I've recently started working with a new company, and it's great. Every few months, they'll organise for everyone to meet-up in a pub after work for drinks.

There's a meet-up coming soon which I'm looking forward to attending, but am concerned that after the whole "How's it going? Are you settling in alright?" palaver, the conversation will run dry. It might be worth noting that about 80% of them are of a completely different, older generation to myself; I think it'd be unlikely that we have similar interests.

I would consider myself to be quiet and a bit of an introvert, and so find it difficult to spark up, and maintain, conversations with new people.

How can I maintain a casual conversation with a new colleague, who will most likely have dissimilar interests to me?

  • And can you make this question more specific? Starting and maintaining conversations are two different things.
    – user288
    Commented Aug 24, 2017 at 18:16

4 Answers 4


Firstly, do not approach the encounter thinking they will have different interests to you. You may find they have a hobby similar to one of yours. I'd be willing to bet at least one secretly visits Stack Exchange...

But in any case, it doesn't matter if they do have different interests, in fact you may have a better conversation if they have a completely different background, as everything may be a learning experience for you.

The thing to do is actively listen. By that I mean after asking a question really listen to what they say. Use this to ask questions to get more info. Don't bring up what you do until asked. Don't try and interrupt. Just try and learn something new.

But don't let it worry you. If you want to you could prepare some basic chat questions by watching the news. Current affairs can be a good starting point.

  • 1
    Depending on where you are "Current Affairs" can be a good or bad subject, avoid the subjects of "Sex, Politics, and Money".
    – CloneZero
    Commented Aug 24, 2017 at 20:44
  • @CloneZero and Religion.
    – empty
    Commented Sep 20, 2018 at 22:37
  • I tend to stay the heck away from current events. That gets into politics and religion way too fast these days.
    – empty
    Commented Sep 20, 2018 at 23:00

Since you mention they are older generation, you can ask (and compliment) them for their experience.

People love compliments. Asking them to share their journey with the company, or even their journey in this field, or life events, establish the impression that you respect them. Try to identify an influential person, and ask him to share his experience, either 1:1 or to the group. If he share to the group, make sure to read the situation properly and don't let anyone else feel left out (or worse, you attempt to flatter the boss).

Here are some topics you can use

How long they have been in the company?
How was it like when they started working in the company?

How long they have been in x field?

Remember that conversation is always two directional. If they run out of question to ask you, it's your turn to ask them.

Life events can be a topic, but carefully read the persons and situation. Start lightly and keep it general and non-intrusive.


Being an older generation autodidactic-philomath your assumption hurts me. I must tell you "I think you are missing out assuming we only like Classic-Rock, Cadillacs, and child rearing." :-)

Anyway, you will never know if you don't ask. It never hurts to ask questions of people. Active listening is important, but you only need to find the next point to ask another question about that interest you. Oldsters have children around, and those youngsters are interested in everything, that the relatives/friends become fascinated in as well. I am currently learning to enjoy modern music which my niece and nephew like that initially I found terrible. I started teaching one of my junior engineers about Scotch, and he is now more expert than me. I secretly watch gaming videos on YouTube too. So, you never know.

Also, these event's are for the group to get to know each other. Either, you boss or the someone in your work group will probably take you in hand and introduce you around, or at least they should. Plus, people want to talk to the new person and will probably try to approach you. If it's not going well approach your boss or someone you know and ask them who they think might be interesting for you to talk with about an interest or hobby you share.

Depending on where you are "Current Affairs" can be a double edged sword; avoid the subjects of "Sex, Politics, and Money." Here in the USA "Trump" is polarizing even within groups of like-minded people.

You might also try, if you get bored or intimidated, looking for the boisterous group and hover near the edge until you have something worthwhile to contribute, even a witticism will gain you a point, and you will learn a lot about your fellow employees just listening. You might hear something from someone that peaks your interest, and you can pull them aside and talk about later.

Also, go in the opposite direction and look for the quietest person, and strike up a conversation with them; quiet waters run deep, and often present the best conversations. Start with "Hi, I'm new. What do you do?" Then it is just a simple progression of who, what, where, how, why, etc. The quiet people also after some time might be trusted to tell you about the others in the office.

Also, remember that extroverts like introverts, who else is going to listen to us and ask questions? :-]


When I was young, I used to hitchhike for thousands of miles. Most people would pick me up because they were lonely and wanted someone to talk to. So my motto was:

Everyone has at least one good story. It's my job to find that story.

I've heard some amazing stories from people you wouldn't look twice at.

The other story of mine that's relevant is my grandfather liked to tell the same stories again and again from his youth. When I was talking with my grandfather my motto was:

Everytime he tells the same story I'm going to make it a different story.

The way I did that was by actively listening to his story and each time I heard the story I would ask him different questions about different details in the story. And then ask more questions about his different answers.

So try that with your colleagues. The way you dig for a story is by asking an open question and then asking questions about what they tell you.

Some open questions you can use are:

  • What do you do?
  • Where are you from? If they are from here, then ask them how it's changed since they were a kid
  • You have any kids?
  • What do you like to do when you're not working?
  • What do you enjoy most about working here?
  • What is your biggest challenge here?
  • If you could have any superpower, which would you pick? Why?
  • How long has this pub been here? Any beer here I should try?

This can go on for hours. In my experience, most people can talk about themselves forever as long as someone is actively listening.

But if someone asks you a question, have a few stories ready to tell. If they seem to getting bored, hand the conversational ball back to them with something like, "But that's enough about me. What do you think about...?"

One more thing. Laugh at everybody's jokes. If someone holds your section of the table with a story, smile, nod and make appropriate interjections.

You'll get on fine. Younger people have to establish themselves, they tend to be goal driven. Older people have met their goals and tend to prioritize people over goals. So they like to talk.

Have fun!

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