Make It

A Psychotherapist Shares 24 Conversation Starters He Uses to ‘Build Deeper, More Interesting Relationships' With Anyone

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Most people overlook the value of social relationships; they prefer to keep their heads down and check things off the to-do list. But researchers agree that friendship and sociability are important, especially when it comes to work.

In fact, a 32-year study published in the Journal of Occupational and Environmental Medicine found that when we focus on building deep relationships with our colleagues, we become more productive and creative. Another study found that groups of friends outperform groups of acquaintances in both decision making and effort tasks.

As a psychotherapist and podcaster, my job is to build deep connections with every person I meet. The first step to getting there is simple: Ask questions.

The best conversation starters

Some people feel that asking work-related questions are boring and generic, while others refrain from anything personal, fearing that they might sound intrusive or nosy.

But that's the wrong mindset — both work questions and non-work related questions are perfectly legitimate. It's all about context.

For example, if you don't already have a close relationship with the person, steer away from heavy topics like religion or politics. Instead, start with something small and simple. The key is to show curiosity and slowly build comfort, trust and depth.

Below are some conversation starters I use to build deeper, more interesting relationships with anyone:

For when you're at a gathering and/or meeting people for the first time:

1. Are you enjoying this event?
2. I like your [shirt/shoes/sweater]. Where did you get it?
3. Do you typically enjoy these gatherings?
4. Have you met anyone interesting so far?
5. If you could start over and go into an entirely new career direction, what would you do?
6. Have you been working on any cool projects lately?

For when you're talking to someone that you don't know that well:

7. Did anything interesting happen at work today?
8. Are you currently reading any books you'd recommend?
9. What has been the biggest change in your routine since the pandemic?
10. Have you watched [that TV show/movie/documentary] that everyone is talking about?
11. What's the last good podcast you listened to?
12. If you could be anywhere else right now, where would it be?

For when you already have an established relationship with someone (i.e., you feel relatively close or comfortable with them):

13. How was your vacation to [X place]?
14. How is your [parent/sibling/partner/kid] doing?
15. Are you going back to the office anytime soon? How do you feel about it?
16. Did you finish that project you were telling me about? How did it go?
17. What's your biggest pet peeve?
18. How are you spending your free time these days?

For any situation:

19. How would you describe yourself in three words?
20. What's the most useful thing you purchased on Amazon this year?
21. What would you do with an extra 10 hours per week?
22. What's the craziest thing you've experienced this year?
23. What's your biggest guilty pleasure?
24. If you could be best friends with any famous person, who would it be?

Remember, not every question may be appropriate for every person or situation. Don't ask probing questions that don't mirror the depth of your relationship. Take into account who you're talking to and what you know about them.

Some other helpful tips to remember:

  • Do show kindness, curiosity, engagement and compassion.
  • Do repeat or reflect back on what you hear for clarity.
  • Don't cut them off.
  • Don't push your own agenda.

As with any relationship, starting an interaction marked by respect and trust can create positive energy, engagement and, ultimately, a more interesting relationship.

Joe Sanok is a psychotherapist and author of "Thursday is the New Friday: How to Work Fewer Hours, Make More Money and Spend Time Doing What You Want." He also hosts the popular "The Practice of Practice," where he interviews authors, scholars, experts, business leaders and innovators. Follow Joe on Twitter @JoeSanok.

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