Remote work: Prepare yourself for a crucial conversation with management

Jacques Britz
4 min readJun 30, 2020

I am currently working with a long-standing client that was forced into the working remotely paradigm by the COVID-19 pandemic, and so far, it was only somewhat successful. I say slightly because the technology team managed to improve their deliverables and overall output while the rest of the company had severe work performance problems. The performance problems resulted in one part of the organization going back to the office while the other part (technology team) is still working from home, for now, at least.

Photo by Toa Heftiba on Unsplash

In recent weeks the topic of having everyone go back to the office was brushed over in a few of the management meetings, and I honestly did not make too much of it at first. A colleague then made me aware of the fact that unless the technology team comes up with a plan on how they want to continue working from home, they will get instructed to report at the office at some stage.

The first step was to engage with the technology team to see if they are interested in working remotely in the future. The whole group joined the conversation, and everyone agreed that they are more productive, have more flexibility, and see no reason why they need to go back to the office. The next step in this journey is to start preparing ourselves for a crucial conversation with management about us not going back to the office, even after the pandemic ends.

The best approach to convince management that you need to continue working from home is to be proactive about the conversation. You need to spend some time coming up with a convincing argument backed by a plan that you can present to your line manager showing why it is to their benefit to let you continue working remotely.

Photo by Austin Distel on Unsplash

Before you approach your management team, you need to be sure why you want to work remotely and if it is possible at all to achieve your full potential doing that. The two primary reasons why people would want to work remotely are:

  1. Professional reasons might include: a noisy office environment, uncomfortable office setup, water cooler chat taking up a lot of your time, back-to-back meetings are keeping you from your daily tasks. This category is also a great place to mention and celebrate the recent improvements and wins your team has had during the lockdown period.
  2. Personal reasons might include child care responsibilities, daily commute encroaching on your time and sanity, aging parents, or family members that need your time. Don’t be ashamed of prioritizing aspects of your life that have nothing to do with your job. The non-work stuff like your hobbies, family time, personal time are all contributing factors to a healthy mental state, which in turn will also make you a better employee and colleague.

Whatever the reasons might be, you need to be sure that you are honest with yourself and with management. If you need to sort out a personal crisis or family problems, then instead apply for annual leave but do not sell the concept of remote work if you plan to spend your time on other activities and only occasionally check your email.

To prepare yourself for the remote work conversation, you need to put yourself in the shoes of management. The process will not only help to distill your thoughts, but it will also prepare you for possible questions and concerns that need answering. Some of these questions might include:

  1. What are the core hours that you will be available and online?
  2. How will your team know that you are available or not available for work-related meetings, discussions, etc.?
  3. What are your plans for fostering relationships with your colleagues?
  4. How will you attend client-facing meetings?
  5. Will you be spending any time at the office? If so, when will that be, and how will the rest of the organization know that?
  6. How will you make your current work and progress visible to the rest of the organization?
  7. What is your plan for onboarding new team members?
  8. How will you manage the poor work performance of members of your team?
  9. How will you track the performance of your team?
  10. Who pays for your home office setup?
  11. Who pays for the broadband internet at your home? And if the employee pays for it themself, how do you address problems that might arise from a poor internet connection?
  12. What is the arrangement with IT support?
  13. Do you need a laptop instead of a desktop computer?
  14. What are the insurance concerns to keep in mind with regards to equipment stored at your home instead of the office?

These are all questions that you have to think about and, at the very least, have a plan for addressing them. The answers to a lot of these questions are complicated and will need input from other role players in the system, so don’t get stuck in detail trying to find the ultimate solution for each of these possible problems. The mere fact that you are driving the conversation shows that you serious about working remotely, and it’s worth their time to explore the option.

In an upcoming blog post, I will share some of the arguments and answers that we have used in our plan to convince management why the technology team should be allowed to continue working remotely.

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Jacques Britz

Software Engineer, agile consultant, and an avid reader of non-fiction books. You can get in touch at https://www.linkedin.com/in/britzjacques