5 Questions That Reveal The Personality of Someone You’ve Just Met

Jayson DeMers
4 min readJul 30, 2020
Photo by Sebastian Herrmann on Unsplash

Meeting new people is one of the best parts of life. Every significant other, friend, boss, coworker, neighbor, or acquaintance you have was once just a stranger. When you first met that stranger, you couldn’t have had any idea that you’d form the relationship you currently sustain — or could you have?

It’s impossible to learn everything you need to know about someone the first time you meet unless you have some sort of telepathic insight, but there are some questions that give you a deeper, more accurate picture of someone than others. Simple questions like “are you new here?” at a networking event or “why did you leave your last job?” at a job interview might give you some necessary information, but they don’t tell you about the personality of the person you’re asking.

These five questions, in stark contrast, do. They’re designed to not only give you more direct information about the stranger or acquaintance you’re talking with, but also suggest profound insights about their personality as a whole:

1. How would you describe yourself? At first glance, this question might seem like it’s cheating. The goal is to get a person to reveal his personality through secondary means, so isn’t asking this question a kind of shortcut? Yes and no — it’s all about the ambiguous phrasing, “how would you describe yourself?” rather than “what’s your personality like” or “what do most people think of you?” Notice there’s no cue here — you’re not asking a person to describe himself physically, professionally, emotionally, or in any other specific way. Pay attention to what types of attributes your interviewee chooses to disclose first, and how extreme his word choices seem to be. Shy or meek people tend to choose humbler words like “observant” or “recreational,” while exuberant or extroverted people tend to choose more powerful words like “smart” or “athletic.”

2. What is your biggest accomplishment? This one gives you one critical piece of insight in a person’s past, but also tells you two subtle things about her personality. First, it shows where her biggest interests lie — again, the question is ambiguous, so does she respond with a professional accomplishment or a personal one? How long ago did this accomplishment happen? How does she act when she brings it up? Second, how long did it take her to think of it? If it only comes after a long hesitation, it could be a sign of very many or very few past accomplishments — you’ll have to probe deeper to find out.

3. Have you read any good books lately? The answers you’ll get here vary wildly. First, note the difference between readers and non-readers. You’ll get the occasional person who admits that “I don’t read books,” but more often among non-readers, you’ll find people hesitating a long time before coming up with a book, and then reverting to a classic high school or college text. Among readers, you’ll find popular novel consumers, business and self-help readers, literature nuts, pop science fans, and several other types.

4. What is your dream job? The more ambiguous the question, the better it is. The question isn’t, “what do you want in your next job?” or “where do you see yourself in five years,” but “what is your dream job?” A sycophant in a job interview might simply describe the job they’re applying for. Others may highlight creative pursuits. Still others will describe jobs that don’t exist (or are extremely rare) like “beer taster” or “puppy cuddler.” It will also tell you whether someone’s given this a lot of thought or whether they’ve never thought about it before.

5. Who is your personal hero? This question gets a little more specific and more insightful through obvious ways, but I’ve found it’s a very meaningful question to ask. You’ll find people who describe a family member or someone they knew in life, people who admire an athlete or pop culture celebrity, and people who look up to successful entrepreneurs or businessmen. You might be able to discern something about the intelligence or age of the person you’re talking to here, but more importantly, you’ll learn about their values. What is it that makes this hero stand out above anyone else who ever lived?

Some of these questions are a little too forward to ask random strangers on the street, but once you’ve warmed up a new contact, feel free to break these out. How they react, how they answer, and how they phrase themselves will all speak volumes about the type of person you’re dealing with. This is indispensable for any social interaction, from job interviews and sales meetings to coincidental interactions in public. Get to know people well, and you’ll have far more opportunities.

For more content like this, be sure to check out my podcast, The Entrepreneur Cast!



Jayson DeMers

CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!