A First-Aid Kit for Remote Newbies

Posted on  Mar 12, 20 by Stefania Chiorboli
how to work remotely

For most companies, going partially or fully remote is a conscious choice. They either start remote from the very beginning or make a transition that allows them to refigure how they work when not everyone is sharing the same office. As I write this, having just joined Boundless, governments around the world are urging companies to adopt this model of working due to the COVID-19 outbreak. 

I made a deliberate choice to work remotely many years ago as it was much easier to look after my two children. I have found my way, and I have built a plethora of habits on how to make it work. I learned from the best in the industry. I wouldn't work in any other way. However, I fully understand just how difficult it can be to have to start overnight, especially for managers and leaders. In this post and the next ones to come, I want to share what I have learned so it can be a little easier for you. 

Reevaluate what you do

When you work from the office, a lot of the things you do during the day come automatically to you. As you move to a remote way of work, you will have to evaluate the importance of each thing you and your team do and cut out the fluff. Start by making a list of what are all the things you do daily and weekly. Don't get lost in the details. Then point out the essentials that guarantee business continuity. It could help to review OKR's (or equivalent) and what are the steps you need to take to support your teams in achieving these objectives. Consider what information employees need to perform the best they can. Please have a chat with the other managers and see how they have whittled down their lists and what tasks and activities they are getting rid of.

It's likely the process of finding the right way of work will take time so be flexible and patient until you find a model that works for you. 

Communicate clearly

Once you have the list whittled down, write it down. Having things in writing creates clarity in a moment of utter confusion. Then as you communicate it, mostly in writing, be clear, kind and concise - when people are in doubt, they'll be able to search for their answers. Whatever amount of communication you think is enough, it probably will not be enough so err on the side of overcommunicating. Create one or two checkpoints during the first weeks to make sure everyone is clear, and where you will have a chance to over-communicate if necessary. 


Express everything and be mindful of the fact that text can come out drier. Use emojis to help make the text more dynamic and fun. Also, be aware that when you are pinging people, they may be in the middle of something, so don't expect an instant reply. When you write to them, drive down the essence of your question, and leave it there so the person will be able to answer at their convenience. These are the essentials of asynchronous communication that will be important to implement.

After a couple of weeks sit down again with your team and some of the other managers and reevaluate if things are working out. Check what worked and what didn't and adjust. Maybe an afternoon check-in is better than a morning one. Give whatever change you implement some time and then evaluate. Rinse and repeat. 

Change your expectation from hours worked to output

This is probably the most crucial point to make - you will need to switch expectations in how you monitor work. Working hours and time in front of the screen will make little sense in a remote setting, and instead you will have to learn to focus on delivery and output. You will have to relinquish the idea of controlling whether people are working. 

You shouldn't worry about people slacking because, as you switch to focusing on their output, that will be your best measure of success. Take some time to write down what you think is the realistic output on a daily or weekly basis and monitor for that. You will have to detach from the notion of being able to control how, where, and when that output happens. It doesn't matter. At a GrowRemote webinar we just ran, our guest Laurel Farrer explained this well with a car wash analogy - when she gets her car washed, she just knows it's clean; she doesn't need to know what soap/tools the carwash person used. Map any potential dependencies that may exist between different people's production and adjust accordingly.

how to support those working remotely for the first time

Provide emotional support to your employees

This is an important one. Right now, employees are suddenly finding themselves forced to work from home based on extenuating circumstances. These employees are likely used to many social interactions during the day, which are now going to be limited. This may create a sense of isolation, anxiety and self-doubt. As a manager, you should provide emotional support to negate that: 

  1. Start by setting up virtual coffee and lunchrooms that people can join at any point if they would like to in order to spend time together the way they would have in the office. Be sure to clarify these are optional, but also ensure to encourage their use on an ongoing basis. This time is essential for the social fabric of your company and for offsetting the isolation your employees are inevitably going to experience. It will allow for people to keep talking about non-work related topics, like the fear they may be experiencing right now. 
  2. Mitigate the negative feelings that may occur in people by sending suitable materials proactively. When I first started working for Automattic, the company highlighted the fact that many people experience imposter syndrome, which tends to be increased in a remote setting. Watching videos on the topic helped me to deal with it. Vulnerability will be a big thing in the coming weeks so I would recommend any Brene Brown TED talk. I would also highly recommend her book, The Gifts of Imperfection.
  3. If you can, arrange for care packages to be delivered to employees: perhaps a basket of food or a food voucher. This will send a message of care and can also be used as a great incentive and reward as people get more used to this way of work and achieve milestones.  
  4. Set up HR helplines so people can speak with HR reps in the company about how they are feeling openly. Moving to working from home at this time is a big transition and people may be having a tough time. Be explicit that it’s okay for employees to talk about their feelings, and that there is support for them. 
  5. Encourage employees to keep essential habits - get dressed for work, do exercise or yoga, go out for a walk in the sun. Maintaining these habits will be invaluable in the long run. 

Be very self-aware about your trust issues

If I asked you whether you trusted your employees, you would most probably answer you did. That's based on the fact that you see them every day. Once you stop seeing them every day, you may not feel as confident. However, you can't let that erode the new kind of relationship you are building with them. Trust and autonomy will create a much better quality of work with more engagement by the employees. You do not have to look far to find data about the positive impact of remote working, such as lower employee turnover rates and better products. Working on your trust issues will be celebrated in the long run.

how to provide emotional support to remote employees

Learn from those that have been there

Keep learning how to do this better - this article is only the start. Use the time you're saving on commuting to study up on remote working strategies. There are remote businesses out there who've thrived for years as remote organisations:  Automattic, Buffer, InVision, Basecamp, Zapier, Doist, and GitLab to name a few. Read their blogs and advice. There are also companies that have already published COVID-19 specific guidelines such as Human Made, which are a great example of clarity, and attention towards employee mental wellbeing. For a more thorough read, grab a copy of REMOTE: Office Not Required by Jason Fried and David Heinemeier Hansson, founders of Basecamp. Right now, if you purchase it, they are offering a reimbursement.

I hope these actions will help you navigate this difficult time. If you have any questions, do not hesitate to get in touch through twitter: @boundless_HQ. A strong team of 11, we have all been through a lot of remote work and are happy to help you navigate these or any other challenges you come across. Stay healthy and safe. Learn more about how you can employ remote employees legally and compliantly.

Need help in figuring out how to employ your international workers?

Speak to an expert
The making available of information to you on this site by Boundless shall not create a legal, confidential or other relationship between you and Boundless and does not constitute the provision of legal, tax, commercial or other professional advice by Boundless. You acknowledge and agree that any information on this site has not been prepared with your specific circumstances in mind, may not be suitable for use in your business, and does not constitute advice intended for reliance. You assume all risk and liability that may result from any such reliance on the information and you should seek independent advice from a lawyer or tax professional in the relevant jurisdiction(s) before doing so.

Written by Stefania Chiorboli

Related Articles

Your 10-Step Guide to Remote Compliance

Running a global, remote-based organisation carries a raft of HR compliance challenges. But fear not! We’ve come up with a simple guide to help you meet these challenges head-on and establish yourself as a leading, people-first employer.

Continue Reading

Rethinking Employment In A Distributed World

If leaders do not make their companies fit for a world where a remote and distributed way of work is far more prevalent, they risk becoming less competitive employers. A change in how we operate is needed, which goes beyond opening up the recruitment pool and advertising remote-friendly jobs.

Continue Reading

The Best Countries for Women to Work in 2022

Let’s take a look at some of the good work going on around the globe - considering pay, maternity packages, flexible working and forms of leave specifically catered to women and their circumstances.

Continue Reading

How an Employer of Record Affects You as an Employee

To employees, employment may seem relatively straightforward at the front end - sign a contract, get paid once a month, receive a payslip, take some time off when needed. Managing the back end is where the complexity begins.

Continue Reading

A People Ops Guide to Providing Emotional Support to Employees

Nowadays, nothing is normal, which means that any work-life troubles are only a small puzzle of a very complex and challenging situation. In this unchartered territory, which none of us know how to navigate, we all need to support and be there for each other.

Continue Reading

Suddenly Remote: Tips for Leaders to Succeed

Excellent communication is at the heart of making remote work, work. With the change from co-location to a remote setting, the goals that you have, the deliverables that you're trying to reach and follow through on are not changing. What mainly changes is how you communicate.

Continue Reading
© 2020 - 2024 Boundless Technologies Limited.
The Greenway, 112-114 St. Stephen's Green, Dublin, Ireland.