Last month, I wrote about the qualities the Board of Education should look for when choosing our next superintendent of school.

I semi-jokingly, semi-wishfully said the only candidate who checks every box might be God. Of course, even He or She might find the challenges presented by the closing of Coleytown Middle School — and the type of town this is — to be too overwhelming to sign on the dotted line.

Now it’s time to tackle the other key position we need to fill: principal of Staples High School. This educator also must be God-like, but even that may not do the trick. A high school principal is on the front lines, interacting every day with teenagers and their parents. So perhaps we’re looking for God, plus two others: Job and Solomon.

Staples principals have a long and storied history. The second one ever may have been the most famous, at least outside of Westport. Wilbur Cross was just 22 years old when he was hired by Horace Staples. He left after a year and went on to a distinguished career as an English professor at Yale and then, in his 70s, governor of Connecticut. But he set a high bar in terms of expectations.

Some of Cross’ successors became legendary. The Scotsman Douglas Young ruled with a firm hand as Staples (and Westport) entered the post-war era. Stan Lorenzen oversaw the move from Riverside Avenue to North Avenue, and the beginnings of the shift from the silent 1950s to the go-go 1960s.

Jim Calkins was an accidental principal — a last-minute, interim choice — who combined a deep faith in students with a recognition that the times they were a-changing. He kept a wild, overcrowded school together at a fractious moment in American history.

When other institutions, including high schools around the country, imploded due to issues like war, civil rights, sex and drugs, Staples became a national leader in innovative curriculums and shared decision-making.

John Dodig was another accidental principal. He had retired a few months earlier from Fairfield High School. He came on in October, expecting to stay only through June. He remained at Staples for more than a decade. Like Calkins, his faith in his students was deep and firm, and he spoke about it often. He took a high school that a few years earlier was discontented and demoralized, and — by working with staff, students, parents and the entire community — made it a model of caring, compassion, excitement and excellence.

James D’Amico was just starting to make his own mark, when his alma mater New Fairfield High School hired him away. He leaves behind a school in very good shape, proud and strong.

Each of those principals was very different. Each had his own philosophy and style. What all shared was an understanding of their school, their constituencies, their times, and their own strengths and weaknesses. They did not try to be someone they were not, or to lead in a way that did not suit them well.

The next principal of Staples High School inherits a smoothly running, well-functioning school. The staff is strong; student achievement is high. It could be easy to be satisfied, to take the helm and steer a steady course.

But any good captain knows that rough seas can arise any time. Winds can shift. Calmness under pressure, flexibility, the ability to sense danger, the willingness to take a certain amount of risk — all are key to avoid running aground.

The tailwinds of standardized testing might push Staples — and the new principal — toward the shoals. As the school prioritizes critical thinking and introduces new courses, ways of teaching and assessing, there’s a national push toward more tests.

Will he or she stand up for what works in Westport? And can the new principal communicate those beliefs to students, parents, the Boards of Education and Finance, and college admissions officers?

What about college, in fact? How will Staples react to the changes looming in higher education? What kind of messages do we send students about post-high school plans? How well are we preparing them for the real world?

Those are only a few of the issues the new principal must deal with. Some are concrete and real, like budget. Others are philosophical. Some are disciplinary. Many involve technology, and our love/hate relationship with it.

No matter what the topic — and a principal deals with many at once, like the guy keeping all those plates spinning on “The Ed Sullivan Show” — our new principal must be a master communicator. That, to me, is perhaps the most important qualification of all.

Along with (of course) a love for the town, school, staff, parents, and most especially, Staples students.

Let the best man or woman win.

Dan Woog is a Westport writer, and his “Woog's World” appears each Friday. He can be reached at His personal blog is