Mastering the Informational Interview: Key Questions to Ask

The informational interview is one of the most overlooked yet effective tools in career development. Whether you're a college student, a professional considering a career change, or an industry veteran seeking insights, these conversations offer invaluable insider knowledge that you simply can't get from a job description or a company website. However, as with any tool, success depends on how effectively you use it. The best way to succeed? Ask the right questions.

Many people mistakenly approach informational interviews as a formal job interview, which puts unnecessary pressure on both parties. Instead, it’s about curiosity—a learning experience where the primary focus is on gathering information rather than securing a position. In this sense, it is often the interviewer, not the interviewee, who is driving the conversation. Here, I’ll outline several key questions you can ask during your informational interviews to ensure you get the most out of each conversation. These questions are not only geared towards gathering specific insights but also designed to build rapport with your interviewee and establish lasting connections in the professional world.

1. Can you tell me about your career journey and what led you to your current role?

Opening with this question is a great way to set the tone for a relaxed and personal conversation. Most professionals enjoy sharing their career stories, and this allows them to reflect on their successes, challenges, and pivotal moments. By starting with this broad, open-ended question, you not only get a sense of their path but also gain an understanding of how they made critical decisions, what factors influenced their choices, and how they arrived at their current position.

Why this question works:

• It encourages storytelling, which makes the conversation more engaging.
• You get a chance to see how their experiences might align with your own interests or struggles.
• Their reflections might offer unexpected insights into industry trends or job functions you hadn’t considered.

2. What does a typical day or week look like in your position?

This question helps demystify the day-to-day responsibilities of a role. It’s easy to have a romanticized view of a job title based on its description alone, but understanding what it really means to perform the tasks of the position is crucial. The answer to this question gives you concrete information about the job’s rhythm, key tasks, and how time is allocated—information that is often missing from official job postings.

Why this question works:

• It provides a real-world perspective on the role’s duties, helping you assess if it fits your skills and lifestyle.
• It can reveal nuances or overlooked aspects of a job that you might not be aware of.
• It can also highlight any potential work-life balance concerns.

3. What are the biggest challenges you face in your role, and how do you overcome them?

Every job has its challenges, and learning about these directly from someone in the role can help you prepare for them. Moreover, how the interviewee handles these challenges will provide insight into their problem-solving strategies and what it takes to succeed in the field.

Why this question works:

• It offers a candid look into the less glamorous parts of a job.
• It reveals key skills or qualities needed to navigate the role successfully.
• It helps set realistic expectations for someone interested in the field.

4. What skills or experiences are essential to succeed in this position?

This question zeroes in on what it takes to excel in the role. It’s not always about the degrees you hold or the certifications you have. Sometimes, intangible qualities like adaptability, communication, or even patience are more important than technical skills. This question helps you identify both the hard and soft skills that are most valued in the role, as well as potential gaps in your own qualifications.

Why this question works:

• It gives you insight into both the technical and interpersonal skills that are crucial for success.
• It can reveal opportunities for skill-building or learning that you hadn’t previously considered.
• It might guide you to relevant training programs or certifications.

5. What trends do you see shaping the future of this industry?

Every industry evolves, and staying ahead of the curve is critical for long-term success. Asking this question not only shows that you’re forward-thinking, but it also offers a chance to glean strategic insights that could help you future-proof your career. Whether it’s automation, remote work, or emerging technologies, understanding the trends affecting your chosen field can position you as an informed and adaptable candidate down the line.

Why this question works:

• It demonstrates your interest in the broader industry landscape.
• It offers a forward-looking perspective on where the field is headed.
• It can inform your long-term career planning and skill development.

6. How did you transition into this role?

Whether the person you’re interviewing transitioned within their company or shifted from another industry altogether, their journey can offer lessons for your own path. Maybe they pursued additional education or certifications. Perhaps they took a winding, unconventional route that you hadn’t considered. This question can provide inspiration for non-linear career paths and reassure you that there’s no one "right" way to reach your goals.

Why this question works:

• It showcases different career transition strategies.
• It reveals whether certain certifications, degrees, or experiences were truly essential.
• It can help you gauge how difficult it might be to switch industries or job functions.

7. What advice would you give to someone looking to enter this field?

While the entire conversation will likely be filled with valuable nuggets of advice, this question gets to the heart of what the interviewee believes are the key actions or decisions that lead to success. By asking for their advice, you also build rapport, showing that you respect their opinion and are eager to learn from their experience.

Why this question works:

• It encourages the interviewee to offer tailored advice based on your interests and aspirations.
• It may prompt them to share lesser-known tips or strategies.
• It gives you actionable steps to start implementing immediately.

8. How do you see your role evolving in the next few years?

This question not only speaks to the future of the job but also to the potential for growth within the role or company. If you’re thinking of pursuing this career path, understanding how it might evolve will help you determine whether it aligns with your own long-term goals. This question can also reveal whether the interviewee feels optimistic or uncertain about their position’s future, providing clues to the job’s stability.

Why this question works:

• It provides a sense of whether the role offers long-term growth opportunities.
• It can reveal trends in specialization, automation, or changing responsibilities.
• It helps you determine if the role is a good fit for your career aspirations.

9. What do you love most about your job, and what do you find most frustrating?

Asking about both the pros and cons gives you a well-rounded view of the position. It also humanizes the conversation, making it clear that no job is perfect. By learning what excites and frustrates someone about their job, you can better assess whether the position aligns with your own values and expectations.

Why this question works:

• It balances the conversation, acknowledging both the highs and lows of a job.
• It provides a realistic understanding of the job’s upsides and challenges.
• It helps you gauge how much personal fulfillment you might derive from the role.

10. Is there anyone else you recommend I speak to in this field?

Networking is about building connections, and an informational interview is a prime opportunity to expand your network. This question gives the interviewee a chance to introduce you to other professionals who could provide additional perspectives, deepening your understanding of the field. A successful informational interview should end with an invitation to continue the conversation with others, and this question can open those doors.

Why this question works:

• It increases your network and builds momentum for further learning.
• It shows that you value continued exploration and are eager to learn from multiple sources.
• It can lead to additional opportunities, such as mentorships or job referrals.

Conclusion: Maximizing the Value of Informational Interviews

Approaching informational interviews with thoughtful, open-ended questions not only helps you gather the insights needed to make informed career decisions but also allows you to build meaningful professional connections. The questions outlined above offer a powerful framework for engaging in conversations that go beyond surface-level details, enabling you to dig deep into the realities of a particular career path or industry.

Remember, the ultimate goal of an informational interview is not just to collect information—it’s to establish relationships that may prove beneficial in the future. If you ask the right questions, approach the conversation with genuine curiosity, and demonstrate your eagerness to learn, these interviews can be the key to unlocking new opportunities and charting a successful career path.