As a frequent business traveler, I’ve managed to accrue a wealth of award points with various hotel chains, rental car agencies, credit card companies and airlines, which makes traveling for leisure more of a financial possibility, especially when it involves other people. Of course, these companies have some restrictions — blackout policies, extra fees — to which I’ve grown accustomed, so long as they are made immediately obvious to me. So when a company fails to tell me I’m not allowed to do something when their web application seems to think I can, I become generally upset. Enter: Delta Airlines.

The five months I spent flying to and from St. Thomas allowed me to earn so many miles on Delta that I actually became a Platinum Medallion flyer — the highest tier possible. I don’t remember ever having to call Delta customer service to book a flight; their website is cleanly designed and navigable, when compared to most other airlines’ sites. And under normal circumstances, their customer service line is actually helpful. I tell you this because my latest experience with them — both online and on the phone — left much to be desired, and is not indicative of what I normally expect. Perhaps my particular scenario was one they had never encountered, but the experience I had could have been better… much better.

I was purchasing a ticket for a friend to visit me in Austin next month. Delta touts the ability to pay for most itineraries with miles if you have status, and even offers a conversion: 100 miles equals 1 dollar. There is no information on Delta’s site that says I can’t use my miles for another person’s ticket, but to be sure, I performed a Google search and found a forum post that confirmed this was indeed possible.

I log into the site as I normally would, and proceed to search for flights. After selecting the outbound and inbound flights, the cost of the flights is presented to me — $380 –  and, at this point, I’m presented with the option of paying with miles. However, I’m only allowed to use mile in increments of 5,000 miles, selecting only from a dropdown menu:

Because I’m unable to enter the number of miles I want to use, I have to spend in increments of 5,000 miles, which is fine if the dollar amount is number that ends in “50″ or “00.” However, because the flight is $380, I’d have to spend 5,000 miles for a remainder of $30, which diminishes the value of my miles. Naturally, I don’t want to do that, so I spend 35,000 miles and try to pay for the remaining balance of $30 on my credit card:

Fail #1.

I go to the next screen, where I enter passenger and billing information. Since the passenger is not me, I clear out my information and enter my friend’s. The billing information is mine, so I enter my credit card number. Everything seems to check out so far, as I’m allowed to proceed to the review screen where I confirm the itinerary and pick seats. I hit the “Purchase” button, and it happens:

“We’re sorry. We’re unable to process your transaction at this time due to technical difficulties. Please try to book your flight later.”

Fail #2.

I had tried this two nights before, late at night, with the same message, so I knew that it wasn’t some anomaly that any site is capable of. I decided to call Delta customer service to find out what was going on.

(Incidentally, I called customer service the night I first encountered the error, and stayed on the phone on hold for 15 minutes before realizing that it might have been closed for the night. I did call around midnight my time, but it would’ve been nice for the “on hold” message to tell me what their hours were. Let’s call this Fail #0.)

I called customer service and spoke with a somewhat helpful representative. She said that I could pay for the flight using my miles on the phone with her, but it would cost me an additional booking fee, which I wasn’t going to pay for, since the site had failed me. I explained to her what I did on the site, and she offered to send me to their website support division. In fact, she insisted on it.

I normally despise talking to website support people, and my feelings did not change after this call. When you know more about how websites work than the person with whom you’re talking, it’s hard to not lose your patience. Still, I played along: I told the support representative what I experienced, the steps I took the produce the error, and the error message itself, which was generic and unindicative of what actually happened. He proceeded to ask me questions about my computer, which is when I realized that this problem would never be solved:

Rep: What type of computer are you using?
Me: Mac.
Rep: Uh, Mac?
Me: Yes.
Rep: And what operating system are you running?
Me: Mac OS X.
Rep: OS… X?
Me: OS 10.5 Leopard.
(Rep mulls this over for a bit)
Rep: What browser are you using?
Me: Firefox 3.
Rep: Do you have Internet Explorer?
Me: No, this is a Mac. I don’t have IE.

(Technically, this is a fair question. Internet Explorer 4.7 was the last version of IE for the Mac. Of course, Microsoft ceased to support this browser years ago, but I’m sure there are a few diehards that stay true to this archaic browser.)

Fail #3.

After taking down my information for an incident report (which I will probably never hear about ever), the support representative asked if I wanted to book a hotel or a rental car. Why would I need those things if I can’t even book a flight? I asked to be sent back to Delta’s main Customer Service line. Much to my dismay, the rep told me he was unable to transfer me, and that I would have to call the main number again.

Fail #4.

I hung up and took deep breaths before my next call to Delta Customer Service. I had been exhibited great patience on the phone, as noted by my colleagues who were in the room when I started the call… 20 minutes before. I called back and got a different Customer Service rep, who was less than helpful. Unlike the first rep, she told me that I could not pay for the flight using both miles and a credit card over the phone, and that I would have to do it on the site. I explained to her that I tried this already with no success, and that I had wasted my time trying to figure this out with other reps.  She responded by saying that I had to pay for the flight entirely with miles, which was a problem for me, since I would be forced to spend 40,000 miles for a flight that really costs 38,000 (the diminished value I wrote about earlier). At this point, I lost any patience I had left. I explained to the rep that I thought everything — the inability for me to pay for the flight I way I wanted to, being bounced around to diffrent reps, losing the value of my miles — was completely ridiculous, and she said that it is a “marketing” issue.

A marketing issue!?

I started to tell her that it was an issue of logic, but I realized that I was wasting my breath. I went to the site, begrudgingly paid for the entire flight in miles, and hung up the phone.

Fail #5.

So how do you fix the fails in this situation?

For Fail #0 (being stuck on hold late at night): Set up your Interactive Voice Response (IVR) system to inform callers what hours Customer Service has. This will prevent people from staying on hold longer than they have to. Simple fix (hopefully).

For Fail #1 (limited dropdown options): Instead of using a dropdown to force users to select an option, consider a simple input box that is validated on the client and server side to accept only numeric values. If miles must be numbers that end in “0,” consider using a slider control that limits the values, but not as limiting as the dropdown. If done in a smart way, the default value on the slider can be the minimum number of miles it would take to book the flight if the customer did not want to pay any money out of pocket, or the maximum number of miles based on what the customer has in his/her account. However, since the slider control may not be accessible, from a Section 508 perspective, consider implementing both types of controls.

For Fail #2 (ambiguous error message): If possible, provide some sort of error code that can be metioned to a customer service representative. The error code may not make sense to the user, but it’s much more helpful than a canned response with a phone number.

For Fail #3 (quality of support staff): Train your support staff troubleshooting skills, and not just the ability to take down information for an incident report. I felt like I walked through the site while the rep was taking notes, with nothing to show for it (except a passive-aggressive blog post).

For Fail #4 (inability to transfer phone calls): I shouldn’t even have to report this fail, let alone come up with a solution to this, but I will anyway. Allow for any rep to transfer to any number in the system. There. That wasn’t hard.

For Fail #5 (consistency of customer experience): If there is a standard way of handling certain user scenarios, then why can’t two customer service representatives deliver the same message? The first rep said I could book the flight for an extra cost, while the second couldn’t help me at all. The only way in which these two reps were consistent was their lack of empathy with the situation.

Some of what I suggested can be fixed with relative ease. The rest? Not so much. But hopefully your customer experiences with Delta, or any other company for that matter, will be more pleasurable than mine.