The Puzzle: Blog

Celeste Herrera is Assistant Head of School at The Dalton School in New York City.

1. What is your current title and which school or organization are you from?

I am the Assistant Head of School at The Dalton School in New York City.

2. What was your first job in education? What are the major steps you’ve taken since then?

My first job in education was in college admissions. I worked for the University of Pennsylvania as an admissions officer, traveling to a specific territory and speaking to students and families, reading applications, and ultimately being part of the decision-making process to admit students to Penn. From that I made a shift that is somewhat common in the world of admissions and college counseling, I became a Director of College Counseling at a high school in California. I enjoyed that period in particular because it was a newly established school and I was one of their founding college counselors. Then I received the opportunity to work at Dalton, initially in the college counseling office, gaining exposure to a more established and differently sized institution. At Dalton I’ve moved up progressively in responsibility, from Associate Director of College Counseling to Director of College Counseling, then to High School Director and now to Assistant Head of School.

3. What is something you learned about yourself through your current role and/or the leadership positions you have held?

What I’ve learned about myself is that I love bringing people together to work on complex issues or big, thorny projects that push independent schools forward. I’m interested in what’s next for independent schools and consistently am a voice for progress, for self-reflection, for centering students and faculty as citizens of a community versus defining achievement as our primary goal. I’ve learned to center that about myself, that I’m focused on students being reflective and educators encouraging that reflection, encouraging an awareness of self and others, and encouraging a sense of mutual responsibility.

4. Where do you look for inspiration, support, and advice? Perhaps a specific person, group of people, author, thought leader, or community?

I’m fortunate to have many mentors and they span a number of roles. I have several who are deans or directors of admissions at the college level. I love to think about that transition from independent school to higher education and how we’re well-preparing students. I also have mentors who are lifelong educators in independent schools, teachers and administrators, several heads of school who have graciously taken their time to support me. People who are connected to progressive education, those who work in the online and digital education space, and those who are looking at alternative modes of transcription and assessment; I have a good number of folks in that arena as well. I’m not afraid to write an email or pick up the phone. I think part of what is important is to use the network within your current school to network around it. I can reach out to a colleague and say, “Hey, do you know anyone at this school? Could you put us in touch?” I love to go out and visit. I’m conscious of my privilege there, as we have the resources to send folks out to travel, to go and do campus tours. I’ve met a lot of folks through asking if I can spend a day learning about their program or getting to know their role. I feel very strongly about returning that graciousness and capacity, so that if anyone wants to come hang out at Dalton and learn how we do things or what my work is, I’ve met a lot of people that way too!

5. What is the best career advice you have received? From whom?

The best career advice I’ve received is to center what I value, what brings me motivation and drive. For me, that’s working at these complex institutions to build communities that are reflective and generous of spirit. I return to that often, particularly in a pressurized world where achievement, return on investment, and how we define what success looks like in education is getting more transactional. I’m motivated to surround myself with people who are focused on citizenship and improving the people we send into the world in that regard, and to not redefine what I value.

6. On your best days at work, what are you doing? What aspects of your job bring your particular joy?

On my best days at school I’m solving problems or building programs. I love building, expanding, innovating, and helping teams come together to improve our already very strong academic program. Or, I’m the person you call when something goes off the rails and you need someone to mediate, to make a decision, to manage a crisis candidly. I enjoy that work as well as the more forward-thinking opportunities that we have to really grow and support our kids.

7. As educators, we are always learning and growing. What is something you’ve recently learned or are working to learn?

The next step for personal growth for me is going to be connecting with educators who want to think about the lessons we learned during the pandemic and how some of them were a positive shift in education. I’m very focused on the idea of learning as connected to a physical place. What about a school community at school is really important to hold on to? What did we learn about how students can grow and learn outside of a classroom environment? I’ll be doing a lot more work with experiential education, global partnerships, and really thinking about how students will best retain information that will prepare them for a workplace that’s evolving so quickly. That’s where a lot of my reading, education, and networking will focus.

8. What advice would you share with those aspiring to leadership? What advice would you give your younger self?

There’s no one path. I am a less traditional candidate than some to be in an assistant head of school role, having come from college admissions and moved through my school accordingly. So, center your gifts and talents and make sure that those are made clear even if you have not necessarily come from a traditional path of administrative leadership. The second piece of advice I have is to consider ways in which your school community can help you grow. Often we’re givers in education and we think about what we’re providing to our workplace, but think too about what resources and expertise you can glean from those who work around you. Never be afraid to ask the question, to get yourself more information, more education, more professional development, or more growth. A piece of advice I’d give to my younger self is, as you grow more administratively, make sure to maintain consistent connection with the students, particularly if you come out of the classroom experience. That can be hard as you’re pulled into more external facing roles. It certainly has been the case for me and so as I shifted in my career to the Assistant Head role, I’m really thinking about how to stay consistently connected with the kids. Younger self should have kept that centered a bit more.

9. Tell us about an item in your bag, in your office, or on your kitchen counter that captures the essence of who you are. (Silly or serious, as you wish!)

I’ll go with silly! My office wallpaper! It’s called “alien abduction toile.” It looks very traditional – like a normal French pattern – but it isn’t. There are little UFOs and aliens, if you look closely you can see them taking up the humans. If you see my resume or you’re reading a bio, you’ll think, “OK, she’s traditional, she worked for Penn, she works for a fancy independent school,” but that’s certainly not what I value and I often surprise people with my take and circumstances. I change my office wallpaper once a year, it’s peel-and-stick! In a world where it felt like everything was topsy-turvy, I went with an alien abduction theme!

10. Is there anything else you want to share?

Where I feel a lightness of being is knowing that groups will come together for this Women’s* Institute. We’ve been insular and in our corners for way too long and I am hopeful as a result of this experience and meeting new people in this capacity for even more growth and connection. This feels like a period of great possibility, which is exciting!

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