How to Ace Small-Talk With the Boss

How to Ace Small-Talk With the Boss

By Hayley Shaughnessy


The first time you find yourself alone in an elevator with your boss or a senior executive can be a daunting experience. Do you shake hands? Are you in charge of leading the conversation? What topics are off limits? Is a little bit of silence okay? Is a lot of silence okay, too?

Take a deep breath and have no fear because just about everyone has been there, including your boss at some point in their career. There isn’t a conversation formula to follow for every employer-employee interaction, but there are useful tips and tricks to help you shake the nerves and be prepared for just about any small-talk situation.


So…how’s it going?

First things first: when you come across your senior executive or boss, make sure you greet him or her appropriately and professionally. Addressing them by their first name coupled with a handshake is completely acceptable. If you’re just starting out in a new job, feel free to introduce yourself too, just to make sure he/she knows who they’re speaking to or to help them put a face to a name.

From there, let the conversation work its magic and flow as naturally as possible. Try to avoid starting the conversation with “how’s it going?” and change to something a little more specific like, “how is your week going?” This way you’ll be able to talk about your already established common ground: work.


Stringing it together

If your boss offered something in your initial conversation you weren’t aware of or didn’t understand, you can do a little homework to better educate yourself to engage in conversation on the topic again. It also gives you reason to follow up by email to offer your opinion or ask a more insightful question.

In addition, if you remember a tidbit that you shared with your boss that he/she expressed interest in, you’re allowed to bring it up again in conversation. Showing your attention to detail is a good thing. If you’re excited about the topic too – especially regarding a work project – that’s even better. Unabashed interest is the safest way to get past formalities and the rule-driven politeness (it also indirectly shows that you love being an employee at your company!).


For the next time – and the time after that

After you’ve aced the first few run-ins with a senior executive, give yourself a pat on the back and make sure you learn from the interactions. Reflect on any body language that you read or perhaps gave off.

Just because you’ve run into your boss a few times now, there’s no guarantee it’ll be less or more frequent. What is for certain though is as you climb the corporate ladder in your career is that you’ll interact with senior executives on a more regular basis.

But for the time being, you can keep on learning and put the 80/20 rule in your back pocket as a good guide for conversation.


It’s all in the math

Wait, what is the 80/20 rule exactly? Eighty percent of conversation is dedicated to successes, interesting projects and learnings and anything you’ve read or participated in that is work-related. For example, if you’re taking a night course, discussing what you’re learning about would be included in the 80 percent. As for the remaining 20 percent, it’s reserved for the intersection of professional and personal – like discussing books or podcasts that you listen to on your commute to work, something interesting you read in the news, or perhaps a notable event or conference you recently attended. From there you’ll be able to establish common interests to keep the conversation going.


Keep it up

Once you’ve established your small-talk know-how, think about ways that you can input more meaningful conversation. It’s a better use of their time and yours, as opposed to talking about the weather!

The more you interact with the senior staff, the more comfortable you’ll likely become – but remember:  always conduct yourself professionally. This includes in more social settings, such as a holiday party or staff outing. If you’ve demonstrated your small-talk prowess, you might even find that your boss will seek you out for a chat.


For more tips to help you advance in your career, including how to impress top executives at work, visit