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15 Questions to Ask Someone During an Informational Interview

People with questions regarding their career paths and have questions to ask someone in the same career that they want.

Meet someone who has your dream job? Ask them these questions to learn more about the career you want.

Breaking into a new field or industry can be both exhilarating and challenging, although the rewards can pay off tremendously. But you don’t have to jump blindly into something new without first trying to learn from someone who knows what it’s like to work in your field. An informational interview with someone who works in your chosen profession will help you decide whether you’re making the right career choice for you.

In this article, we cover 15 questions you should ask during an informational interview. By asking these questions, you’ll gain clarity about what the typical day-to-day looks like, what challenges you’re likely to face, what insider knowledge you should be aware of, and what tips and tricks might help you to accelerate your growth.

There’s no better way to get a head start in your career than to find a mentor who has walked the path themselves. Rather than making mistakes and learning from them on your own, you can use a mentor’s experience to avoid the common pitfalls within your industry — or even to consider a different direction entirely.

1. What drives you in your career?

Pushing through challenges and adversity is something that comes up in every career path, no matter what industry or field you’re in. Ask about the strong, singular purpose that drives your interviewee and gives them the mental strength they need to push through adversity and rise to success.

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2. What do you love the most about your job?

When someone is successful in their career, chances are that they love certain aspects of their job. They could be emotionally connected to their company’s products, the people they work with, or the end result of the output they produce and how it impacts their customers. If you can find out what they love most about their job, you’ll understand what aspects of your future work in the industry you can look forward to.

3. What are your strengths when it comes to leadership?

Good leaders are hard to come by, and if you can find someone in a leadership position who has led their team to success on numerous occasions, it’s time to listen in. Pay special attention to the soft skills they mention, such as empathy, compassion, creativity, and listening. Based on the leadership qualities they mention, think about how you stack up in each of these areas. Are there any leadership skills you can begin to work on before you start a career in the industry?

4. What technical skills have you relied on to get to where you are today?

Some careers are built off of technical skills, and finding out where your interviewee learned and developed their skills over the years can be invaluable to fast-track your own career. Get specific and ask them about the courses they took, workshops they participated in, and learning outcomes they achieved. Then ask how they would review their experiences in each area.

5. What books have made the most significant impact on your career?

Aside from a physical mentor who places you “under their wing,” books are the next best thing. By reading accounts of others who have gone through what you’re about to embark on in your career, you’ll understand what mistakes they made and what they learned from them. Ask your interviewee what books made the largest impact on them and why, and then read them for yourself as soon as possible.

6. How do you continue learning & growing as a professional?

Even when you’re just beginning your career, you can never stop learning and growing if you want to stay at the peak of your field. Ask about any professional organizations your interviewee is currently involved in, what media they consume, and what other avenues of learning they regularly pursue. Then go out and get access to their suggestions for yourself.

7. Who are your mentors? Who inspires you?

The most successful people in any field almost always have people who inspire them or mentors who help them throughout their careers. Ask your interviewee about what their early mentors taught them that helped them jump-start their careers. How do their current mentors help them at this stage in their professional development? If you’re brave, you can even ask them to consider taking you on as a mentee. Having a mentor will allow you to learn about some nuances of your industry quickly and avoid the pitfalls other new entrants may stumble on.

8. How did you find & connect with your mentors?

Once you’ve discussed their mentors and who inspired them in their careers, get specific regarding how they found these mentors in the first place. Were they introduced to them early in their career? Did they ask questions and seek out mentors? Was there a professional organization that connected them with their mentors? Once you know the best methods of finding a mentor, you can put in the work to find someone to mentor you on your own journey.

9. What is the best piece of advice you have ever received?

Many people can think of one pivotal piece of advice they received that flipped their past ways of thinking and made them accelerate in their chosen profession. Ask your interviewee what this piece of advice was for them and how it changed them moving forward.

10. What advice would you give to someone like me who eventually wants to be where you are?

Depending on how long they’ve been in the industry, there may have been significant changes over the years. Ask them what piece of advice they could give you that would be actionable today. Remember, the advice they give is an invaluable “gold nugget” of information — if you want to thrive, don’t ignore it but apply it to your own career path as soon as possible!

11. How do you make a memorable impact?

As we get older, we think more and more about the legacy and impact we’ve made on the world. As you’re interviewing and asking questions, ask them their thoughts on being remembered by the people they positively influenced in their careers. What have they done, or would like to do, to make a memorable impact on others?

12. What industry trends are you currently keeping an eye on?

When you’re new to an industry, you aren’t immediately aware of industry trends or what you should be keeping an eye on. Ask them what’s changing and where things are heading, and consider asking them how they came to these conclusions in order to hear their thought process.

13. How do you organize & manage your time?

If someone has been successful throughout their career, chances are high that they manage and organize their daily time efficiently. Ask your interviewee what time management tools they use or what tips, techniques, or tactics they suggest to maximize the productivity-to-time ratio.

14. What would you do right now if you found yourself in my shoes?

The answer to this question might include some of the most valuable advice you receive from this interview. This question shows you how an expert in your future career or industry would approach getting to where they are today, beginning with your current circumstances — an incredible bit of insight and wisdom that you can take action on immediately.

15. Are there any expectations you’ve had about your career that turned out to be different from reality?

When they started out in their career, they likely had some expectations that turned out to be completely false. Ask them what these expectations were, how they differed from reality, and why they think they had those expectations in the first place. Ask about both negative and positive expectations and whether there was anything that surprised them to the upside.

Final Thoughts

Setting up an informational interview can be a great first step to launching your dream job. Even if this is an informal meeting, be sure to treat it professionally and follow up with a thank-you email or handwritten note letting the person know how grateful you are and how much you learned. Be sure to pinpoint a few details they shared that resonated most. This will help keep you top-of-mind and might make them open to more favors. It also helps keep the lines of communication open for future mentorship or accountability partner opportunities.

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Last updated on Dec 19, 2023.

Originally published on Oct 13, 2022.

The views expressed in this article are those of the author and do not necessarily reflect those of Berxi™ or Berkshire Hathaway Specialty Insurance Company. This article (subject to change without notice) is for informational purposes only, and does not constitute professional advice.

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