Yes, and…

Gwyneth Connell’s passion for improv comedy is no joke.


Last year, following an extensive nationwide search, Gwyneth Connell was selected to lead Pomfret’s Grauer Family Institute for Excellence and Innovation in Education. Established in 2014, the institute is a place where thinking differently is celebrated and new ideas are nurtured. Through progressive program design, technological advancement, and strategic partnerships, Grauer is both a mechanism for mission-alignment and a catalyst for future growth.

In his formal announcement to the Pomfret community, Head of School Tim Richards offered this glowing endorsement of the new director: “Gwyneth emerged from a very deep and talented pool of candidates from across the country. During her two days on campus, she impressed us with her intellect, her enthusiasm, her sense of humor, and her passion for education. We feel strongly that Gwyneth will be the perfect leader as we launch into Chapter Two of the Grauer Institute at Pomfret.”

With more than eighteen years experience as a teacher and administrator working in independent schools, Connell was indeed an impressive candidate. A Peddie School alumna. Degrees from Amherst and Columbia. Teaching stints at Millbrook and Packer. Leadership roles at Berkshire and Blair.

In person, she was just as impressive. During her campus visit, she exuded a sense of warmth and approachability that was matched by a keen intellect and strong vision. “In meetings, in the dining hall, in the classroom, she had a way of bringing out the best in people,” one faculty member commented.

And so, it was no surprise that amid all the formal pronouncements extolling her professional experience and academic expertise, one tiny but important detail slipped through the cracks. “Being funny is something I take very seriously,” she says. 

Connell fell in love with improv comedy as an undergraduate at Amherst College. The simple act of standing up on a stage where anything and everything could happen both thrilled and terrified her. “Improv was brutally hard for me at first, and I was very clearly NOT good for awhile. The process of getting good at improv turned out to be the process of learning to reach outward at the very moment when everything inside me wanted to curl into a ball and hide.” 

In 2006, Connell moved to New York City to study private school leadership at Columbia’s Teachers College. It was around this time that she also started performing with Chemistry Grad School, a troupe comprised of people she knew from the People’s Improv Theater (PIT). “That was a really formative period of time in my life,” she says. “I realized that many of the tools and tricks I was using as an improv comedian could be applied to my work in education. So much so that I ended up writing my master’s thesis about the Yes, and… Rule.”

The golden rule of improv comedy, the Yes, and... Rule requires performers to accept what other performers have stated without question (the “yes") and then work to expand on that line of thinking (the “and”) — no matter how absurd the proposition. “Rather than immediately shooting down an idea that might seem far-fetched,” she says, “it forces you to engage with it.” 

In general, Connell has noticed that people tend to approach open-ended conversations with a lot of preconceived notions. By delaying judgement, she argues, “you give the conversation time to grow and evolve in ways that can be incredibly productive.”

Though only a few months into her new job, Connell’s penchant for building on the good work of others is already yielding results. At the moment, she is partnering with classroom teachers to implement something called the Wellington Engagement Index, a revolutionary new way to measure student engagement at Pomfret. 

Pioneered by the Wellington School in Ohio, the online assessment asks students only two questions: “How much do you enjoy this class?” and “How challenging is it for you?” Students answer with the click of a button, and their responses are plotted on an X-Y axis that falls into one of four quadrants: bored, entertained, grind, or engaged. “It allows teachers to gauge how the class is feeling and adjust accordingly,” she says. “In other words, it teaches them to improvise.”

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Gwyneth Connell

Gwyneth Connell’s passion for improv comedy is no joke.

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