Ask Better Questions

The quality of a coffee chat depends heavily on the quality of your questions. Good questions help you understand the reality of a role, industry, company, or career path, and reveal things that are difficult to learn from a website.

What Makes a Strong Question

Strong questions are specific, open-ended, and connected to the professional’s actual experience — not questions that could be answered by a basic search.

Questions About Career Path

• How did you decide to pursue this path?
• What has surprised you most about how your career has developed?
• Looking back, what would you have done differently early on?

Questions About the Role

• What does a typical week actually look like for you?
• What kinds of problems take up most of your time?
• What part of the job is hardest to understand from the outside?

Questions About Industry and Market Context

• How is this industry changing right now?
• What do people outside the field usually misunderstand about it?

Questions About Skills and Preparation

• What skills separate strong early-career people from average ones?
• What should I be doing now to become a more credible candidate later?

Questions About Recruiting and Hiring

• What do you look for when hiring someone early in their career?
• What made a candidate stand out to you recently?

Questions About Culture and Fit

• What kind of person tends to do well in this environment?
• What kind of person tends to struggle here?

Questions About Trade-Offs

• What are the biggest trade-offs of this path compared to others?
• What do people underestimate about the downsides of this work?

Questions to Avoid

Avoid questions that could be answered by a thirty-second search, and avoid opening with requests for a job, referral, or resume review.

How Many Questions Should You Prepare?

Five to seven is a good range. You may not ask all of them — that is fine. The goal is not to rush through a list; the goal is to have enough structure while allowing the conversation to develop naturally.