Portsmouth High Principal Robert Littlefield retires

Delayed announcement because he wanted to focus ‘on ending the school year the right way’

Jim McGaw
Posted 6/30/16

PORTSMOUTH — Whether cheering on members of the football team or mixing it up with students in a Project Purple Week dodgeball game, Principal Robert Littlefield was a constant presence at …

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Portsmouth High Principal Robert Littlefield retires

Delayed announcement because he wanted to focus ‘on ending the school year the right way’

Posted

PORTSMOUTH — Whether cheering on members of the football team or mixing it up with students in a Project Purple Week dodgeball game, Principal Robert Littlefield was a constant presence at Portsmouth High School even at nighttime and weekend functions.

“That’s what good principals do,” Mr. Littlefield said Thursday. “That’s what my role models did and they set great examples for me. I never did count the hours, although I did go over my calendar; I was at 38 evening or weekend events over the school year. My family has been terrific, but they’ve made sacrifices for me.”

You’ll no longer see him around the school, however, as Mr. Littlefield abruptly retired this week after 18 years on the job. Wednesday was his last day in office. 

The news seemed to catch other faculty members and school officials off guard. On Thursday Terri Cortvriend, chairwoman of the School Committee, which now must find a new principal for PHS, said she first heard of Mr. Littlefield’s leaving just two days ago.

“He just decided to move on. I don’t know if he has another opportunity,” said Ms. Cortvriend. ‘I wish him the best in his future endeavors. He did a lot for Portsmouth High School.”

Although he didn’t inform faculty members he was leaving until Monday, Mr. Littlefield said he decided to retire in April, when a team of educators from the New England Association of Schools and Colleges (NEASC) were at PHS to conduct an accreditation review, a process that takes place every 10 years. The NEASC team had lots of good things to say about the school, said Mr. Littlefield, who decided it was the ideal time to leave the district.

“I’ve worked hard for 18 years to get the school to where it is and really, I just keep thinking to that day in April, at the end of the NEASC visit,” he said. “I said to myself, ‘You’ve done a really good job to bring this faculty to the point where it is. Is it ever going to get any better than this?’”

Mr. Littlefield said it was a conscious decision to delay his retirement announcement until after the school year had ended.

“There’s a lot of important work a principal has to do in order to close out a school year and get people focused on the next,” he said. “I didn’t want to be looked at as a lame duck; I wanted to be looked at as someone who was still the leader of this school. And, I wanted to focus on the kids and focus on ending the school year the right way. I didn’t want the focus to be on me.”

Did he regret not saying goodbye to his students?

“I did have one boy who came to visit me yesterday and that meant a lot. He really wanted to come in and see me and wish me well. If I were the kind of principal that wanted the focus on me and not the kids, then yes, I’d regret that,” he said.

Mr. Littlefield grew up in Rockland, Mass. and taught for 18 years in Norwood, Mass. before taking an assistant principal’s position in South Kingstown. He still lives there with his wife, Maureen. (He has two sons, Tim and Adam.) Five years later, in 1998, he was appointed principal of PHS.

‘Lot less combative’

When asked how his approach to his job evolved over the years, Mr. Littlefield said he learned that cultivating relationships with students, parents and faculty is mandatory for a school to be at its best.

“I’ve worked hard to foster those kinds of relationships not only with teachers, but with staff, students and their family and the community,” Mr. Littlefield said. “If a principal is going to be successful, they have to know who you are and they have to know that you’re always going to listen. That’s why I’ve tried to do.

“Certainly, I learned a long time ago that you didn’t have to win every conversation. It was OK to give somebody the opportunity to express themselves and agree to disagree to move on. I think I was a lot less combative in the latter half of my principalship than i was in the beginning.”

If something bad did happen at the high school — such as a student getting caught dealing drugs — Mr. Littlefield had a reputation for sharing it with parents, rather that sweeping it under the rug. He said his move toward transparency started about eight years ago, when he made a pledge to a group of mothers who came to visit him.

“They really made the plea that if they’re going to do their jobs as parents, they needed to be able to talk to their kids and to do that, they needed to know what was going on,” said Mr. Littlefield. “I didn’t try to hide anything. Sometimes you open yourself to criticism to the community when you hang your dirty laundry, but I felt it was a lot more important to the families of the kids to let them know what was going on.”

He’s also proud of the connections he’s made with students over the years. One student let the principal know he made a difference during graduation this year, Mr. Littlefield said.

“There was one young man who came to us in a bad way and he and I forged a relationship and I was able to, because of my position as principal, really do some good for the young man. On graduation night he expressed his gratitude to me and that’s going to stay with me for a long while,” he said.

He’ll also miss the many faculty members he’s worked with over the years, most notably his administrative assistant, Diana White.

“No one means more to me than Diana White. We’ve worked side by side for 18 years, tackling everything that came down the pike together. This is going to be an adjustment for both of us.”

Future is wide open

Although he’s leaving the Portsmouth school system behind, Mr. Littlefield, 63, is keeping the door open to future employment opportunities. 

“Everybody keeps telling me that I’m going to have great opportunities and people would be willing to capitalize on my experience and record. I’ve had some conversations, but nothing that I clearly speak to right now,” he said.

As for his immediate plans?

“I’ve got to sort through all the boxes that are sitting in my basement,” he said. “Then my wife and I are going to take a couple of weeks off in July and spend quality time at the beach and play some golf. And then we’ll see where the path leads me.”

Portsmouth High School, Bob Littlefield, Robert Littlefield

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