Reading job descriptions only tells you so much. To really understand a role, a team, or a skill set, it helps to talk with the people who live it every day. Short, informal career conversations with colleagues, sometimes called coffee chats or informational conversations, are one of the most effective and low-pressure ways to explore your options inside your organization.
Think of them as a way to test ideas before committing to anything. A single conversation can tell you whether a role you’ve been curious about actually fits your strengths and interests, and it builds relationships across your company along the way.
How to ask for a coffee chat
Keep your request short, specific, and easy to say yes to. Mention why you’re reaching out, how much time you’re asking for, and what you hope to learn.
For example: “Hi Jordan, I’ve been curious about how the product team works and really admired your presentation last month. Would you be open to a 20-minute chat sometime in the next few weeks? I’d love to hear about your role and how you got into it.”
Questions to understand the role
- What does a typical week look like for you?
- What parts of your work take up the most time?
- What’s something about your role that most people don’t realize?
- How does your work connect to other teams?
- What does success look like in your role?
Questions to understand what the work feels like
- What part of your job energizes you most?
- What do you find most challenging?
- What kinds of people tend to thrive in this role?
- What surprised you most when you started?
Questions about skills and growth
- What skills are most important in your role?
- Which skills did you have to develop after you started?
- If you were starting out again, what would you focus on learning first?
- Are there projects, resources, or learning opportunities you’d recommend?
Questions about their path
- How did you get into this role?
- What experiences helped prepare you most?
- Were there any moves or decisions that turned out to be especially important?
- Looking back, is there anything you’d do differently?
Questions to keep the conversation going
- Is there anyone else you’d recommend I talk to?
- Would it be okay to follow up if I have more questions later?
- Is there a small way I could get exposure to this kind of work, like sitting in on a meeting or helping with a project?
Tips for a great conversation
Choose three to five questions rather than trying to ask them all, and let the conversation flow naturally. Listen more than you talk. Take a few notes afterward about what you learned and how it made you feel. Did the work sound energizing or draining? And always follow up with a thank-you message, mentioning one specific thing you found helpful.
Planning a career conversation, or not sure who to talk to first? A Bravely coach can help you decide who to reach out to, prepare your questions, and make sense of what you learn. Book a session here.
