Episode 294: 5 Leadership Traps to Avoid as the School Year Begins
The beginning of a school year brings an energy that is hard to match. The building is ready, staff members are reconnecting, priorities have been established, and leaders walk into the year determined to lead with clarity and intentionality.
Then the students arrive.
Suddenly the emails pile up, meetings fill the calendar, parent concerns emerge, staffing challenges demand attention, and the urgent begins competing with what you said mattered most.
In this special midweek episode of Leaning Into Leadership, Dr. Darrin Peppard challenges school leaders to recognize five common leadership traps that can quietly derail their best intentions during the opening weeks of school.
Darrin explores why presence is different from simply being visible, how the Cycle of Chaos can allow urgency to rewrite your priorities, and why communicating something once doesn't mean people understand it. He also challenges leaders to stop solving every problem themselves and to recognize the important difference between giving someone grace and simply avoiding a necessary conversation.
The five leadership traps:
- Retreating to your office once students arrive
- Letting urgency rewrite your priorities
- Assuming everyone understood the opening-day message
- Trying to solve every problem personally
- Waiting too long to address something you already know isn't right
At the center of the episode is one question every school leader should consider as the year gets underway:
Is the leader you're becoming in September the same leader you intended to be at the beginning of August?
You probably won't lose your school year in the first few weeks. But you can establish habits during those weeks that you'll spend the rest of the year trying to undo.
Be intentional now. Protect what matters. And go have a Road to Awesome year.
In This Episode
- Why presence matters more than performative visibility
- How the urgent can quietly replace your real leadership priorities
- Why your calendar tells the truth about what you value
- The difference between communicating a message and creating clarity
- How solving every problem can actually weaken the people around you
- Why servant leadership is about empowerment, not doing everything for others
- The difference between grace and avoidance
- Why addressing small issues early protects the culture you're trying to create
- How to recognize leadership drift before it becomes your new normal
Key Takeaways
“You can't recognize what you never see.”
“Your calendar is going to tell the truth about your priorities long before your mission statement ever will.”
“Don't confuse delivering a message with creating clarity.”
“Don't just solve problems. Build problem-solvers.”
“What we tolerate teaches a lesson.”
“Clarity early is almost always easier than making corrections later.”
This Episode Is Sponsored by HeyTutor
HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers.
Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com.
Darrin Peppard (00:00)
All right, my friends, welcome into episode 294 of the Leaning Into Leadership Podcast, our usual midweek, mid-month edition, this one for the month of August. And you know, there is something pretty special about the beginning of the school year. That's what mid-August has me thinking about, is the beginning of the school year. And I I look back and I reflect on so many.
beginning of the school years for me, 26 of them, in fact. And when I think back on them, there are some things that consistently were true. The building looks great, the floors are shiny, you can smell the wax. bulletin boards are up and and the staff is back together. And you know, by now, for a lot of you, you've had that kickoff meeting and you've talked about the vision that you have for the coming year.
You've spent the time digging into your priorities and maybe even introduced the theme that you have for the year. There's this energy and an optimism that comes with the beginning of the year that is really hard to beat, and you won't see it at any other time during the year. There's this sense that, hey, this year it's gonna be different. And then the kids show up, and then the buses start running and the emails start coming and somebody calls in six.
And then a parent needs to see you, and then there's a scheduling issue, and on and on, right? You know, a student has a rough morning, or something breaks in the building, or something along those lines, and all of a sudden the leader that you intended to be starts competing with the leader that the day-to-day is demanding that you become. That is what I want to talk about today on this episode. Because
You're probably not going to lose the entire school year in the first few weeks, but you can absolutely establish habits during those first few weeks that you'll spend the rest of the year trying to undo. So for today's episode, I've got five leadership traps I want you to avoid as the school year gets underway. Now, before we do that, a quick word from our friends at Hey Tutor.
This episode of Leaning Into Leadership is brought to you by Heytutor. As schools begin another year, leaders everywhere are thinking about how to make sure every student gets the support that they need to be successful. And we know that sometimes students need more time, more attention, and more targeted support than the regular school day can provide. That is where Heytutor comes in.
Hey Tutor partners with schools and districts to provide high-impact in-person tutoring in literacy and math, putting trained tutors alongside your teachers and giving students the additional support they need. And HayTutor has earned the National Student Support Accelerators Tutoring Program Design Badge, recognizing its alignment with research-backed practices for high-impact tutoring. If accelerating student learning is one of your priorities this year,
And I'm guessing that it probably is. Take a look at what Heytutor can do for your schools. Visit Heytutor.com to learn more
Or even better yet, hit the link down in the show notes to let them know you heard about them here on the Leaning Into Leadership podcast. And now, let's talk about five leadership traps that can derail all those great intentions that you had when this school year very first began.
Okay, everybody, welcome back in and welcome again to this special midweek edition of Leaning Into Leadership. Really wanted to drop this special extra episode this week because right where we are right now at this time in August, as this episode is releasing, it's the 19th of August, and some of you have already started school. Actually, today, as I'm recording this on the 17th of August.
I've had multiple leadership coaching calls with schools who are two weeks in, three weeks in, or even just, just getting started. For some of you, that's this week. Your teachers are coming back. Others of you, you're just a few days away. But wherever you are on that timeline, I want you to think back to conversations that you've had as a leader over the past few weeks. What did you tell your staff was going to matter this year?
What did you say to your leadership team that you wanted the year to feel like? Maybe what did you commit to doing differently as a leader? Looking yourself in the mirror and saying, I'm gonna commit to doing this differently this year. Because here's a question I want you to carry with you throughout today's episode. And this one's not a long one. This one's probably gonna land somewhere in that 15-minute mark. So all throughout this episode,
Just keep coming back to this question. Is the leader that I become in September the same leader I intended to be at the beginning of August? Now, that is not a throwaway question. Remember, I have been a principal. I've lived this. I've walked into a school year convinced that this was going to be the year that I spent more time in the classrooms. This will be the year that I delegate more responsibilities to those around me.
This will be the year that I really protect my calendar, develop my assistant principal stay focused on instruction, and not allow myself to get sucked into every little problem that came into the office. And then the school year started. You see, the intentions were never the problem. It's the systems and the habits needed to protect those intentions that were the problems. That's why I want to give you.
Five traps to watch for as this year gets going. So here we go. Trap number one: retreating to your office once the students arrive. And this one will happen incredibly fast. During those opening days with staff, you are everywhere. You're greeting people.
You're hanging out with your teams, you're having lunch with people, you're you're out and about in the building. You know, you're checking in with your new people, you're catching up with people who've been in the building for a while, you know, laughing and joking in the hallways and and hearing about their vacations and looking at pictures, and you're doing so much that is focused on relationships and culture and connection. And that stuff's great, that's important. But then the students arrive.
And all of a sudden, your office becomes the central command unit. You are getting hit with email and phone calls, and meeting after meeting after meeting. Throw in discipline, throw in parent concerns, and of course a mountain of paperwork and
Without consciously deciding to do it, you slowly disappear from the places where your leadership matters the most. And I definitely want to be clear about something here. I'm not talking about performative visibility. I'm not talking about walking through the cafeteria so everybody can say, hey, the principal was in the cafeteria. I'm talking about presence. And there's a difference between being seen and being present.
Being present means you're close enough to the work to understand what's actually happening. You're in more than enough classrooms to see what your teachers are truly experiencing. You're in the hallways enough to know what it is your students are experiencing at school on a day-to-day basis. You're around your staff enough that conversations can happen organically instead of everything requiring that they make an appointment.
And there's another benefit to that presence. See, when you're out in the building, you get to see the good stuff. You see the teacher that stayed an extra 30 or 45 seconds with a student who is struggling a little bit and needed maybe just some encouragement. You know, you might get to see the custodian or the member of your nutrition services team who stopped what they were doing to just help a kid out.
You. You might see one of your one of your office staff who somehow de-escalated a parent and allowed them to feel heard and valued. You see, you can't recognize what you never see. So before your office becomes the place where your school year goes to disappear, build some habits that keep you connected to the work. Really, really think about this.
protect your presence. Trap number two, letting urgency rewrite your priorities. Here comes the cycle of chaos. If you have listened to this podcast for any length of time, or maybe you have seen me speak in person, workshop or a keynote or maybe a a breakout session at a conference, i if any time in the last nine months you probably have heard this if if you
have done any of those things. Schools have this habit of generating an unbelievable amount of urgent work. I mean, let's be honest, in a school there is always something happening. And the dangerous part is most of that is legit. Like a parent that needs an answer probably really does need an answer. The staffing issue that has come up really needs your attention. And and there could be a student situation that
Genuinely matters and you've got to get in the middle of it. And there's probably a deadline of some kind that has come from your central office that is this Friday and it's not gonna go away. All of those things are legit. The problem is not that those things aren't important. The problem is when they become the only things that we are leading, we've stepped away from our priorities.
Look, if we're not careful, very easily September can take away every priority that you put together here in August and rewrite it for you. You know, I I'm sure at a point in time you have told your staff that your instructional leadership really matters this year. Okay. Show me your calendar. I'll bet you said relationships matter. Show me where you're spending your time.
You probably said that you really want to focus on developing your leadership team and that that really matters. Well, when is your next meaningful leadership team conversation scheduled? Maybe you said supporting my teachers really matters. How often have you been in the classrooms? This is why that intentionality matters so much. Again, if you listen to me, have heard me speak, you know that to me,
The two biggest things that really matter in your leadership are being clear and being intentional. And this is why being intentional is so important. Intentional leadership doesn't mean, though, that you ignore the urgent problems. It means that you refuse to allow urgent problems to become your entire job. So sometime this week, open your calendar. Don't look at what you plan to prioritize. Look at where your time is actually going.
Because your calendar is going to tell the truth about your priorities long before your mission statement ever will. Trap number three. Assuming that everybody understood the opening day message. Yep, you had the meeting. You showed the slides, you did the activities, you talked about expectations, and everybody nodded.
And maybe you had some form that they had to sign that, you know, is like the last page of the employee handbook or you know, some type of non-negotiables document or whatever that acknowledges that they heard what you said. You know, you might have even asked, does anybody have any questions? And odds are nobody raised their hand if you did. and hey, that's great. We're aligned.
Except that we might not be. This is one of the things that people can easily fall into the trap with, assuming that because something was communicated it got understood, they are not the same thing. Have you ever had that conversation with a teacher?
Just be you know, just because you taught it doesn't mean they learned it. It's the exact same thing. Just because you said it in the opening staff meeting doesn't mean they heard it. Doesn't mean they understood it. You know, you might have spent the whole summer thinking about your priorities. you know, you've you've talked about them with your leadership team, you've wrestled with the language, you built the presentation. maybe you heard me speak about this over the course of the summer somewhere, maybe here on the podcast, and then
Your staff heard it on a Tuesday morning or whatever, there's a huge difference in the familiarity. And that's why we talk so much about shared language. it requires repetition. People need to hear it over and over and over, and then they need to see it over and over and over. They need opportunities to actually use it. Then they need to see leaders, the leadership team, reinforcing it through decisions, through actions, through how they model.
If something matters enough to say it on opening day, it should matter enough to keep talking about it in September and in October and in November. Because communication isn't complete when you've just said it. Communication actually is complete when people understood when people understand it well enough to act on it. Don't confuse delivering a message with creating clarity.
Trap number four, trying to solve every problem personally. Look, this one, this one was so hard for me, especially early on in my principalship, because I wanted to help. I wanted to be a servant leader. And I was honestly pretty good at solving problems. So when somebody brought a problem to me, I solved it. Teacher has an issue, I got this. I'll take care of it. Upset parent, send them to me.
Student problem? I'm all over it. Scheduling problem? Hey, let me look at it. I know that schedule inside and out. And every time I solve one of those problems, I got a little shot of validation. It was like, yeah, look at me getting things done. See? I'm helping. The problem was I was unintentionally teaching everyone around me something. Just bring your problems to Darren. He'll take care of it. He'll solve them.
And eventually I had helped myself right into the core of the cycle of chaos. The beginning of the school year is a prime superhero complex season because there are so many problems everywhere. But your job isn't to prove that you can solve more problems than everybody else. Your job is to build an organization filled with people who can solve problems.
So the next time somebody walks into your office with a problem, resist the urge to immediately give them an answer. Instead, ask a question. Something like, What do you think we should do? Or what options have you considered? Or what do you think a good outcome might look like? Maybe who else needs to be a part of this? Now
It might take a little longer today, and it might even feel like you're putting them off, but you're not. It builds capacity for tomorrow. And to me, that's that's leadership. Don't just solve problems, build problem solvers. You've probably heard me say it here before, but truly servant leadership is not about doing it for them. It's about empowering them to do for themselves. Track number five.
Waiting too long to address something that you already know isn't right. And I had this conversation with somebody that I coach earlier today. Some things that she is seeing as a new principle this year that needed to be addressed immediately. And she has dove right into them. And I'm very happy that she has, because they were some things that just flattened to be addressed. And it could easily be that this one is of the five traps the most uncomfortable.
Because first off, it's early in the year and you definitely want things to feel positive. You want your people to be excited and you don't want to be the leader who's coming down on somebody during week two. You know, the the the one I was just mentioning, she said to me, you know, Darren, what I don't want is to allow things that aren't okay to continue, but I also don't want to come across as a micromanager.
or somebody who just must have things their way. So when you notice something and you let it go, you know, maybe something like somebody isn't following an agreement that the team made. Maybe there's a behavior that doesn't match the culture that you've said you're trying to create.
maybe it's not something that's a legal requirement. Maybe it's something small enough that you convince yourself, you know, this isn't worth addressing yet. And you start to think, hey, I'm just going to give this a little bit of time. And sometimes that's absolutely the right call. But sometimes we aren't giving it time. We're just simply avoiding the conversation. Those are very different things.
Because here's what happens when we repeatedly walk past something that doesn't match the expectations that we've established. We are quietly establishing a new expectation. What we tolerate teaches a lesson. That doesn't mean that every mistake requires a formal conversation. It definitely doesn't mean that you jump on people the first time they miss something.
What it does mean is leadership requires enough courage to recognize the difference between grace and avoidance.
If you have established an expectation, support people so that they can meet that expectation. If you said something matters, your actions need to demonstrate that it actually matters. Clarity early is almost always easier than making corrections later. So, again, five traps that I want you to challenge yourself to stay away from. First, retreating to your office once the kids arrive.
Second, letting urgency rewrite your priorities. Third, assuming everyone understood that opening day message. Fourth, trying to solve every problem personally. And five, waiting too long to address something you already know isn't right. Now none of these sound catastrophic. That's precisely why they're dangerous. They lull you to sleep.
Leadership rarely gets derailed because somebody wakes up one morning and decides, you know what? Today I'm gonna stop being intentional with my time. No, it happens gradually. It starts with a canceled classroom visit. it's one week where you don't meet with your leadership team like you should have. Maybe it's one problem you decide it's easier to just solve this myself than to teach. Whatever it is.
When you put things off, push that conversation to later or or whatever. Eventually, the leader that you intended to be gets replaced by the leader who's just simply trying to survive the day. So here's my challenge for you. This is my my final piece for this episode. Think back to yourself a few weeks ago, before the kids arrived, before your email inbox exploded, before your schedule gets all filled up and
cycle of chaos comes knocking at your door. You had some ideas about the leader you wanted to be this year. You had some commitments that you wanted to make to yourself.
You want to do some things differently. Don't lose that leader. Again, is the leader that I'm becoming in September the same leader I intended to be at the beginning of August? And if the answer is no, that's okay. You're early on. This is a good time to catch it and a good time to make some adjustments. Reclaim your calendar, get back into classrooms.
Revisit an agreement that you maybe have, delegate something that you've been holding on to. Have the conversation that you've been avoiding.
Again, you won't lose your year in the first few weeks, but you can establish habits in the first few weeks that you'll spend the rest of your year trying to undo. Be intentional now. Protect what matters now. Go and have a road to awesome year.
Thank you so much for joining me here on this special midweek episode of the Leaning Into Leadership Podcast. As always, rate, review, subscribe, share this show with somebody else who might really need to hear this content. And as always, get out there and have a road-to-awesome week.