If you’re an introvert like me, coffee chats with colleagues you don’t know well (or at all) can be a little stressful. You don’t want to ask canned, generic questions, but at the same time you don’t want to seem like a creeper when you ask about a childhood vacation they took because you saw it on Facebook or whatever. Luckily, there’s a happy medium: generic questions that reveal things about the person. Here are a few great examples.

What do you wish you’d known when you first started on this team that would have made the job easier?

This is a clever way of soliciting advice on how to hit the ground running if you’re new to the team or role. Phrasing it this way pushes the person to think beyond the obvious, to the things that went unsaid when they were first new to the team. It’s those less-obvious tidbits that are likely to be really valuable to you, which is why this is a good question to ask.

What do you get up to in your spare time?

While it’s a little expected, there’s a reason this is such a classic question. It lets you get to know the person behind the suit! I’m a huge believer that work is more fun when you know the people behind the job; after all, we’re all human beings just trying to make our way in the world together.

I don’t believe in separating who we are at work from who we are at home; at least, not in the ways that matter. Asking this question during your coffee chat helps you find common ground and build rapport, which is one of the most important things you can do when trying to build relationships with the people with whom you work.

What’s the most fun you’ve had with the team in the past year?

This one is also revealing of both what the individual considers fun, as well as what the team has been doing to try and inject a little fun into the work over the past year. If they’re not able to offer up anything of substance, it might be something you want to keep an eye on. Maybe it’s indicative of team culture – or lack thereof. Maybe not, and the person just prefers to keep to themselves; either way, this is a revealing question.

If you could instantly impart deep knowledge across the team on one topic, what would it be?

This is a way of finding out where potential knowledge or skills gaps may be on the team, in the eyes of your colleague. The answer also gives you some valuable insight into what skills/knowledge the individual believes to be important for success on the team. And again, phrasing it this way encourages them to think beyond the obvious, like “relationship skills, teamwork,” and so on.

What’s the best piece of advice you’ve ever received, and why has it stuck with you?

I’ve built up a collection of advice that others have shared with me over the years, and the very best ones weren’t ones that were said directly to me, but rather advice that was shared with others, who then shared what they were told with me.

One of my person favourites is that whenever possible, you shouldn’t be running away from a job; you should be running to a job that you really want. What this is saying is that you shouldn’t wait until you’re unhappy with your current role to make a move; you should be planning ahead to make a move before you hit that point, so that A) you maintain momentum in your performance, and B) you avoid making hasty career decisions just because you’re not happy where you are. Shout-out to you, Ben, for that excellent tip!

Anyway, by asking this question during coffee chats, you’ll be able to build your own collection of fantastic advice. Plus, I find that people always enjoy sharing their answer to this question; it usually makes them reminisce about a great leader, mentor or colleague 🙂

Wrapping it Up

Coffee chats don’t have to be scary. With a little bit of prep, you can feel confident that you’ve got intelligent questions to ask, and that you’ll receive meaningful answers in return. And remember, these questions are starting points; don’t rush to get through them all as fast as you can! If the answer your colleague provides sparks a deeper question, then explore that train of thought and talk further. If you discover you both have a love of travel, for example, then you’ll likely start sharing stories about the places you’ve been. Don’t rush it; have fun, enjoy the chat, and you’ll have walked away having learned a few things and made a new work friend in the process!