Many (most?) of the blogs I have composed over the nine years of Teach & Serve reflect on or reference conditions wherein good leadership is present in a school. They are written from a perspective assuming solid norms and procedures, relatively healthy environments, and excellent standards for behavior.  

Let us be honest: those conditions do not always pertain.

Where does that leave individuals who wish optimal (or, at least, functional) leadership is in play? Where does that leave those who aspire to greater things for themselves and for their schools? Where does that leave people who seek perpetual improvement?

These are challenging questions, but there are answers to them.

Like the best answers, they start from within us. They start with us making honest and clear assessments of who we are in our leadership and of how we relate to the leaders and systems around us. The best answers ask us to ask ourselves hard questions.

And to answer them.

Good leaders know that one of the fundamental qualities of leadership is authenticity. I have written previously that I believe it to be the central and most important quality of a good leader. Good leaders, then, take the questions they are posing outward and turn them within.

If leadership is bad in our schools, we must ask ourselves if we are part of the issue. What role have we played to sour the milk? Have we contributed to an environment that is less than ideal? We must be willing to examine ourselves as a necessary first step.

And what happens, then, if we find that we have – in good faith – done all we can to eliminate issues, to find middle ground, to offer constructive approaches, to build and become bridges? What do we do when our leadership is actually not very good or working in ways that counter the well-being of the school?

We must, then, assess what change we can make from where we are. We must consider who we can help and for what reason. If our challenge of authority and status quo and broken systems is for the good of our students (and the good of the adult community – a secondary good; students come first) then we are called to confront.

We must respectfully disagree and offer alternatives. We must exercise the authority we have as teachers and as educational leaders within the same structures our chairs and administrators occupy. We must speak truth – truth to colleagues, truth to power. We must do so offering suggestions and solutions, through-lines and conclusions and ways forward. We must be willing to suffer slings, arrows, criticisms and critiques.

When we are authentic, when we act from our true selves, all of this, though incredibly heavy to shoulder, is worth the weight.

If our systems hurt our students, if our leaders are negligent in their most important tasks, they must be examined and changed. They might even need to be set aside or torn down.

However, our seats in the school, our positions and our power along with the management and leadership styles of our superiors may make true and lasting collaboration and change so difficult as to be impossible.

This can be a bleak state of affairs and cause crises of the heart.

When leadership does not work and is unwilling to reflect and consider change, authentic leaders are in painful positions. If one has done all one can on behalf of students to confront challenges and bad actors, to affect change and to advance the institution and there is no way forward, another question comes into play: is my presence here so important for those I serve that I must stay?

If the answer is yes, it is good to remember that systems alter over time and leaders do not stay in place forever.

If the answer is no, it may well be time for an individual to change one’s circumstance. While that is easier written than done, it may be an inevitable conclusion and a legitimate alternative to continuing frustration and pain.

The best answers start from within. Knowing ourselves is a significant key.

Today is Valentine’s Day.

It is also Ash Wednesday. 

Though this confluence of days is rare, it is not as rare as one might think. It just happened six years ago in 2018 and will happen again in 2029. 

At first glance, the juxtaposition of Ash Wednesday and Valentine’s Day may seem incongruous, and their coinciding on the same day may seem peculiar. Upon closer inspection, these two observances share more than a few similarities.

Ash Wednesday is a day that is not universally looked forward to by Christians, though one can argue it should be. Valentine’s Day can be rightfully critiqued for its commercialism and its dubious origins and the peer pressure it generates. 

Like most things educators teach, there is another side to those perceptions.

Both Ash Wednesday and Valentine’s Day are about giving. On Valentine’s Day, many people celebrate their relationships by giving each other gifts. On Ash Wednesday, many Christians celebrate their faith by giving up things that draw them away from God. Appropriate and good pursuits, both. 

Similarly, both Ash Wednesday and Valentine’s Day carry a bittersweet undertone. On Ash Wednesday, a common mantra is “remember you are dust and unto dust you shall return.” That is a phrase I recall from over 50 years of Mass and ash distribution, hearing the minister intone those words while dust spilled into my eyes. Christians are to spend this day prayerfully and penitently, beginning their 40 day Lenten journey. On Valentine’s Day, many are excluded from the joy they are told they are supposed to feel as they do not have a significant other. I remember that pain from the Valentine’s Days during which I was uninvolved.

Do not both of these occasions serve as poignant reminders that our love for others should surpass self-love? Do they not prompt us to strive for improvement in the most significant relationships of our lives?

Ash Wednesday and Valentine’s Day are about intentionality. They are about relationship. Most importantly, they are about love.

Love. 

That is something we call all embrace this February 14th.

I recently had cause to reflect on something a good friend of mine said a few years ago: “When disagreeing, the negative opinion can seem to be more informed than the positive opinion. We should be careful with that.”

In the ensuing years and in various contexts, I heard my friend’s voice in my ear on more than one occasion and I have not only come to believe that what he said is true, I also believe that how an educational leader (or any leader for that matter) addresses responds to negative opinions, especially in the realm of decision making, says much about how that leader leads overall.

Leaders must contend with the reactions of those being led – both the positive and the negative reactions. Part of leadership is to put the positive in perspective while engaging the negative and sorting through both to discern a direction or to uncover truth. 

Upon which kind of reaction does a leader spend the most time? 

Upon which should a leader spend the most time?

There is a reason – and it is a bad one – that the old adage “the squeaky wheel gets the grease” is shared with such regularity: because it is true. Those who complain often and loudly get an audience, get recognition, get traction. Those who boisterously and repeatedly make arguments find themselves in administrators’ offices, whether to be heard or to be reprimanded. Most saliently, it seems to me that those who express the negative are too frequently regarded among the intelligentsia of faculties and staff.

Negative opinions are not the most informed, but they often seem that way.

Why is that? Why do negative opinions seem to be the smart opinions?

The responsibility for this challenge, while it is a shared one, falls more squarely upon the leader than upon the complainer. How the leader addresses and repairs the squeaky wheel is critical. How the leader proceeds in the face of negativity and complaints says far more about the leader than the constituents. 

If the leader gives equal weight to each complaint with limited discernment about what is actually central and informed and what is not, that does not speak well of her leadership. If the leader gives too little weight or cannot distinguish what should be handled and what should be turfed, that, too, is a significant problem.

But the leaders who feel that every negative opinion must be addressed, countered, taken on and confronted because there is a sneaking suspicion that the rationale behind complaints is somehow better reasoned and, therefore, has more validity that other thoughts are just wrong minded.

It can feel as though negativity is sharper, smarter, and better developed than positivity, but that simply is not the case. How a leader deals with the predilection in himself and others to jump to this conclusion can make or break the leader in critical moments and at critical times because complaints can underscore crisis. The leaders’ response to them can promote crisis.

Watch leaders you admire handle negativity. Watch leaders around you address complaint. They will be confronted by both. What they do when confronted tells a story about their leadership and it is an important one.

When I think back to the over twenty-five years I spent as a high school teacher and administrator, I remember many an afternoon drive home during which I had LONG conversations with people who were not in my car. I would talk to the principals who may have upset me by making a decision with which I did not agree. I would chat with the department chairs whose policies made it impossible for me to do my job well and to be the best teacher I could be. I would talk to the students who pushed every and all of my buttons during the day. I would have conversation after conversation, often thinking “I wish I’d said that” and sometimes, in the case of conversations I repeated ad infinitum in my head, I would convince myself I had, in fact, come up with the perfect rejoinder in the moment.

Only one person I can think of has ever been able to recreate the circumstances surrounding a conversation to get to actually use such a rejoinder, and it did not go so well for him:

The bottom line on these kinds of conversations is that, most likely, what I thought I wanted to say was, in the end, better left unsaid.

As teachers, educators and administrators, we are called upon to make decisions – all kinds of decisions – sometimes with time to ponder and consider, sometimes in a split second. As educators, we encounter people all day long. Some of them come to us at their best and some at their worst. Most come to us somewhere in between. They come to us with questions, with concerns, sometimes with emotion. They come to us with challenges that, perhaps, they want us to solve or challenges that they are putting to us.

And they find us, because we are human, in whatever state we happen to be in at the time. We might be up or down, happy or sad, relaxed or keyed up. What I discovered in my years in schools is that it rarely mattered (or, rather, it only mattered to an empathetic person) what my condition was when being approached. Typically, when someone wanted something, wanted to talk, wanted to confront, their moment was now no matter how I felt about it.

That is perfectly fine. Administrators especially must be ready for such conversations no matter their mental or emotional state. What are we doing in school leadership if we are not as available, physically and emotionally as we can be, to help, to aid, to assist? I would argue that if being available to those around you is not in your top three goals as an educational leader, you should consider another line of work.

In some instances, these contacts are terrific. 

I am not writing about those here. 

I am writing about the ones that are not terrific, the ones that get under our skin, the ones that truly bother us and leave us having phantom conversations in the car on the way home.

We get upset. We are human. We get overwhelmed. We are entitled. We get frustrated. Okay, wait… Here is where we need to be careful.

This is where I need to be careful.

“I should have said this” is very dangerous. When I run these moments on a loop in my mind, I become worried that, in a trying moment, I might actually say what I thought I should have said or something like it from one situation to the next. I might get so upset that I would feel justified. 

I can absolutely see that happening. If I try hard enough, I can remember times it did happen.

As educational leaders, we can get so overwhelmed we give ourselves a pass. We can get so frustrated that we might cross a line that cannot be uncrossed or burn a bridge that cannot be rebuilt.

We are confronted by such perils dozens of times a day.

We must be careful. We are leaders. We are public figures. And, no matter whether we believe it is fair or not, we are held to a higher standard.

In the heat of the moment or an hour later or in our car on the way home or as we are about to press “send” on that email, there is a simple question to ask: is what I am about to do helpful?

If it is not, I would argue it should not be done. If what I am about to do is not constructive, I need to discard the thought. If what I am about to say only tears down with no possibility of building up, it is the wrong way to go. 

Is what I am about to do helpful?

Good question to ask.

Repeatedly.

I have shared this post before but, as my father’s birthday is tomorrow and, for me, these messages never get old, I share it again today.

My father was a massive influence on my educational career. He still is, over a decade after his death.

At this point in my life, I have come to understand that we tend to idealize those people who have come and gone in our lives. By this I mean those we have lost to death or to movements and flows of life or to other circumstances both within and beyond our control. When those we love move out of our lives, we have a tendency to idealize them – who they were, what they stood for and what they said.

I guard against this temptation when I think of my father, though I am sure that a bit of idealization sneaks in. How could it not? I loved him.

Dad, if you asked, would have said terrible things about school. He may have even said terrible things about teachers. Strike “may have.” Dad did say terrible things about some teachers and those things may even have been true.

Dad attended the same Jesuit high school I did and he told great stories about it, including the undated, signed notes my grandmother would give him of the “Please excuse Mickey from class…” variety and the tale of a teacher picking up a talkative student’s desk and throwing that student, desk and all, through the door of the classroom without skipping a beat of his lesson.

Dad could tell stories.

Dad could also give advice, when asked, so, like a good son I never really asked him his advice about teaching. Terrible, isn’t it? Dad wasn’t a professional teacher, didn’t seem to have adored his educational life and I didn’t turn to him for advice when I chose the vocation.

Looking back on who he was and how he lived and, perhaps, idealizing him a bit, I think I can discern what he may have told me had I asked him.

Dad never took himself too seriously. Seriously. Though he was involved in a serious profession and found himself, in his work as a deacon, dealing with people in challenging times of life, he never let the moments get the best of him. He also never let himself think he was any better than anyone else. I remember him telling the story of when, during a baptism he was performing, he continually referred to the child – let’s call the baby “Chris” – as a boy when, in fact, she was a girl. “It’s a girl, dummy!” the baby’s grandmother finally corrected him during the ceremony. Dad loved to tell that story.

Teachers and administrators need a healthy dose of self-deprecation. If they take themselves too seriously, the work can become burdensome. They are public figures whose mistakes are going to be critiqued and scrutinized. If educators live and die with every challenging moment, the work can take a deeper emotional toll. Educators are well served by stepping back and smiling at themselves. Often.

Dad was very decisive. There may have been a lot of internal debate going on with my father and, surely, he and my mom talked about big decisions in their lives but, professionally and personally, Dad struck me as very decisive. Once he had made a decision, he didn’t spend too much time looking back.

Educators are called upon to make decisions minute-by-minute. While not all of these decisions are filled with import, many need to be made with confidence. This doesn’t necessarily imply that decisions must all be made quickly, but, once decisions are made, dwelling on and second guessing them as a matter of course can be very draining.

Dad had a great sense of humor. He could make fun of almost anything and could be highly irreverent.

Teachers and administrators who cannot laugh and who do not have a sense of humor can certainly do the job. They can do it at a high level, even. But I have found that those who don’t have a sense of humor simply don’t enjoy the work as much as those who do. If you’re not going to enjoy being in a school, the other rewards of the vocation may not be enough for you.

Dad connected with people. When Dad died, I spoke in the eulogy about his “guys.” Dad had many, many “guys,” people whose lives and his had intertwined over the course of his work with the Church and simply because of the man he was. There was a great number of people who called Dad “friend” and a lot more whose lives had been touched by him and, surely, who had touched his life in turn.

Much like not having a well-developed sense of humor, it is possible for educators – teachers and administrators – to do the work without connecting with kids and with parents and with their colleagues. It is possible. I am just not sure how well the work is done by people who don’t enjoy connecting with others. Actually, I am pretty sure that those people don’t do the work nearly as well. Teachers and administrators must connect. It’s part of the job description.

Dad had a terrific sense of justice. I suppose having a strong sense of justice was part of Dad’s job description as a deacon. He was very in tune with this, could sense an imbalance of power or a bad situation readily and reacted strongly to them. He was motivated by those who had been abused by any system, inspired by David vs. Goliath stories, championed those who had less. The homeless came to Dad. He worked hard for those with less. He never stopped fighting in this area. He also, from the pulpit, didn’t shy away from talking about issues of justice, even when such homilies made people uncomfortable.

Educators are called to not only be fair and just, they are called to highlight injustice around them. They are called to act in a just manner and to point out to developing young minds the injustice that exists in the world. Further, they are compelled to help students understand that they can be part of changing unjust systems. If we’re not about this as we teach, we’re simply doing a disservice to students.

Dad was a great storyteller and loved to listen to others’ stories. I miss a lot about being able to talk with and listen to my Dad. I try to emulate much of what he was in my own life. Yes, as I have written above, I know that I idealize my father in many ways, but not in this one. Dad was a terrific storyteller and could command “the room” so to speak. He told wonderfully engaging and funny stories. He also loved to listen to others telling stories and would often ask for the same story to be told over-and-over again. He would want to hear about the same moment, the same incident, the same funny instance. And, when he listened, his reactions and smile and attention validated the storyteller and made that person feel very special.

Shouldn’t educators tell great stories? Beyond delivering content and inspiring skills in our students, shouldn’t we also be able to tell them great stories about our subject matter and convey or love of it? Shouldn’t we also listen to those around us at least as much as we speak to them?

My father, who professed a dislike of school and who I never heard anyone call “teacher” was one of the greatest teachers I ever had. He should have written a book about education. If he had, it would been titled Lessons about Teaching from a Guy Who Didn’t Like School.

I would have bought that book.