Questions to Ask a Speaker About Their Career

The questions

Open any question to see why it works.

1. 1

   How would you describe what you do to someone who has never heard of your job?

   A gentle opener that also does real work, because job titles hide more than they explain. If they cannot manage it without jargon, the rest of the session will float above the room, and you can follow up by asking what they made or decided last week.

2. 2

   What was your first job after school, and how did you get from that to this?

   Asking for the sequence surfaces the sideways moves and the years that get compressed into one line of a biography. Careers almost never look like the version in the introduction, and speakers are usually pleased to be asked for the real order.

3. 3

   Was there a point where you nearly did something completely different?

   The near misses are the most memorable answers in any career talk, and they show how much of a working life is timing and chance rather than plan. Follow up with what tipped it, since that is often something very small.

4. 4

   What does an ordinary day look like, start to finish?

   Speakers describe the highlights by default, because that is what they were invited to talk about. Asking for chronology brings back the meetings, the admin, the waiting and the parts they would never volunteer, which is what you need to judge whether you would like the job.

5. 5

   What part of the job would surprise us?

   This invites the story they did not plan and could not fit into the talk. Good speakers almost always have one, and it usually reveals the gap between the public image of the profession and the actual work.

6. 6

   What skills do you use every day that you did not expect to use?

   The answers are usually writing clearly, negotiating, reading a budget, or managing people who do not report to you. This is directly useful if you are choosing subjects or deciding what to practise outside your main interest.

7. 7

   What did you study, and how much does it matter to what you do now?

   Many speakers work in fields unconnected to their degree, and the answer is either that it does not matter at all or that one specific part is load bearing. Both are worth hearing, and the second is the one that changes what you should sign up for.

8. 8

   How did you get your first break, and would that route still work today?

   The second half is the part that matters to you, because entry routes close. If they say they were hired straight out of a bar job by someone who liked them, ask what the equivalent front door is now.

9. 9

   Who helped you, and what did they actually do?

   This turns the generic advice to find a mentor into something concrete: a phone call made, a name passed on, an early draft read. It also tells you what kind of help is worth asking for and what is reasonable to expect.

10. 10

    What is the hardest part of the job that you would still choose?

    This separates a complaint from a trade-off. Anyone can list annoyances, but naming the difficulty they accept on purpose shows what the job is worth to them and what you would have to be willing to carry.

11. 11

    What has changed in this field since you started?

    You get the trajectory rather than the snapshot, which is what you are actually planning against. A speaker who cannot name anything that changed may be describing a version of the field that no longer hires at the entry level.

12. 12

    What do you turn down now that you would have said yes to earlier?

    Reveals how their leverage changed and what standards they built along the way. It also quietly answers whether the early years of this career involve taking whatever comes, which is useful expectation setting.

13. 13

    What did rejection look like along the way?

    Every speaker has been turned down, and the polished version of the story leaves it out. Asking plainly gives permission for a real answer in a room where everything so far has been the highlight reel, and it is often the moment the session becomes useful.

14. 14

    How do you know whether you are any good at this?

    Some fields have scoreboards and some have almost no feedback for years, and that difference suits different people. Ask what they measure themselves against now compared with when they started.

15. 15

    What does the money look like at the start, and does it stay that way?

    Ask it plainly, because most speakers will answer plainly and everyone in the room wants to know. The starting figure and the plateau matter far more to your decision than what the very top of the field earns.

16. 16

    What is the difference between the people who last in this field and the ones who leave?

    You are asking them to generalise from colleagues they watched over twenty years, which produces a sharper answer than asking what it takes to succeed. The reasons people leave are often practical rather than about talent.

17. 17

    If you were twenty and starting now, what would you do first?

    This is the version of asking for advice that produces something specific instead of a platitude, because it forces them into today's conditions rather than their own. Push for a first step rather than a philosophy.

18. 18

    What would you say to someone whose family does not want them to do this?

    Common in the room and almost never voiced, so asking it is a small service to whoever is sitting quietly. The answer is useful secondhand, and speakers often have a version of this conversation in their own history.

19. 19

    What do you wish someone had asked you today?

    Hands the floor back for the thing they came to say and did not get to. It also tends to produce the most candid two minutes of the session, since they are no longer answering a question they have heard before.

20. 20

    Can I follow up with you, and what is the best way?

    The only question that extends the encounter past the hour. Keep the request small and specific, ask it at the end rather than in front of the whole room, and say what you would want to ask about.