Scott Hanselman

There'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 tripit.com 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 http://mobile.flightstats.com/go/Mobile 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!

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. I am a failed stand-up comic, a cornrower, and a book author.

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