Make 2023 the Year You Escape Expense-Report Jail

Finance executives cited delays in expense-report submission as a top challenge for their companies in a 2022 survey by travel-expense-management company TripActions. For employees, tardy or sloppy expense reports run the risk of reprimands or worse from the bosses CC’d on those your-report-is-overdue emails. Delays can also hurt your personal finances if you don’t have a corporate card and potentially harm your credit score if you do have a corporate card and are late with payments.

Expense-report anarchy isn’t a unique problem, especially as business travel resumes. It’s a chore few employees relish, especially given more pressing work priorities. Who hasn’t tried to decipher that barely legible scrawl of the handwritten taxi receipt, searched desperately for that itemized bill from the pricey dinner with clients or tracked down a hotel receipt the chain swore they would email?

Vivianna Winterbottom, customer success manager for a financial-services-software company, says she spent part of her time off last week filing three expense reports from recent work trips. “Real” work took precedence during her last week in the office, she says.

Ms. Winterbottom, who lives in Atlanta, also approves expenses. She says she can’t believe how some of her co-workers get the chore done before they’ve even gotten home from a trip they took together.

“I’m landing and I’m already getting their expense reports,” she says.

Ben Schein, senior vice president of data for a software company, traveled to Singapore and Australia for work for 10 days in November. He started getting reminder emails about the expenses before Christmas because more than 30 days had lapsed.

Mr. Schein, who lives outside Minneapolis, says he religiously uploads receipts to his company’s travel-management app while on the road. The logjam comes when he must track down a missing receipt, especially from hotels that don’t send promised receipts. For the international trip, he had the receipt from one

Marriott

in Australia but had to call the front desk of the other for a copy of his bill.

He filed the expense report—which still had 163 red flags appended by his company’s expense software, mostly for overdue expenses—on Dec. 19, the night before his family left on a holiday trip to Cancún, Mexico.

Frequent flier Michelle Stephens is a longtime healthcare executive and a consultant in Rapid City, S.D., who coaches executives on topics including productivity.

Mrs. Stephens hates filing expense reports but says developing good habits around receipts and other elements is the ultimate timesaver. In extreme cases for chronic late filers, it could even save your job, she says.

Mrs. Stephens’s hack: scanning or photographing receipts as soon as they arrive. Note key details about the expense in the app or any emails you send yourself about it.

She and other frequent fliers say the key to staying on top of travel expense reports is to use your company’s expense reporting app as you go. She’ll even take the socially awkward step of photographing a receipt during a business lunch.

“What I hate worse is digging through a pile of three trips’ worth of expenses and trying to sort them and organize them and go back and even remember what you did,” she says.

Haphazard receipt collection isn’t a problem for Jessica Leight—getting receipts into the system is. She stores them in her wallet until it bulges, when she moves the receipts to an envelope from whatever hotel she’s staying in.

The issue crops up when Ms. Leight, a development economist with the International Food Policy Research Institute, gets home. She travels to countries where electronic receipts are rare. She collected 15 tiny paper receipts from a recent five-day trip to Rwanda. She must tape them to full sheets of paper and scan them for uploading to the report.

“That usually breaks my scanner,” says Ms. Leight, who lives in Farmington, Conn.

She was still working on the report days before Christmas.

“Doing it within a week [of the trip] is the goal for my future,” Ms. Leight says.

Ms. Winterbottom in Atlanta is determined to join the ranks of speedy expense-report filers.

“For 2023, I’m telling myself now that I’m going to definitely make sure I get on that plane, I open my app and start creating the report, start populating it,” she says.

Every year Alyssa Billups, who travels to events frequently in her job in influencer marketing for DirecTV, resolves to start expense reports on her flight back from a work trip. Every year it doesn’t happen.

“I’m always dead,” the 30-year-old New Yorker says. “I’m like, whoa, I don’t even know my name right now.”

At the end of the year, she had five emails about tardy expenses and was staring down the deadline for an expense report for a multicity trip.

“I definitely want to get better, because it just makes your life easier and less cluttered at the end of the year,” she says.

You and me both, Alyssa.

Write to Dawn Gilbertson at dawn.gilbertson@wsj.com