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Managing Digital Nomads: You gotta trust ‘em


by Richard Pooley


Unsplash Photo: Christiann Koepke

You could buy a shoe box in Mayfair...” Such was the strapline of an advertisement by ‘Locate Guernsey’ in the House & Home section of the Financial Times’ Weekend edition on 24/25 September. A bearded young man in shorts and trainers sits at a table in front of his iPad on the sunlit terrace of his villa in what, presumably, is Guernsey. He is smiling at a blonde-haired woman in a dress, her feet in the blue water of a swimming pool, her back turned to meet his loving gaze, with her sandals, magazine and glass of water beside her. The strapline continues, in smaller print: “With no capital gains, inheritance tax or minimum income requirement, it’s easy to see why more people are calling Guernsey home.”


A more sexist ad would be hard to imagine. Do those marketing Guernsey’s attractions to digital nomads - people who are able to work remotely from home, moving every so often from one country to another - think the term only applies to men? According to one survey I found on a site aimed at digital nomads - https://abrotherabroad.com/ - nearly half of them are women, though another site had the proportion as 21%. Perhaps abrotherabroad (ABA from here on) is trying to compensate for their sexist title. Or have they taken their cue from the new governing party of Italy, the Brothers of Italy, headed by a woman (a Sister?), Georgia Meloni. The surveys on both sites show little evidence of statistical rigour, not least because the definition of ‘digital nomad’ is so vague.


Here is how ABA define the term: “A Digital Nomad is any person who perform their jobs primarily using mobile technology which allows them location independence. DNs live outside their home province or state or country and change location routinely (months to years).” This allows ABA to claim “from 4000 poll and survey responses from the English-speaking community around the world” that there are “35 million DNs in the world.” So, there are no non-English speaking digital nomads? And those US Americans who move every few years from one state to another in search of a better life and decent wifi are doing something radically different from their forebears? Enough of ABA and their dodgy numbers.

The other site I looked at stated that 61% of digital nomads are married and 26% have children under 18. And they traipse around the world, home-schooling their children? Or are they really traditional expat. families who move from posting to posting and school to school every three or four years? Hey, I was one of those. And so were my parents. Okay, we weren't very digital. I communicated with my head office in London by telephone, telex, fax (remember them?) and latterly by email. My father communicated with his head office – the UK’s Foreign and Commonwealth Office – mostly by letter, courtesy of Queen’s Messengers.


Locate Guernsey’s ad is one of many I have seen in the print and online media of late. Reports on their news pages abound with stories of countries such as Barbados, Portugal and Georgia offering temporary residency permits (now dubbed ‘Digital Nomad Visas’ or DNVs). Something tells me that Georgia might have to start restricting the number of DNVs they hand out to Russians. The latest list of countries offering DNVs that I found was on https://nomadgirl.co/ (a far better site than ABA’s, boys) on September 21. It names forty-seven countries and says the list is extending fast: “The DNV has come of age.” Indeed. So, what does this mean for those businesses that employ them? One of the sites I looked at said that 83% of digital nomads are self-employed, and 17% employed by companies as remote workers. It this latter lot who interest me.


I retired from training businesspeople in how to be successful international managers at the end of 2017. I had been doing it for well over thirty years and worked as a manager myself (sales, boss of a foreign subsidiary, partner, and finally managing director). In the final decade I met an increasing number of participants on my courses who were full-time employees of a company and part of a departmental team or several project teams yet who were working remotely. The Covid-19 pandemic did not create these remote workers or their exotic subset, the digital nomad; it merely accelerated a trend.


Most employees working remotely who I have spoken to about their working lives don’t have anybody reporting to them. Sure, they have a boss or even several bosses, but they are far away and generally don’t pester them for frequent progress reports and online update meetings. Perhaps the biggest plus of remote working for them is this freedom from being micromanaged.


More interesting for me as an ex management trainer is what it is like being on the other side: a digital nomad who is the direct boss of employees in another country or even several countries, responsible for their welfare, and having to mentor, motivate, discipline, even hire and fire? What do you have to do differently from the days when your department or team were all in the same building or, at least, in the same town? How can you ensure effective teamwork when you, the team leader, are never there physically? Can a manager be hired from outside the company to run a team remotely if they have never worked inside the main office and experienced the company’s ways of doing things – its culture?

It wasn’t until recently that it dawned on me that I could find some answers to these questions from inside my own family. My daughter has worked for a feted advertising and marketing firm based in Tampa, Florida, for over ten years. She and her French husband (who worked for a luxury boat company in Sarasota) lived in Florida until July 2019. They returned to Europe in July of that year, he to work remotely in the UK for a start-up in France, she to carry on working for her Tampa company. They also had one-year old twins in tow! After three years living in the UK the family moved to Aix-en-Provence in August this year. My daughter continues to work for the same US company, managing a team of eight people, some of whom she has interviewed and hired online (she has also had to fire online in the past). Five work in the Tampa head office; one works from home in Oregon (having been recruited when living in New York), another is in Detroit and a third is in North Carolina. Now living in France, she is six hours ahead of Florida and seven hours ahead of her biggest client in Chicago. She works Tampa hours, requiring her to work close to midnight.


She does not need to say that keeping to these working hours is one of the toughest aspects of being a remote manager, especially with young children to look after. Many of the problems she describes are familiar to anyone who relies on online group calls to do much of their work, however good the technology – reading between the lines of what people are saying, picking up the subtle signals transmitted by body and voice, hearing the asides.


There are four things which she insists are absolute ‘musts’ for anyone contemplating managing remotely. First, she could not have done her job successfully if she had not herself worked in the Florida head office for several years and sat alongside at least some of her team and her own boss. Above all, she had learned and absorbed the company’s fairly eccentric culture by being physically there in Tampa.


Secondly, any new employees of hers must start out working in the office. How else can they learn the ropes and discover how they are expected to behave? She described how vital it was that a person she had hired just before the pandemic had started off being in the office. Without that traditional ‘on-boarding’ period the new hire would not have successfully survived being required to remote working during the pandemic.


Thirdly, she insists on speaking to every member of her team every day, sometimes as a group, sometimes singly.


Finally, and most importantly, she has to trust those who report to her to get on with their jobs without her micromanaging them. She must give them autonomy. This may seem at odds with her third ‘must’. But she does not expect a report each day from each member of her team. Those calls are often no more than a “How are you?”.


Last week there was only one subject for discussion between her and her staff: Hurricane Ian and the likelihood of it flattening and flooding the Tampa office and their homes. That was one of the hardest things that my daughter has had to cope with as a remote manager: not being physically present when her staff and colleagues were, potentially, in real danger.


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