How to Manage the Distinct Personalities of your Remote Team

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By Shyla Foster

So you think it’s time for your company to take the plunge and go remote. While you and your team begin to hammer out the details, new concerns bubble up—what if your staff burn out or fall through the cracks? Managing a team with such diverse personalities is tricky enough when you’re under one roof—you can only imagine how it’s going to be once everyone disperses.

Of course, some personalities are better suited for remote work than others. Some members of your remote team will punch the air and run home when you announce that you’re going remote. Others might glance hopelessly around at their office friends, at their favorite desk, at the cozy couch, and not know how to deal.

You can’t 100% predict who will love working remotely and who’ll flounder, but if you’re prepared, you can meet each member of your team halfway to set them up for success.

Here’s a breakdown of the different characters you might have on your team, and how to help them through the transition so they’ll thrive in your (newly) remote business.

1. The Show Host

The show host is the charming, larger-than-life extrovert who always makes a great impression on customers. You always want them on calls, because they can win over anyone they talk to.

You might be worried the show host can’t handle the isolation of working remotely. A lot of people assume that extroverts in general simply aren’t suited for remote teams—but a recent study shows that this is totally unfounded. In fact, under the right supervision, extroverts can really excel in a distributed team, so long as their social needs are still met.

Solution: Screen Time

The show host lives on face-to-face interaction, and they need to know you’ll prioritize that. Zapier uses a group video chat tool called Sqwiggle every day as a way to keep the remote team “together” and visible even though they’re distributed. Mike Knoop, the co-founder of Zapier, says “the main reason we use [Sqwiggle] is to have a constant presence with our team.

That consistent presence is exactly the environment the show host, who gets their momentum from interaction, needs to be at their best. In fact, they’ll take to this strategy immediately, since it’s in their nature to jump at the chance to socialize.

Being in touch constantly is a vital part of company culture: you want to replicate an office where everyone can interact, and not just about business. Tools like Sqwiggle let you do many of the things you’d do if you were in close proximity to one another: speak spontaneously, see each other’s faces and expressions, have a colleague working beside you. It also ensures that the show host’s best skills, talking and facilitating, are still contributing to your company’s culture.

2. The Escape Artist

The escape artist does great work, but they’re hard to pin down. They often have other concerns that require them to leave early or miss days.

Working remotely seems to spell certain disaster for the escape artist. They may not always be able to stick to a schedule, but at least there was one. They had useful parameters (work hours, meetings, processes), that helped them pick up where they left off. Without a workday routine, they may just fall off the radar completely and never get anything done.

Solution: Focus on Productivity

The main thing is to focus on what they produce, not when or how long they work on it. Keep track of their progress with a team task managing tool, like Asana.

Freelancer Dan Virgillito, a regular author for WP Curve, finds Asana invaluable for both freelance work and remote teams. Projects can be started and split up into tasks and subtasks, so that every detail of every goal can be assigned to different team members in a transparent way. I Done This is also an effective tool that facilitates remote standups, where you focus solely on work done, not how much time it took to complete.

It’s important to give your remote team hard deadlines and expect great work, but leave everything else (or as much as you can) up to them. Let your employees schedule, adapt, and experiment as needed. The end result might not be what you expected, but it could be even better.

3. The Newbie

Newbies are delightful. They dive in with both feet, and are full of questions. They’re eager to learn everything and turn to everyone for advice.

Onboarding a new team member is hard enough without everyone being spread out. Face-to-face training is impractical, but you want to establish a hands-on vibe for their onboarding process. It will be infinitely harder for the newbie to learn the ropes if they feel like they’re on their own.

Solution: Use Onboarding Tools Remotely

With the help of an in-depth onboarding tool, you can give new remote hires all of the information they need—from the usual hiring paperwork to small tasks and projects desired to show them how your team works.

The clothing startup ModCloth uses Lesson.ly to train their customer care hires. They designed courses and used Lesson.ly’s grading feature to “see who learned what, when they learned it, and how well, without having to tap anyone on the shoulder or send manual reminder emails.”

Newbies need to feel on-task and valued. Employee onboarding tools are the best way to streamline a comprehensive process for each remote hire that shows both of you what they’ve learned and what their strengths are.

4. The Old Boy

The old boy has been in “the business” the longest and is skeptical about change. They feel secure in their “if it ain’t broke, don’t fix it” mentality. New tools and business models make them antsy, but they jump on the bandwagon eventually.

They might be the last person to sign off on remote work because that’s just not “how it’s done.” Their transition will be difficult, and in the meantime you don’t want them to worry about where they stand in the company.

Solution: Time

The old boy is going to need time to adjust. Transition your team to the idea of working from anywhere before you make the switch.

There are lots of ways to experiment with this. Try switching from desktops to laptops in the office, and do away with assigned desks, to encourage mobility. Start having teams work from home or in the office on a rotating basis so they get used to relying on online tools to stay in the game.

TechnologyAdvice gave its employees the option to work from home multiple days a week to test out the viability and desirability of a remote team. Then they hired enough remote employees to double their workforce. TechnologyAdvice’s HR manager Heather Neisen cautions that “it does take two to three months for everybody to settle into it,” so thinking of the transition as a long game will definitely help get the old boys onboard.

5. The Zealot

The zealot is admirable, but a little unnerving. They’re the workaholic that never comes up for air. You get this sneaking suspicion that they don’t do anything at home besides work and eat, so they can keep working.

The concern here about remote work isn’t really for you—it’s for them. If they’re allowed to work from home, the zealot might shut themselves up in their house and neglect essential parts of life, like diet and exercise.

Solution: Encourage Work-life Balance

Reward the zealot for their excellent work in a way that encourages them to devote time to other interests, and maybe even leave their house.

Startups like Fitoracy and Yipit use Uncover, an app that allows you to send a wide variety of rewards to your employees, such as unlimited access to ebooks, gift cards, subscriptions, housecleaning services, and movie tickets. Vinicius Vicanti, cofounder of Yipit, uses Uncover to offer their whole team Spotify subscriptions, to great success:

People love Uncover…We like to provide perks that make people happier at their job. If they’re happier at their jobs that means they’re going to be more productive. Happier people at their jobs are more likely to recommend people to come join Yipit as well.

With these perks, the zealot could devote some time to learning a new skill, getting exercise, or nurturing some other hobby—or simply getting outside. It’s a great way to combat employee burnout, that comes from all work and no play.

Remote Teams Come Down To Trust

Whether you want to take the leap with your business and go remote, or you already have remote employees, it comes down to trusting your team. And that team may be made up of a medley of personalities, from the charismatic show hosts to the green newbies, but remember and trust that they believe in the product and one another.

It’s a matter of using the right tools that account for your remote team’s strengths and weaknesses—in other words, as their leader you need to meet them halfway, so you all can win. It doesn’t matter what personalities are on your team, or where in the world they are. If you trust them, and you’re meeting their needs, you’ll be just as efficient as if you were sitting across the room from one another.


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