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How executives approach work during the holidays

At the U.S. investment bank Jefferies, the board feared a crisis was brewing every time Chief Executive Rich Handler visited Greece in August. Handler was holed up on a yacht there in 2007, as Wall Street was unwinding its leverage in a precursor to the following year’s financial crisis, and again in 2011 in the early stages of the eurozone debt crisis.

A decade later, he was vacationing in the Turks and Caicos Islands when he received a worried call from his head of trading about Jefferies’ exposure to what was then a shadowy family office called Archegos.

“I said, ‘I’m going to have a spicy margarita and I’ll be back in about 15 minutes,’” Handler told the Financial Times. “When I get back, give me a figure, which is going to be how much money we lost. I want you to tell me everything before I get back.”

Jefferies escaped the Archegos collapse with a modest $40 million loss, while other banks had to take on billions of dollars.

“Sometimes when you’re on vacation, everything becomes clear… because you’re not as close to the situation,” Handler says. “Our team did all the hard work by correctly identifying the problem and raising it quickly. You can just look at the bigger picture and make the decision.”

Many CEOs and senior managers will have to make a similar decision this summer about how far they should cut ties with the office during their annual leave. Some advisers argue that only complete detachment and handing over of responsibilities to the team can lead to a restful break, while others firmly believe that some communication and involvement at work is inevitable.

The benefits of adequate rest are clear: several studies We link a well-rested mind and body with increased creativity, higher productivity, and a better overall mood. Hard work has psychophysiological costs (stress, fatigue, irritability) that, if not corrected with proper recovery, can begin to affect performance.

But now that remote work is the norm for a large number of professionals and connectivity remains at near-constant levels, for many senior people in business, completely disconnecting is not realistic.

It is “naive” to think that a senior executive can completely disconnect from the network for a fortnight, argues Zena Everett, author of The cure for madness and hustle and bustle.

“Obviously, it’s not good for people to be looking at their phones all the time, but if sending a quick WhatsApp message is going to help them switch off for the rest of the day, then do it,” she says.

Executive coach and author Andy Brown has a different take: That quick email check may seem harmless, but it acts like grit in your shoe, he says. “It’s not much, but it’s still irritating.”

Social norms are a big factor in the debate. Employees in France and Hong Kong don’t take nearly a month of vacation each summer, while more than half of Americans struggle to use even the standard 12 days allotted to them each year, according to a new study by travel company Expedia on “vacation deprivation.”

Company-specific cultures can exacerbate these broader norms, Brown notes.

But much depends on the individual. The people who struggle the most are the “it’s my responsibility” type of bosses, for whom vacations can seem almost like a “lack of responsibility,” she adds.

Small business leaders can be particularly prone to this. James Howard-Vyse, director of Wizzard, a small creative agency based in London, says: “As an entrepreneur, I feel like my role is to make everything work, which means you often get left at the bottom of the list, even when it comes to holidays.”

Excessive empathy (or guilt) can be another barrier, experts say.

Behaviors like participating in team calls or taking on small tasks during annual vacations often reflect a good attitude, says Janet Harvey, executive coach and author of From tension to transformation, But it’s not a good idea. Not only does it deprive executives of the rest they need, but the act of checking in can make their teams feel distrusted and micromanaged.

“The mentality of ‘my team can’t function without me’ is disrespectful. Do they really want me to believe that they have hired people who are not capable of living up to their role?” she says.

Jörg Schnelle, chief commercial officer of German fintech Riverty, admits that he likes the feeling of being “always reachable” and that logging in helps him relax.

“It’s not like I need to look at my phone all the time. I was in the jungle in Thailand for two or three days without internet and I survived… But I think if checking in doesn’t stress you out, it’s fine,” he adds.

Whatever executives decide, good advance planning is necessary, says Amanda Arrowsmith, director of people and transformation at the Chartered Institute of Personnel and Development.

Jillian Janaczek
Jillian Janaczek, who runs Porter Novelli, says the PR agency keeps a group calendar of senior staff to ensure that “if a crisis erupts, it’s clear who needs to step in.” © Pascal Perich/FT

Calendars and workflows should be set in advance, and managers should provide clear expectations about when (and when not) their colleagues and teams should communicate with them.

CIPD guidance to bosses tells them to “set a good example by taking annual leave yourself” and “do not make staff feel guilty about taking annual leave”.

Bruce Fecheyr-Lippens, HR director at HR solutions provider SD Worx, says managers should remove all notifications. “Whether it’s Teams, Outlook or whatever, just remove them. Otherwise, you know, if they’re using the computer for leisure, there’s always a trigger at their disposal, which is fatal.”

Other tips include not sending rushed emails (a one-line message can cause as much “panic and stress” as the one you’re trying to resolve); turning on out-of-office mode with clear instructions on who to contact in your absence; and blocking off half a day upon your return to tidy up your inbox.

Jillian Janaczek, CEO of public relations agency Porter Novelli, says she is “really very intentional and deliberate about setting expectations for myself in terms of self-care” at work and during her free time.

Its nine-member operating committee maintains a group calendar to clarify “where everyone is, who is out and who is covering.” That way, if a crisis erupts, it is clear who should step in.

Still, her recent vacation — the first proper break she’s taken since starting the job about a year ago — was punctuated by a company-wide volunteer day and an inevitable morning conference call, which she dealt with by informing her family well in advance.

“My family knows I work hard, but they never feel like I’ve missed out on anything because I always try my best to be very clear about where I am and what I’m doing,” she says.

When Wizzard’s Howard-Vyse takes his first two-week holiday in years in August, he intends to turn off notifications on his phone and inform his clients that he will be away.

“Letting customers know you’re not in the office seems like a big decision, almost like admitting defeat,” she says. “But actually, telling customers that there are other team members who are equally qualified to help them is probably not a bad thing.”