Amare Leadership Newsletter

Put the Power of love to work

Southwest Airlines’ Slow Fade from Greatness into Sameness: A Leadership Lesson in What Not to Lose

Standing in line to board a recent Southwest flight, I struck up a chat with the guy ahead of me—a military veteran turned corporate road warrior, traveling 40 weeks a year. “You must fly a lot!” I joked. 

His resigned nod said it all. Southwest, he lamented, was becoming just another airline: assigned seats, tighter rows, and no more free bags. Even the prices, once famously lower, now rarely beat the competition. Friends were already defecting to United. He called it the first nail in Southwest’s coffin. I thought, sadly, it might be among the last.

Will Southwest Fly High Again or Crash into Sameness?

Back in 2019, guest lecturing at UCSD’s Rady Business School, I asked a simple question to demonstrate the business case for love-powered leadership: “Which airline do you love?” Southwest soared above the others—fun flights, friendly jokes, genuine camaraderie. Trader Joe’s dominated similarly in the grocery space. Why? Both radiated “Amare,” the uplifting, connecting energy of love. It wasn’t even close.

Fast-forward to today, and the in-flight joy and humorous energy that once defined Southwest is almost non-existent. It’s like expecting Seinfeld but finding CSPAN.

Losing Altitude Gradually

Southwest’s decades-long reign as a profitable, customer-beloved, low-cost pioneer didn’t vanish overnight. The shift began subtly under former CEO Gary Kelly and has intensified under current leader Bob Jordan. Employees now feel profits have taken precedence over people. The old formula was this: keep our employees happy, they’ll make passengers happy, and that will make shareholders happy. And it worked. 

Now, as one longtime SWA mechanic put it to me: “Shareholders come first, not employees. It’s all about the money.” Yes, profits soared, but at what long-term cost? The unique culture that once gave Southwest its edge—and lower prices—has steadily eroded, leaving it increasingly indistinguishable from other airlines.

Adding to the turbulence, Southwest has faced operational breakdowns—like massive flight cancellations and costly fines—partly due to underinvestment in repairing and upgrading its aging fleet. When short-term profits dominate decision-making, critical long-term investments often get overlooked, and passengers feel the impact firsthand.

Dealing with Pressure from Above

Boards, venture capitalists, and investors often push for quick profits. What to do? Show them hard data proving that valued, happy employees consistently create loyal customers and sustainable profitability. Reinforce this with compelling examples of companies that have thrived precisely because they prioritized culture and people. Make it clear: short-term gains are seductive but fleeting; genuine value endures and multiplies. In short, demonstrate clearly how being love-powered pays off. 

  • What makes your culture special—and is it protected or neglected?

  • Where do short-term gains threaten your long-term vision?

  • What is your formula for happy shareholders, customers, and employees?

7 Amare Action Steps to Sustain Your Uniqueness (and Avoid Crashing into Sameness)

1. Tell the truth. State your values and vision and show how your decisions align with them (or not, and why). Make sure your Board is, well, on board.

2. Reclaim your distinctiveness. Clearly define and fiercely protect what makes your organization uniquely valuable. Tie it to your bottom line.

3. Prioritize your people. Invest in visible initiatives that show genuine care for employee well-being and reinforce their commitment to your mission and vision.

4. Keep employees informed and engaged. Implement transparent communication channels to foster trust and alignment with the company’s values.

5. Resist short-term thinking. Courageously choose long-term, value-aligned strategies over immediate profit pressures, with support from your Board and investors.

6. Elevate self-awareness. Regularly assess your own biases and assumptions to stay aligned with your core values.

7. Recognize and reward value-driven behaviors. Highlight and reward actions aligned with the company’s core values, promoting a culture of appreciation and motivation.

Rise Above the Race to Sameness

Southwest can still reclaim its magic—if it fully commits to love and authenticity again, what I call the Amare Way. And this isn’t just about Southwest; it’s a call for all leaders. By nurturing your unique culture, valuing your people, and resisting sameness, you’ll achieve lasting, rewarding success. 

Champion love over chasing profit margins, authenticity over fast rewards, and culture over becoming just another commodity. That’s how to build an organization that not only excels financially but also profoundly enriches lives.

Let’s all fly high again, powered by love.

Moshe

Flourish as a Leader with the “Strong Start” Coaching Program

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Today’s Amare Wave Wednesday Quote

The business of business is people. Yesterday, today and forever. 

— Herb Kelleher, cofounder and longtime CEO of Southwest Airlines

   

Click here and read more Amare Wave Wednesday newsletters on related topics:

5 Amare Ways to Spring Forward & Grow Your  Seeds of Greatness into Your Full Potential

Remember the Seminar that Got You So Inspired? This is How to Keep that Positivity and Not Lose it All to the Daily Grind 

Align Your Words, Actions, and Values: The Amare  Leader’s Imperative

The Cost of Winning at All Costs: Business as War vs. Business as Love

How the Best Leaders Stay Open-Hearted Under Pressure

   

Original article published on Inc.com.

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I'm Moshe engleberg

Moshe Engelberg, Ph.D.

Hi, I''m Moshe

I’m here to help you improve as a leader—as your highest self—with clarity, courage, and love.

Yes, I’ve earned three advanced degrees, advised world-class organizations, taught at several universities, and coached extraordinary leaders.

And what matters most is this:

I will see the greatness in you—maybe before you do. I will help you tap into your full power and boldly take inspired action that uplifts your organization for good.

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