Here is a list of questions broken down by the phase of the conversation.

Note, you may want to start with a bit of small talk. One good opening question is, “How is your day going?”

Early on, you may want to ask questions such as:

I know a bit about what you do. But I was hoping to learn more. Could you share more about your background with me?
Frank Jones said you had done some really exciting things around X, Y, Z. I’d love to learn more about it.
It’s been a while since we last connected, could you catch me up on what you’ve been working on?

From there:

As a follow up question, I usually pick one topic that they shared with me, and ask them to give me a closer look:

That’s really interesting. I was curious about… Could you share a bit more about that?
That must have been really exciting to do…. What was that like?
It seems like there might be a really interesting story about… I’d love for you to tell me more.
Would you mind telling me a bit more about…?

The rest of the conversation may simply be diving deeper into this initial topic or moving between the topics shared. You can go deeper by simply asking for more of the story.

What was that experience like?
So how do you approach the problem of… And how has that turned out for you.
What did you do at that point?
How did that turn out?
That’s really interesting. How did you come to that…
• I’ve been thinking about a few things along those lines and curious to hear your thoughts, specifically what I was considering was…

Or you can move into another topic by asking:

One of the other things you mentioned earlier was… And I was hoping you could share more about that…
Something we haven’t talked about already was… And if you felt comfortable, I’d love for you to share more about your experience around that?

More traditional shop talk questions:

• What are you working on right now?
• What are the challenges that you see yourself facing over the next couple of years, or the industry in general?
• Where do you see the industry going?
• What surprises you most about your job?
• In my experience, I’ve dealt with… which was quite challenging. Have you experienced that before, and how did you solve it?
• How did you get involved with doing (insert job position here)?

For conversations where you are exploring a career:

What kind of people enjoy this work?
• What kind of people don’t? / Why do people get burned out?
• What have you enjoyed about this work?
• I know a little bit about XYZ, but would love to learn more. Can you tell me about that?

Learning and Growth Questions:

Are there books or conferences or other resources that you recommend, that have had a big influence on you?
• Are there any important trends coming into this space that I should study carefully?
• Are there any skills that you think are extremely important for someone to know today to be successful?
• What’s been one of your most valuable lessons/insights about how to succeed with…

Some other questions you might consider:

• What have you enjoyed most about your experience with this organization?
• As I am going through this transition, I have been thinking a lot about… I’d love for you to weigh in and share your thoughts.
• What’s it like to work at this organization / in this position type?• What has been your best experience working in this field / at this company?
• What does that look like on a day to day basis in terms of the types of work and projects that you take on?• How does someone who works at this company become successful?
 If you were hired into this role right now, what are the most important steps to take in the first 30 days, in order to be successful?
• What are some companies/organizations that you think are doing interesting work in the space? (if you aren’t focused on their company) 

Note: You may have a perceived limitation that you are worried about preventing you from getting a job. Ask your meeting partner to help you answer it.

“I have a long background in HR, but I want to next take on a strategy role. What approach do you recommend?”
“I have been working for quite a while, and I am wondering how I can best present this track record as an asset?”

Later on, very valuable

If you were in my shoes, what suggestions would you make about where to go from here?
•What resources should I look into?
What places would you suggest I look for interesting opportunities?