What to Do About a Boss Who’s Pinging You at All Hours

Business English with Natasha

Feb 13, 2023

PHOTO ILLUSTRATION BY ELENA SCOTTI/THE WALL STREET JOURNAL, ISTOCK(2)

What to Do About a Boss Who’s Pinging You at All Hours

There are ways to conquer the torrent of round-the-clock messages

By Rachel FeintzeigFollow

Feb. 13, 2023 12:01 am ET

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Ding! Your boss has a question, an assignment, a fleeting thought. And she wants a response. Right. Now.

“Months later, I would get a notification and I would still get that nervous jump,” Nate Shalev says of a previous boss with a penchant for 3 a.m. emails, as well as midday texts and calls when notes went unanswered for an hour.

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Working for people who transfer their every whim via the stroke of a keyboard—and consider your response time a proxy for productivity—can be maddening. When you’re always bracing for interruptions, focus feels impossible. Being checked on every half-hour doesn’t exactly breed confidence, either.

Can you train a boss to slow the torrent of messages? And are there ways to pretend you’re always on, even when you aren’t?

“There’s a power dynamic at play,” says Khe Hy, the founder and chief executive of RadReads, an online education company that offers productivity classes. Lobbing off another random request, the boss reasons, “I’m allowed to make your life difficult if it makes my life easier,” he says.

Sometimes the higher-up might not be thinking at all. When Mr. Hy was working in financial services, about a third of the supposedly urgent outreach sent by one boss boiled down to, “Can you send me the link for the fantasy-football login?” or “What was the name of that restaurant in New York City, again?”

Standards and shortcuts

First, figure out what the standards really are. Does your boss expect, or even want, you to respond to that random article link he shot off at midnight while rocking his baby back to sleep? Mr. Hy recommends categorizing the types of messages you get—from emails assigning tasks to musings sent over the weekend—and asking your boss when he expects a response for each type.

If the answer is ASAP, always, try an email filter. Mr. Hy created one in a prior job that sorted emails from two of his bosses into a folder he labeled VIP. He included emails where he was in the “to” recipient field, not the “cc” one. The folder was the only one in his inbox, making it easy to spot when important requests came in.

Don’t want to be glued to your email? (Or Slack, or Microsoft Teams?) You can use workflow-automation software such as Zapier to notify you when your boss reaches out. For example, Zapier can automatically text you a link to your manager’s direct message on Slack, or add the content of your boss’s email to your to-do list. Or, you can set it to alert you when your higher-up pings you three times in a row.

The app, which starts at $19.99 a month for premium features, can also set up an autoresponder for your manager’s messages, so you can automatically shoot back with, “Thanks, boss. Got this. I’ll follow up in the next hour,” says Chris Geoghegan, Zapier’s senior director of product management.

If the boss is the texting type, you can tweak your phone settings to assign your manager a specific ringtone so you don’t miss that chime.

Take back control

Then again, maybe you’re part of the problem. Many of us are so desperate to show how hard we’re working and how dedicated we are that we leap to respond whenever a higher-up beckons. But a 2021 paper found that recipients overestimated how fast senders expected replies to after-hours emails.

“Others don’t judge us as harshly as we think,” says Laura M. Giurge, a co-author of the paper and assistant professor at the London School of Economics and Political Science. The research also found that people who get emails outside work hours felt more stressed than senders expected them to feel.

If you’re always texting your boss back during dinner, you’re reinforcing the idea that the manager can page you at all hours, says Nancy Halpern, a leadership consultant who’s worked with companies such as Novartis AG and Bank of America Corp.

“Exert a little control over your own life,” she says.

Glance at the text, and if you think it can wait an hour, finish eating. If it’s superurgent, she advises to call and offer, “I saw your text and wanted to respond. I’m just finishing up dinner. Can I call you in an hour?”

Doing so trains your manager that you’re present, calm and fully registering the request, while retaining some of your power (and reminding your higher-up that you have a life outside work.)

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What are your tips for slowing an avalanche of messages from the boss? Join the conversation below.

Try to pre-empt your boss’s last-minute missives by tracking patterns, Ms. Halpern says. Does he tend to spam you with messages on Friday afternoons? Is one client stressing her out? Contact your boss a few hours before the flood usually starts, noting that you want to make sure you’re addressing her priorities.

Bryce Anderson once got caught up in the allure of a startup-founder boss who routinely sent him emails in the middle of the night. The fact that the leader seemed to work crazy hours and not sleep struck him as cool, he says.

If Mr. Anderson happened to spot a 2 a.m. email, he’d jot off a reply right away. After about a year at the company, a colleague told him that the founder had confessed to writing the emails during the day and scheduling them to send at night so he looked more productive.

The revelation felt like unmasking the man behind the curtain in “The Wizard of Oz.” Mr. Anderson vowed not to work like that again.

Now the co-owner of a Chicago video-production firm, he uses schedule send to ensure the occasional email he types out after his kids go to bed is delivered during daytime hours.

“We’re a company that signs off at five and signs on at nine,” he says.

Write to Rachel Feintzeig at Rachel.Feintzeig@wsj.com

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