Are you ready for the permanent, remote-friendly workplace? While many thought the pandemic brought only a temporary shift to remote work, the data tells a different story now:
According to a Gallup, only two in 10 companies appear to be fully on-site and only 6% of remote-capable workers even want to be working fully on-site going forward.
The chart paints a stark picture that shows that we're heading for a hybrid workplace future; while the number of fully remote organizations has dropped rapidly from the May 2020 peak, rather than a similar rise and recovery of fully in office teams, we can see that hybrid organizations are now the majority.
These numbers starkly tell us that, despite some leader’s wishes, remote work isn’t going anywhere. That means we all need to be prepared and embrace the changes and challenges of remote teams.
Managing remote teams: A trend with no end in sight.
It's no surprise then that AngelList Founder Naval Ravikant said of remote work:
"It is probably going to be the single most important new category in hiring...We're going to see an era of everyone employing remote tech workers, and it's not too far away. In fact, now's the time to prepare for it.”
It’s even more amazing, because he said it in 2019, before COVID came along.
And that’s for good reason. A pre-pandemic study from Stanford found that companies that offered remote work options reduced job attrition by 50%.
Meanwhile, an MIT Sloan School of Management survey by Dr. Peter Hirst found that offering remote work options made employees happier, more engaged, and less likely to leave the company.
This alone would be a great trend to watch and expect to be a part of, but COVID came along and accelerated this even faster. We are already at only about 20% of employees being fully on-site.
With all this in mind, you're probably already managing a remote employee or two, and even if you aren't now, you likely will be in the next few years.
A warning to companies hiring remote workers: All that glitters is not gold...
Unfortunately, there's more to remote work than people not coming into the same office as you.
Hiring remote employees comes with unique challenges, both for managers leading those employees, and for the employees themselves. Buffer's annual State of Remote Report offers great insight into some of the challenges remote employees face. And you’ll notice these challenges are pretty consistent - remote work has consistent challenges with or without a pandemic.
Most managers aren't prepared for this, because they don't realize how different working remotely really is.
For example, the idea that most remote workers are digital nomads traveling around with their laptop, working on the beach, is totally false; as remote work evangelist and former CTO of Product Hunt, Andreas Klinger, remarked on Twitter:
Instead, most of the millions of remote workers work from home, a co-working space, or share a full-time office. They also don't travel more than the average employee.
So, are you ready to hire remote workers and manage them well?
If you plan on hiring remote employees, or you have already, this post is for you. Many of us fell into remote management with the pandemic, and you or your company decided to continue with a remote or hybrid setup by default.
On that path, it’s not long before you may start hiring remote staff, which has quite a few challenges you may not have planned for.
That’s why below we've broken down everything you need to know about hiring remote employees that you might not have seen coming, so you can avoid very costly mistakes and better manage those remote team members.
We'll cover a variety of common issues and pitfalls to avoid when hiring a remote team, and what to do about them, including:
Table of contents - Common challenges you need to be ready for
- Managing time zones for your remote employees
- Understanding intention from remote communication
- Empathizing with different cultural communication styles
- Making more time for your remote one on ones
- Whiteboarding and ideating without being in the same conference room
- Spending more time managing and documenting processes
- Planning and budgeting for regular face-to-face time with remote employees
- Praise and celebrations are harder, and often unequal, for remote team members
- Your remote employees may experience severe loneliness
- Unplanned, costly taxes, regulations, and other legal paperwork
- Not everyone is a fit for remote, even if they say they are
- All remote or none remote is much easier than some remote
- Onboarding is different, and even more important
- Unexpected surprises that only remote employees can pull off
- Additional resources/Further reading to continue your learning
So, let's jump in.
14 Challenges You didn't Plan for When You Started Hiring Remote Employees (and what to do about them)
The Lighthouse team is remote, and we've been speaking with various remote leaders over the past few years, collecting both public and private stories about the challenges specific to having remote employees.
Consider these guard rails to help you avoid making the same mistakes other leaders have made. Some will boost morale and productivity, while others can even save you thousands of dollars by avoiding unexpected taxes and fines!
1) Managing time zones for your remote employees
Dealing with different time zones is one of the first challenges you encounter when working with remote team members.
Small differences, like the 3 hours that separate California and New York, aren't often that big of a deal. However, crossing oceans changes that in a big way.
For example, the US West Coast (PDT) to Israel is a 10 hour time difference (and the latter don't work Fridays).
If you're in Silicon Valley and you're messaging a team member in Israel first thing in your morning, they're likely already out of the office for the day. And they won't be in yet by the end of your day, either.
With a schedule like that, at times you'll lose an entire day of work waiting for an answer or to have a conversation, simply due to time zone differences.
This might work out fine for most emails and some messages, but it makes it nearly impossible for scheduling group meetings. Less overlap in time zones also means when they need to talk to someone live, that person may not be available.
The tyranny of the main company time zone
These difficulties can create an uneven power dynamic for long distance remote staff. If a remote employee is many time zones away from most of your team, they can face a number of challenges:
- To make a generally accepted meeting time, they may have to get up very early, stay up very late, or miss things like typical family time.
- Remote workers may be excluded from meetings with excuses used like, "we needed to make a decision quickly" or "their window of meeting times is already full."
- They may completely shift the hours they work, causing them to sleep significantly differently than spouses, friends, and neighbors.
How to manage difficult time zones
To combat this, Doist founder Amir Salihefendić has several great tips for establishing a more asynchronous team culture, which he tweeted out:
5/ 🛑 Teach people how to spend time productivity while waiting for an answer. Blocks aren't a huge problem, as there is always something else to do.
— Amir Salihefendić (@amix3k) April 18, 2019
8/ 📄 Document things and make transparency a core value. For example, everyone in .@Doist can read all of the core discussions (regardless of which team it is, this includes leadership discussions). With transparency, people don't miss important conversations or decisions.
— Amir Salihefendić (@amix3k) April 18, 2019
In addition to those more fundamental changes to support asynchronous work, apps like Happy Tools, from our friends and Lighthouse customer, Automattic, help you easily schedule team meetings across time zones:
It's up to you whether the person you're hiring is worth dealing with these kinds of major time zone differences. However, it's good to know there are ways to make it easier to manage these differences.
As you dip your toe into hiring your first remote employees, it can help quite a bit if you focus only on candidates within a few times zones of your core team. By avoiding this time zone challenge at first, you can focus on perfecting some of the other challenges we cover in this post before expanding around the world.
2) Understanding intention from remote communication
According to the philosophical concept Hanlon's razor, coined by author Robert J. Hanlon, we should "assume ignorance before malice,” when communicating with others.
We can often give people the benefit of the doubt based on a variety of non-verbal cues and clues like a smile, the inflection of their voice, or their general posture.
We have eons of programming within us, way back from our early days of survival, designed to pick up on many of these non-verbal signs– signs you can't pick up on if you can't see someone face-to-face.
As a result, when we communicate online, through Slack, email, or comments in a project management tool, it's all too easy to assume the worst of our team members from a negative sounding message.
Our mind is executing an automatic defense program that never before had to draw conclusions with such limited information. When this happens, everyone on your team suffers.
Assume positive intent
Instead, make it a habit to assume positive intent especially when messaging with your remote employees:
There's a lot of data to back all of this up. One study published in the Journal of Consulting Psychology discovered that 55 percent of communication is visual. That means when you're messaging remote team members online, you're missing out on 45 percent of what they're saying.
Another Cornell study echoed this, finding participants performed better when they could observe their instructor’s hands, eyes, gaze, and facial movements. Researchers from Cornell and University of Waterloo also found in a different study that in-person requests are 34 times more effective than email requests.
This adds up to an obvious, and important solution...
How to improve remote communication: Have regular video calls
You can't and shouldn't stop messaging remote team members. However, one thing you can do to help this problem is to have regular video calls. Anyone managing remote employees for a long time will tell you that's remote management 101.
Tools like Zoom and Google Hangouts make this easier than ever. The ongoing improvement in video conferencing technology means that the frustrating bugs of recent years are thankfully becoming less and less common.
It's also reasonable to expect your remote employees to work somewhere they can have high bandwidth internet, so that connectivity is never a barrier to communication. You can test for this during the interview process, by seeing how easy it is to have quality video calls with them during the interview process.
Try to make everyone on one a video call, and when you need a lot of active participation in group meetings. Doing so will give you back much of the previously lost non-verbal communication: their voice, their tone, their body language.
It also creates opportunities to build more rapport with them and for everyone to get to know each other more, like when I saw a coworker wearing a Mark Price jersey and later surprised him with a related gift.
Like with most things, moderation is key. Don’t go overboard with meetings. To avoid Zoom fatigue, embrace things like asynchronous communication where it makes sense, and keep the meetings for times you need to decide or discuss something in real time.
Other ways to overcome or even prevent Zoom fatigue include avoiding multitasking, setting an agenda and sticking to it, only asking for video calls when necessary (i.e. for one on ones and group meetings that require a lot of participation) and allowing your team members to switch off their cameras on other calls.
3) Empathizing with different cultural communication styles
Beyond understanding a coworker's intent, sometimes communication barriers can occur when your remote employee is from a different culture. What one person thinks is normal and acceptable can feel odd, offensive, or foreign to another person.
Even within the U.S., there are different styles. For example, New Yorkers are known for being more brash and direct, while SoCal folks are often more indirect and laid back.
Can you tell when someone is being a jerk, or they're just being direct (sometimes they're the same thing)? There's a lot of nuance to understand if you haven't lived everywhere your remote employees have.
This video captures a slightly funny and extreme case of this, with a German and New Zealand couple discussing the different ways to discuss changing a dirty kitchen towel:
The point is that you may not even know when you're offending, or not getting through to someone, and the same is true for your remote employees.
The only way to know is to take the time to get to know your remote employees well, and to make sure there's a clear, open dialogue with them. You need to ask good questions from the start like Lara Hogan recommends on feedback:
- How do you like feedback? - the medium (IRC, email, in person, etc.)
- How do you like feedback? - routine like in 1:1s, or as-it-happens
- How do you prefer to receive recognition? (public or private)
Learning these things will help you start on a stronger foundation with them. Then, over time you can learn more about their culture, and share some of yours so that you both can better understand each other.
Culture and habits impact everything
Realize however, this goes beyond coaching and feedback. This can impact everything from how that remote team member asks for a promotion, brings up issues, and interacts with the rest of the team.
It's important to take some time to understand their cultural communication style and explain yours to them. That way, you're not unfairly comparing them up against your own cultural norms, and you can work together to bridge any divides or misunderstandings.
In the end, the responsibility is shared by you and everyone on your team to understand each other.
As you bring in more and more cultures around the world, lead by example and explicitly talk about how there may be times people will misunderstand each other.
By doing so, you'll help everyone give each other the benefit of the doubt, and avoid little things like tea towels becoming a bigger deal than they should be.
4) Making more time for your remote one on ones
Your remote team members can't stop by your office nor easily grab you in the middle of the day to ask a question or offer feedback on a project. They also can't attend the office happy hour to build rapport with you.
Plus, as we talked about earlier, it's easy to misunderstand intent when communicating online.
The best way to offset all three of these issues effectively is to invest more time in one on ones with your remote team members.
Longer one on ones help you have time to build rapport with your remote employees. That rapport goes a long way towards helping offset the challenges we've already covered today. Rapport makes communication healthier, obtaining and giving feedback easier, and it can even improve engagement.
According to Gallup's State of the American Manager report, employees whose managers take the time to build rapport are more engaged:
However, the only way to build that rapport with your remote employees, is to invest time to create it. When you're on a call, it can be really easy to stay formal and efficient, staying on task.
Resist that temptation and make some small talk. Ask how their family is, be curious about their holidays, and take an interest in getting to know them.
This all starts with your schedule. Set aside an hour for your 1 on 1s with them every week, and let there be some small talk in other meetings.
It may not seem like in the short term it has a strong ROI, but the foundation is priceless. It also makes work more fun and interesting as you get to know what makes different people tick.
One on ones are one of the best tools for any manager, and especially remote managers. They're also one of Valentina Thörner's favorite tools as we discussed a wide range of remote and hybrid team management tactics in our great interview with her on our podcast:
5) Whiteboarding and ideating without being in the same conference room
Sharing ideas between remote team members is naturally more difficult. That's mostly because you're missing that critical office element of a common space.
Remote employees have nowhere they can go to riff on an idea that just popped into their head. Similarly, remote employees miss all those unscheduled conversations (aka - "Collisions" as Steve Jobs called them) about tweaks to product, great ideas, or last-minute project changes.
If you have remote employees on your team, that central place where you can go must become digital. This also makes whiteboarding and ideating/brainstorming in general much more difficult.
Tools for whiteboarding and brainstorming with remote employees/teams
Often, remote teams will fly in to meet each other specifically for whiteboarding and deep, creative, project collaboration. This can make the whole process a huge pain, and lead to key discussions getting put off longer than they should.
Fortunately. there are a lot of tools that help make this process easier.
Head of Remote at AngelList, Andreas Klinger, asked his following what they use to whiteboard and brainstorm with their team remotely. These are some of the most commonly tweeted tools:
How do you do retros and idea brainstorming efficiently online?
Are there good online whiteboard tools you can recommend?
Are there better ways to do this?— Andreas Klinger 🏝 (@andreasklinger) May 13, 2019
Mural for general brainstorming:
We've used https://t.co/JHsHZWcgR1 for brainstorming and FunRetro for retrospectives.
Mural also has templates for retros, but I haven't used them.— :snowflakelbz: (@dossiette) May 13, 2019
Miro for whiteboarding:
Upwork runs on @MiroHQ (previously called Realtime board) all the way for anything related to whiteboard.
For many engineering meetings, we use Google docs + Hangouts.— Utkarsh Sengar (@utsengar) May 13, 2019
Parabol for retrospectives:
And some prefer to get creative, like this sailboat whiteboard:
Many also suggested Google docs instead of a whiteboard or brainstorming-specific tool because of the ease of functionality.
Ultimately, the best tool to use is the one you and your team like. Trying a few different ones can be tedious at first, but finding one that you all like can make a huge difference in the frequency and quality of your whiteboarding / ideating sessions.
This then improves the quality of the work you and your team delivers, and can improve the rate of innovation, as you remove a key bottleneck in your process (ie- waiting to fly someone in).
6) Spending more time managing and documenting processes
Setting up and managing processes within remote teams takes more work– and that includes partly remote teams, not just those fully remote.
Quick conversations in the office add up fast. Not only do questions get answered faster that way, but numerous company culture norms also get communicated by both what is spoken, and what people see others doing. Unfortunately, remote employees only see a small fraction of those things, so you need to compensate for that.
This extends to a variety of situations. If an unplanned conversation happens only with those in your office, your remote employees are both not involved in the discussion, and unaware of its outcome. They lose twice, and are now left feeling out of the loop.
To combat this, set up clear processes upfront that guide team members without slowing them down.
How to set up more intentional processes to support remote team members
In his "remote teams crash course”, Andreas Klinger writes:
"In remote teams, you need to set up in a way people can work as autonomously as they need. Autonomously doesn't mean "left alone” it means "be able to run alone” (when needed).
Think of people as "fast decision maker units” and team communication as "slow input/output”. Both are needed to function efficiently, but you want to avoid the slow part when it's not essential.”
He suggests asking several important questions to set up these autonomy-supporting processes by asking yourself:
"How can you…
… define strategy clear enough that people can formulate their own decisions without going off-track?
… set goals clear enough that people can benchmark themselves or their decisions?
… setup decisions hierarchies in a way that only non-reverse-able important decisions even bubble up to you?
… create confidence? (speed comes through confidence)
… set up your environment/processes that they can act even in emergencies on their own?
And also ask yourself...
- When is it enough that you hear about it and when do you need to be involved?
- How can you make sure that you are only involved in every 10th decision and only "manager-override” every 100th?
Similarly, DevOps platform Gitlab's remote work manifesto outlines several specific points to improve team processes. It states that, "All-remote work promotes:
- Writing down and recording knowledge over verbal explanations.
- Written down processes over on-the-job training.
- Public sharing of information over need-to-know access.
- Opening up every document for editing by anyone over top-down control of documents.
- Asynchronous communication over synchronous communication… ”
Each of these principles helps establish processes that are more conducive to remote work and ensure that remote team members never miss out on important information.
It's really about information dissemination
The biggest problem with partly remote teams or hybrid teams is the difficulty with making sure that information gets to everyone on the team promptly and effectively.
If you're used to having everyone in the office, it can seem jarring to have to deal with keeping a remote team member in the loop. And that's in addition to making sure they have what they need to get their work done mostly asynchronously.
Documentation of everything is the key habit that needs to be adopted by everyone on your team. It's easy to forget that your remote team members weren't a part of that last-minute conversation as everyone was walking out of the office last week.
One way to remedy this is to write everything down and keep it in a central place. The GitLab handbook and Basecamp Handbook are great examples of ways that many remote-first companies are doing this.
These types of handbooks serve as a first point of contact for any issues and help to keep remote employees up to speed in a systematic way. They can be edited quickly and easily by anyone using platforms like GitHub and GitLab and can be managed on multiple branches and with multiple collaborators.
By building processes like this that make sure everything is documented in a systematic way, you ensure your remote team members (and really, everyone no matter where they are) are easily kept in the loop.
They also then have places to contribute as they can review any newly documented items and add their thoughts, feedback, and suggestions, just like they would have had they been in the original meeting.
Don't feel like you have to be perfect. Any documentation is better than none for someone who otherwise would have nothing to look at.
Once you have some documentation, you can start to iterate to the format (video, audio, docs, etc) and information that fits your team and each situation best.
7) Planning and budgeting for regular face-to-face time with remote employees
The idea of hiring remote employees can be seductive: managing an employee whom you simply check in with periodically, gets their work done on their own, and generally saves you on salaries by being able to hire outside costly areas like Silicon Valley.
The problem is, nothing beats the magic of face-to-face interaction for both creative work and bonding. Just because one of your employees is remote doesn't mean you never have to meet in person.
Ideally, you should be flying remote employees in regularly, as much as every quarter depending on need and preference. So, while you may be saving on salaries, you should be using some of that savings on flying people out to meet with the rest of the team.
Consider company retreats for remote team bonding
Company retreats can be pricey, but they can offer a great return on investment. As