helps schools implement a curriculum designed by Common Sense Media, a nonprofit that advocates better use of digital media in schools. The goal: help students learn about cyberbullying, what’s appropriate to post online and what’s not, and even how much screen time is good for you. Over the past five years, 80 of the district’s 96 schools and programs have been recognized by Common Sense for their work in this area.

The district has given out more than 30,000 devices over the past two years and has plans to allocate another 26,000 next year. But schools have to embrace the Common Sense curriculum before they can begin using the new devices.

“We make sure we lead out with that prior to devices being accessible to kids,” Dickson said. “That’s how we’ve kinda dangled that carrot to drive the change to happen.”

2. Data Security: A Constant Concern


That’s a huge topic. What specifically are you worried about?

It’s just a constant concern for a district like Omaha, Dickson said “This year, we’ve had more targeted attacks than we’ve ever had,” he pointed out. “Every month, there’s a good 40 or 50 types of attacks that we get from phishing attempts to malware. But since I’ve been in the district, we haven’t had any type of outbreak.”

Part of the solution: Consistent vigilance. Omaha uses a cloud app (Cloud App Security) from Microsoft. And Dickson and his team do monthly security checks. A third party comes in once a year and does a security assessment.

“It’s really about having consistency of reviewing. It’s a question of what processes do we have, how do we change those processes, and how do we move forward,” Dickson said. “We’re constantly adopting things,” including programs to allow for more collaboration in the classroom. But with any collaborative program, like a new online curriculum, “you have to take a look at what the weakness are.”

One example: Omaha just adopted a digital curriculum and worked to make sure that it automatically “rostered” each class with the teachers and students that are listed in the district’s student-information system.

That makes life more efficient for teachers, who don’t have to spend time adding their entire class list to the system. But it’s also great from a security standpoint, Dickson said, because the system will automatically update if a teacher or student leaves.

How do you balance strong data security with making sure teachers can innovate?

There’s a formal process for that, Dickson said. The district built an “app approval” tool three years ago. Using materials provided by Common Sense, the district takes a look at privacy protections, legal issues, and more. Once the district’s tech committee makes a decision about a particular app or program, it will post it on a dashboard so all teachers in Omaha know which apps have the greenlight and which don’t.

3. Journey to the Cloud


Can you tell me a bit about how cloud computing is used in your district and how that’s helped or created unintended consequences?

Right now, Omaha is moving its entire district data center to Microsoft’s Azure Cloud Computing platform, Dickson said. There are some big pluses, including easier disaster recovery, backing up data, and the flexibility of not having to buy new hardware, which can be a five-year investment for a district, he said. The district only pays for the storage it uses, and the privacy protections are stronger than on-site.

Still, it requires an organizational shift.

“It’s a challenge because it’s a different way of managing,” Dickson said. “Before, you might have had three or four people managing different resources in a data center, and this is like one person or two people managing an entire cloud infrastructure. So it’s a change in roles and how people work.”

How do you see cloud adoption evolving in the future, and what are the upsides and downsides of it?

“I think it’s only going to happen more and more,” Dickson said. “Districts from a budgetary standpoint need to be efficient, but they also need to be nimble. I don’t see our adoption of programs lessening. I see it only happening more and more as devices become more cost-effective and we deploy them in places that are needed to be able to support learning for students.”

Any downsides to cloud computing?

It’s something that can be easy to get into but tough to get out of, Dickson said. “If you want to change to a different cloud provider or bring it back on the premises, sometimes there’s a large or significant charge for that.” But security is less of a worry. “Cloud security has started to mature as districts migrate their data and solutions there,” Dickson said.

4. Using Analytics to Improve Student Outcomes


Where is Omaha in the use of analytics to make instructional decisions?

It’s a big and growing part of the district’s strategy, Dickson said. “We use them for coaching teachers, for student assessments, even for attendance of staff and students, so every kind of facet that you can think of. I only see that growing,” he said. “Now, it’s just making sure we’re putting data where you need to see it at the time you need to see it and understanding what data a principal needs to see, what data a teacher needs to see, even what data a student needs to see.”

What’s your take on the use of machine learning or algorithms to analyze data?

“If it can present insights for a teacher, that’s great,” Dickson said. “I still want the teacher to make the decisions. Cause really, that teacher owns the learning for those students. But if I can give the teacher insights into what’s happening, that’s perfect.”

5. Being the ‘How’ for Business and Learning


What exactly do you mean by being the “how”?

Technology is integral to everything, but Dickson and his staff have limited bandwidth and expertise.

“Any time you’re doing any type of implementation of anything in the district anymore, it involves technology. The challenge that we have as a department is that you don’t want to own every project just because technology is being used,” Dickson said. “It becomes challenging because we don’t grow in staff much and we end up taking on large projects. Anytime you become the how for everything, it’s just not sustainable.

What are you doing to address that?

“It comes down to project management. It’s identifying those business leaders of that particular project and providing that professional development to really empower them to own it,” Dickson said.

Can you give me an example of what you’re talking about?

Omaha is adapting a school safety solution right now. “From a technology standpoint, I can tell you everything we can do. But I need the safety person to own what we should do. If the project was driven by what we can do, then I don’t know that we’d be meeting the needs of safety.”


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