If you’ve read our Introvert’s Guide to Networking, you might remember that disliking small talk can actually be an advantage. Why? Because you’re more likely to come up with insightful, open-ended questions, which could make you stand out more.
Still, figuring out what to talk about with a stranger can be quite daunting. How do you probe deeper without being intrusive? What sort of questions could get a potential mentor to open up to you? And how do you talk about current events without stumbling into the murky waters of politics and religion?
Fortunately, there are a handful of questions that can serve as painless conversation starters. The following should help you get the ball rolling as you figure the rest out:
- What brings you here?
- How did you get into *insert industry/company here*?
- What advice would you give to anyone who would want to enter *insert industry/company here*?
- What’s your take on *recent event relating to their industry*?
- Given your experience, what’s something you wish you knew about your industry/profession early on?
- How do you unwind after work?
- What’s the best way for me to keep in touch with you?

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This question is a light-handed opener. It also establishes your interest in the other person (i.e., you’re not just out to see how they can help you). Furthermore, their answer will clue you in on their objectives. This, in turn, will enable you to figure out how to add value to them.

After you’ve gotten to know a bit about someone’s professional background, you can get them to expound on their journey more. This won’t just make you more likable, but it will also give you some valuable takeaways. Who wouldn’t want firsthand info on an industry or company’s openings, right?

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Okay, at the end of the day, we all want to get new leads on a job or a business opportunity. However, asking for such outright can come off rather boorish. Yikes.
So, the trick here is to employ a little subtlety. Thus, the aforementioned question is a graceful way of asking if your contact knows of any openings in the industry. If you played your cards right, they just might ask you if you’re interested.

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First impressions are key. Apart from being nice, you also want to appear knowledgeable and up to date. This question can help you accomplish exactly that.
As a bonus, this helps you direct the conversation if you’re feeling a bit stuck. Your conversational partner’s answer could help you come up with the next question, or at the very least, teach you something new.

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This is a great question if you’re talking to someone who’s got more seniority than you. People tend to be more generous with their wisdom than with their contacts, and senior players seem to enjoy it especially.
Asking this question also shows deference and can endear you to the person, which can only be helpful to you later on.

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Who wants to talk shop all the time? Most people certainly don’t, hence this question. It’s fairly low-stakes, and veers the conversation towards a more light-hearted direction.
More importantly, this reiterates that you’re interested in them as a person and not just in their job or business. Who knows? You two might just find something you’re both passionate about.

One of the biggest rookie mistakes is collecting business cards but giving away none. Either that, or failing to follow up with the people you meet.
Now, us millennials might be used to pm’s, dm’s, or text messages, but our seniors in the industry might prefer more old-fashioned communication methods. Hence, it’s very important to ask if they prefer to follow up via a phone call or through other means.
If nothing else, this is also a more refined way of asking for someone’s contact details.
Lastly, do keep in mind that you should also come up with your own answers. Good conversation is a two-way street, after all.