Updated May 1, 2021
The right informational interview questions can be the key to unlocking a career you love.
I came across the “50 cups of coffee” idea right as I was at my wits end in university. I knew I had to leave and build a career but didn’t know where to start. My humanities degree felt, well, useless.
The “50-cups-of-coffee-strategy”—recommended for anyone who wants to make a career transition—seemed promising.
So, in my first few months of leaving university, I had more than 50 cups of coffee with complete strangers.
Many of them I met on the app Shapr. I reached out to some of them on LinkedIn, and a couple were referrals. I sat and listened to them talk about what they did. Yes, I let them do most of the talking, asking as many questions as I could. By the end of 50, I had accidentally stumbled across the job that launched my career.
In the back of my mind, my intention was always to get a job. But my stated intention—and I stand by it—was just to meet people. I didn’t really have an agenda, other than to find out as much as I could about possible jobs. And since I had a PhD, and no idea what to do with it, it seemed like the best way to learn.
And learn I did.
By the end of 50 cups of coffee, I knew of virtually 50 different directions that my degree and experience could take me and, judging from the people I spoke to, most were interesting.
If you are planning a career transition, many people (myself included) swear by this 50-cups strategy, also sometimes called an “informational interview.”
For people who are scared of the word “networking,” informational interview might be a little more digestible. As you may know, if you’ve been reading this blog for any amount of time, I really believe that the best way to turn any degree into a career is by building your network.
So, if you are going on your first or your forty-first cup of coffee, here are 10 informational interview questions that changed my life, and you can use them too!
1. What is your job like?
Nice. Vague. Open ended.
Just like a lawyer questioning a witness, you don’t want to be too leading. Start with something like this and see where they take it. You want to give them space to tell you what they think is important. It’s here that you’ll learn things, because they’ll accidentally tell you things you didn’t even know you needed to ask about.
2. How did you get into your position?
Your path won’t look exactly like theirs if you decide to shoot for the same career, but you definitely want to know how they got there. Did they network their way in? Did they write a really fancy exam, or did they learn the ins and outs of accounting?
Everybody gets into a job somehow, and seeing someone’s route will help you to plot your own.
3. What are the hardest or most discouraging parts of your work?
Every job has them. If you thought that working outside of academia was going to be all sunshine and roses, I’ve got bad news. (BTW working inside of academia isn’t either.)
It’s important that you understand what the difficult parts of a job are. If you like to take your time and work slow, you might not want to work in an insanely fast-paced environment. If you like to be done at 5:00 pm every day, it’s important to know if you’ll be expected to stay in the office until 7:00 pm four days a week.
4. What are the most encouraging parts of your work? What do you love?
If you’re going to ask informational interview questions about negatives, do ask about positives too! I loved this part of the conversation, because it’s a great chance to see if the job’s a fit for you.
If they love to see the results of their work changing lives, you need to hear that—especially since a lot of us are programmed in academia to think of other career paths as being less meaningful.
Listen closely to what they say.
Are the things that they love also things that you would love? Are there things that fit within your core values?
5. How would someone get into a position like yours?
This is the money question. And people don’t mind answering it.
As I stood at the beginning of the hiring process, I couldn’t understand how organizations hired. It seemed to be an inscrutable witchcraft that was accessible only to the wisest of career gurus.
After working at a company, I knew within a few months exactly how someone could get hired there and what the best ways were. One company I worked for posted their jobs everywhere, but really paid the most attention to resumes they got through one obscure jobs site (that I’d barely heard of).
Another company looked like a research organization, but only really wanted people who had managed projects or events before. One place I’ve worked only paid attention to people who came in in person and never glanced at the enormous pile of resumes they’d solicited on career pages.
In fact, my best nugget of insider knowledge is that the secret backdoor into government jobs in Canada is via a contract, since the HR processes take such a long time (over 6 months usually!) that managers are forced to give short-term contracts just to have bodies to do the work. These often turn into permanent jobs if they like the person.
If you came and had a coffee with me, I’d tell you that (and I just did). But if you’re spending all your time filling out job applications on the Canadian government’s website you will have a long time to wait (although it’s still worth applying).
Insider knowledge is worth its weight in gold.
6. Where do you think your career might go next?
Pay attention here. If the person likes you and trusts you a bit, you might get a window into someone else’s career ladder. This can be really interesting and useful for your own career—since you can get a vision of a whole career progression rather than the moment in time the person is in.
When I asked this once in an interview, I found that the person was aiming to shoot for a high-powered political job next. I instantly saw how there was a path from mid-level government relations (which the person did) to the highest strata of the political spectrum.
7. What advice would you have for someone in my position?
Assuming this wasn’t a one-sided conversation, the person likely knows a bit about you. Explain to them what you’ve done and where you’ve been. Talk a bit about what you love about academia and what you hate about it (a BIT—don’t talk incessantly about academia or your research).
Then, ask them what they would do if they were in your shoes.
It’s always an interesting question that prompts a lot of reflection. They’ll start to give you ideas based on their knowledge of the world.
Some of these will be interesting and might change your career path.
Take what they say with a grain of salt, and no matter what the response say thank you and promise to think about it.
8. Can you give me a sense of what some salaries might look like for someone like me in your industry?
Yeah, don’t ask them what they make.
But a question like this can unlock a bit of an understanding of salaries without the awkwardness of you asking what they make.
They’ll probably tell you some big ranges for people at the beginnings, middles, and perhaps even ends of their careers, and these should give you a sense of what different levels might pay. They’ll also help you during salary negotiations if you know you’re way at the bottom of the spectrum.
9. Who else should I talk to?
I love this question! If you’re building your network, it’s like building a really big web of contacts. One of the easiest ways to meet someone is to get a referral from someone else. As one of your informational interview questions, make sure to ask for a name (and ideally a referral too) for the next person you should talk to.
In my experience, there is always somebody.
Don’t be afraid to ask for an introduction to that person. This is normal networking behavior. Or, if you don’t get a direct introduction, don’t be afraid to say “Cindy said I should talk to you,” when you reach out to the next person.
10. Does your company hire consultants? If so, how?
I do consulting now, and I know it’s something a lot of PhDs want to try. (I wrote a guide for consulting with a PhD here.) If you’re not interested in consulting, ignore this question. But if you would like to build a consulting practice with your PhD, this is a great opportunity to find out if and how they hire consultants.
Some companies keep a repository of names, you might get yours added to it. Some require applications to Request for Tenders/Calls for Proposals. Some just keep you in mind and they’ll give you a shout if they’re looking. No matter what, if you’re interested in getting into consulting, this can be a good way to get on a company’s radar.
These are my 10 favorite informational interview questions. If you want more exhaustive lists, there’s a great one here from the Berkeley Career Center. I also love this article from Career Contessa and this one from the Muse. Let me know if I missed any and keep me posted about your own experiences with informational interviews!