And there aren't many budding leaders in their wake, creating what Benest called a "tremendous leadership crisis and brain drain.
"In my mind, the talent crisis is the most pressing challenge facing the city because we cannot do anything without talent," Benest said.
The retirements will be disruptive at a time the city is stretching to achieve even more with a limited budget, Benest said.
Benest has warned of the crisis before but it now is imminent, he indicated.
The topic is a particular passion of Benest's, who has published and lectured extensively on the issue. Councilman Yiaway Yeh said he even studied Benest's work while in graduate school at Harvard University.
Under Benest's leadership, the city has developed a three-part program to address what he calls the "next-generation challenge."
First, the city has implemented several programs to identify and train future leaders, including conducting leadership forums, allowing staff members to serve in an exchange program with other communities and teaching and encouraging managers how to talk to employees about career goals, Human Resources Manager Heather Shupe told the council.
It is also trying to retain its institutional knowledge by interviewing departing staff members, publishing a retiree newsletter and creating an online wiki called "Palopedia," which staff members can use to document their knowledge about the city's operations, Accounting Manager Trudy Eikenberry added.
The city is also trying to attract young professionals, Benest said.
Young people care about the social issues and "saving the world," but they turn to nonprofits, not government, for employment, Benest said.
Many young adults view government as "bureaucratic, mind-numbing, mindless," Benest said.
"How do we get them to see they can achieve their values and have a good career" with local government? Benest asked.
Baby Boomers, like Benest, who is a few years shy of 60, were drawn to public service in the John F. Kennedy era, he said.
"I did not for a second consider joining the private sector. How boring; how inconsequential," Benest said.
To attract young adults, the city has developed an internship program for undergraduate and graduate students, hosts an annual job-shadowing day for high school students and provides a fellowship program for recent graduates, Recreation Supervisor Cash Alaee said.
Benest briefly brainstormed with the council the city's positive and negative qualities as an employer and displayed the results of a similar brainstorming session with top managers.
The results were strikingly consistent.
Palo Alto has cutting-edge programs, such as its climate initiatives; great weather; strong management; regional and national leadership; an engaged community. It offers advancement opportunities; competitive pay and great benefits. It is not too large and not too small. And it is adjacent to Stanford University.
But housing costs are prohibitively expensive, leading to lengthy commutes from as far as the Central Valley; the community is "hypercritical"; and the media negative. The council is larger than most; the city has extensive rules and processes; staff members have to attend evening meetings; city facilities are aging and the regional private and nonprofit sectors offer lucrative positions.
Recent or near retirees include Community Services Director Richard James; Regional Water Quality Control Plant Manager Bill Miks; Michael Jackson of the Public Works Department; Administrative Services Director Carl Yeats; Real Estate Manager Bill Fellman; and Police Technical Services Manager Sheryl Contois.
With a rare public display of wry humor, Benest added himself to the list, saying he has spent "eight glorious years with the City of Palo Alto."