How To Ask Questions During A Coffee Chat That Will WOW Them

The goal of a coffee chat is to build a professional relationship with your guest by asking insightful questions and actively listening. During a coffee chat, after making a self-introduction and building some rapport, the majority of the time should be you asking the questions. Since you asked your guest for their time, it is your responsibility to ensure the conversation is productive.

A successful coffee chat should end with your guest saying “Wow, honestly you have some great skills, if you ever want a referral let me know”, depending on the relationship and seniority of the person. This post will guide you a few methods on how to work towards achieving that.

There are a few goals you should keep in mind when asking questions:
1) Ask for details that are non obvious, that cannot be found easily through a quick search on the internet
2) Demonstrate you came prepared for the call by showing your research
3) Display your knowledge of the industry by asking relevant, or company specific questions

If you ask the right questions, subconsciously you are signaling to that person that you are a great candidate for the job, and that you care about them (People only spend time preparing for calls when they care about the other person).

An example of the worst question you can ask on a coffee chat is “What is your day to day like?”

This question is the exact opposite of the three rules I mentioned above – It’s generic (shows no preparation), doesn’t display any of your industry knowledge, and puts the responsibility on the guest to figure out what specifically you want to learn about.

Observational Questions

The trick to asking a good question is to ask an observational question:

The structure is: I understand X… but how about Y?
“I understand Shopify’s main product is the online ecommerce platform, but as a sales rep at the company, what products do you specifically sell?”

This is a great question because it shows you did your research and displays you have some industry knowledge.

Here’s another example question:
At my previous company we would use SalesLoft to cold call people, and sometimes even text message them, which would sometimes surprise them, haha. At your company, what sales tools do you use to do outbound?”

By adding a little story to your question as well, it makes it a fun and interactive way for your guest to not only answer, but also gain a sense of who you are. The best observational questions take some preparation, but definitely pay off.

Example Topics to Ask A Salesperson During A Coffee Chat

  • Product – What is the specific product you sell?
  • Value Proposition: What business metrics are your customers usually most interested in improving?
  • Sales cycle: Is it higher volume like 10 deals a month or lower volume like 1-2 per quarter?
  • Quota: How does quota work? like $1mil quota?
  • Sales plan: Is it 100% base or is it 50/50 plan?
  • Territory: Is it Canada/US or both?
  • Pipeline: Do I have a SDR/BDR assisting with prospecting/qualification or is it mostly self-prospecting?
  • Management: What is the management style in terms of sales culture? I know some companies focus heavily on measuring cold calls, some just more on quota.

Take these topics, pair it with an “observation” from your research, and you’ll have some amazing questions!


Before the chat, I write out a list of questions in a Google Keep. I will split my screen so one window is the Zoom chat, and one window is my notes. I will also pull up their LinkedIn profile to refresh myself on who they are. From there I will prepare my list of questions using the process above.

Remember, networking is a skill that you develop over time. I’ve been doing this for over five years, and I still push myself to think of observational questions while glancing at someone’s LinkedIn profile, every time I chat.

Case Studies

Below is a recent example screenshot of one of my readers who have seen success using the methods outlined above. As you can see, you are most definitely not the only person that is spooked by the idea of reaching out and going on a coffee chat!


Be sure to keep these tips in mind when considering setting up your next coffee chat. Going on regular coffee chats may seem completely question for most of us, however until you try you never know what truly awaits. So get out of your comfort zone and broaden your horizons, one step at a time.

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