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How to Create the Perfect Principal Entry Plan [Part 1 of 6]

Note: This post originates from ’s Build Leadership Momentum: How to Create the Perfect Principal Entry Plan.
The book was written before the substack started. So it’s kind of what we’ll be doing in the future, in reverse. Starting in early 2024 we plan to publish micro-books each month here that will eventually turn into ebooks, print books, and audiobooks.
Being a Ruckus Maker means you want to Do School Different™ 🔮
Starting with an intentional entry plan is a great way to do just that.
Now, here’s to Making a Ruckus 🥊
Introduction: Better Than Fantasy
It happened every year like clockwork.
July was incredible. Sometimes I slept in, or I got up early to go on a run and then relax with a cup of coffee. I caught up on my favorite science fiction/fantasy book series and met my wife at her office for lunch.
I went into the school a couple times a week to interview new staff, create our master schedules, and take care of logistical operations. There were the annual back-to-school professional development (PD) days to organize and lead and new teacher orientation meetings to plan. But for the most part, July felt like a much-needed escape.
Until August.
I felt it creeping up on me as I watched the calendar days disappear one after the other. The anxiety. I tried to ignore it for as long as possible, pushing off that inevitable day in mid-August when I would be overloaded and overwhelmed with a mile-long list of issues and to-dos that all needed to get done yesterday.
The first day of school always seemed to come sooner than I was ready for.
Don’t get me wrong; there was excitement, too. I couldn’t wait to see the kids and my staff (most of them, anyway). I looked forward to getting everyone else excited about the start of school. I lived off of their enthusiasm, trying to soak up enough energy and momentum to get me at least to winter break without burning out.
Why did it seem like something always went wrong at the start of the new school year? There was always a medical emergency, a discipline issue, a district miscommunication, an angry parent, a bus schedule off track. With having to put out fires from the get-go, I felt off-balance right from the start. I just hoped I could make it through the first 90 days without collapsing.
The truth is, I was never really ready for the beginning of a new school year. No one taught me how to prepare myself for it. There were no principal PD days to attend, no principal handbook I could read that would give me the play-by-play for getting the school year off to a good start. Once I became a principal, it was sink or swim. And for many years, I sank.
I’m guessing you’ve been there, too.
Every school leader hopes for the best at the start of the school year. If you’re an optimist like I am, you probably view those first 90 days as a fresh start, a chance for everything to go right. You envision students walking (not running, like my middle schoolers did) calmly to their classrooms, teachers getting along and turning in grades on time, parents showering you with flowers as you walk into the building…Ok, maybe not that. We’ll leave the fantasy to the pros.
But you definitely don’t envision the chaos that always sneaks its way into the school building every year. You hope and say a prayer and dive back into The Hitchhiker’s Guide to the Galaxy, wondering in the back of your mind if you could hitchhike your way back to July.
The Problem With Hope Alone

The problem we all discover very quickly each year is that hope is not a strategy. That saying is cliché for a reason. It’s true: Hope helps us when we’re communicating our vision for the future and creating a culture that people want to be a part of (We’ll talk about that more in Parts 3 and 4). And hope is the birthplace of ideas. But hope can’t prevent the last-minute mix-ups or kids getting sick in the hallway trashcan or a particularly bad summer slide of kids’ learning retention.
I like to tell leaders: “Ideas are great, but not the greatest.”

What’s better than an idea? Action.
Hope without action is meaningless.
The good news is that hope is not the only tool available to you.
No, you probably didn’t receive a lot of training for your current role. You might not feel supported or prepared for the task ahead of you. You might think it’ll take years to adjust to the back-to-school rhythm and be able to pull it off successfully. But here’s the thing: You’re not alone, you’re more ready than you think you are, and you don’t have to wait years before you can head into a new school year with confidence and clarity.
In this 2-part series, I’m going to show you how to eliminate the back-to-school anxiety by creating the perfect 90-day entry plan for success and executing it with style.
The Perfect 90-Day Entry Plan
Imagine that instead of the first day of school feeling like a runaway train headed toward disaster (and you’re just praying it doesn’t go off the rails), you could start the school year feeling ready and confident to handle whatever comes your way. Imagine that your staff and students were clear on expectations and knew exactly how they could contribute toward helping the school meet its goals.
Imagine that the peace and authentic joy you felt in July didn’t stop on August 1. Imagine that you had enough time and space to keep reading your favorite book during the school year.
This is possible with the right kind of entry plan.
We usually think of entry plans as tools for principals who are new to a school—their own, self-guided “new principal orientation” to help them get settled in a new building with new teachers and students.
And they are.
But I believe every principal should have an entry plan that they can use every year, no matter how long they’ve been leading that particular school.
Having a 90-day entry plan will help you:
✔ Get clarity on how you want to start the school year.
✔ Set the tone for the culture that you want to see.
✔ Create meaningful relationships with your colleagues.
✔ Learn how to communicate more effectively.
✔ And get more done in 90 days than your colleagues get done in a year.
Let’s look at a quick example of how one principal got off the merry-go-round of chaos and started down a calmer, more strategic path. John Unger is the principal at West Fork Middle School in West Fork, Arkansas. For several years, back to school was a hectic time. He and his leadership team tried to stay organized by holding countless meetings and creating detailed agendas—sometimes up to 15 pages long!—but still felt they lacked focus.
John was up at night with worries like, Who’s in charge of what? What are our office manager’s duties? Does everyone have their agendas? Is the schedule ready? Then, when school actually started, he and his team quickly became distracted extinguishing fires and handling logistical issues that came up.
While listening to the Better Leaders Better Schools™ podcast one summer, John heard about the Back-to-School Challenge I was hosting for which the goal was to create a 90-day entry plan to start the year off well. He joined the Ruckus Maker Nation online community to participate in the five-day challenge. His number one goal was to learn how to focus his team on doing the right work at the right time.
Throughout the challenge, John learned about the five buckets of the plan, which helped him think more strategically about how to organize and streamline his team’s efforts in those first 90 days. We’ll learn more about John’s story, but first, let’s learn more about how the plan is organized.
The 5 buckets
There are five categories, or buckets as I call them, that you’ll want to think about while we’re creating your 90-day entry plan for the start of the school year. These five buckets will be the topics of the book’s parts:
You—yes, you!
Leaders usually plan for themselves last, if they plan for themselves at all. Unfortunately, this self-sacrifice is praised and rewarded in our systems. Your tendency to put yourself last is likely what got you into your leadership role. But it’s not going to sustain you or your school. If you are burning out under stress, you won’t be able to serve the people in your school community. You cannot give from an empty cup.
So in this book, we’re not leaving self-care up to chance. Your plan to take care of yourself is integral to achieving success in the first 90 days. We’re going to make a plan for you first. We’ll also talk about how to refine the values that define your leadership, how to avoid your idea enemies, and how to show up the way you want to for the people in your school community.
Communication
After carefully planning how you want to show up as a leader, we will look at your communication systems next because, without thoughtful and intentional planning for communication, nothing else you try to accomplish in the first 90 days will be successful.
Academics
Learning is the business of school; it’s what we’re here to facilitate for our students. Yet there are so many ways learning happens. If we spread our attention and effort too thin across all of the possible areas that could be improved, we won’t make an impact anywhere.
Here I will guide you through a process of inquiry to help keep you and your team focused on the improvements that will have the greatest impact.
Culture
Often, the first 90 days of school are so filled with logistical worries and problem-solving that we neglect to think about the intangibles: the energy and feel of the school as well as the health and safety of the learning environment. We focus on the alligator closest to the boat and hope that when we fix that problem, everything else will fall into place.
Hopefully you’re seeing a pattern here. Nothing happens by chance—even our school’s culture; we have to thoughtfully plan for it. I believe in visualization and meditation—two important tools that help us create a vision and goals for our schools. In Part 4 of this series, we’ll discuss how to employ them to establish priorities and foster a healthy school environment.
Operations
Most school leaders are tempted to focus on operations first—the schedules, policies, facilities, and procedures—but you’ll notice that in our 90-day plan, operations comes last. Yes, operations is the setting in place of systems for the first four buckets, but without knowing what those buckets are, you can’t establish your systems.
In Part 5 of this series, we can start to pay attention to the logistical issues and make a plan for solving problems when they arise.
Finally, in Part 6 of this series we’ll bring together all of the ideas from the first five parts to give you a template you can use to create your own perfect entry plan.
Why 90 Days?
Ninety days works because it’s not so far into the future that you can procrastinate and avoid taking action. It’s also not so soon that you’ll think your plan is unrealistic. It’s just the right length for you to start to see real measurable progress right away.
What I’ve found from coaching hundreds of school leaders like you through this plan is that 90 days is the perfect amount of time to get to work and do something special. Don’t believe me? Test it out. Verify the claim for yourself.
So, Ruckus Maker, what do you say?
I can’t promise it’ll be better than the fantasy book you’ve been eyeing on your bookshelf. But I can promise this story has a happy ending.
Are you ready?
Let’s get started.
Take Action: Your Day 91 Vision
Before you start your 90-day plan … take some time today to think and write about this prompt:
Imagine it’s Day 91 into the new school year, and you’ve executed on the plan we’re creating in this book.
You’re thrilled with the progress that you see around you. What does that progress look like in your school? How are you measuring it?
Bring Your Best Self to School
How often did you eat lunch last school year?
And I don’t mean the times you scarfed down a microwaved burrito while answering emails or running from one building to the other. I mean, how often did you sit down (ideally outside) to eat a healthy meal without any distractions or outside responsibilities weighing on you?
If you roll your eyes or laugh out loud at the idea of being able to eat that kind of lunch, this part is for you. Because you deserve to eat a lunch like that every single day.
Of course, this isn’t just about lunch. The time and space you have to eat lunch is indicative of the overall margin you have in your work life and the stress you might be experiencing at school.
EdSurge reported that the mental health and wellbeing of principals has been particularly low since the onset of the COVID-19 pandemic (Sullivan, 2022). And a 2022 study conducted by the RAND Corporation found that 85 percent of principals report experiencing job-related stress. (Steiner et al., 2022).
But I don’t need to tell you that. You see it everyday. Forget about lunch; we’re barely sleeping and making it through the day!
It’s easy for us to excuse the amount of stress on our shoulders; we think about the mile-long list of things that need to get done and the constant demands on our time. Shouldn’t the other people in our school building come first?
Of course we have to think about the other people in our buildings. In the foreword to Simon Sinek’s 2014 book Leaders Eat Last, Lieutenant General George J. Flynn wrote, “Great leaders truly care about those they are privileged to lead and understand that the true cost of the leadership privilege comes at the expense of self-interest” (p. xii).
Sinek wrote his book in response to the cultural lack of trust he saw in the businesses he worked with. Over and over again, he saw leaders take advantage of others and prioritize themselves over the people they were supposed to be serving.
That’s not the problem I see in schools. I see, and the research agrees, that we have the opposite problem in education. Leaders are burning out and leaving schools at an alarming rate, not by choice but for the sake of pure survival. That constant churn—the continual turnover of leadership—is harmful to our schools. Not to mention, it’s harmful to you.
I know, I know, you picked up this book to create a 90-day entry plan for your school. But I’ve learned over several years of helping Ruckus Makers like yourself that if you are not healthy, your school won’t be healthy. This is why the motto for Better Leaders Better Schools™ is “When YOU get better, everyone wins.”
The most neglected factor of school success is you. When school starts, it’s easy to get sidetracked by all of the other buckets that feel more important and more urgent than taking care of ourselves.
So in this part, we’ll talk about how you can plan to show up as your best self in the first 90 days.
The Ruckus Maker Mindset Tool
In 2018, John Antulov was waiting for his wife, Trish, to come home. Trish was the principal of a school in Perth, Australia, and it wasn’t uncommon for her to stay late into the evenings to get work done. He wasn’t too worried about it until she missed his phone calls. That was unlike her. By 10 p.m., John was seriously concerned, and he went to the school to check on her.
He found that his wife Trish had died at her desk (Hiatt, 2018).
This is a dramatic and, thankfully, uncommonly tragic story. But it’s a good cautionary tale for all of us who want to be around for a long time to serve our school communities.
Ruckus Makers want to be top performers, and all top performers work hard. That’s a fact. But the best top performers know how to recuperate and rest as well so that they can put in the hard work.
I like to use a simple self-evaluation with the leaders I coach to help them prioritize their mental and physical health. The Ruckus Maker Mindset Tool™ looks at five key indicators:
● Eating, because, like any high performer, you need to be putting the right fuel in your body;
● Sleeping, because our bodies need time to rest and recharge for optimal performance;
● Moving, because it’s easier to maintain momentum when we move consistently;
● Meditating, because our minds need time and space to process information and function optimally; and
● Unplugging, because it’s hard to do any of the above things if we’re being constantly interrupted.
On a scale of 1 to 5—with 1 being “This area in my life sucks right now,” and 5 being “I am rocking this area!”—rate yourself in each domain:
Eating: ____
Sleeping: ____
Moving: ____
Meditating: ____
Unplugging: ____
If you’re reading this before the start of the school year (as I hope you are!), then I hope that you’re doing great in all five of these domains. But if you’re struggling before the school year has even started, that’s an indicator that this area of your life needs your full attention now before the busyness of school begins.
Take a few minutes to brainstorm specific ways you can take care of yourself in each of these domains. Here are some questions to reflect on:
Eating:
● What kinds of snacks can you eat throughout the day?
● When will you eat lunch?
● What will you eat for lunch?
● How will you prepare food so that you’re able to eat consistently nutritious meals?
Sleeping:
● What time will you start getting ready for bed?
● What routines and rituals can you establish to prepare for sleep?
● What time do you want to wake up in the morning?
Moving:
● What are your favorite types of movement?
● How can you find time to move throughout the day at school?
● What kinds of exercise can you incorporate into your weekly routine?
Meditating:
● When is the best time for you to meditate?
● Where can you meditate that is quiet and free of distractions?
● Will you use guided meditations, music, or silence to help you quiet your mind?
Unplugging:
● Where will you keep your phone while you unplug?
● What steps can your faculty and students take before trying to reach you?
● Who can be a point of contact for you while you’re unplugging?
Practice the 85% Rule
Olympic runner Carl Lewis famously took a counterintuitive approach to winning the 100-meter dash. Unlike his competitors, Lewis held back at the beginning of the race, often trailing the other runners at the 40-meter mark. But as their energy began to flag in the last half or quarter of the sprint, Lewis maintained a consistent pace and managed to come in first, winning nine Olympic gold medals with what would become known as the 85% rule. Inc. contributor Jeff Haden (2020) wrote that Lewis trusted “that preparation and technique—not ‘extra’ effort in this moment—would pay off.”
Practicing the 85% rule means that, at all times, you’re consistently using just 85% of your energy. The hardest part about this is learning to hold back, even when you could give more. It feels awkward, uncomfortable, frustrating, even morally wrong at times—but it is the best strategy for consistently contributing with excellence and avoiding the danger of burning out.
Once you get in the habit of taking care of yourself so you can bring your best self to school, you can begin thinking about what actions you want to take and how the people in your building will experience you. We do that by defining our sticky core values and getting to know our idea enemies.
Define Your Sticky Core Values
Every leader should live by what I call sticky core values. These are ideas that guide our actions and decisions from day to day.
When we think of values, we tend to think of words like honesty, integrity, excellence, and dedication. Obviously, these are admirable qualities to hold. The problem with general terms like these, however, is that they don’t provide a lot of guidance for our everyday actions.
A more powerful approach to defining values is to embrace memorable phrases that illustrate how you want to show up as a leader in your community every day. Here are my sticky core values to give you an idea:
Turn Pro
In everything I do, I want to show up to do my best, no matter how I feel. I put aside my complaints and focus on the job in front of me because that’s what the pros do. According to author Steven Pressfield, this is the only way to beat what he calls The Resistance and what you may know as imposter syndrome.
Purple Cow
This is an idea from a book by Seth Godin (2004) of the same title: Purple Cow: Transform Your Business by Being Remarkable. I grew up driving the incredibly boring interstates in Illinois. There’s nothing to see along these highways but cornfields and cows. And there are only two kinds of cows in Illinois: brown and white, or black and white.
Imagine, though, that you were driving along one day and saw a purple cow! You’d never forget it, right?
What’s more—you’d tell everyone else about it.
My purple-cow value encourages me to seek out and create extraordinary experiences that others will never forget and that they will want to share with everyone they meet.
Ripple Effect
My focus is on long-term impact. I want my actions to have positive consequences not just now, but long into the future. I believe that small changes add up to big results over time. Therefore, in my decision making, I’m always asking myself what the ripple effects of this decision will be.
Forest From the Trees
I try to maintain a long-term perspective, which helps me with my ripple-effect value as well. It’s easy to get caught up in minutiae, but I challenge myself to see the big picture of any situation.
Sponge That Scales
The idea of being a lifelong learner is a nice buzzword in education, but like all buzzwords, it tends to lose its value and meaning over time. Instead, I like the idea of being a sponge that scales because as I learn, my impact and influence grows. Like a sponge, I expand. This value not only tells me that I should be learning, but that I should be using and applying what I learn.
What are your sticky core values?
Know Your Idea Enemies
Your enemies are not the people you interact with; they’re the ideas that hold you back. Think of them as the opposites of your sticky core values. These are the ideas that prevent you from making good decisions and showing up as your best self.
My enemies are:
Status Quo
Traditions can be good and useful, but often, they hold me back. I never want to let inertia or “the way we’ve always done things” keep me from innovating or creating those purple-cow experiences.
Stagnation
I think of stagnation as a lack of desire to learn and get better. Often I use busyness to productively procrastinate on the real work I should be doing, the work of learning and growing. Ironically, stagnation can be the highest in those who look like they’re doing the most.
Isolation
Working and trying to lead on my own is a recipe for low performance. Business coach and author Greg Salciccioli (2011) says that isolation is the number one enemy of excellence. No one can get better in a vacuum.
Lack of Mentorship
I believe I need people who are at least 10 percent ahead of me to help me get where I want to go. Without that mentorship and guidance, I flounder. This enemy is one of the core reasons I’ve created the Better Leaders Better Schools™ administrator masterminds—so that leaders will never be without a mentor. I also make it a habit to surround myself with good mentors.
Open-Door Policies
While it’s important to be available and present to the people in my school (and we’ll discuss this more in Part 4, having an open-door policy is a terrible idea! Why? Because it invites distraction.
Most leaders with an open-door policy say something to the effect of: “People over paperwork.” But what they really mean is: “I prioritize people over paperwork while at school. By doing so, however, I prioritize my work over time for myself and time for my family because I believe work is more important.”
Ouch.
I cannot take care of myself when I am constantly distracted.
You might have similar enemies in your life, or you may encounter others. Your enemies might change over time. But know them and study them so that you’re ready to do battle with them when they arise.
Take Action: Your Sticky Core Values
What are five phrases that describe how you want to show up at school? You might find inspiration for your sticky core values in books or from mentors in your life.
What you stand for is important, but at times, knowing what you stand against can be even more impactful. What are the five idea enemies you want to avoid?
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