Hall Cheshire, chief information officer. Photo by Norm Shafer.

When Hall Cheshire graduated from high school in the 1970s, he set his sights on becoming a jazz guitarist. Though he still dabbles in music today, back then he received some sage advice from his father that made him realize his talents lay in other areas.

“He said, ‘This computer thing seems to be catching on, so maybe you should get into that,’” said Cheshire, who now has over three decades of experience in IT. A desire to work for an organization with a mission he believes in led Cheshire to become the chief information officer for the University of Mary Washington, where he manages not only technology, but also the projects, people and budgets that come with it.

One of his team’s biggest assignments to date – affecting all areas of the University – is migrating faculty and staff emails and SharePoint sites to Office 365. It’s an enormous undertaking, but Cheshire said that most UMW departments have already successfully adopted the new system, and he expects the project to be completed by the end of the year.

“I’m fortunate to work with very smart and talented people in the IT department,” said Cheshire. “My team did a lot of research and testing to prepare for the project. Thanks to their efforts, everything is going smoothly.”

Q: There are lots of bells and whistles with the new system. What’s your favorite?
A: Of all of the applications in the Office 365 ecosystem, I use Planner the most. It’s a basic project management tool that is great for organizing, assigning and managing tasks.

Q: People get possessive about their email and are often resistant to change. What kinds of reactions did you encounter during the migration?
A: Most people just want to know they won’t lose access to their email. We’ve migrated hundreds of email accounts over the past year, and the majority have gone off without a hitch.

Q: What’s the most rewarding part of your profession?
A: Solving problems and adding value. Information technology is an important part of most processes at UMW, and it’s great to be able to contribute to the University’s mission.

Q: What’s the most challenging?
A: Someone once told me that any problem can be solved with enough time, money and people. Unfortunately, I rarely have enough of any of those. It’s a constant challenge to do what needs to be done with limited resources.

Q: What would people be surprised to learn about you?
A: When I was in my 20s, I earned a black belt in a Korean martial art called Hapkido. I haven’t practiced it in decades, but it was a great experience.

Q: What’s your favorite thing in your office?
A: Years ago, I took a watercolor painting class. The only picture I painted that was not a complete disaster is on my desk. It’s a reminder to me that I can occasionally be creative.