What are your biggest concerns about letting your employees work remotely?
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Let's start with what will NOT be a concern.
Productivity of the employees will not be a concern. Having the teams perform over the last year and half of working from home, the fear of productivity loss generally associated with remote work has been eliminated.
Loss of collaboration/innovation due to missed opportunities of "water cooler conversations" will not be concern either. Having modern communication tools like Teams/Slack, etc. and collaboration tools like Azure, JIRA etc., I don't think teams are missing a beat on getting their creative juices flowing.
What will concern me will be more on softer side. With work from home, the line between work and personal life is getting blurred. When you are able to take the meetings in your pajamas, the workday starting as early as 6 AM, especially if you have teams working in EU time, is much common phenomena today compared to couple of years ago. Similarly, on the other side of the day, if the work desk is just 20 feet away from the dinner table, the workday doesn’t end till the dinner is half-cold on the table. These typed of work-life imbalances have an overall wellbeing of the employee and adversely impact the performance in the long run.
Another concern will be related to information security. With a larger percentage of home wi-fi routers with admin password as “1234567890”, home networks are not as secure as they need to be, potentially enterprise data at risk of inappropriate access. In addition, being outside of company premises and firewall, company laptops are more susceptible of malware/ransomware attacks compared to while being on secure enterprise networks in secure office buildings.
Having talked about these concerns and not-concerns, I do think that the benefits of remote work/WFH outweigh the concerns, so my vote will be “Aye” for WFH.
Effectively managing them.
Getting an overall picture of what is happening. Most people only raise concerns or volunteer information when they are in close contact with you.
Certain work can only happen in the office. This sometimes mean that those in the office are doing more work that those WFH. Do you then pay those in the office more?
Couple of challenges
1, Trust building
2. Managing teams remotely and evaluating their performance
3. Building the office culture.
Having said that WFH is the right choice in this pandemic

The broader issues of team building, culture, bonding remain. We tend to see this question from a employer/manager perspective. Flip it to individual POV.
Career development - Remote working has opened up opportunities in a much more democratic way. This also means that one needs to be proactive and vocal to get noticed and this is where cultural differences across regions show up even more. Executing on current roles worked through the pandemic, how much of growth happened? Was it seamless? How about inducting new members? Did they assimilate fast enough?