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PODCAST

The Private School Leader Podcast

The Private School Leader Podcast exists to help you go from SURVIVING to THRIVING as you lead your school. Do you ever feel lonely and isolated in your role as a private school leader? Do you wish that you could get back to what really energizes you (making a difference in the lives of your students)? Do you want to have a long AND fulfilling career in private school education? Are you an aspiring Head of School and you want to accelerate your leadership growth? If you answered “yes” to any

education self-improvement

All Episodes

34:18

Episode 180: The Email That You Should Never Send

The Private School Leader Podcast ·

2026/03/28

Has this ever happened to you?You receive an email from an upset parent, an upset teacher or an upset board member. The email makes you angry. You immediately write a response to that upsetting email. You hit send. And almost immediately, you wish you hadn’t. You wish that you could put the “toothpaste back in the tube”, but you can’t. You wish that you had a time machine, but you don’t. This has happened to me far too many times during my career. Unfortunately, it usually made things

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30:53

Episode 179: How To Be The Leader Your School Needs...

The Private School Leader Podcast ·

2026/03/21

Back in the 90’s and early 2000’s, I was a basketball coach. I coached Boy’s Varsity for nine years and coached 5th/6th Grade Girls for seven years.I wasn’t the same coach the entire game: If my team was making a lot of mistakes, they needed a teacher. If my team was down by a lot of points, they needed an encourager. If my team was not playing up to their potential, they needed a motivator. My team needed me to be a different kind of coach at different times during the season or even

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45:10

Episode 178: 5 Strategies That Will Boost Your...

The Private School Leader Podcast ·

2026/03/14

Where I live, we are lucky enough to have all four seasons. Last week, I saw the first robin of the year and some of the daffodils are starting to pop up.Spring is a wonderful season because it means winter is over and everything will be lush and green in just a few weeks. Unfortunately, this is not necessarily a wonderful season for private school leaders. Why? Two words. Enrollment Season. I think that there are three reasons why so many private school leaders get so stressed out about

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29:43

Episode 177: Extraordinary Empathy: The Hug That...

The Private School Leader Podcast ·

2026/03/07

On October 17, 1995, Kyrie and Brielle Jackson were born at the Massachusetts Memorial Hospital in Worcester, Massachusetts. The twins were 12 weeks premature and each baby weighed just two pounds.Kyrie was gaining weight in the days following their birth, but Brielle was having difficulty breathing, and her oxygen levels were dropping critically low. Nurse Gayle Kasparian, who was on duty that night, tried everything she knew to calm the baby girl. But nothing worked. As the minutes

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30:11

Episode 176: Here's Your Survival Mode Escape Plan

The Private School Leader Podcast ·

2026/02/28

On March 11, 2010 I was lying on the bathroom floor at my house. I had been lying there for an hour, because I couldn’t stand up. I couldn't keep anything down for two days and I was severely dehydrated and dizzy.I said to my wife, “I need you to take me to the emergency room.” After a lot of tests, I was told that I had four ulcers in the lining of my stomach and esophagus. Then the ER doctor asked me, "Do you have a stressful job?" My job as a Private School Leader had finally put me in

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41:30

Episode 175: The 2 Problems That 90% Of School...

The Private School Leader Podcast ·

2026/02/21

90% can be an awesome number or a terrible number.It can be an awesome number when: Your favorite team has a 90% chance of winning the championship You live in a city where 90% of the days are sunny It can be a terrible number when: 90% of the students in your Middle School have earned a detention in the last 2 weeks There is a 90% chance of rain on the morning of your annual Field Day Over the last three years, I have had conversations with over 200 private school leaders and there

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41:52

Episode 174: You Will Lose Good Teachers And Good...

The Private School Leader Podcast ·

2026/02/14

There are very few guarantees in life. However, there are probabilities.Think about your car. If you drive the speed limit, obey the rules of the road, have good tires and good brakes, you are less likely to get into an accident. However, if you speed, run red lights, drive on bald tires and your brakes are shot, you are probably going to get into an accident. Unfortunately, there are no guarantees in our private schools. Sometimes, we work really hard all year on retention and

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35:46

Episode 173: 4 Leadership Lessons From The 1988...

The Private School Leader Podcast ·

2026/02/07

When I ask you to picture the island of Jamaica, what comes to mind? Probably white, sandy beaches, palm trees and crystal clear water.What you probably don’t think about is snow, ice and needing to dress in multiple layers just to keep warm. But, in the late 1980s, the Jamaican Olympic Committee decided to send a team of athletes to compete at the Winter Olympics in Calgary, Alberta. The sport? Bobsledding. Predictably, people laughed. Even people from their own country mocked them. Many

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37:02

Episode 172: The 4 Things That Teachers Wish Their...

The Private School Leader Podcast ·

2026/01/31

I hate going to the dentist. The thing that I hate the most is when the dental hygienist gives me a shot of Novocain and says, “You are going to feel a little pinch.”Yeah, right! It feels like a needle just went through my gum and directly into my brain. I need to be straight with you. During this episode, you are going to feel a “pinch.” I am going to be talking about some things that your teachers wish you knew. Maybe it’s just me, but I have always felt that anonymous feedback from my

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33:11

Episode 171: Your Biggest Strength Could Also Be Your...

The Private School Leader Podcast ·

2026/01/24

We all know the name Arnold Schwarzenegger.Seven-time Mr. Olympia. Hollywood action star. The Terminator. At his peak, Arnold could bench press well over 500 pounds and had one of the most powerful physiques the world had ever seen. Being the most famous body builder in the world led to notoriety and eventually led to Arnold being the highest-grossing movie star in Hollywood. But, he also had some weaknesses. Flexibility? Not exactly his thing. Fine motor precision? Can you imagine Arnold

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37:55

Episode 170: How To Handle The Concerning Shift From...

The Private School Leader Podcast ·

2026/01/17

I don’t like snowplows.When I see a snow plow, that means that the roads are snow covered. I don’t like driving on snowy roads, especially because of the hilly terrain where I live. There’s also another reason that I don’t like snow plows. For the 21 years that I was a Head of School, getting our school’s parking lot plowed always seemed to be a recurring source of stress. There is something that I like even less: “snowplow parenting.” Snow plow parents constantly try to clear the path for

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29:03

Episode 169: 3 Ways To Lift Your “Leadership Lid”

The Private School Leader Podcast ·

2026/01/10

I listen to a lot of Sports Talk Radio. At this time of year, the NFL playoffs give everyone a lot to talk about. But, after the Super Bowl, the hosts of the local and national shows have to try pretty hard to manufacture topics.Inevitably, one of the hosts will start talking about the GOAT in every sport. Of course, GOAT stands for the Greatest Of All Time. In my opinion, the GOATs in the four major sports are Michael Jordan, Tom Brady, Mario Lemieux and Babe Ruth. That said, I think that

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33:38

Episode 168: 4 Leadership Lessons From Captain Sully...

The Private School Leader Podcast ·

2026/01/03

On January 15, 2009, US Airways Flight 1549 took off from LaGuardia Airport, bound for Charlotte. Just 94 seconds after takeoff, the plane struck a flock of geese.Both engines failed, at just under 3,000 feet, over one of the most densely populated cities in the world. Captain Chesley “Sully” Sullenberger had just seconds to make a decision. Try to turn back to LaGuardia? Try to make it to Teterboro airport in New Jersey? Or do something no one had ever successfully done before, land a

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30:53

Episode 167: If You Only Make 1 New Year's...

The Private School Leader Podcast ·

2025/12/27

If you watch TV between Christmas day and New Year’s Day, you will see a lot of commercials for gym memberships. In fact, if you watch the New Year’s Eve coverage from Times Square, you will immediately notice that Planet Fitness is the exclusive sponsor of the big ball drop.Of course, gym memberships are being advertised because the most common New Year’s resolution is to get in better shape. Unfortunately, most studies show that around 80% of New Year’s resolutions never make it to

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34:37

Episode 166: The Top 10 Leadership Nuggets Of 2025

The Private School Leader Podcast ·

2025/12/20

If you have listened to even a few episodes of this podcast, you know that I like lists. It might be “The 4 Strategies To…” or “The 5 Secrets Of…”, but I love to organize my thoughts into lists.I especially love “Year-End Top 10 Lists”, like: the top 10 movies of the year or the top 10 books or TV shows of the year. With that in mind, I have looked back over the last 52 episodes and pulled out what I think are the best leadership strategies, quotes or phrases. On today’s episode of The

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36:03

Episode 165: The #1 Frustration Of Private School...

The Private School Leader Podcast ·

2025/12/13

We all have pet peeves. For some reason, most of mine tend to happen at the grocery store.It bugs me when the person in front of me has 35 items in the “10 items or fewer” lane or when someone is walking really slowly or taking up the entire aisle with their cart. My latest pet peeve has to do with the ubiquitous pop up ads that appear anytime I am trying to read something online. Even worse, the X to close the ad seems to be getting much smaller than it used to be. Pet peeves

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31:55

Episode 164: Do These 3 Things When A Parent Hijacks...

The Private School Leader Podcast ·

2025/12/06

On June 21, 1985, a domestic flight in Norway (Braathens SAFE Flight 139) was hijacked mid-flight. The aircraft was a Boeing 737, carrying 121 people (116 passengers and 5 crew.)The hijacker had an air gun that looked real, and claimed that he had planted explosives on board. His demands: speak to the Prime Minister of Norway and the Minister of Justice of Norway. Everyone remained calm and the incident ended with zero injuries and zero fatalities. According to the report that followed the

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29:51

Episode 163: The 3 Biggest Indicators Of A Healthy...

The Private School Leader Podcast ·

2025/11/29

Back in the summer of 2021, one of my daughters was driving a Chevy CRUZE with over 110,000 miles on the odometer. She needed to trade it in and get a more updated used car, with less miles on it.We found a car that she liked and got a car wash on the way to the used car lot. We vacuumed the inside and even paid extra to get the shiny stuff sprayed on the tires. It looked great! Unfortunately, on our drive to the used car lot, the check engine lights started coming on, one by one. Our

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42:22

Episode 162: When The Best Thing About Your School Is...

The Private School Leader Podcast ·

2025/11/22

A little bit of fire, under control, is a good thing.I love grilling in my back yard and a hot dog always tastes better straight from the grill. When my daughters still lived at home, we would really enjoy making S’mores over our fire pit. Once a year, we would go to a Christmas village to look at the lights and we would always warm up with some hot chocolate by the bonfire. Unfortunately, fire isn’t always under control. In just the past few years, the wildfires in Maui and Pacific

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35:47

Episode 161: How To Turn Fragile Kids Into Resilient...

The Private School Leader Podcast ·

2025/11/15

Do you have any fragile kids at your school?Do some of your students give up easily when faced with a challenging problem or concept? Are your students sometimes too worried about “looking smart?” Do any of your students get extremely upset when they make a mistake on an assignment or get a question wrong on a test? Do any of your students get really anxious about the grades that they get on tests and report cards? This is a very common problem in private schools. Some of the children at

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180 results

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