top of page

10 Questions To Ask Someone About Their Career

Updated: Mar 15, 2021

Ask More Questions
Ask More Questions

If you are considering exploring another career, the first thing you're going to do is to speak to as many people as you possibly can who are already working in that industry. Whether it's at a networking event, a phone call, skype or over a cup of coffee, you'll want to ask them every question you can think of.

But, what are the best questions to ask, so that you can get a genuine sense of what it's like to work in that job? Well, I have done the research for you. During my sabbatical, I interviewed over 300 people in 25 different industries, and the 10 questions below are the best ones that I found to get answers quickly and in a friendly manner. Let me know how you get on!

1. What has your career path been?

Start by asking about their journey in a more generic way. Chances are, you have already googled them and know the rough outline, but it’s a good way to start the conversation and relaxes you both. They might come out with something totally unexpected which will catch you by surprise.

2. Why [this industry]?

Learning about their motivation can help to give you an insight into your own drivers, which can open up a deeper conversation between the two of you on this.

3. What is your current role like? What about it makes you want to get up in the morning?

An overview of their job is an obvious conversation starter. The second question, though, encourages them to consider all the highlights of their role. Some people will answer with very specific points about their current job whereas others may talk about more general attributes or themes.

4. What does an average week look like for you?

Getting a sense of someone’s day-to-day schedule will give you the best idea possible of what it would be like if you were working there. Often people answered with what projects there were working on. Whilst this is, of course, a useful part of the conversation, what you also want to get at is how much time is spent in meetings versus travelling versus feeding the animals, or whatever it might be.

Asking this question often challenged some of my glamorizing assumptions about certain jobs, making me realise just how much time was spent in meetings or at a desk, for example.

5. What are your career aspirations?

This is to open up a conversation on where this career path might take you in the future.

What are their goals? Mine is to be this guy.
What are their goals? Mine is to be this guy.

6. Do you feel like you’re making a difference in your job?

You can replace this with the things that are the real deal-breakers for you. This was it for me.

7. Are there any expectations you had about this career path that you have found differed from reality, in both a good or bad way?

Another point to challenge your assumptions about this career. This can be a difficult question to answer, so try giving an example of something that you’d assumed to be true in this career. For example, corporate law has a reputation for very long hours and poor work/life balance.

8. What don’t you like about your job/a career in x? What are the biggest challenges? What are the compromises?

This is one of the most important questions to ask. You need to know about this just as much as you need to know about the good bits; there is no such thing as a prince charming job. Every job has its downsides and you need to be aware that from the very beginning rather than five years down the line. This lets you make a more informed decision on if the compromises are worth it for you, and for where you.

9. What skills are the most crucial to succeeding in this career? What type of person do you need to be?

Having an idea of the answer to this question will highlight any gaps you have in your skillset at the moment, showing what you might need to focus on building up. The second part of this question will give you some insight into the soft skills needed and whether the working environment is right for you.

10. What the best bit of advice you have for someone looking to move into this area?

This question is, of course, very helpful. It will also allow you to segue into your elevator pitch and request for work experience, assuming that’s what you want after everything you’d just heard, that is!


If you found this article helpful, check out my book for lots more advice (and a few adventures!). The Radical Sabbatical is a bestselling career guide, named the Financial Times Business Book of the Month 🎉

Check out my other blogs on:



bottom of page