Each Thursday night during the school year, 16 girls come together for an hour to participate in the Chaffee Leadership Institute, a program in its eighth year.  

“We say this every year,” said Dean of Students Mike Donegan, one of the faculty leaders, “but wow, this year, this group is truly amazing. They are good together and good with each other, and I think the whole group is being raised up by this level of [critical] thinking.”  

“We do this whole food for thought,” Mike starts to say and turns to his co-leader, Michaela Chipman, the coordinator of sexual wellness, an English teacher, and a dorm head. “What’s an example of food for thought?” They have a rapport that is not unlike the one they are trying to instill in the girls each year. 

“Think of someone in the Loomis Chaffee community you have always looked up to and admired and write them a note,” Michaela said. “Ask to talk with them and then share how it went.”  

The program is funded by the Chaffee ’69 Leadership Fund, established by members of the Chaffee Class of 1969 on the occasion of their 50th Reunion in 2019. The fund honors the Chaffee School name and supports the leadership institute and its annual programs, which are designed to educate and empower female students in the skills of leadership. 

Students wishing to join must complete an application. Michaela said the girls take the application process seriously, as do Michaela and Mike. “What I find remarkable is their commitment,” Michaela said. “They’re not getting a grade, but it is a priority for them — and for us.” 

“I have had the most wonderful experience in CLI,” said sophomore Blair Sontag, referring to the Chaffee Leadership Institute by its frequently used acronym. “Not only has it allowed me to meet and work with girls outside of my own social bubble, but it has given me friendship among driven young leaders. I have enjoyed learning the specifics of being a leader, especially being a leader as a young woman today. ...  CLI is a space where I am never afraid to speak my mind or share my thoughts. No one is ever shamed for what they think, and we are constantly building each other up.” 

During the COVID-19 pandemic some Chaffee graduates participated in a Zoom call with students in the program. A connection was developed. “Afterward, we said, ‘This is what it’s all about,’” Mike said. 

A bridge to the past also was evident another time. Several recent alumni, who had participated in the institute and were then seniors in college, were talking remotely with current students in the program.  Those college seniors were about six years out of the CLI program. “They’re saying, ‘Let me tell you what I remember, why it was good for me, and this is what I am doing now,’” Mike said. 

And then, said Mike, three of the alumnae “broke out, unsolicited, their journals that we gave them. … Three of the four had their journals, and one says, ‘There’s a quote I want to read to you.’ I mean, I got little tearful.” 

“Me, too,” Michaela said.  

The program has a weekly agenda — among the topics are mentorship, values, finding your character strengths. There are guest speakers. But, as Mike said, they could into the meeting with no agenda and easily fill an hour talking. 

“I went into CLI with hopes of broadening my education on leadership in a supportive environment, but I have found that and so much more,” sophomore Tomorrow Chestnut said. “CLI has been a sisterhood and has showed me the immense value in women-only spaces. I’ve learned to express myself with more confidence, how to go about improving myself to improve my community, and of course I’ve [encountered] girls with different opinions and girls with different passions. I love CLI, and think it is a very valuable experience here at Loomis.” 

When the year ends, Michaela said, she wants the students to know that they are highly capable of being leaders in their final two years at Loomis and beyond. “However,” she said, “they should expand their definition of leadership. They should approach leadership as an active practice, rather than just a title.” 

Mike said he wants the girls to know “that their voice matters, even in the small things, and beyond that, they are stronger together. There is nothing they can’t do or change.” 

When junior Norah Pond reflects on her experience in the program last year, she says it was an opportunity “to learn more about the world, my peers at Loomis, and, most importantly, myself.” 

Each year the students end with a capstone project. Norah and two others went to St. Gabriel's School in Windsor and did programming with girls in grades 1–3 about such things as leadership, teamwork, and confidence.   

“My capstone also forced me to fully commit to a project and see it through from start to finish, which is something I had struggled with in the past,” Norah said. “Being able to create a project that I truly cared about and working on it for months showed me that I was capable of achieving anything that I truly set my mind to, and that mindset shift is something that I will take with me for the rest of my life.”   

Norah also took away some smaller — but important — lessons. 

“Some of the little things we learned were the things that stuck with me most,” Norah said. “Seemingly miniscule skills such as making eye contact or deleting phrases like ‘if not, that's OK’ from my emails have completely changed how I view myself and how others view me.” 

Senior Sydney Hallowell said CLI taught her how to be a confident leader, not just a leader. “CLI is a great way to get involved on campus, and it truly helps if you’re interested in becoming a leader on campus in later years,” said Sydney, who this year is a resident assistant in Howe Hall, a PRISM president, and a Peer Support Network mentor.