Updated Aug. 31, 2023
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 wit’s end in university. I knew I had to leave and build a career but didn’t know where to start. My 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 no idea what to do with my degree, 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! Don’t ask all the following questions at once (that would be too much). But use this list of questions as prompts to help you get what you need to from your interviews!
Want to watch this instead of read? Check out the YouTube vid!
- What is an informational interview?
- How to prepare for an informational interview
- 10 informational interview questions
- 1. What is your job like?
- 2. How did you get into your position?
- 3. What are the hardest or most discouraging parts of your work?
- 4. What are the most encouraging parts of your work? What do you love?
- 5. How would someone get into a position like yours?
- 6. Where do you think your career might go next?
- 7. What advice would you have for someone in my position?
- 8. Can you give me a sense of what some salaries might look like for someone like me in your industry?
- 9. Who else should I talk to?
- 10. Does your company hire consultants? If so, how?
What is an informational interview?
An informational interview is a conversation with someone working in a field that interests you that you can use to assess whether you’d like to pursue a career in that field and how to do this. It IS NOT a job request or a job interview. And it IS NOT an informal interview (which is when a company is scoping out a job and casually talking to people).
It’s all about you exploring jobs. And that’s pretty cool!
What should be the goal of informational interviews
It’s pretty simple really. An informational interview should be to learn more about an industry from one person’s perspective. It helps you get the inside scoop on jobs and industries from people working inside. If you ask the right questions, you’ll be better prepared to apply for jobs in a particular industry or for a particular position.
So here’s the ultimate tip to have a productive informational interview. Treat it as an opportunity to learn. Not an opportunity to get a job. This is weird because it actually means that informational interviews are vital background for a job search, but aren’t necessarily part of that search. And you probably WANT to get a job.
But today, treat the interview as research, and things will go well for you. That’s the purpose of these informational interview questions.
Why should you do informational interviews?
There are three main reasons why I swear by informational interviews:
- Building social capital: “It’s not what you know, it’s who you know…” Gross? Maybe. But still a fact of life. And you can always meet new people and expand your network.
- Career exploration: It’s hard to know what career to choose. But meeting people helps you learn about new possibilities.
- Tapping the hidden job market: Don’t do it for the jobs. Seriously. But there’s no denying that informational interviews can help on this front! Sometimes meeting people can help you learn about jobs that aren’t posted OR get on the radar for ones that are.
How to prepare for an informational interview
Do your research on the field and the company so that you don’t ask questions that could easily be googled. This way, in the interview, you can focus on finding out the individual’s experience and advice for moving into their position, rather than facts.
Here are some other things to do before an informational interview:
- Learn about the company and what they do.
- Learn what you can about the person (ie. from LinkedIn)
- Show up on time and be professional
- Make sure you’re comfortable with the setting, time, etc. (ie. if you’re not comfortable meeting for a beer at happy hour, meet for coffee instead!)
- Bring a notepad!
You don’t need to ask each informational interview question below. Choose the ones that fit your situation.
51 Informational Interview Questions
20 Informational interview questions for career exploration
One of my favorite ways to use informational interviews is for career exploration!
These are awesome informational interview questions to help you make an informed decision about the roles you should be looking for in a specific industry. This is valuable information, and it can be hard to get.
This is the exploration phase of informational interviews, so be curious. After all, the easiest way to save yourself from the misery of a bad job match is to learn from someone else’s mistakes!
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. What is a typical workday like?
It’s fantastic to understand what a typical day would look like in a company that interests you.
3. How did you get into your current 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 plot your own.
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. What are the hardest or most discouraging parts of your work? What are your most frequent challenges?
Every job has them. It’s important that you understand what the difficult parts of a job are. If you like to take your time and work slowly, you might not want to work in an insanely fast-paced environment. If you like to be done at 5:00 p.m. every day, it’s important to know if you’ll be expected to stay in the office until 7:00 p.m. four days a week.
Finding out what their career challenges are is a good idea.
6. What would I need to be successful in your career field?
See if you can get some feedback on what it would take to thrive in their field. Who knows, they might have some good insights. And if they say, “willingness to deal with change,” and you hate it, that might be a good clue.
7. So, what emerging trends or challenges are currently your industry?
It’s always good to understand the industry dynamics and where a given field is going. This helps you spot new opportunities and avoid potential pitfalls (like an entire industry that’s about to disappear).
8. What future opportunities do you see for this industry?
It’s important to choose a career path that creates growth opportunities!
What professional development opportunities are there in your field?
9. 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).
Insider knowledge is worth its weight in gold.
10. What would be the next career move for someone like you?
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.
11. Any recommended resources for someone trying to break into this field?
you asked for advice already. But you can also ask about appropriate resources to check out. They mighty have access to things like training… you never know. Unless you ask!
12. 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.
13. What professional organizations do you belong to?
Some professional organizations are open for you to join, or even attend a conference. You might be able to get plugged in!
14. Does volunteer work matter?
If you’ve done volunteer work (or you’re thinking about it), you can see how it connects with your career of interest.
15. What kinds of activities should I be doing now to prepare for a career in this industry?
If your career is a few years down the road and you’re just exploring, make sure you know how to spend your time preparing!
16. What educational background is a good foundation for a career in this industry?
Whether you have an education yet or not, this can help you decide. Educational preparation is part of most careers, so make sure you know what it’s going to take!
17. What are the personal attributes or personal qualities that lend themselves well to success in this career path?
Know thyself. Yoda said that. Probably.
If you’re choosing a career path, make dang sure it’s one that fits the type of person you are!
18. What kinds of problems do you get to solve?
Most jobs involve some form of problem-solving. Figure out what type you’d be doing.
19. What kinds of decisions do you get to make?
20. How much flexibility is there in your career path?
Do you have a ton of options? Or are you locked in once you start?
10 Informational interview questions to evaluate a company
Another type of informational interviewing can be evaluating a company. In this case, you have a specific place you want to work at (say Google or Facebook) and you’ll talk to someone who works there about what it’s like and the kinds of experiences you can expect in that role.
21. What’s the office culture like at your company?
Everyone will probably have a different opinion, but it’s nice to see what your interviewee thinks. Find out what you can about the work environment.
22. What is the management structure?
This is probably one of the most underrated questions. It could be the difference between loving or hating your job.
Is the organization flat, with a CEO who has an open-door policy? Is everyone expected to mind their business and stay in their lane?
Trust me, it makes a difference.
23. Does the company organize any team-building activities?
It’s nice to know how the company promotes collaboration and teamwork. Some companies take the time to invest in training days, team building, etc. to foster a good environment.
24. How is the work-life balance?
Do you want the boss calling and emailing you with work on the weekend? Or are you a normal person who wants to be left the F- alone?
Ask about work-life balance. And ask for examples of how they’ve experienced the work-life balance.
25. What’s the remote work policy?
Let’s be honest, most human beings want to work remotely. So a big part of scoping out a company is finding out their attitudes.
26. Does the company invest in its employees? If so, how?
Choosing an employer who invests in their employees and creates opportunities for your growth is awesome! Is there paid in-person training or online learning? Conferences? Education? Find out!
Companies that invest in their employees should help you identify career goals and grow into them.
27. Is there a dress code?
It’s becoming less and less common to have one, but find out if there’s a dress code!
28. What does it usually take for someone to be a good fit at your company?
If you were hired at that company, what would it take for you to feel like they belong? Find out!
Note that it probably varies depending on the type of job or type of position you’re interested in.
29. How does your company initiate new hires?
Sometimes, you can tell in the first few days of a job whether it’s right for you or not. Make sure to ask questions about what to expect.
30. How does your company handle sick leave?
This may or may not be a question that matters, but if you have chronic illness or health issues it’s good to know.
31. What are the company’s core values? How do they integrate into the workplace?
Any company has things that it stands for–or says it stands for. Figure out what they are. But–even more importantly–find out how they’re actually implemented into daily work. (Clue, if your informational interviewee can’t tell you, that’s a bad sign.)
32. What moves has the company made for diversity, equity, and inclusion?
If you want to work at a forward-thinking company that promotes safe spaces for everyone, this is a great question to ask.
33. What are some things your team has achieved that were exciting?
Finding out about recent accomplishments can help you decide whether the company is working on things you could get excited about.
34. How do teams work together?
It’s related to the workplace style, but find out how teams collaborate. Does everyone go off and do their own thing? Is Slack on fire all day with chat? Or are you in an office working closely together?
35. What’s the employee turnover rate?
Again, this can be a red flag. If there are people leaving all the time, it’s a sign that the workplace might not be as great as they think. And if your informational interviewee blames the people who are leaving, it’s a major red flag for a toxic workplace. (e.g. “We keep hiring people who are really useless.”)
36. What would employees say they love about the workplace?
37. What would employees say is challenging about the workplace?
This is a great opportunity to get some honest input into the things that are challenges. Every workplace has them, so don’t be put off by them. But do listen closely to how challenges are being dealt with.
38. Does the company reward employees who do well?
Employee of the month? Extra vacation days after a period of hard work? Companies that take extra time and money to spend on employees who perform are great to work for.
39. How much holiday time can I expect?
Most companies have standard vacation allowances. Pay attention to the extras like holiday office closures, which can make a big difference.
40. How is the company innovative and keeping fresh in the industry?
It may not matter much, but if you’re working in a field that’s evolving, it’s nice to be in a company that’s growing with the times.
5 Questions to identify your key skills
41. What kinds of skills should I have to get hired here?
Understand which specific skills the job needs and how your skills and abilities relate.
42. What skills should I be developing?
Feel free to talk about skills you’re seen in a job description if it helps.
43 What kind of background do most of the people in this industry have?
It’s not carved in stone that you all need to share the same backgrounds. But it can be helpful to know what you’re dealing with. And it’s nice to know where your personality traits fit.
44. What types of jobs would someone with my skillset be doing?
If you have a good understanding of what your transferable skills are, be straight up. Ask where they might fit!
45. What are the main skills you use every day?
What skills does your interviewee use? Knowing this can help you understand how to frame your own skillset.
3 Questions to help you nail a job application
Okay, so finally, there are some questions you could ask about applying. I wouldn’t do this in every case. But often, asking generic questions about how a company (or even your interviewee) handles job applications can be okay. (Note – I wouldn’t ever ask someone to look at your resume unless they ask or offer.)
Here are some questions that can help you thrive in traditional job interviews.
46. How can I make a good impression on my job application?
This is a generic question but it might give you some good insights.
47. What would you say are common features of successful cover letters you read?
If the person is involved with hiring, sometimes you can get some generic advice about what they’d look for in cover letters. Again, the word here is generic. If you’re asking specific questions about a job coming up, you might find yourself crossing a line.
48. What are the characteristics of employees who successfully interview?
Find out some generic observations about the employees who have landed jobs recently.
4 more informational interview questions to ask
Last, but not least, here are 3 more additional questions I think are sort of interesting.
49. Can you think of any other questions I should have asked and didn’t?
I like this question because sometimes you don’t know what you don’t know. Keeping it open ended lets them think about what they think you should know.
50 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.
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.
51. 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 the right 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.
52. Does your company hire consultants? If so, how?
I do consulting now, and I know it’s something a lot of people want to try. (I wrote a guide on how to start a consulting business here.) If you’re not interested in consulting, ignore this question.
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 finding consulting clients, this can be a good way to get on a company’s radar.
10 things to keep in mind while informational interviewing
- This is an informal meeting
Don’t take it too seriously. Be casual. Don’t pepper your interviewee with questions.
- Don’t ask all these questions
If you came to interview me and asked me 51 questions, I’d never talk to you again. These are to help inspire you and give you ideas–this isn’t a laundry list you should check off.
- As often as you can, ask open-ended questions
Don’t be too set in the answers you think you need. Asking open-ended questions can be a great way to learn things you don’t know you don’t know.
- Be safe
You have the right to feel safe when you’re informational interviewing. If someone agrees to meet with you but then asks you to join them for cocktails, feel free to suggest a morning coffee meeting instead. You have the right to feel safe and comfortable–even if someone is doing a nice thing by granting you the informational interview.
- Be professional
Duh, you’re exploring workplaces here. Maintain yourself professionally at all times. If you find yourself sharing workplace gossip from a past life or complaining about a previous boss, you’re over the line.
And you’re giving the interviewee reasons to have red flags about you.
- Stay away from personal questions.
The questions above are directed to your interviewee, but most of them aren’t personal. Asking what their salary is, where they live, or whether they’re married is personal information that isn’t your business.
- Don’t be afraid to ask for what you need.
That being said, they did agree to meet with you. So do ask some of the questions above, even if a few are uncomfortable to ask.
- Don’t send a copy of your resume unless they ask for it
An information interview is a fact-finding mission, so refrain from treating it like a secret job interview.
It’s possible your interviewee might say something like, “Send me your resume. We have some jobs coming up that might fit.”
If so, great! Send away. But don’t send it unless they ask.
- Keep the small talk to a minimum.
I once wasted 30 minutes of an interview on small talk, when I asked some questions to be polite and he wouldn’t shut up. And I was too scared to get a word in edgewise.
I try to limit small talk.
- You can email a follow-up question
If there’s something you forget to ask, don’t sweat it. Make sure you get their contact info and feel free to email another question after.
- You don’t need a business card. But it can be nice.
Business cards are still the norm in some industries–although younger people mostly just use LinkedIn. But if you want to get one you can. Expect that some people will probably give you one–and it’s handy to have the contact information from them.
- Don’t ask them to contact the hiring manager for you.
This is about research–not a specific job. Ironically, an informational interview will help you get a job. But asking directly if they’ll introduce you to the hiring manager can put them in an awkward situation.
But if they offer it, great.
Where to find people to do informational interviews
Remember, these are just information interviews. You don’t need people who are hiring. You don’t need people from your favorite companies. You really should talk to almost anyone you can.
I mean almost ANYONE. Because interviews prompt more interviews–even your friend in a totally unrelated field might know someone you should talk to. Just get started!
- Ask family members
- Consult friends who are already working
- Connect with alumni groups
- Reach out on LinkedIn
- Go to conferences
- Join professional associations
- Ask past teachers or profs for recommendations
- Cold-email people at companies that interest you
- Get to places where you can meet people (church, yoga class, rock climbing, etc.)
Create a list of people you’re interested in talking to.
Questions you shouldn’t ask in an informational interview
- Can you make me a job offer?
- Would you hire me?
- Can you help me get hired for X job?
These are my 52 favorite informational interview questions. I hope they help you as you search for your next idea position. And watch to see the opportunities that open up as you expand your network!