lessons in jewish educational leadership from an airline pilot.

For the past three years, a big part of my job 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.

Captain Flanagan

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.” Sukkah 28a and Ein Yaakov, ad loc1

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 cared for.

When there are unac­com­pa­nied minors aboard his plane, Captain Denny makes a point of mak­ing sure that the cabin crew is pay­ing close atten­tion to their needs. Then, before take­off, he uses his (per­sonal) 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, he dras­ti­cally changes his pas­sen­gers’ atti­tudes toward airlines.

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 a student’s entire atti­tude about reli­gious school — and about Jewish learn­ing in gen­eral — could be improved if they got to be with a 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 for 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 arti­cle3 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.

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 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. It 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. Working along­side some­one so pos­i­tive and so deter­mined 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.


Also pub­lished on Medium.


  1. as quoted by Joel Lurie Grishaver in Teaching Jewishly (2007). (back to foot­note in text)

  2. Nicholas Kralev, “United pilot earns top praise.” The Washington Times, November 16, 2009. (back to foot­note in text)

  3. Scott McCartney, “To a United Pilot, The Friendly Skies Are a Point of Pride.” The Wall Street Journal, August 28, 2007. (back to foot­note in text)