When Chris Hennessey came to Wiscasset Middle High School at the end of a school day to interview for principal, a kid outside was playing hacky sack. The veteran public school administrator hadn’t seen a kid do that in a long time. The two talked. 

“We were shooting the breeze, and he was so warm and welcoming, (to) this guy in a tie, he doesn't even know … And that was the impression I had (of) that school when I walked in there that day.”

June 9, the school committee named Hennessey WMHS’s next principal. Superintendent of Schools Dr. Kim Andersson told Wiscasset Newspaper, she's excited to welcome Hennessey to the Wiscasset community, "and I look forward to introducing him to the students, staff and town." Hennessey follows Principal Sarah Hubert, who resigned and next school year is interim principal at Greenville Consolidated School. 

Hennessey was still in Vermont June 9 as the school year closes at Lamoille Union Middle School; he has been grades seven and eight principal in the school that, like WMHS, has both middle and high schoolers. That middle school's two grades combined have about the number of students all of WMHS does for grades six through 12, he observed in a phone interview. 

Hennessey said he is a "youthful 60," deeply into community theater performing, from Shakespeare to Chekhov, plays in a senior men's baseball league, but thinks he "might be done with hardball baseball" and is a "gym rat." He shared why he'd been looking to move to Maine's Midcoast, his early thoughts on some of WMHS’s challenges, and an aspect of WMHS he is looking forward to: A small school means he will get to know everyone, the students, their families and the faculty. "That's how I lead ... I'm a relationship-driven guy (and) I really like to get to know all of my kids as soon as I can. And at some of the larger schools I've worked in, that's much more challenging. So it was definitely appealing when I saw that."

What drew him to look for work around here? He explained, he grew up in Massachusetts, "and I'm one of those people who has been visiting (this) region since I was a little boy." He and wife Shannon Lessley have for many years been wanting to move to Midcoast Maine, where daughter Catherine Hennessey works at Glidden Point Oyster Farm and lives in Newcastle, and twin Olivia is also considering moving.

The couple was visiting Catherine in February, "and we just decided, 'What are we waiting for?' So I let my folks here at Lamoille .... know that we were going to be plotting a move. And then this job opened up. 

"And honestly, it's like a dream situation for me. I'd wanted to get back to a middle high school principalship, and just meeting the folks there, it just felt like a really good fit."

The University of Maine journalism graduate has been a principal at the elementary, middle and high school levels, and a superintendent of schools. "So I've got quite a deep set of experience that I'm able to bring to the table ... And I think those years as an elementary principal really, really helped inform me to be a better secondary school leader ... just learning a lot about how young children develop and learn as readers, as mathematicians, as people."

He knows about Wiscasset's test scores, its decline in enrollment, and about the school safety concerns that are being aired about WMHS. "Some of these issues are not unique in any way ... We have declining enrollments all over America, and we're trying to contend with how to deal with that on a financial level." He is not comfortable commenting on test scores yet, since he doesn't know what data's being used, what the assessments are, or how they're administered. As for safety, he said, "yes, I am aware of that situation. 
I am currently working in a grade seven to 12 school ... And what's interesting about it is that we have procedures in place that separate (middle and high schoolers) when it is appropriate to keep them separated, but importantly, we do have them combine communities at various times.

"One example is that we have some of our middle schoolers taking high school classes. We have high schoolers mentoring our middle schoolers. And ... the reason I bring this up is that there are times when we are definitely going to want to have high schoolers connected with our middle school kids. 
What you don't want to have is a situation where, and I don't know this whole situation that happened last month, but where kids aren't where they're supposed to be, right? And that to me is a procedural thing that I'm going to need to work on with the team and see what's going on there. And we'll  be able to figure that out. 
It's just a matter of holding everybody accountable. But it's something I take very, very seriously. I've got a lot of experience working with creating safe school environments, (including) in more urban school districts.

He added, "I think we've got to be careful in not painting the situation with too broad a brush, because there are going to be situations where you want the kids to be together for very, very positive, developmentally appropriate reasons that help both the younger kids and the older kids. 
I've got to get a little bit more information on that, but I guess what the community should know is I take this stuff very seriously, and if we had a sort of a procedural breakdown that occurred in that incident last month, people have a right to be upset. Well, OK, what do we put in place to ensure that that doesn't happen or it's extremely less likely for it to happen? And if it does, how do we address it?

"I've got to get to know the community and I'm looking forward to meeting people. I'm going to do a lot of listening, for sure."

The move to Maine will be gradual, with Lessley keeping her curriculum director job in a Vermont school district and him commuting the three hours and 45 minutes back to Vermont on weekends. They don't plan to sell their home there until they find the right one here. 

"We're going to have a little bit of a vagabond lifestyle for a while, and we knew what we signed up for," he said.