Last week I published a beginner's guide to working while cruising, detailing how I structure my days as a remote business owner. One unsurprising piece of feedback I got was that many people have tried to hire remote workers or people who travel while working, and have found them to be less reliable than traditional workers.
If this rings true to you, I feel your pain.
I've run several remote businesses and between them I've culled through thousands of cold applications for remote positions. It took lots of trial and error to pick the right people to work in a distributed or remote environment. It also takes a lot of work to be a good manager to remote employees. With that said, here are my major guiding principles for building a remote team of people who travel.
Hire remotely (or in other time zones) only for jobs that can be done asynchronously.
The nitty gritty of this depends on your industry, but I've found in editorial that short turnaround work like breaking news, social media for breaking news and coordinating with teams that need to work together closely on tight deadlines (sales pitches) needed to stay on a US timezone to work well. However, remote workers can be a boon if you need to expand your workday reach. I've seen great success in hiring people from Europe to break stories earlier than East Coasters would be able to.
Build a job application that tests responsiveness as part of the interview process.
I've hired roughly 100 people in the last 5 years and for the last few positions the ratio was about 2000 applicants to every open position. Eek!
I had to remake how I hired and it's now super effective.
First, determine the four to five qualities you need in the position and then develop 2 levels of application questions.
The first level should be for ability to handle details and responsiveness -- my favorite tricks are to ask them to deliver their application back by a certain time, add a specific word in their cover letter and to have them send something in PDF format. That rules out about 80 percent of applicants and you can auto-search those responses in applications (Protip: in greenhouse.io you can bulk search applications.)
Essentially, you shouldn't have to look at your fist round applications to weed out the worst of the bunch. Use the second round app to ask questions and give challenges that illuminate their skill set.
Read those applications and take notes on where they're weak, then use your actual interview only to clarify what you've already learned and drill down on weaknesses. I find in those interviews that asking them questions about real experiences rather than hypothetical situations gives you a better idea of what kind of person they are. For example, "tell me about a time you made a mistake and how you fixed it" can really tell you a lot about a person.
This application process can work for any kind of employee, but it's especially important for remote workers, who need to be extra detail-oriented, resourceful and tech-savvy, as well as responsive.
In your interviews, ask for details of travel and routine.
People who are good at this aren't good by chance. They, like me, have really strong plans around getting internet, building structure into their days, and they think A LOT about how to do their jobs well. I think it's totally fair to ask that stuff as part of the interview process. I can talk all day about our wifi and cell boosting rigs! If they're new travelers, I'm more likely to pass on hiring because they haven't figured their you-know-what out yet.
Never hire someone for their first job as a remote worker.
They haven't been broken in yet into work norms in general. I totally believe in giving people first chances, but new workers need to be socialized before they're set free! (And sorry, someone else can do that.)
The more senior the position, the better a full-time traveler will work for you.
The longer someone has done this and the more they know about their area of expertise, the more likely they are to be able to handle both at the same time.
When you're working with new people, give them a really clear set of guidelines for cultural norms and behavior for remote work.
Go over a one-sheet on your employee's first day with a clear set of consequences for what happens if they break these norms. This sounds like kindergarten, but it actually is quite relieving to remote workers to have guidelines to follow and they usually follow them well. Remember that they're in their own kind of vacuum from your business, and following rules allows them to have a stronger sense of job security.
Never let people *start* traveling at the same time they start working for you.
I had a two-month ban on traveling for new workers at the last couple of roles I ran, and it worked really well for those people wanted to use their remote work to travel. This harkens back to the advice I gave on my last post, which is to give yourself time to figure out your travel and build a business. The people who work for you should do the same.
Traveling while working means slow travel.
Some may quibble with this, but in my experience, you need to build in lots of time for working and if you don't, you'll always run into problems. If people have ambitious travel plans while working, I get a little suspicious and ask for more details.
Let your like recognize like.
There's a certain vibe that really good remote-working travelers exude and I can smell it for miles (insert dirty backpacker joke here.) You probably know what I'm talking about, and don't ignore it!
It takes years and commitment to get a good groove and a lot of people, often really excellent workers in in-office environments, never get there. Remote business management and working isn't for everyone, but for the people it works for, you can expect more loyal employees, a stronger work ethic and often a discounted cost of work. Providing your employees and contractors freedom in exchange for them earning your trust is a foundation of building a great business, and remote working can truly accelerate that.