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Remote Company Culture


published / updated
May 10, 2019 / Dec 9, 2019
also available at


W hereas remote used to be something that was frowned upon or offered only for overseas contractors that weren’t perceived as part of the team, it’s seeing a resurgence as a new, hip benefit. It feels like there are so many companies offering the ability to work from home or work remotely nowadays. Some companies, like us at Chatra, are entirely remote but offer a benefit to work in a coworking space as needed. Others, like Trello, have small office spaces of their own, but otherwise allow heavily for remote work. But, for companies that are just getting going with creating their remote cultures and teams it can be difficult to know where to start. We’re here to help! We’ve put together tips and tricks about all the different aspects of building and maintaining a healthy remote culture that will help guide you towards the best fit and process for your team.


Remote Culture: What is it
and how do you build it?

C ulture is defined, in Merriam-Webster, as: “The customs, arts, social institutions, and achievements of a particular nation, people, or other social groups.” Remote culture is not just how the people on your remote team talk to and interact with individuals on the rest of the team or within themselves.

Remote Culture: What is it and how do you build it?

It’s how the company conducts itself around the idea of “being remote” and what it means to everyone as a whole. For your company’s remote culture to be good, even the people who aren’t remote need to care about it and recognize it as something important and integral to the business. So, how do you do that?

First, there are differences in the cultures of entirely remote and partially co-located companies. When an entire company is remote, everyone is on a level playing field, and it doesn’t feel like any one team (whether that be the remote team or the in-office team) is at a disadvantage. Basecamp was one of the original companies to pioneer remote working and have created many of the policies that whole-remote companies use to function.

When you have both co-located employees and remote employees it makes for a complex situation where you need to ensure that both groups are treated similarly and offered the same types of benefits and perks. For example: if your in-office employees get lunch catered to them every Friday, what perk do your remote employees get that is comparable?

These types of considerations are incredibly important when considering building a remote team, and creating a culture that is representative of your company values. Building remote culture means taking the same time and effort that you would for an in-person team to ensure that the traditions, practices, and values that you hold important are carried through, even though they are not physically in the office.

Making traditions and values stick when people aren’t always together can be really tricky, but creating regular practices, like a weekly video chat where everyone hangs out together, or a special treat that the remote employees get when there is an in-office party can go a long way towards creating something strong and lasting.


Remote vs. Office

T here are benefits and opportunities to both working remotely and working in an office — neither of them is perfect. And, if you’re trying to create the ultimate culture, as mentioned above, you’ll need to take into consideration the unique implications of both. Here’s a breakdown of the pros and cons of both working in an office and working remotely.


Working in an office is the traditional standard method of employment. It is familiar and pretty well-established as a practice. While there some offices that skew outside the norm (we’re looking at you, startups with ping pong tables!), for the most part, people know what to expect when they take an office job.


  • Able to quickly collaborate with teammates.
  • Can visually manage in-person employees.
  • Easy to build culture if everyone is present.
  • Clients can come and visit.


  • Quite easy to become distracted.
  • Expensive and hard to scale office space.
  • Lose out on amazing talent not directly near you.
  • Miss out on international support hours, unless you hire overnight employees.
  • Lack of life flexibility for things like appointments, family emergencies.


Working remotely is still somewhat new. While lots of companies are doing it and they are all willing to share what has or hasn’t worked for them, it can still be a black box for teams looking to make it their own. Here are a few of the pros and cons, both from a company and an employee perspective, for working remotely.


  • Availability for talent pool is much wider.
  • Do not have to pay for office space.
  • Risk of distraction is much lower for remote employees.
  • Potential better quality of life for employees.
  • Reduced stress for employees.


  • Employee isolation.
  • Potential difficulty tracking employee performance.

Myths and misconceptions
about remote work

A long with the factual pros and cons about working remotely or working in an office, there are also plenty of rumors and misconceptions about remote work that can make it hard to get off the ground at a company. For example, if you are working at an entirely colocated company and you want to make the case for your team, or the company as a whole, to go remote, you’d likely come up against some of these myths as reasons why it wouldn’t work.

A “Water Cooler” Is Critical for Culture

There is an outdated conception that having something like a “water cooler” or a common space for people to congregate is important for building culture. This stands on the basis that people will not be able to have sporadic, in-the-moment conversation unless they are all co-located and working in the same place. While this may have been true in a time before technology like we have today, with things like live video chat and internal chat services like Slack, it’s easy to cultivate personal relationships and culture without being in the same space.

For example, creating Slack channels, which are effectively just chat rooms, on certain personal interest topics is a great way to allow members of different teams who are remote to build relationships with one another. Conversations that would normally occur around the lunch table for people working in an office get to happen in Slack, or a weekly video chat hangout for remote employees. Giving both sets of employees, remote and in-office, this kind of outlet is critical for culture, yes, but the space in which it takes place does not need to be located in an office to be successful.

Our “water cooler” in Chatra is a #random channel in Slack: we share links to interesting posts, photos, memes, and discuss different things that are not related to work.

People Are More Productive in an Office

It’s a common misconception that if you work from home, you’re going to be distracted by all of the things you have to do at home: like watch TV, or work in your pajamas, or hang out with your kids. But, people who work from home, because of the nature of their role, have to be particularly stringent for where and when they work to avoid running their home life into their work-life. Given that, efficient remote employees are excellent at timeboxing and planning out their day.

Conversely, when in an office, there is tons of distraction. Most offices of start-ups, for example, have fun game rooms, or even nap rooms (like Hubspot) which make it easy for employees to spend all their time there. At face value, while it might seem like spending all of your time at the office is that bad, it’s likely they’re not necessarily using those long hours to work, but using the awesome amenities available. Just because someone stays somewhere longer does not mean that they are working harder or are more focused than someone else. Also, people who work remotely often do work long hours because it is easy to do so: they don’t have to commute and it is easy to lose track of time when you are somewhere comfortable and familiar (like your house!).

You Need an Office for Work/Life Separation

Many people assume that people who work from home have little work-life balance — after all, as noted in the previous section, it can be easy to lose track of time when you’re working in a comfortable, familiar place. It’s true: if you don’t pay attention, it can feel like you’re never leaving work, especially if you do not set up a space to have for work. As a remote employee, it’s incredibly important to set up a workspace and set up routines for yourself just as you would if going into the office.

For example, for people that go into an office, they often get up, make breakfast and get ready, and then commute into work. People who work remotely should do something similar: wake up, get dressed like they would if they were going to work, and then go to their desk or other designated workspace. Creating a physical space and routine helps to enforce the mental boundary between home and work — when you leave your workspace, you are no longer in work mode and are able to be home.

Similarly, work-life balance is becoming close to impossible for all employees, whether remote or not, with tools like Slack and Stride. Asynchronous communication means that anyone can reach a co-worker at any time, thus breaking down the barriers of what is defined as “work time” and what isn’t.

Being in an office makes meetings easier

When people think of meetings, it’s usually some version of a board room meeting with everyone sitting around a table. If someone isn’t there, in the past they would get dialed in — a lone person waiting to speak while all the people actually present in the room talking over them and forget they’re there. But, that no longer has to be a reality.

Video conferencing tools like Zoom and Appear.in make it easy for people to speak face to face, even if they are continents away from each other. Being able to interpret people’s tone and facial expressions is a total game changer when it comes to remote work and remote meetings. For companies that are combined with both remote workers and workers in the office, being able to hop on a video call means that the remote employees feel more present and engaged, and as though their input is meaningful and important. For entire remote teams: their offices become the video chat and whatever real-time chat tool they use.

So, while everyone being in an office can make meetings easier, it’s only because the company isn’t using the appropriate tools to equip everyone with an equal standing ground. Giving everyone a face and ensuring that they can see everyone else’s face means that everyone is able to share their perspectives equally.

Working at home is distracting

It’s easy to think about all of the things that you would do if you were allowed to work from home, especially if you’ve never done it. “I’d watch every episode of Lost!” you’re thinking, “I’d sit in my pajamas all day long!” you muse to yourself. But, that’s actually not the case, or at least you wouldn’t be able to do it for long. As we talked about above, building routines and healthy habits are integral to the success of remote employees. So, likely, if you were watching TV all day your work performance would decrease and your boss would be coaching you on how to improve. You would be finding some way to get better.

The long and short of it is: working from anywhere can be distracting. Working in an office, for some, is incredibly distracting, just as working at home may be distracting for others. As long as you hold yourself accountable to performing well at your job, no one place will be more distracting than another — you just have more flexibility when working from home, so you need to be more rigorous with your own boundaries and allowances for yourself.

It’s impossible to cultivate team spirit while working remotely

You do not need to be right next to someone or near them in order to build relationships. Long distance romances all around the world prove this every day. While it takes more work, effort, and intentionality to maintain a relationship with little in-person contact, it’s easy to do if the people that are in the relationship genuinely care. That goes for both work and personal relationships: a company needs to put in the effort to support and connect their remote employees just as much as remote employees need to put in the effort to communicate and connect with the larger ecosystem. At least if there are both people in the office and people working remotely.

Whether your team is entirely remote or you have a mix, there are definitely things that you can do to build and maintain a great company culture. One thing that a lot of companies do is a weekly remote gathering over video solely for social purposes. This is an excellent way for both in-office and remote employees to talk, get to know each other and build friendships outside of their regular work roles. Creating camaraderie like that can be extremely beneficial for inter-team dynamics.

Another thing that a lot of companies do is annual or bi-annual retreats. Even companies that do not have any remote employees do this, but for those that do have remote employees having retreats is a hugely impactful way to bring people together, create meaningful memories and re-instill company culture and values if they’ve started to fade from people’s memories.

Remote workers can’t be managers

People who are remote are just as capable at being managers as people in the office — especially if their team includes other remote workers. Given the progression of modern technology, all of the things that managers do in an office can be done over the computer as well. If a manager needs to provide constructive insights, they can do so over video chat, if they need to ask a quick question they can do so via company chat. There is nothing within a manager’s role description that should mean they are unable to work remotely.

You can’t train people remotely

Similarly to the above: it used to be that the technology didn’t exist to allow training to be done other than in-person. People needed to be able to sit face-to-face and go through information together to be sure that someone got it. Now, though, there’s so much out there that enables the ability to work remote, or even for people to learn asynchronously if they’re in another timezone.

Documentation as a resource is an evergreen tool that all employees can use to be better trained and reference later on during their work. Video calls have made it so that managers can train people and read their facial responses in order to better prepare and present. While it’s always good to start off with some in-person time, training remotely is far from impossible and can actually be a really helpful offer for candidates that are unavailable to work any other way due to unforeseen circumstances.

Working at home is unhealthy

The conception that people who work from home all sit in the same pajamas for weeks at a time is a strong one. There are tons of comics about it, and memes travel around about it regularly. While it is true that remote employees, just like everyone, can cultivate bad habits, they are not any more prone to it than anyone else.

For people just looking to get into remote work, it is important to set boundaries and reminders for yourself for self-care. Without the normal social cues of, for example, everyone getting up to go to lunch, it can be easy to forget to do things that are important. Many remote workers will set alarms to take a midday break or will work from coworking spaces or cafes in order to get a change of scenery away from their home office.

A quick poll in our #random channel at Chatra showed that many of us need to move more during our remote work day. To compensate for our desk job, team members have developed the following healthy habits:

  • Our customer champions try to walk as much as possible and go to the gym whenever they can.
  • Our CEO rides a bicycle a lot and walks his kids to school instead of driving there.
  • Our COO has a fitness machine at home.
  • And one of our engineers gets his share of exercise by playing VR Beat Saber :—)

Remote workers don’t know how to act socially

This is like saying that all introverts don’t know how to talk to people. While it can be easy to paint everyone of a certain group in one wide swath, usually those types of generalizations are not true. They can even be harmful!

It’s true that remote workers spend a lot of their time in isolation but, just like most other people, they need to talk to people for their job. Just because someone doesn’t see people in person every day doesn’t mean they don’t talk to them or that their social skills have atrophied. In fact, it’s usually because of the fact that remote people infrequently get the opportunity to work with people in person that they are so jovial and buoyant when they get the opportunity to.

Remote employees are disconnected and have no real impact

The last, and perhaps most harmful, misconception around remote work is that remote employees are completely disconnected from their companies and actually have no impact on what’s happening. This is mostly applicable to companies that have both remote and co-located employees. Creating a dynamic that places office-based employees over remote ones is problematic and should be avoided at all costs.

Hiring remote actually opens up the candidate pool to extremely skilled individuals who would otherwise be unavailable — it really allows a company to hire the cream of the crop. So, to say that the people hired have no impact just isn’t true, unless the company does a poor job of integrating remote employee’s perspectives and work.

At Chatra, we have been working remotely from the very start and we’ve built a friendly and united team where everyone can express their opinion and be heard. Together, all across the world, we work to bring you the best messenger tool for websites. Give Chatra a try and see for yourself!
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Common mistakes where
remote companies fail

It is easy to make mistakes, especially when you are trying something new. Oftentimes, there are iterations on a product or service until you get it just right. The same can be said for culture and integrating new policies (like remote work) into a company. Here are some of the common mistakes where companies that are integrating remote fail or miss the mark.

Common mistakes where remote companies fail

Hiring a great worker instead of a great remote worker

As you might be able to tell from the list of misconceptions around remote work, it takes a special type of person to be effective while working remotely. When hiring for remote, it’s important to look for a few things:

  • Self-motivated, maybe they’ve been their own boss, been a manager, or worked remotely before.
  • Communicative, as a remote employee it’s important to be extremely competent at communicating what they mean.
  • Brave, advocating for their own needs and being able to speak up about things they’re passionate about is necessary when working remote.
  • Flexible, oftentimes remote employees are hired to cover strange timezones, but even without that, remote employees need to be flexible with their expectations and communication with other team members.

Then, on top of those, you should be looking for whatever is in your regular competencies for a candidate. Many companies overlook the aspect of remote and assume that someone who is a good worker will also be a good remote employee. That is not always the case and can sometimes lead to great culture fits that end up being poor performers because they are unhappy or don’t know how to motivate themselves when outside of an office.

For example, we had to part ways with two great engineers who just couldn’t get used to working remotely and decided to switch back to working in a traditional office.

They didn’t hire for culture fit

On the flip-side, sometimes companies find someone that is so experienced with remote work that they hire them, thinking they’ll make an excellent impact on a remote organization. While sometimes this can pan out well, most of the time if you aren’t looking for culture fit, the hire will eventually churn out.

Even people that aren’t in your office impact your company’s culture. They are talking in your work chats, they are engaging with people over email or video, maybe the engage with your customers — it’s important that everyone who does any of those things be representative of your culture. Cohesion is king when it comes to building your company values and what you stand for. Don’t sacrifice that for anything.

Employees get burnt out

Boundaries can be hard to set, and it’s easy for remote people to work extra long hours because they don’t have to commute or leave home. It’s tempting to be the rock star on the team that gets everything done or comes in in the clutch when there’s an emergency. But, doing all of that and upholding all of those expectations can be exhausting, and employees can get burnt out.

The best way to combat this is to have managers specifically paying attention to burnout and depression in their team members. In one-on-ones, maybe have managers ask about things like routines, leaving the house, or directly about burn out. Employees might not feel comfortable outright saying that they are having a hard time, but when asked (especially if managers do it regularly) they may feel comfortable opening up. That way, it can be caught and fixed before they decide to just leave.

Didn’t focus on building culture or teams

This is especially true for companies that are entirely remote and do not have any in-office component. When building a company of people that are all fairly independent and self-driven, it can be easy to forget to pay attention and create a culture or a value of teamwork. That being said, surprising no one, culture and teams are just as important at an entirely remote company as they are at a company that is office-based.

Culture helps to provide a north star for everyone to orient themselves towards. Without it, there’s no direction or guidance to people’s projects and no alignment or trust between coworkers. Does that sound like a recipe for success? More like one for disaster. Without culture or a common guideline, people don’t know what to work on, and without that knowledge they might as well be working on nothing.

Poor communication processes and tools

Companies that employ remote workers need to be at the forefront of technology. The office of the remote employee is Slack, Zoom, Stride, and Trello rather than a desk and fancy ergonomic chair. So, when a company with remote people fails to implement the tooling necessary to support appropriate communication, it silences a whole important group of team members and makes it difficult for them to do their job.

If you are a company that’s looking to go remote, there are a few things that you should focus on building space for before you do:

  • How will remote employees be involved in meetings? How will they hear and be heard? How will they see and be seen?
  • How will people know remote employees work hours so they don’t get disturbed when they are off duty?
  • How will you loop in remote employees for office events, such as a day trip to a beach, and how will you compensate them for missing out?
  • What hardware do you need in the office to communicate effectively one-on-one with remote employees?

Having these things hashed out prior to bringing on a bunch of people that it will affect will make for a much better experience for your employees and the company as a whole.

No goals or accomplishments communicated

Because remote workers aren’t in the office, it can be difficult for in-office employees to see what they’re doing or recognize their achievements. It’s incredibly important to communicate remote workers successes (and failures) just as everyone else’s is communicated. 15Five’s High Fives feature is one of the great ways to do this. It allows every employee in a company to give props to the people that they work within a way that the whole company can see.

Strong management is imperative for remote employees, so being super clear on goals and expectations is also very important. Often times these come out and are reinforced naturally when working in an office, but that’s not the case when someone is remote.

Focusing on personal benefits rather than professional

Many people create remote functionality for themselves because they see the personal benefit of working from home instead of the professional benefits. So, for example, they see that they could actually travel anywhere in the world and work, instead of recognizing that they are afforded the mental space to really dive deep and focus every day, or that by hiring people remotely they are able to hire the best candidates available anywhere, rather than the best candidates available just in their city.

Focusing on the personal benefits takes you out of the value of what you’re doing. It’s a privilege to be able to work remotely, and when you start to lose sight of that you lose sight of your goals and all of the work you have to do to get there.

Overcompensating to appear productive

People are always afraid to be the one that isn’t doing enough. Because of the sometimes low visibility into what remote workers are doing as we mentioned above, they can be tempted to work and go above and beyond to prove their value and worth to the company. That’s awesome for the company, but for the employee, it’s a quick road to burnout. It’s important to train managers to watch for this and communicate often around the benefits of self-care. Leading by example is the best way to do this, so remote managers should be especially cautious about their actions and how they may be perceived by their direct reports. Do not over-aggrandize the work you have done, don’t pull 12 hour days because it makes you look like you’re dedicated. It doesn’t, and once your employees start to do it, it’ll be even more difficult to break their habits.

Assuming remote employees are always available

Just because a person works from home does not mean they are always available. While it’s true that their light next to their name in your company chat might be on, they might not be able to help you or talk to you at that moment because of something they’re working on. Be mindful of people’s schedules and try to respect them.

Companies can do a better job at this by actually tracking or documenting remote employee’s schedules and communication preferences. That makes it easy for both people in-office and remote people to know what the best way to communicate is and when to do it.


How to hire remote workers

We talked in a previous section about how important it is to hire good remote workers rather than just good workers, but didn’t dive too deep into what makes a good remote worker or how to hire them. Did you think we were going to leave you hanging? Here are some tactics for both finding an excellent remote hire, and then hiring them.

Find people that are self-starters or have already worked remotely before

Working remotely gives people a lot of freedom. If you give that much freedom to someone who isn’t used to having it or isn’t good at motivating themselves, you’ll end up with an unproductive hire that doesn’t actually contribute anything back to your company. So, when hiring someone for a remote role, it’s good to look for someone who shows signs of being or talks a lot about self-starting. Other great things to look for are people that have worked remotely before successfully or people that have run their own businesses. Both of those types of people will likely have the skills that they need to set boundaries and routines that are so important for a healthy remote working lifestyle.

They are extraordinarily communicative

The person that you hire should almost be annoyingly communicative in how much they want to talk and share. Remote employees can often be isolated and it’s important for whoever works for you to be able to advocate for themselves and speak up about the things they care about. Otherwise, amazing perspectives may just be drowned out or lost in the noise because they didn’t feel like they were able to communicate about it. That’s no good!

When interviewing, ask questions about communication and try to dig deep on why they make the communication choices that they make. There are some great examples for questions that you can ask in the sections below.

Where to find people?

Inbound marketing, as Hubspot writes, is one of the best ways to get amazing candidates to apply at your company. 75% of job seekers start their search on Google, and it’s best to meet people where they are if you want them to apply. So, create excellent content. On social media, market yourself as a remote-first company who has employees that love to work there, and has awesome benefits. For example, if you do host an annual retreat, make sure that you take lots of pictures and have employees use a specific hashtag when sharing about it. This kind of inbound attraction to potential new employees is an excellent way to find people with similar values to your own.

Referrals are another excellent way to get people interested in your company. If you have employees that love working for you, ask them to refer their friends, family members, or other people that they think might be a great fit. You’ve already got at least a little bit of the vetting done if you have your employees do a little bit of the work of sifting through candidates for you.

Lastly, posting in specific industry channels or on job sites can be a helpful way to get candidates. Many of the applicant management systems now, like Lever and Google Hire, offer the ability to push automatically to the main sites where people go to look for jobs. Beyond that, though, large Slack channels like Support Driven are helpful, as well as sites like remotive.io or weworkremotely.com. Making yourself as present as possible on the internet if someone searches for you is the best tactic.

What are the best questions to ask in a remote interview?

Once you’ve had individuals apply, you’re finally at the interview stage and ready to talk to them. But what are the best questions to ask and how should you, as the interviewer, interpret the answer? We’ve got a few ideas for you:

  • What attracts you to working remotely and how long have you been doing it? This gets a little bit into the space of figuring out whether someone is looking for this job for personal or professional benefits. Many people see working remotely as an opportunity to sit around at home and do nothing with their day, while others see it as a way to get themselves ahead professionally while still living close to family or other things that they want and need. Listen carefully to what the person you are interviewing says here because it’s likely very indicative of the type of remote worker they would be on your team.
  • What was the last thing that you taught yourself and why? This question helps you discern how much of a self-starter your potential future employee is. If they can’t think of anything that they’ve taught themselves recently, it’s pretty unlikely that they’re going to be a good fit for a remote role — if they can’t drive themselves to learn through curiosity, how are they going to push themselves to succeed in a fairly free-form role? Listen, also, to their incentives to learn: what pushed them to learn the thing? Was it someone else telling them what to do, or did they take the initiatives themselves? It’s important to find someone who learns things because they want to and see the value in learning, not because a job or partner asked them to.
  • Tell me about a time you had to work with another team. What was your role and how did it go? The main thing that this question is testing for is what the applicant’s inter-team communication skills look like. Remote employees have to work with most other teams within a company, just like everyone else, so, anyone working remotely will need to be able to work well with team members with all different styles of communication. They have the added challenge of having to communicate without always having the benefit of facial expressions or vocal intonations. So, when communication goes awry for them, it goes deeply awry. Listen to if they speak about overcoming hurdles between communication styles, what they did to be receptive, and how successful the overall outcome was.
  • Tell me about a time where you had an interaction that you thought was resolved, but actually snowballed and became a much bigger issue. How did you resolve it? This goes back to the communication piece above. It is super important to make sure that the person you hire is excellent at communication. This interview question does a bit of digging around de-escalation and the potential hire’s skills around it. In the event that communication goes awry in a remote role, which it can often do in chat or any written, rather than spoken, communication, it’s valuable to be able to understand how to repair the damage and deescalate the situation. Listen, especially, to if the person puts the blame on the other person in the disagreement, or if they claim any ownership for the problems in communication. If they do claim ownership, rather than attempting to place blame on the other person, they would likely be a good fit for a remote role. Introspection and personal understanding are incredibly important!
  • If you were given a puzzle (set of legos, or anything else like that), how would you go about putting it together? This is, clearly, a question about problem-solving. Listen to see how the candidate goes about thinking about something they need to solve (or put back together), and then how they actually take action to make it happen. For example, if they say that they separate out the legos and spread them out across the floor so they can see all of them, that might mean they are more a big-picture thinker that needs to have the lay of the land. If they say that they would follow every instruction in order to avoid messing up the final product, that might signal that they’re a bit of a perfectionist or afraid of failure. See what you can take from this question, and how it applies to the culture that you’re trying to build at your company.

The importance of communication
and how to do it well

In all companies, communication is key. But, in remote companies, communication can be the sword that they live or die by. Given that, while you build your remote team, it’s key to make sure that communication is a big part of your consideration. Here are a few tips on things you can do to ensure that communication is happening and then subsequently do it really well.

  • Daily stand-ups. Do daily stand-ups on a broken-up team-by-team basis and ensure that everyone has the same access to the meeting as each other. So, if you have both remote and in-office employees, make sure that the remote employees have the tools they need to be able to communicate with them. They should have video cameras, microphones, and anything else needed to make it easy for the two sides to communicate. You never want to have a moment where someone says “what did they say?” Once you’ve gotten all of that, keep the stand-ups short and meaningful. You need only to present high-level, high-impact things to keep your team focused and aligned. If someone is blocked on something they should communicate it here, but otherwise communicating goals and what people are working on should be the focus of these meetings. They serve to align people and get everyone on the same page about what your company is working on.
  • Weekly company calls. Every week you should be conducting a whole company call. If you can’t do that because your company is too big, break it up into individual team meetings (and break the team meetings mentioned above into still-smaller functional team meetings). Weekly calls with everyone in the company help to align everyone and build camaraderie between teams. As a note, when you do video calls, make sure that everyone on the call has their video turned on. You wouldn’t go to a meeting with a paper bag on your face, so don’t do what is effectively the same thing by turning the video off.
  • Transparent goals set quarterly or yearly. Every team in your company, as well as your company as a whole, should have transparent goals that are set quarterly or annually. Having goals that everyone sees and knows about aligns individuals on different teams towards a common mission. So, instead of thinking, “hm, well, how does this serve my team?” people will be thinking about how something serves the company as a whole. That distinction is incredibly important and enables people to better assume positive intent in someone’s actions. When you know that everyone is trying to accomplish the same thing, you aren’t going to wonder about whether they are acting in a self-serving manner quite so quickly.
  • Have a water cooler space. Having a place where people can go to talk about stuff that doesn’t work is important. Some companies do this by having video calls where people (remote or otherwise) can drop in before the end of the week just to hang out for an hour or so. Others have lots of different general interest chat channels where people can talk about the things they care about outside of work, like video games, cooking, or building things with their hands. Letting people get to know each other outside of the context of work helps to build rapport and creates a better, friendlier, happier experience for everyone within the company. Even if it means taking a little time out of their work day, it’s worth it for the amount of trust built between members of different teams.
  • Genuine appreciation. Practicing genuine appreciation for the people who work for you and around you is incredibly important when working with remote team members or in an entirely remote company. What that means is instead of saying, “Wow, great work!” explicitly noting and addressing what you liked about the work. For example, you could say, “Wow, the amount of detail that you put into that bug report was great, and really let me dive deep to solve the problem much more quickly.” This gives specifics that allows the person receiving your praise to understand what about their performance should be repeated, and also feels better for them to hear than three words that could be tossed out about anything.
  • Scheduled cross-team chatter (Fika, Donut, etc). Similar to having a video chat or communal space where people can talk about their interests, many remote companies have some kind of regularly scheduled, randomly rotated meeting across teams. They go by many names, and now tools are even being built to automatically schedule them, like Donut. Having a randomly scheduled, non-work-related meeting with someone from another team simulates the natural communication that would come from being in an office. You get to know someone better and build rapport with them without having to go through the awkward first dance of reaching out to someone over chat. When it’s scheduled for you, both parties feel compelled to attend. This is important because it allows people to communicate and humanizes people on other teams. It creates compassion, for example, between engineering and support team members and lets remote employees get to know people that they wouldn’t otherwise get to know.
  • Team retreats. Team retreats are one of the best perks about working remotely. Once (or twice, if you’re Zapier ) a year the whole company (both remote and co-located, if they exist) travels to an offsite and does team building and in-person meetings for a few days. It sounds exorbitant but it is integral to maintaining and deepening bonds between people who don’t regularly get to see each other. Having people have fun together is one of the best ways to ultimately ensure that they are able to work together. In times of frustration and doubt, they can remember back on the time they completed a climbing wall with two of their colleagues or the awesome event where the whole company built dog houses to give to a local animal shelter. This is another one of those instances where, while it may cut into regular work, it’s worth it for the additional benefits in community, communication, and friendship later on.
  • Regular 1:1s. Even if someone is remote maintain a regular 1:1 schedule with them. Just like employees in the office, remote employees have schedules that they maintain and stick to. Having regular 1:1s gives employees and managers a cadence to track how their performance and feelings about the job shift. It also gives employees a safe space where they can expect to be able to go and talk about things that are bothering them or how they are feeling. When a manager shifts or cancels a 1:1 right before the meeting, it sends a signal to the employee that they don’t care or value the employee’s time. So, schedule something regularly that the manager is able to stick to, and do not cancel or shift it unless you really have to.

So, with all those meetings being so awesome for support, how do you do them?


Meetings in a remote team

M eetings in a remote team can be hard: it’s difficult to find the time when everyone’s schedules are all different, and it can be hard for everyone to make their technology work and to be able to talk to each other as expected. That being said, there are many tried and tested methods to optimize your remote meetings and ensure they are the most productive that they can be.

Meetings in a remote team

We’ve selected a few of the best insights around meeting each other remotely, and provided them below.

Consider the goals that you are trying to achieve

Many companies fall into the hole of having meetings just for the sake of having meetings. But, that takes up a lot of people’s time, sucks a lot of energy out of employees, and takes money directly out of the coffers of the company. While recurring, regular meetings do serve to provide a useful cadence for the people that attend them, it defeats the purpose if you have nothing to talk about and address.

A great way to think about this, then, is to figure out what you are trying to accomplish, and how frequently you’ll need to meet to discuss it in order for it to be a success. For many projects, this will not be weekly but could be biweekly or even monthly with short work chat check-ins as each member of the team works towards the goal. If you think about what you want the end goal of all of the meetings to do be, it should help you determine both the frequency and length of the meeting itself. This will save you the effort of going about a month or so in and realizing that you did not need to be having meetings so frequently, and have actually wasted quite a bit of each other’s time.

Create a reliable structure and stick to it

Once you’ve determined the frequency and cadence to your meetings, stick with it. There is nothing worse than being a remote employee and shifting your schedule only to have the meeting be canceled at the last minute. It’s important for everyone to respect each other’s time: once you’ve scheduled something to try to stick to it and avoid rescheduling. If you do have to reschedule, do so fairly far in advance so that other people that are joining in on the meeting know about the shift before they hop on to join and end up not having to be there.

Create an outline

Whether you are creating a culture with a lot of scheduled, regular meetings as a part of your framework or you only have a few meetings sprinkled here and there, it’s important to create an outline for the meetings you conduct. There’s a great example in this post from Groove. Their doc elucidates all of the time-frames for everything that they are going to talk about, as well who says it, and the cadence at which it occurs. That sets both the speakers and the attendees up for success by ensuring that they have a timeline to follow during the meeting and that the meeting won’t go over.

Consider doing an asynchronous video update

If it’s possible to not have a meeting, that is always going to be preferable. The people over at Help Scout did a really interesting thing where they created a weekly video update, instead of holding a company-wide meeting and sent it around for people to view asynchronously. The benefits of this are many. First, people can watch it on their own time, and maybe be more focused on the content than they would have been if the meeting was at a time that was difficult for them, or didn’t fit into their schedule. Second: people can rewatch the content through the week to refresh if they need a reference for the metrics or something else discussed. Third, the video is likely going to be much shorter than a meeting would be, so it frees up all the time of all the people that would have been in the meeting to do other things. Depending on the size of your company, that could be huge. Think about how much time that is!

All of our meetings at Chatra happen in Slack. Our developers and founders make group calls several times a week to discuss current and upcoming tasks. Once or twice per month we hold an all hands meeting where we share news and updates, listen to the customer feedback collected by the support team and come up with ideas on what to do next to make Chatra even better. This cadence means that everyone on the team is focussed on what needs to happen next — and exactly what our customers need to be successful. Learn more about how we’ve built the best messaging tool for your website — whether your team is remote or not!

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Have fun

Have at least one meeting that is just meant for fun. Whether that be an hour-long optional session each week for people to just socialize, or scheduled randomized donuts like mentioned in the previous section — allowing your remote team to have fun together, even when not on an offsite, is super important. Create something in your meeting structure for that, otherwise, you miss out on an opportunity to better cultivate an amazing and inspiring remote culture.


How to measure the productivity
of remote workers

So, it’s all well and good to talk about creating an amazing culture and hiring amazing people, but how do you measure whether it’s all working or not? Luckily, there are a few ways that have been tested and used by some prominent remote-culture companies that you can borrow from:

Set clear company goals

While it doesn’t necessarily sound like something that would affect employee productivity directly, setting and maintaining clear company goals gives employees a waving banner that they can rally behind. Public, company-wide tools like PivotalTracker and BaseCamp are useful for all employees to see progress and how it is being tracked, which adds additional incentive to get work done and in on time.

Create personal plans

Why wait for someone’s performance to drop to create a personalized plan for their success? Companies like Five Q create personal plans for each employee so they can know how they are stacking up against expectations. While personal plans may seem daunting to employees, they actually just give them what they deserve, and should have anyway: clear expectations and clear guidance on how to get there.

Analyze important tasks

Having something numerical to track can be really easy. Tools like 15Five make it easy to see exactly what your team has accomplished and in what kind of timing. This allows you to analyze the goals that your team is working towards as well as see how long it’s taking them to get there. Having a better understanding of the landscape associated with your goals and their pathing can help you better plan your employees’ time usage for the coming weeks. For example, if you know that a specific task related to operational planning took a really long time to complete, and you have another one coming up in the near future, you might want to switch it out for a quick win in order to keep your employee motivated.

Maintain a results-oriented culture

Create accountability by holding people responsible for work. As you set your company goals, encourage smaller teams and departments to make their own goals that nest within them. This gives them something closer to their actual day-to-day work that is measurable in the same way as company goals. Because their team/department goals will run up to the company ones, the impact they create on the smaller goals will also be reflected in the larger, more “important” numbers that are shown for the whole company. Seeing your day-to-day work impact the whole company is incredibly meaningful and motivating to continue performing excellently.

Have employees track hours and activities

Some companies like to have their employees monitor hours worked as well as describing what they do with each hour. While that’s not necessarily scalable for all companies, for some that offer services like personal assistant work or writing, it can be important to track what freelance employees are doing and billing for pretty intently. That being said, tracking hours and activities closely, if it’s unnecessary for your industry, can kill the productivity of your workers, according to Entrepreneur. So, evaluate what your needs are before putting this practice into place.

Use an annual review process

An annual review process is as much an opportunity for the employee to tell you how they’re feeling about the company and where it can improve, as for you (or the manager) to tell the employee how they’re doing and how they can improve. Having this kind of exchange can reinvigorate the employee and get them fired up if their enthusiasm for the company was starting to wane. It also gives them the incentive to keep working: if they know that someone is going to be reviewing their work at an annual review, or is perpetually reviewing it leading up to a review, it makes them want to work harder to get the extra bonus, raise, or any other incentive you attach to working for a year for your company.


Mostly, you should work on hiring employees that you trust. Much of this book has talked about how to find the right types of people to fit into your company. Once you find them, you should trust that they are trying to do the best by you and your mutually aligned goals. If you are constantly wondering if they are doing their work, they’ll likely become demotivated by micromanagement and leave. Of course, pay attention to the work output that you are seeing, and if they are sticking to their goals, but beyond the normal types of accountability that you would have in-place for in-office employees, you should assume positive intent with your remote employees and trust that they are doing the work they need when they need to.


How to maintain work/life balance

As we’ve mentioned a few times, it can be difficult, even if you’re an outstanding, over-performing amazing employee, to maintain work/life balance. That kind of balance is incredibly important for people, especially within the context of working remotely, because it helps to prevent burnout and keep people enthusiastic about their job.

How to maintain work/life balance

But, for many, finding balance is elusive. It’s hard to maintain separation when the place that you work every day is also your home. So, how can you be better at it?

  • Try starting your day as if you were going to the office. Leon from the Balsamiq team gets dressed every day, leaves his house, walks around his block twice, and then starts his workday. When he’s done he gets up, leaves his house, walks the opposite way around his block, and comes back inside. While that’s a bit extreme, there are other ways to “start your day, ” even just by doing something like getting dressed in attire you’d wear to your job.
  • Think of it as work/life integration. For many, the idea of “balance” seems unattainable so focusing on the integration is important. For example, many remote employees have children and need to take long breaks throughout the day to go and pick them up or drop them off from school. What this means is that the day is broken into around four-hour chunks of working and personal life — it’s integrated and mixed together, rather than balanced.
  • Put down the work chat on the weekends. If you can, do not look at or respond to work chat or emails on the weekends or any time you are on vacation. It can be hard and stressful to not monitor what’s happening, especially if you are in a higher-up position in the organization, but trust that your other teammates are capable of handling it, or would find another way to reach out to you if they weren’t. Vacation actually boosts productivity, according to Psychology Today, so don’t waste it!
  • Meetup with other remote friends. It can be nice to cultivate a group of remote friends and meet up every once in a while to co-work at a coffee shop or someplace similar. This can help remote employees feel slightly more connected like they were co-located employees going out for drinks with colleagues. It’s also a good way to talk about some of the things that remote employees face with other people who “get it.”
  • Find your routine. People who work in an office have a regular routine: they get up at the same time, commute to wherever they are going, probably get lunch at the same time, and commute back at the same time. Because remote work is very flexible, most remote employees don’t start off with that same level of scheduling. Set your routine up for yourself and stick with it. Then, your brain will start to associate certain times with work, and certain times with not-work to help you psychologically adapt from work/life balance.
  • Don’t sign on the minute that you wake up. Many of us sleep with our phones right next to our beds. When you pick it up, don’t let work be the first thing that you look at. Wait a little bit of time before you start to see what’s going on in your company’s chat, or who has emailed you. Allow your brain to switch on and greet the day properly before moving automatically into working.
  • Create a workspace. Create a place for yourself to work and allow that to be the only place that you work. Similarly, don’t do anything in that space beside work. It’s important to have a dedicated space for work, especially with your home technically being your office. Try to have the space be outside of your bedroom or where you generally do things for pleasure (like play video games, knit, or anything else). If you have a separate room you can use, that’s excellent, but otherwise, try to use a space in a less-often-used room to give yourself a little bit of a mental barrier.

Tools to use

T here are so many tools available now in the digital landscape that make remote working amazing. Everything from video chat to collaboration tools makes it so that remote employees can connect with each other and get their work done productively. So, what are some of the best tools out there for such things?


Slack is an outstanding tool for company chat and allows people to have multiple different organizations in it. We, at Chatra, have different channels for different purposes, for example, there is a #random channel for sharing watercooler-type conversation, as we mentioned above. Our #urgent-from-chat channel is for questions that require help from other team members outside of our support team, like asking our developers to look into an issue or help with a more complicated technical question.

Slack also doubles as voice and video chat. We use Slack for our stand-ups and meetings between teams. We also have a team video call when a new person joins our team so they can introduce themselves to us, as we are all remote. During those calls, our founder introduces each team member one by one and says what they do for the company as well as some tidbits like what city they live in and what their hobbies are.


Trello is a useful kanban tool that many companies use to track feature requests, the development processes, and some personal tasks. They are also highly remote, and so offer a lot of great features for other remote teams to use. For example, you can check out their Inspiration Boards for examples of ways to use them for things like onboarding a new employee, creating a way to track OKRs, establishing an ongoing 1:1 meeting agenda, or tracking bugs.

Just like Slack, Trello can be used for dual work/life balance, which can be important for remote employees. You can create separate teams within Trello to separate out work boards from private, personal boards or you can share your personal boards with your teammates for things like recipe shares, or home improvement plans that you’re looking for advice on.


At Chatra we use Asana for billing-related tasks. It allows us to keep better track of things like refunds and invoices but also allows us to send individual reminders to ourselves. For example, we might use Asana to remind an individual employee to send a custom invoice to a specific customer every 6 months.

Google Docs

Google Docs is a great way to share schedules, drafts for newsletters and onboarding emails, and anything else that requires you to create and share a document. It can be used for both personal and professional means just by switching between Google accounts (which are used for Gmail). It’s also associated with Google Forms, which can be a useful way to take surveys or send questionnaires to customers to see how they are doing, or to do internal training or surveying.


Appear.in is a lightweight web platform that allows you to video chat by just sending a URL. Unlike other video chat software which requires a lengthy installation process to your desktop, Appear.in allows you to just send a link to any participant and allow them to join. This is an excellent tool for conversations on the fly, or if you have to meet with a customer quickly.


Zoom is another excellent software for video chat and allows you to have up to 100 participants in a call — so, it’s great for those big company meetings. It does need to be installed on a desktop or mobile phone to work, so if you have a lot of people joining a meeting, it’s important to let them know beforehand so that they can prepare and have everything installed that they need to.


As we mentioned in the productivity section, some companies choose to have their employees track their time in hours with a detailed description of what they did. Harvest makes this easy by having a Chrome Extension (that integrates with Trello!) to make logging hours and entering details about them super easy.



So, now you know most of what you can know about working remote and building a remote culture. You’re prepared to attract and interview remote candidates, know how to keep them satisfied by building an excellent culture, and have fully versed yourself on how to make meetings great for them. Despite all your best intentions, though, remote won’t work for everyone. It can get lonely and tiring to be by yourself all the time, and for some people’s personalities, it’s just not a good fit. Recognize that despite you doing as much as you can and being a total boss of remote and off-site working, there are some people who you will not be able to champion. That’s okay! Remote work is not for everyone. But, for the few that you lose, you’ll keep many and this guide will help.

  • Mercer Smith-Looper. A writer, public speaker and support veteran of over 15 years, passionate about providing support teams space and insight that they need to do what they do best: help the customer. She currently is the Director of Support at Appcues, but in the past has worked in leadership for Wistia, Campaign Monitor, Trello, and Atlassian. Beyond that, she has consulted and written for some of the most prolific customer support companies world over.
  • Sarah Chambers. Editor-in-Chief for Chatra and a prolific author focusing on customer loyalty, success and remote work. A former support executive herself, she currently runs Supported Content, a boutique marketing agency for customer service businesses. When she’s not furiously typing away, she’s climbing, knitting or snowboarding in the mountains of Western Canada.
  • Yaakov Karda. Co-founder of Chatra and a customer support enthusiast. He’s authored and co-authored dozens of blog posts and a number of books on the subject. His writing has been featured in top industry publications and his books are available on Amazon.
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