After 16 years of teaching, I have taught in two schools and have directly reported to 3 instructional coordinators, 5 principals, and 15 assistant principals. That’s a lot of bosses to serve, and I have learned from each one of them. Sometimes those lessons have been what not to do lessons, but mostly, I have an enormous level of respect for my school chiefs. I’m not "kissing ass"; I’m saying what is true. By and large, I have worked for ethical, hardworking, and lovely people. Deal with it.
At this point in my career, I generally say what I think and do not filter those opinions much, regardless of which job titles are in the room with me. I owe this attribute largely to Vincent Cariello. Recently, Vince retired as Associate Superintendent of Administrative Services for Cecil County Public Schools, but for me, he will always be one of my 3 principals at Elkton High School. Vince’s stint at EHS may have been the shortest time period of any of his varied system roles, but it changed me and how I approach my job for good.
Truthfully, I wasn’t happy about Vince coming to EHS. I had no prejudice against the man himself, mind you, but his arrival occurred in the wake of the departure of my first principal (who had hired me and mentored me as a new teacher) for a job at the board office. I psychologically relied on her presence a great deal and felt that loss acutely. All of the reconnaissance I had on Mr. Cariello of Perryville was good. He was respected--even beloved--at PHS, and he was not anyone whom our faculty considered to be a “doomsday” principal option at the time. Still, I was struggling.
My first principal had entrusted me with a leadership role in organizing school-wide professional development. She gave me this role after my second year of teaching, and it was a role I valued and wanted to continue. I was nervous that this new guy would come in and undo the framework I felt that we were just establishing in schoolwide literacy. I had heard that most principals come into a building with an agenda, and usually that agenda involves major changes. I reached out to him via email that summer and expressed a willingness to meet, thinking he would probably brush me off.
Imagine my surprise when he not only responded to my email enthusiastically but also invited me to start attending what we used to call “lead teacher meetings” (now “instructional cabinet meetings,” which are regular assemblages of school content leaders to discuss school issues). At that first “I-Cab” meeting, Vince explained that he did not, in fact, have a sweeping agenda to implement. He expressed his respect for our previous principal and the work she had done, and he said that his job in the first year was to observe and see what was working well before overhauling anything. Well, shut my mouth! Imagine the thoughtful self-restraint that approach involved: not to pretend that he had all of the answers and instead to indicate a willingness to learn before changing the game. And he did just that. In any field, that is rare in an incoming leader.
What came next was even more shocking. He stated the deeply held philosophical belief that, to best serve students, he viewed teachers (caring for their needs, ensuring their happiness in the building) as his primary focus, not students. Say what? No one says that in education. I was uncomfortable when he made this assertion. Dude, it’s about kids, remember? But his logic was solid: We must make sure that we are giving students everything they need to be happy, safe, and secure every day. Teachers are the front line on that, and he held us responsible for making it happen. If teachers feel supported and safe and are performing accordingly, he believed, then so will the kids.
In I-Cab meetings, he established early on that he wanted to know what we thought, even if we disagreed with him. He had opinions, but he wanted genuine feedback on those opinions. And although we all value polite and calm discourse, Vince didn’t mind if we “went off” on a topic and passionately vented about something that we believed was just plain wrong. Vince is, in fact, the first boss to whom I ever started a conversation with “What the hell, man?” when I was distraught over an important issue. He could have rightfully reprimanded me for that (and don’t try this at home, kids--I was out of line), but he knew why I cared so much about that issue, and he instead treated me with compassion and gave me the answers I requested. He cared more about the issue and my distress than about his own ego or my respect (in that moment) for the chain of command.
Vince is not threatened by people or ideas. Now, if you were going to argue your point, you better be ready for Vince to come right back at you with his rebuttal (and if you’re the overly deferential type who backs down the minute you hear a rebuttal because you’re terrified of authority figures, well, as Pat Head Summitt used to say, “Toughen up, buttercup”). But if you cared enough to spar, then Vince let it happen with no hard feelings. You could have a heated discussion about a school policy on Friday, one that tortured you all weekend wondering if you went too far in arguing with the boss, but on the following Monday, there’s Vince on bus duty, characteristically chewing gum and clutching his coffee thermos, waving you over to talk about what happened last night on The Sopranos.
Vince Cariello respected what teachers had to say, and he gave us the freedom to argue and to feel safe in speaking truth to power. This is not to say that my previous bosses in any of my other jobs had not encouraged me to be honest or could not handle debate. What was different with Vince was the degree to which he encouraged dissent and how he used those debates to help us all think more deeply about the issue. I've been relatively outspoken all my life, but Vince's example taught me to trust myself more in that regard, to stay focused on the work instead of on who is in the room. Having him guide me at that particular point in my career was invaluable.
Importantly, during Vince’s tenure as my principal, I was beginning to grow as a teacher leader in ways that required me to discuss important issues with people outside of my own school. He encouraged me in being completely authentic in those situations. Whether in an argument over Common Core standards, or in a county meeting about grading policies, or even in a meeting about PARCC testing with the future U.S. Secretary of Education, I have had the confidence to look directly in my bosses’ eyes and say what I really think, even if (especially if) they feel otherwise.
If we are going to do right by students, we must be honest when we think we are heading in the wrong direction, even if boldness costs us, even if we turn out to be wrong. Leaders like Vince understand that and foster a climate that assumes that everyone in the room cares about kids and will fight for them. That, in my view, is true leadership.
To this day, seeing Vince makes me instantly calm. His genuine warmth and natural honesty have put me at ease since day one. He’s just a good guy. He’s, above all, a family man, and he maintains friendships forever. I am personally indebted to him not only for believing in my abilities as a teacher leader but also for the many kindnesses he bestowed on me. From laughing at my jokes, to calming me down after The Sopranos series finale, to telling me honestly when I was being unreasonable with a colleague, to cheering me up on a bad day by using his iPod to show me the Don Ciccio death scene from The Godfather, to telling me I wasn’t a bad person after I lost my cool with a couple of AP kids, to remaining calm during every school renovation mishap, Vince Cariello has always had my back.
After only three years at EHS, Vince was promoted to Executive Director of High Schools. I knew I would miss him, but he had shown me three years earlier that changing leaders did not mean that the world was ending, that perhaps I could observe and listen before making judgments, too. He would later visit EHS in that new role and could sometimes be found (chewing gum, clutching his coffee thermos) slipping right back into bus duty. Power positions did not change his natural humility, his warmth, or his openness.
Vince has become one of my litmus tests for people. If you love Vince Cariello, we’re cool. If you are in any way on the fence about him, then I start to wonder if you’re just ill, or under the influence of heavy medication, or perhaps, as Jack Nicholson would say, you can’t handle the truth. I mean, seriously, what the hell, man?