Hindsight is 20/20. But perhaps one of the most beautiful things about that fact is that it doesn’t even have to be your own hindsight. Asking this question in an informational interview will give you the words of wisdom from someone’s hard-earned experience as well as the predictions they might have for where the field or industry is headed. It’s also a better question than some of the alternatives because you’ll leave with actionable insights. By contrast, if you ask someone: “Would you do it all again today? Would you make the same decision to go into this profession?”, they’re probably just going to say “Yup!” Because who wants to admit to an acquaintance that they regret one of the bigger life decisions they’ve made? Continue reading If you were just entering your profession now, what would you do differently? →

This question will give you a sense of how a field has changed over the years and where it’s headed in the future. And just as with the question about surprises in a profession, it’s particularly useful if you get two responses to this question as well: one response related to a positive change and one related to a negative change. Practicing medicine today is not what it was 25 years ago. Writing a blog today is not what it was 10 years ago. Mining bitcoin today is not what it was two days ago on July 9, 2016. These fields are moving targets. The ones you are exploring probably are too. Continue reading What would you say has been the biggest change to your job or field since you started? →

In Chip and Dan Heath’s mind-bogglingly useful (and entertaining) book “Decisive: How to Make Better Choices in Life and Work,” they talk about the importance of reality-testing your assumptions. In the context of a job search this means that you shouldn’t just assume that a new field or new position will be all roses. You should ask “disconfirming questions” that will help you see beyond your own personal bias. This particular question is not in the Heath brothers’ book, but it would count as a “disconfirming question.” Found out what vexes a person about her work and you’ll put yourself in a position to make a work decision that’s based more firmly in reality. Continue reading What part of your job would you say is the source of most of your work-related frustrations or stress? →

I really like this question as a closer for informational interviews or other “networking” type meetings. Instead of making the entire conversation about the information, connections, and direction YOU need, flip the script a bit. How can you help this person who has just been answering all of your questions? In an informational interview especially, odds are you’re talking because you come from different but overlapping backgrounds and professional circles. So you just might be exactly the right person to make a useful introduction or point out a resource that could help move things forward substantially. Not only does this give you good karma, it also provides you a way to stay in touch with this new contact (for example, if you happen across an article 2 weeks later that’s related to the issue that needed your help, you can remember to send it along). Continue reading How can I help you? →

About teaching? About medicine? About computer programming. Whatever the profession, it’s always good at least to try and learn the things that people only know after they’ve gotten into the field. And if the person you’re meeting with starts off her answer with a negative surprise, make sure to also ask about what has been the most surprising positive thing. For example, a teacher friend of mine said that he was surprised that he has never once reused a lesson plan verbatim. The days and school years are much more varied than he thought they’d be. He loves that. I followed up by asking what has surprised him in a negative way about teaching. He said the sheer craziness of some parents has been astounding. Continue reading What has surprised you most about ____ as your profession? →

If you’ve sought out an informational interview to learn more about a particular field or profession, this question is always a great one to ask. You’ll learn what a person truly loves about her work (the relationships, or the challenge, or the creative aspects…) and where else those things can be found outside of a single field. (As a total aside, a friend of mine is a medical dosimetrist. I had no idea that was even a profession until recently! It’s pretty cool. Google it.) Continue reading What would you do if you couldn’t do this? →

This phrasing might not be right for your particular situation. But let me explain the essence of this question with an example: A good friend of mine made a career switch from software engineering to high school teaching. He now cannot imagine doing anything else. I asked where he got the information that convinced him he should make the switch. He said that coaching high school football with his alma mater proved to him that he would enjoy the high school environment and find fulfillment in working with young people. After a season of volunteer coaching, he was able to leave his software job with confidence and start his new career in public education.

If you’re meeting with someone for an informational interview, chances are she works in a career field that you are interested in exploring, or she’s earned a degree that you’re eyeing, or she’s moved from one kind of job to another and you want to learn how she managed it. For all of these things, it’s important to know HOW someone started with an idea, said “Yes this is a good idea for me,” and moved on to action. Was it an intermediate experience (like volunteer coaching before full-time classroom teaching)? Was it observing? Was it talking with a certain person? Was it attending a Meetup event? It’s important to ask because these are the experiences you want to create for yourself. Continue reading What gave you the information you needed to move confidently from A to B? →