How To Make Workplace Small Talk Less Awkward

by | Career Growth

Although I was nicknamed “Mr. Loquacious” by my fifth-grade teacher, I’m a proud introvert and have never been a fan of small talk, especially in the workplace.

It feels awkward, makes me sweat, and often triggers my anxiety. As a career coach who spends much of my time teaching people how to land jobs, I also understand the importance of networking, which often involves considerable small talk.

Whether you want to simply survive small talk or get better at creating meaningful conversations at work, keep reading. In this article, I share:

  • Why workplace small talk may feel awkward
  • The benefits of trivial conversations in the workplace
  • Ways to make small talk less awkward and more interesting
  • 15+ questions to ask to make workplace conversations more engaging
  • Questions and topics to avoid discussing in the workplace

By the end of this guide, you’ll feel more comfortable and confident in your ability to navigate workplace conversations with ease and authenticity.

Why Does Workplace Small Talk Feel Awkward?

One of the reasons workplace small talk can feel awkward is that it pushes you out of your comfort zone. These conversations often take place with colleagues and clients with whom you may not have established deep relationships. The lack of familiarity can create tension and uncertainty about how to engage effectively.

Another reason these conversations can feel “off” is varying comfort levels with small talk among different personality types. For extroverts, small talk can often feel natural and energizing. On the other hand, for introverts, it can feel less instinctual and draining, leading to discomfort in initiating and sustaining these conversations.

Additionally, many people perceive small talk as an inefficient or unnecessary use of their time. If you’re an introvert with a limited social battery, you may feel like dedicating your energy to small talk is a poor investment.

You might also be unsure about the topics you can and cannot discuss, which I cover later in this article.

[Read: 7 Empowering Interview Tips For Neurodivergent Job Seekers]

What Are The Benefits Of Small Talk At Work?

There are a number of benefits to these seemingly trivial workplace conversations. One of the most significant is building trust, which can make it easier to move projects and initiatives forward, as so much often relies on your relationships with colleagues.

Another advantage to small talk is that it allows you to gain insights into colleagues’ perspectives, talents and strengths, and professional backgrounds. This understanding is important because it fosters more empathetic and collaborative working relationships.

Additionally, workplace small talk can provide you with an opportunity to connect and decompress with colleagues. These conversations are especially important when working remotely, since “water cooler” chats can be harder to come by.

Furthermore, engaging in small talk can decrease your stress and improve your overall job satisfaction. At the end of the day, it doesn’t hurt to have colleagues you enjoy chatting with.

How To Make Small Talk Less Awkward And More Interesting

Fortunately, small talk doesn’t have to be awkward or dry. Here are some strategies to make it more engaging:

  • Develop a list of talking points: As a major introvert, I find it helpful to have a handful of go-to stories and open-ended questions ready. Importantly, I adapt my list depending on whether I’m attending a conference or hosting a group call, taking into account the context and audience.
  • Ask thoughtful follow-up questions: When someone shares something interesting, be sure to pose a follow-up question. This is my go-to strategy for moving the conversation from small talk to a meaningful connection. A good probing question (or two) can lead to a much deeper conversation.
  • Embrace the silence: Silence can feel uncomfortable when engaging in small talk, but try to embrace it. During my graduate counseling courses, I learned to count to 10 or even 20 before interrupting the silence. This practice allows slower thinkers an opportunity to contribute.
  • Practice, practice, practice: Getting comfortable with small talk takes time. Give yourself the gift of patience as you develop this skill.

How To Make Small Talk Less Awkward And More Interesting

15+ Questions To Make Workplace Small Talk More Engaging

Here are some questions to try that can make workplace conversations less awkward and more engaging:

  • What’s your go-to coffee or tea order?
  • What’s your favorite Disneyland ride?
  • How did people describe you as a child?
  • What was your first job?
  • What did you want to be when you grew up?
  • What was your college major, and why?
  • What’s the latest book you read?
  • What’s your favorite podcast?
  • What’s a TV show you binge-watched recently?
  • What’s a hobby or interest you have that might surprise colleagues?
  • What’s your top way to celebrate a work accomplishment?
  • What was the last vacation you took?
  • What’s your Enneagram type?
  • What’s the weather like where you’re dialing in from? (I love posing this question when facilitating a Zoom call with people from multiple states or countries.)
  • How does your family/your culture cook rice? (Also great for group video calls; courtesy of Amber Spry)
  • What makes you fabulous? (My absolute favorite question!)

Questions To Make Workplace Small Talk More Engaging 1

Questions To Make Workplace Small Talk More Engaging 2

Questions To Make Workplace Small Talk More Engaging 3

These questions are simply a jumping-off point as you explore deeper connections with your colleagues. Please get creative and lean into questions that interest you. Personally, as a Disneyland Magic Key Holder, I always love asking fellow Disney lovers about their favorite character. (Mine is Stitch!)

What Questions Are Not Suitable For Small Talk At Work?

Some questions and topics are genuinely not appropriate for small talk at work, including:

  • Physical or sexual comments
  • Health details
  • Age or family planning
  • Personal finances
  • Negative gossip about colleagues
  • Deeply personal or invasive queries

Important: Context matters. Your role, company culture, and geographical location will determine the precise questions and topics that are suitable for discussion.

As a career coach, I’ve had clients work at companies ranging from Fortune 50 financial institutions and tech giants to international humanitarian organizations and political offices. The topics appropriate for work have varied dramatically. For instance, it would be impossible—and inappropriate—to suggest limiting “political conversations” when working for an NGO or political organization.

Final Thoughts On Workplace Small Talk

While I can’t guarantee that you’ll love small talk, my hope is that these strategies will make the practice less anxiety-producing and more approachable. Keep in mind that small talk is a skill that takes time to develop, and with enough practice, it can become a valuable tool in your arsenal. You’ve got this!

About Dr. Kyle Elliott

About Dr. Kyle Elliott

Dr. Kyle Elliott is the founder, tech career coach, and executive coach behind CaffeinatedKyle.com. He has helped his clients land jobs at Meta, Amazon, Google, and nearly every other tech giant you can imagine.

Dr. Elliott’s insights have been featured in Business Insider, CNBC, CNN, Entrepreneur, Fast Company, Fortune, Harvard Business Review, and The New York Times, among dozens of other leading publications. He has been recognized as a Best Career & Interview Coach, Best Resume Writer for Silicon Valley/Tech Managers & Executives, and LinkedIn Top Voice (the platform’s highest honor).

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