Managing Remote Employees: Best Practices from Doist’s Head of Marketing

Hint: If you’re asking how to monitor your remote employees, you’re starting with the wrong question.

How to manage your remote employees
Illustration by Margarida Mouta

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“But how do you know people are actually working?”

This is a question you get a lot when you’re a team lead at a remote company. Implied in the question is the assumption that if you can see people are physically in the office, then they’re working.

Butt in chair = work.

But of course, people do all sorts of things in the office that have nothing to do with work — checking Twitter, attending unproductive meetings, getting sucked into email when they should be working on an important report. In fact, research shows that salaried employees do just 3 hours of real work a day.

Remote-friendly companies — for all their forward-thinking, innovative techy-ness — cling to their own versions of “butt in chair = work”. Messaging tools have green online indicators to show that you’re “at work”. Immediately responding to messages shows that you’re “working”. Some companies even require their employees to install tracking software on their computers to keep tabs on what they’re doing.

The expectation that remote workers be constantly available during work hours negates one of the greatest benefits of remote work: The ability to disconnect to focus on actually getting things done and responding when you’re ready to reconnect (aka async communication).

Managing a remote team effectively is not about monitoring the amount of time your team members spend online (in fact, that’s a great way to kill employee autonomy and motivation). It’s about building and supporting a team that doesn’t need to be micromanaged in the first place.

For the last six years, as Doist’s Head of Marketing, I’ve worked to strike a healthy balance between being a hands-on/hands-off manager of a fully remote team. Like other managers at Doist, I usually only see my team members in real life once a year at our company retreat which means that I have to rely on a unique set of tools to ensure that my team members are aligned with and working toward our company vision while also taking time to disconnect and recharge at the end of the day.

It starts with hiring the right people in the first place.

Hiring for remote greatness

Growing in popularity as it may be, remote work still isn’t mainstream. For every legit job offer that you publish, prospects will find another five sketchy-as-hell postings that promise “work from home and earn real money, fast!” On the flip side, for every genuine candidate that applies to your posting, you’ll probably sift through another handful of applicants who aren’t cut out for remote work (usually the ones who mention in the first line of their cover letter that they’re “interested in remote work” and clearly know nothing about your specific company).

These should all be red flags when interviewing remote candidates.

These should all be red flags when interviewing remote candidates.
These are the qualities we’ve learned to look for when hiring a remote candidate:

They show unapologetic enthusiasm for hobbies and/or have active side projects.

“For development and design roles, there’s a clear correlation between having side projects and being a great performer,” says Gonçalo, Doist’s CTO. To name a few, Scott from our Windows team is a landscape, wedding and editorial photographer; Galina from our Support team is a rock climber; and João, the head of Twist, founded the annual Make or Break hackathon in Porto, Portugal.

We look for people who are actively involved in hobbies and side projects.

Hobbies and side projects demonstrate a thirst for learning and an inherent drive to excel — traits that are important for any job, but are absolutely vital in a remote setting.

One of my favorite ways to gauge this type of enthusiasm is to ask a seemingly simple question at the end of every interview: “What are some of your favorite apps on your phone?” The “right” answer would include a solid dose of enthusiasm and thoughtful consideration. Something like, “I’m a really voracious reader so I enjoy using Audible and Kindle for iOS. I also have a reading project in my Todoist app where I save links to new books and there’s this really cool app called Blinkist that… etc.” As opposed to an answer like, “Well, Instagram is pretty fun. I listen to music on Spotify, and I use Uber sometimes… etc.” (Like my colleague, Becky says, “You cannot fake true geekiness 🤓.”)

They have experience working independently.

The learning curve for a new job — both technical and emotional — can be amplified in a remote setting which is why prior experience is a plus. But because remote work is still somewhat uncommon, it can be difficult to find people who’ve already worked successfully on a remote team.

A way around this limitation is to keep an eye out for people who have experience in other situations that depend on deep personal accountability, like someone who has started their own company, lead projects from start to finish, has been a successful freelancer, or has a side project they work on during their free time.

They go noticeably above and beyond when completing their test project.

At Doist, our hiring process always includes a test project. Aside from assessing technical prowess, a test project offers a glimpse into how candidates think through and solve problems as well as their willingness to go the extra mile. For example, when Fadeke, our social media manager, was tasked with creating a hypothetical one-week social media calendar for Doist’s accounts. She ended up handing over a stunning 76-page trove of ideas and content. I hired her on the spot.

When filtering for the right candidate, it’s also important to not:

🙅‍ Hire faster than what your team culture can sustain.

As a remote company, your culture is like water to a fish– you cannot survive without it. After Doist increased in size by 46% in just 12 months, we decided to voluntarily institute a temporary hiring freeze. “We built Doist on the idea of sustainable growth and since we’ve hired a lot of people recently, we’ll do a temporary hiring freeze in order to integrate them and adequately adjust our processes,” wrote Doist’s founder & CEO, Amir, on January 29th.

🙅‍ Forget that “passion for remote work” can actually be a red flag.

“It may seem completely unintuitive, but, in our experience, candidates who are explicitly ‘looking for a remote position’ or ‘like to travel’ are red flags,” says Jan, Doist’s Head of Windows. The motivation to apply for a job should come from a deep connection with the company’s values and an enthusiasm for the challenges of the work, rather than with their remote-friendliness. “Believing in the product and sharing a vision with the company makes for a happy workday… and less need for management,” adds Rastislav, Doist’s Head of Android.

With these hiring practices for remote teams in place, you’ll be a major step ahead when setting out to lead the passionate, motivated group of individuals that you’ve assembled.

Establishing healthy foundations from day one

Once you’ve found the right person to hire, it’s time to establish clear, healthy foundations for their professional and personal success on your team and inside the company.

As a huge fan of the concept of radical candor, I find that the most important foundation for your remote team is building trust on a personal level.

“Most people, since they got their first job, have been told to be “professional.” Too often, that’s code for leaving your humanity at home. But to build strong relationships, you have to Care Personally. You have to bring your whole self to work.”

— Kim Scott, author of Radical Candor

For example, it’s extremely important for me to know how Neil’s baby is doing so that I can lend him extra support or flexibility if and when he needs it. I love seeing the world through Hugo’s camera and living vicariously through Lucile’s adventures in New Zealand. When you make the effort to keep abreast with your team’s personal lives, it opens the door to a deeper bond beyond just “the office”. In turn, these personal connections help you cultivate a more candid relationship and a stronger sense of team.

Setting your remote team up for success also means establishing some basic, yet core professional foundations. As a manager of a remote team, it’s helpful to proactively learn:

  • How (and how often) each team member likes to communicate. Because we work asynchronously at Doist, I never expect an immediate response from any of my team members. That said, it’s helpful to be aware of people’s communication cadences so that you can tailor your management style to each person’s preferences. Being hands-off with one person might not work as well with another. “Don’t make assumptions about the desired amount of personal contact based on your personality. Some people need more, some less. Be sure to ask your team members about this early on,” says Jan.
  • Your team members’ different work styles. Anyone who works remotely should spend some intentional time thinking about how to set up their workday habits to fit their personality and needs. This shows a level of self-awareness that is really needed when you’re working on your own. Encourage your team members to experiment with their remote work setup and share their thoughts with you. That way you, as their manager, know they’re being intentional in how they work and how to best support them in the work environment/schedule that they prefer.
  • The difference between delegating tasks and relinquishing responsibilities. For anyone who’s been on the ground level of a new enterprise, a growing team means that it’s time to start “giving away your legos” so that the company can build an even more awesome tower. At a certain point after a new employee joins your team, they need to have their own responsibilities and be an impactful part of projects. As a manager, taking the leap of faith to not just delegate, but truly relinquish responsibility empowers your team members to rise to the occasion and affords them the space to grow creatively and independently (and even fail — which is often when we learn the most).

As a manager, you can’t assume that everyone on your team communicates the same way or has the same workflow.

Of course, this kind of communication isn’t a one-and-done thing. As Doist’s founder and CEO Amir wrote: “when you don’t see your coworkers in person every day, it’s easy to assume that everything is ok when it’s not.” It’s your job as manager to establish trust and regular communication to catch problems early.

The most important tool in your arsenal as a remote manager will be regular 1:1, real-time meetings. Prioritize them. Use them to catch up personally, discuss work-related triumphs and challenges, ensure that people are clear on priorities and feel secure in their place on the team, and generally keep a finger on the pulse of how your team is functioning. For more information and advice, Know Your Company put out an incredibly comprehensive guides to better 1:1s for both managers and employees. It’s worth a read for remote team managers especially.

Post-onboarding: Leading people who lead themselves

At Doist, our default settings are trust and transparency which means that we’ve had to think deeply about building an internal infrastructure that fosters autonomy and accountability while weaving webs of support throughout the various teams.

Make clear that trust is assumed, not earned.

On any team, it can be hard for new employees to know their place in the company. Without the daily feedback of face-to-face interactions, it can be even harder. There’s often anxiety about doing things the “right” way, particularly when there’s no one watching to make sure. The freedom and autonomy of remote work can be hard to get used to. In the first weeks and months, it’s your job as manager to help your new teammates feel comfortable making decisions and taking action independently.

“In the beginning, it can be daunting for newcomers to not have strict guidelines for how to segment their time and tasks. It’s critical to provide positive reinforcement, especially as a “manager”, so folks can be confidently autonomous and creative in how they allocate their tasks. That level of support clearly demonstrates that trust is assumed and does not need to be earned,” says Malin, Doist’s Head of Support.

Take yourself out of the equation wherever possible.

As a manager, it’s often your job to take yourself out of the equation to make collaboration and troubleshooting as efficient as possible. This is even more important on a remote team where responses often happen more slowly.

Open up direct lines of communication by putting your team members in positions to collaborate directly with other teams early on. At Doist, we work hard to hire Jacks and Jills of All Trades (more on that in this article) which means that people often tend to collaborate outside the circle of their team. For example, even though she’s not a developer or a designer, Malin is currently leading a comprehensive Email Refresh project; Evert from Support works on translating our apps into Dutch and works with both the product and content teams to write Help Center articles; and Lucile from Growth is overseeing the rehaul of our company-wide project management system. A robust network of support among team members — and among different teams inside the company as a whole—keeps the organization flat and helps team members feel comfortable reaching out to anyone on the team directly.

Taking yourself out of the equation extends to interpersonal issues too. When a teammate comes to you with a problem involving another team member, encourage them to reach out and address it directly. Instead of taking care of the problem yourself, coach them in how to approach those kinds of tricky situations themselves. Having radically candid conversations shouldn’t just fall on the manager’s shoulders — it should be everyone’s responsibility. When you develop a culture where a manager isn’t a crutch to fix everyone’s problems, you plant the seeds of leadership and transparency needed to thrive in a remote environment.

Empower everyone to have candid conversations with their teammates.

Empower everyone to be leaders.

One of the keys to our team’s success is that people don’t have to be managers to be leaders. There are small steps that managers at Doist take to develop leadership inside their teams. This is usually a process of incrementally increasing autonomy and responsibility, then sharing more managerial responsibilities like code reviews, editing, and more comprehensive project management. And of course, having radically candid conversations when they sense that another team member’s performance could be improved.

Of course, no matter how well you lay the foundations of trust and autonomy on your team, you’ll inevitably run into issues…

Red flags — when you sense someone might not be pulling their weight

Just because you trust your team by default doesn’t mean you turn a blind eye to performance issues. The thing most people don’t realize is that — even in a remote environment — it’s going to be obvious when someone isn’t pulling their weight. You don’t need online presence indicators in your messaging tool or invasive tracking software. Remember, it doesn’t matter how much time they spend in front of their computers, it matters what they actually accomplish.

Be results-oriented, not “time at work” oriented.

The most obvious performance-related red flags to look out for in a remote setting are repeated absences, consistent internet outages (the remote work equivalent of “my dog ate my homework”), or similar eyebrow-raising excuses. When these become a pattern, it’s clear that something is going on and needs to be addressed. Besides simply not “showing up” to work, a few more red flags to look out for when managing a remote team include:

  • The simple math: “There are some ‘easy’ metrics that allow me to check if team members are working: amount of tickets solved, quality of ticket responses, Twist threads created, participation in discussions, etc.” says Malin. If each supporter responds to 100 tickets a day and one of their teammates is consistently responding to only 10, there’s a problem. “But it’s not feasible for a manager to spend 50% of their time checking up on other people’s work. This is a waste of time. The best way to avoid this is regular communication and trust,” she adds.
  • Continuously recycled work: For example, if a social media manager posts the exact same messages time and time again without endeavoring to create any new types of content.
  • Obvious lack of follow through: In our team communication app, Twist, you can “emoji react” to other people’s comments or messages. While this can be useful to help show you read a specific comment, when a person emoji reacts to a comment that obviously requires that they take action — and they don’t take any action — an issue could very well be brewing.
  • Lack of communication: A team-wide expectation of responding within 24 hours ensures that everyone can maintain their own work schedule in whatever time zone they’re located in. If a team member regularly takes more than 24 hours to respond to messages — particularly time-sensitive ones — there’s an issue.
  • Lack of improvement: If a team member’s performance hasn’t changed at all based on feedback, there’s a bigger issue. “When feedback during 1:1s has no effect on performance, I know that it’s time to double down on communication with this person so that we can try and turn the ship around,” says Allan, Doist’s COO.

As a manager on a remote team, it’s not a matter of if you run into these problems but when, so you need to be prepared to address them quickly when they can still be solved.

Turning the ship around

Broaching the subject of poor performance with a teammate is uncomfortable no matter how many years of experience you have as a manager. But when you approach the subject with a radically candid foundation and an empathetic mindset, everyone can come out of the situation stronger for it.

Remember, it’s a problem to be solved, not a punishment or an ultimatum. Dedicate one-on-one time — in real-time — with this person to figure out the root of the problem and co-create a step-by-step action plan that reflects this person’s specific situation.

Prioritize an empathetic solution over an easy one.

For example, if I learn that a teammate’s performance is suffering because of an illness in their family, I won’t suggest that they simply stop working from home and get a coworking space to rid themselves of the distraction. Rather, I’d offer a handful of paid days off to clear their mind, dedicate time to care for the sick family member, and contemplate a more sustainable way forward. In the long term, an empathetic solution will produce better results than pushing people to work harder in the short-term.

Communicate quickly, clearly, and concretely.

If there are specific issues related to the way someone is doing their work — aside from extenuating circumstances like an ill family member — it’s crucial to clearly communicate that there’s a performance issue that needs solving.

Being fully committed to your team’s success requires that you put a lot of time and thought into compiling concrete, specific examples when you approach someone about their performance. It helps to write all of your feedback in one central place — you’ll always be clearer and more thoughtful in writing. The more matter-of-fact and solution-oriented you are in your feedback, the less sting it has so be clear and direct.

Share the document with your colleague ahead of your next 1:1 meeting — but not too much ahead of time that they worry themselves to death over it — so that they have a chance to process it and come to your 1:1 with comments, questions, and possible solutions in hand. In your 1:1, discuss the feedback and come up with a plan of action together. Neither party should feel like they have to have all the answers right away.

“Honestly, it’s like any relationship — you should come out the other side of a hard situation you had to work through together stronger and with more mutual trust and respect,” says Becky, from Doist’s marketing team.

Address performance issues directly, empathetically, and collaboratively.

Then, continue to communicate consistently.

As you climb back up the mountain with this team member, it’s worth taking extra time to ensure that performance expectations are clear and that this person has the resources they need to get back on track. Like a coach training a runner for a marathon, you need to set a solid, healthy foundation from which your teammate is able to progress toward their goal.

At all times, it’s important to be intentional and consistent about your feedback and communication with your team members. Give positive feedback immediately and only when you really mean it. Give negative feedback immediately and only when you really mean it. Always waiting to share feedback until a 1:1 only sows additional and unnecessary anxiety.

Get more advice on leading remote team members. Our guide, Leading Distributed: The Remote Guide to Management, is packed with effective management strategies from leaders at distributed companies like Stripe, Remote, Buffer, and more. It covers topics like avoiding micromanagement, making time for high-level thinking, tracking performance, and so much more.

There’s no question that managing a remote team comes with unique challenges. But instead of throwing up our hands and saying remote teamwork doesn’t work or resorting to self-defeating tactics like expecting immediate responses during “work hours”, we need to come up with better — more empathetic, more empowering, and more direct — ways to lead.

I’m still learning myself — and will probably never get it right 100% of the time — but I hope this article is a helpful start for remote team leaders who are challenging the way things have always been done and are defining the management best practices of the future.

Twist is a communication app built by a remote team for remote (and remote-ish) teams. Try it for free