Principal Matters: The School Leader's Podcast with William D. Parker

MONDAY MATTERS with Jen Schwanke and Will Parker – First Day of School Reminders

18 min · 3. Aug. 2026
Episode MONDAY MATTERS with Jen Schwanke and Will Parker – First Day of School Reminders Cover

Beschreibung

FIRST DAYS OF SCHOOL REMINDERS William D. Parker This post is reprinted from an archived one we shared in 2019. Jenny is a returning student at her high school. She has a part-time job, which keeps her up late most nights. When she arrives late to school, she has already missed breakfast, and she’s tardy. She stands in a long line at the counseling office until she is given her class schedule. She reads it quickly: First hour, Mr. Samuels, room 125, Algebra II. She doesn’t recognize the name. Maybe he’s one of the new teachers. She heads down the hall. She’s flush with frustration but holds her head high, turns the corner, and steps into the classroom. She finds an open seat in the back of the room. As she glances around the room, she does not see the teacher’s name anywhere. By this time, she’s too embarrassed to ask, and the teacher is so involved in his first-day-of-school speech that he hasn’t paused to ask Jenny for her name or schedule or given her any other leads. As he talks on, she realizes this is Language Arts, not a math class. She must have entered the wrong room or misread her schedule. Jenny endures the discomfort for the remaining minutes. Then she rushes from the class as quickly as possible, frustrated and hoping the rest of her first day of school is not this confusing. KEEPING STUDENTS IN MIND As important as it is to keep your responsibilities in mind as you start a new school year, it is even more important to keep the end goal in mind: serving students. You have students returning from all kinds of backgrounds and experiences. You also serve teachers, staff, and parents with questions and concerns. How can you be ready for all of them? QUESTIONS EVERY STUDENT IS ASKING ON THE FIRST DAY As you know, how we prepare for students can either help or hurt their first-day experiences. Harry Wong, author of The First Days of School: How to Be an Effective Teacher, reminds us of seven questions every student asks about his or her teachers: 1. Am I in the right room? 2. Where am I supposed to sit? 3. Who is the teacher as a person? 4. Will the teacher treat me as a human being? 5. What are the rules in this classroom? 6. What will I be doing this year? 7. How will I be graded? QUESTIONS EVERY TEACHER AND STAFF PERSON ASKS ON THE FIRST DAY But students aren’t the only ones who need clarity. Your teachers and staff also want answers to some questions that only school leaders can answer. So, I’ve rewritten Harry Wong’s questions to reflect what your teachers and staff will be asking: 1. What is my schedule? 2. What extra duties, assignments, or activities might I expect? 3. Who is my administrator as a person? 4. Will he or she treat me as a human being? 5. What are the expectations, procedures, and policies in our school? 6. What am I expected to accomplish this year? 7. How will I be evaluated, mentored, graded, or coached? TIPS FOR SCHOOL LEADERS PREPARING FOR SCHOOL With those thoughts in mind, in this week’s Principal Matters podcast, co-host Jen Schwanke and I share six ideas to keep in mind when preparing for the start of school. Listen to the podcast version for even more stories and takeaways. 1. BUILD AND REBUILD RELATIONSHIPS As teachers, staff, or parents return to your building, how are you reconnecting with them? Whether it’s hearing about summer trips, family updates, or meaningful moments in their lives, these conversations are important for building trust. They also open questions your teammates may have that are important for you to answer before school begins. 2. USE TECHNOLOGY AND SOCIAL MEDIA Jen likes to schedule several reminders to her community through social media that she posts throughout the summer. Whether you are using your school website, school-wide communication apps, or social media, share important announcements and reminders several times throughout the summer to set expectations for the new school year. 3. ORGANIZE AND MANAGE—REMEMBER EVERYTHING! Obviously, no system is perfect, but as you move into a school year, it is important to keep a list of to-dos for your team and yourself. One way to do this is to maintain a list as you start the year that you can use again the following year or years. Go through last year’s calendar to see if you’re missing anything. Rely on a team—secretaries, assistants, and lead teachers—who can help you stay on track. 4. DEFINE RESPONSIBILITIES Sometimes principals have well-defined expectations for teachers but forget about non-instructional staff. Consider working with each staff member on well-defined key responsibility areas. You can learn more and see samples in previous posts. With teachers and staff, don’t be afraid to say what is expected and provide it in writing. 5. MANAGE HIGH ANXIETY Everyone is anxious, in good or bad ways, about the start of school. They are looking to the principal to set the tone. Manage the high anxiety by demonstrating a sense of calm and reassurance. One way to do this is by including celebration in your welcome back. Provide lunch, give them a gift, communicate positivity, and reassure them again and again that it will be a great year and all will be well. 6. HOST ORIENTATION MEETINGS New teachers, returning teachers, new students, returning students, and new parents—you will have several groups who need to be welcomed in orientation meetings. Each group will have different needs, but the goals are the same: communicate expectations, be positive, and be available to answer questions. ADDITIONAL CHECKLISTS FOR THE SCHOOL LEADER’S FIRST DAYS OF SCHOOL Here are some additional questions to ask as you start the school year: * Have you posted “Welcome Back” signage? * Have you included maps of your school for new students? * Is signage clear and visible throughout the building? * Have you shared master schedules in advance with teachers? * What are your established arrival and departure routines? * Did you update and plan for consistently implemented policies and procedures? * Have parents and students been invited to an orientation or open house before school? * Is your school website updated with current calendars, a welcome-back message for parents, and key information they should know? * Have you updated and shared duty rosters, activities, and/or game calendars for teachers? * Does your own calendar include dates for state reports, observations, evaluations, and team meetings? LET’S WRAP THIS UP Think through your school-wide processes from the fresh perspective of a student, parent, or teacher, and then decide what steps to take moving forward so that everyone in your school or organization has clarity on what to expect. Most importantly, remember that creating the best “first days” for students and staff also means realizing your school members need many of these questions answered every day. The post MONDAY MATTERS with Jen Schwanke and Will Parker – First Day of School Reminders [https://williamdparker.com/2026/monday-matters-with-jen-schwanke-and-will-parker-first-day-of-school-reminders/] appeared first on Principal Matters [https://williamdparker.com].

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Episode MONDAY MATTERS with Jen Schwanke and Will Parker – First Day of School Reminders Cover

MONDAY MATTERS with Jen Schwanke and Will Parker – First Day of School Reminders

FIRST DAYS OF SCHOOL REMINDERS William D. Parker This post is reprinted from an archived one we shared in 2019. Jenny is a returning student at her high school. She has a part-time job, which keeps her up late most nights. When she arrives late to school, she has already missed breakfast, and she’s tardy. She stands in a long line at the counseling office until she is given her class schedule. She reads it quickly: First hour, Mr. Samuels, room 125, Algebra II. She doesn’t recognize the name. Maybe he’s one of the new teachers. She heads down the hall. She’s flush with frustration but holds her head high, turns the corner, and steps into the classroom. She finds an open seat in the back of the room. As she glances around the room, she does not see the teacher’s name anywhere. By this time, she’s too embarrassed to ask, and the teacher is so involved in his first-day-of-school speech that he hasn’t paused to ask Jenny for her name or schedule or given her any other leads. As he talks on, she realizes this is Language Arts, not a math class. She must have entered the wrong room or misread her schedule. Jenny endures the discomfort for the remaining minutes. Then she rushes from the class as quickly as possible, frustrated and hoping the rest of her first day of school is not this confusing. KEEPING STUDENTS IN MIND As important as it is to keep your responsibilities in mind as you start a new school year, it is even more important to keep the end goal in mind: serving students. You have students returning from all kinds of backgrounds and experiences. You also serve teachers, staff, and parents with questions and concerns. How can you be ready for all of them? QUESTIONS EVERY STUDENT IS ASKING ON THE FIRST DAY As you know, how we prepare for students can either help or hurt their first-day experiences. Harry Wong, author of The First Days of School: How to Be an Effective Teacher, reminds us of seven questions every student asks about his or her teachers: 1. Am I in the right room? 2. Where am I supposed to sit? 3. Who is the teacher as a person? 4. Will the teacher treat me as a human being? 5. What are the rules in this classroom? 6. What will I be doing this year? 7. How will I be graded? QUESTIONS EVERY TEACHER AND STAFF PERSON ASKS ON THE FIRST DAY But students aren’t the only ones who need clarity. Your teachers and staff also want answers to some questions that only school leaders can answer. So, I’ve rewritten Harry Wong’s questions to reflect what your teachers and staff will be asking: 1. What is my schedule? 2. What extra duties, assignments, or activities might I expect? 3. Who is my administrator as a person? 4. Will he or she treat me as a human being? 5. What are the expectations, procedures, and policies in our school? 6. What am I expected to accomplish this year? 7. How will I be evaluated, mentored, graded, or coached? TIPS FOR SCHOOL LEADERS PREPARING FOR SCHOOL With those thoughts in mind, in this week’s Principal Matters podcast, co-host Jen Schwanke and I share six ideas to keep in mind when preparing for the start of school. Listen to the podcast version for even more stories and takeaways. 1. BUILD AND REBUILD RELATIONSHIPS As teachers, staff, or parents return to your building, how are you reconnecting with them? Whether it’s hearing about summer trips, family updates, or meaningful moments in their lives, these conversations are important for building trust. They also open questions your teammates may have that are important for you to answer before school begins. 2. USE TECHNOLOGY AND SOCIAL MEDIA Jen likes to schedule several reminders to her community through social media that she posts throughout the summer. Whether you are using your school website, school-wide communication apps, or social media, share important announcements and reminders several times throughout the summer to set expectations for the new school year. 3. ORGANIZE AND MANAGE—REMEMBER EVERYTHING! Obviously, no system is perfect, but as you move into a school year, it is important to keep a list of to-dos for your team and yourself. One way to do this is to maintain a list as you start the year that you can use again the following year or years. Go through last year’s calendar to see if you’re missing anything. Rely on a team—secretaries, assistants, and lead teachers—who can help you stay on track. 4. DEFINE RESPONSIBILITIES Sometimes principals have well-defined expectations for teachers but forget about non-instructional staff. Consider working with each staff member on well-defined key responsibility areas. You can learn more and see samples in previous posts. With teachers and staff, don’t be afraid to say what is expected and provide it in writing. 5. MANAGE HIGH ANXIETY Everyone is anxious, in good or bad ways, about the start of school. They are looking to the principal to set the tone. Manage the high anxiety by demonstrating a sense of calm and reassurance. One way to do this is by including celebration in your welcome back. Provide lunch, give them a gift, communicate positivity, and reassure them again and again that it will be a great year and all will be well. 6. HOST ORIENTATION MEETINGS New teachers, returning teachers, new students, returning students, and new parents—you will have several groups who need to be welcomed in orientation meetings. Each group will have different needs, but the goals are the same: communicate expectations, be positive, and be available to answer questions. ADDITIONAL CHECKLISTS FOR THE SCHOOL LEADER’S FIRST DAYS OF SCHOOL Here are some additional questions to ask as you start the school year: * Have you posted “Welcome Back” signage? * Have you included maps of your school for new students? * Is signage clear and visible throughout the building? * Have you shared master schedules in advance with teachers? * What are your established arrival and departure routines? * Did you update and plan for consistently implemented policies and procedures? * Have parents and students been invited to an orientation or open house before school? * Is your school website updated with current calendars, a welcome-back message for parents, and key information they should know? * Have you updated and shared duty rosters, activities, and/or game calendars for teachers? * Does your own calendar include dates for state reports, observations, evaluations, and team meetings? LET’S WRAP THIS UP Think through your school-wide processes from the fresh perspective of a student, parent, or teacher, and then decide what steps to take moving forward so that everyone in your school or organization has clarity on what to expect. Most importantly, remember that creating the best “first days” for students and staff also means realizing your school members need many of these questions answered every day. The post MONDAY MATTERS with Jen Schwanke and Will Parker – First Day of School Reminders [https://williamdparker.com/2026/monday-matters-with-jen-schwanke-and-will-parker-first-day-of-school-reminders/] appeared first on Principal Matters [https://williamdparker.com].

3. Aug. 202618 min
Episode PMP511: Creating a Greenhouse Culture with Mike Hayes & Ashley Pacholewski Cover

PMP511: Creating a Greenhouse Culture with Mike Hayes & Ashley Pacholewski

A QUICK NOTE TO LISTENERS: Before this week’s interview, Will Parker takes some time to ask Jen Schwanke about recording an audio book version of her book, You’re the Principal Now What? Here is a link to purchase the book! https://www.echopointbooks.com/cart/add/?id=45972673560749&quantity=1 [https://www.echopointbooks.com/cart/add/?id=45972673560749&quantity=1] Use code PRINCIPAL30 for a 30% discount!  Follow this 30-second demo [https://demo.storylane.com/share/eas3aljwtrmh] to learn how to use the code.  Bulk pricing is available too! Contact sales@echopointbooks.com for special bulk pricing to gift this resource to your entire team!  MEET MIKE HAYES & ASHLEY PACHOLEWSKI: [https://williamdparker.com/wp-content/uploads/2026/07/PMP-Template-36-1024x1024.png] Mike Hayes serves as Assistant Superintendent of Aurora City School District in Northeast Ohio. Previously, he was principal of Aurora High School—known as “The Greenhouse”—and earlier served as an assistant principal and administrator in the Cincinnati/Dayton area. He began his career as a secondary language arts teacher. An Aurora resident, Mike holds a leadership certificate from Harvard University, an M.Ed. from Xavier University, and a B.A. from The Ohio State University. He is currently pursuing a Ph.D. in Educational Leadership at University of Dayton. Mike is passionate about growth, optimism, and courageous leadership. He believes in dreaming boldly, embracing vulnerability, and choosing to see the best in others while fully engaging in the life right in front of us. Dr. Ashley Pacholewski (Pach) serves as Principal of Aurora High School, “The Greenhouse,” in the Aurora City School District. Previously, she was an assistant principal at Ashland Middle School and began her career teaching English language arts and serving as an instructional coach at Brunswick High School. She earned her undergraduate degree from Bowling Green State University, her M.Ed. and reading certification from Cleveland State University, and her Ed.D. from Ashland University. Ashley is passionate about creating a culture of curiosity, connection, and joy—empowering teams to take risks, collaborate meaningfully, and support students as whole learners. CREATING A GREENHOUSE CULTURE: In this week’s episode of Principal Matters, Dr. Jen Schwanke hosts a “full circle” conversation with Ashley Pacholewski, the first female principal in the history of Aurora High School, and Mike Hayes, Assistant Superintendent of Aurora City Schools. The discussion centers on the “Greenhouse” culture of their district—a nickname for their school, but also a metaphor for the school’s  nurturing environment where leadership is shared and growth is continuous. Mike describes the intentionality behind the transition to Ashley’s leadership, which was designed to ensure that the new leader wasn’t just a fit for the existing culture but had the authenticity to make it even better. Ashley reflects on her first year, emphasizing the profound impact of being given permission to enjoy her first year.  She describes a leadership style rooted in authenticity and gratitude, where she brings her whole self to the job—symbolized by the mason jar bouquets from her own garden that she leaves for staff. The support between Mike and Ashley serves as a model for effective mentorship; it is built on scheduled bi-weekly check-ins, generous assumptions of positive intent, and a lack of ego, allowing Ashley the space to lead without the weight of top level pressure. THE POWER OF PERMISSION: A successful transition starts when veteran leadership gives the new leader explicit permission to enjoy the role and focus on relationship-building rather than just immediate data or achievement. It also involves staff in reflecting on how they can support the incoming leader, creating a sense of shared ownership in the new principal’s success. PROFESSIONAL RESPECT: Shift leadership vocabulary from “top-down” praise to “side-by-side” validation. Using language that honors the person (e.g., “You are inspiring”) rather than the leader’s reaction to them (e.g., “I am inspired by you”) fosters true professional respect. STRESS IS GOOD: Growth requires a certain amount of stress. Effective leaders don’t just clear the path; they provide the support systems that allow individuals to develop the strength to handle challenges. CULTURAL GRATITUDE: Small, authentic gestures are not “extras”; they are essential seeds of trust that define the building’s climate. The interview concludes with a powerful outlook on the future of school leadership as an infinite game. Mike shares a poignant analogy about the importance of wind in a biodome, noting that leaders should not seek to remove all obstacles, but rather help staff and students grow the resilience needed to withstand them. By focusing on intentional language and prioritizing collaborative learning over mandates, the Aurora team demonstrates how a heart-centered, value-driven approach creates a thriving educational ecosystem. The post PMP511: Creating a Greenhouse Culture with Mike Hayes & Ashley Pacholewski [https://williamdparker.com/2026/pmp511-creating-a-greenhouse-culture-with-mike-hayes-ashley-pacholewski/] appeared first on Principal Matters [https://williamdparker.com].

29. Juli 202645 min
Episode MONDAY MATTERS with Jen Schwanke and Will Parker – Book Talk Cover

MONDAY MATTERS with Jen Schwanke and Will Parker – Book Talk

In this week’s Monday Matters episode, Jen and I grabbed four of the last books we’ve read, and shared a few takeaways from each for listeners looking for good reads this summer: WILL’S LIST: The Lion Women of Tehran [https://www.simonandschuster.com/books/The-Lion-Women-of-Tehran/Marjan-Kamali/9781668036594] by Marjan Kamali A compelling novel tracing the history of Iran from the 1970s through the Revolution and into modern times through the lives of two lifelong friends. A Very Small Farm [https://www.oupress.com/9780806184128/a-very-small-farm/] by William Paul Winchester One of my favorite winter reads when I’m longing to be in the garden. It’s a thoughtful memoir about restoring a small homestead and finding joy in simple living. Into the Wild [https://www.penguinrandomhouse.com/books/288292/into-the-wild-by-jon-krakauer/] by Jon Krakauer The first time I’d read it. Equal parts wanderlust and cautionary tale, with Krakauer telling the tragic story Christopher Johnson while weaving in his own stories of nearly dying in the wilderness. Playground [https://www.richardpowers.net/playground/] by Richard Powers Powers has a remarkable way of writing epic novels that make you care deeply about the natural world. This one will leave you thinking about the oceans long after you’ve finished it. JEN’S LIST: This Is Not About Running [https://www.harpercollins.com/products/this-is-not-about-running-mary-cain] by Mary Cain A powerful memoir from the former elite runner about identity, resilience, and reclaiming her life after experiencing abuse within professional athletics. Paper Girl [https://www.penguinrandomhouse.com/books/182367/paper-girl-by-beth-macy/] by Beth Macy A memoir highlighting the value and importance of education in rural communities, told through the eyes of an award-winning journalist. If you enjoy it, also check out Dopesick. Still Writing [https://danishapiro.com/books/still-writing/] by Dani Shapiro An inspiring reflection on the creative life and the importance of continuing to make art, even through uncertainty. Awake [https://www.jenhatmaker.com/books/awake] by Jen Hatmaker A thoughtful memoir about rebuilding a life, embracing change, and discovering that it’s okay to change your mind. Joyride [https://www.susanorlean.com/books/joyride/] by Susan Orlean A collection of essays that reminds us no story is ever as simple as it first appears. Reading it led me to Saturday Night, The Orchid Thief, and Rin Tin Tin. NOW IT’S YOUR TURN: What books are you reading? We’d love to add them to our own lists! The post MONDAY MATTERS with Jen Schwanke and Will Parker – Book Talk [https://williamdparker.com/2026/monday-matters-with-jen-schwanke-and-will-parker-book-talk/] appeared first on Principal Matters [https://williamdparker.com].

27. Juli 202618 min
Episode PMP510: Redefining Leadership Through Relational Intelligence with Brad Johnson and Rachel Edoho-Eket Cover

PMP510: Redefining Leadership Through Relational Intelligence with Brad Johnson and Rachel Edoho-Eket

A QUICK NOTE TO LISTNERS: Before this week’s interview, Will Parker and Jen Schwanke take some time to answer a listener question. This week’s question is:  I’m thinking about retiring in a year, but I want to do something part time. What are some options you’ve learned about consulting that I might be able to develop for me? Listen in to hear their response! MEET BRAD JOHNSON AND RACHEL EDOHO-EKET: [https://williamdparker.com/wp-content/uploads/2026/07/PMP-Template-35-1024x1024.png] In this episode of Principal Matters, Dr. Schwanke is joined by two heavy hitters in the education world: Dr. Brad Johnson, author of over 20 books including the newly released Coffee with the Custodian, and Dr. Rachel Edoho-Eket, a Blue Ribbon school principal, TEDx speaker, and President of the Maryland Association of Elementary School Principals.  Together, we dive into the core philosophy of their co-authored book, Relational Intelligence. We challenge the outdated “command and control” model of leadership, shifting the focus from technical systems to the human systems that actually drive school success. As we discuss, while strategy is important, it simply doesn’t move the needle if the foundational relationships aren’t in place. EMOTIONAL INTELLIGENCE AND RELATIONAL INTELLIGENCE: In our conversation, we explore the critical distinction between Emotional Intelligence (EQ) and Relational Intelligence (RQ). While EQ helps a leader understand themselves, RQ is what allows them to effectively lead others by navigating the complex web of stakeholders—from students and staff to parents and the central office. Brad and Rachel share practical advice on how busy administrators can prioritize “connection over compliance.” We talk about making “relational deposits,” the power of being vulnerable enough to admit when we don’t have all the answers, and why research shows that RQ is actually a better predictor of leadership success than IQ. THE MILLION DOLLAR QUESTIONS: Finally, we tackle the “million-dollar questions” of school leadership: handling toxic staff members and preventing burnout. Dr. Johnson shares his “HOPE” framework—focusing on Help, Opportunity, Praise, and Encouragement—to flip the script on our natural tendency toward negativity. We wrap up with a look at his narrative approach to leadership in his new book, reminding us that the best insights often come from the most “invisible” people in our buildings. This conversation is a powerful reminder that while your title gives you your position, your relationships are what truly define your impact. STAYING CONNECTED: If you wish to stay connected with the work of Dr. Brad Johnson or Dr. Rachel Edoho-Eket, you can learn about them via the following channels: Dr. Johnson: * Facebook: https://www.facebook.com/drbradjohnson [https://www.facebook.com/drbradjohnson] * Twitter: https://twitter.com/DrBradJohnson [https://twitter.com/DrBradJohnson] * Website: www.DoctorBradJohnson.com [http://www.doctorbradjohnson.com/] Dr. Edoho-Eket: * Website: www.racheledohoeket.com [http://www.racheledohoeket.com/]  * Instagram: https://www.instagram.com/racheledohoeket/ [https://www.instagram.com/racheledohoeket/] * Linkedin: Dr. Rachel Edoho-Eket | LinkedIn [https://www.linkedin.com/in/dr-rachel-edoho-eket-2b0ab7221/] * Twitter: Dr. Rachel Edoho-Eket (@RachelEdohoEket) / X [https://x.com/RachelEdohoEket] * Youtube: https://www.youtube.com/@racheledoho-eket [https://www.youtube.com/@racheledoho-eket] * Amazon: https://www.amazon.com/author/dr.edoho-eket [https://www.amazon.com/author/dr.edoho-eket] Thanks for doing what matters! The post PMP510: Redefining Leadership Through Relational Intelligence with Brad Johnson and Rachel Edoho-Eket [https://williamdparker.com/2026/pmp510-redefining-leadership-through-relational-intelligence-with-brad-johnson-and-rachel-edoho-eket/] appeared first on Principal Matters [https://williamdparker.com].

22. Juli 202651 min
Episode MONDAY MATTERS with Jen Schwanke and Will Parker – Lessons in Sailing Upwind Cover

MONDAY MATTERS with Jen Schwanke and Will Parker – Lessons in Sailing Upwind

LESSONS IN SAILING UPWIND William D. Parker, July 9, 2026 When my friend Dave Sandowich, a retired principal with 20+ years of admin experience, invited me to go sailing with me off the Chesapeake Bay, I was thrilled. This would be the third time he had taken me on the water, and my son Jack, now 20 years old, was coming along. We sailed 60 miles over three days, from Dave’s place on Kent Island to Annapolis, Maryland, and then south to a quiet cove. Sailing upwind was the most challenging and exhilarating part of the trip. Calm waters and quiet moments were nice too, but Dave was quick to point out that sailing upwind takes work – a mastery of understanding the sail and jib, the use of crewmates to help you come about, and knowledge and skill to stay on track. As Dave told me the first time we sailed together in 2019, “Sailing is a lot like leadership,” he said. “On a sailboat your destination may be directly from where the wind is coming from. A sailboat can’t sail directly into the wind but it can work its way up wind by sailing at angles off the wind and working its  way up wind to the destination. It is more work and will take more time but you will get there if you stay the course, apply your sailing knowledge and get the feedback from your instruments and instincts and adjust along the way.” Whenever I think about resistance in leadership, I think about sailing into the wind. Leaders have a destination in sight for their teachers, students and communities. The question is: what do you do when you experience pushback and resistance toward reaching those goals. WHAT HAS FACING RESISTANCE TAUGHT YOU? This week, I met with a group of leaders for a retreat, and I posed that question to them. Some of their responses included: “Pushback causes me to reassess my own understanding of mission and vision and if I’m effectively and clearly communicating it with others.” “Perhaps there is misunderstanding or misrepresentation of our goals that I need to recommunicate.” “It’s my responsibility to realign expectations while keeping in mind that relationships are complex. Reaching my goal may not be a straight shot. Sometimes I have to work with people until they come around to a clearer perspective.” “Leadership is more like chess than checkers. It requires wisdom to know how to maneuver among people and systems while still reaching the right outcome.” Each one of these statements reminds me that the work of leaders is complex, and navigating complexity takes more than just a good handbook or code of conduct. It requires wisdom to step into the complexities and determine the next best step for moving forward. Having said that, here are a few thoughts to keep in mind as you sail a route in the coming school year: 1. People – Investing in people means taking time to know who is on your team, gaining their trust, and remembering that development is not a one time event. 2. Systems – Developing systems means analyzing your operations, processes, routines, and procedures in light of your students, teachers, and community members. Ask yourself what it is like to be on the other side of any activity at your school. How are you aligning the system involved for the outcome you want them to experience? 3. Belief – Encouraging collective efficacy among your team members means being clear on what you believe is most important for the outcomes and impact happening around student learning. These three reminders bring us back to commitments to people, systems, and belief – the essentials for any flourishing school community.  Anyone trying to navigate or move forward an entire organization or community must be prepared to face some winds of resistance. You can either allow the pushback to cause you to throw anchor, drop sails, or turn around.  CHOOSE YOUR HARD Our last day together, Dave and Jack and I were having breakfast together, when I asked Dave what were some lessons in leadership he’s learned along the way. Dave is enjoying retirement and a lot of time on his boat with family and friends. When I asked him what lessons he was learning, he looked at me and Jack and said, “You have to learn to choose your hard.” “What do you mean by that?” I asked. “Take my physical fitness, for example,” he continued. “I choose the hard by keeping my workout routine. I don’t really want to do pullups, planks and pushups, but I choose that hard over the hard of declining health, higher blood pressure, or losing my mobility over time. You choose your hard one way or the other.” Life and leadership teach us a lot of lessons along the way if we slow down enough to listen and reflect. In leadership, the harder and wiser option often requires sailing into the winds of resistance. If it wasn’t hard, everyone would do it by default. But good outcomes often require hard choices.  When I think about the goal of schools to build a community of learning, I’m encouraged that the task is worth it for students, for teachers, and for communities. It’s also worth it for leaders.  On our last day of sailing, Dave navigated the boat back toward Kent Island. He gave each of us a turn at the helm. I tried to soak in the memories of sun, waves, and the warmth of friendship and family.  Your school year ahead will be full of unexpected situations, and the truth is: you don’t choose the winds you encounter. But you can choose how you respond to them.  As you sail into the winds of a new school year, may you learn to pivot, to navigate, and to recalibrate along the way.  The destination and experiences you reach will look different in each journey, but the mindset you have along the way may be what makes all the difference. NOW IT’S YOUR TURN What are some experiences in pushback or resistance you’ve faced, and what lessons did you learn? How can you apply those lessons to navigating with wisdom “upwind” in the school year ahead? The post MONDAY MATTERS with Jen Schwanke and Will Parker – Lessons in Sailing Upwind [https://williamdparker.com/2026/monday-matters-with-jen-schwanke-and-will-parker-lessons-in-sailing-upwind/] appeared first on Principal Matters [https://williamdparker.com].

20. Juli 202615 min