Questions to Engage Remote Workers

As most of us continue to navigate the adventure that is remote work, it is more important than ever to create engaging, dynamic, and ongoing dialogue with your team. Leaders who understand the benefits and challenges their teams face working off-site are the ones who can help shape the experience for maximum impact and success. Here are eight open-ended questions to spur open conversations with your team members. 

Conversation Starter #1: “What’s the best thing that’s happened to you today?”

This is one of the ultimate conversation starters because you are providing an opportunity for the other person to begin thinking positively—and positivity is always a bonding multiplier.

Conversation Starter #2: “What’s the thing you are most looking forward to this week?”

Similar to question #1, this question is an invitation to find something good—even in times of uncertainty and instability.

Conversation Starter #3: “What’s your most challenging obstacle in working remotely?”

This is a great conversation for two reasons. First, you are asking the other person to analyze their current experience—and that always gets the creative juices flowing. Secondly, this question allows you an opportunity to help and provide assistance based on how the person responds.

Conversation Starter #4: “What are some of the most satisfying things you are finding about working remotely?”

Similar to the previous question, this inquiry helps your team member look for the silver lining. And although it may be small, there are always silver linings.

Conversation Starter #5: “What do you miss most about being at the office?”

In the words of the immortal Joni Mitchell, “Sometimes you don’t know what you’ve got ‘til it’s gone.”  And it’s totally true when it comes to working virtually as well. Get ready because the answers to this question are always interesting.

Conversation Starter #6: “If you could change anything about working remotely, what would it be?”

This is a great question because it triggers thoughts related to maximization of circumstance and experience. Said another way, the answers to this question might just enable the person to start making some significant changes to their home working environment—and that’s always a good thing.

Conversation Starter #7: “What are the three words that would best describe your remote working experience?”

This is a ridiculously effective question in getting your dialogue jump-started.  Simply share the question—and sit back and listen.  Just be sure to give the other person some time to think it through. 

Conversation Starter #8: “What would be the perfect day for you when working remotely?”

There are so many good things that will come from this question. As a result of asking this question, you might even be able to help the other person organize their days so that every day is the perfect day.

Parting Thoughts

When your team is working remotely, it’s your job as the leader to keep them engaged.  

One of the best ways you can do this is by incorporating one or more of these questions into the conversation. You may be surprised and delighted as to how they inject energy and lighten the mood.

Remember: when your conversations get stale, your team won’t look forward to your interactions. And if people don’t look forward to speaking with you, it’s unlikely you’ll ever make the magic necessary to change lives and transform circumstances.

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