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Conversation Starters for The Awkward and All the Rest of Us Too


Holiday Party 2015


Let's NOT Talk About Grief: Conversation Starters for The Awkward 


As an extrovert ( a person who gets her energy from people), I like parties. I like learning about other people, discovering things I didn't know, and laughing! And as a new widow, many years ago, I also liked NOT talking about my late husband, my kids, or my grief.


But even for someone like me, navigating conversations with a grieving colleague can feel uncomfortable, especially at "happy holiday events." One rule I have, no matter what event or who I am talking to, is to remember that connecting matters most to anyone, grieving or otherwise. 


I was at a party on Sunday and was told, "You ask good questions!" My secret isn't that I'm an extrovert; my secret is that I have a list of 42 conversation-starter questions on my phone. Before I go into any people situation, I pick 2 - 3 questions I will ask.  


Being comfortable at a party is about being prepared. So, I wanted to share a few conversation starters with you. Use them with the grieving person in your office or a holiday team luncheon. Having questions is nice to go into any situation feeling confident, even just a little more so. 


These are not just to help you connect with a grieving colleague but their good or anyone anywhere.   


1. "I know this is a difficult time. What are some things you're enjoying outside of work these days?"

Shifting the focus to their personal life allows them to share something positive and find a sense of normalcy if they need it. By showing genuine interest in their non-work lives, you demonstrate care and may even provide them a space to escape their grief momentarily.


2. "I've been meaning to ask, what was your favorite part of your recent vacation? Or where do you want to go for your next vacation?'

Enquiring about a past positive experience can spark a joyful conversation. Who doesn't like being asked about their last vacation or where they would take their next vacation?


3. "Have you seen anything interesting online or heard any good podcasts lately?"

Sharing a mutual interest or sparking a conversation about something unrelated can create a sense of connection and normalcy, reminding them that life continues outside their loss.


4. "I'm curious: what are you most passionate about these days?"

This question encourages them to talk about something they care deeply about, providing a sense of purpose and reminding them of their values and interests. Watch how anyone who asks this question comes alive and more authentic.  


5. What do you have far too many of?

This is a fun, random question. Everyone has too many of something. Will they share what that is? Ask to find out.  


6. "If these last five years were a chapter, what would the title be?" 

This question invites them to reflect on their recent experiences and share a personal narrative. If I had been asked the question in the first five years after Art died, I might have said, "Crawling the Ashes Into a Different Sun." Or something like that. When asked, these questions allow the responder to express their growth, challenges, and triumphs, providing a glimpse into their journey. They will think you are a great question-asker. 


7. "What would you do if you weren't afraid? What is your guilty pleasure?" 

This prompt encourages them to explore their aspirations and desires. If you go first, you can decide how deep to go. Either way, if you listen well, it will create a safe space for vulnerability and self-discovery.


8. "What is the craziest thing you've ever done?" 

Sharing an adventurous or unexpected experience can spark laughter and positive memories. Everyone has a story to share!  


9. "What's the 'no' or refusal you keep postponing?" 

This reflective question allows them to explore their boundaries and identify areas where they may need to prioritize self-care. It's not a good opening question for strangers, but it is an excellent second or third question if you feel connected enough.


10. "What is popular now that annoys you?" 

This is one of my favorite questions. On the surface, it seems like a breezy question, but you can delve into their beliefs and values and prompt reflection. 



Research on the Positive Effects of Listening


No matter how good your question is, if you're not going to listen, there is no point in asking. I use the 2:1 ratio. If you have two ears and one mouth, use them in that ratio. 


In an effort to connect, we often want to share and find others who have similar values. I suggest instead you treat a party like a treasure hunt; see what you can find out about other people. 


This doesn't mean you don't talk or share, but be conscious if you do all the talking. If your goal is to connect, be a listener! (But you will still get some great benefits!


Several studies have explored the positive effects of listening on both the person and the person being listened to. Here are two key findings: Listening benefits both the listener and the person being listened to. 


  • For the listener, it reduces stress, increases empathy, and improves communication. 

  • For the person being listened to, it reduces loneliness, boosts self-esteem, and enhances problem-solving abilities (Did you read that, leaders leader!).


Conversations should be two-way streets, but I have found that the older I get and the more I listen, the better I feel. So in a way, it's a selfish act!   


Try it. You might like it!  


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