Scott Hanselman

10 Guerilla Airline Travel Tips for the Geek-Minded Person

April 01, 2008 Comment on this post [26] Posted in Musings
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Photo by Joshua DavisThere's a million sites with a million travel tips, so I won't even try to imply that I know what the Rick Steves of the world have worked so hard to figure out.

However, I do fly around a lot and I have for many years. I'm a geek, I like tools and I solve problems in my own niche way. It's not the way others might do it, but it seems to be working pretty well.

I just narrowly avoided a REALLY bad situation in Chicago (ORD) a few minutes ago where six flights to New York's LGA airport had cascading delays. My 3pm flight was now at 6pm which would have had me arriving into New York at 9pm! Considering I have a 9am talk, that could be disastrous. Here's how I saved my butt.

#1 Take Action at the first sign of trouble

Always have the # of the airline (or their preferred line). Nothing wastes time like digging for stuff. Use a service like to keep all your travel details in one place. For example, today I called United from my phone the second I saw the delay appear on the board.  I also go in line at Customer Service, but I had a person on the phone well before the line moved.

#2 Know the schedule

Don't just know the schedule for your airline, or for your flight. Know and print out ALL the flights going to your destination the day you're traveling. This provides you power as you'll know what parallel flights are leaving before the other travelers, even before the flight personnel. I use from my phone to stay on top of flights while on the go.

Knowing other airlines' schedule is useful because when mechanical difficulty cancels a flight you can insist that Airline #1 move you to Airline #2 if it's totally clear that there's no other way to get you to your destination on #1. Last flight I was on United had a mechanical difficulty and completely canceled my flight. The whole plane got in line to get on the next flights out, but this was the last flight of the day out of that city for that airline. I knew there was a Delta flight in an hour, so I took off for the Delta desk while calling United at the same time. I told them what flight I was on and that I wanted to be moved to Delta. I was kind, but firm, and only 1 hour late coming home. As I was boarding the Delta flight, I saw that United was passing out hotel vouchers for the folks on the first flight.

#3 Make their job easy

Speak their language and tell them what they can do to get you out of their hair. Refer to flights by number when calling reservations, it saves huge amounts of time. For example, today I called United and I said:

"Hi, I'm on delayed United 686 to LGA from Chicago. Can you get me on standby on United 680?"

Simple and sweet. I noted that UA680 was the FIRST of the 6 flights delayed and the next one to leave. I made a simple, clear request that was easy to grant. I told them where I was, what happened, and what I needed all in one breath. You want to ask questions where the easiest answer is "sure!"

#4 Never give up a guaranteed seat for a chance at a seat.

That said, always get on cascading standby. Make sure to ask them if your reservation will move from flight to flight if you don't get on standby. You'd be surprised how many reservations go missing or float around in the system. Always make sure you have your ACTUAL guaranteed ticketed seat for some flight later in the day in case the earlier standby's don't work out.

#5 Never check luggage

I did two weeks in Malaysia once with only carry on. Seriously, checking your bags not only slows you down physically but it also limits your options. When you talk to Customer Services, the FIRST thing they'll ask is "did you check bags." Your bags can't move as fast as you can.

#6 Be absolutely pleasant at every point

I can't stress this enough. Never raise your voice or demand anything. Be nice to people. Nothing you need to go (unless it's a child's health) to is important enough have a complete freak-out in public at the Airport. I've seen personally a half dozen different incidents where Airport Police have taken people away and charged them for disorderly conduct. More importantly, very rarely will you be talking to the person who screwed up your travel. They are just doing their job.

Try to be inclusive, using terms like "we," like "what can we do to fix this?" If the person seems to have a power trip, try using "you" sentences that inflate their sense of power. "Can you help me make this right?"

Today I said to an agent, "If you get me on this flight, you'll only need 2 more miracles for sainthood!" This got me an immediate smile and a pleasant transaction.

#7 Keep ahead of the wave

When disaster strikes, you have 15 minutes before the masses figure it out. Folks will queue at the drop of a hat, but savvy travelers will leap into action and start a multi-pronged approach. Call your assistant, spouse,  boss, travel agent, get on the phone, go to the departure boards. Always have at least two options. Even try going to the next gate, preferably a near-empty one with an agent behind it. Anyone at any terminal can usually fix your issue while the rest wait in a queue.

#8 Setup SMS Alerts on your airline

The best way to know what's happening before the public is via SMS Alerts. Corporate will often send gate changes before they are announced on the flight. This can save you time while trying to find the monitors upon leaving the plane. You can also setup notifications for delays. More information is better.

#9 Always wear a jacket or sport coat.

Don't look like a schlub. Have a nice pair of shoes. Shave. Well-dressed, kind, professional people get upgrades. I started wearing nice Cole Haan shoes and a sport coat when I travel and I've been consistently upgraded about 1/5th of the time. I'm convinced being fresh and clean and pleasant is the reason.

#10 Use your miles for upgrades

I don't have status on any airline, just a bunch of miles all over. Never enough for a free flight, so I never even try to use my miles for free flights . I always use them for upgrades and I offer to use them at the point where I'm talking to a customer service representative. Often, if you are pleasant beforehand, they'll just upgrade you without deducting the miles. Worst case, you get upgraded and use your miles. Best case, you're just upgraded.

Eek, they've called my boarding group, so I'm off! Bye!

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Photo by Joshua Davis

About Scott

Scott Hanselman is a former professor, former Chief Architect in finance, now speaker, consultant, father, diabetic, and Microsoft employee. He is a failed stand-up comic, a cornrower, and a book author.

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April 01, 2008 1:57
Ah, now I like this topic even more than the usual programming fare. I commuted between Washington DC and Southeast Asia for two years, and all of this resonates with my experiences except the following:

I don't have status on any airline, just a bunch of miles all over.

I've found that the single most important factor in a pleasant air experience is having status. If you have status, you can be speaking to an agent in seconds, not minutes (see #7). If you have status, you will be first in line for standby (see #4). If you have status, you can skip the longer lines and be speaking to an agent more quickly (#1, #3, #6).

My number one tip is to pick a "big three" alliance (Star Alliance, One World, or SkyTeam) and stick with it, even if it means paying more for one particular flight here and there. If someone else is paying for an booking your airfare, it's not outrageous to insist on an alliance, particularly each alliance has two major airlines participating in the US.

That's my $0.02, and would be my rule #0.
April 01, 2008 2:07
Wow, from twitter to blog in less than 4 hours...that's pretty impressive.

I must learn how to do this from the "travel ninja" ... :-)
April 01, 2008 2:25
Have to echo what PWillis said - I've been flying only Hawaiian airlines for years, and they sent me a nice letter one day telling me I was a Premiere member (I had 50,000 miles).

This one thing entitles me to:

1) Shorter security lines (you get to go through the first class/premiere line at pretty much any airport)
2) I get to hang out in the "Alii Room" at the Honolulu airport. Sounds swanky but it's quiet with free wifi and there's a dedicated counter attendant right in the room.
3) No fees for changing my flights
4) Free upgrades when the flight is empty
5) Double miles certain times a year.

Now you may be thinking "I don't fly that much" and, well, neither do I really (maybe 4-5 times a year). The trick is to get the Visa that has the miles (I have a Hawaiian Miles Visa) and use it for everything - literally everything - and pay it off every month.

Food, going out... whatever. Think about how much you spend each month and BAM! you'll be premiere in no time!
April 01, 2008 2:26
Oh yah - the Premiere rooms usually have a kids area with a TV on... Godsend...
April 01, 2008 2:36
I always assume so much about traveling. What you stated I consider standard operating practice.

The other thing to note, especially if in the north eastern US, north west US, Europe or Asia, they have things we in the US generally don't grasp anymore. Decent reliable train service that is often better in performance and price than airline travel. It is often a good thing for those hops in the areas stated to just skip the plane and get on the train. :)

Besides, the train is usually about 1,234,987 X more roomy and comfortable than any airline.
April 01, 2008 2:50

Some good tips. I have to disagree with your last bit on upgrades. Granted, you're doing the right things if you're dressed nicer (no suit necessary), polite and don't smell bad (bad breath, booze smell, whatever). However, depending on the airline, it's your "elite" status that will matter most. I fly United 99% of the time and the chances of a UA gate agent (GA) doing an "op-up" for free for someone with no status is very low relative to that of a frequent flyer (FF). Many FFs are "on the list" to get upgrades. It against policy to give a free upgrade if there are people waiting to "pay" for the better seat. There's a complex almost ritualistic dance that goes on to sort and process upgrades.

I only bring this up because I see people all the time trying to get upgrades by dressing up and trying to be "nice" the the GA only to be turned down. Comments like yours only encourages this behaviour.

To be clear, op-ups happen. But it's much rarer than I think many people want to believe. That said, I fly too much so maybe I'm just cynical. :-)


April 01, 2008 2:58
It would help if I typed my blog address right. <sigh>
April 01, 2008 3:15
I gotta agree with Brian, Rob and PWills above. My wife and I are lowly Premier members with United through flying 25K annually, but it makes a world of difference, from check-in, through security (at some airports with elite lines), onboard (Economy Plus = more legroom, can't live without it...especially when flying with a 2-year old), and potentially (hopefully) upgrading. You should try consolidating on United if the routes and schedules work for you, or another airline if it fits your travel habits.

Cheers, Tom
April 01, 2008 3:15
I have to agree with PWills and Rob. I fly at least once a month and it is paid for by the customer. Unlike some big contract firms I charge cost for air tickets not cost + x% so I always get the unrestricted flexi full fair super unlimited economy seat. Most importantly on the airline of my choice. So I have status and pts and that is a biggy. I am now gold 1 from the top with my airline and that has a whole list of benefits (worthy ones too) and hey some of my best code has been created sitting drinking free beer (most creative code) in a lounge at an airport. I am kinda nuts but I find the environment very motivating. Also the perks are that in a few weeks time I am flying the whole family on a holiday just using pts and a few $ for tax that nobody seems to know exists.

On the upgrade point I think airline computer systems are very, very efficient these days at keeping tabs of who, why and what a customer's real status should be. eg. Before I got Gold I was upgraded to silver without actually reaching the mile stone in the set period. Kinda suggested to me that some other parameters are at work behind the scenes eg. As Rob said you have the credit card linked to the airline points so they are probably building a fantastic little profile of me freddy frequent flyer that can narrow down my habbits etc. especially if I have a UA credit card and purchase a Delta ticket which would kinda be a great little Linq query to establish a list of potential suck up to customers.

April 01, 2008 3:22
I just like that you refer to that thing in which people stand as a "queue" rather than a "line". Sign of a true geek :)
April 01, 2008 7:34
I knew I'd take a hit for the status thing. I've had status before, on United and Alaska, but it didn't make as much a difference as these tips. That said, let's add:

#11 Get status and squeeze it.
April 01, 2008 7:53
You should be on the Amazing Race!
April 01, 2008 12:18
Scott, your link to actually points to (double p)
April 01, 2008 14:48
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April 01, 2008 18:14
Years ago, I used to fly UAL and AA a lot. Those two airlines didn't always assign everybody seats, leaving open the chance to switch seat assignments. Do it! Ask for aisle (and exit row).

I don't know if that has changed, since I'm not doing business travel any more, and use SWA for all personal trips.
April 01, 2008 19:54
I saw the Twitter posts and was hoping you'd consolidate them into blog post. You've come up with a good reason to actually own a sport coat. Can't think of another reason for a "geek-minded" type to have one other than the occasional wedding...
April 01, 2008 21:41

Very nice post! I agree with every point. Another recommendation I would give people is that when on international travel with stopovers, make a one or two night reservation at a local Holiday Inn at the stopover point. In the event that you can't get on your next flight and the airline doesn't pay for lodging or lodging isn't available, this will come in handy. I recommend Holiday Inn because you have an option of not giving your cc# and your reservation automatically cancels if you don't show up by 6:00 PM. There may be other hotels like this as well.

April 02, 2008 13:32
I agree with the folks recommending status on an airline. I fly United and membership does have its privileges.

While it may be the case that airlines used to award upgrades to the folks who'd go and try to be all charming to the ground personnel (and these were usually men since it's easier to be flirtatious with most women if you are a man), United now seems to work with their status system when granting upgrades. Just two days ago I got a free upgrade on a 9hr flight (from FRA to ORD). No one saw how I was dressed (wearing jeans and a shirt), they just called my name and voila. I am Premier Executive and seemingly the flight mostly had tourists so it makes sense that I was on top of the list for an upgrade.

The same seems true for standby, you get on top of the list based on status even if you show up at the gate requesting it a bit later than some others.

The advice you offer is helpful, but as PWills suggested, start with status in which case you may be able to skip right over many of the other points.
April 02, 2008 14:22
I have never got an upgrade by just dressing nice, smelling good, and being polite. The only time I have got one is through using my miles.
April 03, 2008 10:02
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April 04, 2008 23:27
Well, the one thing I would disagree with is the checking bags thing. One thing that just burns me is the people who try to stuff gigantic pieces of luggage (that OBVIOUSLY don't fit in the 'your carryon must fit in this container' thing) into the overhead bins. Holding up everyone behind them trying to board, taking up twice as much room as everyone else, etc. You know the type. Please don't encourage this kind of behavior.

Other than that, these are great tips!
April 04, 2008 23:31
Heh. My next post will be on packing light. ;) I take a half-rolley and a backpack. Uber-light.
April 05, 2008 23:13
Great post Scott. You should post more about getting things done and lifestyle!
April 07, 2008 12:17
Agree with your point 6 but isnt it difficult to manage your self and be polite when u you know that things are not happening as they were supposed to be.
April 09, 2008 4:13
Another reason for point #9 that I learned the hard way over the weekend: If you dress nice on the plane you have something nice to wear to the office the next day, instead of needing to buy a new set of office appropriate clothes. I flew in casual clothes, my "work clothes" are still lost at Heathrow. My experience also validate point #5, I usually fly with only a carry-on, but this time took a larger suitcase. If you don't give your suitcase to them they can't lose it...
April 10, 2008 18:29
Also - you can use services like to get predictions of delays too!

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Disclaimer: The opinions expressed herein are my own personal opinions and do not represent my employer's view in any way.