About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. I learned this lesson from my wife in 2016. My daughter was wrapping up a year of college in Japan and we were headed over to pack her up and bring her home. Booked BNA-MSP-HND-HIJ. The first flight was cancelled due to a mechanical issue. And a long line formed behind a single agent for rebooking. I was in line and my wife wandered off. She approached a gate agent who had just boarded a flight and almost in tears asked nicely if she could help. She started typing and suddenly said come with me. My wife hollers at me and I broke line. She ran with us 3 gates down to a flight that had just boarded. Now we had two agents, one on the computer and one on the radio. In about three minutes we were on a flight to LAX-HND-HIJ. Even our luggage made it. My wife hugged the agents. We actually arrived earlier than our original flight. Contrast that experience with American screwing me twice in one month (and a gate agent actually laughing about it) is why Delta gets my $35-40k spend every year on international flights.

  2. H2O … if you were a Marine , you could have flown free to Iwakuni , without the drama .

  3. Be nice to your gate agent. They have the power to upgrade you or, if you piss them off, seat you in a seat in the back, by the lav, in-between the person with a screaming baby and the person of size.

  4. @alert
    My daughter got a free trip to Afghanistan, but didn’t really recommend the trip.

  5. Hi, I have (name problem). I know it might not work, but if you could (offer solution), it would really help me out!

    The more specific you can be about the solution the better. “If I could be on flight #### leaving at HH:MM” is much better than “put me on a later flight.”

    Also state your reality rather than asking questions. “(whatever) happened and I am not going to make my flight. Can you put me on (details of flight you can make)?” is much better than “What happens if I don’t make my flight?”

    One is asking for a solution and the other is asking for policy, which they may then feel inclined to follow.

    And, sometimes the software will prompt the agent to do a certain thing, and you can say, “Oh, I understand the computer thinks you have to do that, but is it possible to waive that in (whatever your circumstances)?”

    United has earned essentially all my airline business by being consistently flexible with me. (And having that really nice lounge at ORD C10!)

  6. @Alert I was smart. I joined the Army ;-). But between long flights on MAC and web seats on a C-130. I’ll stick to commercial aviation.

  7. @Linda: One thing gate agents definitely no longer have the power to do is give you an upgrade, except maybe on a later flight as part of negotiations to avoid an IDB.

  8. @Christopher an upgrade isn’t always to first or business. It can be to premium economy, a seat farther forward, a drink or meal voucher. There are lots of ways to be nice, up to, and including, an upgrade to business or first.

  9. My wife and I were in Miami, with plans to fly AA when the 737 Max 8 ground halt happened.

    It was supposed to be MIA -DEN, but with most Max 8 planes for AA being MIA based, suddenly no flights were available.

    I called EP number, they could find nothing.

    So, I grabbed the laptop, went to ITA Matrix, and found a three flight hop to get back..

    I called the EP desk and offered my solution. Since it was IrrOps, they waived any change requirements and booked us both on that route.

    Then the fun really started… with confirmed seats, we volunteered on every flight IF the offer was big money AND a confirmed seat on the next flight. (Repeat on next flight too!)

    We made $4k that day and had a ball.

  10. Whenever I tell a passenger No, I document their reservation with what was asked and what I declined to do, and leave a note if any questions call me.

  11. My wife and two kids had an award booking in J on American from Ord to Vancouver to Sydney on american and Qantas before Christmas in 2019. The Ord to Vancouver leg was discontinued and their booking was changed to include a long layover in Dallas.

    I kept searching for weeks for better options but there was no availability. For a laugh I rung American and got an older customer agent who was very nice. She suggested that we just fly Ord to lax to Sydney. I agreed that would be nice but there were no seats. She put me on hold and came back and said she could swap it. I immediately thought she was looking at economy…

    But no, she had managed to swap three of them into first and business class on AA metal all the way to Oz. A week out and a week before Christmas. Never knew agents had that power!!!

  12. @NedsKids I bet you’re a lot of fun at parties.

    Sugar always wins over versus vinegar. Be kind and a good human. Those who can help, will.

  13. Great so now you gave away all my tricks at least now the airline staff will get treated nice. Yelling and screaming at airport staff usually gets you delayed or thrown in jail.

  14. All good advice. Especially being nice and offering a reasonable solution. The airline agents usually seem to be looking for a way to fix things so they can move on, and you can help them do that.

  15. I love how basic civility and being nice to people around you is now a “trick” or a “life hack,” I say sarcastically. While everything said might be true, are we really becoming a society that is only willing to be civil and polite if we have an opportunity to get something for it? Wouldn’t it be nice if we were all a little kinder to everyone around us? Perhaps if we avoid spreading negativity, we’ll all have a more pleasant experience (and not just at the airport)? Let’s all try be kind to one nother, whether or not there’s a perceived treat to reward us. Maybe that gate agent is having a tough enough day without anyone being hostile to them or trying to to game them? Good deeds and a good attitude towards others will put you in a better mood too, which can be just as enjoyable as that upgrade. Best flight I ever had was one where I was booked in first class, but saw an elderly woman traveling with an infant who I had overheard was traveling to bring the baby to his father (her son in law), after her daughter’s death from cancer. It broker my heart. I quietly pulled aside an agent and asked her to upgrade the woman into my seat, and that I’d take hers. I asked her not to let the woman know that anyone gave up their seat and to just upgrade her as if it was company policy. I didn’t ask for (or want) anything in return. The entire flight, I felt good, regardless of the quality of the coach seat. For those who don’t do it often, spend some time doing good for others without expecting compensation. You’ll find it adds so much joy and value to your life, that the increase in your sense of self-worth will be more than worth it. (And you might just get recognized for your good works, but by then, you won’t care bout that part as much.)

  16. Sometime about twenty-five years ago I was on a one-day business trip BWI-ORD-BWI. It was on United, and I left from BWI because that way I could get Southwest fares without having to fly Southwest. The meeting ended early and I took the CTA Blue Line back out to the airport, watching the stalled traffic on the adjacent Kennedy Expressway which included airport buses and taxicabs. I got to O’Hare around 6:00 pm, with a 9:05 pm departure to BWI and not sure how I’d get home (trains to BWI Airport Rail Station would have stopped running by then). There was a United flight to Washington National Airport leaving at 7:10. I went to that gate, showed my super-duper-fare ticket to the agent, and asked if there was any way I could get on it. He said I would be last priority for standby and come back around 6:55. I went off, found dinner, and came back at that time. He did stuff on his computer and handed me a boarding pass. Everyone else was already on. I thanked him and got on; I had an aisle seat. Not only did I get to Washington DC much earlier, the subway was still running, and it got me home. Meanwhile, United got a seat back on the 9:05 to BWI which they very well could have needed. It worked out for both of us.

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