15 Questions to Ask Your Employees and Yourself to Embrace the New Normal and Create a Healthy, Happy Lifestyle and Productive Remote Workplace

Managers and their teams who have been trained on how to work, coach and sell remotely around this unprecedented change and transition are experiencing breakthrough results. These 15 questions will help you and your remote team increase personal productivity while maintaining a healthy, balanced life.

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With the exponentially explosive and sudden global shift around how companies, teams, and customers operate, sell, communicate and collaborate, especially when it comes to managing your team remotely, many managers question how proficient they can be at managing, motivating, coaching and holding their team accountable at a distance, especially if the manager has never managed a virtual team.


To compound this, unless already woven into your company’s current culture, most employees who are suddenly being pushed into becoming a remote employee have never worked remotely before in their career! In fact, Owl Labs reported that 58% of remote workers and 67% of remote managers received no training on how to work remotely.

While working remotely has many benefits, like anything else in life, there are drawbacks. Inc. found in a recent study that 41% of remote workers struggled with work-life balance.

According to Buffer’s annual report, the biggest struggle working remotely is unplugging after work, loneliness, communication, distractions, time zone differences, staying motivated, and taking vacation time. This further reinforces the importance of addressing this head-on with your team, and you, as these questions are just as powerful for you to self-reflect upon.

Virtual Assumptions Will Destroy Your Team and Customer Relationships

Even if you’re used to working remotely, no one is used to working remotely in our new world. Instead of making the costly assumption that your team and customers are doing fine, take the time to schedule a one on one with each person on your team and have this conversation to ensure you’re creating and maintaining a healthy remote team and workplace for them.

15 Essential Questions to Ask Your Employees, and Yourself to Create a Healthy, Balanced Lifestyle, and a Productive, and Supportive Remote Team

Before you rapid-fire these questions to anyone, it’s essential you set positive intent, the WHY behind asking the questions and what the benefits are to them. Here’s an Enrollment Template to position the conversation.

With the extreme change around how we live and work, especially now that we’re all working remotely, it’s easy to feel isolated and uncertain about the future. That’s why I wanted to discuss how I can best support you in this new environment so that you still feel productive and connected to the team, the company, and to your career goals and opportunities while maintaining a healthy lifestyle. Are you open to talking about this now?

Once you’ve clarified your positive intent and the value that’s in it for them, here are the questions to ask.

1. How are you feeling about this transition?

2. What’s working well for you so far?

3. What are you struggling with most?

4. How are you managing and balancing your personal responsibilities and priorities, while staying productive at work?

5. Walk me through how you’re currently managing your day? Can you send me a screenshot of what your daily routine looks like so we can compare how we both manage our day and learn from each other?

6. How have you set boundaries and expectations with your family when you’re working at home to ensure you’re productive and not distracted?

7. What’s your self-care regimen? (Physically, mentally) How much time are you spending each day taking care of you? (Exercise, meditation, taking a walk, getting out of your house/workspace each day? The health benefits of getting outside are priceless.)

8. How are you turning off work at the end of the day so you can be present with your family and yourself?

9. What did you assume would be difficult about this transition but wasn’t?

10. What did you assume would be easy about this transition but was more challenging than you thought?

11. What can you do to stay connected to me and the team so that you don’t feel alone or isolated?

12. What’s your preferred method of communication? (Email, text, phone, video conference, carrier pigeon, smoke signals, Morse code)

13. How often do you want to connect/schedule one on ones? What cadence works best for you?

14. How can I best support you to create a productive, rewarding and supportive workplace that would ensure you’re achieving your business goals while honoring your lifestyle, core values, personal goals, and priorities?

15. Create the Accountability Partner Agreement: To ensure we’re both supporting each other while holding each other to our commitments, can we both agree to be each other’s accountability partner? That means, if either of us notices that we’re engaging in behaviors that aren’t helping us, our brand or our ability to achieve our goals, we can bring this up to each other (via text, email, phone) knowing that our intentions are always positive and supportive. Can you commit to that?

The Continued Evolution of the New Normal

If managers aren’t consistently coaching and communicating with their team, they’ll lose touch of where their people are, who they are and what their needs are in order for them to maintain their performance and well-being.

That’s why I’d suggest asking many of these questions at least every few months, just to ensure you have your fingers on the pulse of everyone’s mindset, goals, and challenges. And not only from a performance perspective, but where they are in terms of their attitude, life-balance, focus, career fulfillment, fears, concerns, and motivation.

Once you weave this conversation into your management cadence, your virtual team will soon become a productive, rewarding reality.


What are your thoughts? I’d love to hear your comments. If you have any questions, feel free to reach out and connect anytime, as I want to be a resource for you. I’ve also opened up my personal one on one coaching practice for those who need a coach the most during these challenging times.

Managers, Learn How to Coach and Manage a Remote Team and Win More Sales. Online Course – on sale now.