The Post

It started as a post.

Then a screenshot of the post.

Then a screenshot of the screenshot.

By midnight it had been shared four hundred times. By morning my phone had sixty-three unread messages. Parents I hadn’t spoken to in years. Community members I had never met. A local news reporter asking for a statement before eight o’clock.

The post accused one of my teachers of misconduct.

It named him. It named the school. It named me.

And half the people who read it had already decided it was true.

The teacher’s name was Mr. Callahan.

Eleven years in my building. Ninth grade English. The kind of teacher who stayed late, knew every kid’s name, coached the speech and debate team on his own time. Well-liked. Trusted. The kind of colleague other teachers went to when they needed advice.

The post claimed he had made inappropriate comments to a student.

It offered no specifics. No date. No context. Just the accusation, a name, and a school.

That was enough.

I want to tell you I handled the first hour well.

I did not.

My first instinct was to defend him. Eleven years of trust, dozens of parent compliments in my files, a spotless record — I knew this man. And everything I knew said the accusation didn’t fit.

My second instinct was to say nothing publicly and wait for it to pass.

Both instincts were wrong.

Here is what I have learned about social media accusations and leadership — the hard way, in real time, with my name in the thread.

Silence reads as guilt.

Defense reads as cover-up.

And the truth — whatever it turns out to be — moves at a fraction of the speed of the original post.

What a leader has to do in that moment is the hardest thing imaginable.

You have to hold two things at the same time that feel like they contradict each other.

The first: every accusation deserves a serious, thorough, fair investigation. Every one. Regardless of how well you know the person. Regardless of how implausible it sounds. Because the alternative — deciding in advance that something couldn’t have happened — is how institutions fail the people they were built to protect.

The second: an accusation is not a conviction. A post is not evidence. And a person’s reputation — their career, their family, their name — deserves to be protected from the momentum of a news cycle until facts are actually known.

I called Mr. Callahan at seven-fifteen that morning.

I told him what was happening. I told him I was taking it seriously. I told him I was also not going to treat him as guilty before a single fact had been established.

Then I called the district. Then HR. Then our legal team.

And then I wrote a statement — one paragraph, measured, careful — that said the school was aware of the post, that we take all concerns about student safety seriously, and that a proper review was underway.

I did not name him. I did not defend him. I did not dismiss the concern.

I said: we are looking into this, and we will follow the process.

The investigation took eleven days.

What it found was this: a comment Mr. Callahan had made in class — about a novel the students were reading — had been heard differently by one student than he had intended it. There was no pattern of behavior. No prior complaints. No corroboration. The student’s concern was real and it was heard. The comment was addressed directly with Mr. Callahan, who was genuinely shaken that his words had landed the way they did.

No misconduct. No discipline.

A conversation that should have happened in the classroom before it ever reached the internet.

The post, of course, was never updated.

The shares did not come back.

The four hundred people who saw the accusation never saw the outcome.

That is the thing about social media and institutional trust that no communications training fully prepares you for.

The accusation travels at the speed of light.

The truth travels on foot.

Mr. Callahan came back to his classroom.

He was quieter for a while. More careful with his words — not in a bad way, in a thoughtful way. He told me months later that it had changed how he thinks about the weight a single sentence can carry in a room full of teenagers.

I told him I understood.

It had changed how I think about a few things too.

THE TRANSFERABLE PRINCIPLE THIS WEEK

When an accusation goes public before the facts are known, a leader’s job is not to choose sides. It is to hold the process. Investigate seriously, protect the accused from presumption of guilt, and protect the community from presumption of innocence. Say less than you want to. Move faster than feels comfortable. And remember: the accusation will always travel farther than the outcome. Your job is to make sure the process is so thorough and so fair that you can live with it — regardless of what it finds.

What a Seventh Grader Taught Me About Motivation

His name was DeShawn and he did not want to be in school.

Not my school specifically. School generally. The whole enterprise. He’d decided somewhere around fifth grade that it wasn’t built for him, and he’d been quietly, consistently proving that theory ever since. Failed classes. Missed assignments. A guidance file that was starting to get thick.

Every adult in the building had tried something. Tutoring. Parent meetings. Incentive programs. Stern conversations followed by encouraging ones. DeShawn was pleasant about all of it. He’d nod, agree, and then return to doing exactly what he’d been doing — which was essentially nothing.

I decided to try one thing nobody had tried yet. I stopped talking about school.

I pulled him out of study hall one Tuesday afternoon, brought him down to my office, and told him straight up that I wasn’t going to talk about his grades or his attendance or his future plans. I just wanted to know what he was actually good at. Not what he was supposed to be good at. What he knew, in his bones, he could do.

He looked at me like I’d switched languages.

Then he told me he could fix anything with an engine. Dirt bikes, go-karts, his uncle’s pickup truck. He’d been doing it since he was nine. He described pulling apart a carburetor with a confidence and a precision I had never heard from him in any classroom. He was a completely different person talking about that engine than he was sitting in eighth period math.

I didn’t fix DeShawn. I want to be honest about that. He still had hard days. He still struggled with classes that felt disconnected from anything he cared about. But something shifted after that conversation — because for the first time, at least one adult in that building had gotten genuinely curious about who he actually was, rather than who the gradebook said he wasn’t.

He started showing up more. Not perfectly. More.

I started asking that question differently with every student and every staff member I worked with after that. Not “what do you need to improve” but “what are you already good at, and how do we build from there.” It sounds like common sense. It is common sense. It is also not how most schools — or most organizations — actually operate. Most systems are built around deficits. The gap. The missing standard. The thing that needs to be fixed.

But motivation almost never starts with what’s broken. It starts with what’s already alive.

THE TRANSFERABLE PRINCIPLE THIS WEEK

Before you try to move someone forward, find out what they’re already moving toward. In schools and in boardrooms, the leaders who figure that out first are the ones who get the most out of the people around them. Motivation isn’t something you install in a person. It’s something you find — and then connect to the work that needs to be done.

Until next time — the chair is yours.

Next issue: The parent meeting that changed how I think about conflict — permanently.

theprincipalschair.substack.com

When the Room Turns Against You

It’s the third Tuesday of October and you’re standing in front of your entire faculty.

You’ve prepared for this meeting. You have slides. You have data. You have a plan you genuinely believe in — a new approach to how the building handles chronic absenteeism, one you’ve spent two months researching, piloting in three classrooms, and shaping with input from your leadership team.

You start talking.

And within four minutes, you can feel the room shift.

It’s not loud. It’s never loud at first. It’s the crossed arms. The glance exchanged between the two veteran teachers in the third row. The question that isn’t really a question — “So are we saying that what we’ve been doing for fifteen years just doesn’t work?”

You’re not losing the argument. You’re losing the room. And those are two completely different problems.

I’ve watched strong leaders — smart, prepared, data-driven leaders — make the same mistake in this moment. They double down. They bring out another slide. They explain more clearly, as if clarity were ever the issue.

But the room didn’t turn because people didn’t understand. The room turned because people didn’t feel seen. And no amount of data fixes that. You can be completely right about your plan and still lose the people you need to execute it.

There’s a move I learned to make in exactly this moment and it feels counterintuitive every single time. You stop. You put down the clicker. And you say something like: “Before I go any further — what am I not understanding about where you are right now?”

And then you wait. Genuinely wait. Not to manage the pause. Not to show you’re listening. Actually, to hear what comes next.

What happens almost always surprises leaders the first time they try it. People don’t attack. They exhale. Someone says something honest. The veteran teacher in the third row says what she’s actually been thinking — which turns out to be a legitimate concern you hadn’t fully considered. Now you can address it directly instead of talking past it for the rest of the meeting.

You don’t have to abandon your plan. You don’t have to pretend the data doesn’t exist. But you have to earn the right to lead people somewhere new. And you earn it by proving — in that moment, in front of everyone — that you actually want to know where they’re standing before you ask them to move.

A leader who can read a room shift and respond to the emotion underneath the words — not just the words themselves — is the leader people follow into genuinely hard change. That skill is not soft. It’s the hardest thing in this work.

THE TRANSFERABLE PRINCIPLE THIS WEEK

When a room turns against your idea, the instinct is to defend the idea. The move that works is to defend the relationship first. Get curious before you get persuasive. People don’t resist change because they’re difficult. They resist because they’re uncertain and nobody asked them about it. Ask first. Lead second.

Until next time — the chair is yours.

Next issue: What a seventh grader taught me about motivation that no leadership book ever did.

theprincipalchair.substack.com

Leadership decisions from the real world of schools and organizations.

This Substack is reader-supported. To receive new posts and support my work, consider becoming a free or paid subscriber.

Issue #104

The Hire You Almost Didn’t Make

She wasn’t the obvious choice.

Her resume was thin compared to the other two finalists. Four years of teaching, no advanced degree, nothing on paper that made her stand out from the stack. When my assistant principal reviewed the candidates, her folder ended up on the bottom. That’s almost always where she would have stayed.

But something in her interview stopped me.

I’d asked every candidate the same question: “Tell me about a student you failed.” Most people flinched, recovered, and then told me a story that was really about how hard they’d tried. Understandable. Human. Not what I was looking for.

She didn’t flinch. She looked at me for a moment and then told me about a ninth grader named Marcus — specifically, painfully, and without a single hedge. No pivot to the silver lining. Just honest accountability and a clear-eyed understanding of what she wished she had done differently.

I hired her!

Seven years later she was one of the finest teachers I’ve ever watched work with at-risk students. Marcus had moved on by then, but she carried him with her into every classroom after that. You could see it in how she taught — the way she stayed a little longer, asked one more question, noticed the kid in the back who was starting to disappear.

Most hiring decisions — in schools and in organizations of every kind — over-index on credentials and under-index on character. That’s not because leaders are foolish. It’s because credentials are easy to measure and character is uncomfortable to probe for in a forty-five minute interview. So we default to the transcript, the degree, the years of experience. And we miss the person sitting right in front of us.

But there are questions that crack the window open. “Tell me about a student you failed” is one of them. So is “Tell me about a time you disagreed with a decision your supervisor made and what you did about it.” And simply: “What are you working to get better at right now, and what are you actually doing about it?”

The answers matter less than what the person does with the question. Do they go somewhere real or do they manage you? Do they sit with the discomfort or perform their way around it? Do they talk about growth like it’s a goal they’ve set, or like it’s something they’re genuinely living?

The best hires I ever made shared one quality above everything else. They were more interested in getting better than in looking good. That distinction sounds simple. In practice it’s rare. And in a school — where the stakes are children and the margins for mediocrity are thin — it’s everything.

THE TRANSFERABLE PRINCIPLE THIS WEEK

In your next hire — for any role, in any organization — build at least one question into the interview that has no comfortable answer. Then watch what the person does with the discomfort. Credentials tell you what someone has done. That moment tells you who they are. Hire who they are.

Until next time — the chair is yours.

Next issue: The board meeting that almost ended my career — and what I did in the parking lot afterward.

theprincipalchair.substack.com

This Substack is reader-supported. To receive new posts and support my work, consider becoming a free or paid subscriber.

Leadership decisions from the real world of schools and organizations.

This Substack is reader-supported. To receive new posts and support my work, consider becoming a free or paid subscriber.

Welcome back to The Principal’s Chair. I’m Larry. Let’s get into it.

Issue #103

The Moment I Realized I Was the Problem

It was a Wednesday afternoon in my third year as a principal.

I was sitting across from one of my most experienced teachers — nineteen years in that building, someone I genuinely respected, someone whose opinion of the school I trusted more than almost anyone else’s. She had asked to meet with me. She’d been careful setting it up, choosing the words in her email the way you choose your steps on ice.

She told me morale was struggling. She gave me specific examples, named specific moments. And then, after about ten minutes of that, she said something I wasn’t ready for.

“I think people are afraid to bring you bad news.”

I almost defended myself right there. I could feel the response forming — I have an open door, I ask for honest feedback, I’ve never punished anyone for telling me the truth. I had evidence. I had a whole case assembled and ready.

Instead I put the case down. I looked at her and asked one question.

“What makes you say that?”

What she told me in the next four minutes changed how I led for the rest of my career.

She didn’t say I was mean or unapproachable. She said that when people brought me problems, I solved them so quickly and so completely that they stopped feeling like contributors and started feeling like they were just delivering bad news to someone who would handle everything from there. They’d bring me a problem, I’d fix it, and they’d walk out of my office feeling somehow smaller than when they walked in.

I was so good at fixing things that I had accidentally taught my team to be helpless.

Sit with that for a moment. Because it’s a hard thing to hear about yourself — harder still because on the surface it looks like a strength. Decisiveness. Competence. Action orientation. Those are qualities every leader wants. But deployed without self-awareness, at scale, in a building full of professionals who need to grow, those same qualities can quietly close people down.

After that conversation I started doing something uncomfortable. When someone brought me a problem, I would ask them what they thought we should do before I said a single word. Even when I already had the answer. Especially when I already had the answer. Because my answer wasn’t always the point. Their development was the point. Their ownership of the solution was the point. A problem solved by a leader produces compliance. A problem solved by a teacher, with a leader’s guidance, produces growth.

The building changed after that shift. Not overnight — it never happens overnight. But over the following months, people started bringing me half-formed ideas instead of fully packaged problems. They started showing me their thinking before it was clean, before it was certain, before they were sure I’d approve. That’s the signal you’re waiting for as a leader. When people trust you enough to show you their rough drafts, you’ve built something real.

The teacher who told me the truth that Wednesday afternoon did me a professional favor I never properly thanked her for. She had every reason to stay quiet — it’s not easy to tell your principal that his strength is becoming a liability. She said it anyway because she cared about the school more than she feared the conversation.

That’s the kind of person you want on your team. And the only way to get that kind of honesty is to earn it — by proving, over and over, that you can hear hard things without making the person who said them regret it.

THE TRANSFERABLE PRINCIPLE THIS WEEK

The most dangerous blind spots in leadership are not your weaknesses. They’re your strengths operating without self-awareness. Ask someone you genuinely trust this week — not ‘how am I doing’ but ‘what do I do that makes your job harder without realizing it.’ Then listen without defending. What you hear might be the most valuable feedback you get all year.

Until next time — the chair is yours.

Next issue: What a seventh grader taught me about motivation that no leadership book ever did.

theprincipalschair.substack.com

This Substack is reader-supported. To receive new posts and support my work, consider becoming a free or paid subscriber.

Leadership decisions from the real world of schools and organizations.

This Substack is reader-supported. To receive new posts and support my work, consider becoming a free or paid subscriber.

Welcome back to The Principal’s Chair. I’m Larry. Let’s get into it.

Issue #102

The Conversation You Keep Postponing

You know the one.

There’s someone on your team right now — maybe there’s been someone on your team for weeks, possibly months — and you haven’t had “the” conversation yet. You’ve told yourself you’re waiting for the right moment. You’ve told yourself it might resolve on its own. And….You’ve convinced yourself you don’t want to damage the relationship or create unnecessary tension in an already full building.

But here’s what’s really happening while you wait. Every single day, the problem gets a little more expensive. The team sees it. They watch what you do about it, and when you do nothing, they’ve drawn their own conclusions about what accountability means in this place.

Your silence has already sent a message. And…. not the one you intend.

I postponed a conversation once for eleven weeks. I can tell you exactly what it cost me — two strong teachers who quietly lost respect for my leadership during that stretch, a department that developed a workaround culture because they stopped believing that accountability meant anything here, and a situation that was three times harder to address in week eleven than it would have been in week one.

Eleven weeks. For a conversation that ended up only taking twenty-two minutes.

The person I needed to talk to wasn’t malicious. They weren’t even fully aware of the impact of what they were doing. Which is exactly why the conversation needed to happen sooner. I wasn’t protecting them by waiting. I was letting the damage compound while telling myself I was being thoughtful.

Here’s what I’ve learned about why we postpone these conversations. It’s almost never about not knowing what to say. We usually know what we need to say. It’s about not wanting to be the person who says it — not wanting to be the one who makes things uncomfortable, who disrupts the order……. who has to watch someone’s expression change when they realize why you called them in.

But leadership requires you to be that person. Not because you’re hard. Because you care enough about the team, and about the individual, to tell them the truth before the situation makes the truth unavoidable.

The conversation you’re postponing right now almost certainly starts with something simpler than you’ve made it in your head. Something like this: “I’ve been meaning to talk with you about something, and I want to do it now while we still have room to do something about it.” That’s it. That’s the door. What’s on the other side is almost always more manageable than what you’ve been rehearsing at two in the morning.

The anticipation of a hard conversation is almost always worse than the conversation itself. I have sat across from angry parents, frustrated teachers, and defensive staff members — and in twenty years of doing this, I have never once walked out of a difficult conversation thinking I wish I had waited longer to have that. Not once.

What I have thought, more times than I care to count, is I wish I had done this three weeks ago. Because earlier always costs less. Eventually, trust doesn’t just vanish—it slowly dissolves. And with it goes your credibility, leaving behind a leader who doesn’t lead, but simply hides.

THE TRANSFERABLE PRINCIPLE THIS WEEK

The hard conversation you’re avoiding is not protecting the relationship. It’s slowly hollowing it out. The leaders people trust most are not the ones who never deliver hard news — they’re the ones who deliver it early, honestly, and with genuine care for the person across from them. Postponing is not kindness. It’s fear wearing the mask of kindness. Have the conversation. This week. Before you talk yourself out of it once again.

Until next time — the chair is yours.

Next issue: The moment I realized I was the problem.

theprincipalschair.substack.com

This Substack is reader-supported. To receive new posts and support my work, consider becoming a free or paid subscriber.

Leadership decisions from the real world of schools and organizations.

This Substack is reader-supported. To receive new posts and support my work, consider becoming a free or paid subscriber.

Welcome to The Principal’s Chair. I’m Larry — a former teacher, High School Principal, and small business owner who spent decades making real decisions in real buildings with real people. This newsletter is about leadership — the kind you learn not from a textbook, but from the moments that test everything you think you know. Twice a week I’ll bring you a scenario, my honest take, and one principle you can carry into your week — whether you lead a school, a team, or business organization . Let’s get into it.

Issue #101

The Decision Nobody Trains You For

It’s 6:52 AM on a Tuesday.

You’re in your office before anyone else arrives, like always. Coffee’s still hot. The building is super quiet in the way it is before the day starts — before the buses pull in, before the hallways fill, before the noise of four hundred decisions come at you all at once.

You’ve got seventeen things on your agenda. You’re already sorting them by urgency.

Then your phone rings.

It’s your head custodian. His voice is flat in a way that tells you before the words do. There’s a message written on the bathroom wall in the boys’ locker room. A name. A threat. A date.

Today’s date.

You hang up and sit there for exactly four seconds — because that’s all you get — and then you must become someone who knows exactly what to do.

The problem….nobody trained you for this moment! I mean, Not really. Your certification program gave you school law and curriculum theory. Your mentor told you to build relationships and stay visible. Your district handed you a crisis binder two years ago that’s been sitting on a shelf you haven’t touched since the day you put it there.

But right now, at 6:52 AM, it’s just you.

So, what do you do in the next ten minutes?

Most people freeze — not because they’re incompetent, but because the weight of the decision lands before the training kicks in. I’ve been in that room. I’ve made that call. And what I learned that morning has shaped every high-stakes decision I’ve made since, in schools and in every leadership role that came after.

Here’s the principle that carried me through it: clarity before action, but never clarity instead of action.

What that means in practice is this. You don’t need to know everything before you move. You need to know just enough. In a crisis, the leaders who perform best aren’t the ones with the most information — they’re the ones who can identify the three things they know for certain and build their first move around those three things alone. Not four things. Not a full picture. Three solid facts and a direction.

That morning, here’s what I knew for certain. There was a credible written threat. There was a name on that wall. And I had a building full of kids arriving in less than an hour.

That was enough. I called the school resource officer. I called my superintendent. I secured the locker room and positioned staff. I made a decision about that student before the first bus pulled in — with incomplete information, under real pressure, in real time.

Was it the perfect decision? I’m not sure perfect exists at 6:52 AM. But it was a sound decision, made with the information available to me, executed with enough confidence that the people around me could follow it. And that confidence — the willingness to act decisively even when you don’t have everything you wish you had — mattered as much as the decision itself.

The leaders who struggle most in a crisis are the o nes who confuse caution with waiting. Don’t misunderstand me. Caution is smart. Waiting for perfect information when people are depending on you is something else entirely. Learn to tell the difference, and you’ll make better decisions than most people around you — not because you’re smarter, but because you’re willing to move.

THE TRANSFERABLE PRINCIPLE THIS WEEK

In any organization, when a crisis hits, most people wait for someone else to have clarity first. The leader’s job is to manufacture enough clarity to take the first right step — even when the full picture isn’t there yet. Identify the three things you know for certain. Build your first move around those. Urgency and soundness together. Never one without the other.

Until next time — the chair is yours.

Next issue: The conversation every leader avoids — and why avoiding it always costs you more than having it.

theprincipalschair.substack.com

This Substack is reader-supported. To receive new posts and support my work, consider becoming a free or paid subscriber.