3 Questions Leaders Should Be Asking Their Remote Employees

In 2021 and beyond, remote work is here to stay.


Alain Hunkins

3 years ago | 3 min read

In 2021 and beyond, remote work is here to stay.

That brings good news and bad news.

The good news: Remote work is working better than anticipated.

A Gartner survey revealed that 82% of company leaders intend to allow their employees to continue remote working at least some of the time into the foreseeable future. 46% say they’ll allow employees to work remotely full-time moving forward.

Remote work is now a key ingredient to becoming an employer of choice. A FlexJobs survey found that not only did 96% of respondents desire some form of remote work arrangement, but 27% said that working from home is so important, they’d be willing to take a 10%-20% pay cut to work remotely.

Remote workers are more productive, too. According to the FlexJobs’ survey, the top reasons for increased productivity include: 

  • Fewer interruptions 
  • More focused time 
  • Quieter work environment 
  • More comfortable workplace 
  • Avoiding office politics 

The bad news: A remote work playbook doesn’t exist.

Sustainable practices for remote work haven’t yet stabilized. As Deloitte reports in their 2021 Human Capital Trends Survey, the top factors needed to make remote work sustainable are:

  1. Introducing digital collaboration platforms
  2. Allowing for personal choice in determining how work gets done
  3. Establishing new scheduling and meeting norms
  4. Investing in team leader training

What do these four factors have in common? 

They all rely on effective leadership.

Workplaces move, technologies upgrade, and processes change, but the fundamental human need for leaders to design an environment where people can thrive and do their best work remains constant.

For people to thrive, here are three questions leaders should consistently be asking their remote employees:   

1. How are you feeling?

If the pandemic lessons of this past year taught nothing else, it’s that some things (life, death, health, illness) are bigger than work. These issues always were bigger; it’s just that workplace norms swept these conversations under the rug. That jig is up.

Today, the stakes are too high (and the stress is too great) to deny the elephant in the room. As Deloitte has found, well-being is now a top employee priority. Leaders need to see their team members as humans first, and employees second.   Asking “How are you feeling?” (and truly listening to the response) is meant to be asked of the human being, not the human resource.  

The cliché goes, “People don’t care how much you know until they know how much you care.” The cliché exists because it’s true. Research by Tony Schwartz and Christine Porath found that “feeling cared for by one’s supervisor has a more significant impact on people’s sense of trust and safety than any other behavior by a leader. Employees who say they have more supportive supervisors are 1.3 times as likely to stay with the organization and are 67% more engaged.”  Asking “How are you feeling?” is the most explicit way to show that you care. 

2. What’s distracting you from being fully engaged?

This seemingly lightweight question packs a powerful punch. It’s cleverly designed to be a mirror. The answer reflects the underlying need that’s unique to that individual. 

For example, if someone answers, “My Mom just took a COVID-19 test because she’s been exhibiting symptoms”, then you know what’s on their mind. You don’t have to play a guessing game.  However, if you never ask the question, you may never get an answer.    

Aaron, a district sales manager, learned this lesson firsthand. He recently held skip-level one-on-one meetings with some of his newest sales reps. He asked, “What’s distracting you from being full engaged?” and was shocked when they told him that what they really needed were headsets to make calls. They had worked for a sales manager for nine months at home without headsets. By that afternoon, headsets were ordered and being shipped to their homes.  

3.   How else can I support you?

Most leaders are promoted to leadership roles because they have proven problem solving skill. Solving problems might make you an effective doer, but it won’t make you an effective leader. There’s a big difference being a high performer and facilitating high performance in others.  

Skilled problem solvers rely on their ability to see the problem, but leading remotely means you literally can’t see your employee and the problems they’re facing.  A key to effective remote leadership is accepting the fact that you don’t know what you don’t know.

There’s so much about a remote employee’s experience that you don’t know.  To find out what they need, you need to ask. “How else can I support you?” is a powerful question that invites employees to co-create solutions with you.   

In this remote world of work, the need to empower workers with agency and choice is greater than ever. Prescriptive-style leadership didn’t work well before the pandemic, It’s even less effective now.

To succeed in this new era, leaders must change their mindset from “commander-in-chief” to “facilitator-in-chief”. They need to go from being a “know-it-all” to a “learn-it-all”. Doing so means shifting one’s primary leadership style from a “push/tell” approach to a “pull/ask” approach.  Using these three simple questions to pull out insights is a great place to start.

Originally published here.


Created by

Alain Hunkins







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