Ashland loses longtime administrative analyst Diana Shiplet to Portland

In a sad yet hopeful parting, the city of Ashland said good-bye to Administrative Analyst Diana Shiplet on Tuesday.
Shiplet has worked for the city roughly 12.5 years. She began as an executive secretary and over time her position expanded and morphed into what it is today, working closely with the city administrator and mayor, only because she was hungry to take on more.
That same hunger led her to apply for a position with the city of Portland, for which she was accepted. She starts her new job Monday, April 9.
“It was completely unexpected,” Shiplet explained. “I was having a bad day and felt like I needed to take control of my life so I just randomly applied.”
She said filling out the application made her remember what all skills she possesses, and three weeks later she was hired for the job.
“I just needed a change, and I realized that I’m sort of at the top of the ladder in my current position,” Shiplet said. “I just can’t imagine sitting on that step of the ladder for the next 20 years of my life.”
She said in her new position she’s starting “lower down on the ladder” and has the opportunity to expand her knowledge and training to work her way up in a different setting.
The difference will be a fun challenge, Shiplet said. Portland runs by bureaus rather than a strong-mayor form of government like Ashland, Shiplet said.
“There’s 250 employees of the city of Ashland and there’s 6,000 of the city of Portland,” Shiplet said. “It’s a huge change as far as the types of interactions that people have in the city.”
Her new title is executive assistant for the chief administrative officer of the office of finance and management. In this role, she’ll be working directly with Tom Rinehart, the city’s chief administrative officer.
“It will be nice to go from essentially eight bosses … to having one boss,” Shiplet said. “It’s very similar to what I do now, it will just be on a considerably larger scale.”
She was working for the city of Santa Rosa, California, and missed the Rogue Valley she knew from college when she applied to the city of Ashland more than 12 years ago.
Her original role was to aid the mayor, council, and city administrator, but because of circumstances such as retirements and changing positions, her role has shaped into a unique position, Shiplet said. Aside from the daily duties of administration, she’s taken on various jobs such as as piloting the first Team Ashland program.
“I think I learned more about the city and my own job through that than I have through almost anything else,” Shiplet said.
Shiplet said one of the scariest events she experienced at work was the Oak Knoll fire of 2010 which burned 11 homes and led to the death of a firefighter.
“We weren’t hearing everything that was going on … and we were trying to communicate to the community without actually being there,” Shiplet said. “It taught us a lot about emergency preparation and how to communicate amongst ourselves, as well as to the community.”
She said the strangest experience she had was dealing with some nudist citizens who decided to walk in some rather inappropriate places, including around the public schools.
“The strangest thing was probably the summer where we had lots of naked people,” Shiplet said laughing. “Taking those phone calls was odd, to say the least.”
She said she hopes to make the same connections in Portland as she’s made in Ashland and find a similar sense of community.
“The people who work for the city of Ashland … are incredibly talented and incredibly hard-working and I really wish more people in the community recognized that and supported their efforts and skills,” Shiplet said. “Too often they only see the decision made by an elected official and they don’t see the hard work put in by the staff members. My coworkers are the reason I have loved my job for so many years and have stuck around for all of these years.”
“It’s all an adventure,” Shiplet said.
— Contact Ashland freelance writer Caitlin Fowlkes at

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