Leading with Love: Lessons Learned from My First Year in Administration

First years at anything are hard. Kindergartners learn how to do school for the first time; middle and high schoolers learn how to navigate change not only in academics and moving from self-contained classrooms to several new courses/teachers, but also in social groups and the physical signs of adolescence; college freshmen are learning to live on their own—or as the common parlance is today, “to adult.” First-year teachers are managing the overwhelm of planning, teaching, collaborating, assessing—all the while trying to remember what sleep and a social life are. And first-year administrators are moving from the ground-level to 10,000 feet, seeing their schools from wider vantage points while enduring a baptism-by-fire of new responsibilities, systems, protocols, and ways of being. It’s exhausting.

Before becoming an administrator, I taught for 17 years in public and independent school classrooms. I thought I’d never leave. I thrived from curriculum development and from learning new pedagogies and approaches to classroom teaching. I was energized from the daily interactions with students and how no day was ever boring. I enjoyed watching students grow up during their time in high school, and I marveled at who students had become as they moved through the early years of adulthood. There was joy in my work every day.

At the end of each course I taught, I would offer these parting words to my students: “May you be blessed to do what you love.” And each day I taught, I felt blessed to do what I loved.

And yet, there came a time when I realized that no matter how much I kept learning and enjoying my work, I thrived from working with teachers as much as working with students. I wanted to be in a role that served adults so they could best serve their students. As Dean of Faculty, I have found a way to still feel blessed to do what I love each day.

I’m coming into the final months of my first year as an administrator, and I imagined the work would be much different from teaching. In fact, it is, but so much of what I do has its foundations in classroom practice. While I certainly have a tremendous journey in store, I’ve learned some lessons that have made the vicissitudes of this work manageable, and the road ahead more exciting than daunting.

Whether one is finishing up the first year of classroom teaching, contemplating administration, or asking what’s next, these lessons hopefully serve a purpose that transcends the boundaries of our current roles in our school sites.

Communicate with Intention

We are flooded with information throughout our work days, and often times, we are quick to pass people in the hall asking for a few minutes of their time or firing off an email that allows us to knock an item off the to-do list. I certainly have been quick to ask a teacher to check in at the end of the day, and I also have been the recipient of the “Can we talk about something?” email without knowing the context. Those seemingly benign words and moments can create all kinds of fear and anxiety, which is not helpful for anyone.

I do my best now to begin my communications with my intentions, naming up front what the need or core topic is, and then asking for a few minutes to talk or check in. Regardless of the recipient—whether a parent, colleague, student, or school leader—it’s a courtesy to be up front about one’s intentions, as it reduces fear, mitigates anxiety, and ideally, allows more trust to build among all stakeholders.

Plan Difficult Conversations as Carefully as Your Lessons

The first lesson dovetails into this second one. Oftentimes, intentional communications are about difficult conversations, and while conflict is scary, no one benefits from topics that everyone is afraid to discuss.

Coming into this job role, I was most afraid of the hard conversations, because I feared I would do great damage in this arena: I would hurt others, and in turn, I wouldn’t be liked or respected—thus damaging any relationship I had with my colleagues and those I served. However, I have learned the hard conversations are the most essential to the work we do in schools, and we should plan and attend to them accordingly.

In advance of any difficult conversation, I ask myself (and often write down) the following questions:

What is the core need here? Why are we having this conversation?
What are my intentions in having this conversation? What do I hope the outcome is?
What is my relationship to this person? How can I tend to this relationship and ensure I’m meeting the person where they are rather than where I am?
What information do I still need? What do I need to ask in order to hear the other person’s experience?
What are the hard things that need to be said? Where might we meet in the middle?
While the conversations themselves are never easy, and while the outcomes are not always rosy, the planning allows me to be deliberate about my approach and make these conversations a collaboration rather than a conflagration.

Be Mindful and Slow It Down

Before my new role began, I made a wish list of all I hoped to accomplish my first year. When sharing some ideas with my colleague (thinking I was being proactive in my goals), my colleague responded, “I remember making that list.” And then he laughed. That moment was humbling.

We live in a society that moves fast, where gratification is increasingly more instant. And yet there are movements that counteract that speed, movements that force us to slow down, pay attention, and be present to our work—and mindfulness is chief among those movements.

Whether responding to a tricky situation or planning a long-term project, nothing has to be accomplished in nanoseconds. If anything, stopping to take a breath (or ten) and slowing down a process with intention allows opportunities for feedback, revision, and ultimately, a better outcome. I still keep my running list of ideas, but now I do so as an exercise instead of as an expectation—allowing me to stay creative while also staying grounded.

Be Transparent When Possible

If there is any lesson that translates directly from classroom practice to administration, it is the value of transparency. Just as we share our objectives with our students, the same should be the case with those we serve. Our classroom spaces are bastions of transparency, whether through the agreements we create, the expectations for assignments, or the rubrics for our assessments. In each case, we are transparent about what we desire and how we will get to our objective. While classroom spaces also are places for discovery, we hold our environments together by the systems and routines that allow our students to feel safe. I have benefited from sharing my goals, expectations, feedback mechanisms, and systems with teachers as much as I did when I was in the classroom, and transparency, like intentionality, helps to foster more trust in relationships and in the school as a whole.

Improvise and be Your Own Entrepreneur

The greatest misnomer about administration is that we all have it dialed in, that the myriad of books and workshops on leadership have allowed us to be ready-mades who enter into the workplace with confidence and skill. In my experience, though, being a first-year administrator is like being a parent to a newly adopted rescue pet: you have a general sense of the work ahead, but you have no clear idea of how this work will play out; you have to be responsive to each situation as it arises.

I certainly have felt supported in the work I’ve done, but a lot of times, too, I have had to carve my own path and create a system and workflow that works best for me. Innovation isn’t just a 21st Century classroom skill; it’s a way of life for an administrator as well. Whether determining the best way to schedule a day full of meetings or devising a protocol for classroom visits and goal-setting, or carving out space for my own growth and learning, I have learned that regardless of the systems I have inherited, I need to make them my own in order to do my best work—and serve others well.

Lead with Love

This final lesson is the loftiest indeed, and it is the most foundational to my first year. Truth be told, I thought I’d hate the first year in this role. I thought I’d miss the classroom so much that six months in, I’d be pitching in my towel and going back to what I loved most. However, the opposite has proved to be true. While each day certainly hasn’t been easy, and while there are days where I want to call it, I find that I love the work just as much as teaching. I serve students at a distance now, but I serve their teachers with the same care and attention I devoted to the classroom. Each relationship in our school is important, and in order to nurture students, we have to tend to everyone in our building. Just as our students want to be seen, heard, valued, loved, our adults do, too, and it is an honor to do that work in service of education.

I still have a few more months left of this year, and I have a long way forward in this profession, but leading with intentionality, deliberateness, mindfulness, transparency, innovation, and love have made the journey worthwhile so far.

Lori Cohen: Lori Cohen is the Dean of Faculty at the Bay School of San Francisco. Prior to her current position, Lori taught Humanities, Literature, and Religion/Philosophy at Bay for many years. Lori also coordinates Teacher Development seminars, in-house professional development, for Bay faculty and has begun a Teaching Fellows program that will be entering its third year. This will be Lori’s fourth year as a co-facilitator/teacher leader in Teaching Foundations, a program that brings her joy and professional rejuvenation.