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Advice / Job Search / Networking

7 Questions You Can't Leave an Informational Interview Without Asking

You’re considering a certain career path. So, in an effort to learn more about it, you gather your courage, heed that age-old career advice, and connect with somebody who already works in the sort of position that you’re interested in.

Yes, you put yourself out there. The hard part’s over right?

Not exactly. Making the most of that conversation involves more than just sitting down at that coffee shop corner table, staring nervously over your latte, and eventually spouting out an awkward, “So… tell me about what you do.”

In order to get the insights you’re so eager to get your hands on, you’ll need to ask targeted and smart questions. Like what? Here are seven you should absolutely have in your back pocket.


1. “What Attracted You to This Career Path?”

Of course, it’s best to dip your toes in and start with the basics.

Kicking off your conversation with a question like this one will give you a greater understanding of what initially drew that person to this sort of position—which provides some necessary context as you move into the rest of your discussion.


2. “What Previous Professional Experiences Have Helped You Most in This Role?”

In a similar vein, don’t be afraid to dig into that person’s professional history. It’s always helpful to understand how somebody arrived at this current point in his or her own career.

Perhaps a specific certification has really given that person a boost in this position—meaning it’s something that you’d also want to look into. Or, maybe he needs to rely on a skill set he didn’t anticipate.

That’s all handy information to have as you consider making a move yourself.

3. “What’s Something That Would Surprise People About Your Day-to-Day?”

You might think that you know everything there is to know about that particular field. But, you’d be surprised—getting a peek behind-the-scenes is always incredibly enlightening.

Maybe everybody assumes she spends her days out in the field—but, her role actually requires a ton of desk work, for example.

Using a prompt like this one will empower you to find out more about those lesser-known parts of a specific position.


4. “What’s One Thing You Wish Somebody Would’ve Told You Before Going Into This Field?”

Sticking with that “surprise” angle, it’s worth digging more into that person’s head to find out what personally shocked him or her about that role.

Whether it’s the fact that he had no idea how much he’d need to rely on his math skills or he didn’t anticipate needing to collaborate with so many different departments, there’s bound to be some element of that job that was unexpected.


5. “What Are Some of the Biggest Rewards of Your Position?”

Of course, the goal of your conversation isn’t to just uncover any surprising or negative parts of that position. You want to find out what that person loves as well.

Perhaps the income can’t be beat or she loves that no two days are the same. Or, maybe the work is fulfilling and rewarding, and she knows that her work is contributing to the greater good.

Finding the right job for you involves finding one that lines up with your own values and priorities. So, it’s smart to touch on the most positive pieces of that role to see if they match up with your own ideals.


6. “How Would You Describe Somebody Who Would Excel in This Career?”

You’re eager to not only discover whether that type of position is what you’re looking for, but also if you’d be a reasonable fit for that sort of role.

The person that you’re meeting with will obviously have some valuable insights into what it takes to succeed in that job, and it’s worth asking how he or she would describe a qualified candidate.

If he or she touches on skills and competencies you already have? You’re well on your way. If not? At least you’ll know what you need to work on in order to present yourself as a seamless fit.


7. “What’s Most Important to Prepare for a Role Like Yours?”

Ideally, you’ll walk away from that conversation with a handle on your next steps. To get some actionable information that you can walk away with, end your conversation with a question like this one.

Is there a certain certification you need to get? A class you should take? Experience you have to have? Other people you should reach out to?

Find out what he or she recommends to help you adequately prepare for that job, and you’ll have leveraged that conversation to actually take steps forward.



When you’re considering a certain career path, informational interviews are an enlightening tool to lean on—provided you’re prepared to ask the right questions.

Make sure to use the seven included here, and you’ll maximize that coffee date—with as few awkward pauses as possible.