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Southwest Airlines Winter Meltdown Identifies 3 Red Flags For Entrepreneurs

Twas the week of Christmas and all throughout the country, chaos ensued …

I’m confident that the Southwest Airlines meltdown of the 2022 holiday season will go down in history and be leveraged in case studies for years to come.

For me, and like so many others across the country, I’m taking Southwest’s meltdown personally. On the 16th of December the entire Jones crew traveled to Indiana via Southwest to attend the annual Hayden Family Breakfast. It was an impromptu trip, and I had to make arrangements to fly back to Arizona solo on the December 20th to make good on a work commitment to a client. The plan was for the rest of my family to fly home to Arizona on Christmas eve. It’s sad and frustrating to say, as I’m typing this - they still aren’t home. Their original flight got canceled and moved to December 26th. Yup, that means despite our planning, we were unable to celebrate and engage in our regular Christmas day traditions together. Then as my husband and 7-year-old son prepared to catch their rescheduled flight on December 26th, reports of delays started coming through and eventually that flight was canceled too. Even though that cancellation happened on a Monday, the earliest flight available to them was the following Saturday (December 31st).

Allow me to paint the picture as vividly as possible: because of Southwest’s scattered operations, I spent my first Christmas in 42 years completely alone, my family has had to deal with hours of being on hold trying to talk to someone at Southwest, we’ve had to deal with the stress of navigating travel delays and two last minute flight cancellations, we’ve been forced to take on the financial burden of paying for a rental car for an additional week and living with the emotional angst of being separated for 11 days during the holidays.

There are at least three red flags entrepreneurs can look for in Southwest’s very public meltdown as it relates to their own operational sustainability and I’ve curated specific BOSS™ Behaviors they can take to embrace a shift from chaos to order, if those red flags look familiar.

Reliance On Outdated Systems

Winter storm Elliott exposed Southwest’s failure to address issues with the legacy systems running their business operations. While the other airlines are mostly functioning business as usual after rebounding from the storm, according to CNN Southwest is responsible for 84% of the disrupted flights this holiday season.

Why? Because reportedly Southwest has been using the same tech to run their operations since the 1990s.

While consulting with a client that’s been in business for over 25 years, I discovered that they still tracked most of their essential operation metrics related to new client on-boarding via Excel. Now while I love a good spreadsheet, the tech advancements of leveraging a CRM to execute and track your on-boarding process can provide automated solutions to help you run your business vs. the manual processes of the past.

What worked in one season will not always work in the next.

Don’t be like Southwest and continue to run your business with outdated systems - shift into the practice of innovation instead. Strategically review your operations and update your tech, structures, methods and practices to increase efficacy, efficiency and sustainability.

BOSS™ Behavior - Systems Audit: Every 6-12 months do a deep dive of your systems to identify issues and gaps that need to be addressed. Document your findings and assign deadlines and the appropriate resources needed to resolve them.

Waiting To Take Action

As someone that was born and raised in the Midwest, I know it snows every Winter. And knowing that I juggle several contingency options when planning to travel back home in the Winter, especially around the holidays. Surely this most recent Winter storm didn’t take Southwest by surprise either, but their readiness and reactiveness were clearly insufficient.

In my Assistant Vice President role at JPMorgan Chase, the majority of my responsibility was looking for and predicting potential risks to the organization and strategizing solutions to avoid or mitigate those risks. I’m sure that Southwest has similar red flag waivers - and yet those in charge waited until they were embarrassed by this very public meltdown before taking action to invest in better systems.

As a small business owner or solopreneur, you cannot afford to wait to take action to address the operational gaps that you know about. The devastating impact to thousands of travelers across the country could have been minimized if the executive leaders of Southwest had acted sooner.

In my book The BOSS™ Shift I walk readers through an exercise of calculating the cost of not taking necessary action in their businesses. As far as knowing what to address first as you shift from being solely reactive to incorporating more proactive methods, you can prioritize your actions by:

  • Respecting any internal or customer-facing time sensitive deadlines

  • Identifying any major gaps in your operations that require immediate attention

  • Following the flow of your customer’s journey, and make significant improvements each step of the way

BOSS™ Behavior - Calculate The Cost: Take a few moments to think about and journal what it will cost you and your business, if you fail to take action on known issues. Then reflect on if it is a cost you and your business can afford to pay.

Falling Down On Customer Service

Often small business owners and solopreneurs invest in the tools, tech and resources geared toward customer service too late - after a disaster strikes. Bottom line, investing in your systems is investing in excellent customer service - thus yielding high ROIs in the form of revenue, referrals and brand reputation.

You’ve already read about my experience with Southwest and sadly in this season it’s not a unique story. Social media is full of examples of Southwest dropping the ball - these underwhelming experiences are being shared by frustrated pilots, exhausted flight crews and weary travelers.

“Ryan Green, Southwest’s Chief Commercial Officer, said in an interview the airline is taking steps such as covering customers’ reasonable travel costs - including hotels, rental cars and tickets on other airlines, and will be communicating the process for customers to have expenses reimbursed.” It’s safe to say that this post-meltdown response will be more expensive than many of the proactive customer service focused solutions that could have already been in place. While no business is perfect, a shift is needed toward valuing the investment in solutions that will support the retention of satisfied and loyal customers. The time, energy and expense it takes to resolve customer issues with your brand in an attempt to repair the relational equity that has been damaged can be costly in a multitude of ways.

BOSS™ Behavior - Brain Dump: Do a brain dump of the potential issues that could arise for your particular customers. Then choose one issue and develop a solution to implement to combat that particular issue in your business in order to deliver excellent customer service.

Resolving The Red Flags

Like I said earlier, Southwest’s meltdown is personal - it has met me at the intersection where my life and work collide. I know what it’s like to see red flags, yet feel too scattered to even think about, let alone put strategy into action to resolve them.

While I lean towards taking a more proactive approach to solving problems, I recently connected with a friend of mine that considers himself a reactive guru. As we talked, we came to the conclusion that problems don’t require just proactive or reactive solutions, they require both / and.

So maybe the red flags in your business are on the horizon, or maybe you’re already in crisis mode. In either case, I can help you identify a solution that will be a catalyst for the transformation you’re seeking in your business.

Click HERE to schedule a Connection Call so we can discuss the support options available to embrace a shift from chaos to order.


La’Vista Jones is a business consultant, professional speaker, host of the BOSS™ Talk podcast and published author. Her latest book, The BOSS™ Shift: Do What You Love, Without Sacrificing Yourself To Do It, is anchored in implementing her signature framework that focuses on battling overwhelm with systems and self-care.

1 Comment

Dec 30, 2022

This is an outstanding use of a very public corporate faux pas, in spite of what it cost you and your family personally, during this holiday season, to leverage your solution-based business and your book as well as to attract future clients. Most people would’ve used this time to complain, instead you offered solutions and alternatives, which puts you light-years ahead of most. Maybe Southwest will consult with you, especially since they cost you and your family the holiday experience you held most dear, because of their severe breaches of duty. I hope the great things come from this unfortunate series of events for you and yours.

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