Online Check-ins: 5 Questions for Deeper Conversations

How can supervisors manage the performance of employees who work remotely? Here are some ways to maximise your next virtual check-in.

11 Aug 2020 Articles Performance management Work-life harmony Best practices

As we navigate the new normal of working from home and supervising teams remotely, communication is critical in managing productivity and work processes as well as supporting the mental well-being of employees. A recent poll by TAFEP found that while more employers are now open to implementing telecommuting, two of the key challenges cited are difficulty in tracking employees’ work progress and the lack of social interaction that occurs in the traditional work setting. 

One practical step that supervisors can take is to schedule regular one-on-one performance check-ins with each team member.  As more employees adopt flexible work arrangements, a weekly or fortnightly check-in via voice or video call is an opportunity for supervisors to have deeper conversations on project progress updates, troubleshoot performance issues, and with team members.

Some supervisors may shy away from initiating these calls, concerned that their team members may feel monitored or micro-managed. However, research suggests that regular employee check-ins may increase employee retention and foster better communication and trust in their supervisors1.   As a people manager, you can state upfront  that the purpose of these conversations  is to maintain an open channel of communication to surface work issues and provide regular support to empower employees to do their best work. 

Here are five recommended questions you can incorporate in your check-ins, to facilitate constructive conversations with your team members.

1. “Are there challenges you face working from home?”

There is likely to be an adjustment period as employees first transition to a flexible working arrangement. At this point they may identify challenges such as a lack of a quiet workspace, difficulty in bouncing ideas off colleagues at short-notice and even striking a balance between time spent on online meetings and doing deeper work.  These difficulties coupled with a desire to maintain their usual efficiency levels can be stressful.

As a supervisor, you can support your employees, by finding out how well they are adjusting to their new work arrangement and any problems they have faced in this transition. In working together to find solutions, you may also share how you have overcome similar challenges as well.  

2. “How can we work better as a team?”

One of the benefits of introducing flexible work arrangements in the workplace is the opportunity to review and refine work processes. As employees work outside of the traditional office space they will be able to quickly identify which work processes are necessary for the team to function well, and which ones can be fine-tuned or dropped entirely. It is helpful to check-in and understand:

  • Do employees feel that supervisors are communicating clearly and frequently enough?
  • Are digital platforms being used effectively for collaboration?
  • Are there any obstacles to communicating as a team?
  • Are we spending too much or too little time in virtual meetings? 

3. “Tell me about your work week/month. What went well/not so well?”

Online check-ins are also an opportunity to pause and evaluate performance on specific tasks and projects. This serves as a good way to provide on-going feedback to individual team members and sharpen their skills and aptitude. Ask these questions to conduct a quick post-mortem on recently completed projects:

  • What was done well?
  • What are the areas for improvement? 
  • What will need to be done differently for the next similar project?

4. “Are there areas of work that you are currently concerned about?”

As a supervisor, you may see signs that an employee is struggling on specific tasks or projects. Proactively asking this question can lead to an employee sharing openly about their work challenges, and help you quickly identify ways to support them. If a team member is feeling overwhelmed, they may need help prioritising their workload, better time-management or even refreshing their work skillset to work more effectively – areas that you can help them with, once you have identified the key issues. 

5. “How can I support you as you work from home?”

This question is a useful catchall that supervisors can use to conclude an online check-in. It provides a quick ‘temperature check’ on who requires immediate support and the specific actions that can be taken. It also provides employees with an opportunity to surface any work challenges that did not come up earlier in the check-in conversation.

Asking the right questions are only the first step in having deeper and more meaningful conversations that build stronger relationships with employees. Listening actively and taking concrete action to address their concerns will assure your team that supporting them is a priority. Supervisors should follow-up during subsequent check-ins, to identify if there have been any improvements. Over time, as employees become accustomed to regular online check-ins, supervisors may find their team members sharing more deeply, and get richer insights on how to support their teams as a result. 


1The Next Generation Workplace Report. (2019). Retrieved 4 August 2020, from