How to communicate with airlines when they screw up — and actually get your money back, according to a flight expert

• Getting compensation from an airline after a delayed or canceled flight can be challenging.
• Flight expert Gilbert Ott has a few tips for getting your money back if you're entitled to it. 
• Ott said to skip the sob story and the AI chatbot. Focus on proof and don't give up, he added.

Five years ago, Gilbert Ott flew from London to New York on a budget airline. The flight was delayed until the following day because of mechanical issues, he told Insider. European Union rules entitled him to full compensation.

The airline didn't pay Ott back at first, but they didn't know who they were dealing with. 

Ott flies 200,000 miles a year, and a decade ago, he started a blog called God Save the Points focused on travel efficiency. He also consults airlines on a case-by-case basis on work including more transparent rewards and improved passenger communication. 

Fliers like Ott have plenty of reasons to be frustrated, with global airline delays and cancellations rising for years without hope of a turnaround. Insider previously reported that these problems stem from staffing, including a lack of pilots, mechanics, and air traffic controllers, and extreme weather conditions exacerbated by climate change.

Although airlines are juggling complexities passengers may not always see, Ott said that we, as travelers, often have valid complaints. 

"We know what gets in our way, what screws up our flights, and what frustrates us with pricing or transparency," he said. "And quite often, we're spot on."

Compensation rules for delays and cancellations vary by country. For example, aside from circumstances when the airline is not at fault, such as weather or air traffic control, airlines in Europe are required to compensate passengers for delays more than three hours long. However, in the US, there are no federal rules regarding compensation, so the airlines each have their own rules. 

So once you have a handle on what happened with your flight and what local rights you have to compensation, it's time to get in touch with the airline.

Skip the AI chatbot

Never use chatbots to communicate with the airline, Ott recommended.

"So few are actually human-driven, and all of them are going to advise you to end up contacting somebody if you have a real problem," he told Insider. "People waste so much time and energy with airlines, all for it to be read by AI and instantly denied until you send it seven more times."

Instead, Ott recommended reaching out to the airline via email and copying an executive, like a CEO.

"You want to make sure it gets to somebody who will read it," he added. "A CEO's email address will generally be monitored by several different people, and they will each be able to act as a liaison on behalf of leadership."

Ott said nearly every airline issue he's had resolved was sent to an executive-level email address. 

"These issues were not tied to my blogging career — just as a Joe Schmo who flew in your airline," he said. 

Skip the sob story

When you're drafting your email, Ott said to focus on the facts about what went wrong and less on the emotions.

"It's one thing to say, 'I was going to my wedding, and you ruined my wedding.' But that's one line," he explained. "We don't have to go into, 'The bridesmaids showed up, and I wasn't there,' or 'The cake was there, and I wasn't there,' or 'The hotel that I was supposed to go to charged me for a night.'"

Ott said these details don't help. Instead, explain what happened, provide proof, and then very quickly state how it impacted you, according to Ott.

"Say, 'I would like to understand how you're going to make this right. Otherwise, I don't plan to fly again,'" he added. 

Get proof

When an airline is responsible for compensating you, providing proof is key to getting your money back.

"The more you can share or ensure that you're right, the better," Ott told Insider. "That's where documentation comes in."

For example, if your flight is canceled while you're at the gate, ask a gate agent to write up the incident, he suggested. They'll likely say no, but it's worth trying.

"I don't blame them. Most of them are contract employees and really don't feel like they deserve to hear from people the way they do," Ott said. 

He also suggested documenting the flights that did take off that day by using free online tools like Flight Aware. This documentation will be helpful if the airline tries to claim that the cancellation or delay is due to extraordinary circumstances. For example, if the airline claims the flight didn't take off due to weather at the arriving airport, proof that other flights to the same destination did depart could help your case. 

Keep pushing

Even with an executive email and proof of the issue, Ott said it can be challenging to get compensation from an airline unless you follow up multiple times. 

When Ott contacted the budget airline that delayed his flight to London five years ago, emailing once with proof wasn't enough — his claim was initially denied, he said. After several emails, Ott told the airline that he would reach out to AirHelp, a service that legally represents passengers all the way to court for a fee or a cut of the earnings. He said the threat was enough for them to approve his claim. 

"Don't just take their advice of being ineligible, because most of the time it's just an automated lie designed to flick fleas," Ott advised. "The more people an airline can convince that they aren't due compensation, the more money the airline saves."

So if an airline denies your claim, let them know that you intend to pursue it as far as you have to, even if that means complaining to the Department of Transportation or taking the company to court.

"It's amazing how quickly things work out once you do that," he added.