Growing up in Milwaukee’s Park West neighborhood on North 28th and West Clarke streets taught Maudwella Kirkendoll early that expectations can save a life.
His family and friends set high expectations for him, and being with them got him to where he is today.
The long road took him many places, some tragic.
He lost his mother at age 11 and was forced to grow up a little too early.
“It shapes you,” Kirkendoll said of the experience. “You learn to read people. You learn responsibility.”
Today, as the chief operating officer, or COO, of Community Advocates, Kirkendoll oversees one of Milwaukee’s most stable and largest social service organizations. The group’s work includes housing, behavioral health, emergency assistance and partnerships with grassroots groups across the city.
But the foundation of his leadership was built long before he ever heard the phrase social services.
Raised by expectation
According to his sister Nurika Thomas, Kirkendoll has always been a leader.
“He is loyal, passionate and caring,” she said.
As a child, they called him “Dynamite.” The nickname stuck so much that some family members never used his given name.
The name came with expectations. His friends leaned on him for advice and even random facts about math or government. They held him to a standard he sometimes didn’t hold for himself.
“They would skip school and do whatever they did,” he said. “But if they caught me during the school day they’d walk me to the bus stop.”
That role never ended. He still gets calls from old friends who need help with résumés, marriages or job leads. He doesn’t hang out the way he used to, but he always helps, gives advice and listens.
At home, he said, there was church four nights a week.
That mix — street reality and moral expectation — defines his approach to service.
As a case manager, clients respected him because he could say, “I understand.”
He did. He grew up poor, experienced trauma and knows firsthand what instability feels like.
But he believes empathy must be paired with accountability.
“I’ll help you this month,” he’d tell clients. “But what are we going to do so you’re not back here next month?”
That balance comes from his own life. He was given a second chance, he said. He believes others deserve one, too. But they also deserve someone who believes they’re capable of more.
A second chance
Social services were never the goal. He actually didn’t know much about the field before joining it.
As a kid, his only exposure to assistance came from standing in food lines and knowing the building at North 12th and West Vliet streets.
“Food stamps and free cheese,” he said. “That’s all I knew.”
At 16 he enrolled at University of Wisconsin-Milwaukee and failed every class. He was smart but unfocused and getting into trouble.
He said he struggled to navigate between what he knew was right and what was right in front of him.
Then he met the woman who became his wife. She challenged him to lean into his smarts and give school another try.
He enrolled at Milwaukee Area Technical College before transferring to University of Wisconsin-Whitewater.
“He beat the odds,” Thomas said. “I’m very proud that he still reaches back in the community to try to help, and he’s understanding also because he knows the environment and he knows how hard it is.”
He graduated college, began a graduate program in school business management and interned with Milwaukee Public Schools, planning for a career in school administration.
He hated it.
“This is a place where nothing gets done,” he said he remembers thinking. Six months in, he knew he couldn’t stay.
Around the same time, a coordinator position opened at Community Advocates. He took it. It was the only job he ever formally applied for there. Every promotion since, from manager to division director, to COO, he said, came because someone saw something in him.
“I never planned this,” he said. “But I love what I do.”
Relationships over titles
On paper, COO seems like there is some distance from day-to-day realities.
In practice, Kirkendoll starts his days at 7 a.m. answering emails before he no longer has time. By 9 in the morning, he’s checking in with managers and frontline staff.
Community Advocates runs a shelter and several other buildings so he’s wherever he needs to be when a crisis happens. This includes repairs and other general maintenance.
He prefers working with his hands. Roofing, plumbing, windows and anything else he can do with them gives him peace.
So does golf, a sport he once dismissed as “not for me.”
Relationships are most essential
Inside the organization, managers are expected to collaborate because clients rarely arrive with a single issue.
Andi Elliott, CEO of Community Advocates, said Kirkendoll thrives at bringing people and thoughts together.
“If there’s conflict on a team, he brings everybody together and talks it through,” she said. “Strengthening team dynamics rather than creating division.”
Outside the building, Community Advocates quietly supports smaller grassroots groups that lack infrastructure.
“We don’t talk about that work a lot,” Kirkendoll said. “But it matters.”
He is wary of politics. Years in meetings with city and county officials made him skeptical of silos and public alliances that don’t match private conversations. He refuses to “play the game.” It may cost some opportunities, he admits, but he can look at himself in the mirror.
He believes integrity is non-negotiable.
A hand up
Good service to Kirkendoll looks like fully listening, assessing the immediate need, and then digging deeper to address the root cause so the person doesn’t have to return.
“I would love to work ourselves out of business,” he said. “If we can stop young Black and brown people from coming through our doors, that’s success.”
He leads staffers the same way.
In his 26 years at Community Advocates, Kirkendoll said elevating people was his greatest accomplishment.
Many of the organization’s current leaders started as interns, temps or entry-level staff under his supervision. He pulled them up, developed them and positioned them to lead.
“I’m not going to be here forever,” he said. “We’ve set ourselves up for a good transition.”
The serenity prayer guides him: Change what you can, release what you can’t. Focus on the work in front of you.
Sometimes he’s surprised he made it this far. There were moments in his youth when living past 18 didn’t feel guaranteed.
Now he’s 50. He’s thinking about grandchildren. And eventually stepping back so younger leaders can take the reins so he can enjoy his later years instead of working until there’s no time left to enjoy them.
“He is the type of person that is genuine, authentic and makes real connections with everybody he encounters,” Elliott said. “He just quietly does the work, not for accolades or attention, just because that’s who he is and that’s what he believes in.”
Jonathan Aguilar is a visual journalist at Milwaukee Neighborhood News Service who is supported through a partnership between CatchLight Local and Report for America.
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