How to tell your colleagues they need a vacation: It's not just saying 'you look tired'

Aye Moah, CEO and cofounder of Boomerang, on vacation with her husband and son in the Grand Canyon.
Courtesy of subject

When Aye Moah recognized one of her Boomerang co-founders was burning out during the pandemic, she and her team decided to intervene. Sure, even though travel was off the table, maybe he could take the week off and just play video games at home. They'd even send over lunch. Anything to get him to take a break.

Moah, also the company's CEO, has learned to be more proactive about recognizing signs of employee burnout. "We've been working on this company for 11 years," she tells CNBC Make It. "It's a marathon, not a sprint. We know that when people get past the point of burnout and try to recover, it has a much bigger impact on the business than if people are taking care of themselves."

She's hopeful Boomerang can help people take breaks and manage their time. The tech company is most known for its email and productivity tools, like an inbox plug-in to delay-send messages. Moah uses it when she's on vacation — if she has work idea she doesn't want to lose, but doesn't want to get in the weeds while she's on PTO, she'll draft a note to auto-send after she's back.

As for paid time off, Boomerang offers employees 17 vacation days to start, plus one extra day per year of service. Here, Moah, 40, explains why she never stops thinking about work, a better way to tell employees they're burning out and how family loss changed how she values time.

Why she "disappears" from work after big deadlines: I tend to schedule a vacation after a product launch, because they're so exhausting. I get really tightly wound up before one. So after a launch, I'll spend a week in the office to make sure everything is still going smoothly. Then the second week after a launch, I'll go somewhere completely off the grid. My team knows — "Moah will disappear the second week after a launch."

Why she still thinks about work on vacation: I'm a founder, so I never really stop thinking about work. I know people are like, "Oh, you're supposed to just enjoy your vacation and not think about work." That's not really who I am. So I'll be hiking or playing with the kids and still thinking about how a launch went. It's a way to process what happened at a lower intensity.

Processing things from a farther distance helps me see what went well. Otherwise, if I were still in work mode, I would sit and stew about what could have gone better.

Then, when we're all back, our team does a post-mortem to talk about what to do differently the next time, with a fresh perspective.

How she tells employees they need to take a vacation: As a manager, there are a few signals that someone needs to take a break. You might realize they haven't taken PTO in 18 months. Or you can tell if someone has lower energy or isn't as engaged.

Usually when people don't take you up on it, it's because they're concerned about delaying a project or putting more work on their colleagues, so you have to reassure them. I would hope that, if you're a direct manager, you have a close enough relationship to encourage them to take time off.

It's not like saying, "Hey, you look tired," because that's not a good conversation. It's more like, "Hey, you haven't taken a vacation in a while. We have flexibility in the schedule before this big project. And this other person will also be working on it. So you won't be impacting anybody. What do you think?"

How loss impacted how she values time: I lost my brother when he was 23. That left an imprint on me that you never know what tomorrow will bring. You don't know how long you have left on Earth. So try to see every day, every month, every year as precious time. I'm a very ambitious person. I want to succeed in my career and make progress. But at the same time, that's not everything.

What she'd tell her 25-year-old self about taking time off: Don't wait for a perfect moment to take it – there is never a perfect moment. My co-founders and I started building this company when we were in our 20s. We were paying off student loans and had no money to go anywhere. But we took every chance to take lower-budget trips we could afford. Now that we're a little older and the company's more successful, we have the resources to travel. But we also have kids and more responsibility. So it's hard to balance having the resources in terms of time and money, versus responsibility.

This interview has been edited for length and clarity.

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This 27-year-old former NYSE trader went from making $12,000 to $650,000 in 4 years
27-year-old former NYSE trader went from making $12,000 to $650,000 in 4 years