40 of the Best Questions to Ask on Your First Coffee Chat

Your first coffee chat can be extremely daunting.

There’s no doubt about that.

I remember MY first coffee chat; I was in the summer break between having just finished high school and starting university.

I was terrified, and had no idea what to say, and was honestly second guessing myself looking for excuses I could use to cancel on the other person.

Thankfully, I came across a couple of online articles that allowed me to really understand what the point of a coffee chat was, and helped me pick out a list of questions that I could ask.

And I want to do the same for you today.

So, here are the 40 best questions you should be asking on your first coffee chat, to ensure it goes smoothly and that you can walk away feeling proud of yourself and accomplished!

Firstly, let’s start off with some general things to note about coffee chats.

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Things to Note About Coffee Chats

There are a few important tips and considerations I should quickly tell you about, just so you know the basics when it comes to coffee chats, and can make your decisions accordingly.

In no particular order of importance, these things are:

• Coffee chats are generally approximately 30 minutes long, and can be done over the phone or in person (such as at a café).
• The goals of a coffee chat are to make a good impression on whoever you’re meeting, expose yourself to potential career opportunities, or to be introduced to other contacts to expand your network.
• Be respectful of the other person’s time; don’t waste it by asking dumb questions such as which school they went to (you should already know this by doing prior research on their background).
• The beginning and end of a coffee chat are the most important for you to make a good impression; what happens in between isn’t as important.
• Try to ask as many thoughtful, open-ended questions as possible (try not to ask ‘yes’ or ‘no’ questions).
• Don’t ask questions that you could easily Google; instead ask questions that the other person is more uniquely positioned to answer (a bit more personal and relevant to them).
• Don’t get TOO personal (don’t ask about salaries, or antagonistic questions such as ‘why did you choose to study in [home country] instead of a better school like UPenn or LSE?’
• Always remember to thank the other person for their time and to highlight their own achievements, making them feel good too.
• If the call was over the phone, have your personalized list of questions out in front of you for you to refer to.
• If it’s an in-person chat, memorize some questions you want to ask, and try to flow the conversation around these questions.

The 40 Best Questions to Ask During a Coffee Chat

Now, the way that this is going to work; I’ve broken the list of questions up into 7 different sections, including questions that you can ask during the opening and closing phases of the coffee chat, and sections about specific topics you might want to learn more about.

That way, you can pick and choose the right questions YOU want to ask, depending on who you are and what you want to gain out of the coffee chat.

• Opening questions
• Their past experience and career path
• The workflows and responsibilities of their job
• Their firm
• Career goals
• Recruiting (only if the chat is going well)
• Closing questions

Since the average coffee chat is around 30 minutes long, it’s a good idea to pick out about 15–25 questions from this list, so you’ve got enough to talk about.

Remember, depending on what you want to learn about the most, you can choose more or less questions from each section; you don’t have to do an even split across all five questions.

Generally, the opening and closing stages of the coffee chat shouldn’t be too long; just try to keep them around 1–3 questions each.

Opening Questions

1. Tell me a bit about your story and how you ended up working in [field or industry name].
2. What made you choose this role?
3. Was this job what you always wanted to do?
4. What do you like to do outside of work?

Questions About Past Experience and Career Path

1. What’s been the highlight of your career so far?
2. What’s the most rewarding thing about working your current job?
3. What was the most surprising thing you found when you first started this role?
4. Has your role met your expectations in terns of learning opportunities and professional development?
5. What does a typical week look like for you in [their role], and how do you think this differs from the same role in other geographies? (For example, management consulting in Australia likely looks very different to management consulting in the US.)
6. Was there a significant turning point in your career that helped you get to where you are?
7. Looking back on your career path, is there anything you would’ve done differently?

Questions About the Workflows and Responsibilities of the Role

1. What’s your favorite, or the most interesting project you’ve worked on and why?
2. All things considered, do you genuinely feel happy working your job?
3. What’s the most challenging part of your current role?
4. What industry events or conferences do you/have you attended, and what did you learn from them?
5. Can you tell me about your role’s tasks and responsibilities, and how closely do they match up with what Google says?
6. How much do you think your role has changed or evolved?
7. Have you had to make any adaptations to your work, and what were they?

Questions About the Firm

1. What made you choose [firm name] over the others in this space?
2. What’s the teamwork environment at your firm like?
3. If there was one thing you could change about firm or its culture, what would that be?
4. Do you think there is anything that differentiates your firm from its competitors?
5. How well do you think you fit in to the work culture at [firm name]?
6. What are some key characteristics shared among the people who work at your firm?

Questions About Their Career Goals

1. Where do you see yourself in five years?
2. Even if it might be early on, are there any particular career paths that excite you?
3. Do you have any entrepreneurial aspirations in the future?
4. What are you hoping to gain out of your current role?
5. How do you measure the success of your own career?
6. Do you have any plans to diversify your skillset and do something new in the future?
7. How well do you think you are positioned to achieve your future goals?

Questions About Recruiting (Only if the Chat is Going Well)

1. What’s the current recruiting process like at your firm?
2. What do you think allowed you to be successful in landing a role at this firm?
3. Do you have any advice for someone interested in landing a role in your position?
4. What sort of preparation would you recommend someone do to land an interview at your firm/for your position?
5. Who are the key people involved in the recruiting process for your firm?

Closing Questions

1. Touch back on one or two significant points that they talked about, and comment on why it was useful for them to give you that information (this will show that you genuinely care about what they have to say).
2. Knowing what you know about me, is there any more general advice you’d want to give me?
3. IMPORTANT: Based on what we’ve talked about today, is there anyone else you think I should talk to?
4. Thanks again for taking this time to come out and chat with me. It was awesome meeting you; would it be alright if I sent you any follow-ups in the future if they come up?

Remember, being able to ask the right, thoughtful questions is going to allow you to really make a good impression on the people you meet, and it’s important you add your own flair to the conversation and adapt to where your conversation is headed.

Employing the right conversation techniques and making use of your social skills is going to allow your conversation to run smoothly.

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Don’t expect to run through all of your questions, and only run through what the other person seems comfortable or willing to go through.

I’d rather you be overprepared and end the call with unanswered questions, than having to end the call or chat awkwardly because you’ve run out of things to talk about.

Check in with them at the 20-minute mark to see how you’re going for time, and make sure you know whether they’re happy to go for 30 minutes, or perhaps even longer!

Always keep in the back of your head that the goal of your coffee chat is to make a good impression on the person you’re meeting, and to gain some high quality information out of it.

You’ll do that by being polite, showing that you’ve done your research and have respected their time, and by asking thoughtful questions that they will enjoy or have fun answering.