I recently took my family to Orlando, FL for a speaking event and to visit Disney for Mother’s Day. As much as I wished I had a private jet to take us all there with no hassle or discomfort, like everyone else we took the general airlines to our vacation. It didn’t come as a surprise that we experienced some unusual issues and I decided to do something about it — write the CEO of Southwest Airlines, Gary Kelly.

My hope for this post is to not only highlight how a small situation can turn into a larger problem but to show how Southwest handled things on their end and what we all can learn from this.

Below I have outlined what happened and how Southwest responded but first I want to share 10 points that made all the difference with how things ended up.

  1. During the trip, I kept my composure when talking with Southwest representatives.
  2. I took action (wrote an email) as soon as possible.
  3. I wrote in a style that made me human.
  4. I not only addressed the issues but also let them know that I am a fan.
  5. I went to the top.
  6. I call Southwest on their wrong.
  7. I was willing to accept that not everyone was out to get me.
  8. I asked for them to make things right.
  9. I set reasonable expectations.
  10. I patiently waited for a response (didn’t go off on a Twitter rant).

Email to Gary Kelly, the CEO of Southwest Airlines


I am beyond disappointed.


My wife and three young daughters (age 6, 4, and 18 months) first trip to Disney started and finished on a beyond horrible note.

And it all could have been avoided.

Mother’s Day was spent at an outlet mall instead of making memories at the Magic Kingdom.

I own a small company and fly Southwest a lot.

Have been A List for many years.

I have friends that have spoken nationally on your stages and are great partners of your company.

I personally have spent time on stages around the world bragging about you in front of thousands.

And I think that if the same thing here happened to one of my clients, I as the leader of the company would want to know about it.

There were several human errors occurred that were not addressed in a way that I have come to expect from Southwest versus the other guys.

I know no one or company is perfect.

And that errors often come at the absolute worst time and for the customer, you would never want to disappoint.

But here is the quick backstory….

We were flying from STL to MDW on May 13th of this year.

When we checked in, our bags and my youngest lap child daughter’s ticket was attached to someone else’s reservation and ticket.

I am not sure how that happens but it did.

We didn’t realize it as I have never heard of such a thing and I travel a ton.

My wife had a horrible time getting it figured it out as I was on-board trying to get seats all together for us so I could help with the kids.

Flying with a bunch of little ones is tough, even when things go smooth.

Finally, she got on as the last one on the flight.

The flight was great and attendants cheerful.

No surprise there.

When we arrived in Orlando, the two main bags did not show up.

Uh oh.

We went to baggage claim and found out they were in Ft Lauderdale because they have been miss-tagged and attached to their ticket.

A hassle but a solvable problem….

There were no flights from Ft Lauderdale to Orlando, so they wanted to fly them through another airport and have them arrive the next day.

It was only noon.

We had flown in early to make sure we didn’t have any issues and if we did, we had time to fix them.

I asked why they couldn’t “courier” them as it was only a 2.5-hour drive from Ft Lauderdale to Orlando.

Answer: They were out of the “service area”.

I didn’t expect that corporate-speak BS from Southwest.

I own a company.

I know that “service area” is not the truth.

The real reason is cost.

As I kindly but firmly shared I would not accept that answer, they started making calls.

The agents tried to share with each other what the cost was.

I could see it plain as day as they passed a note back and forth trying to keep it from me.


That was the cost that was keeping me from my bags.


Not smart to try and keep something from a client.

Not classy.

Not transparent.

Not good to brag about “transfarency” when this is allowed.

Definitely a training opportunity as no one wants to have something done in front of them but tried to be passed off as secret.

Then magically they said they had a solution.

They had found another route to get the bags in time.

I hesitated because if the bags did not come in that evening, our plans, all our passes, meals, etc. at Disney on Mother’s Day would be ruined.

I asked, “was the flight going to have time to get my bags on the plane?”

Yes! They assured me it would.

I reluctantly agreed.

BIG mistake.

I called that night and found out the bags were not coming.

My gut was right.

The connection was too tight (the agents knew this and I didn’t push hard enough) and my bags didn’t make it but the agent assured me they would come tomorrow morning.

Next morning, we call.

Bags arrived…

In Ft Lauderdale.


The tag was never taken off and a proper tag put on, so they reshipped them to the wrong airport again.


I keep calm but now know that all our plans to go to Disney are shot.

All the fast passes.

All the meals.

Mother’s Day will be spent shopping for necessities for me, wife and 3 kids.

Your welcome honey! Happy Mother’s Day!

Who knows when we will get our luggage, so we bought a few days’ worth of items as we were not going to skip another day of Disney.

4 hours later we finally get to go out to eat with our family.

I step away from a meal with my kids to call back and check on luggage.

There is no easy way to track or for baggage claim to track where luggage is at in mid-transit.

This is a huge opportunity for improvement to your logistics systems by the way.

When someone has lost luggage, they want to know where it’s at and having to keep calling and checking is a huge hassle and not customer friendly.

So, I call and say the luggage should have arrived.



Are you kidding me???

This must be a sick joke.

How is that even possible?!?!?

Answer: Tags were left on the bags. No new tags o the bags. It shipped back to the original place that an agent had tagged them to.


Not once did I shout or curse at the people on the other line as I know it was not their fault.

And that is not how my faith or parents taught me to behave.

But boy am I upset.

Three times it was shipped to the wrong address.

And not because of weather or some unforeseen act of God.

Because of errors that employees had made and processes that were not in place or followed.

This to me is not acceptable on any level.

And even after the first error was made, it all could have went away for $208.

Two hundred and eight dollars just created my worst travel nightmare.

Insane and a great example of penny wise, pound foolish.

Now I have my fingers crossed and I am praying we get the luggage….

And later that night at 10:30 PM, our bags finally arrive.

Now I am tired.

I am stressed.

So is my whole family.

I have been the one planning what is supposed to be a magical trip to Disney for my family.

And it has become one huge stressor and frustration after another.

Now the cherry on top of the sundae.

I am scheduled later that week to speak at a big conference on relationship building and customer service.

My wife and babysitter are now flying home by themselves with our 3 young girls.

They get to the airport and there are huge lines.

Apparently, there are some computer system malfunctions involving luggage and Disney that are creating some issues.

Not a huge deal but the time is getting cut a little close.

So, my wife sends the sitter ahead to the gate so she doesn’t miss her flight and to let them know a woman with 3 kids is on her way.

The gate agent assures our sitter that she still has 15 minutes before the door will be shut.

Then 3-4 minutes later promptly tells her that the plane is leaving and that she needs to go to the desk to re-book.


My wife gets there 2 minutes later and can still see the plane at the jet-way.

She asks our sitter why she didn’t get on. Why can’t we get on the plane?

She says the agent had said we had time and then never gave me an option to get on. I thought we still had 10 minutes.

Now I realize that I wasn’t there to witness this but I have experienced similar instances of this with other airlines.

Passive aggressive moves.

Where a little communication, kindness, and empathy goes a LONG way.

I have been on the receiving end of amazing kindness from your many employees.

Returned computers when left on planes.

Your staff shines in most cases quite brightly.

This was an instance of the exact opposite.

And after the experience getting down to Disney, it was icing on the cake.

Not only did my sitter miss her cousin’s rehearsal dinner that she was in.

My wife was now stuck with 3 kids in Orlando as her husband was supposed to be delivering a keynote for a client.

A long cab ride later, they arrived at my hotel and I again went to get them more necessities as the luggage made it on the flight.

They however did not.

So, to wrap it up, it was the exact opposite experience you would expect from a world class airline.

Yes. It’s all first world problems.

No one died.

Or got physically hurt.

But I can say it left a VERY bad taste in my mouth and when I used to shout from the mountaintops about Southwest, I can say that is not the case right now.

I feel more than a refund for our 5 tickets is in order.

More than covering our extra clothing bought for 5 people over a few days and necessity purchases.

I feel an apology is in order and I wanted to give you the opportunity to not only make it right, but to at least try and make me and my family happy that the errors occurred.

That is what I teach my employees and clients to do.

Go out of your way so much to make things right that the client is (actually) happy an error occurred.

That is a big ask here. But it’s what I feel is right.

I would love to have my passion and belief in Southwest redeemed and I know a company like Southwest can make it happen.


Email back to John from Southwest Customer Relations

Dear John,

Thank you for your patience as I worked to research your concerns. I wanted to speak with you personally and regret I was unable to reach you by phone yesterday and today. I appreciate the opportunity to respond via email so as not to delay our response any longer.

I’m so sorry for your family’s disappointment with your overall travel experience with us between St. Louis and Orlando on May 13 and 18. As a valued A-List Customer, you probably know that our goal is to ensure that the items you entrust into our care are loaded on the same plane you board and returned to you promptly at your destination. I am disheartened that this was not the case when you flew with us on May 13, especially since your bags and lap child (Saylor) were incorrectly associated with another reservation upon check in to begin with and your wife had to spend extra time sorting that out.

We should make every effort to reunite our Customers with their bags as soon as possible, and I apologize that we were unable to deliver your bags via courier or by flight in a timelier manner (as you did not receive the bags until late on May 14), especially if they were sent to Ft. Lauderdale in error multiple times and your encounters with our Customer Service Agents in Orlando were not indicative of the kind and professional service we strive to provide. All Southwest Airlines Employees are expected to be friendly, helpful, and, above all else, courteous to all of our Customers who are kind enough to grant us their business.

I can also understand your frustration with the lack of immediate information about your bags’ location and status while they were delayed. Currently, our baggage tracking system is operated manually as our Employees enter information about unclaimed baggage in a centralized database. This system allows each airport to perform bag searches for “like” bags and contents. We are reviewing additional options in this regard with the hope that we can implement a system that will benefit our Customers while still allowing us to focus on low costs. We include bar codes on our bag tags in anticipation of future tracking systems.

In regards to your family’s return travel on May 18, I am saddened to learn that there were long lines caused by an error with Disney tagged luggage which resulted in your wife, kids, and sitter missing Flight #1881, particularly if there was any miscommunication about the amount of time before the flight was closed. I understand that your wife advised that the aircraft was still at the gate and asked the Customer Service Agent why they could not get onboard.

To explain, if a Customer is not in the departure gate area at least 10 minutes prior to departure, the Customer may lose his/her reserved seat on a flight. In addition, as you probably know, the term “closed” does not refer to the actual door of the aircraft being closed or to the jetbridge being detached from the aircraft rather the flight manifest and other required paperwork had been completed. Once these documents are finalized and signed by the Operations Agent, they are given to the Captain for use in preparing the aircraft for takeoff. Allowing Customers to board at this point would have a domino effect on the subsequent routing of the aircraft and timeliness of its schedule. Although I was not present to witness, it appears this may have been what happened as Flight #1881 departed only one minute earlier than scheduled. Nevertheless, I sincerely apologize for the additional stress and inconvenience this caused your family and sitter, especially since Erin missed an important rehearsal dinner later that day and the luggage made it on the flight without them.

With that said, please know that I am processing a refund of each of your roundtrip tickets to go back to the credit card used for payment as a gesture of goodwill. Also, I know you were all without necessary and important items and incurred additional expenses on both May 13 and 18, and I have made our Central Baggage Services (CBS) Department aware of your situation. You can submit any receipts online that you have from the items you purchased when your family was without your luggage to CBS for reimbursement consideration. Your incident number is: [removed]. Next, select the files you would like to upload and enter a message for our CBS Representatives. You can also send your receipts to CBS by mail at P.O. Box 36663, Dallas, TX, 75235.

Additionally, I am sending each ticketed Passenger a fully transferable $100 Southwest LUV Voucher to invite you back for a more pleasant experience. These vouchers will be sent in separate emails within the next 10 business days with instructions for use.

Again, I hope you’ll accept our heartfelt apologies for letting you and your family down on this occasion along with our assurance that we are constantly working to improve and have taken your feedback to heart. If you have any additional questions or concerns, please feel free to call me directly at [removed].

John, your continued business is very important to us, and we hope to welcome you, Lindsay, Blakely, Reagan, Saylor, and Erin onboard for many years to come. Have a good weekend!

Brittany Campbell
Customer Relations Executive Offices
Southwest Airlines Dallas, Texas

Learn the Secrets to... HOW, WHEN & WHAT TO GIFT!

Join our mailing list to receive the latest news and updates from our team.

You have Successfully Subscribed!