Your career forms one relationship at a time, not from one job to the next

For over a decade, master interviewer and Esquire columnist Cal Fussman traveled the world on a shoe-string budget.

When Tim Ferriss, a legendary interviewer in his own right, asked Cal how he was able to do this, Cal shared a story.

At the beginning of his journey, Cal was traveling through Hungary, and he was eager to learn about the country and the people in it. So one day, he turned to an elderly woman on the train and asked her the following question: “Excuse me, I’d love to know how you make your goulash.”

To his surprise, the old woman’s face immediately lit up. She then turned to the rest of the passengers on the train and made an announcement: “All these years I’ve been riding this train and this American sitting here is the first person to ever ask me how I make my goulash.”

Later that night, Cal not only tasted the elderly lady’s secret goulash recipe firsthand, he also found a place to stay for the night.

But the free food and lodging didn’t end there. For the next six weeks, he was passed from house to house as he made his way through the country. According to Cal, this was all thanks to asking a woman whose face looked like it had a story to tell about her goulash.

Cal learned many valuable lessons on his travels. When it comes to building relationships, none is more important than this: Most people will like you if you begin by showing interest in them. Asking them about their opinions, experiences, and interests is a great place to start.

When it comes to maximizing networking events, unless you’re at a cooking convention in Budapest, Cal’s line of, “How do you make your goulash?” probably won’t get you very far.

But it will absolutely get you far if, instead of viewing networking events as an opportunity to press your own agenda, you adopt Cal’s mindset and approach each event as an opportunity to learn as much as you can about the people in attendance.

In short, if you want to get the most out of networking events, stop focusing on building your business and start focusing on creating new friendships.

The following list of conversation starters was designed to help you do just that.

Let’s dig in.

Two Bullet-Proof Ways to Kick Off Conversations

Over my 17-year career in sales and communication, I’ve worked across three continents, and honestly, I can’t remember how many networking events I’ve attended. However, I do remember which questions have sparked the best conversations and have led to making the most connections.

One thing I’ve learned is that most people don’t respond well if you hit them immediately with a question. There needs to be some sort of cushion first. From my experience, variations of the two statements below generate the most interest and effectively encourage people to speak with you:

1. “Hello, sorry to interrupt, but over the last few weeks I’ve been asking everyone I meet this one question…”
2. “Hello, my friends and I have been arguing about something. Would you mind serving as our tie-breaker?”

Both of these leads are very hard to walk away from. They immediately build intrigue and they signal to the person/people you are speaking with that an interesting conversation is coming.

Plus, they’re a nice reprieve from the standard “So, what do you do?” type of questions.

Quick aside: For all you writers out there, here’s a potential gold-mine for you: “Sorry to bother you, but I’m writing an article and over the last few weeks I’ve been asking everyone I meet their opinion regarding this one question.”

Here are some more variations on this first approach that I’ve used to great effect over the years.

“Hello, sorry to interrupt, but over the last few weeks I’ve been asking everyone I meet this one question…”

1. “If you could take the stage and give a talk about anything you wanted, what would you talk about?”
2. “Why was your best boss the best?”
3. “What type of job would you suggest for someone who is just beginning their career?”
4. “What’s the greatest lesson you’ve learned from one of your mentors?”
5. “What’s the greatest lesson you’ve learned from one of your enemies?”
6. “If you could choose any new skill to learn, what would it be?”
7. “What’s your definition of success?”
8. “What is the most important quality of an effective leader?”
9. “What’s the nicest thing someone has done for you at work?”
10. “If you could have any job in the world, what would it be?”
11. “Do you think virtual meetings will ever be as effective as in-person meetings?”
12. “Besides getting comfortable speaking in public, which other skills do you think create the most opportunities?”

You might have noticed the above questions are all work-based. Below are some more laidback questions that can help start solid conversations. Feel free to mix up the conversation lead a bit by making it less formal.

13. “If you didn’t have to sleep, how would you spend the additional eight hours?”
14. “What superpower would you like to have?”
15. “If you could choose your age forever, which would you choose? Why?”
16. “If you could do it all over again, what would you study?”
17. “What’s one book every human being should read? Why?”
18. “What’s your favorite quote?”
19. “Do you have a personal slogan or a set of words you live by?”
20. “How different is the job you have today from what you dreamed of doing as a kid?”
21. “Most personal development writers are full of shit, right?”
22. “What activities help you the most to disconnect after a long day?”
23. “What’s the one place people should never go to for vacation?”
24. “What’s the most important quality you look for in other people?”
25. “What productivity hack has been most effective for you?”

Now that you’ve seen the lead above in action and you’re armed with a bunch of conversation-generating questions, let’s move on to the next ice-breaker.

26. “Hello, my friends and I have been arguing about something. Would you mind serving as our tie-breaker?”
27. “Which skills do you think will be most in demand in the next five years?”
28. “Do you think having strong communication skills is the key to having a successful career?”
29. “Just follow your passion is terrible advice, right?”
30. “Do you agree that working from home isn’t nearly as effective as working in an office?”
31. “Do you think having a gap-year should be mandatory before people begin university?”
32. “Most startups fail because their founders are delusional about how easy it is to start a business, right?”
33. “Women should have at least one paid year off from work after having a baby, right? And men at least six months, like in most Nordic countries?”
34. “What role will smartphones play in the next decade?”
35. “Listening to audiobooks isn’t nearly as effective as reading, is it?”
36. “Do you think people can change?”
37. “Do you think universities do a good job helping students find jobs after graduating?”
38. “Do you think having strong relationships with your co-workers is the key to being happy at work?”
39. “Do you think your network determines your net worth?”
40. “What’s one subject in school that isn’t being taught but absolutely should be?”

The beauty of these questions is that they get people talking about their opinions and experiences, which is much more effective than walking up to someone and talking about yourself.

When you ask someone about which qualities make a great leader or boss, you’ll begin to see if your values align with theirs.

When you ask someone about what type of speech they’d love to give or which book they’d recommend, you’ll learn about their interests.

Not only that, but the odds are high their answers will provide you with openings to continue the conversation in a natural way. For instance, learning whether others think gap-years are a good idea will open the door to asking questions about where they went to school and what they studied. This allows the conversation to start off in an engaging and memorable way.

Needless to say, the above questions work well in both one-on-one and group settings.

“Guessing” Conversation Starters

Speaking of group settings, if you’re not comfortable being the center of attention and you prefer talking to people individually, try giving the “Compliment + Guess” equation a shot.

“Compliment + Guess” conversation starter

After the group separates or the person you want to get to know better begins walking away, approach them and say:

41. “Sorry to bother you, but I couldn’t help noticing how great you are with people. Are you also in sales?”
42. “I really enjoyed the story you told back there! Are you a motivational speaker?”
43. “As someone who is obviously comfortable in their own skin, are you a coach by any chance?”

This framing is super effective not only because most people love compliments but also because these questions allow you to learn more about what the other person does and to do so in a fun way.

Speaking of guessing, the next time you meet someone and you have the urge to resort to the old “Where are you from?” or “What do you do?” question, stop yourself and try this reframe instead:

“The Guessing Game” conversation starter

44. “Where are you from? No, wait, don’t tell me. Let me guess!”
45. “What do you do? Actually, don’t tell me. Give me a clue, and let me guess!”
46. “Growing up, my dad and I used to guess people’s names and, believe it or not, I got pretty good at it. I once guessed 497 people’s names correctly in a row. Is your name Bob?”

Then, take a stab at their profiles by observing their accent, clothing, mannerisms, etc.

Oldies but Goodies

When attending your next networking event, you could also go with these oldies but goodies:

47. “If you weren’t here tonight, what would you be doing on a normal Tuesday evening?”

This question immediately opens the door for people to talk about their hobbies, interests, side-projects, and families. This makes it easy to see if you share common interests with them.

48. “What’s your favorite part of your job?”
49. “What advice would you give yourself if you could rewind the clock to when you were just starting out?”
50. “What’s the best advice you were ever given?”
51. “What do you like to do on the weekends?”
52. “If you could start a business today, what would it be?”

Or How About These Questions If You’re Visiting a New City for an Event?

53. “I’ve never been to San Diego before. Do you have any recommendations for places to see off the beaten path?”
54. “I’m getting too old to go out drinking all night, but I love trying new restaurants. What’s your favorite spot that not a lot of people know about?”
55. “Do you have a trick to get rid of jet-lag?”
56. “If you had a free day and $100 to spend, what would you do in town to maximize every dollar?”
57. “This is my first time at an event like this. Is there something I absolutely shouldn’t miss?”
58. “This is my first time at an event like this. Is there something you’d recommend I not do, just to be safe?”

And Last but Not Least, My Go-To Conversation-Starter, Which I’ve Recycled Time and Again

59. “I believe we have a mutual friend in…”

This one comes with a caveat: you have to do your homework before the event. Fortunately, social media makes this easy.

Most networking events are plastered around places like Facebook and LinkedIn, which makes it easy to determine who will be in attendance. A quick cross-reference with names that pop out on LinkedIn will allow you to see if you have any mutual connections. Take the time to confirm you actually share real connections, as everyone on LinkedIn seems to “know” everyone else.

A Bullet-Proof Way to End Conversations

A big part of leaving a strong first impression that doesn’t get nearly as much play as it should is mastering how to end a conversation.

I never kick off conversations by introducing myself. There is a good reason for this: most people have a hard time remembering names, especially when they hear a name without any context behind it.

So, instead of leading with, “Hi, my name is Michael,” I’ve found much greater success leaving my name for the end of the conversation. For example, “I really enjoyed speaking with you. I only have one more question: my name’s Michael. What’s yours?”

By exchanging names at the end of a conversation, you raise the probability of both parties remembering them. Not only that, the conversation “ender” above is guaranteed to get a smile, and it presents an opportunity to ask for contact details: “I had a great time getting to know you, Luc. Would you mind if we connected on LinkedIn and continued this conversation at a later date?”

Pulling It All Together

Networking events can be uncomfortable. Believe me, I feel your pain. I grew up with a severe speech impediment and I still stutter when I’m nervous.

However, since adopting Cal Fussman’s mindset by positioning networking events as a chance to develop new personal relationships, I’ve grown to really enjoy them. As a result, my professional opportunities have also grown. A big reason for this is that I’ve collected the conversation-starters above and tailored them to the specific situations I encounter and the people I meet.

The bottom line is that, like anything else in life, you have to find your own way by figuring out what works best for you as an individual. My hope is that the ideas discussed in this article will help you do just that.

Remember, careers aren’t built one job at a time — they’re built one relationship at a time.