Have you ever noticed that some people always seem to know exactly what to say to senior executives in social situations? They seem to have small talk down to an art.

Whether it’s at a company outing, a client dinner, or during a break at a conference, they sound witty, intelligent, and self-assured.

Early on in my career, I was too shy to be any good at conversing with senior executives. I either couldn’t think of what to say or ended up saying something bland or forced. Then I’d spend the rest of the time worrying I made a bad impression or no impression at all.

The good news is the art of small talk can be learned

In fact, I’ve become pretty good at “talking to strangers” (which is what my kids call it). With a few pointers and some practice, you can be good at it too.

So how do you sound insightful and confident and make a positive impression?

Here are three tips for more engaging small talk that will better represent you:

  1. Start with common ground
  2. Learn about your senior stakeholder
  3. Tell them about yourself

Start with common ground

If you’re attending a conference or company offsite, an easy way to chat is to talk about what you’re experiencing together. It’s something you immediately have in common.

You want to go beyond the general “what a great event” comment that anyone could say because that won’t make a good impression. It’s a throw-away line. Instead, go a layer deeper in a way that reveals something about you and engages your stakeholder. 

For example, you could share a specific session you were impressed with and why. Or a key insight you gained or your biggest takeaway, then ask about theirs.

If it’s the start of the event, you could mention something you’re especially looking forward to attending and what interests you about it. Then ask about their views.

This brings us to the second way.

Learn about your senior stakeholder

If you know you’re going to meet a senior executive in a social situation, you can prepare by doing some research on what they’re interested and involved in. For example, their hobbies, charities they support or groups they belong to.

But if you’re meeting them unexpectedly, you can use this as an opportunity to discover their interests and anything else on their minds. Especially things you wouldn’t be able to find out easily through public sources.

For example, you could ask them what they do to stay centered in such a high-pressure job, or what they like to do when they’re not working. Based on their answer, you could find yourself talking about your meditation practice, the most recent books you’ve read, or sports teams you follow.

As you listen to their side of the conversation, be on the lookout for something you have in common. It could be your background, your hobbies or anything else that’s of mutual interest.

For example, one of my clients – let’s call him John – discovered the global head of his division also loves hip hop music. That gives John something to reach out about and talk about in an authentic way.

Which leads to the third way.

Tell them about yourself

Small talk in social settings can also be an opportunity to share something about yourself that makes you more human and not just another employee.

For example, sharing the backstory of how my parents fled a civil war and ultimately came to the US as immigrants, and how my father’s family can be traced back 37 generations to a king in China.

Or sharing that you’re planning a vacation and asking what your senior stakeholder’s favorite vacation places have been. Or talking about an article you read recently and the insights you gained.

It could also be a case of showing rather than telling. I remember the moment when we heard a colleague sing at our holiday party and discovered a whole different side of her.

By sharing more about yourself, you can distinguish yourself from others, be remembered in a positive way and demonstrate the kind of person you are. All of which are valuable for advancing in your career.

Just don’t make the mistake of saying nothing

As the saying goes, you miss 100% of the shots you don’t take. So, err on the side of engaging with your senior stakeholders. Trust yourself to represent yourself well.

To boost your confidence and chances of success, it helps to preplan some of the questions you could ask, phrases you could use, and topics you could bring up. This way you can be present and in-the-moment to respond in the way that suits the situation best.

Remember, small talk is an opportunity for discovery

Senior executives are people too. In a relaxed or informal setting, you can learn more about the real person behind the senior title and let them discover more about you. It’s also a chance to show you can be comfortable in your own skin no matter what setting you’re in.

As you engage in small talk, remember to:

  • Start with common ground – it’s an easy way to get the conversation started
  • Learn about your senior stakeholder – a little research and some genuine curiosity can elevate your small talk
  • Show another dimension of yourself – being authentic differentiates you and makes you memorable in a good way

Which of these tips for better small talk will you use next time you’re with senior stakeholders at a social event?

Leave a comment and let me know.

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How to Communicate Effectively at Work

Effective communication is a crucial skill because your career is filled with important conversations, and how you handle them can make or break your chances of success.

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