Cultivating conversations to deepen relationships during the COVID-19 pandemic.

You’re connecting with people you haven’t talked to in years. Or maybe you’re talking more often with your spouse, friends, and family than you have in a long time. It’s great to connect and spend time with each other (even if virtually), but you may find that conversations remain surface-level rather than getting deeper. Or perhaps you just aren’t quite sure what to ask the people you are hearing from and reaching out to.

How do you take those conversations further? How do you get past “Q: How are you? A: Given the circumstances, I am doing well. How about you?”

It was only recently that I started learning that we can actually train to be better listeners, better communicators, and therefore, to connect better with others. (This seems like one of the most essential skills of being human, why isn’t it emphasized more? But I digress…) We are realizing that we need each other right now in ways that we might have been able to escape five weeks ago. But that doesn’t mean that we have all of the tools to help us connect with one another. How do you continue a phone conversation with Aunt Jane whom you haven’t talked to in five years? How do you encourage your friend from high school to share how he is really feeling?

First, take care of yourself.

I heard recently that the first step to being a good listener (which is essential to being an effective communicator) is self-care. If your basic needs are not being met, then how can you be present with someone else? Take care of yourself now – you know best what that means, whether sleep, nutritious eating, time alone, exercise or movement, etc. Then make sure those in your home have their basic needs met. Then start reaching out to others.

Other important steps to being a good listener that I learned recently include: letting go of assumptions, checking your understanding by reflecting what you hear, and sharing how you are impacted on a personal level by what you hear.

Second, ask good questions.

Have you ever been talking with a friend about a decision you are making, and they ask a question that gets you thinking about the issue in a completely different way that leads to new insight into your decision?

Or, think about a time when you were in a conversation and someone asked deep thought-provoking questions instead of sticking with “how do you know the hosts?”

Here are some ideas on questions to draw from in your next video or phone conversation. Or maybe even those at home with you. Let me know how it goes, and please share other ideas to connect right now!

Here are some questions from psychotherapist Esther Perel with a couple added from Tim Ferriss in their recent interview found here. (And I recommend the entire interview for great tips on connecting during COVID-19). In addition to these, Esther encouraged listeners not to be afraid to ask more, to take this opportunity to go deeper, and to go with the next question rather than stopping.

  • Are there people who have been reaching out to you that surprise you?
  • Are there reactions of others that surprise you?
  • Are there people you want to connect with and now is a good time?
  • How are members of your family?
  • Tell me about your brother or sister [or other family member]. How are they doing?
  • What marks your day today?
  • What did you notice today that you don’t usually notice?
  • Are you sleeping?
  • Are you eating?
  • If I were to ask your husband or wife how you are doing what would he or she say?
  • If you want to know how someone is doing and they say something like “I’m doing well” or “given all that is going on, we are doing well” or “given the circumstances, well” you can say “you just told me how are things, and I am asking how are you?”

Here are a few that I liked from this site that might be good questions right now:

  • What passion project are you working on right now?
  • What was the highlight of your day today?
  • If you had to pick any character in a book, movie, or TV show, who is the most similar to you? Why?
  • When you were growing up, what was your dream job? Is any part of that still true?
  • What’s your biggest fear right now?
  • Do you have any regrets? (Such as not acting sooner to isolate during the Coronavirus pandemic, or not selling investment assets, or…?)
  • Who is your role model?

Finally, during my health coach training at the Institute for Integrative Nutrition, they provide good coaching questions. Here are some that might be useful right now:

Relating to the Future

  1. How will it be different once you have a solution?
  2. What would be available to you if…?
  3. What would be the very first sign that things are back on track?
  4. What would happen if you lowered your expectations?
  5. What would happen if you raised your expectations?
  6. What would it feel like if…?
  7. What would it look like if…?
  8. What would it look like if you were able to get past…?
  9. What would make that fear decrease or disappear?
  10. What would success look like?
  11. What would the outcome be if…?

Relating to the present

  1. In the present moment, what emotional sensations can you identify?
  2. In the present moment, what physical sensations can you identify?
  3. What is the most pressing thing happening now?
  4. What is working well in your life right now?
  5. In the present moment, what’s happening?
  6. Where do you feel stuck?
  7. What is most comfortable about where you are now?
  8. What are you grateful for in this moment?
  9. How do you feel when you consider…?

Digging deeper

  1. And then what?
  2. Can you say more about that?
  3. How did you decide that?
  4. How is this significant?
  5. What do you mean by..?


  1. Did anything surprise you when…?
  2. How can you expand your life in that area?
  3. How does this serve you?
  4. How does this not serve you?
  5. What are you looking to create?
  6. What can you control in the situation?
  7. What do you enjoy about…?
  8. What’s missing for you?
  9. What’s working for you?
  10. What’s the best part about this for you?

Let me know if you try some of these questions or tips and how it went! Or offer your own ideas. Leave a comment or let me know on Facebook.

One thought on “Cultivating conversations to deepen relationships during the COVID-19 pandemic.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.