What Are Good Questions to Ask During Coffee Chats?

cup of tasty coffee with froth in cafe with people

Networking is one of (if not THE) best way to build connections and get jobs. Even beyond job-hunting, networking is still important for business. The most loyal customers and partners usually come from within your network. But how exactly do you network? By following 3 simple steps:

  • Reach out to people
  • Make a good impression
  • Follow up

I’ve already covered the cold outreach part in a separate post, but today we’ll be focusing on the actual chat. It doesn’t matter how many coffee meet-ups you schedule. If you leave a bad impression, you’re not going to get any help. One of the BEST ways to leave a good impression is by asking good questions.

In this post, I’ll cover the criteria that every good question should follow. On top of that, I’ll also throw in a couple pretty generic questions that you can use for almost anyone. Let’s jump right in.

Mannerisms and Impressions

“What you say doesn’t matter half as much as how you say it.” – Business Insider (+ a boatload of other famous people).

Let’s imagine 2 scenarios real quick. In both of them, I’m chatting with you about the same things over the same medium. But in ONE, I’m extremely hostile/annoyed with you and in the OTHER I’m friendly and humorous and we get along well. Which conversation will you enjoy more?

Seems like a nobrainer, yet so many people forget about this during coffee chats / informal calls. Lawyers, doctors, bankers: they’re all human! And so they all would enjoy a pleasant conversation over an awkward/rude one. Keep this in mind and you’ll have a way better chance of building good rapport.

Before we go ahead exploring the specifics of question content, it’s important to go over a few key points that could dramatically shift the outcome of your networking calls:

  • Be friendly and personable

The person you’re calling is human too and wants to speak with an actual human, not an answer providing robot. If that weren’t the case, they wouldn’t be talking to you and would instead stick to email!

  • Be polite and respectful

You are taking up time in the other person’s day, and they are (probably) pretty busy. Respect their time and they will greatly appreciate you for it.

  • Have a smile when talking

I don’t how it works, but when you have a smile, the way that you talk and act just reflects that positive energy. Even if you’re doing a phone call, listen to a happy song to get you smiling beforehand or even force the smile. I promise they’ll be able to hear it through the phone.

Criteria of Good Questions to Ask During Coffee Chats

Asking the right questions is crucial to the success of your networking attempts. If the goal is to get a job or build a connection with the other person, they’re much more likely to help you out if you ask interesting and thoughtful questions.

Here are the 3 main criteria that every question you ask should pass:

You Can’t Find the Answer Online

Before the first meetup with my school’s golf coach, I remember him sending me a preparation email. It contained the address and time of the meetup, along with how the conversation would go. It was like many others I had received, but one line stuck out to me “do not ask me any question that you can find on our school’s website or on Google.”

That line forced me to really go in and do research on the school website and also on Google. By the time I chatted with him, I had picked out 3 niche questions that ONLY he could answer. On top of that, I researched the crap out of the school and team beforehand so I was very well prepared going into the conversation.

As a general rule of thumb, ask questions which you can’t find online. If you can easily search up the answer to the question on Reddit, why are even talking with this person in the first place?

Specific to the Person You’re Chatting With

This sort of ties in with the first criteria, but your question should be specific to the person you’re chatting with. What this means is that they should be uniquely situated to provide an answer to this question.

Overexaggerated example: “what is number of feet surgeons in Minnesota?”

You might not be able to find the answer to this question online, but unless the person you’re calling is a pediatric statistician working out of Minnesota, it’s not specific to them.

Instead, a question that both can’t be found online AND is specific to someone might sounds like: “what part of the job did you enjoy when you worked as a lawyer at XYZ firm?”

Not Too Easy, Not Too Hard

Finally, the last component of a good networking question is that it’s not so easy that they don’t need to even think, but not so hard as to frustrate them.

A question that’s too easy will show that you haven’t given any thought to the chat. On the contrary, a question that’s too hard will probably piss the person off (why should I spend the time to answer this question for this stranger?)

An example of a question that you “can’t find online” and also that’s “specific to the person you’re chatting with”, but is too easy would be something like: “Do you enjoy your work?”

This is specific to them, but it’s a really simple yes or no question that doesn’t get them to think.

Something which sounds virtually the same but is a much better question to ask is: “what are some aspects of your job that you enjoy and also which you dislike?”

This isn’t a yes or no question, but it isn’t so hard as to scare the person you’re talking to away. This question is open-ended and covers the previous two criteria (personal to the person you’re chatting with), but also is at a good level of difficulty.

Do NOTs for Questions

With every great question asked, there is a terrible one asked somewhere else in the world. You want to make sure that you absolutely eliminate the possibility of being the latter. Be it a common interview, or a coffee chat, asking bad questions can destroy your chances of building a relationship with the opposing party.

Aside from having your question follow the laid-out criteria above, here are a few do NOTs that you should be aware of:

  • Don’t ask “would you rather” questions unless you really get to know the other person. (Otherwise they just make you seem immature and silly)
  • Avoid asking anything probing or too personal (So basically steer clear of all date questions).
  • Don’t ask random questions unrelated to either the person you’re chatting with or your current topic of conversation.
  • Don’t ask about their “craziest” or “most embarassing” experiences during their tenure. (Though it may satisfy the above criteria, this can seem very odd to most interviewers)
  • Avoid asking anything regarding how to prepare for a future interview. (Instead you could go for something softer like “how could I best position myself to apply for so-and-so position?”)

Sample Questions

Now that you understand the criteria behind good questions, here are a few general ones that will work with almost anyone (if tweaked a bit).

  • What do you find the most interesting aspect of your job is / what is your favorite part of your job?
  • If you had to go back and advise yourself before starting this career path, what would you say?
  • How have your responsibilities shifted as you’ve progressed within this company?
  • Where do you see yourself in the future?
  • What motivates you to stay in this role; what makes you want to leave?
  • From your experience, how would you best characterize the company culture (of the place you’re working at)?
  • In your opinion, what weaknesses do most job candidates suffer that hurt them in the hiring process?
  • From your standpoint, what are the most boring parts of your role?

With some word adjustments, there should be many variations of these questions which you can build off and which can provide you with the backbone necessary to create your own good questions.

Questions YOU Might Get Asked

Even though a coffee chat isn’t exactly a job interview, chances are you’ll need to answer questions too. After all, you’re speaking to a human (see mannerisms section above) who wants to know about you too!

Depending on the person you’re chatting with, you could get light and funny questions or tough borderline interview questions. It’s best to be prepared for as many potential questions as possible. Here’s a list of questions that you might get asked:

  • Tell me about yourself (a classic question that is surprisingly easy to mess up)
  • What do you like to do in your spare time?
  • How do you feel about _______ regarding my company? (really tests how much homework you did)
  • Give me an example of a time when… (highly unlikely as a coffee chat question, but you never know…)
  • How often do you (insert semi job-specific verb: read the news, work with your hands, check your emails…)

Be sure to prep for these and also any other ones you think might be relevant. It’s always best to be overprepared than underprepared.

Get Out There and Network!

young lady typing on keyboard of laptop in living room; Good Questions to Ask During Coffee Chats
Good Questions to Ask During Coffee Chats

The networking process is one part reaching out to people, and another part leaving a good impression. Asking the right questions in coffee chats will help set you apart and make the person remember you.

Aside from basic mannerisms and being a human, the key characteristics of good questions are:

  1. You can’t find the answer online
  2. It’s specific to the person you’re talking to
  3. It’s not too easy, but not too hard

Once you’ve compiled 10-15 of these questions for your networking calls, the only thing left to do is to actually reach out. Follow these guidelines, send a thank you note after your chat, and you’ll find that people will remember you for a long time to come.

So what are you waiting for? Get out there and start building your network!


Thanks for reading through Good Questions to Ask During Coffee Chats and thank you for following along! If you’re a Canadian Student, check out the Ultimate Canadian Student’s Guide to Personal Finance! To learn more about me, head over to this link here. If you want to get exclusive updates and tips, drop your email in the “get updates” box (might have to scroll up a bit.) Let me know your thoughts and suggestions in the comments!

2 Comments

  1. Great networking advice Jeff! Especially love the part about not too easy, but not too hard. You want to make people think, but not frustrate them if they don’t know the answer.

  2. I don’t drink coffee but I do network extensively. One of the best ways I found was to buy a drink for the experts who taught the technical seminars my employer paid to send me to. Those people were the top leaders in their fields and I would catch them at the end of the day and buy them a nice single barrel scotch and ask them about their careers. Sometimes I’d toss out a vexing problem from work. One guy, an Australian PhD engineer, listened to my problem and proceeded to draw out a solution worth millions to my employer on a napkin. For free! Over time I ended up with the phone numbers and email addresses of many of the worlds leading experts in the technologies that powered my industry. It was a huge advantage that kept me promoted and highly paid.

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