6 Ways To Start Deep Conversations with Coworkers Over Lunch

By Cai Wen Wong   •   5 min read
One phobia when entering a new workplace is superficial office talks. These small talks never seem to get anywhere, and it can be quite frustrating especially if they are prolonged. Here are 6 instant tips to steer clear of face-value chats, and truly get to know the person for who they are.

1. Stock-up on conversation starters

Running out of conversation topics? It’s probably a sign that you need to be a little more savvy of the current developments around you. You can start with the latest topic trends on social media. Try the serious stuff like controversial world news, or thought articles and inspiring TED videos. Not a fan of serious content? You can also find out about the latest hunts to do over the weekends, nifty everyday hacks or indulge in some quick doses of humour that you can use to entertain your peers. The goal is to stop looking at the world through a pipe and start exposing yourself to things that are beyond your area of interests. What does this do for you? It makes you interesting! Or at least it’ll minimize the chances of you hitting a conversational roadblock. Like fishing, you’ll soon tug on a topic that resonates deeply with a colleague. Once that happens, remember the winning topic and expand your knowledge of it for future conversations.

2. People LOVE to talk about themselves more than you know

Taking a genuine interest in your colleague’s life is a step closer to breaking the “small-talk barrier”. Even though they don’t admit it, people like it when conversations revolve around their personal interests; although I’m not suggesting that everyone’s a narcissist. If you’re lost for questions, you can try some school camp icebreakers. Get to know the basics of their background through ambitions, hobbies and life pursuits. For instance, “What do you do in your free time?” not only gives you an insight on their life beyond working hours, but you can also use this information to strike common topics with them in the future. Don’t do this all within a single conversation though, lest you want to make it feel like an interrogation. The aim is to cultivate a habit of being conversationally vulnerable with you. Play your cards right and your colleague will soon let you in on their personal opinions of life.

3. Embrace your vulnerability

In order to get your colleagues to open up more, start by doing so yourself. Be open about your imperfections. Any insecurities you may have that you’re currently working on, or anxieties about entering your new workplace. By starting the ball rolling, your colleagues are more likely to reciprocate and share more about themselves. It is normal for us to want to portray an overly polished and put-together image of ourselves, especially when in the workplace. Give it a break. Remember that you’re trying to make a friend here – not talk to your job interviewer.

4. Great listening is an under-appreciated skill you should master

Now that you’re getting the other party to open up, don’t make the mistake of being a terrible listener. Some people tend to over-analyse conversations or body languages, but fail to listen. They then walk away with knowledge of something entirely different than what was discussed. Pay attention, and show that you’re paying attention. React to the conversation with small nods, change of expressions and laughter, wherever appropriate. If necessary, raise questions for clarification. Maintain an appropriate amount of eye contact, and if your colleague is providing an advice, consider rephrasing what they said to ensure that you understood it correctly. But beyond all these, clear your mind and keep your focus on what your colleague is saying. Instead of worrying about how you should react, empathise with what they say, and listen to understand – not to respond.

5. Branch off

You can also try to branch topics off  the flow of conversation. See how person B does it in the short conversation below: Person A: I just bought a Subaru yesterday, it’s so much more convenient to travel around now. Person B: Oh, Subarus are good, very reliable and solid. What model did you get? Person A: Subaru Forester. It’s a great family car. Person B: Ah, that’s nice! How many people do you have in your family? Breaking it down, Person B picks out topics from what Person A says and expands on them. This is a good technique to use when you want to take conversations deeper. Fish for deep topics with each sentence, and you’ll definitely find one that interests both of you.

6. Be real, always

Sincerity is key to building a relationship that permits deeper conversations. You can do any of the previous tips and still fail, if people find you insincere in your interactions with them. There are countless ways to achieve a deeper conversation, but the most crucial way is to just be real. Be true to yourself, and to your colleagues. Insincerity is easily detectable, so always be honest with how you feel in a conversation and let your colleague’s impression of you do the rest.

Cai Wen Wong

TalentTribe Writer

An optimist with an unsatiable curiousity about the world around her, Cai Wen is on a journey to chart her own career path. She finds value in exploring the tricks of the trade in various industries, taking a leaf (or two) from the big players in the market.