15 Conversation Starters for Inspirational Leaders to Get to Know Their People

Getting to know people can be difficult, especially if you're an introvert like me. Sometimes being in a position of leadership can add an extra layer of awkwardness to the situation. Some people will relish the opportunity for “face time,” and bend your ear about how great they are while others are wary of talking to the boss and simply clam up.

You can get past this awkwardness through conversations that goes beyond small talk. Read on for fifteen suggestions to start a conversation as an inspirational leader trying to get to know your people better.

A Different Take on Typical Questions

Standard questions people like to ask when making conversation can be altered slightly to encourage more robust answers.

1. Instead of: How was your weekend?

Say: Tell me about the best part of your weekend.

This avoids the standard “good” response and encourages the person to think about what they did over the weekend and tell you about it. And it opens up the conversation for more questions.

2. Instead of: Do you have a family?

Say: Tell me about the people in your life who are most important to you.

Most people who are married and have children enjoy talking about their families because this question is typically centered around the traditional spouse and children family construct. But for others who may be unmarried or don’t have a strong relationship with their blood relatives, asking about the people who are important to them in their lives gives them an opportunity to navigate this question in a way that’s comfortable for them. The important people in their lives could be a spouse or significant other, children, parents, siblings, grandparents, aunts, uncles, cousins, best friends, or mentors. People are always happy to talk about the people they love.

3. Instead of: What’s your favorite food?

Say: Tell me about your favorite place to eat in town.

In my experience, most people enjoy bonding over food. They love to bring food in to the work place for office potlucks and they love sharing meals with friends and family at restaurants. This gives you an opportunity to talk about other places you like to eat and maybe a recommendation to try something new. And now you have something to talk about later!

Work Related Topics

Sometimes it’s easier to get to know someone better by starting the conversation with work. After all, you already know you have that in common.

4. Say: Tell me about the person on your team who was most helpful to you this year and what they did.

For many people, it’s easier to talk about and brag on others than it is to talk about themselves. Asking this question will not only give you an idea of who is performing well, but also insight into the person you’re speaking to. It can also shed some light on the team culture.

5. Say: If there was one thing that might sabotage our team’s success this year, what would it be and why?

This is a question that can make people think. Maybe the answer is easy and obvious, maybe it’s not. Most people know what goals they’re trying to achieve as a team but how much thought did they put into what might set them back? Who knows? You might get an outside-the-box answer that you never saw coming.

As a side note, this is the kind of questioning that you'll find in high reliability organizations. A preoccupation with failure is the kind of mindset that allows an organization to head off any little thing that can go wrong to increase the likelihood of a good or desired outcome. It encourages people to scrutinize everything to ensure they're not missing anything and doesn't condone behavior that normalizes unexpected deviations.

Digging Deeper

Leaders like to ask about people’s hopes, dreams and goals, but I think people hold back on answering these questions with full transparency. Sometimes they’re embarrassed to share this with someone they don’t know well yet. Other times, they don’t want to admit their goals aren’t aligned with the organization where they’re currently employed.

Alternatively, you can ask questions that seek the heart of who they are. The next few questions may feel a bit more personal, so you’ll have to use discretion as to when and where you ask these questions. The answers will give you hints as to what motivates the person and perhaps clue you in to how you can help the person achieve their dreams and goals. Inspirational leaders should be engaged and encouraging, and you can’t do this if you don’t know what drives your people.

6. Say: Tell me about the accomplishment you’re most proud of from the past year.

Let them know it doesn't have to be a professional accomplishment. Knowing what they’re proud of will help you understand what motivates them. What people are proud of can range from earning an advanced degree, being part of a team that achieved a major milestone on a project, helping their children win the science fair or guiding a friend through a tough time. Whatever it is should give you something to talk about and discuss in greater detail.

7. Say: Tell me about one of your most defining moments in life.

A defining moment can be something deeply personal or something they don’t mind sharing. Often people use defining moments to explain their “why” or purpose in life. They center their dreams and goals off these defining moments and dedicate their lives towards achieving these dreams and goals.

Lighter Topics of Discussion

Opening the aperture to more light-hearted topics of conversation is a fun way to get to know people. People are not one-dimensional and will often surprise you. Plus, it shows you have a fun side too. These topics are neutral enough that they can be asked regardless of how well you know someone, and the answers should be enough for you to ask follow-up questions.

8. Say: Tell me about the craziest thing you’ve ever done.

Okay, so maybe you don’t want to know this much about a subordinate or team member. Assuming the answer is something legal, ethical and moral, it can be fun to swap stories about the craziest thing you’ve ever done.

9. Say: Tell me about your favorite book/movie/TV show or what book/movie/TV show are you indulging in right now.

This may seem like small talk but often it evolves into a discussion about similar interests. Plus, you might get some great recommendations from this conversation. This was how one of the most train-wrecky TV shows known to man was recommended to me.

Back in the Spring of 2020, I was a squadron commander for a medical unit. Everyone was responding to and stressing about COVID-19. It was still early in the pandemic and little was known about the virus. But one of my most vivid memories of that time was having a discussion about Tiger King. It seemed like everyone was watching it and talking about it at work. It was a great way to get our minds off of the pandemic and a fun way to bond. To be honest, I watched one episode and couldn’t get into it. But it didn’t stop me from participating in conversations about it, all of which ended with exclamations of, “I can’t believe you’re not watching Tiger King!”

10. Say: Which of these chores do you like to do most: wash dishes, mow the lawn, clean the bathroom, or vacuum the house?

Everyone has to do chores and most probably don’t enjoy them. But maybe you’ll find the one person who likes to do all of the above. Who knows? This is such an off-the-wall topic that anyone can relate to, it’s sure to break the ice.

11. Say: If you could only eat one meal for the rest of your life, what would it be?

Everyone’s got to eat. It’s another way to ask what someone's favorite food is, but at least this time it’s an entire meal. And who doesn’t like to talk about food? Okay, maybe you’ll find the one person who eats to live, but now you know this fact about that person. I'm not saying you have to relate. Just don’t judge.

12. Say: If you could go back in time, what year would you travel to and why?

The idea of time travel is not a novel idea. Movies, television shows and books (like Stephen King's 11/22/63) have been created around this concept and most of us have imagined what it would be like to travel in time. This is a fun topic to discuss and gives you insight to what is important to the person you’re talking to.

13. Say: What's the most unusual thing you've ever eaten?

Yes, another food-centered topic of conversation. Typically unusual food is consumed when people travel, and you don’t have to go outside of the country to try something unusual. I only had to go to Pennsylvania to try scrapple - yes, I consider scrapple to be quite unusual. But this opens up the conversation for discussion about places they’ve visited and the things they’ve seen or done.

14. Say: If you had a warning label, what would yours say?

Like the crazy experience topic, maybe you don't want to know the answer to this. However, it's still a fun question and can give you insight into their personality.

15. Say: What is one thing you will never do again?

Hopefully their answer isn’t, “Have a conversation with you.” And assuming it’s not, the answer to this should lead to some interesting conversation fodder. Maybe it’s a once-in-a-lifetime experience that they were happy to do once and never again. Maybe it’s something more serious, like undergo a surgical procedure. Regardless, what they choose to disclose will give you greater insight into who they are.

Conversations Are a Two-Way Street

The above are suggestions on how to initiate conversations and open the door to get to know your teammates. Some may be more open and receptive to this than others, but it doesn’t mean you should ever stop trying. Just be prepared to answer the very questions you’re asking them. After all, it’s only fair that you do!

Comment below: What are your “go-to” conversation starters that go beyond small talk?