Remote Work Advice : 16 Expert Tips For Leaders To Succeed at Remote Work in 2023

Remote Work Advice : 16 Expert Tips For Leaders To Succeed at Remote Work in 2023

If 2020 felt like remote work 101 for many companies, 2021 was the university lecture where people either passed, failed, or dropped out.

Companies were put to the test of postponing office re-openings, experimenting with hybrid work, or switching to remote-first 

If we were to rank the companies for sheer revenue growth this year, it probably wouldn't be the ones with a return to office mandate. 

The course is challenging, though.

Even as a fully distributed company, we struggled this year to avoid burnout and meet deadlines while working asynchronously.

That is why in our newsletter,The Remote Times, we interview remote work experts to find out how to address these issues and get to the next level of distributed work.

We have compiled some of their greatest lessons into this article to help others navigate the uncharted waters of remote work in 2022. We will cover the struggles currently affecting remote workers, building a remote culture, mastering remote processes, analyzing hybrid work, hiring a Head of Remote, and predictions for the future.

Remote Workers

Remote worker

Being a remote worker has its ups and downs. Yes, you can potentially work from anywhere with an internet connection, but can you still be productive without sacrificing time from your personal life?

The truth is, remote work is not for everyone. It takes a level of responsibility and self-awareness that isn't required for many in-person roles.

Not to mention, if you have zero experience, it is a difficult working arrangement to break into.

To reach work-life balance nirvana, you need a structured routine and stay dedicated to it. You need to be empathetic with your colleagues while potentially never meeting in person. 

We asked Jordan Carroll, aka The Remote Job Coach; Ali Pruitt, Remote Productivity Coach; and Maaria Tiensivu, Remote Design Manager at obodo, about continuously improving as a remote worker.

We also heard from Tyler Sellhorn about his keys to success as a remote worker and John Lee, Cofounder of the Work From Anywhere Team, about tax issues to consider before moving to work abroad.

Q: In your experience, what are the top 3 skills workers need to join a remote team? 

jordan caroll

Jordan Carroll, remote worker with 8 years of experience, Founder of The Remote Job Coach

  • Communication, especially asynchronous. If your emails have spelling and grammar mistakes or miss out on context and nuance of written communication, you’ll have a short leash with a recruiter or a remote team. Working on your writing will go a long way in life.
  • Persistence. Recruiters and hiring managers are busy with so much. Your ability to be a “polite pest” and show them you really want the job will be instrumental in considering you. However, there are some boundaries to consider, which leads to my next one...Emotional Intelligence.
  • Being empathetic and emotionally intelligent with others is so hard to teach. When you can understand social and group dynamics and be emotionally stable and smart, people will want to be around you and work with you.

Q: How can you be ruthless with your task prioritization at work but also thoughtful with your time management in your personal life? 

ali pruit

Ali Pruitt, Remote Productivity Coach, Founder of Fully Remote with Ali


First, make your personal life your #1 priority and schedule time on your calendar for it. Then, make strategic planning a weekly focus. You need clarity and direction to make progress.

Break down the tasks and then blueprint your days/weeks using time-blocking and time-boxing methods. Use a timer. Feeling a sense of pressure with time-boxing can help you stay focused. 

End every day with reflection and evaluation to better adjust the coming days.


Maaria Tiensivu, Remote Design Manager at obodo, Founder of Innovation Distributed


You should create clear priorities and realistic task lists. If you cant finish your to-do list most days, you’re trying to fit in too much. I usually tell my clients only to include 3-5 tasks on their daily to-do list.

Any additional responsibilities that appear should be taken to the master to-do list, where the daily tasks are.

The mental and emotional drain of having too many things on your plate makes it harder for you to focus when working, and it lingers in the unconscious when you’re off. 

Make sure you know when you’re done for the day. Whether it’s when your list is done, you hit a specific time of day, or you put away your work computer.

Q: As someone involved in multiple remote work endeavors, how do you keep track of everything/manage your time?

Tyler Sellhorn

Tyler Sellhorn, Head of Customer Experience at Yac, Host of The Remote Show


Okay, so for me, one of the things that remote work is enabling is fitting remote work and my productivity around my life instead of the other way around.

Because Yac is an asynchronous company and in distributed work, employees are located across many time zones, it's not really possible to spend much time together.

It's almost impossible to have a continuous video conference or that sort of thing. So with these gaps in time, the big thing that I've done is block hours off the day for deep work.

I've blocked my time off for exercise. I've blocked my time off to cook breakfast for my family and pick up my children from school.

I'm also a youth sports coach. These are things on my calendar that are not time for calls. 

Yac is enabling more remote teams to say, 'okay, what should dominate your calendar?'

It's always going to be the things that will move the needle for you personally and professionally.

Looking at someone's face in a video call isn't going to be productive in the end.

The software that I swear by is blocking your calendar with important things to you instead of calls. 

Then, being consistent and showing up every day is a superpower.

Q: What are the critical tax steps you should take before moving abroad to another country?

john lee

John Lee, Cofounder of the Work From Anywhere Team


Step 1: Don’t just do a solo run at this. Talk to your employer, talk to your local accountant let people know about your plans before you make the move. 

Don’t wait until you have already spent 10 months abroad and you are in an accident or have to come clean to your employer.

You should also consider your salary. If you are making three figures, it should be a priority to get your tax situation figured out, and it is worth the investment in advice.

However, if you are closer to a middle-income wage, the taxes you will have to pay still may not take too much of a dent in your earnings. 

Step 2: Try to show your employer other WFA policies as an example of what is possible. You don’t have to reinvent the wheel, and your employer doesn't have to spend a ton to implement them. Just look at Bluegrounds.

Their employees can choose to work from anywhere or do an international transfer. You can even do short or long-term assignments, so you don’t have to transfer over the payroll to another country.  

Also, educate your employer about using a service like Deel or Remote Teams that act as an employer of record. You can be put on their payroll as an intermediary and can coast for 3-4 years without any worries.

Still, don't get too overconfident as the tax rules vary between country and you also have to be on the lookout for double tax risk.

Building a Remote Culture

remote culture

One of the biggest realizations this year was that you do not need fancy kombucha bars, gym memberships, or weekly happy hours to maintain your company culture. 

The number one thing that employees value now is the flexibility to live their best lives. When building a remote culture or making the transition, the question shouldn't be how do we substitute the perks or interactions of the office?

It should be: how do we ensure our employees are at their happiest and believe in the company mission?

Companies achieve this by letting their workforce spend more time with their families through paid leave policies or 4-day workweeks. They don't force fun and give employees the tools and space to create their own events or interact with their colleagues.

They hire people based on matching values and create serendipitous innovation with virtual water coolers. 

We learned about the fundamentals of building a remote culture and adopting a remote-first mindset through conversations with Rowena Hennigan, Founder of RoRemote; Sarah Hawley, CEO and Founder of Growmotely; and Gary Walker, Remote Specialist and Product Director at 22 North. 

Q: With increasing competition for remote talent, how can companies attract the most qualified professionals? What benefits should they offer? Is salary everything?

Sarah hawley

Sarah Hawley, Serial Entrepreneur, Author Of Conscious Leadership CEO, and Founder of Growmotely


Salary is definitely not everything! Especially when we consider millennials and what they’re looking for.

Being a part of something exciting that aligns with their values and passions, in a place where they’re empowered and trusted, tends to rank higher than salary (with many people even citing they’d take a pay cut for an opportunity that was more meaningful and where they were treated well)

Of course, paying a fair market rate is always important, but salary should not be considered the driving factor or the only thing a company needs to do to engage and get the most out of its teams.

I view money as just one of the energy exchanges between our company and our team.

Other forms of energy we exchange are trust and empowerment, freedom and flexibility, recognition and appreciation, contribution and exchange of ideas, professional development (to name a few).

If we as leaders can evolve our thinking to embrace all the different ways in which we can exchange energy with our team members and find the things that resonate the most with our unique culture, we’ll attract and retain ideal team members for us. 

We’re seeing at Growmotely, that companies hire within 2-3 weeks when they’re engaged in the process and on top of their recruitment pipeline. You can also use recruitment CRM to streamline the hiring process and manage separate pipelines for candidate progress and data. 

We have several steps in the process (pre-screen questions, video Q&A, reference check, and then, of course, online interview) that we’ve created based on our experience when it comes to remote hiring.

These steps aim to streamline the hiring process, so people move through each part based on their profile and the quality of their submissions.

It’s important to remember that while people are looking for work, you’re likely not the only opportunity they’re pursuing. Acting quickly to progress and decline applicants will get the best results when filling open roles.

Q: What are the most common challenges your clients experience with the transition to remote working? Where do they often struggle the most?

gary walker

Gary Walker, Remote Specialist and Product Director at 22 North


They struggle with the behavioral or cultural change to a remote-first mindset.

Remote-first is a mindset whereby you assume that everyone is remote, even if some occasionally work from offices.

The benefit of having a remote-first mindset is that it helps to ensure a consistent employee experience; regardless of where people choose to work, they have the same access. It's key to remember work is not a place.

In terms of struggles people have encountered - Over the past 18 months, we have witnessed organizations that had not worked remotely for a sustained period before the pandemic, trying to map the way they work in the office virtually.

This is unsustainable, and it has resulted in the following trends:

Replicating the physical office, virtually, has resulted in meeting fatigue.

People are substituting the time saved from not having to commute to work longer, whereas, in a remote setting, the time would be encouraged to be used differently to help improve wellbeing, productivity, and focus.

The current economic climate has also created nervousness about job security, the by-product being many people are overworking as they feel they need to show value to safeguard their jobs. 

This gives employers a falsely high productivity indicator, with many beaming of the productivity gains. 

There are many components required to enable the transition, particularly the review or creation of policies, digital infrastructure, handbook, hiring/onboarding, etc. 

But ultimately, this will live or die by your culture and behaviors.

By driving the change from a top-down and bottom-up approach, you ultimately convert the middle layer, often the biggest obstacle to change.

Q: What is the proper interaction cadence for a remote team or distributed team just starting out?

rowena hennigan

Rowena Hennigan, Founder of RoRemote


As remote work teams expand, work priorities change, maybe locations of workers and time zone change. The issue of meeting cadence is essential but also should be underpinned by the same fundamental principles:

  • A policy or statement should exist on meetings, the norms, frequency, etc., to establish a reference framework. Sometimes these include a criteria list to be checked under the terms ‘Do we really need a meeting’ - to ensure meetings called are valid and needed
  • There should be period’s (days) without meetings to enable deep work
  • Individual workers should contribute and control their calendar, adjusting and reacting to meetings requests.
  • Meeting etiquette and norms should be clear, i.e., only with a plan, roles will be evident during meetings, i.e., who is the note-taker.
  • Important meetings like 1-1’s should also have video on and should have a regular rhythm.
  • Performance reviews are also scheduled and respected. This is the chance for the team or individual to say, “we have too many meetings!” and have it adjusted. 

Turning company values into reality (by the everyday things that individuals and leads do) are the secrets to ensure everyone feels included, heard, and involved.

Simply being aware and stating silos may happen is the beginning of creating an open dialogue in an organization.

This has been an extra challenge during the pandemic, as local restrictions have reduced individual mobility and placed additional stress on workers.

Many remote-first organizations have bolstered their initiatives with extra days off (#restethic by GitLab campaign), organized different online events and support where possible, and encouraged small in-person meetings with local team-mates (providing food vouchers too!).

Human Connection is so important, and if an organization can influence that, in these exceptional times, they should.

Remote Processes

remote processes

Here is the hardest part of becoming an expert in remote work, creating repeatable digital processes that make your company's operations more productive. 

The first place to start improving your remote processes is documentation. It is probably the least favorite part of remote for many people, but having a knowledge base where anyone in the organization can answer their questions without asking another team member is crucial.

This doesn't happen overnight. It takes time to write everything down, optimize inefficiencies, and coordinate through everyone's daily tasks. But once you put in the time, just having a company handbook for decision-making is a game-changer.

We spoke to Katie Scheuer, Head of LX at Workplaceless; Nadia Harris, Remote Operations Manager at iTech Media; and Liam McIvor Martin, Co-founder of Time Doctor, to find their nuances in managing the operations at distributed companies. 

Q: For a company just starting to implement asynchronous practices into their teams what are the crucial first steps to get started?

katie scheuer

Katie Scheuer, Head of LX at Workplaceless

The Placeless Playbook outlines the first steps teams should take as they move toward an async-first hybrid or remote team, depending on role or function. 

Collectively, teams can also address decisions about async communication in a team Communication Charter Building Session, or begin to improve shared behaviors through bite-sized tips and advice. 

While many teams can establish positive async behaviors using a variety of tools, some of my favorites include:

  • MURAL, for visual collaboration via a virtual whiteboard
  • Slack, for sending quick messages to teammates
  • ClickUp, a powerful project management tool
  • Loom, a screen sharing and video messaging tool for async messages
  • HeyTaco, for async affirmations

Our team maximizes our sync time by using a blended meeting structure and ensures that our valuable sync time together is well-structured.

We use a Communication Charter to outline and align organizational norms around communication standards and practices. This helps us set expectations and boundaries while avoiding feelings of information overload.

Q: What are the logistics of organizing a large digital conference? 


Liam McIvor Martin, Founder of Running Remote, Co-founder of Time Doctor

Virtual events can be quite a bit faster than in-person events but generally, 90 days of promotion and another 30 days to plan the event out is the cadence we're on. With in-person, you're probably looking at triple that prep time.

We use Hopin for our virtual events. We also have a production company in the background. Before the event, we have talks with each speaker on Zoom to explain the type of attendee they will be speaking to at the event.

Proper production and having amazing speakers that are willing to engage with virtual attendees are the keys to a successful event. Ironically those rules also apply to in-person events.

The only responsibility you have as a conference organizer is: Do you have really good speakers and is the food good?

The attendee's behavior you can't control, but you can decide who attends by who you select to present.

Because at the end of the day, only 10% of a successful event are the talks themselves. The other 90% are the conversations that people have and the business relationships built from them.

Q: What does the recruitment process look like nowadays for hiring an international employee? What is your framework?

nadia harris

Nadia Harris, Founder of and Remote Operations Manager at iTech Media

  1. Identify the gap. What will this person do? What will be the goal of the hire to deliver? That is how we will be measuring if a hire is successful based on their initial outputs.
  2. Justify hiring someone remotely. Decide if there is a specific market that you want to target, look at multiple countries, and define the language requirements for the position. This is important because, for example, if you want to hire an SEO expert, their qualifications and language abilities will differ from country to country. You can then determine the talent pool and if it is broad or specific.
  3. Determine how much you are willing to pay. One place to look is Buffer’s pay scale. They have different pay brackets for different costs of livings. The strategy ensures that everyone on the team has an equal salary standard. But there are other companies that have a standard of pay regardless of where people are located, like Toptal. Or in the case of Facebook, where they will cut their San Francisco base-pay if someone relocates. Determine this before setting a price.
  4. Realize if you can even hire in a select country, but this has changed so much in the last year with employers of record like Deel or, or Oyster. You still may have to do some research if you have a subsidiary or headquarters in certain countries for tax reasons, but the problem has mostly been solved.
  5. Assess how competitive you are on that specific market and decide if the talent is rather easy to acquire or challenging. At this point, I will usually analyze the role and skillset and see how my client compares to other companies also searching for the same position. What is their competitive advantage and benchmarking against the other companies? I have seen some companies try to go global, but they have no advantage over even local hiring companies because they pay less, so obviously, no one will accept an offer from them. Try to know where you are.
  6. Automate the search. Not only using a local headhunter but also putting out ads in all the remote job portals and local job boards. This helps see the ROI of the search itself. Then in the screening process, you look at the CVs submitted and select people from there. Once you have a pool of candidates, they go through an initial interview for their skill set, a culture-fit interview with different team members, and I like to include a case-study portion. We give a task to check their technical skills and ask how they would react to a specific scenario relevant to company operations. So the person knows what potential might happen in the future, and so the company knows they have the right skills and mindset they are looking for.

Hybrid Work

co-working space

2021 was the year of the great hybrid work experiment. Companies thought they were getting the best of both worlds when they implemented mandatory 2-3 days in the office. What they experienced was the opposite.

A disjointed experience that left those working from home feeling left out and those coming to the office wondering why they were even there in the first place. It turns out hybrid work requires even more intentionality than remote work.

People should take zoom calls from their personal computers even if they are in the same room to create an equitable meeting experience for all. Even offices need to be redesigned to foster collaboration rather than isolating people at their desks.

We spoke to Paul Mckinlay, VP of communications at Cimpress and Vistaprint, and Lisette Sutherland, Director at Collaboration Superpowers, to determine how to maximize your hybrid work communication if you decide to pursue that route. 

We also spoke to Molood Ceccarelli, Founder, and CEO of Remote Forever™ to hear what she thinks about companies struggling with the hybrid work model and where companies are going wrong with remote work. 

Q: What are the dangers of miscommunication or unclear expectations about back-to-office plans on a remote team? How do you manage the different working preferences in your organization?

Paul Mckinlay

Paul Mckinlay, VP of communications at Cimpress and Vistaprint


A lack of vision creates an atmosphere of dysfunction.

You don’t have to know every answer right away, but it’s vital for leaders to convey a vision. This galvanizes the company toward a new goal.

Clarity on where work happens and how communication happens eases the pressure on office re-openings. Cimpress is viewing its newly-labeled Collaboration Centers in an entirely different light than we saw physical offices pre-pandemic.

We’re formally outlining the physical changes and providing guidelines on how we expect folks to use the spaces.

We’re also clear that someone’s physical location should not be an advantage nor a disadvantage.

This is critical to make explicit, as it empowers team members to choose the workplace and working style that best suits them without worry.

Left unsaid, team members may wonder if they’re missing out on information or executive exposure by remaining remote. Each week, we see that things we thought were good were actually bad/harmful and not worth holding onto.

Two examples are the water cooler and meeting rooms, which created suboptimal experiences for remote attendees.

We also declared early on that one’s location wouldn’t be an advantage nor a disadvantage, and unlike some firms who are forcing folks into the office a few days per week, we clarified that we wanted our team members to do their best work from wherever they wished.

Remote-first is less about where you work, and more about how the work is accomplished. We are not fixated on who is returning to a physical office.

Instead, we focus on questioning/auditing each tool, process, and workflow and pressure testing it: ‘Does this workflow work well in a remote or location-agnostic manner, and is it contributing to a great team member experience?’

Epiphanies are continual. Our team members are currently realizing new ways to enjoy flexibility, from attending midweek events with their children, having lunch with loved ones each day, and experimenting with non-linear workdays.

Q: What are your key principles and tactics for collaborating with hybrid teams?


Lisette Sutherland, Director at Collaboration Superpowers and remote worker with 17 years of experience


Modify how we communicate.

Almost everything concerning knowledge work has a workflow - and when we’re working in a hybrid way, it’s helpful for teams to define that workflow in order to minimize the number of messages and meetings.

Hybrid communication aims to replace the low-effort communication habits like sending emails or instant messages with high-quality touchpoints. We don’t want to prioritize being connected over being productive.

Good hybrid communication can include:

  • Work out loud and make what we are working on visible to others. Working out loud isn’t just for the sake of being social. It’s being social for the sake of getting the job done.
  • Make our availability clear to our colleagues to know when we are available and when we are not.
  • Master the communication tools we have. There is an app for almost everything out there. It’s crucial to find out what is available and follow your company guidelines.
  • Be clear and concise in our messages. Include resources people might need and use storytelling to reinforce the points you are trying to make.
  • Define normal behavior. When we work together in the same place, we can see what people are working on. Behavior is implicit. We tend to understand each other’s behavior because we can easily observe people and make inferences. In hybrid work, you have to define in-office and remote behavior. 
  • Understand each other's intrinsic motivations. Why do our colleagues come to work every day? What drives us to do what we do? Knowing what intrinsically motivates each other ensures that we see our colleagues as human beings.

What are some of the biggest mistakes you have seen in workplace initiatives recently when taking on new clients? What risks do businesses face if they adopt remote/hybrid work without the proper infrastructure?


Molood Ceccarelli, Remote Work Strategist, Agile Coach and Founder and CEO of Remote Forever™

First and foremost, allow me to clarify this subject: I believe - and have repeatedly written about this - there is no such thing as a hybrid team.

A team is either remote or in-person.

Anything in between implies that there are members that are remote, and this setup requires remote work infrastructure, operations, communication practices, and culture.

Unfortunately, several organizations have mistakenly adopted the term “hybrid” to avoid investing in this massive transformation that they are going through.

Hybrid is the term we use to talk about the physical whereabouts of employees. But work is what we do, not a place we go to.

Some of the worst workplace initiatives I’ve seen incorporate a sense of force and control onto workers.

Here are the top three worst practices I’ve seen:

  1. Installing spy software on employees’ computers to monitor various aspects of how they spend their time. → We need to trust people and stop measuring where someone is spending their time and instead measure what impact they make on the business.
  2. Mandatory attendance in the office to have team meetings. → More often than not, someone has to work from home or another city which means the entire team will have to host some meetings using a video conferencing tool. But this mandate stops companies from creating remote-first operations and leads teams to sit in conference rooms with poor audio and ignores the remote attendee.
  3. Not asking employees whether they want to work in an office or not and making decisions that impact their lives without their involvement. → Like any other major organizational change, a change that impacts the lifestyle or work practices of employees needs to be made together with them, especially in a pandemic of a virus that after almost two years, we still know so little about.

In essence, every initiative that focuses on the whereabouts of employees instead of their well-being, productivity, and the impact they make on the business is a bad workplace policy.

Remote work is about freedom to choose where you work from, freedom to create a balance between different life activities, space to nurture your relationships as you see fit (not as your employer's HR department sees fit).

The sooner you begin preparing for this shift, the higher chances of survival you have. In the long run, if you fail to adapt to this change soon, you risk going out of business.

Head of Remote

head of remote

One of the hottest new positions for 2021 was Head of Remote. But what exactly do these special people do?

Well, think of them like the glue that holds a distributed company together. They are just as important to employee experience as Ops management.

Heads of Remote lead a company’s transition to distributed work. 

They ensure every remote employee is engaged by fostering collaboration and organizing digital or in-person meetups. 

They are the owners of a company's documentation and help teach efficient remote working techniques. 

As more companies become better at remote working, there is speculation that there won't be a need for Heads of Remote. Everyone will be digitally literate enough to work remotely efficiently.

However, we think even if there isn't a Head of Remote at your organization, there should always be someone with the role to improve employees' remote experience constantly. 

We spoke to Rhys Black, Head of Remote at Oyster, and Chase Warrington, Head of Remote at Doist, to find out their day-to-day lives and their principles for guiding their teams. 

Q: What are the key pillars in your opinion to building a distributed infrastructure? What advice would you give to a company looking to hire a Head of Remote?

rhys black

Rhys Black, Head of Remote at Oyster


Manage by trust, not by control- Helicopter management isn’t possible in a distributed company (thankfully). If you can’t build a culture where your team genuinely likes you and wants to do good by you, it won’t work.

And if you feel like you can’t trust them to do a good job, then it’s not their fault. You made the wrong hire.

Asynchronous by default- This trope is becoming popular in remote work discussions. However, it’s usually only used in reference to company productivity. It’s as much if not more important from the point of view of the health and well-being of your team.

Everyone is a documentarian- Knowledge Management is the life-blood of a distributed company.

Not only do you need to build an operation where knowledge is sucked out of minds, put down on paper, centralized and structured so that it is accessible, you also need to build a culture where everyone references that documentation as their knee-jerk reaction and more importantly, understands the value of it.

Outputs > inputs- Knowledge worker output isn’t linear. It isn’t 1hr = 1 widget, so why care about the input? If the output is agreed by a set time, measure on that. Not whether it took them 1 hour or 100 hours. Be clear on what you’re actually optimizing for.

A Head of Remote in general is not a well-defined role yet and therefore could have almost an infinite scope.

So, make sure you’re ready to have your HoR hire at least 2 people underneath them to impact the company significantly.

Ensure they get the seniority they need to make an impact. Their role involves significant organizational change and therefore needs to influence all the way to the C-suite.

Ensure the person is able to balance cracking the whip with serving others. This role is fundamentally an enabler of others. It might take some tough love to do that enablement, but the right hire needs this mindset.

One of the other qualities companies should look out for is flexibility.

My day-to-day role is very cross-functional, working closely with Operations, People, and Marketing together.

Ultimately, assessing the effects remote work has on the structure, operation, and people at Oyster. It’s about overseeing a multitude of projects across different teams, and attending to their specific needs.

Another quality is communication, more specifically over-communication and transparency.

Much like the documentarian principle I mentioned before, being clear about your intentions, ideas, and deadlines is so crucial when working effectively in a remote environment.

Finally, an HoR should work on prioritizing habits over tools. Tools are only as good as the processes they exist within and the habits of the people using them. An HoR needs to be focused on habit and culture change first.

Q: What does your role at Doist entail? How has it evolved in the past year or so? Have you encountered people who have struggled with remote? 

chase warrington

Chase Warrington, Head of Remote at Doist

The Head of Remote at Doist is, like many similar roles at other organizations, a highly cross-functional position.

It primarily touches on operations and marketing, with a heavy concentration of remote work advocacy in public, and internal “leveling up” of remote best practices.

In short, it’s my job to ensure we’re continuing to “do remote” at a world-class level and evangelize for others to be able to follow in our footsteps.

One particular area of focus I’m very excited about is the opportunity to work on the “human element” of remote work.

Next year, I’ll be organizing our team retreats and exploring new ways to connect socially in the virtual world.

In terms of actually supporting my team, the conversation has shifted from just making remote work, work - to optimizing it for the long term. With this comes the need for building team camaraderie and culture.

Remote is not for everyone, but just because you crave human interaction doesn’t mean that you can’t thrive in a remote environment too.

The organization needs to see it as a priority to create social opportunities for teammates, and individuals need to learn to bond with colleagues around their work, as well as build a social life outside of work in their respective locations.

I encourage new remote workers to join coworking spaces or a coworking group once per week.

If that doesn’t exist around you, at least create time for a virtual coffee or happy hour occasionally with a teammate.

Also, be clear about separating work from life by putting events on your work calendar that forces you to interact with other people in the real world.

Future of Work

the future of work

Everyone and their favorite news publication want to give a prediction on the future of work. There are so many theories from the Metaverse to the gig economy that it is hard to trust who knows what they are talking about and who is writing sci-fi literature. 

The one thing that many people don't end up talking about where we would throw our opinion is building distributed infrastructures. With the old supply chains clearly not working in an increasingly globalized world, companies need to get creative with how they equip their remote teams and set up their secure IT networks.

The keyword here is decentralization, and that is the solution that GroWrk is building with its global network of warehouses and retailers to send compliant equipment anywhere in the world.

But we digress, the other prediction that caught our eyes in the interviews was with Maya Middlemiss, Founder of Healthy Happy Homeworking.

Q: Where do you see remote work heading in the next 5 years?

maya middlemiss

Maya Middlemiss, Founder of Healthy Happy Homeworking, Freelance writer with 20 years of remote work experience

I think it’s important to bear in mind that the remote revolution of the past 18 months was by no means out of the blue and simply reflected a response to trends that were already accelerating and increasingly enabled by the necessary technology (cloud-based SaaS, fast connections, etc.)

The forced lockdown WFH situation was a double-edged sword in many ways because while many people had their first taste of working in this way, for many it was a terrible experience - and in no way reflective of ‘normal’ remote working, from an individual, business, or societal point of view.

However, many can see past this and have at least had a glimpse of different ways of doing things, as have their managers and other decision-makers.

In 5 years, let's optimistically say we will be past the pandemic era.

Hopefully, past the post-pandemic period of chaotic nostalgic adjustment and adaptation - as people realize that going back to the office is not a time machine to 2019, but that the future offers new possibilities they may not have previously considered, alongside shifts in their priorities and preferences.

Perhaps in 5 years, when it comes to those of us fortunate enough to have a choice, we’ll just talk about work.

About creating and exchanging value in a productive and satisfying way… And the physical location will be one of the least important attributes.

And for all those people whose work does depend on location, I can only hope the value of that will be recognized and appreciated for what it is, a crucial factor in unlocking location-independent working for the rest of us.

Those who service, care, deliver, manufacture, grow, build physical things which we depend on. A priceless gift, which should be valued socially and financially.

I hope we all remember the lessons learned from recent turbulent times and can take ownership of our lives and careers and make positive choices for everyone’s benefit.

Wrapping up

As we enter another new year with more uncertainty than ever, it is important for companies to double down on what has been working what their employees prefer. 

If they still don't have a remote work policy yet, now is the best time to create one along with documenting all your current processes. 

The ones that failed at remote work and went back to the office full-time or haphazardly implemented hybrid work policies, still have a chance to learn from their mistakes and the experts.

However, making the shift to remote-first practices should happen sooner than later because time is running out. 

The most innovative companies a year from now will be the ones that have the most flexible working arrangements and adopt the most cutting edge remote work tactics.


Grow remote with GroWrk. We provide and manage laptops, devices, other equipment and services to remote teams in over 150 countries. 

Schedule a call now 

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Mark Gregory

December 9

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