Ask these 5 questions to turn small talk into something more meaningful

Do you despise the awkwardness of making chitchat with strangers? Consider this your cheat sheet to turn it into something worthwhile.

Ask these 5 questions to turn small talk into something more meaningful
[Photo: HIVAN ARVIZU/Unsplash]

Most people find “small talk” challenging. You walk into a room full of strangers who are sipping wine or coffee, and realize there are many people you could build a relationship with, but you wonder which ones to approach, and what you’d say. So you stand there feeling awkward and wish you were anywhere else.


You are not alone. Marissa Mayer, former CEO of Yahoo, admitted that she hates networking events. So once she’s there, she forces herself to stay. “You can’t leave until time X,” she’ll tell herself. Similarly, a COO I once worked with told me he decided to pass on an upcoming industry conference because he loathed “the parts where you have to chitchat and feel you don’t know what to say.”

Even the senior people in the room feel the jitters!

The good news is that you can make these moments meaningful and fun. Here are five questions to ask yourself (and answer) if you want to turn small talk into enjoyable career conversations that can land you that next job, mentor, or client.

1. Why am I attending this event?

Sure, you may be going because everyone else in your department or professional association is attending, but you need to have your own “why” for being there. As Simon Sinek writes in his book, Start with Why, “If you don’t know why you do what you do,” it will be difficult to get others to believe in what you do.

You may just want to be there for the nibbles and friendship. Fine, but don’t expect earth-shattering results. If, on the other hand, you want to make a connection that will advance your career, decide in advance what that will look like. Do you want to meet someone from Bank XYZ so you can sell new services to that client? Do you want to get to know a prospective mentor who is likely to be there? Do you want a reference for a job at another company? Pick one goal, and keep that in mind.

2. Who do I really want to know?

Now that you’re “pumped” with a specific goal, seek out the person who can make your goal come true. Suppose you want to build a business relationship with Bank XYZ, target someone from that bank–not just anyone, but someone who can influence a decision that will benefit you. If it’s a mentor you have in mind, approach her. If you are eyeing a job at Company ABC, look for the head of the department you want to work in . . . or someone who knows that person (and can put in a good word for you).


Make sure you have done your due diligence on these individuals or their organizations. The last thing you want is to walk up to someone and waste their time (and create a bad impression) by having nothing of substance to say. So, for example, approach the mentor only if you already know why you want her to mentor you, and what her credentials are. If you want a reference for a job, be prepared to talk intelligently about that position and that company.

And bide your time until the individual you’re targeting is alone. I once made the mistake of approaching a CEO at a networking event and was totally ignored as he continued to talk to his admirers.

3. What’s my pitch?

Let’s say you’re now in front of the person who’s going to help you and you want to pitch your idea with clarity and confidence. Here’s how.

Begin with one or two sentences of “small talk.” You might say, “Are you enjoying the event?” Or, “Is it your first time here?” “Lovely to see so many senior women here.” That’s enough! Now get to your point. To the prospective mentor, say: “I’d love to have you consider me as a mentee of yours.” Phew–it’s out and you’ve engaged the executive. Next, give the reasons why you’ve asked for this consideration. Advance prep will ensure you have your two or three arguments lined up. Your listener will have points to make, too, but don’t get derailed from what you want to deliver.

4. How will I close?

Once you’ve delivered your message and supporting points, and listened intently to your “mentor’s” responses, close with action. You don’t want to be tentative at this point by asking questions like, “Would you have time to mentor me?” That would give her an easy out–she might respond, “Well, actually, my schedule is very tight.” Instead, begin by saying, “I am excited about the possibility of working with you. How would you feel about that?” After she responds with something like, “I’m flattered, thank you,” pick up the pace and suggest getting together to discuss how the mentoring relationship might work.

This closing is extremely important, because it moves the discussion to action that you and your mentor can engage in, and through that action move toward closure.


5. When can I leave?

These “small talk” events can be stressful, because they are in fact big talk situations, so don’t feel you have to stay to the bitter end. Once you’ve pitched yourself to someone important, you can leave the party, knowing you’ve accomplished something that can move your career forward. And realize that the other person you approached for a favor is probably feeling pretty special, too. After all, you put that person on a pedestal, and everyone wants to feel important.


About the author

Judith Humphrey is founder of The Humphrey Group, a premier leadership communications firm headquartered in Toronto. She also recently established EQUOS Corp., a company focused on delivering emotional intelligence training to the fitness, medical, and business sectors