Coffee Chats: Best Questions to Ask!


In this post I’m going to share:

  • 3 types of questions you should ask in every informational interview
  • 2 or 3 examples from each type
  • 1 Non-Negotiable question you always want to end with

Let’s get started!

Watch it in action

The 3 Types of Questions You Should Ask

What most professionals are looking for when they agree to an informational interview with you is that they’re trying to see if you have a genuine curiosity about the industry, about the company, and about the role.

And you can show that you do by asking questions from the following 3 categories:

  1. Tasks and responsibilities
  2. Career path
  3. Industry knowledge

Taken together, questions from these 3 categories show them you’ve given a lot of thought on all aspects of the job and company, instead of focusing only on the superficial benefits, like free food for example.

Tasks and Responsibilities

#1 - What aspect of your job do you find most rewarding?

Contrary to popular belief, the “tell me about your day-to-day” isn’t a great question to ask, since you might find a lot of professionals nowadays don’t have a typical “day-to-day” and you still might end up with a vague description of their roles and responsibilities.

By prompting them to think about what they find most rewarding about their work, you help them drill down on specific situations or examples leading to a more concrete answer.

#2 - How is your performance measured? Or put another way, what’s your KPI?

I love this question, because it gets right to the point. How one might describe his or her job is always going to be a bit subjective and arbitrary.

But come performance review time, the metrics that their manager is reviewing them on, those are going to be in “black and white”, it’s just how companies standardize the performance review process.

Their answer will give you a very realistic feel of the workload and responsibilities if you were working in a similar position.

Career Path

#3 - How did you begin your career?

This question is great, because the answer will give you insight into the decisions that person made, purposefully or otherwise, to arrive at their current role today.

You’ll often find that very rarely are people’s career trajectories completely linear, there are usually a lot of unexpected twists and turns, and that may give you confidence as you navigate your own path.

#4 - If you think about a new hire you enjoyed working with recently, what are some of their characteristics that come to mind?

Again, this question prompts them to think of a specific person and provide concrete examples, making it a much more meaningful question than something like “what advice would you have for someone who’s just starting out”.

#5 - What did you find the most surprising about the role?

To be honest, this is just a very nice way to ask “What do you not like about the role”

For informational interviews, coffee chats, they’re usually very casual, so you can definitely ask a question like this and expect to hear pretty straightforward responses.

Industry Knowledge

I feel like this question is pretty self-explanatory and really shows your interest in that target industry you want to be in, but somehow is very rarely asked.

Most colleges and even companies have paid subscriptions available, to not only news publications, but also industry specific resources like eMarketer if you’re in marketing, or Bloomberg if you’re into finance.

And because there are a lot of choices, you want to make sure you’re spending your time wisely and regularly reading up on relevant content instead of having information overload.

So this question is interesting because not only will you get to hear their point of view on current events in a specific industry, but will also give you a chance to show off your industry knowledge, given you have done some homework beforehand.

Pro tip: You can use what you hear from them in your next actual interview, and you get to impress them with the research you have done in a very natural, non-forced way.

Non-Negotiable Question

Last but not least, a question that doesn’t fall in any of those 3 categories, because it’s a question you should always ask at the end of every single informational interview or coffee chat.

Based on what we discussed today, is there anyone else you think I should talk to?

I’m not even exaggerating when I say this question can be the deciding factor on whether you get closer to that dream role of yours.

From a nerdy, statistical standpoint, the more relevant people you meet in a given field, the higher the chance of someone being able to help you get to where you want to be.

It’s very easy to see someone land a great role and chalk it up to luck, and I agree.

But you can increase the surface area of which luck can hit you by putting yourself out there, by asking to be introduced to the next person, by having that next coffee chat.

By not asking this question it’s like leaving money on the table, there’s no downside. The worst that can happen is that the interviewee awkwardly laughs and says “No I’m sorry” and that’s totally fine!

Now you know what questions to ask

Avoid common mistakes by learning about the 5 Informational Interview Mistakes to Avoid!