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12 Brilliant Questions That Will Make People Remember You and Like You More in 2021

Not long before the pandemic, I had an idea. 

A lot of people find networking uncomfortable. So, I shared some tricks: a series of go-to questions I’ve developed over the years as an author and journalist, that almost always get people to open up and talk about themselves.

Now, after 18 months of social distancing, remote work, and other societal reactions to the pandemic, I think we need a new list of icebreaker questions.

What makes a good icebreaker, especially if you’re a business owner or meeting people in a professional setting? I think they usually have three things in common:

  • First, they’re open-ended questions. As long as the other person involved wants to play along, they’re not normally answered with just “yes,” “no,” or another single-word response.
  • Next, they’re phrased in a way that makes it easy for the other person to respond with an answer that’s at least partially optimistic, upbeat, and even amusing. This makes it more likely that they’ll associate their memory of you with positive emotions.
  • Finally, they’re designed to elicit interesting answers that you won’t have a hard time paying attention to. This is crucial because the entire point is to start a conversation, not just to elicit information and move on. You have to listen.

Like a lot of things in life, these are easier to explain with examples. So here are a dozen brilliant ideas to get you going.

Some of these are pandemic-specific; others are simply things that I think will work well in a post-pandemic, meeting-people-again world. Let’s start with an easy one:

1.    Has there been a silver lining to the pandemic for you?

I like this one to start because it addresses the elephant in the room -; the pandemic -; but it does so with an optimistic assumption. When it works well, you’ll hear about something positive, and that memory will now be linked to their memory of you.

Maybe the person you’re talking with appreciates having had more time with family. Maybe they learned a new skill they wouldn’t have otherwise. Maybe they made a big change and learned something about themselves.

Of course, not everyone has had an overwhelmingly positive experience during a global pandemic! Perhaps they’ve suffered real loss, but asking the question this way gives them control over how much to share. Worst-case scenario, you move onto another question.

2.    What part of your job would you like to do more of?

This is an especially good one for a business owner or boss to ask employees. Again, it starts with positivity and an assumption that the person does like his or her job. 

What’s more, even if it’s asked casually, it can give you valuable information. And as the person answers, it usually leads to a story: “I like to do X, because it allows me to do Y.”

3.    How do you think we would have handled the pandemic if it had happened 10 or 20 years earlier?

Personally, I think about this question all the time. If we hadn’t had reliable broadband Internet and videoconferencing? Forget it. Imagine if we’d had to do this during the 1980s, when making a long-distance phone call incurred a per-minute charge. 

I like that this question can reveal something about what is important to whomever you’re talking with. For example, a young, single person without children might ask this question of a working parent, and realize by his or her answer that they’ve had very different experiences.

4.    What’s the best purchase you’ve made for remote work?

I think half the things I have in my home office came as a result of asking people this icebreaking question. It can also lead people to explain that they haven’t really been able to work from home, which can lead you to all kinds of other interesting inquiries.

Again, it starts with a positive assumption -; that this other person has managed to cope -; but allows him or her to control the terms of the answer.

5.    What’s the most interesting thing you’ve read or watched that you might not have otherwise?

This is kind of a 21st-century edition of “Read any good books lately?” 

I like asking it this way just because there’s a hook: the pandemic (although they’re really free to tell you about anything they read or watched). Also, since people don’t read books to the extent they once did, I like to broaden it to things they’ve watched, too.

Again: It’s a bit of a silver lining question. You were introduced to something good (whatever you read or watched), as a result of something bad (a global pandemic).

6.    What worried you at the beginning of the pandemic that didn’t wind up being a problem at all?

This is a really good question. It incorporates both positive outcomes (it wasn’t a problem after all!) and shared experience -; because I think a lot of us were worried about things that didn’t come to pass. 

In my case, I might point the fact that in March 2020 I bought about $200 worth of pasta and sports drinks that I stockpiled in our basement, and then went to two ATMs so I could withdraw $1,000 in cash. At the time, I had in the back of my mind that grocery stores would close and there might be a run on the banks. Happily, I was way off.

7.     What were you doing exactly one week ago, or one month ago? 

This is a great one because it starts with a quick puzzle that you can do together (Wait, what was the date a week ago? What day of the week was exactly one month ago?)

Then, it involves a bit of a memory exercise, and on top of that, it lets the other person control his or her narrative. 

As an example, maybe a month ago, I was heading to the beach. But if I wanted to be super-specific, maybe I was running around my vacation house, trying to remember where I’d left my bathing suit to dry. Or maybe I was playing with my daughter on the bumper cars on the boardwalk. 

It’s my choice how to tell it: straight facts, amusing specificity, or a fun memory.

8.    How did you get your first job?

This one is great: It’s so open-ended, it might have zero to do with the pandemic, and it gives the other person permission to walk down memory lane. 

I think most of us have fond memories of our first jobs, even if we didn’t like the work particularly, because those jobs remind us of our younger, greener selves.

9.    How do you think you’ll get your 15 minutes of fame?

This one is pretty close to once I used to ask pre-pandemic, except that I like to ask it now with an assumption that the person hasn’t actually had a “15 minutes” experience, yet. 

If they’ve had a good one, they’ll probably tell you. But if not, this question can get them thinking about what they want for the future, or what they expect will happen — combined in a kind of comical package.

10.    Do you remember the first time you won a trophy or a medal?

Again: We start with a positive assumption, which is that you got an award of some kind. For most people, it was probably a long time ago, which makes it easier to tell the story without false humility. Or else, maybe it will give you insights or be funny. 

11.    What’s the single article of clothing you own that you’ve owned the longest?

If someone has saved an article of clothing for years, he or she either really likes how it looks, or it reminds him or her of a good experience. Either way, there’s going to be a story, and it’s probably a positive one. 

12.    Did you have a Zoom shirt?

Didn’t we all have Zoom shirts? I like asking this one in the past tense. The pandemic might not really be over, but at least expressing it like that shows optimism. 

The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.

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