Taylor Stockdale: A Few Minutes with The Head of The Webb Schools

Taylor Stockdale, Head of School

Taylor Stockdale
Head of School, The Webb Schools

Having been appointed head of The Webb Schools (Claremont, CA, view profile), Taylor Stockdale is in the special position of being a twenty-four year veteran of Webb- as teacher an administrator- prior to his appointment.

Stockdale follows Webb’s iconic former head Susan Nelson with whom he worked closely during her tenure.

He talks with us about following Nelson and, being that rarest of hires, the internal candidate for head.

Brian Fisher (BF): Let’s get to the question everyone seems to want to know first, what’s it like to replace a legendary head like Susan Nelson who was almost synonymous with The Webb Schools? If memory serves you and Susan arrived the same year, or, just a year apart?

Taylor Stockdale (TS): I knew going into this that I would have some huge shoes to fill. Susan and I arrived at Webb on the same day in the same year in 1988. I was 25 at the time, and was coming from Rumsey Hall School (CT). I was still relatively new to the teaching field and was hired at Webb to teach history, economics, coach, and serve as a dorm parent. Susan was hired as head of Vivian Webb.

Soon into my tenure in that first year, I quickly identified Susan as a mentor – someone who stood out for her drive and determination, her leadership qualities and her inner strength. After several years in our respective positions, Susan was promoted to Head of Schools. Soon after the announcement, I came to her to let her know that I was most likely going to be leaving Webb the following year to pursue some opportunities on the east coast. One of those “do you have a minute” chats became a 2 hour conversation about our respective educational philosophies, and the possibilities at Webb with the right leadership and direction. Based on that conversation, I decided to stay at Webb and have never looked back.

Susan has been a life-long mentor to me, and gave me some wonderful opportunities at Webb over the years in preparation for my current role. We remain very close, and I draw on her influence every day as I go about my work in advancing Webb into the future.

Taylor Stockdale with Webb students

BF: It’s rare these days for a head to hired from within a school. It seems that many boards want to ‘bring in new blood’ when looking for a new head. With a year in the head’s seat under your belt, what have you found to be advantages and/or challenges to your long Webb tenure and familiarity with school?

TS: Yes, it is rare these days. While it used to be the norm, it is now common for boards and school communities to want to look to the outside or a new leader. I actually believe that in most cases, this is the better way to go. It gives school communities an opportunity to take a fresh look at the future, and to bring in someone without pre-existing ideas for how things should be done, and pre-existing relationships as well. But I think that each head search is unique, and that at times it does make sense to consider an internal candidate.

I think that my institutional history can be a real asset in my work in developing our priorities for the next 5-10 years. At the same time, I need to catch myself when I hear my lips utter phrases like “Oh, we tried that in the 90s and it didn’t work…” I think internal heads need to have a commitment in their own minds to being “new.” To being “fresh.” No one wants to work around someone who’s all about preserving the past at all costs. The internal head needs to use her/his background only as a context, and be wiling to look boldly into the future with a fresh set of eyes. And finally, I think it is vital that if an internal candidate is in the mix for consideration, that there be a full and professional selection process no matter how strong that candidate happens to be. Our board hired an outside consultant to assist them with the search, and this person collected resumes from all over the country at the outset of the process. They then interviewed me thoroughly, and staged an all-school town hall where everyone (parents, alumni, faculty) were invited to ask questions. They weighed my candidacy with other possible candidates for the position and eventually made the appointment. This thorough vetting process has been critical to my first few years in the role.

BF: You’ve had great success as fundraiser for Webb; fundraising is certainly crucial to the school’s future. Beyond fundraising, what challenges do see ahead for the school and how are you preparing the school for them?

TS: Well, it’s true. Fundraising is my passion. I love it. I have also benefitted from my tenure as Assistant Head at Webb leading up to this position. In this role, I oversaw the day to day operations of the school including hiring a top notch boarding school faculty, as well as the curriculum, afternoon, advisory and residential programs.

I think the central challenge moving forward is, as a boarding school which prides itself on personal attention and human interaction, how do we ensure we are relevant – and seen by prospective families as being relevant – in the years to come? What is the value proposition for boarding school with the advent of online communications? And how do we develop an educational experience which delivers the higher level skills and habits of mind necessary to be leaders in a global economy?

When I was in boarding school (way back in the day) in Connecticut, it was all about isolation, seclusion, and being protected from the outside world. Moving forward, I think the most relevant education for high school students will be all about access, connection, and engagement with a global community. For Webb, sitting on the front porch of the greater Los Angeles area and on the Pacific Rim, we are now engaged in a strategic plan process which seeks to take full advantage of our location and, in this way, redefine and reimagine the value proposition for a boarding school experience. It’s so exciting to turn the prism a bit, and to begin to envision Webb’s potential as an optimal boarding school community in the next 5-10-20-50 years.

BF: We’ve gotten this far, and haven’t touched on Webb students. You began your boarding school career in classic triple threat fashion as a teacher, dorm parent, and coach. Do your early experiences in these rolls continue informing and shaping your thinking as school head?

TS: I think so. My heart is always with the kids. I also have a pretty good sense of what the faculty is experiencing in their very demanding roles as educators at a boarding school. At Webb, over the past 5-6 years, we’ve raised the stakes in pretty much every aspect of a faculty member’s job here. To be an advisor now means much more than it did before. Same for being a coach, a dorm parent, even when on weekend duty. And the classroom instruction has changed and is requiring more preparation. As many teachers are now embarking on “flipped” classroom methods and more creative teaching practices, and collaborative lessons, this too is taking more time. So I am also mindful of striking the right balance so that what we are doing is sustainable from a faculty standpoint. Overall, I do think my experiences in the classic triple threat model have been very helpful in allowing me to connect the dots, and in maintaining a vigorous yet manageable pace on the campus.

Taylor Stockdale, 1991

BF: Do you do anything specific to make sure that you stay connected to Webb students?

TS: My wife Anne and I have begun a new tradition of having every students to our house for dinner in the month of September. They come in groups of 50 or so, and we have a blast playing trivia games, lawn games, etc. I certainly get my fill of pasta by the time October comes around. I make a special effort to get to know the freshmen, and to also spend time with the seniors through chapel talks, etc.

Students at The Webb Schools

BF: Since becoming head, tell us a story about something that you’d never thought you’d see, or do, that surprised you and made you laugh?

I think that it’s the range of work on any given day that has made the biggest impression on me. One minute you are helping a faculty member resolve an issue, another you are talking to a board member on the phone about a policy matter, and then another, you are talking to a student about the student newspaper, and then another, talking to a parent. It’s the variety of topics that constantly require you to change hats, to listen well, and to be as helpful as possible in sorting things out when needed.

Learn about The Webb Schools!

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Brian Fisher

A product of both private and public education, Brian Fisher served as a teacher, coach, dorm parent, and administrator at three different boarding schools. Brian also fills the role of Director of Development at Wolfeboro, The Summer Boarding School, in NH along with being a partner at AdmissionsQuest.

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