10 Months Into Job, Southwest’s C.E.O. Faces a Giant Crisis

After Southwest Airlines made it through Thanksgiving with few flight cancellations, Bob Jordan, the company’s chief executive, was in a celebratory mood. At a meeting with Wall Street analysts and investors this month at the New York Stock Exchange, he said the company’s performance had been “just incredible.”

But a few weeks later, over the Christmas holiday, Southwest’s operations went into paralysis, forcing the company to resort to mass cancellations. The debacle has raised questions about Mr. Jordan’s performance and has prompted employees and analysts to ask why the company has been slow to fix well-known weaknesses in its operations.

Other airlines fared far better during the extreme cold weather over Christmas weekend than Southwest, which after days of disruption canceled more than 2,500 flights on Wednesday, vastly more than any other U.S. airline, according to FlightAware, a flight tracking service. The airline has already canceled more than 2,300, or 58 percent, of its flights planned for Thursday.

Travelers, lawmakers and even employees are increasingly demanding answers from Southwest and Mr. Jordan. While the company has repeatedly apologized for its performance, it has provided few details about how things went so wrong and what it is doing to right its operations. The company said on Wednesday that Mr. Jordan and other executives were not available for interviews.

In a video posted on Southwest’s website late Tuesday, Mr. Jordan, who became chief executive in February after three decades at Southwest, implied that the airline was caught out by a rare event. “The tools we use to recover from disruption serve us well 99 percent of the time,” he said, “but clearly we need to double down on our already existing plans to upgrade systems for these extreme circumstances.”

Southwest has known for years that computer systems that manage customer reservations and assign pilots and flight attendants to each flight needed improvements. Union leaders and even the company’s executives have acknowledged that the systems struggle to handle large numbers of changes when the company’s operations are disrupted.

Disruptions can have a cascading effect on Southwest’s flights because it operates a point-to-point system, in which planes travel from one destination to another; other large airlines use the hub-and-spoke system, with flights typically returning frequently to a hub airport.

Southwest is now trying to piece together its operations after many of its crews and planes were not where they were scheduled to be because of earlier flight cancellations, the company said in an emailed statement to The New York Times. Because the company’s operations have been so thoroughly upended, the effort is expected to take days. To get crews and planes in the right places, Southwest had to reduce its schedule. This should allow the airline to bring crews to the airports where they are needed.

In his video on Tuesday, Mr. Jordan appeared to acknowledge that Southwest’s model was susceptible to breaking down under stress. “Our network is highly complex, and the operation of the airline counts on all the pieces, especially aircraft and crews remaining in motion to where they’re planned to go,” he said.

The company has spent years trying to overhaul its technology systems, but this latest crisis is expected to ratchet up the pressure on Southwest and Mr. Jordan to make progress faster.

Union leaders said they had run out of patience with how the company had been updating the technology systems.

“We’re at the point where we’ve given him enough grace,” Michael Santoro, vice president of the Southwest Airlines Pilots Association, said in an interview, referring to Mr. Jordan.

Transport Workers Union Local 556, which represents Southwest’s flight attendants, issued a statement agreeing with the pilots. “It is not weather; it is not staffing; it is not a concerted labor effort; it is the complete failure of Southwest Airlines’ executive leadership. It is their decision to continue to expand and grow without the technology needed to handle it,” the union’s president, Lyn Montgomery, said.

These statements stand out because Southwest has generally had very good relations with most of its labor unions. After the meltdown, labor leaders have grown increasingly critical of the company this week. The pilots group, for example, expressed frustration that the company had not yet shared its plan for getting its operation back to normal, something it typically does after disruptions. “We have heard zero,” Mr. Santoro said.

In the last few days, union officials, pilots and flight attendants have complained to journalists and on social media that crew members have often had to wait hours to be assigned to their next flight or be directed to hotels where they could spend the night.

Customers have also expressed intense frustration with the airline, saying it had become impossible to get any information from the company. Some people have said they waited hours at baggage and ticket counters and gates to speak to Southwest agents. Others have tried and failed to get through to the company by phone or online.

Howard Tutt came to Chicago’s Midway airport on Wednesday to try to retrieve a bag his son had checked for a flight to California that was ultimately canceled. He said he had waited hours with other customers to speak to someone to no avail. Nearby, dozens of bags were waiting to be reunited with travelers outside Southwest’s baggage office and near its carousels.

“He had to leave in the middle of Christmas dinner because they told him the only flight he could get on was at 9 p.m. on the 25th,” Mr. Tutt, 61, said, referring to his son. “Then he got to the airport, checked his bags and was delayed for six hours before they canceled the flight.”

Mr. Tutt, a resident of Orland Park, Ill., said the family had tried a variety of approaches to locate the bag, which contains Christmas gifts for his son’s girlfriend and her family. “We’ve emailed, tried via chat message, and called but cannot reach anyone.”

Analysts said that, as cancellations piled up, Southwest found itself in a dire position in which it needed to almost start from scratch to rebuild. “You’ve lost control of what you expected the operation to be,” said Samuel Engel, a senior vice president and airline industry analyst at ICF, a consulting firm.

The question that will loom over the company for a long time is why Southwest’s system broke down while those of other large airlines held up relatively well. Analysts say Southwest’s point-to-point network, which is quite different from the hub-and-spoke system used by its peers, made it harder to restart operations.

But they also say Southwest’s technology, despite yearslong efforts to modernize it, was lacking. And Mr. Jordan is likely to be asked why he didn’t do more to make the systems strong enough to deal with weather and technology disruptions, which have dogged Southwest in recent years, including two mass flight cancellations and delays last year.

Though Mr. Jordan has been chief executive for a short time, he has long been a member of Southwest’s senior leadership team, which would have given him plenty of opportunity to understand the company’s strengths and weaknesses. He started at the company as a computer programmer, helped develop its frequent flier program and aided in incorporating the planes and crews of AirTran Airways after Southwest acquired that company.

Robert W. Mann Jr., a former airline executive who now runs the consulting firm R.W. Mann & Company, said Mr. Jordan was “in the hot seat right now.”

But analysts were skeptical that Southwest could change quickly. They say the company’s management suffers from “Southwest exceptionalism,” or a stubborn belief that its unique approach to running an airline is best. Even though Southwest has it origins as an upstart taking on sleepy incumbents, analysts say its decision making can move at glacial speeds. “The airline has always been very cautious about change,” Mr. Engel said.

Southwest’s approach works well much of the time, and it has contributed to the company’s strong financial performance over the last five decades, analysts say. It allowed, for instance, for planes to be used more quickly for their next flight. Longtime shareholders have done well. Southwest’s stock is up 217 percent over the last decade, outpacing the wider stock market and its best-performing rivals. But this month, Southwest’s stock, down by nearly a fifth, has performed worse than the market and its peers.

There is no evidence that Mr. Jordan is vulnerable. But poor crisis management has severely weakened other airline executives.

In February 2007 JetBlue experienced a meltdown when the airline did not act as quickly as its peers to cancel flights, hoping an ice storm on the East Coast would not have affected air travel as much as it did. At one point, nine JetBlue planes filled with passengers sat on the tarmac at Kennedy International Airport for six hours.

David G. Neeleman, JetBlue’s founder and chief executive at the time, who was also a former Southwest executive, said he was “humiliated and mortified.” Months later, he agreed to step down as chief executive.

Mr. Neeleman did not respond to requests for comment.

Robert Chiarito contributed reporting.