Bill Howlett was the kind of administrator who knew students’ names and interests, waited in the wings to shake hands with every senior after graduation, and never missed a prom.
Howlett, who had been assistant principal at Stillwater Area High School since 2005, died Sunday at St. Therese hospice at St. Odilia in Shoreview. He was 50 years old and had been diagnosed with Stage IV prostate cancer in August 2014.

Howlett had a knack for connecting with students, especially those on the fringe, said Aaron Drevlow, also an assistant principal at Stillwater.
“What he really enjoyed was working with kids one-on-one,” Drevlow said. “He had an affinity for snowmobiling and hunting and working on trucks — he was a big Chevy guy — so he would have an ‘in’ with kids who shared those things with him. … Those would be the kids that he would take under his wing and work with and build relationships with that would keep them in school and see them through to graduation.”
When one known troublemaker was sent to Howlett’s office, secretary Shelly Enhelder expected Howlett to read him the riot act. Instead, the young man walked out with a doughnut.
“I was, like, ‘What? You gave him a doughnut?’” Enhelder said. “And he said, ‘I knew you’d be mad at me.’ I wanted him to throw the book at him, and he said, ‘Shelly, he doesn’t have a dad.’
“I always complained that he was never in his office because he was all around the school,” said Enhelder, who grew up with Howlett. “He wanted to help everybody. It didn’t matter how big the piles of papers were on his desk; he always took the time to talk, always, even with staff.”
Howlett, who lived in Shoreview, was diagnosed with cancer shortly after Rob Bach became principal at Stillwater.
“He always reminded me of what was important, and that’s why it was fun,” Bach said. “The relationship that he had with students was more important to him than just about any other aspect of his work.”
LASTING IMPRESSION
Bach said he ran into a Stillwater graduate at a Woodbury restaurant a few years ago and asked whom she remembered most from high school.
“She answered ‘Mr. Howlett,’” he said. “She said, ‘I spent a lot of time in Mr. Howlett’s office,’ and we kind of chuckled at that because usually there is some underlying meaning if you’re spending a lot of time in the assistant principal’s office.
“The fact that she remembered him, and he was the first person who came to her mind, and that he didn’t conjure up negative images or impressions … just kind of speaks to what he brought to the job,” he said. “How many kids would list an assistant principal as the person that they remembered and that had an impact and influence on them?”
In an October 2015 interview with the Pony Express, the high school’s newspaper, Howlett said he enjoyed dealing with difficult situations.
“Even the parts that get messy, you know, whether that’s kid behavior, or a parent getting upset … my favorite thing is to take those situations and turn them into positive stuff,” he said.
Howlett grew up in Shoreview and Circle Pines and graduated in 1984 from Centennial High School, where he played hockey. In 1989, he graduated from St. Cloud State University with a bachelor’s in education. He later received a master’s in education and a principal’s licensure certificate from St. Mary’s University of Minnesota.
NEVER MISSED PROM
He met his wife, Donna Janovsky, while waiting in the checkout line at St. Cloud State’s bookstore in 1988.
“I had an internship in South Dakota that winter, and in the spring after I came back, he continued to ask me out,” Donna Howlett said. “I finally caved in in May; he proposed five months later. He told one of his friends: ‘That’s the kind of girl you bring home to Mom.’ ”
The couple, who have two sons, married in June 1990.
Before joining the Stillwater district, Bill Howlett was the dean of students at Spring Lake Park High School for four years. He also worked at Centennial High School in Circle Pines and Benilde-St. Margaret’s in St. Louis Park.
While serving as junior-class adviser at Benilde-St. Margaret’s, Howlett started a tradition that continued until 2015. He and Donna would attend prom, dressed in color-coordinated outfits.
“It sort of became our date night,” Donna Howlett said. “We really loved volunteering for prom each year. It was a fun time for us to see the kids get dressed in their finest and behave at their best.”
Although Howlett was on medical leave during the 2014-15 school year, the couple made it to prom that spring. Side effects from chemotherapy prevented him from attending last year, she said.
Howlett was a “hands-on” father who coached his sons’ basketball and soccer teams as they were growing up, she said. William IV, 19, is a freshman at North Dakota State University in Fargo, and Benjamin, 14, is an eighth-grader at Chippewa Middle School.
“He really wanted it to be fun,” Donna Howlett said. “You see some coaches, and they are mean and want to win. He was all about making it fun.”
A few weeks after Howlett entered hospice on Nov. 21, more than 100 friends, students and colleagues met outside his room to sing Christmas carols. The group held signs that read “We love you, Bill” and “We miss you, Mr. Howlett.”
In an interview with KARE-TV about the surprise caroling party, Howlett said his students and staff “give me as much life and as much love as I give them. It’s pretty cool.”
A celebration of Howlett’s life will be 2 p.m. Jan. 16 at Eagle Brook Church in Lino Lakes.