Jory MacKay
Jory is a writer, content strategist and award-winning editor of the Unsplash Book. He contributes to Inc., Fast Company, Quartz, and more.
October 15, 2020 · 14 min read

Managing Remote Teams: How the World’s Top Startups Keep Remote Teams Connected and Creative

🎁 Bonus Material: Free Remote Work eBook Guide!

Managing Remote Teams

Managing remote teams can feel a lot like playing chess... with a blindfold on. You can use all your experience and instincts to make the right moves and still have no idea if it made any impact (or even what your team is up to!)

Awareness and human connection are the manager’s best tools. But they’re also the first things to get murky when your team goes remote.

The less face-to-face time, the more issues seem to creep up. Comments and feedback get misconstrued. Expectations aren’t properly communicated. And your remote team suddenly feels unseen, unheard, and, often, unhappy.

Now, that’s the bad news. The good news is that remote work is nothing new. Plenty of people before you have spent years learning how to manage remote teams–and have it down to a science.

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At Planio, we’ve spent the last decade empowering thousands of teams to communicate and collaborate properly. But to learn what it takes to really manage and lead a remote team, we spoke to remote managers at some of the world’s top companies, including Buffer, Zapier, Remote Year, Close, and Dribbble.

Here are the strategies, techniques, and tools these teams use on a daily basis to manage their remote teams.

At Planio, we’ve helped thousands of companies communicate and collaborate while working remotely.

The 3 biggest work challenges every remote manager faces

Let’s start with some good news. Dive into the research, and you’ll quickly see that there are lots of reasons for managers to get excited about remote work.

Here are just a few remote work stats:

However, getting these sorts of benefits out of your remote team takes work.

More specifically, it requires overcoming the most common remote work challenges teams face. Leadership means seeing and addressing issues before they come up. So what challenges should you expect your remote team to go through and how can you solve them?

1. Remote work requires more willpower, higher prioritization skills, and better time management

First off, remote working requires a different skill set than working in an office.

Flexibility and autonomy are two of the top reasons why people love working remotely. But they can also be two of the biggest challenges.

When your team is working from home, they’re more responsible for how they spend their time and energy. This means you need to follow a productive schedule, build good habits, and not get distracted–all things that few of us are taught to do.

As Zapier’s data team manager, Muness Castle, explains, people new to remote work can have problems adapting to the lack of a regular cadence, structure, and the connection with fellow teammates:

"I've worked ~15 years on co-located teams and the last ~5 on remote teams. For teams without clear goals or decision-making process and lower autonomy, co-located teams work better. On the other hand, when those issues are addressed a remote team can be as productive and sometimes more so than a co-located team."

2. Remote teams often feel isolated and disconnected from the company culture

Next, many remote workers miss the regular human connection of being in an office–especially now with social distancing measures in place. Flexibility and autonomy are great if you’re ok with being alone and painful if you’re not.

Not only is isolation hard on your team’s well-being, but managing remote teams requires rethinking how you create connection and company culture. But that’s not always a bad thing.

As Greg Caplan, CEO of Remote Year, explains, a recent Gallup poll showed that remote workers actually score higher in areas like "my opinions seem to count" and “understanding the company’s mission and purpose,” which are signs they feel more part of a company’s culture.

"We cannot assume that culture will just happen as a result of employees being together in a physical space.”

It’s up to remote managers to explicitly communicate and state their values early on and make sure their teammates are on board.

Remote workers score higher in areas like “my opinions seem to count” and “understanding the company’s mission and purpose”.

3. Remote teams can easily drown in communication tools

Lastly, while there are more remote tools than ever, using them correctly and not letting them take over your team’s day can be a huge challenge.

As a remote manager, you’ll want to know what’s going on with your team. But too much communication quickly kills productivity.

Communication tools can quickly cannibalize your productive time, with the average worker checking email or chat every 6 minutes of the day. And when you’re working remotely, it can feel like you’re never allowed to be offline.

People who work remotely sometimes feel the need to “perform” more at work. This translates into what’s known as work from home guilt (WFHG), where you end up spending all day answering emails and chats just to be seen.

7 strategies and techniques for managing remote teams used by top remote companies

Those three remote work challenges are at the core of successfully managing a remote team. To sum it up, you need to think about:

That probably sounds like a lot. But that’s because managing a remote team is a lot of work.

You can’t just take all the processes and workflows you used in the past and try to translate them into this new working environment.

So how do the top remote companies manage their teams?

It all comes down to these 7 powerful remote management strategies.

1. Update your communication processes to understand when your remote workers need help

When you’re working in an office, it’s easy to see when someone’s having an off day or when something is bothering them. Maybe it’s personal issues, or they’re feeling under the weather.

But when you’re managing a remote team, it’s almost impossible to pick up on those cues.

(And not too many people are likely to message their manager to tell them they’re going through a rough patch and might not be doing their best work.)

As former Upwork CEO Stephane Kasriel explains:

“It’s easy to overlook how essential the skill of remote management is because, for many, the classic picture of a ‘manager’ still means someone sitting at a desk in an office surrounded by (or overlooking) their team.”

The first thing you need to do, according to Dribbble’s former VP of Product Sarah Kuenhle, is to make an effort to really get to know your team:

"Managers need to pay much more attention when managing remotely. I want to learn what makes my team tick. What they're interested in. What's going on in their lives. That way, I can be the best support I can."

To dig into your remote team’s needs, Zapier’s Muness Castle suggests dedicating regular time to discuss exactly what everyone needs to be doing. On his remote team, they do this by asking a few simple questions each day:

"We write these down periodically and make sure to be explicit about the reasons we change our plans. It’s not that the plans are set in stone, rather what matters is that we understand each other’s priorities and concerns."

Regular check-ins like this are key to managing remote teams. You need to have a process and routine in place to quickly highlight issues before they get any worse.

2. Use “office hours” to save your remote team from nonstop meetings, calls, and emails

Communication is the key to successfully managing a remote team. But as we said earlier, one of the biggest remote work challenges is knowing when to reach out to your team and when to let them work.

One of the amazing parts about working remotely is giving your team the ability to work when they’re most productive. But too many managers eat up those peak productive hours with meetings, calls, or constant check-ins.

Instead, the best remote teams work in bursts–moments of dedicated collaboration followed by long stretches of focused work. This is similar to the idea of “office hours” that university professors use.

Your team can have specific office hours (as in, I’m online and available from 1–5 pm each day but mornings are for focus). Or, you can create a more ad-hoc system based on awareness and respect.

As Planio CEO Jan Schulz-Hofen explains, they use Planio Team Chat to show their status and when they’re available:

“Our etiquette is: When someone is logged on to chat, it's okay to ping them by mentioning their name to start a conversation. Whenever we need time to do concentrated work, it's totally okay for everyone to be offline in chat and to have our phones in silent mode as well."

The best remote teams work in bursts – moments of dedicated collaboration followed by long stretches of focused work.

This might seem like a huge departure from the ‘always-on’ communication style you’re used to. But dedicated focus time is one of the main benefits of working remotely. Kuehnle agrees. Adding that a lack of distractions helps remote teams thrive:

"There is a feeling that you must be present in order as proof of productivity. In reality, the opposite is usually true. Having the freedom to block out distraction, in a place that's most comfortable for the individual, and have focused time for work, leads to greater productivity."

3. Be intentional about creating a company culture

Culture is the glue that keeps your team together. But it’s one of the hardest things to build when working remotely.

Remote culture requires creating connections within your team as well as to the company’s larger purpose. That’s where clear goal-setting comes into play. Well-written OKRs (objectives and key results) give your team regular insight into how their tasks are contributing to the company’s larger goals.

But culture isn’t just about company vision and goals.

Create a Company Culture

For Planio CEO Jan Schulz-Hofen, it’s the small things that help you create company culture, like showing your team that it’s OK to not be on your A-game every single day:

"At Planio, I tell my team if I'm having a bad day or if I'm not in the mood for work on a certain day and they do the same. It's only human after all. We're not machines. When you know your teammates will respect how you’re feeling it's much easier to be honest about these situations."

Remote culture can also come from unexpected places, like connecting to your team on a personal level. At SaaS startup, Close.com, CEO Steli Efti experiments with non-business tools to make the conversation feel more personal:

"The greatest challenge growing a remote team is cultivating a vibrant and intimate company culture. The remote tool stack is awesome in creating consistent team communication but poor in fostering personal social connections with your co-workers."

“That's why we experimented using a tool like Snapchat (not really a business productivity tool in the conventional sense) as an internal (and fun) way to help co-workers share special moments during their workday with the rest of the team and it made a huge positive difference."

4. Build team connection by letting the personal come into the professional

Tools and processes can help your team work effectively together. But for remote teams to really thrive, they need the same sense of connection and camaraderie that in-person teams do.

Unfortunately, it’s not always easy to force your team into connecting.

That’s why remote managers need to lead by example. Create safe spaces for people to bring their full selves to work and then be active and supportive in them. At Remote Year, they call these "virtual water coolers":

"For example, we have a ‘books and music’ Slack channel to allow team members to share what they’re reading and listening to.”

At Planio, creating this type of virtual watercooler actually spawned one of their most popular product features. When both their main frontend engineer and their software architect went remote, their team suddenly became much more distributed than they had been in the past:

"Obviously, we wanted to make it work, so we sat down and thought about how Planio needs to be improved to be better suited for remote work. One big result of that is the launch of Planio Team Chat as a core feature to extend our suite of tools.”

“Fast forward to today and we have project-specific channels and a ‘watercooler’ channel where we discuss movies we watch, things that happen in our personal lives, etc. There are also tons of cat and sloth pics."

For Kuehnle, that connection comes less from a dedicated communication channel and more from a shift in mindset. That’s why she suggests hosting weekly ‘anything goes’ meetings:

"Sometimes we talk about design. Other times we’ll talk about muppets or Disney. It’s a free-form meeting where we can share work, give feedback, and just spend time together. We laugh a lot and it’s a very welcoming, safe place for the team to open up."

5. Defer to asynchronous communication (but change how you use it, especially for feedback)

Asynchronous communication–like email–is one of the best tools for remote teams as it lets you stay connected while letting people answer when it suits them best. However, it can be a nightmare for giving and receiving feedback, especially when you’re working remotely and can’t easily follow up.

When you’re managing remote teams, you need to understand how people prefer to communicate and what communication style they use.

According to Buffer’s Director of Marketing, Kevan Lee, this all comes down to understanding how your team works, and tailoring your approach to feedback accordingly:

"I need to be mindful of how a person prefers to receive feedback: do they like the real-time nature of a video call, or would they prefer an email so they can sit and reflect on the feedback before responding?"

Planio’s Jan says that giving and receiving feedback is a skill that needs developing whether you’re working remotely or on-site. Yet it’s especially important for remote managers to create an environment of trust where teammates know feedback is factual, not personal:

"Once that is established–when giving feedback–we don't need the sandwich approach (where we say something nice first, then give feedback and then say something nice again). Instead, we can feel comfortable addressing issues directly. When receiving feedback, it's equally important to listen on a factual level. Don't take it personally, because it's not meant to be."

With those factors established, Jan says they use Planio to provide feedback in writing, which lets the person giving feedback take the time to write down their thoughts clearly, and also gives the receiving person time to reflect and re/act accordingly.

This also means all your reviews are on record (and searchable as Planio issues), so the learnings are shared collectively as a team.

6. Focus on results (and use data to help you)

Managing remote teams is especially difficult because it’s often the quietest contributors who are doing the most work. But when all you’re seeing is an empty chat log or someone’s status as “offline” what are you supposed to think?

Giving praise to the people who are online all the time or quickly answering questions sends the wrong message about how you want your remote team to work.

Instead, managing remote teams means focusing on results over hours worked.

However, this is easier said than done.

One-on-ones are a great place to talk through issues and highlight progress. But you don’t want to always have to reach out and disrupt someone’s flow to find out what they’re working on.

That’s where a project management tool like Planio becomes so important.

Agile Board with Assignee set to Developers

Use the Agile Board to get an overarching view of your projects and then filter by assignee or team to quickly see what each person on your remote team is working on, the status of any issue or project, and even the time they’ve spent on each task.

This lets you check in on progress and identify bottlenecks even before you reach out to your team.

7. Be flexible and give your team true autonomy

Most remote managers can’t stomach the thought of their team starting work at 11 am (or later!)

However, true autonomy–not just saying your remote team has flexibility and control over their schedule–has huge benefits. One of the biggest is their ability to be creative and innovative.

Freedom Improves Creativity

For Remote Year’s Caplan, taking advantage of the flexibility and freedom of your remote team is one of the best ways to promote creative thinking:

"For certain types of creative work, you have to be in your favorite room, or listening to your favorite music, or sitting in your favorite chair to do your best thinking. No other environment will do. That’s why people often say that they do their best thinking in the shower or that their best ideas pop into their brains when they’re not thinking about a subject."

Caplan says they encourage and even offer a small stipend, so that team members can work from wherever will make them most efficient and happy, which rarely means people are working from an office.

"We have found that giving employees the ability to control their own work environment and location increases their happiness, their productivity, and their creativity."

As Steve Jobs famously put it, creativity is just connecting things. Unfortunately, it’s so much easier to connect things when we’re together and hashing it out. As Buffer’s Kevan Lee discovered, it can be harder for remote teams to bounce creative ideas off each other.

However, this just means you have to be more purposeful in manufacturing those experiences:

"We'll get together after each six-week work cycle to discuss what went well, what we'd like to change, and what ideas we have for the next cycle."

When you’re managing a remote team, you need to create a cadence of time to reflect and time to get creative. Too much or too little of either and your team will lose their flow.

Giving employees the ability to control their own work environment and location increases their happiness, productivity and creativity.

This also requires having the right remote tools and resources at your disposal. According to Planio CEO Jan, you need to make sure your team has access to everything they need to be creative, even when you’re not around:

"Instead of managing in a ‘push’ manner by giving people tasks and next steps, I always try to establish a ‘pull’ style where everyone tries to get the resources/information needed for their next step so they can continue their work and aren't blocked. ‘Pull’ also includes (virtually) raising a hand when you're stuck with something and finding the right person to help you with moving forward."

The essential remote tools to manage (and support) a remote team

A big part of managing remote teams is making sure they have the tools they need to do their jobs.

The only reason we’re able to work remotely as well as we do now is due to the huge increase in remote-specific tools we now have access to. As Kuenhle explains:

"With so many tools that enable people to work together today, there's no reason that remote teams can't be as effective as those in the same room.”

But with all those new remote tools has come a ton of confusion.

What tools do you need? And which ones are just extra noise?

Where does communication happen during the workday?

How do you collaborate on files (and know you’re working on the right version?)

What about showing appreciation for people or making company-wide announcements?

Choosing the right remote tools will make managing remote teams easier. So which tools are the top teams using?

Kevan Lee, Marketing Director at Buffer

"We use Zoom for video calls, Slack for real-time communication, and Discourse for team announcements. For collaboration, we like Dropbox Paper for collaborative docs, Gmail for transparent email, and Trello for project management. Finally, we use HeyTaco (a Slack app) for recognition and celebration."

Muness Castle, Data Team Manager at Zapier

"I believe it's important to have clear, low friction communication tools. I like a group chat tool or IRC and then something to elevate to when you need higher bandwidth communication, usually video chat.

“Other tools I find invaluable are real-time collaboration tools. Word and/or Google Docs are essential for taking notes during a meeting. While whiteboards like those in Skype for Business are great for high-level planning calls."

Sarah Kuehnle, former Head of Product at Dribbble

"Slack is critical for day to day discussion about projects, but also as a way for our team to connect socially. We have a mix of company, product-focused, and social channels where we can gather. We use Zoom for video conferencing because it's very reliable.”

“Finally, a good project management tool is important for keeping everyone on the same page and ensuring everyone knows who's doing what."

Greg Caplan, CEO at Remote Year

"Tools like Zoom, Google’s G Suite, Slack, and Whatsapp help us collaborate and communicate every day. I also send a weekly email to all team members to update them on milestones and important information for the week prior and the one ahead."

Jan Schulz-Hofen, CEO at Planio

"We built Planio to be a comprehensive project management tool and collaboration platform where everything is in one place.”

“We advocate against having too many tools because you'll never find files or past communications again if you have to search for them in 5 different tools. It's also much harder to control who should be able to see/edit/comment. Plus, you have almost no ownership of your data with everything scattered across X different cloud providers.”

You’ll never find files or past communications again if you have to search for them in 5 different apps.

Here’s how Planio provides everything your remote team needs:

As Jan explains, “The beauty of Planio is that everything is in one place with a unified user interface and centralized control."

Final words of advice on managing remote teams and making them successful

Building a remote team can be the smartest thing you do for your company.

It can save costs, open you up to the best talent, and allow you to build the kind of culture you’ve always wanted. But there are also special considerations that need to be taken to ensure that everyone’s doing their best work and stays happy.

It takes time to experiment. And not everything will work. But listening to the words of leaders at some of the world’s most forward-thinking and progressive remote companies will give you a good idea of what it takes to build a successful team, no matter where you are.