Simple conversation starters

Conversation is a lost art. I’d even venture to say that some people forgot how to carry on a decent two-way discussion with others.

I’ve been doing podcast interviews since 2014. Many times, the interview is a free-flowing back-and-forth conversation. Occasionally, there is someone who monopolizes the conversation and makes it all about him or her. My record is currently a 13.5-minute response to one question. I swear the guy never took a breath.

Or there’s the person who answers in short, one- or two-word responses, like a typical church lobby conversation. It’s almost like trying to talk with a teenager. You know the type.

“How are you?”


What’s new in your life?


“What did you do this week?”


That’s why I was intrigued by a recent article published by Thrive Global in which 10 of their readers submitted suggestions for questions to ask co-workers beyond the typical “How are you?”

“When we ask more thoughtful questions, we might get more interesting answers. By asking a co-worker a deeper question, we open the door to something greater than surface-level small talk. And the results can be powerful,” wrote Jordan Hutchinson, the associate editor of content development at Thrive

While the article focuses on improving conversations at work, the skill is truly needed everywhere we go. One of the saddest sights is to see a table full of people simply staring into their cell phones and probably reading about the lives of others.

Starting and carrying on quality conversations is something people over 50 can model for their children and, especially, their grandchildren.

Here are some of the suggested questions submitted by Thrive readers:

1. What are you passionate about outside of work?

I like this one because everybody is passionate about something. You can sense when you’ve struck gold because the other person’s demeanor changes as though someone flipped a switch. Their eyes sparkle and they become super-animated in describing their source of genuine passion.

You might have to follow up with some specific questions asking about side hustles, sports or hobbies. Hopefully, the person’s passion isn’t binge watching a Netflix series. But, even then, if you can get someone talking, who knows what rabbit trails the conversation may lead you down.

2. What do you want to be celebrating in five years?

This question gets to the core of someone’s big goals. Perhaps he or she wants to be out of debt, finish a degree, retire, take a trip or write a book. There is a good chance you can offer advice or share a story about something similar you’ve been able to enjoy or always dreamed about doing.

We often have far more in common with each other than the differences the media claims we have. The question also opens the door for you to make a deeper connection by sharing a resource or offering to introduce the other person to someone in your network who may be able to help them reach that goal.

3. What movies or books have you been enjoying?

I am a huge movie fan and I’m always on the lookout for recommendations for something I haven’t seen. Like many people, I have a library of books that I will read “someday,” but there is always room on the shelf for one more. 

Asking for a recommendation opens a window into their personality. Do they like comedies or romances? Are they more matter-of-fact in preferring non-fiction and documentaries? Or, do they like to escape into fictional stories?

A great follow-up question is, “If you could write a book, what would it be about?” Trust me, everyone has a book idea they’ve contemplated writing about. Getting them to describe it may just motivate them to take the first step to make it a goal for completion — especially if you express interest in the topic, too.

4. What opportunities have you received or attempted lately?

Perhaps they have a business idea, got a promotion at work or have an opportunity to take a trip. Whatever it is, let them outline the opportunity and take some time to do some dream-building to help them realize it’s not an impossibility.

If the person claims to have had no opportunities, then ask what opportunities they wish they had? If time or money was not a factor, what would the person chose to do? This really opens a door for a discussion around their sense of purpose or, better yet, a smoldering desire just waiting for an opportunity to ignite.

Keep talking

Here’s a little secret. People LOVE to talk about themselves, once you can crack that shell. It’s the one subject for which most people can talk about for hours.

When meeting new people, you have an open door to ask just about anything because you truly have an interest in knowing more about that person and what makes him or her tick.

Throughout the conversation, keep looking for commonalities, such as shared likes, interests and experiences or even things neither of you really enjoy.

Many times, when people have an opportunity to talk about themselves with someone who is fully engaged in the conversation by acknowledging what has been said and making comments or asking follow-up questions, it works to put you in a better light.

It’s funny how someone will describe you as being “so nice,” when all you did was listen to them talk about themselves.

To view Thrive’s other conversation starters, visit

I’d be interested in knowing what questions you like to ask others to kick off a fun or meaningful conversation. Share them with me at the Forward From 50 Facebook group, or drop me a note at