21 Conversation Starters That Will Help You Build More Successful Relationships
There are no bad questions—only poorly framed ones
“The paradoxical secret of charisma is that it’s not about trumpeting your good qualities, but making the other person feel good about theirs.” - Brett McKay, The Art of Manliness
When it comes to meeting new people, the best conversationalists approach their job with one goal in mind — advance.
People who are great at starting conversations come in all shapes and sizes, but the underlying lesson all of them have learned is that people like to talk about themselves.
They use this to their advantage by asking a question that allows them to create a small opening, and inch by inch, they move the conversation forward until interest is generated, and ultimately, trust is built, so a second conversation is earned.
Like the quote above says, building relationships is not only about showcasing your good qualities but bringing them out in other people (which is the best quality).
The purpose of the list of conversations starters below is to give you a few ideas that will allow you to “spot that small opening” — so you can minimize the small talk in your life, meet more interesting people (which is everyone if you ask the right questions) and build more win-win relationships.
Some of the questions below you may find cheesy, some may hit home, so grab a few you connect with and make them your own.
Reframing Ordinary Questions Into Interesting Ones
For the longest time, I thought that having a few big name magazine logos on my back was the coolest part about writing. Then I realized that influencers were a little bit more likely to talk to me. It was not until recently my eyes opened to the true power of writing: I have carte blanche to talk to anyone.
I can now reframe every question from, “Sorry to bother you, do you mind if I ask you a question?” to “Hey guys, sorry to interrupt. I am working on an article and over the last few weeks I have been asking everyone I meet this one question…”
But in reality, writer or not, “The last few weeks I have been asking everyone I meet this one question…” is just as effective. It gets people interested in what you are about to say and is a refreshing change from the standard, “What do you do?” type of question.
I love life lessons and career/life advice so the questions below are what I use, but with that intro, it can go any number of ways.
“The last few weeks I have been asking everyone I meet this one question…”
1. What is the best piece of advice you can offer to a recent college graduate?
2. What is the greatest lesson you have learned from one of your enemies?
3. What about your mentors?
4. Why was your best boss your best boss?
5. What book would you recommend to someone starting out in their career?
6. What is your favorite speech, and if given the opportunity to give a talk about whatever you wanted, what ideas would you talk about?
7. Being an entrepreneur with a family, I have found it difficult to disconnect after work. Do you have any ideas on how to better disconnect?
8. What skill/skills do you think will most be in demand in the next five to ten years?
9. Is “following your passion” good advice or terrible?
10. I just got married, what is your best piece of advice to keep my wife smiling?
11. If you did not need to sleep, how would you spend the extra eight hours a day?
12. How different is your job today from what you wanted to do as a kid?
All of the questions above work well one on one and in group settings, and all of them generate more than one-word answers — which is the enemy of all conversations. They open people up to talk about the lessons they have learned while dropping hints about who they are and if their values align with yours in a way that is unexpected and a nice change to the standard conversation starters.
Speaking of group settings, if you are not comfortable being the center of attention (even though the questions above are perfect for introverts, as after one question you can shut up and still be deemed interesting) or are shy and prefer to speak to people individually, give the compliment plus guess equation a shot.
When the group separates, go up to the person you want to speak with and say…
13. As someone who is great with people, are you in sales by chance?
14. As someone who is obviously comfortable in their own skin, are you a coach?
Or it can be as simple as….
15. You are really funny. Are you a comedian?
Speaking of guessing
The next time you meet someone and have the urge to resort back to the old, “Where are you from?” or “What do you do?” question, stop yourself, and try this reframe instead:
16. Where are you from? Wait. Don’t tell me. Let me guess.
17. What do you do? No, wait. Give me a clue and let me guess.
This simple switch lightens the conversation and turns a one-word answer (again — your enemy) into a fun conversation.
Other questions that work just as well:
When at a networking event
18. If you weren’t here tonight, what does your normal Tuesday night look like?
(A bit more interesting and not as weird as someone coming up to you and saying “What do you like to do for fun?”)
19. We haven’t met, but I believe that we have a few mutual friends in common.
20. I am only in town for a few days, any recommendations off the beaten path?
21. How do you know the host? (This one is so easy and opens so many doors for a conversation to take place).
The questions vary and need to be tailored depending on the conversation and circumstances, but they open people up to who they are while giving them a chance to showcase their personality and talk about things that are important to them.
Like I said in the intro, people like to talk about themselves. So don’t make it harder than it has to be. Ask a question that allows them to do just that.
Once you’ve opened new doors and made new connections, moving those connections is the next step.