Charting a New Course for Chestertown: A Chat witth New Town Manager Larry DiRe

Like many with plans for a chosen career path that takes a left turn, Chestertown Town Manager Larry DiRe thought his MA in History from Loyola was a pathway to an academic life of teaching.

However, the job market was not signaling an abundance of need for history majors, and DiRe altered his course by accepting a job as a proposal and grant writer for an engineering company in Chicago and beginning his new path in town management. 

Turns out, his love for history paired well with his interest in town management. 

Once, visiting the ruins of a town outside of Budapest, DiRe intuitively configured the layout: the market’s location, the area best to build a water plant, and the probable location of public toilets. Town planning became a lens he looked through wherever he was.

Now, four months into his role as Chestertown Town Manager, Larry DiRe says he views Chestertown through that same lens but, for the immediate future, wants to take a deep dive into the town charter, understand the codes expressed there, and make sure the community knows he and the town council have an open-door policy.

“How do we collaborate? And, you know, what are the channels by which people are heard? You know, how do we take feedback? Are we always good at listening? And, and, you know, some of those criticisms, “well, the town (management) doesn’t always listen.” I’ve made it a point of it, you know, at least in the introductory period here.”

That said, DiRe points out that service to the community needs to be balanced with organizational evaluations and updates like code reviews.

“There’s always, I think, a premium put on the community side of it and sometimes not a premium put on the organizational side. And I think the organization needs some things refreshed,” he says.

The Spy recently met with Larry DiRe to discuss his first four months in a wide-ranging interview about his background and his new role in Chestertown, implementing policies and directives established by the town’s elected officials while managing the town’s budget and personnel.

This interview is approximately fifteen minutes in length.