By Emily Moore

Informational interviews -- casual conversations with people whose careers you admire and want to learn more about -- may not always directly lead to job offers, but they can still be a powerful tool in your job search toolkit. Beyond giving you the scoop on the role, company, or industry you're targeting, they can often provide you with insider advice that will give you a leg up on the competition. They can even put you in touch with folks who have the power to refer you to a position or maybe even hire you. Still, you have to be careful when thinking about which questions to ask in an informational interview.

Although you want to ask questions that will benefit your job search, you need to make sure that the questions aren't so self-serving, tone-deaf, or cliche that you irritate the person you're speaking with.

A man sits across from a woman and a man, as if in an interview.

Image source: Getty Images.

"The best questions are those that elicit useful responses and create a positive impression about you," says Joseph Liu, career change consultant and host of the Career Relaunch Podcast.

Wondering which questions fall into that category? Take a look at the seven suggestions below for starters.

1. Can you tell me about your first role when you started your career?

Many people reach out to senior-level employees when scheduling an informational interview, which makes sense -- a seasoned veteran working in the role, company, or industry you're interested in will have more years of experience to draw upon when sharing insights and advice. But don't make the mistake of forgetting to ask how they got their start, as this will likely be the most valuable information for you to have.

"The biggest challenge with informational interviews is that discussion tends to focus on the more senior or glamorous roles within the candidate's career track and not how one got there," says Sarah Doughty, director of recruitment of IT recruitment company TalentLab. "The reality is that in most industries, newcomers will start with small job scopes, doing work that doesn't relate at all to what they discussed in an informational interview. If a newcomer can't perform well enough in early roles, they will likely never be given a chance to move their career toward more fulfilling work. It's important to understand where you will start, and how hard you will have to work to get to where you want to ultimately be."

2. What are your favorite and least favorite aspects of your job?

When you're really interested in a particular career path, it's easy to focus only on the positive aspects of it. But any job, no matter how glamorous, will have its downsides, so it's important to get a truly holistic view of what the job entails.

Asking about somebody's favorite aspects of their job has the benefit of "[helping] you find out what the key motivational tool is for this employee to come to work every day. If you find yourself getting excited while listening to their answer, there's a good chance you'd thrive in this company," says Steve Pritchard, HR Manager at Checklate. "However, you do need a balanced view, so it's vital that you follow that question up with what their least favorite part of the job is... combine the employee's answers to gauge whether you'd be truly happy working at this company [or] in this role."

3. What is one piece of advice you wish you'd received before starting your career in this field?

One of the great things about speaking with somebody who's further along in their career than you are is that they were in your position once, so they have plenty of hindsight to share. Tapping into this knowledge will allow you to avoid the same mistakes as they did, or perhaps capitalize on the same opportunities as them.

"There are aspects to any job that will sooner or later appear out of left field. Whether it's more technical skills than one originally predicted or less teamwork than one envisioned, reality can often differ from our original expectations in any role," says Roger Maftean, career expert at ResumeLab. "Inquiring about this facet shows wisdom and foresight on behalf of a potential candidate and exposes any gaps in one's understanding of the full scope of the position."

4. What do you think is going to be the biggest skill required for success in your role 10 years from now?

In a high-tech, fast-paced world, the labor market is constantly evolving. And although you might have the skill set for the job now, you'll likely have to expand your repertoire at some point in the future.

"Most informational interviewers do not account for industry evolutions and strictly focus questions around what it takes to be successful now rather than later," Doughty says. "This is a mistake and one that can easily be avoided by simply recognizing that no role and no industry stays consistent for very long."

Asking the question above, though, will give you insight into where the field is headed and how you can stay ahead of the curve.

"Use your informational interview to get an insider's sense of where the industry or career track is going, not where it currently resides," Doughty advises.

5. If you could go back in time and choose again, would you choose to enter this field? Why or why not?

It's one thing to be comfortable in your job, but it's another thing entirely to be so passionate about it that you'd do it all over again. So if you're looking for a job that you'll truly love, this question is a must-ask.

"Zooming out and taking a more panoramic view of the decision (often many years ago) a professional made can expose key insights for anyone asking this question. Often, the hidden nuggets of wisdom don't get [unearthed] until one stops and takes a look at the 'bigger picture,'" Maftean says. "Ironically, the answer here can be quite revealing and even paradigm-shifting for both parties. After all, 'To know thyself is the beginning of wisdom.'"

6. Is there anything you feel I should know before applying to roles in your field? 

Informational interviews primarily serve the purpose of giving you the scoop on what it's really like to work in a particular role, company, or field (hence the name). But if you play your cards right, an informational interview can also give you a competitive edge over other candidates.

"This question allows you to get some insider tips on principles for success and/or common pitfalls candidates should keep in mind before formally applying for a role," Liu explains. "It also demonstrates you're really trying to do your research and due diligence prior to applying to a role," which is bound to impress the person that you're speaking with -- maybe even to the point that they offer to help you in your job search.

7. Who else should I talk to about working as a [job title]?

Another great way to boost your odds of landing a job, asking this question can directly benefit your job hunt without sounding too self-serving.

"That's the question that can send your hireability chances to the moon," says Michael Tomaszewski, Career & Workplace Expert at career site Zety. "That's because you might get backdoor access to people in the field you would otherwise never have a chance to meet and interview."

And given the importance that networking and references play in helping people score job offers, getting access to new contacts can be invaluable.

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