Dennis W. Roseleip: Big Hopes for a Small Town

by Jay P. Goldman
Not long after Dennis Roseleip received a superintendency appointment in his native state of Montana, the district's entire administrative team departed, leaving him to fill three principalships in the opening months of his new post.

The sudden vacancies weren't a statement on the choice of Roseleip, then 44, to lead the Cut Bank Public Schools in Glacier County, Mont. One elementary principal retired, another left for a superintendency. The high school job was the one he vacated. So Roseleip used the rare opportunity to rebuild the administrative team from scratch to show off the true colors of his leadership style and to separate himself from the autocratic decision-making approach of his predecessor.

"I put together interview teams to fill each one because I wanted input from teachers at the various levels," says Roseleip, who previously served a 17-year run as a high school principal in Cut Bank and Sunburst, Mont. But it's Roseleip's earlier training and experiences as a counselor that shape his facilitative and participatory style of managing.

"I've learned as much from observing how to not do some things," he concedes. "My view is … not to make things more complicated than they are, keep everyone informed, be a good listener. … And most important, I've observed the need to exercise emotional control and how the lack of emotional control can result in crash and burn."

Michael Koepke, the school board chair, applauds the superintendent's pro-active efforts, bolstered by his success as a grants writer, to bring the latest technology tools into the classroom and to provide summer and afterschool support for the high percentage of at-risk pupils, many of them Native Americans.

But Koepke says what has truly distinguished Roseleip's leadership is his shrewd recognition that it will take a new form of professional relationship today to attract the best young educators to such distant outposts as Cut Bank. The district, which is located an hour east of Glacier National Park in north-central Montana, has seen its enrollment plummet 15 percent to 858 students over the 10 years of Roseleip's superintendency. Fifty-six of those departures came within the past year.

The school district recently lost all four of its math teachers, who averaged more than 30 years of experience, to retirement, meaning Roseleip has needed to sharpen his recruitment skills against an uncertain economic climate. The district can pay just half of employees' health insurance premiums today after previously footing virtually the full cost, so the superintendent has tried to sell the best candidates on the teamwork emphasis in Cut Bank and the chance to immediately exercise their newfound knowledge in a progressive school system and family-friendly community of 3,300 residents. This fall, seven new teachers, all single and most starting their professional careers, joined the school system.

Roseleip's collaborative nature carries over to his work on several significant economic development projects with city and county government, including the construction of a railroad overpass to allow safe travel between north and south Cut Bank and the refurbishing of the local tennis courts. "He's always been more of a team player than at least his two predecessors," says LeAnne Kavanagh, who has been the editor of the weekly Cut Bank Pioneer Press since 1983.

Says Roseleip: "A superintendent should help educate the staff on the idea that even within a declining enrollment, there are positive things to look at. … The idea of the little red schoolhouse is coming back."

He carries big hopes for the future of his small community and the rest of his state, having recently completed a term as president of the Montana Association of School Superintendents. Roseleip has started an education foundation in Cut Bank as an alternative funding source to support local school initiatives that the declining tax base would not permit. While the foundation is still far from its $10 million goal, Roseleip has received assurances from an alumnus whose estate planning will provide nearly $2 million. Organizers hope another $1 million will be raised for the foundation's Legacy for Learning program at an all-class reunion next summer that could draw up to 3,500 Cut Bank alumni.

"He's always looking toward the future," said Koepke, the school board chair. Adds former board member Scott Gage: "He's instrumental in [ensuring] kids have every opportunity they can here."

Jay Goldman is the editor of The School Administrator. E-mail:

Bio Stats:

Dennis Roseleip

superintendent, Cut Bank, Mont.

high school principal, Cut Bank and Sunburst, Mont.


Greatest Influence on Career:
My counseling background and my strong interest in personal psychology. I have always had a strong desire to be sure that children have a fighting chance to grow up.

Best Professional Day:
Any day when the district appears to be running smoothly, the highest number of teachers is on task teaching kids and our budgets are sufficient to accomplish our goals.

Books at Bedside:
The Purpose-Driven Life by Rick Warren; Authentic Leadership by Bill George; Management of the Absurd by Richard Farson; Who Moved My Cheese? by Spencer Johnson; Hope for Each Day by Billy Graham; Breaking Free When You’re Feeling Trapped by Frank Freed; and the Bible.

Biggest Blooper:
As a young administrator I shared a not-so-flattering assessment of the senior class with a colleague while not realizing the school intercom microphone was on.

A Reason Why I'm an AASA Member:
This professional organization promotes career growth and provides resources that help me function better in my job. The legislative updates, liability protection, state and leadership opportunities and motivating national conferences are all good reasons to belong.