What is the hardest part about managing a remote workforce?

Acceleration Partners

Different laws in various states and keeping on top of that while trying to be fair to the masses. 2. Keeping everyone motivated and energized, especially during the stressful or busy weeks. 3. Making sure we are hiring resilient and very self-motivated, positive people.

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AgileBits

Balancing socialising in a virtual workspace with not working in a silo. When working remotely, it’s so easy to either block out everything and become isolated, or get so caught up in the various conversations taking place that it becomes a challenge to focus. This is especially true because online conversations are archived and readily available, unlike, say, missing the morning banter around the coffeemaker.

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AirTreks

Growing larger than 50 people seems hard. It’s hard because you need a layer of managers in there if everyone is going to get individual attention. It gets harder to keep core values and the individual attention you had before.

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American Express

We’ve had the most success with employees who came into the experience with a realistic understanding of the nature of the job and what it’s like to work remotely.

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Answer Connect

When you cease seeing a person all day, every day, you have to develop new ways to determine if they are present and working hard. You also need to learn how to connect, engage and build rapport when there isn’t a real water cooler to create chance encounters. These things are tough.

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AnswerFirst

Making sure they are happy employees. You can’t see them and must rely on virtual communication, which doesn’t always reveal an unhappy employee.

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Appen

Developing cultural sensitivity and acumen that allows one to manage their own style and preferences so they can connect with different people around the world.

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Appirio

The toughest part about managing a remote workforce is making sure everyone feels connected to the team and culture of Appirio. We work very hard to have local team events, virtual events, and constant video meetings; however, it can still be difficult to ensure everyone feels connected. Since you don’t see your team members in the office on a regular basis you may not always know what is going on in their day to day so it is crucial to find ways to stay in touch regularly.  

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Authentic Form & Function

The lack of body language and in-person cues can be tricky. But that being said, it can also be a double-edged sword. Having a “bad day” in person is very different from that same bad day over team chat and a video call. The most important thing to keep in mind as a manager is that we’re consistently checking in with, and taking the pulse of, how the team is feeling over any given week.

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Big Universe, Inc.

I’m not sure the challenges are that much different. For example, you can have productive and unproductive employees in both, remote and non-remote, environments. One hard part is the inability to have a quick gathering such as a lunch out, picnic, happy hours, etc. However, we try to simulate this by having a “Fun Friday” gathering over video at 4pm ET weekly, where people can drink whatever they like (alcohol, coffee, etc.) — it’s sort of our attempt at a “virtual happy hour”.

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Blossom

To me it was letting go of the idea that everybody is available at some specific time. I was always a fan of asynchronous communication, but sometimes you are blocked and need a team member to help you. With everybody in the same office working roughly the same hours, you walk over to their desk and ask them. Being remote and in different time zones with totally different schedules, you can get stuck. The solution (at least for me) is to have more than one thing on my plate so I’m able to switch over if I am blocked. I also make sure to think ahead and plan more time for things to be delivered.

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Bright!Tax

You don’t develop such close relationships as you do with people whom you see every day. This can be a positive too though, as productivity tends to remain high and also you might find that you didn’t get on with someone so well if you saw them every day!

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Canonical

Without the luxury of seeing colleagues each day, it can, at times, take longer to identify issues.  For this reason managers need to see engagement and communication as key priorities for their team.

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CloudPeeps

For me, it’s to do with setting the pace. When you’re in an office, the fastest person often sets the pace and lifts the energy and momentum of folks around them. I think it’s easy to ‘hustle’ when you’re out and about with your team and have an effect on each other. It’s harder to communicate the speed things need to happen at via Slack or email. You often need to show not tell. I’ve found setting hard deadlines helps us increase our speed and meet milestones faster.

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Coalition Technologies

Creating a healthy balance between trusting our team members to manage their work time and monitoring their activity. We have team members use time management software to track productivity and also as a method to be sure team members are staying on task. Creating that balance, implementing that oversight, is necessary not only for our internal operations but to let clients know we hold our team members responsible. At the same time, we don’t want our team members scared to step away from the computer for a second, and so we rely on productivity and team leads to make judgement calls if there are concerns about a team member’s time use.

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Crossover

The most difficult part is helping your team stay motivated and feel part of a team when they have never met. In the office, a sense of camaraderie is hopefully achieved through daily interaction and rallying around a common goal. The same is true for remote team, minus the daily interaction in the traditional water cooler sense.

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Dell

Ensuring the team member does not feel forgotten or overlooked in regards to regular updates to development opportunities based on them not having the face-to-face relationship.

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DevriX

Working with less experienced people, communicating properly online with other team members, following company policy and standards, understanding goals and vision, nurturing motivation outside of an office.

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DVMelite

The biggest challenge is to find people who will fit into our culture and are ready to work hard for a great cause.  

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Edgar

Making sure everybody has the same access to information, which is a matter of making information both available and easy to find. We manage this by using tools that allow us to centralize information – in the past, that’s included private wikis, but has shifted over time toward Google Drive and other internal help doc databases. (We’ve found that as a company scales up, wikis can grow unwieldy – information is added without the central oversight it often needs to stay organized.)

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Eyeo GmbH

Keeping everyone happy and connected, not forgetting people.

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Flex Professionals

Remembering to create and allow for opportunities to share and exchange information so everyone is kept in the loop, accountable, and takes pride and ownership in the growth of the company.

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FMTC

There’s a lot of communication done in an office that you don’t have with a remote team. The unspoken communication is huge, and we just don’t have that when both parties are behind a screen. I believe that building trust with a remote workforce takes much longer versus a traditional office, but can be destroyed much quicker.

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Fog Creek Software

Managing a remote work force isn’t terribly hard as long as your rapport with your remote employees is strong. Doing the initial work during onboarding and offsites to build trust amongst employees and managers goes a long way toward making remote management simple.

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Formstack

The biggest challenge is the “if only we were together (physically)” thought that pops into your head on those days when you want to call a 20-minute brainstorm or quickly tackle feedback or a conflict that arises. It takes effort to delete that incorrect belief from our brains and remember that we just need to develop ways around those perceived limitations.  

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GitHub, Inc.

At GitHub it’s important to us that we look after our employees. We’re not just in this for short-term productivity, we’re in this for the long-haul, and that means that you need to view the health of your people and teams a bit more holistically.

What we’ve found is that it’s actually quite hard to ensure people are making full use of what’s offered to them. It’s easy to view policies as just sets of rules about what you can or can’t do, but in a distributed company you rely on written documentation much more than in non-remote companies, so one of the challenges we’re facing as we grow is how we can make sure our management practices and internal documentation are focused on encouraging healthy behaviour. That’s the only way you’re going to get sustainable productivity and growth in the long-run.

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GobySavvy

I think communication is the hardest part. We don’t have the power to walk into someone’s office and ask for an update or motivate. However with great applications like Slack, communication is becoming more seamless.

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Goodway Group

Getting everyone to not use their mute buttons on group calls. It can be difficult to have meetings that require brainstorming and input from many on a big group phone call. It is difficult to replace the value of in-person interaction for these kinds of meetings.

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Greenback Expat Tax Services

Our team members span the globe, from Mexico to South Carolina, from California to Indonesia. Our biggest challenge is accommodating the different time zones and ensuring consistent, productive communication. Skype calls are difficult to schedule. It forces team members to be flexible and accommodate the different time zones. For example, our monthly management meetings are generally at 6:30pm EST, which is 6:30am in Indonesia! Once again, it goes back to hiring the right people who are committed to making it work, even when it’s less than convenient.

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Hanno

To me, the hardest part is not ‘managing’, because if you try to manage and control people, you’ll inevitably fail to build a strong remote team. The hardest part is trying to empower people to manage themselves, and also give them a sense of unity and connection to the team as a whole. When people are feeling positive and excited, things tend to take care of themselves. But in stressful, tougher times, the hardest thing is trying to keep up morale and avoid the onset of loneliness and isolation, which is a particular struggle in a remote team.

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Help Scout

There’s arguably more overhead placed on the shoulders of leaders in a remote company. The hardest thing is to acknowledge the overhead and be really organized about it. Being transparent and keeping everyone connected is something leaders in your company have to be constantly on top of. Of course, the wonderful tradeoff is a very productive workforce if you get this stuff right.

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Hippo Education

Making sure we build relationships offline as well as online.

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Hubstaff

Sometimes remote workers just don’t have that much time for your company. They may have multiple clients, be traveling the world (you never know with digital nomads–they could be in Alaska or Sydney) or simply not want to work that many hours in the day. 

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Inpsyde GmbH

Sometime it would have been good to go after work in a pub or somewhere else and talk about a project and come up with some solutions or also find out what’s the real problem of the worker, is it private or business. Reading between the lines is much harder in a remote team.

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Intridea/ Mobomo

Communication and understanding people’s personalities via text and email.

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iTutorGroup

Ensuring that policies and advice given by the company conforms to the cultural and ethical norms of a global workforce. Empathy is required when working with a very large and diverse workforce.

Jackson River

It’s about making sure there is enough time to actually support staff, and that there are effective processes around what we expect our managers to do (a general frame for managing relationships, performance, feedback, and outcomes). This is as specific and prescriptive as how frequently they need to check in with their staff and how they can be supportive without face-to-face contact. Communication is key.

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Knack

Always the communication. This is this the hardest part for any workforce; remote just amplifies the stakes.

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Knobs.co

Managing outgoing sales efforts.

LiquidSpace

It can be tough to make sure everyone, across departments, is on the same page about the big picture initiatives in the company. We resolve this issue by having all-company meetings, training sessions, and weekly sprint reviews.

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Lullabot

Finding the balance between asynchronous and synchronous communication. It is tempting to try to do everything possible with asynchronous communication (e.g. email, etc.) but there are so many kinds of things that hugely benefit either in quality or efficiency through synchronous communication.

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Mavens

Ensuring that there is a common understanding of practices and procedures to help everything run smoothly.

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Melewi

Timezones can be tricky. As the team grows, timezones are getting harder to manage.

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Modern Tribe

One of the hard parts we’re working through now is adding layers of management we didn’t have before. We’ve grown a lot over the past few years, and that means that now there are more moving pieces to look after.

We recently introduced a director level within the organization, which has overall been pretty well-received by our team. The challenge was communicating what that meant to everyone, since it’s not like we can just gather everyone in the break room to make an announcement. We chose to share the announcement at our team retreat earlier this year so we could have an open conversation and address questions with the bulk of the team. We followed up with announcements for those not present at the retreat.

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Mokriya

Developing and maintaining culture as we grow. The larger Mokriya becomes the more important it is to stay true to our values and hold onto our culture.

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NodeSource

Making sure people are consistently aligned with the mission.  People can start to lose track as they get heads down on the day to day stuff, so maintaining alignment and providing context on the bigger picture is a full time job as CEO.

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Packlane

I’ve only ever managed a remote workforce, so I don’t know whether the challenges are specific to a remote workforce, but velocity of work, building rapport with a workforce that you don’t have much face-to-face interaction with, and, to some extent, ideation can be more difficult with a remote workforce.

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Pagely

This may sound like a humblebrag, but our biggest challenge is enforcing our work-life balance culture. We are growing so fast and there is alway work to be done. Remote workers tend to over do it (work). So being mindful of when someone is running out of gas and not letting them crash is our biggest concern. We may not always be able to push them to relax right then, but when the project or issue is over we, as a team, will force them to take few days or a week off and re-charge. Everyone steps up to cover that person in their absence, as they know they may need a break at some point as well.

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Plex

Not being able to have regular face-to-face one-on-one meetings with people is a bummer.  Nothing beats grabbing a lunch, beer or coffee with someone and just getting to know them.  That said, getting people together at least once per year helps a lot.

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Project Ricochet

The hardest thing for me is that the tools we use to communicate can contribute and enable an organization-wide urgency addiction that makes it hard for people to prioritize, focus on their craft, and achieve a flow state in their work. Slack, for all its greatness, can cause people to jump from conversation to conversation and it can very easily lead to burnout.

At Ricochet, we spend a lot of time making sure people don’t get sucked into false urgency. Each team member makes a plan at the start of the day and we go over their ability to achieve their plan during our one-on-ones. If they are unable to actualize their plans each day, it means they either need coaching on doing what they set out to do (or discerning between true urgency and false urgency), or the organization needs to get better at its own planning and needs to stop throwing urgent tasks at people (which can easily lead to burnout).

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Referral Rock

It’s harder to have a general “pulse” of your team. You can’t see their body language and moods as much on a day-to-day basis, so you’re left with fewer signals to interpret how people are feeling.

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Remote Year

One of the challenges in managing a remote workforce is employee engagement. To be successful at Remote Year, employees need to be both collaborative and autonomous. More importantly, they need to know when to wear each hat. We spend a lot of time in the hiring process looking for these traits, and we continue to find ways to support our team members globally as we continue to grow.

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Simple [A]

Knowing what to do with all the awesome.

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SitePen

The hardest part about managing a remote workforce is the propensity for terse communication.  Often times, people are chatting, trying to quickly accomplish something or just giving quick answers and through non-verbal communication channels, these can come off harshly or seem to lack empathy.  It’s important to remember the person sitting at the other end of the interweb is not a bot and to recognize how they may be perceiving certain things.  Face-to-face communication is often much friendlier and cordial so sometimes remembering to take a little extra care can be difficult.

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Stack Overflow

Building rapport with new coworkers can be difficult when you don’t get the casual social interactions you often get for free when everyone is in an office. You have to make an extra effort to reach out to new people and make them feel like they know you personally, not just as their boss.

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StudySoup

When something goes wrong, there’s usually somebody on Slack to help with the issue. But in some rare cases when you really need something, you may not be able to get a hold of them which can be stressful.
Also, reading body language is really difficult in remote teams. This means everyone needs to work extra hard to push themselves out of their own communication comfort zone in order to meet people half way and engage in productive interactions. It’s easy to read into what someone says or does over video chat or Slack, and create a negative narrative around that. We all just need to be aware of that and remind ourselves that everyone is in it for the benefit of the company!

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Summit CPA Group

It is not for everyone.  You have to be able to hire effectively and be quick to realize that if it is not a good fit for the employee.

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Sutherland Global Services

Sensing everybody’s mood, level of motivation, identifying issues before they develop.  With an on-site team, you get to take advantage of facial expressions, body language, etc.  With the remote team, there are a lot of subtleties, often taken for granted, that are missing.  Managers really need to be good listeners and learn to “read between the lines”.

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TeamGantt

The hardest thing is just making sure to stay in touch with everyone and make sure everyone knows that they are part of the team and that their role is very important.

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TeamSnap

Scheduling meetings can be tricky because we cover a lot of timezones and some people may choose to work very early or very late, depending on their preference. This may be more of a feature than a bug, since meetings are generally a waste of time.

The other hard thing is convincing new employees that they really do have the flexibility to work where and when they want. If you want to work from Portugal, work from Portugal; you don’t have to ask for permission. Just get your work done.

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Teleport

All people need to make very conscious decisions about personal work time allocation, and the time they spend on communication with the others. For example, if someone is building the most amazing and useful feature for 2 weeks, but doesn’t report back to the team in group chats, for the others it looks like they are absent. Over time they will lose buy-in, and regret their inability to contribute. On the other hand, if you spend 2 hours evangelizing what you do, you will only _do_ it at 75% of your workload. This needs careful tuning to get right for both individual productivity and overall team output.

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The Cheat Sheet

It takes extra effort to build a rapport with everyone. There are no incidental conversations that happen on the way to the break room in a virtual office. We addressed this need by creating a “virtual watercooler” on Slack, among numerous other culture-building activities.  A strong culture is very important to us at The Cheat Sheet.

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Time Doctor

Surprisingly, one of the hardest parts of managing a remote workforce is that as the company grows, working across teams becomes a challenge. For instance, many members of the marketing team may not know any of the developers. Keeping an updated org chart is a must-have.

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Timely

Not seeing them in person every day. Most people think the hardest part about managing a remote workforce is about productivity. It’s not. We have incredibly talented and interesting people on our team. As a founder, you get to selfishly hire people who you’d hang out with whether you worked together or not. So not seeing all of them every day is a tad sad panda. We may have to double down on retreats.

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TNTP

Working from home can be isolating, especially for staff who have never worked remotely or for TNTP before. You have to be proactive about building relationships and friendships across the organization. It can sometimes take longer than we’d like for a manager to realize that someone is doing something inefficiently if you’re not in the same space. And it’s easy for the hours to get long when you don’t have to formally pack up and go home at the end of the day.

These challenges have forced us to get really intentional about building a shared culture for everyone at TNTP, which we reinforce through virtual team-building (see more above), our annual in-person conference, site visits for staff to see what different teams across the organization are doing, and our signature experience for staff – Leadership Lab – a series of trainings to develop leaders at all levels across TNTP.

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Toptal

If you’re a typical startup, <10 people sitting in an office, then with everything that happens, everyone always knows about it. So how do you create that cohesiveness at a remote company? If part of your workforce is remote, do you start copy pasting things that go on in the office in chats to the people who aren’t physically present? Any engineer will tell you that wasting time on repetitive things like this isn’t a good solution. Companies looking to embrace remote need to figure out good ways to address this, and there are plenty of mistakes we’ve seen people make.

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Tortuga

The hardest part of management is keeping everyone on the same page. As I mentioned above, we try to do this weekly, monthly, and quarterly. As CEO, the highest leverage thing I can do is focus the team’s efforts on a single problem or area of opportunity. My job is to get everyone in the boat and rowing in the same direction.

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Trade Conductor

I do not find it difficult. But you have to pay more attention to how you communicate. People don’t often see your face and therefore only see the written word. It is my experience that thank-you notes, short sweet messages, and birthday acknowledgments get much more relevant and important when you are all remote.

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Trello

Ensuring a consistent company culture and keeping everyone feeling connected.

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Ultimate Software

One of the hardest things is making sure you have a good set of managers overseeing the remote employees, and making sure they are fully trained on how to manage remote employees.

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Ushahidi

Accountability tracking. Time zones.

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VIPKID

The IT issues. China to U.S./Canada Internet connections are hard to manage, and it’s a good thing we have such a talented tech team to handle that.

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Vork Inc

The hardest part is maintaining discipline for management to make sure that we are active in all the key areas of the business all the time. It is also hard when the CEO travels so much to maintain a regular schedule of activities.

Wordfence

We haven’t really had many challenges in management but we’re also still a small team (8 people full-time with several part-timers or contractors). We’ve done a great job of evaluating people before they join us and so we don’t have a situation where anyone needs to be “managed”.

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Workfrom

It used to be finding reliable, productive places to get work done—but we nailed that problem 🙂

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Working Solutions

Learning how to effectively communicate remotely takes practice.  How much to share, how often, who to include, and how to ensure the intended message is received.  Knowing when to step in and when to let go is also a challenge.  In my experience, people work better when they are armed with goals and the tools they need to achieve them, they know you have their back, and they are given the space to do what’s been asked of them.

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World Wide Web Hosting

Communication – without a doubt. Since the “water cooler” talk isn’t possible, we provide a wide variety of channels and tools for staff to communicate. I’ve already mentioned email, HipChat, and Google Hangouts; we also have a staff forum and a social media style site for informal discussions. We have an internal blog for large announcements and official company business and announcements.

One of the most fun things we have done is have two in-person staff meetups per year. We started this a couple years ago, and they have been extremely beneficial. Since we are global, we opted to have one meetup in the USA and one in Europe to allow greater attendance across the company. By promoting an in-person meetup, we’ve allowed our staff to enhance their relationships with each other in a fun, non-work setting. This has translated to better working relationships, which in turn increases morale and productivity.

X-Team

It’s a bit of a tie for me — the two things I struggle with most are satisfying each person’s needs as a remote worker, and secondly, maintaining the trust you have in people.

Each person has different needs, and when they work remotely, it can be really challenging to satisfy everyone. Some people love working remotely because they prefer less human interaction. Others though can really miss the human interaction and get emotionally affected when you pull it away. Making sure you have opportunities for human interaction beyond text is important, but you have to balance it with those who want less of it by not requiring everyone to participate in it if needed.

Secondly, trust is always a challenge. As I’ve written before, journaling is the most effective way to avoid trust issues among your team, but even with journaling, you’ll have moments of concern that not enough work is getting done.

Sometimes these moments are well warranted, but often times they are unnecessary, especially if there are decently consistent journal updates happening. I’ve had to let people go who take advantage of remote working and deliver very little, but it’s important you confirm that your concerns are real and you’re not just having a moment of “Uh oh, I can’t see anyone working…are they actually working today?” Those moments will happen, and take note only when you feel that way consistently (as in two weeks in a row) about specific team members rather than assuming your entire team is unproductive.

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