Lessons in Jewish Educational Leadership from an Airline Pilot

by Josh Mason-Barkin

(cross-posted to Josh’s blog)

For the past three years, a big part of my job at Torah Aura Productions has involved flying around the country to work with synagogue school educators and teachers. As a result, I’ve spent a lot of time on planes. And since my natural predilection is to be geeky about these sorts of things, I’ve become something of an airplane nerd who now feels at home among communities of frequent travelers.

As part of my geekiness, last year I had the opportunity to meet a special pilot, Captain Denny Flanagan, who flies for United Airlines. Captain Denny, as he is affectionately called by the frequent flyers who adore him, has become a celebrity among road warriors for his amazing dedication to customer service. He’s an experienced airline pilot who goes out of his way to make the commercial air travel experience pleasant (gasp!) for customers.

I’ve read a lot of accounts of the big and small things that Captain Denny does to make air travel better. He’s an incredible ambassador for the entire industry and for his airline. (You can read some of these accounts here, here, and here.) If you’ve been on an airplane recently, you probably know that the airlines could use a lot more people like Captain Denny.

Recently, it occurred to me that Captain Denny isn’t just an example for people who work in air travel. In fact, it’s clear to me that — although he is not Jewish and not an educator — he actually has a lot to teach Jewish educators about how to carry ourselves, and about how to be leaders. This, I figure, is the perfect opportunity to find a nexus between two things I love: Jewish education and airplanes. So, with a tip of the hat to Carol Starin’s Let Me Count the Ways, here are six lessons in Jewish educational leadership that I’ve learned from Captain Denny:

1. Greet everyone with a cheerful countenance. Think about the last time you boarded an airplane. I’ve boarded a lot of airplanes in the last couple of years, so I have the process down pretty well.

First, you have to make your way through the crowd of people at the gate, angling to get on the plane as quickly as possible. You have your ticket scanned by the gate agent so that you can then queue up in the jetway as people make their way onto the plane one at a time. When you make it through the airplane door, you’re confronted by stressed flight attendants who are trying to complete all their pre-departure duties while at the same time making sure that people can find their seats and that everyone manages to get their carry-ons stowed beneath their seats and in the overhead bins. Air travel can be stressful for a lot of people, and the boarding process — which involves stuffing more than a hundred people through a single door and into a thin metal tube — makes the whole procedure worse.

Now imagine this boarding process: A few minutes before boarding begins, the captain appears at the gate and grabs the loudspeaker mic. He introduces himself, tells you about the plane you’ll be flying on, and about any possible delays. He thanks passengers for flying his airline, makes a couple of jokes and explains that he and his crew will be glad to answer any questions when passengers board the plane. A few minutes later, boarding begins and passengers are greeted at the aircraft door by the captain. He hands out information cards about the Boeing 757 that he’s about to fly, and he offers “wings” to the children. He shakes passengers’ hands and welcomes them aboard his aircraft.

The latter description is what happens on every flight piloted by Captain Denny. Can you imagine what a difference that greeting makes for nervous, stressed passengers?

“It is said that Rabban Yohanan ben Zakkai never ever… let anyone else open the door to his students. After him, his disciple Rabbi Eliezer conducted himself in the same way.”1

Our classrooms can sometimes feel like commercial air travel. Our students may be nervous or anxious to be there, or they may show up to religious school after a stressful day in their secular school. Captain Denny echoes our tradition when he teaches us the value of greeting everyone as they walk in the door.

(FYI: The “Guru of Greeting” in the Jewish community is Dr. Ron Wolfson. He discusses the concept at length in his excellent and important book The Spirituality of Welcoming. If you’re at all interested in exploring this topic at greater depth, the book is a must read.)

2. People matter more than systems. If you’ve ever flown with your pet in the cargo hold, or if you’ve ever sent a child on a flight as an unaccompanied minor, you know that airlines have systems for these sorts of things.

If you fly with a large dog, for example, you put him in one of those big dog crates and check him in at the ticket counter. Animals are loaded into a pressurized part of the cargo hold, and once you drop your dog off, you don’t see him again until you pick up your luggage at your destination. Pet owners say that traveling this way can be very stressful on animals, and almost as stressful (if not more) for their humans.

Though they don’t have to sit in the cargo hold, things aren’t so much different for unaccompanied minors. They’re dropped off with airline personnel, who make sure that they get on the plane, take the right seat, and make any airport connections. Parents are out of the loop from drop off until their child is picked up at their destination. Most unaccompanied minors I’ve met on planes handle the process like pros, but I imagine having your child alone on an airplane can’t be easy for parents.

Things are a bit different on Captain Denny’s flights. When he’s doing his pre-flight checks, he likes to stop by the cargo hold, where he checks in on pets and takes pictures of them with his camera phone. When passengers board, he finds the pet owners and shows them the pictures, all the while assuring them that their pet is being well taken care of.

When there are unaccompanied minors aboard his plane, Captain Denny makes a point of making sure that the cabin crew is taking good care of them. Then, before takeoff he uses his cellphone to call their parents. He introduces himself, promises to take care of this most precious cargo, and lets them know if there will be any flight delays.

These gestures probably take Captain Denny four or five extra minutes for every flight he pilots. But those four or five minutes of effort are priceless for the passengers and parents who get pictures of their pets and phone calls about their kids. The airlines have systems for these things, but Captain Denny knows that behind those systems are real people who have real concerns. He transcends the systems, and as a result, his passengers’ entire attitude about airlines is drastically improved.

How might we follow Captain Denny’s example in our schools? We have systems for lots of things: school registration, class placement, carpool, report cards… But behind those systems are real children, real parents, and real families. It would be easy to say, “Sorry. I can’t move you from your class. We have too many people in the other class, and numbers are numbers.” But what if the student’s entire attitude about religious school — and about Jewish education in general — could be improved if they got to be with their friend in that other class?

3. Little things make a big difference. Can you imagine how much better people would feel about air travel if the airlines did little things to make people feel better about the experience? Southwest knows this, which is why they make such a big deal about smiling and about your bags flying free. Greeting people at the door, taking pictures of pets, and calling parents are some the little things that Captain Denny does that make a big difference. But it goes way further.

Customers on Captain Denny’s flights frequently get thank-you notes from him. He pre-writes the notes before he gets to the airport, and adds customers names when he gets the passenger manifest on his flight. People who fly a lot on United get the notes, which convey Captain Denny’s gratitude for their loyalty. He also makes a point of sending them to coach passengers stuck in middle seats “with the intent to emotionally and physically make their seat bigger.”2

There are lots of little things can we do to “emotionally and physically” make our students’ classroom seats bigger and to build their self esteem. My friend Carol Oseran Starin is an expert at this. She suggests being careful and thoughtful in the way we give praise. (Check out her article on the topic here.) She also suggests making a point of showing students that school — and your classroom in particular — is a special place, kind of like Captain Denny’s airplane.

4. Having fun is important, especially when it’s not expected. When was the last time you saw a flight crew going out of their way to make sure a plane ride was fun? On most of Captain Denny’s flights, he has trivia contests and raffles in which he instructs flight attendants to give away 10% discount coupons and unopened bottles of wine.

Good teachers know that adding fun and whimsy to the classroom is an important part of their teaching repertoire. Captain Denny teaches us to take that step even further. We need to make sure that our students are having fun at those times when they least expect it. How much more engaging would school t’fillah be if we allowed ourselves and our students to be (appropriately) playful? What if we had contests in the carpool line, or raffles on school registration day?

5. The buck stops with you. Mechanical and weather delays are a fact of life in air travel. In most cases, passengers are stuck on the plane, waiting to take off, and then possibly left dealing with the hassles of missed connections, lost bags, and delayed travel plans. Clearly, these realities aren’t the pilot’s fault, and there’s not much he or she can do to improve the situation.

Wrong, says Captain Denny. A recent Wall Street Journal article explains that “…if flights are delayed or diverted to other cities because of storms, Capt. Flanagan tries to find a McDonald’s where he can order 200 hamburgers, or a snack shop that has apples or bananas he can hand out.”3

Captain Denny realizes that even though delays are beyond his control, and that airline bureaucracies are set up to handle the consequences, on his plane he’s the boss. And the buck stops with him. So he takes responsibility, and does his best to make things better for his passengers. He’s also been known to get on the phone with the airline to make sure that passengers are re-booked on convenient connecting flights. He hears passenger concerns, and he takes personal responsibility for solving them.

I once saw a similar display from a synagogue educator. The caterer who was supposed to supply dinner for the teen program screwed up and didn’t bring the food on time. The dinner wasn’t the educator’s responsibility; the synagogue’s program director was in charge of handling the catering, and the (very busy) educator could have easily blamed that other person and let the students go without dinner. Instead, she realized that as the director of education, the buck stopped with her. She dropped what she was doing, picked up the phone and called a kosher pizza place to make sure that food was waiting for the kids when classes broke for recess. This sort of behavior is nothing new for her. Parents who are frustrated with the scheduling of their children’s b’nai mitzvah dates, kids who are having trouble with Hebrew, and teachers who run out of supplies all know that they can go to her with their issues, and that she’ll take personal responsibility for making sure that these challenges are addressed.

Another thing about Captain Denny: After flights, he’s known to go back into the cabin to help flight attendants and cleaning crews pick up trach. He personally thanks the ground crew for de-icing the plane. He helps flight attendants show passengers to their seats. Good school principals help teachers clean up classrooms, work alongside the custodian to make sure chairs are set up, and stop in the hallway to repair the paper maché falling off the bulletin board. When the buck stops with you, you’re not above doing whatever it takes.

6. Attitudes are contagious. You might think that flight attendants hate being assigned to Captain Denny’s flights. He demands excellence from them, and as a result they have to work a little harder to go the extra mile.

But it turns out the opposite is true. Flight attendants love working for him. Working with him makes them feel less cynical about their jobs. It makes them realize that providing good customer service can be a joyful experience, and that air travel can be exciting and fun. His attitude is contagious, and working with him reminds other airline employees why they got into the business in the first place.

The same is perhaps even more true in Jewish education. An eternally positive educator who demands excellence sees that their attitude can spread like an infectious disease. Teachers love working for educators like these. It makes them feel less cynical about the difficulties of Jewish education. It makes them realize that teaching can be a joyful experience, and that learning can be exciting and fun. Working for educators like these reminds even the most jaded teachers why they got into Jewish education in the first place.


1. Sukkah 28a and Ein Yaakov, ad loc, as quoted by Joel Lurie Grishaver in Teaching Jewishly (Torah Aura, 2009).

2. Nicholas Kralev, “United pilot earns top praise.” The Washington Times, November 16, 2009. Available here.

3. Scott McCartney, “To a United Pilot, The Friendly Skies Are a Point of Pride.” The Wall Street Journal, August 28, 2007. Available here.