Deaning is Just Hard: Some Advice
Moira Kelly talks with Bridget Johnson and David Torcoletti
Bridget Johnson is the founder of the Deans' Roundtable, the community for Deans of Students. She is a former Dean of Students at Milton Academy, is a coach to Deans, and a consultant to schools on student life issues. She developed the Student Life Assessment Tool, which is now available to help schools assess the quality of their student life programs.
David Torcoletti is a senior consultant at EXPLO Elevate. He is a former Dean of Students and School Dean at Northfield Mount Hermon School, as well as Dean of Students at Milton Academy. He has coached early career and experienced Deans and consults with schools on student life.
Bridget and David first met when Bridget was new to deaning and David was her coach.
Moira Kelly (MK) – Welcome, folks. Great to see you both. I feel like I am with kindred spirits since we’ve all sat in the dean's hot seat. It’s a tough job. I know time is tight today, so I’m just going to jump right into the questions. The first one is a two-parter. When you think about people being new to deaning, what advice would you give them? And then second, when you're helping them do their work, what does it mean to think like a dean?
Bridget Johnson (BJ) – The first piece of advice I would give is not to try to do this by yourself. I know you're in charge as the Dean of Students, but don't feel like you need to make decisions alone. Make sure you're consulting with others and bouncing ideas off people. Know who your support network is. Have your team of people.
MK – Who are your people?
BJ – Other leaders at the school. Get a mentor. Get a coach. It's like concentric circles. You have people immediately around you—the assistant dean in your office who reports to you directly—those folks should be part of your team and the decision-making process. Then there are people you meet with regularly.
Beyond your school, you should have mentors or colleagues you can call on to say, "Does this sound right to you? We're wrestling with this issue, and I need perspective." You might not have that network initially, but you need to develop it. Find those colleagues who are doing similar work because they're likely experiencing many of the same challenges.
Sometimes you also need to discuss certain aspects with family and friends—not to vent, but to help them understand what your job entails. Do this respectfully without sharing confidential details. When people get a sense of what you're dealing with, they'll better understand when you need space or support.
Regarding thinking like a dean, it's similar to how we help students "think like a historian" in history classes. You have to balance community needs with individual concerns. You need to follow the rules stated in your handbook consistently, and if you find yourself deviating, that's a sign you may need to revise your handbook. That's fundamental to thinking like a dean. You want to ensure each student is treated as an individual whose voice is heard, while simultaneously considering how decisions affect the entire community.
MK – David, I'm going to ask you the same thing. Advice to people new to deaning, and then what does it mean to think like a dean?
David Torcoletti (DT) – I think that Bridget just gave excellent advice. I think part of it is, how do you hold yourself in place, to keep you from blowing all around? And part of how you hold yourself in place is that you allow other people to hold you in place. And she named all of them, colleagues, people who do the same work but are outside of your school, and to the degree that it's ethical, with your family and friends. I think that being able to be held in place while the maelstrom is going on outside of you is really important.
I think discernment and courage would be the other things I would say are important. When you're looking at a situation, you need to be able to evaluate it and say, this is this, not that. It looks a little like that, but it's not. It has its own individual structure to it. It has its own little detail that keeps you from putting it into a category and just acting as if it's the same as other things that belong there. So you need that kind of fine discernment to truly know what it is you're actually looking at, who that person actually is, and how the situation actually affects the community. That level of fine discernment is really important, and it doesn't come right away. You have to understand that you're going to screw that up because you haven’t yet developed that level of insight, judgement and wisdom. But wanting to - wanting to see what you really have in front of you, is important.
“Everybody thinks they have a reason for being unhappy with you, and most of them will take it. That's just the way people are. People want to blame. We just do. And you're probably the most eligible player for blaming on the entire campus.”
You have to exercise courage because you can't make everybody happy. Someday, your colleagues will think you were too weak on something that needed to be really heavy. The next day, the students will think you were way too heavy on something upon which you should have been more moderate. Parents will always be unhappy if their individual child has consequences, and they'll be unhappy if the other children don’t have enough, that you somehow didn’t punish another child enough. Everybody thinks they have a reason for being unhappy with you, and most of them will take it. That's just the way people are. People want to blame. We just do. And you're probably the most eligible player for blaming on the entire campus. Courage is not being fearless. I never mean that by courage. What I mean by courage, is that you're afraid, you're anxious, you're nervous, you're dreading something, and somehow you do what’s right – you do the hard thing. If you do that again and again, it becomes a habit. Because you don't die, 99.9% of the time. You're not actually cast out. We almost always exaggerate the consequences of being brave. And so if you just hang in there and act with courage, you realize that you survived that one, and it becomes easier the next time.
MK – What does it mean to think like a dean?
DT – I mentioned discernment. It’s like you're a good doctor. Like Dr. House on that TV show. I love that show. You're looking at all these possibilities, and the illness might be this, and it might be that, and it's probably not lupus. They'll always say it's lupus. You have to ask a lot of questions. Why won't this faculty member do this? Why is it that the staff member who lives on that floor can't create conditions so that the students get to have a study hall that's at least halfway decent? What is it about them, the way they think, feel and interact with others? I have to look at that staff member and realize, well maybe they're new to boarding school life and inexperienced. Or maybe they're a people pleaser. And because they're a people pleaser, they have a hard time accepting it when a student curses them under their breath and so on. So I have to figure out why isn't this happening? That kind of diagnostician approach, I think that's a mindset you don't start with, but you have to develop to be successful.
BJ – I want to add one thing: I think being curious is extremely important. Don't assume you know what has happened on face value, because 9.99999 times out of 10. You don't know the full story, and I have definitely gotten bitten.
DT – And I think curiosity is a wonderful trait. What a good word for what a dean needs to be - that's what a good diagnostician needs to be. Being curious about the unfurling of the stories.
MK – Okay, so the next question is, you folks have worked as coaches to folks who are walking along the dean path. What are the challenges along this path that are just part and parcel of doing this job?
BJ – One of the things is putting your ego aside and not making it about you. Whenever someone's coming and yelling in your office at you, or students are mad about the decision you made, we can take it personally. We want to do a good job, right? And so we have to remember it's not about us. It's about doing the thing and creating a safe community for students and a safe community for adults alike because we're doing this work for everyone. We're not just Deans of Students. We're more than that. In my opinion, it's the Dean of Everybody. It feels like that a lot of times, and so you definitely have to put all of that aside and think about the greater good. I'm going to stop there and let David jump in.
“One of the things is putting your ego aside and not making it about you. Whenever someone's coming and yelling in your office at you, or students are mad about the decision you made, we can take it personally. We want to do a good job, right? And so we have to remember it's not about us.”
DT – I like the idea that one of the challenges is your own ego. I think that's true. I think the other thing to know is that, on the other hand, a lot of it is about you in terms of how your responses to a situation probably comes somewhere out of your makeup and your personal history. Your past may cause you to get particularly irritated by bullies, - bullies are a thing for you, and maybe it's because you were bullied. Or you were a bully. Your parents had a certain approach that felt like bullying, or something like that. And so knowing yourself and knowing that you tend to respond very strongly to these situations is important. Maybe you are a bit more laissez-faire about some other campus issue, and somebody else might find that issue the cardinal sin of humanity. And the one that triggers you isn't that big of a deal to them. So, knowing it's not about you ultimately, but you are the tool you use to get your job done. So you better know what you're made of, and what the kind of things that trigger you, the kind of things that relax you, knowing just who you are while you try to do your job selflessly, is one of those contradictions that you can't avoid. Yeah, know thyself. I definitely say that to new deans.
MK — Bridget, you mentioned that being a Dean of Students is really being more than that—you're the "Dean of Everybody." As an aside, years ago, I remember walking through Boston with David, and he saw a group of unknown high schoolers doing things they shouldn't be doing. He felt compelled to intervene, as if he were the Dean of the World.
BJ — Yes, I experienced the same thing. Especially after I stopped being a dean, when I moved to New York, I'd see situations on the train where I wanted to step in, or I'd have to consciously stop myself from picking up trash on the street—it was just habit. These behaviors become ingrained in you, and it's really difficult to turn that off. It took me quite a while to adjust.
As a dean, you end up managing many different people, even when you don't directly supervise them. Whether it's working with student activities, campus safety, food service, or overseeing the health center, you're guiding adults who interact with students. You need to ensure everyone is being even-handed and help them understand why that consistency matters. It gets complicated, especially when managing people who don't report directly to you but still need guidance or occasional correction. You sometimes have to say, "You actually can't do that," which can be challenging, particularly when you're managing people who are senior to you in age.
MK — At some schools, deans are on the senior leadership team, and at others, they are not. What can an excellent Dean of Students bring to the senior leadership team that is important and might be something that no one else on that team is bringing to the table?
BJ — Well, you're boots on the ground with the students. If the leadership is considering programmatic or structural changes to the school or developing an emergency plan, your perspective is essential. You might need to point out that "Taking attendance that way won't work because students are dispersed during that time," or "Actually, no one's around during that period." If you don't understand the schedule intimately, or how students move around campus or what motivates them, you're making decisions in a vacuum. And that's what often happens when the Dean of Students isn't present. The leadership makes decisions, presents them, and they simply won't work in practice. The senior leadership team often includes the people least connected to students' daily experiences, which is precisely why you need to have a Dean of Students in the room.
DT – Amen. Yeah, I think it's really difficult. I think for the same reasons. Your last question, which I'm still sort of rolling around in my head, is that when you're the Dean of Everything, what does that mean? And what does that mean when schools hire people to do the work of an institution? It is rare that schools hire most teachers and staff because of their expertise in working with children outside the classroom. Generally, faculty are being hired because they teach biology, and they can also coach hockey, too. That's usually why someone gets hired. And somebody who doesn't display much expertise (or even interest) in working with kids can get hired anyway because you need subject area experts. Then you place them in a dormitory, and we give them some quick training, but not nearly as much as they got in biology. To teach biology, they were educated for years. Most were not given much training on how to work with kids, other than by living the life of a kid.
“So you're conducting an orchestra, and maybe less than half know how to play their instrument, and that's a tough job.”
So, I guess what I'm saying is as the Dean, you are not, for the most part, working with trained people who are doing the work of your office. Instead, many of the people who do the work of your office are not trained in student life work, and do not prioritize the student life part of the job. Some are dedicated and wondrous. This is the part of the job they love the most. And while that does happen, I bet that's less than 50% of the staff, and depending on the school, maybe less than 20%. So you're conducting an orchestra, and maybe less than half know how to play their instrument, and that's a tough job for the conductor.
The same thing is true of your school’s senior leadership team. Most of them aren't hired for their expertise of working with children. Some were once teachers, but the rest were not. So what do you do with the person who's dealing with development, or the person who's dealing with finance, or admissions? It’s essential that they're there. They are incredibly important to the team, but they can't represent the student point of view. You have to. I think leadership teams that do not have the Dean of Students aboard are flying without instruments, and it is a mistake.
MK – Thank you both for this. It’s so helpful to hear from folks who have been in the trenches.
DT – It was fun.
BJ – Yes. Thanks. Have a good one Moira. David, we’ll chat about the conference this summer.